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Contents
Articles
Overview 1
Soap 1
Chemistry and soapmaking 10
Amphiphile 10
Fatty acid 12
Lye 19
Melt and pour 22
Rebatc...
Prepodyne 61
Resin soap 61
Saddle soap 62
Soap made from human corpses 62
Stainless steel soap 66
Sugar soap 67
Miscellany...
Kerala Soaps Limited 129
L'Amande 130
Lano (soap) 130
Lava (soap) 131
Lever 2000 132
Lifebuoy (soap) 136
Liril 137
Lux (so...
1
Overview
Soap
A collection of decorative soaps, often found in hotels
Two equivalent images of the chemical structure of...
Soap 2
Mechanism of cleansing soaps
Structure of a micelle, a cell-like
structure formed by the
aggregation of soap subuni...
Soap 3
History of cleansing soaps
Early history
Box for Amigo de Obrero (Worker's friend) soap
from 20th century. Part of ...
Soap 4
15th–20th centuries
Ad for Pear' Soap, 1889
1922 magazine advertisement for Palmolive
Soap.
In France, by the secon...
Soap 5
Liquid soap
Manufacturing process of soaps/detergents
glycerol recovered. The cold-process and hot-process (semi-bo...
Soap 6
some level of "trace", which is the thickening of the mixture. (Modern-day amateur soapmakers often use a stick
ble...
Soap 7
Molds
Many commercially available soap moulds are made of silicone or various types of plastic, although many
soap-...
Soap 8
References
[1] IUPAC. " IUPAC Gold Book – soap (http://goldbook.iupac.org/S05721.html)" Compendium of Chemical Term...
Soap 9
External links
• Handmade soapmaking information, resources and mailing list (http://www.natural-soapmaking.net/)
•...
10
Chemistry and soapmaking
Amphiphile
Phospholipids have amphipathic character.
Amphiphile (from the Greek αμφις, amphis:...
Amphiphile 11
Biological role
Phospholipids, a class of amphiphilic molecules, are the main components of biological membr...
Fatty acid 12
Fatty acid
Butyric acid, a short-chain fatty acid
In chemistry, especially biochemistry, a fatty acid is a c...
Fatty acid 13
Unsaturated fatty acids
Comparison of the trans isomer (top) Elaidic acid and the cis-isomer oleic acid.
Uns...
Fatty acid 14
Examples of Unsaturated Fatty Acids
Common
name
Chemical structure Δ
x C:D n−x
Myristoleic
acid
CH3
(CH2
)3
...
Fatty acid 15
Saturated fatty acids
Saturated fatty acids are long-chain carboxylic acids that usually have between 12 and...
Fatty acid 16
n−x
nomenclature
n−3
n−x (n minus x; also ω−x or omega-x) nomenclature both provides names for individual
co...
Fatty acid 17
Safflower oil 10.2 12.6 72.1 0 40.68
Hemp oil 10 15 75 0
Canola/Rapeseed oil 5.3 64.3 24.8 0 22.21
Reactions...
Fatty acid 18
Within the villi, the chylomicron enters a lymphatic capillary called a lacteal, which merges into larger ly...
Fatty acid 19
External links
• Lipid Library (http://www.lipidlibrary.co.uk/)
• Prostaglandins, Leukotrienes & Essential F...
Lye 20
Safety
Lye is a strong alkali, producing highly basic solutions. Both wet lye and dry lye solutions are highly caus...
Lye 21
Soap Making
Both sodium hydroxide and potassium hydroxide are used in soap making. Sodium hydroxide is often used t...
Melt and pour 22
Melt and pour
Melt and Pour Soap Crafting is a process often used by soapmakers. The process differs from...
Saponification 23
Saponification
Saponification of a triglyceride (left) with sodium hydroxide to give soap and glycerine
...
Saponification 24
The alkoxide is more basic than the conjugate base of the carboxylic acid, and hence proton transfer is ...
Saponification 25
Saponification in art conservation
Saponification can occur in oil paintings over time, causing visible ...
Soap substitute 26
Soap substitute
A soap substitute refers to detergents or cleansing creams, other than soap, for cleani...
Soaper 27
Soaper
In modern slang, a soaper is a person who practices soap making. It is the origin of the surnames "Soper,...
Sodium palmate 28
Sodium palmate
Sodium palmate[1]
Identifiers
CAS number 57-10-3
[2]
 
PubChem 985
[3]
ChEMBL CHEMBL82293...
Sodium palmate 29
Palmitic acid has been shown (in rats fed on a 20% fat (palmitic acid), 80% carbohydrate diet) to alter ...
Sodium palmate 30
Dietary effect
According to the World Health Organization, evidence is "convincing" that consumption of ...
Sodium stearate 31
Sodium stearate
Sodium stearate
Identifiers
CAS number 822-16-2
[1]
 
PubChem 2724691
[2]
ChemSpider 12...
Sodium stearate 32
Production
Sodium stearate is produced as a major component of soap upon saponification of oils and fat...
Sodium tallowate 33
Two equivalent images of the chemical structure of sodium stearate, a typical soap.
Soaps are key comp...
Sodium tallowate 34
Fatty acid content of various fats used for soap-making
Lauric acid Myristic acid Palmitic acid Steari...
Sodium tallowate 35
Islamic history
A 12th century Islamic document has the world's first extant description of the proces...
Sodium tallowate 36
1922 magazine advertisement for Palmolive
Soap.
Liquid soap
Manufacturing process of soaps/detergents
...
Sodium tallowate 37
Cold process
Even in the cold-soapmaking process, some heat is usually required; the temperature is us...
Sodium tallowate 38
Traditional Marseille soap
Hot processes
Hot-processed soaps are created by encouraging the saponifica...
Soap Industry
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Soap Industry

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This PDF presents the details of various process that go inside in a soap manufacturing process and it also describes about various soaps available in market.

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Soap Industry

  1. 1. PDF generated using the open source mwlib toolkit. See http://code.pediapress.com/ for more information. PDF generated at: Thu, 16 Aug 2012 14:40:07 UTC Soap
  2. 2. Contents Articles Overview 1 Soap 1 Chemistry and soapmaking 10 Amphiphile 10 Fatty acid 12 Lye 19 Melt and pour 22 Rebatching 22 Saponification 23 Soap substitute 26 Soaper 27 Sodium palmate 28 Sodium stearate 31 Sodium tallowate 32 Total fatty matter 41 Unsaponifiable 42 Types of soap 43 Aleppo soap 43 Antibacterial soap 46 Azul e branco soap 48 Carbolic soap 48 Castile soap 49 Cuticura soap 50 Detergent 51 Foam soap 54 Glycerin soap 55 Marseille soap 56 Nabulsi soap 57 Oil of guaiac 60 Phisoderm 60 Popish soap 61
  3. 3. Prepodyne 61 Resin soap 61 Saddle soap 62 Soap made from human corpses 62 Stainless steel soap 66 Sugar soap 67 Miscellany 68 Chlorogalum 68 Hand washing 70 Hygiene 79 Mount Sapo 91 Soap bubble 92 Soap dish 96 Soap dispenser 97 Soap scum 98 Washing out mouth with soap 99 International Nomenclature of Cosmetic Ingredients 102 Brands 105 Ach. Brito 105 Barf (soap) 106 Biechele Soap 106 Boraxo 107 Camay 108 Caswell-Massey 108 Chandrika (soap) 110 Defense Soap 111 Derreck Kayongo 112 Dettol 113 Dove (toiletries) 115 Fels-Naptha 117 Fenjal 118 Gossage 119 Hamam (soap) 121 Imperial Leather 122 Irish Spring 124 Ivory (soap) 125
  4. 4. Kerala Soaps Limited 129 L'Amande 130 Lano (soap) 130 Lava (soap) 131 Lever 2000 132 Lifebuoy (soap) 136 Liril 137 Lux (soap) 138 Margo (soap) 142 Medimix (soap) 143 Mysore Sandal Soap 143 Pears soap 145 Rozalex 150 Safeguard (soap) 151 Sapolio 152 Sebamed 154 Shower Shock 155 Simple Skincare 156 Sunlight (cleaning product) 159 Swan Soap 160 Swarfega 161 Wright's Coal Tar Soap 163 Zest (brand) 166 References Article Sources and Contributors 167 Image Sources, Licenses and Contributors 173 Article Licenses License 176
  5. 5. 1 Overview Soap A collection of decorative soaps, often found in hotels Two equivalent images of the chemical structure of sodium stearate, a typical soap. In chemistry, soap is a salt of a fatty acid. [1] Soaps are mainly used as surfactants for washing, bathing, and cleaning, but they are also used in textile spinning and are important components of lubricants. Soaps for cleansing are obtained by treating vegetable or animal oils and fats with a strongly alkaline solution. Fats and oils are composed of triglycerides: three molecules of fatty acids attached to a single molecule of glycerol. [2] The alkaline solution, often called lye, brings about a chemical reaction known as saponification. In saponification, the fats are first hydrolyzed into free fatty acids, which then combine with the alkali to form crude soap. Glycerol, often called glycerine, is liberated and is either left in or washed out and recovered as a useful by-product according to the process employed. [2] Soaps are key components of most lubricating greases, which are usually emulsions of calcium soap or lithium soaps and mineral oil. These calcium- and lithium-based greases are widely used. Many other metallic soaps are also useful, including those of aluminium, sodium, and mixtures of them. Such soaps are also used as thickeners to increase the viscosity of oils. In ancient times, lubricating greases were made by the addition of lime to olive oil. [3]
  6. 6. Soap 2 Mechanism of cleansing soaps Structure of a micelle, a cell-like structure formed by the aggregation of soap subunits (such as sodium stearate). The exterior of the micelle is hydrophilic (attracted to water) and the interior is lipophilic (attracted to oils). When used for cleaning, soap serves as a surfactant in conjunction with water. The cleaning action of this mixture is attributed to the action of micelles, tiny spheres coated on the outside with polar hydrophilic (water-loving) groups, encasing a lipophilic (fat-loving) pocket that can surround the grease particles, causing them to disperse in water. The lipophilic portion is made up of the long hydrocarbon chain from the fatty acid. In other words, whereas normally oil and water do not mix, the addition of soap allows oils to disperse in water and be rinsed away. Synthetic detergents operate by similar mechanisms to soap. Effect of the alkali The type of alkali metal used determines the kind of soap produced. Sodium soaps, prepared from sodium hydroxide, are firm, whereas potassium soaps, derived from potassium hydroxide, are softer or often liquid. Historically, potassium hydroxide was extracted from the ashes of bracken or other plants. Lithium soaps also tend to be hard—these are used exclusively in greases. Effects of fats Soaps are derivatives of fatty acids. Traditionally they have been made from triglycerides (oils and fats). [4] Triglyceride is the chemical name for the triesters of fatty acids and glycerin. Tallow, i.e., rendered beef fat, is the most available triglyceride from animals. Its saponified product is called sodium tallowate. Typical vegetable oils used in soap making are palm oil, coconut oil, olive oil, and laurel oil. Each species offers quite different fatty acid content and, hence, results in soaps of distinct feel. The seed oils give softer but milder soaps. Soap made from pure olive oil is sometimes called Castile soap or Marseille soap and is reputed for being extra-mild. The term "Castile" is also sometimes applied to soaps from a mixture of oils, but a high percentage of olive oil. Fatty acid content of various fats used for soap-making Lauric acid Myristic acid Palmitic acid Stearic acid Oleic acid Linoleic acid Linolenic acid fats C 12 , saturated C 14 saturated C 16 saturated C 18 saturated C 18 monounsaturated C 18 diunsaturated C 18 triunsaturated Tallow 0 4 28 23 35 2 1 Coconut oil 48 18 9 3 7 2 0 Palm kernel oil 46 16 8 3 12 2 0 Laurel oil 54 0 0 0 15 17 0 Olive oil 0 0 11 2 78 10 0 Canola 0 1 3 2 58 9 23 |+
  7. 7. Soap 3 History of cleansing soaps Early history Box for Amigo de Obrero (Worker's friend) soap from 20th century. Part of the Museo del Objeto del Objeto collection The earliest recorded evidence of the production of soap-like materials dates back to around 2800 BC in Ancient Babylon. [5] In the reign of Nabonidus (556–539 BCE) a recipe for soap consisted of uhulu [ashes], cypress [oil] and sesame [seed oil] "for washing the stones for the servant girls". [6] A formula for soap consisting of water, alkali, and cassia oil was written on a Babylonian clay tablet around 2200 BC. The Ebers papyrus (Egypt, 1550 BC) indicates that ancient Egyptians bathed regularly and combined animal and vegetable oils with alkaline salts to create a soap-like substance. Egyptian documents mention that a soap-like substance was used in the preparation of wool for weaving. Roman history The word sapo, Latin for soap, first appears in Pliny the Elder's Historia Naturalis, which discusses the manufacture of soap from tallow and ashes, but the only use he mentions for it is as a pomade for hair; he mentions rather disapprovingly that the men of the Gauls and Germans were more likely to use it than their female counterparts. [7] Aretaeus of Cappadocia, writing in the first century AD, observes among "Celts, which are men called Gauls, those alkaline substances that are made into balls, called soap". [8] A popular belief encountered in some places claims that soap takes its name from a supposed Mount Sapo, where animal sacrifices were supposed to take place—tallow from these sacrifices would then have mixed with ashes from fires associated with these sacrifices and with water to produce soap. But there is no evidence of a Mount Sapo within the Roman world and no evidence for the apocryphal story. The Latin word sapo simply means "soap"; it was likely borrowed from an early Germanic language and is cognate with Latin sebum, "tallow", which appears in Pliny the Elder's account. [9] Roman animal sacrifices usually burned only the bones and inedible entrails of the sacrificed animals; edible meat and fat from the sacrifices were taken by the humans rather than the gods. Zosimos of Panopolis, ca. 300 AD, describes soap and soapmaking. [10] Galen describes soap-making using lye and prescribes washing to carry away impurities from the body and clothes. According to Galen, the best soaps were Germanic, and soaps from Gaul were second best. This is a reference to true soap in antiquity. [10] Islamic history A 12th century Islamic document has the world's first extant description of the process of soap production. [11] It mentions the key ingredient, alkali, which later becomes crucial to modern chemistry, derived from al-qaly or "ashes". By the thirteenth century the manufacture of soap in the Islamic world had become virtually industrialized, with sources in Fes, Damascus, and Aleppo. Medieval history Soap-makers in Naples were members of a guild in the late sixth century, [12] and in the 8th century, soap-making was well known in Italy and Spain. [13] The Carolingian capitulary De Villis, dating to around 800, representing the royal will of Charlemagne, mentions soap as being one of the products the stewards of royal estates are to tally. Soap-making is mentioned both as "women's work" and as the produce of "good workmen" alongside other necessities such as the produce of carpenters, blacksmiths, and bakers. [14]
  8. 8. Soap 4 15th–20th centuries Ad for Pear' Soap, 1889 1922 magazine advertisement for Palmolive Soap. In France, by the second half of the 15th century, the semi-industrialized professional manufacture of soap was concentrated in a few centers of Provence— Toulon, Hyères, and Marseille — which supplied the rest of France. [15] In Marseilles, by 1525, production was concentrated in at least two factories, and soap production at Marseille tended to eclipse the other Provençal centers. [16] English manufacture tended to concentrate in London. [17] Finer soaps were later produced in Europe from the 16th century, using vegetable oils (such as olive oil) as opposed to animal fats. Many of these soaps are still produced, both industrially and by small-scale artisans. Castile soap is a popular example of the vegetable-only soaps derived by the oldest "white soap" of Italy. In modern times, the use of soap has become universal in industrialized nations due to a better understanding of the role of hygiene in reducing the population size of pathogenic microorganisms. Industrially manufactured bar soaps first became available in the late eighteenth century, as advertising campaigns in Europe and the United States promoted popular awareness of the relationship between cleanliness and health. [18] Until the Industrial Revolution, soapmaking was conducted on a small scale and the product was rough. Andrew Pears started making a high-quality, transparent soap in 1789 in London. His son-in-law, Thomas J. Barratt, opened a factory in Isleworth in 1862. William Gossage produced low-price good-quality soap from the 1850s. Robert Spear Hudson began manufacturing a soap powder in 1837, initially by grinding the soap with a mortar and pestle. American manufacturer Benjamin T. Babbitt introduced marketing innovations that included sale of bar soap and distribution of product samples. William Hesketh Lever and his brother, James, bought a small soap works in Warrington in 1886 and founded what is still one of the largest soap businesses, formerly called Lever Brothers and now called Unilever. These soap businesses were among the first to employ large-scale advertising campaigns. Soap-making processes The industrial production of soap involves continuous processes, involving continuous addition of fat and removal of product. Smaller-scale production involve the traditional batch processes. There are three variations: the cold-process, wherein the reaction takes place substantially at room temperature, the semi-boiled or hot-process, wherein the reaction takes place at near-boiling point, and the fully boiled process, wherein the reactants are boiled at least once and the
  9. 9. Soap 5 Liquid soap Manufacturing process of soaps/detergents glycerol recovered. The cold-process and hot-process (semi-boiled) are the simplest and typically used by small artisans and hobbyists producing handmade decorative soaps and similar. The glycerine remains in the soap and the reaction continues for many days after the soap is poured into moulds. The glycerine is left during the hot-process method, but at the high temperature employed the reaction is practically completed in the kettle, before the soap is poured into moulds. This process is simple and quick and is the one employed in small factories all over the world. Handmade soap from the cold process also differs from industrially made soap in that an excess of fat is used, beyond that which is used to consume the alkali (in a cold-pour process this excess fat is called "superfatting"), and the glycerine left in acts as a moisturizing agent. However, the glycerine also makes the soap softer and less resistant to becoming "mushy" if left wet. Since it is better to add too much oil and have left-over fat, than to add too much lye and have left-over lye, soap produced from the hot process also contains left-over glycerine and its concomitant pros and cons. Further addition of glycerine and processing of this soap produces glycerin soap. Superfatted soap is more skin-friendly than one without extra fat. However, if too much fat is added, it can leave a "greasy" feel to the skin. Sometimes an emollient additive such as jojoba oil or shea butter is added "at trace" (i.e., the point at which the saponification process is sufficiently advanced that the soap has begun to thicken in the cold process method) in the belief that nearly all the lye will be spent and it will escape saponification and remain intact. In the case of hot-process soap, an emollient may be added after the initial oils have saponified so that they remain unreacted in the finished soap. Superfatting can also be accomplished through a process known as "lye discount" in which the soap maker uses less alkali than required instead of adding extra fats. Cold process Even in the cold-soapmaking process, some heat is usually required; the temperature is usually raised to a point sufficient to ensure complete melting of the fat being used. The batch may also be kept warm for some time after mixing to ensure that the alkali (hydroxide) is completely used up. This soap is safe to use after approximately 12–48 hours but is not at its peak quality for use for several weeks. Cold-process soapmaking requires exact measurements of lye and fat amounts and computing their ratio, using saponification charts to ensure that the finished product does not contain any excess hydroxide or too much free unreacted fat. Saponification charts should also be used in hot-processes, but are not necessary for the "fully boiled hot-process" soaping. A cold-process soapmaker first looks up the saponification value of the fats being used on a saponification chart. This value is used to calculate the appropriate amount of lye. Excess unreacted lye in the soap will result in a very high pH and can burn or irritate skin; not enough lye and the soap is greasy. Most soap makers formulate their recipes with a 4–10% deficit of lye so that all of the lye is converted and that excess fat is left for skin conditioning benefits. The lye is dissolved in water. Then oils are heated, or melted if they are solid at room temperature. Once the oils are liquefied and the lye is fully dissolved in water, they are combined. This lye-fat mixture is mixed until the two phases (oils and water) are fully emulsified. Emulsification is most easily identified visually when the soap exhibits
  10. 10. Soap 6 some level of "trace", which is the thickening of the mixture. (Modern-day amateur soapmakers often use a stick blender to speed this process). There are varying levels of trace. Depending on how additives will affect trace, they may be added at light trace, medium trace, or heavy trace. After much stirring, the mixture turns to the consistency of a thin pudding. "Trace" corresponds roughly to viscosity. Essential oils and fragrance oils can be added with the initial soaping oils, but solid additives such as botanicals, herbs, oatmeal, or other additives are most commonly added at light trace, just as the mixture starts to thicken. Handmade soaps sold at a shop in Hyères, France Traditional Marseille soap The batch is then poured into moulds, kept warm with towels or blankets, and left to continue saponification for 12 to 48 hours. (Milk soaps or other soaps with sugars added are the exception. They typically do not require insulation, as the presence of sugar increases the speed of the reaction and thus the production of heat.) During this time, it is normal for the soap to go through a "gel phase", wherein the opaque soap will turn somewhat transparent for several hours, before once again turning opaque. After the insulation period, the soap is firm enough to be removed from the mould and cut into bars. At this time, it is safe to use the soap, since saponification is in essence complete. However, cold-process soaps are typically cured and hardened on a drying rack for 2–6 weeks before use. During this cure period, trace amounts of residual lye are consumed by saponification and excess water evaporates. During the curing process, some molecules in the outer layer of the solid soap react with the carbon dioxide of the air and produce a dusty sheet of sodium carbonate. This reaction is more intense if the mass is exposed to wind or low temperatures. Hot processes Hot-processed soaps are created by encouraging the saponification reaction by adding heat to the reaction. This speeds the reaction. Unlike cold-processed soap, in hot-process soaping the oils are completely saponified by the end of the handling period, whereas with cold-pour soap the bulk of the saponification happens after the oils and lye solution emulsification is poured into moulds. In the hot process, the hydroxide and the fat are heated and mixed together at 80–100 °C, a little below boiling point, until saponification is complete, which, before modern scientific equipment, the soapmaker determined by taste (the sharp, distinctive taste of the hydroxide disappears after it is saponified) or by eye; the experienced eye can tell when gel stage and full saponification has occurred. Beginners can find this information through research and classes. Tasting soap for readiness is not recommended, as sodium and potassium hydroxides, when not saponified, are highly caustic. An advantage of the fully boiled hot process in soap making is that the exact amount of hydroxide required need not be known with great accuracy. They originated when the purity of the alkali hydroxides were unreliable, as these processes can use even naturally found alkalis such as wood ashes and potash deposits. In the fully boiled process, the mix is actually boiled (100 °C+), and, after saponification has occurred, the "neat soap" is precipitated from the solution by adding common salt, and the excess liquid drained off. This excess liquid carries away with it much of the impurities and color compounds in the fat, to leave a purer, whiter soap, and with practically all the glycerine removed. The hot, soft soap is then pumped into a mould. The spent hydroxide solution is processed for recovery of glycerine.
  11. 11. Soap 7 Molds Many commercially available soap moulds are made of silicone or various types of plastic, although many soap-making hobbyists may use cardboard boxes lined with a plastic film. Soaps can be made in long bars that are cut into individual portions, or cast into individual moulds. Purification and finishing A generic bar of soap, after purification and finishing In the fully boiled process on factory scale, the soap is further purified to remove any excess sodium hydroxide, glycerol, and other impurities, colour compounds, etc. These components are removed by boiling the crude soap curds in water and then precipitating the soap with salt. At this stage, the soap still contains too much water, which has to be removed. This was traditionally done on chill rolls, which produced the soap flakes commonly used in the 1940s and 1950s. This process was superseded by spray dryers and then by vacuum dryers. The dry soap (approximately 6–12% moisture) is then compacted into small pellets or noodles. These pellets or noodles are then ready for soap finishing, the process of converting raw soap pellets into a saleable product, usually bars. Soap pellets are combined with fragrances and other materials and blended to homogeneity in an amalgamator (mixer). The mass is then discharged from the mixer into a refiner, which, by means of an auger, forces the soap through a fine wire screen. From the refiner, the soap passes over a roller mill (French milling or hard milling) in a manner similar to calendering paper or plastic or to making chocolate liquor. The soap is then passed through one or more additional refiners to further plasticize the soap mass. Immediately before extrusion, the mass is passed through a vacuum chamber to remove any trapped air. It is then extruded into a long log or blank, cut to convenient lengths, passed through a metal detector, and then stamped into shape in refrigerated tools. The pressed bars are packaged in many ways. (Azul e branco soap) – A bar of blue-white soap Sand or pumice may be added to produce a scouring soap. The scouring agents serve to remove dead skin cells from the surface being cleaned. This process is called exfoliation. Many newer materials that are effective but do not have the sharp edges and poor particle size distribution of pumice are used for exfoliating soaps. Nanoscopic metals are commonly added to certain soaps specifically for both colouration and anti-bacterial properties. Titanium powder is commonly used in extreme "white" soaps for these purposes; nickel, aluminium, and silver are less commonly used. These metals exhibit an electron-robbing behaviour when in contact with bacteria, stripping electrons from the organism's surface, thereby disrupting their functioning and killing them. Because some of the metal is left behind on the skin and in the pores, the benefit can also extend beyond the actual time of washing, helping reduce bacterial contamination and reducing potential odours from bacteria on the skin surface.
  12. 12. Soap 8 References [1] IUPAC. " IUPAC Gold Book – soap (http://goldbook.iupac.org/S05721.html)" Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. doi:10.1351/goldbook. Accessed 2010-08-09 [2] Cavitch, Susan Miller. The Natural Soap Book. Storey Publishing, 1994 ISBN 0-88266-888-9. [3] Thorsten Bartels et al. "Lubricants and Lubrication" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Weinheim. doi:10.1002/14356007.a15_423 [4] David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2 [5] Willcox, Michael (2000). "Soap" (http://books.google.com/books?id=4HI8dGHgeIQC&pg=PA453). In Hilda Butler. Poucher's Perfumes, Cosmetics and Soaps (10th ed.). Dordrecht: Kluwer Academic Publishers. p. 453. ISBN 0-7514-0479-9. . "The earliest recorded evidence of the production of soap-like materials dates back to around 2800 BCE in ancient Babylon." [6] Noted in Martin Levey (1958). "Gypsum, salt and soda in ancient Mesopotamian chemical technology". Isis 49 (3): 336–342 (341). doi:10.1086/348678. JSTOR 226942. [7] Pliny the Elder, Natural History, XXVIII.191 (http://penelope.uchicago.edu/Thayer/L/Roman/Texts/Pliny_the_Elder/28*.html#191). [8] Aretaeus, The Extant Works of Aretaeus, the Cappadocian, ed. and tr. Francis Adams (London) 1856:494 note 6, noted in Michael W. Dols, "Leprosy in medieval Arabic medicine" Journal of the History of Medicine 1979:316 note 9; the Gauls with whom the Cappadocian would have been familiar are those of Anatolian Galatia. [9] soap (http://www.etymonline.com/index.php?term=soap). Etymonline.com. Retrieved on 2011-11-20. [10] Partington, James Riddick; Bert S Hall (1999). A History of Greek Fire and Gun Powder. JHU Press. p. 307. ISBN 0-8018-5954-9. [11] BBC Science and Islam Part 2, Jim Al-Khalili. BBC Productions. Accessed 30 January 2012. [12] footnote 48, p. 104, Understanding the Middle Ages: the transformation of ideas and attitudes in the Medieval world, Harald Kleinschmidt, illustrated, revised, reprint edition, Boydell & Brewer, 2000, ISBN 0-85115-770-X. [13] Anionic and Related Lime Soap Dispersants, Raymond G. Bistline, Jr., in Anionic surfactants: organic chemistry, Helmut Stache, ed., Volume 56 of Surfactant science series, CRC Press, 1996, chapter 11, p. 632, ISBN 0-8247-9394-3. [14] Robinson, James Harvey (1904). Readings in European History: Vol. I (http://www.fordham.edu/halsall/source/carol-devillis.html). Ginn and co. . [15] John U. Nef (1936). "A Comparison of Industrial Growth in France and England from 1540 to 1640: III". The Journal of Political Economy 44 (5): 643–666 (660ff.). doi:10.1086/254976. JSTOR 1824135. [16][16] L. Barthélemy, "La savonnerie marseillaise", 1883, noted by Nef 1936:660 note 99. [17][17] Nef 1936:653, 660. [18] McNeil, Ian (1990). An Encyclopaedia of the history of technology (http://books.google.com/books?id=uxsOAAAAQAAJ&pg=PA203). Taylor & Francis. pp. 2003–205. ISBN 978-0-415-01306-2. . Further reading • Garzena, Patrizia-Tadiello, Marina (2004). Soap Naturally—Ingredients, methods and recipes for natural handmade soap. Online information and Table of Contents (http://www.soap-naturally.com/). ISBN 978-0-9756764-0-0 • Thomssen, E. G., Ph. D. (1922). Soap-Making Manual (http://www.gutenberg.org/ebooks/34114) Free ebook at Project Gutenberg •• Mohr, Merilyn (1979). "The Art of Soap Making". A Harrowsmith Contemporary Primer. Firefly Books. ISBN 978-0-920656-03-7 •• Dunn, Kevin M. (2010) " Scientific Soapmaking: The Chemistry of Cold Process" Clavicula Press. ISBN 978-1-935652-09-0
  13. 13. Soap 9 External links • Handmade soapmaking information, resources and mailing list (http://www.natural-soapmaking.net/) • Soap History (http://www.cleaninginstitute.org/clean_living/soaps__detergent_history.aspx) American Cleaning Institute (formerly The Soap and Detergent Association) • A short history of soap (http://www.pharmj.com/Editorial/19991218/articles/soap.html) The Pharmaceutical Journal • Medieval Sourcebook: The Capitulary De Villis (http://www.fordham.edu/halsall/source/carol-devillis.html) • How to Make Soap (http://candleandsoap.about.com/od/soapmakingbasics/a/How-To-Make-Soap.htm) • Soap (http://www.elmhurst.edu/~chm/vchembook/554soap.html)
  14. 14. 10 Chemistry and soapmaking Amphiphile Phospholipids have amphipathic character. Amphiphile (from the Greek αμφις, amphis: both and φιλíα, philia: love, friendship) is a term describing a chemical compound possessing both hydrophilic (water-loving, polar) and lipophilic (fat-loving) properties. Such a compound is called amphiphilic or amphipathic. This forms the basis for a number of areas of research in chemistry and biochemistry, notably that of lipid polymorphism. Organic compounds containing hydrophilic groups at both ends of a prolate molecule are called bolaamphiphilic. Common amphiphilic substances are soaps and detergents. Structure and Properties The lipophilic group is typically a large hydrocarbon moiety, such as a long chain of the form CH 3 (CH 2 ) n , with n > 4. The hydrophilic group falls into one of the following categories: 1.1. Charged groups • Anionic. Examples, with the lipophilic part of the molecule represented by an R, are: • carboxylates: RCO 2 − ; • sulfates: RSO 4 − ; • sulfonates: RSO 3 − . • phosphates: The charged functionality in phospholipids. • Cationic. Examples: • amines: RNH 3 + . 2. Polar, uncharged groups. Examples are alcohols with large R groups, such as diacyl glycerol (DAG), and oligoethyleneglycols with long alkyl chains. Often, amphiphilic species have several lipophilic parts, several hydrophilic parts, or several of both. Proteins and some block copolymers are such examples. Amphiphilic compounds have lipophilic (typically hydrocarbon) structures and hydrophilic polar functional groups (either ionic or uncharged). As a result of having both lipophilic and hydrophilic portions, some amphiphilic compounds may dissolve in water and to some extent in non-polar organic solvents. When placed in an immiscible biphasic system consisting of aqueous and organic solvent the amphiphilic compound will partition the two phases. The extent of the hydrophobic and hydrophilic portions determines the extent of partitioning.
  15. 15. Amphiphile 11 Biological role Phospholipids, a class of amphiphilic molecules, are the main components of biological membranes. The amphiphilic nature of these molecules defines the way in which they form membranes. They arrange themselves into bilayers, by positioning their polar groups towards the surrounding aqueous medium, and their lipophilic chains towards the inside of the bilayer, defining a non-polar region between two polar ones. Although phospholipids are principal constituents of biological membranes, there are other amphiphilic molecules, such as cholesterol and glycolipids, which are also included in these structures and give them different physical and biological properties. Many other amphiphilic compounds, such as pepducins, strongly interact with biological membranes by insertion of hydrophobic part into the lipid membrane, while exposing the hydrophilic part to the aqueous medium, altering their physical behavior and sometimes disrupting them. Examples of amphiphiles There are several examples of molecules that present amphiphilic properties: Hydrocarbon based surfactants are an example group of amphiphilic compounds. Their polar region can be either ionic, or non-ionic. Some typical members of this group are: sodium dodecyl sulfate (anionic), Benzalkonium chloride (cationic), Cocamidopropyl betaine (zwitterionic) and octanol (long chain alcohol, non-ionic). Many biological compounds are amphiphilic: phospholipids, cholesterol, glycolipids, fatty acids, bile acids, saponins, local anaesthetics etc. External links • Estimating intestinal permeability by surface activity profiling [1] References [1] http://www.kibron.com/drug-discovery/physicochemical-profiling/study-on-fraction-absorbed/
  16. 16. Fatty acid 12 Fatty acid Butyric acid, a short-chain fatty acid In chemistry, especially biochemistry, a fatty acid is a carboxylic acid with a long aliphatic tail (chain), which is either saturated or unsaturated. Most naturally occurring fatty acids have a chain of an even number of carbon atoms, from 4 to 28. [1] Fatty acids are usually derived from triglycerides or phospholipids. When they are not attached to other molecules, they are known as "free" fatty acids. Fatty acids are important sources of fuel because, when metabolized, they yield large quantities of ATP. Many cell types can use either glucose or fatty acids for this purpose. In particular, heart and skeletal muscle prefer fatty acids. The brain cannot use fatty acids as a source of fuel; it relies on glucose or ketone bodies. [2] Types of fatty acids Three dimensional representations of several fatty acids Fatty acids that have double bonds are known as unsaturated. Fatty acids without double bonds are known as saturated. They differ in length as well. Length of free fatty acid chains Fatty acid chains differ by length, often categorized as short, medium, or long. • Short-chain fatty acids (SCFA) are fatty acids with aliphatic tails of fewer than six carbons (i.e. butyric acid). • Medium-chain fatty acids (MCFA) are fatty acids with aliphatic tails of 6–12 [3] carbons, which can form medium-chain triglycerides. • Long-chain fatty acids (LCFA) are fatty acids with aliphatic tails longer than 12 carbons. [4] • Very long chain fatty acids (VLCFA) are fatty acids with aliphatic tails longer than 22 carbons
  17. 17. Fatty acid 13 Unsaturated fatty acids Comparison of the trans isomer (top) Elaidic acid and the cis-isomer oleic acid. Unsaturated fatty acids have one or more double bonds between carbon atoms. (Pairs of carbon atoms connected by double bonds can be saturated by adding hydrogen atoms to them, converting the double bonds to single bonds. Therefore, the double bonds are called unsaturated.) The two carbon atoms in the chain that are bound next to either side of the double bond can occur in a cis or trans configuration. cis A cis configuration means that adjacent hydrogen atoms are on the same side of the double bond. The rigidity of the double bond freezes its conformation and, in the case of the cis isomer, causes the chain to bend and restricts the conformational freedom of the fatty acid. The more double bonds the chain has in the cis configuration, the less flexibility it has. When a chain has many cis bonds, it becomes quite curved in its most accessible conformations. For example, oleic acid, with one double bond, has a "kink" in it, whereas linoleic acid, with two double bonds, has a more pronounced bend. Alpha-linolenic acid, with three double bonds, favors a hooked shape. The effect of this is that, in restricted environments, such as when fatty acids are part of a phospholipid in a lipid bilayer, or triglycerides in lipid droplets, cis bonds limit the ability of fatty acids to be closely packed, and therefore could affect the melting temperature of the membrane or of the fat. trans A trans configuration, by contrast, means that the next two hydrogen atoms are bound to opposite sides of the double bond. As a result, they do not cause the chain to bend much, and their shape is similar to straight saturated fatty acids. In most naturally occurring unsaturated fatty acids, each double bond has three n carbon atoms after it, for some n, and all are cis bonds. Most fatty acids in the trans configuration (trans fats) are not found in nature and are the result of human processing (e.g., hydrogenation). The differences in geometry between the various types of unsaturated fatty acids, as well as between saturated and unsaturated fatty acids, play an important role in biological processes, and in the construction of biological structures (such as cell membranes).
  18. 18. Fatty acid 14 Examples of Unsaturated Fatty Acids Common name Chemical structure Δ x C:D n−x Myristoleic acid CH3 (CH2 )3 CH=CH(CH2 )7 COOH cis-Δ 9 14:1 n−5 Palmitoleic acid CH3 (CH2 )5 CH=CH(CH2 )7 COOH cis-Δ 9 16:1 n−7 Sapienic acid CH3 (CH2 )8 CH=CH(CH2 )4 COOH cis-Δ 6 16:1 n−10 Oleic acid CH3 (CH2 )7 CH=CH(CH2 )7 COOH cis-Δ 9 18:1 n−9 Elaidic acid CH3 (CH2 )7 CH=CH(CH2 )7 COOH trans-Δ 9 18:1 n−9 Vaccenic acid CH3 (CH2 )5 CH=CH(CH2 )9 COOH trans-Δ 11 18:1 n−7 Linoleic acid CH 3 (CH 2 ) 4 CH=CHCH 2 CH=CH(CH 2 ) 7 COOH cis,cis-Δ 9 ,Δ 12 18:2 n−6 Linoelaidic acid CH 3 (CH 2 ) 4 CH=CHCH 2 CH=CH(CH 2 ) 7 COOH trans,trans-Δ 9 ,Δ 12 18:2 n−6 α-Linolenic acid CH 3 CH 2 CH=CHCH 2 CH=CHCH 2 CH=CH(CH 2 ) 7 COOH cis,cis,cis-Δ 9 ,Δ 12 ,Δ 15 18:3 n−3 Arachidonic acid CH 3 (CH 2 ) 4 CH=CHCH 2 CH=CHCH 2 CH=CHCH 2 CH=CH(CH 2 ) 3 COOH NIST [5] cis,cis,cis,cis-Δ 5 Δ 8 ,Δ 11 ,Δ 14 20:4 n−6 Eicosapentaenoic acid CH 3 CH 2 CH=CHCH 2 CH=CHCH 2 CH=CHCH 2 CH=CHCH 2 CH=CH(CH 2 ) 3 COOH cis,cis,cis,cis,cis-Δ 5 ,Δ 8 ,Δ 11 ,Δ 14 ,Δ 17 20:5 n−3 Erucic acid CH 3 (CH 2 ) 7 CH=CH(CH 2 ) 11 COOH cis-Δ 13 22:1 n−9 Docosahexaenoic acid CH 3 CH 2 CH=CHCH 2 CH=CHCH 2 CH=CHCH 2 CH=CHCH 2 CH=CHCH 2 CH=CH(CH 2 ) 2 COOH cis,cis,cis,cis,cis,cis-Δ 4 ,Δ 7 ,Δ 10 ,Δ 13 ,Δ 16 ,Δ 19 22:6 n−3 Essential fatty acids Fatty acids that are required by the human body but cannot be made in sufficient quantity from other substrates, and therefore must be obtained from food, are called essential fatty acids. There are two series of essential fatty acids: one has a double bond three carbon atoms removed from the methyl end; the other has a double bond six carbon atoms removed from the methyl end. Humans lack the ability to introduce double bonds in fatty acids beyond carbons 9 and 10, as counted from the carboxylic acid side. [6] Two essential fatty acids are linoleic acid (LA) and alpha-linolenic acid (ALA). They are widely distributed in plant oils. The human body has a limited ability to convert ALA into the longer-chain n-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), which can also be obtained from fish.
  19. 19. Fatty acid 15 Saturated fatty acids Saturated fatty acids are long-chain carboxylic acids that usually have between 12 and 24 carbon atoms and have no double bonds. Thus, saturated fatty acids are saturated with hydrogen (since double bonds reduce the number of hydrogens on each carbon). Because saturated fatty acids have only single bonds, each carbon atom within the chain has 2 hydrogen atoms (except for the omega carbon at the end that has 3 hydrogens). Examples of Saturated Fatty Acids Common name Chemical structure C:D Caprylic acid CH 3 (CH 2 ) 6 COOH 8:0 Capric acid CH 3 (CH 2 ) 8 COOH 10:0 Lauric acid CH 3 (CH 2 ) 10 COOH 12:0 Myristic acid CH 3 (CH 2 ) 12 COOH 14:0 Palmitic acid CH 3 (CH 2 ) 14 COOH 16:0 Stearic acid CH 3 (CH 2 ) 16 COOH 18:0 Arachidic acid CH 3 (CH 2 ) 18 COOH 20:0 Behenic acid CH 3 (CH 2 ) 20 COOH 22:0 Lignoceric acid CH 3 (CH 2 ) 22 COOH 24:0 Cerotic acid CH 3 (CH 2 ) 24 COOH 26:0 Nomenclature Numbering of carbon atoms Several different systems of nomenclature are used for fatty acids. The following table describes the most common systems. System Example Explanation Trivial nomenclature Palmitoleic acid Trivial names (or common names) are non-systematic historical names, which are the most frequent naming system used in literature. Most common fatty acids have trivial names in addition to their systematic names (see below). These names frequently do not follow any pattern, but they are concise and often unambiguous. Systematic nomenclature (9Z)-octadecenoic acid Systematic names (or IUPAC names) derive from the standard IUPAC Rules for the Nomenclature of Organic Chemistry, published in 1979, [7] along with a recommendation published specifically for lipids in 1977. [8] Counting begins from the carboxylic acid end. Double bonds are labelled with cis-/trans- notation or E-/Z- notation, where appropriate. This notation is generally more verbose than common nomenclature, but has the advantage of being more technically clear and descriptive. Δ x nomenclature cis,cis-Δ 9 ,Δ 12 octadecadienoic acid In Δ x (or delta-x) nomenclature, each double bond is indicated by Δ x , where the double bond is located on the xth carbon–carbon bond, counting from the carboxylic acid end. Each double bond is preceded by a cis- or trans- prefix, indicating the conformation of the molecule around the bond. For example, linoleic acid is designated "cis-Δ 9 , cis-Δ 12 octadecadienoic acid". This nomenclature has the advantage of being less verbose than systematic nomenclature, but is no more technically clear or descriptive.
  20. 20. Fatty acid 16 n−x nomenclature n−3 n−x (n minus x; also ω−x or omega-x) nomenclature both provides names for individual compounds and classifies them by their likely biosynthetic properties in animals. A double bond is located on the x th carbon–carbon bond, counting from the terminal methyl carbon (designated as n or ω) toward the carbonyl carbon. For example, α-Linolenic acid is classified as a n−3 or omega-3 fatty acid, and so it is likely to share a biosynthetic pathway with other compounds of this type. The ω−x, omega-x, or "omega" notation is common in popular nutritional literature, but IUPAC has deprecated it in favor of n−x notation in technical documents. [7] The most commonly researched fatty acid biosynthetic pathways are n−3 and n−6, which are hypothesized to decrease or increase, respectively, inflammation. Lipid numbers 18:3 18:3, n−6 18:3, cis,cis,cis-Δ 9 ,Δ 12 ,Δ 15 Lipid numbers take the form C:D, where C is the number of carbon atoms in the fatty acid and D is the number of double bonds in the fatty acid. This notation can be ambiguous, as some different fatty acids can have the same numbers. Consequently, when ambiguity exists this notation is usually paired with either a Δ x or n−x term. [7] Production Fatty acids are usually produced industrially by the hydrolysis of triglycerides, with the removal of glycerol (see oleochemicals). Phospholipids represent another source. Some fatty acids are produced synthetically by hydrocarboxylation of alkenes. Free fatty acids The biosynthesis of fatty acids involves the condensation of acetyl-CoA. Since this coenzyme carries a two-carbon-atom group, almost all natural fatty acids have even numbers of carbon atoms. The "uncombined fatty acids" or "free fatty acids" found in organisms come from the breakdown of a triglyceride. Because they are insoluble in water, these fatty acids are transported (solubilized, circulated) while bound to plasma protein albumin. The levels of "free fatty acid" in the blood are limited by the availability of albumin binding sites. Fatty acids in dietary fats The following table gives the fatty acid, vitamin E and cholesterol composition of some common dietary fats. [9] [10] Saturated Monounsaturated Polyunsaturated Cholesterol Vitamin E g/100g g/100g g/100g mg/100g mg/100g Animal fats Lard 40.8 43.8 9.6 93 0.00 Duck fat [11] 33.2 49.3 12.9 100 2.70 Butter 54.0 19.8 2.6 230 2.00 Vegetable fats Coconut oil 85.2 6.6 1.7 0 .66 Palm oil 45.3 41.6 8.3 0 33.12 Cottonseed oil 25.5 21.3 48.1 0 42.77 Wheat germ oil 18.8 15.9 60.7 0 136.65 Soya oil 14.5 23.2 56.5 0 16.29 Olive oil 14.0 69.7 11.2 0 5.10 Corn oil 12.7 24.7 57.8 0 17.24 Sunflower oil 11.9 20.2 63.0 0 49.0
  21. 21. Fatty acid 17 Safflower oil 10.2 12.6 72.1 0 40.68 Hemp oil 10 15 75 0 Canola/Rapeseed oil 5.3 64.3 24.8 0 22.21 Reactions of fatty acids Fatty acids exhibit reactions like other carboxylic acid, i.e. they undergo esterification and acid-base reactions. Acidity Fatty acids do not show a great variation in their acidities, as indicated by their respective pK a . Nonanoic acid, for example, has a pK a of 4.96, being only slightly weaker than acetic acid (4.76). As the chain length increases, the solubility of the fatty acids in water decreases very rapidly, so that the longer-chain fatty acids have minimal effect on the pH of an aqueous solution. Even those fatty acids that are insoluble in water will dissolve in warm ethanol, and can be titrated with sodium hydroxide solution using phenolphthalein as an indicator to a pale-pink endpoint. This analysis is used to determine the free fatty acid content of fats; i.e., the proportion of the triglycerides that have been hydrolyzed. Hydrogenation and hardening Hydrogenation of unsaturated fatty acids is widely practiced to give saturated fatty acids, which are less prone toward rancidification. Since the saturated fatty acids are higher melting than the unsaturated relatives, the process is called hardening. This technology is used to convert vegetable oils into margarine. During partial hydrogenation, unsaturated fatty acids can be isomerized from cis to trans configuration. [12] More forcing hydrogenation, i.e. using higher pressures of H 2 and higher temperatures, converts fatty acids into fatty alcohols. Fatty alcohols are, however, more easily produced from fatty acid esters. In the Varrentrapp reaction certain unsaturated fatty acids are cleaved in molten alkali, a reaction at one time of relevance to structure elucidation. Auto-oxidation and rancidity Unsaturated fatty acids undergo a chemical change known as auto-oxidation. The process requires oxygen (air) and is accelerated by the presence of trace metals. Vegetable oils resists this process because they contain antioxidants, such as tocopherol. Fats and oils often are treated with chelating agents such as citric acid to remove the metal catalysts. Ozonolysis Unsaturated fatty acids are susceptible to degradation by ozone. This reaction is practiced in the production of azelaic acid ((CH 2 ) 7 (CO 2H ) 2 ) from oleic acid. [12] Circulation Digestion and intake Short- and medium-chain fatty acids are absorbed directly into the blood via intestine capillaries and travel through the portal vein just as other absorbed nutrients do. However, long-chain fatty acids are not directly released into the intestinal capillaries. Instead they are absorbed into the fatty walls of the intestine villi and reassembled again into triglycerides. The triglycerides are coated with cholesterol and protein (protein coat) into a compound called a chylomicron.
  22. 22. Fatty acid 18 Within the villi, the chylomicron enters a lymphatic capillary called a lacteal, which merges into larger lymphatic vessels. It is transported via the lymphatic system and the thoracic duct up to a location near the heart (where the arteries and veins are larger). The thoracic duct empties the chylomicrons into the bloodstream via the left subclavian vein. At this point the chylomicrons can transport the triglycerides to tissues where they are stored or metabolized for energy. Metabolism Fatty acids (provided either by ingestion or by drawing on triglycerides stored in fatty tissues) are distributed to cells to serve as a fuel for muscular contraction and general metabolism. They are consumed by mitochondria to produce ATP through beta oxidation. Distribution Blood fatty acids are in different forms in different stages in the blood circulation. They are taken in through the intestine in chylomicrons, but also exist in very low density lipoproteins (VLDL) and low density lipoproteins (LDL) after processing in the liver. In addition, when released from adipocytes, fatty acids exist in the blood as free fatty acids. It is proposed that the blend of fatty acids exuded by mammalian skin, together with lactic acid and pyruvic acid, is distinctive and enables animals with a keen sense of smell to differentiate individuals. [13] References [1] IUPAC Compendium of Chemical Terminology (http://goldbook.iupac.org/F02330.html) (2nd ed.). International Union of Pure and Applied Chemistry. 1997. ISBN 0-521-51150-X. . Retrieved 2007-10-31. [2] Mary K. Campbell, Shawn O. Farrell (2006). Biochemistry (5th ed.). Cengage Learning. p. 579. ISBN 0-534-40521-5. [3] Medscape: Free CME, Medical News, Full-text Journal Articles & More (http://emedicine.medscape.com/article/946755-overview) [4] Christopher Beermann1, J Jelinek1, T Reinecker2, A Hauenschild2, G Boehm1, and H-U Klör2, " Short term effects of dietary medium-chain fatty acids and n-3 long-chain polyunsaturated fatty acids on the fat metabolism of healthy volunteers (http://lipidworld.com/content/2/1/ 10)" [5] http://webbook.nist.gov/cgi/cbook.cgi?Name=Arachidonic+Acid&Units=SI [6] Cell Biology: A Short Course (http://books.google.com/books?id=3a6p9pA5gZ8C&pg=PA42) [7] Rigaudy, J.; Klesney, S.P. (1979). Nomenclature of Organic Chemistry. Pergamon. ISBN 0-08-022369-9. OCLC 5008199. [8] "The Nomenclature of Lipids. Recommendations, 1976" (http://www.blackwell-synergy.com/doi/pdf/10.1111/j.1432-1033.1977. tb11778.x). European Journal of Biochemistry 79 (1): 11–21. 1977. doi:10.1111/j.1432-1033.1977.tb11778.x. . [9] Food Standards Agency (1991). "Fats and Oils". McCance & Widdowson's the Composition of Foods. Royal Society of Chemistry. [10] Ted Altar. "More Than You Wanted To Know About Fats/Oils" (http://www.efn.org/~sundance/fats_and_oils.html). Sundance Natural Foods Online. . Retrieved 2006-08-31. [11] U. S. Department of Agriculture.. "USDA National Nutrient Database for Standard Reference" (http://www.nal.usda.gov/fnic/ foodcomp/search/). U. S. Department of Agriculture.. . Retrieved 2010-02-17. [12][12] David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2 [13] "Electronic Nose Created To Detect Skin Vapors" (http://www.sciencedaily.com/releases/2009/07/090721091839.htm). Science Daily. July 21, 2009. . Retrieved 2010-05-18.
  23. 23. Fatty acid 19 External links • Lipid Library (http://www.lipidlibrary.co.uk/) • Prostaglandins, Leukotrienes & Essential Fatty Acids Journal (http://intl.elsevierhealth.com/journals/plef/) • Fatty Blood Acids (http://www.dmfpolska.eu/Diagnostics.html) Lye Lye is a corrosive alkaline substance, commonly sodium hydroxide (NaOH, also known as 'caustic soda') or historically potassium hydroxide (KOH, from hydrated potash). Previously, lye was among the many different alkalis leached from hardwood ashes. [1] Today lye is commercially manufactured using a membrane cell method. Solid dry lye is commonly available as flakes, pellets, microbeads, and coarse powder. It is also available as solution, often dissolved in water. Lye is valued for its use in food preparation, soap making, biodiesel production, and household uses, such as oven cleaner and drain opener. Canister of solid dry lye. Food uses Lye is used to cure many types of food, such as lutefisk, green olives, canned mandarin oranges, hominy, lye rolls, century eggs, and pretzels. It is also used as a tenderizer in the crust of baked Cantonese moon cakes, and in lye-water "zongzi" (glutenous rice dumplings wrapped in bamboo leaves), in chewy southern Chinese noodles popular in Hong Kong and southern China, and in Japanese ramen. In the United States, food-grade lye must meet the requirements outlined in the Food Chemicals Codex (FCC), [2] as prescribed by the U.S. Food and Drug Administration (FDA). [3] Lower grades of lye are commonly used as drain openers and oven cleaners and should not be used for food preparation. [3]
  24. 24. Lye 20 Safety Lye is a strong alkali, producing highly basic solutions. Both wet lye and dry lye solutions are highly caustic and may cause chemical burns, permanent injury or scarring, and blindness. Lye may be harmful or fatal if swallowed. Hazardous reactions This image shows the effects of lye upon human skin. Chemical burns of this type can be extremely painful. Solvation of sodium hydroxide is highly exothermic, and the resulting heat may cause heat burns or ignite flammables. The combination of aluminium and sodium hydroxide results in a large production of hydrogen gas: 2Al(s) + 6NaOH(aq) → 3H 2 (g) + 2Na 3 AlO 3 (aq). Hydrogen gas is flammable; mixing lye (sodium hydroxide) and aluminium in a closed container is therefore dangerous. In addition to aluminium, lye (sodium hydroxide) may also react with magnesium, zinc (galvanized), tin, chromium, brass, and bronze to produce hydrogen gas and is therefore dangerous. Lye intoxication can cause esophageal stricture. Protection Personal protective equipment including safety glasses, chemical-resistant gloves, and adequate ventilation are required for the safe handling of lye. When in proximity to lye that is dissolving in an open container of water, the use of a vapor-resistant face mask is recommended. Be aware that adding too much lye to water too quickly can cause the solution to boil and 'spit'. [4] Abstaining from protection can result in serious injuries. Storage Lye is a deliquescent salt and has a strong affinity for moisture. Lye will deliquesce (dissolve or melt) when exposed to open air. It will absorb a relatively large amount of water from the atmosphere (air) if exposed to it. Eventually, it will absorb enough water to form a liquid solution because it will dissolve in the water it absorbs. Hygroscopic substances are often used as desiccants to draw moisture away from water-sensitive items. Desiccants should never be placed inside a canister of lye because lye has much stronger hygroscopic properties than activated carbon and silica gel (the most common ingredients in commercial desiccant packets) and will pull and absorb the water from the desiccant packets. Lye should be stored in air-tight plastic containers. Glass should never be used for storage as lye will slowly eat away at this material. The containers should be labeled to indicate the potential danger of the contents and stored away from children, pets, heat, and moisture. [4]
  25. 25. Lye 21 Soap Making Both sodium hydroxide and potassium hydroxide are used in soap making. Sodium hydroxide is often used to make solid soap while potassium hydroxide is used to make liquid soap. Soaps made of potassium hydroxide are softer and can more easily be dissolved in water than sodium hydroxide soaps. When soap making, sodium hydroxide cannot be substituted with potassium hydroxide and vice versa because soap making recipes will have different quantity requirements for these two chemicals depending on the kind of soap being manufactured. In addition, the quantities required for soap saponification differ when using caustic soda and hydrated potash. Notes [1][1] McDaniel, Robert (1997). [2] Food Chemicals Codex (http://www.usp.org/fcc/) [3] US Food and Drug Administration (http://www.fda.gov/opacom/laws/fdcact/fdcact4.htm) [4] Lye Safety Precautions (http://www.certified-lye.com/safety.html) References • "Federal Food, Drug, and Cosmetic Act" (http://www.fda.gov/opacom/laws/fdcact/fdcact4.htm). US Food and Drug Administration. • "Food Chemicals Codex" (http://www.usp.org/fcc/). United States Pharmacopeia. • "Lye Safety Precautions" (http://www.certified-lye.com/safety.html). Certified Lye. • "NaOH MSDS" (http://cheville.okstate.edu/photonicslab/Safety/safety/MSDS/naoh_msds.htm). • "Lye. An example of sodium." (http://periodictable.com/Items/011.14/index.qtvr.html). • McDaniel, Robert (1997). The Elegant Art of Handmade Soap: Making, Scenting, Coloring, and Shaping. Iola, WI: Krause Publications. ISBN 0-87341-832-8.
  26. 26. Melt and pour 22 Melt and pour Melt and Pour Soap Crafting is a process often used by soapmakers. The process differs from the cold process or hot process in that no soap is made (i.e. no actual saponification occurs) in the process; a melt and pour soap base acquired in commerce is melted in a direct heat melter or water jacket melting pot (large double boiler) and additional items such as fragrance, essential oils, moisturizing agents, colorants, or exfoliating agents are added. While still hot, the concoction can be poured into individual molds, tray molds, or blocks which upon cooling can be sliced. Melt and pour does not give the soaper complete control over the ingredients (i.e., the choice of fat to use). Most soaps do not melt readily once they have saponified; the exceptions are clear glycerin soaps, and white soap made from white coconut oil. Melt and pour bases are typically manufactured from these types of soap. Some soapmakers prefer melt and pour because the process is easy and allows the soapmaker to concentrate more on the aesthetic aspects of soap making. It also avoids the need to handle lye, which is a hazardous and very caustic chemical. However, as with rebatching, it can be considered a misnomer to refer to the melt and pour process as soap making. Other processes used by soapers are cold process, hot process and rebatching. Rebatching Rebatching, or hand milling, is a soapmaking technique used by hobbyists and artisan soapmakers. The commercial equivalent is French milling. In rebatching, commercially purchased or previously made soap (a soap base) is shredded or diced finely and mixed with a liquid, into which the soap shreds begin to dissolve. It is then heated at a fairly low temperature until the mass is more or less homogenous. When it becomes translucent and reaches a thick, gel-like consistency, it is spooned or piped into molds and allowed to harden. Soapmakers frequently use rebatching as a way of adding substances that could not withstand the high temperatures or caustic chemical environment of cold process or hot process soapmaking, such as certain essential oils (for example, those with a very low flash point). The choice of liquid affects the character of the finished soap; milk is frequently used to give the soap a smooth, creamy consistency. Rebatching can also be used as a way of salvaging soap that cracked, curdled or separated while being made. As with the melt and pour process, rebatching does not necessarily involve saponification, and as such it is a misnomer to refer to it as soap-"making".
  27. 27. Saponification 23 Saponification Saponification of a triglyceride (left) with sodium hydroxide to give soap and glycerine (right). Saponification is a process that produces soap, usually from fats and lye. In technical terms, saponification involves base (usually caustic soda NaOH) hydrolysis of triglycerides, which are esters of fatty acids, to form the sodium salt of a carboxylate. In addition to soap, such traditional saponification processes produces glycerol. "Saponifiable substances" are those that can be converted into soap. [1] Saponification of triglyceride Vegetable oils and animal fats are the main materials that are saponified. These greasy materials, triesters called triglycerides, are mixtures derived from diverse fatty acids. Triglycerides can be converted to soap in either a one- or a two-step process. In the traditional one-step process, the triglyceride is treated with a strong base (e.g., lye), which accelerates cleavage of the ester bond and releases the fatty acid salt and glycerol. This process is the main industrial method for producing glycerol. If necessary, soaps may be precipitated by salting it out with saturated sodium chloride. The saponification value is the amount of base required to saponify a fat sample. For soap making, the triglycerides are highly purified, but saponification includes other base hydrolysis of unpurified triglycerides, for example, the conversion of the fat of a corpse into adipocere, often called "grave wax." This process is more common where the amount of fatty tissue is high, the agents of decomposition are absent or only minutely present, and the burial ground is particularly alkaline. Mechanism of base hydrolysis The mechanism by which esters are cleaved by base involves nucleophilic acyl substitution. [2] The hydroxide anion adds to (or "attacks") the carbonyl group of the ester. The immediate product is an orthoester: At this stage, the orthoester has a choice: Reforming the carbonyl can be accompanied by expulsion of either the hydroxide or the alkoxide. The former leads back to the starting materials and is unproductive (explaining why saponification is in fact an equilibrium). On the other hand, expulsion of the alkoxide generates a carboxylic acid:
  28. 28. Saponification 24 The alkoxide is more basic than the conjugate base of the carboxylic acid, and hence proton transfer is rapid: In a classic laboratory procedure, the triglyceride trimyristin is obtained by extracting it from nutmeg with diethyl ether. [3] Saponification to the sodium salt of myristic acid takes place with NaOH in water. The acid itself can be obtained by adding dilute hydrochloric acid. [4] . Steam hydrolysis Triglycerides are also saponified in a two-step process that begins with steam hydrolysis of the triglyceride. This process gives the carboxylic acid, not its salt, as well as glycerol. Subsequently, the fatty acid is neutralized with alkali to give the soap. The advantage of the two-step process is that the fatty acids can be purified, which leads to soaps of improved quality. Steam hydrolysis proceeds via a mechanism similar to the base-catalysed route, involving the attack of water (not hydroxide) at the carbonyl center. The process is slower, hence the requirement for steam. Applications Knowledge of saponification is relevant to many technologies and many aspects of everyday life. Soft vs hard soap Depending on the nature of the alkali used in their production, soaps have distinct properties. Sodium hydroxide (NaOH) gives "hard soap", whereas, when potassium hydroxide (KOH) is used, a soft soap is formed. Lithium soaps Lithium derivatives of 12-hydroxystearate and several other carboxylic acids are important constituents of lubricating greases. In lithium-based greases, lithium carboxylates are thickeners. "Complex soaps" are also common, these being combinations of metallic soaps, such as lithium and calcium soaps. [5] Fire extinguishers Fires involving cooking fats and oils (classified as class K (US) or F (Australia/Europe/Asia)) burn hotter than flammable liquids, rendering a standard class B extinguisher ineffective. Flammable liquids have flash points under 100 degrees Fahrenheit. Cooking oil is a combustible liquid, since it has a flash point over 100 degrees. Such fires should be extinguished with a wet chemical extinguisher. Extinguishers of this type are designed to extinguish cooking fats and oils through saponification. The extinguishing agent rapidly converts the burning substance to a non-combustible soap. This process is endothermic, meaning that it absorbs thermal energy from its surroundings, which decreases the temperature of the surroundings, further inhibiting the fire.
  29. 29. Saponification 25 Saponification in art conservation Saponification can occur in oil paintings over time, causing visible damage and deformation. The ground layer or paint layers of oil paintings commonly contain heavy metals in pigments such as lead white, red lead, or zinc white. If those heavy metals react with free fatty acids in the oil medium that binds the pigments together, soaps may form in a paint layer that can then migrate upward to the painting's surface. [6] Saponification in oil paintings was first described in 1997. [7] It is believed to be widespread, having been observed in many works dating from the fifteenth through the twentieth centuries, works of different geographic origin, and works painted on various supports, such as canvas, paper, wood, and copper. Chemical analysis may reveal saponification occurring in a painting’s deeper layers before any signs are visible on the surface, even in paintings centuries old. [8] The saponified regions may deform the painting's surface through the formation of visible lumps or protrusions that can scatter light. These soap lumps may be prominent only on certain regions of the painting rather than throughout. In John Singer Sargent’s famous Portrait of Madame X, for example, the lumps only appear on the blackest areas, which may be because of the artist’s use of more medium in those areas to compensate for the tendency of black pigments to soak it up. [9] The process can also form chalky white deposits on a painting’s surface, a deformation often described as "blooming" or "efflorescence," and may also contribute to the increased transparency of certain paint layers within an oil painting over time. [10] The process is still not fully understood. Saponification does not occur in all oil paintings containing the right materials. It is not yet known what triggers the process, what makes it worse, or whether it can be halted. [11] At present, retouching is the only known restoration method. References [1] K. Schumann, K. Siekmann “Soaps” in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim [2] John McMurry, Organic Chemistry (2nd Edition). [3] Organic Syntheses 1:538 Link (http://orgsynth.org/orgsyn/pdfs/CV1P0538.pdf) [4] Organic Syntheses 1:379 Link (http://orgsynth.org/orgsyn/pdfs/CV1P0379.pdf) [5][5] Thorsten Bartels et al. "Lubricants and Lubrication" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Weinheim. doi:10.1002/14356007.a15 423 [6] Silvia A. Centeno and Dorothy Mahon, "The Chemistry of Aging in Oil Paintings: Metal Soaps and Visual Changes." The Metropolitan Museum of Art Bulletin’’, Summer 2009, pp. 12-19. [7] Researchers in the Netherlands discovered it while analyzing Rembrandt's The Anatomy Lesson of Dr. Nicolaes Tulp (1632). See Centeno, p. 14. [8][8] Centeno, p. 16. [9][9] Centeno, pp. 12-13, 15. [10][10] Centeno, pp. 16, 19. [11][11] Centeno, p. 19. External links • Soapmaking at Bellaonline (http://www.bellaonline.com/site/soapmaking) - Soapmaking articles, forum and supplier links. • Soap Naturally Web and Mailing List (http://www.soapnaturally.org/) - Resources for natural handmade soapmakers. • Soap Recipe Corner (http://www.aquasapone.com.au/soapmaking) - Soapmaking explained. • About Candle and Soap Making (http://candleandsoap.about.com) - Soap making at About.com • Glossary for the Modern Soap Maker (http://www.ccnphawaii.com/glossary.htm) - A collection of terms, definitions and acronyms for today's soap maker. • The Handbook of Soap Manufacture (http://www.gutenberg.org/etext/21724) - A book from 1908.
  30. 30. Soap substitute 26 Soap substitute A soap substitute refers to detergents or cleansing creams, other than soap, for cleaning the skin, especially removing greasy films or glandular exudates. [1] Soap substitutes can be made from a variety of sources including plants with high saponin levels. Soap substitutes should not be confused with natural cleaning products which are cleaning agents for kitchen and house use. Plants with high saponin levels are purported to contain saponins in sufficient quantities to produce lather (when mashed plant parts are beaten in water) and can be used either as is or in soap or shampoos. [2] Soap substitute plants • The soap plant group (amole root, soap plant root, soaproot bulb) • Red campion root and leaves • Mojave yucca root • Guaiac leaves • Atriplex root • Soapwort root • Papaya leaves • Sapindus fruit • Our Lord's Candle root • Quillaia bark •• Passiflora foetida • Wild gourd fruit (Cucurbita foetidissima[?]) •• Alphitonia excelsa • Soap pod fruit (various acacias) References [1] Soap substitute definition (http://medical-dictionary.thefreedictionary.com/soap+substitute) [2][2] The Herb Book by John Lust
  31. 31. Soaper 27 Soaper In modern slang, a soaper is a person who practices soap making. It is the origin of the surnames "Soper," "Saboni," (Arabic for soap maker) and "Soaper." Roads named "Sopers Lane," "Soper Street," and so forth are often so named because historically they were centres for soap making. Historically, in England and in the United States, a "chandler" is a person who makes soap and/or candles for profit. [1][2][3] Whilst much soap nowadays is mass-produced by industrial chemical companies, some people still make soap themselves; sometimes out of a desire for a higher-quality or different soap product than can be purchased, sometimes for the sake of keeping the traditional soap making methods alive, and sometimes as technical avocation, in conjunction with an interest in chemistry or manufacturing. The hobby of soap making has enjoyed various eras of popularity. In recent years, making soap by hand and using it in place of synthetic detergents is also seen as a way to more sustainable living. References [1][1] McDaniel, Robert (2000). [2][2] Miller Cavitch, Susan (1997). [3][3] The Merriam-Webster Doictionary (1994). Bibliography 1. McDaniel, Robert (1997). The Elegant Art of Handmade Soap: Making, Scenting, Coloring, and Shaping. Iola, WI: Krause Publications. ISBN 0-87341-832-8. 2. Miller Cavitch, Susan (1997). The Soap Maker's Companion: A Comprehensive Guide with Recipes, Techniques, and Know-How. North Adams, MA: Storey Books. ISBN 0-88266-965-6. 3. The Merriam-Webster Dictionary. Springfield, MA: Merriam-Webster, Inc. 1994. ISBN 0-87779-911-3. External links • Certified Lye - Using Lye to Make Soap (http://www.certified-lye.com/lye-soap.html) • Glossary for the Modern Soap Maker (http://www.ccnphawaii.com/glossary.htm) • Glossary of Soap Terms (http://www.natural-soap-directory.com/soap-terms.html) Natural Soap Council • Instructions for Cold Process Soap (http://www.pvsoap.com/instructionsforcoldprocess.htm) • Modern Soap Making Methods (http://www.aquasapone.com.au/soapmaking/) - Soap Making: Cold Process, Hot Process, Discounted Water CP • Natural Handmade Soapers Links (http://www.soapnaturally.org/SN_soapmakers.html/) • Natural Soap Directory (http://www.natural-soap-directory.com/) • Soap Making Information (http://www.millersoap.com/) • Why you should use handmade soap (http://www.handmadesoapbar.com/) • Soapmaking Information on Bellaonline.com, the Voice of Women (http://www.bellaonline.com/site/ soapmaking)- Basic and advanced soapmaking information and soap cigarbands and labels - Share information and get answers to questions on the Soapmaking forum at Soapmaking at Bellaonline.
  32. 32. Sodium palmate 28 Sodium palmate Sodium palmate[1] Identifiers CAS number 57-10-3 [2]   PubChem 985 [3] ChEMBL CHEMBL82293 [4]   IUPHAR ligand 1055 [5] Jmol-3D images Image 1 [6] Properties Molecular formula C16 H32 O2 Molar mass 256.42 g/mol Appearance White crystals Density 0.853 g/cm 3 at 62 °C Melting point 62.9 °C [7] Boiling point 351-352 °C [8] 215 °C at 15 mmHg Solubility in water Insoluble Hazards NFPA 704   (verify) [9]  (what is:  / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is the most common fatty acid found in animals, plants and microorganisms [10] . It is a major component of the oil from palm trees (palm oil, palm kernel oil and coconut oil). However, palmitic acid can also be found in meats, cheeses, butter, and dairy products. Its molecular formula is CH 3 (CH 2 ) 14 CO 2 H. As its name indicates, it is a major component of the oil from palm trees (palm oil, palm kernel oil, and coconut oil). Palmitate is a term for the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at basic pH.
  33. 33. Sodium palmate 29 Palmitic acid has been shown (in rats fed on a 20% fat (palmitic acid), 80% carbohydrate diet) to alter aspects of the central nervous system responsible for the secretion of insulin, and to suppress the body's natural appetite-suppressing signals from leptin and insulin -- the key hormones involved in weight regulation [11] . Aluminum salts of palmitic acid and naphthenic acid were combined during World War II to produce napalm (aluminum naphthenate and aluminum palmitate). The word "napalm" is derived from the words naphthenic acid and palmitic acid. Occurrence and production Palmitic acid mainly occurs as its ester in triglycerides (fats), especially palm oil but also tallow. The cetyl ester of palmitic acid (cetyl palmitate) occurs in spermiceti. It was discovered by Edmond Frémy in 1840, in saponified palm oil. [12] Butter, cheese, milk and meat also contain this fatty acid. Palmitic acid is prepared by treating fats and oils with water at a high pressure and temperature (above 200 °C), leading to the hydrolysis of triglycerides. The resulting mixture is then distilled. [13] Biochemistry Excess carbohydrates in the body are converted to palmitic acid. Palmitic acid is the first fatty acid produced during fatty acid synthesis and the precursor to longer fatty acids. Palmitate negatively feeds back on acetyl-CoA carboxylase (ACC), which is responsible for converting acetyl-CoA to malonyl-CoA, which in turn is used to add to the growing acyl chain, thus preventing further palmitate generation. [14] In biology, some proteins are modified by the addition of a palmitoyl group in a process known as palmitoylation. Palmitoylation is important for membrane localisation of many proteins. Applications Palmitic acid is mainly used to produce soaps, cosmetics, and release agents. These applications utilize sodium palmitate, which is commonly obtained by saponification of palm oil. To this end, palm oil, rendered from the coconut palm nut, is treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis of the ester groups. This procedure affords glycerol and sodium palmitate. Because it is inexpensive and adds texture to processed foods (convenience food), palmitic acid and its sodium salt find wide use including foodstuffs. Sodium palmitate is permitted as a natural additive in organic products. [15] Hydrogenation of palmitic acid yields cetyl alcohol, which is used to produce detergents and cosmetics. Recently, a long-acting antipsychotic medication, paliperidone palmitate (marketed as INVEGA Sustenna), used in the treatment of schizophrenia, has been synthesized using the oily palmitate ester as a long-acting release carrier medium when injected intramuscularly. The underlying method of drug delivery is similar to that used with decanoic acid to deliver long-acting depot medication, in particular, neuroleptics such as haloperidol decanoate.
  34. 34. Sodium palmate 30 Dietary effect According to the World Health Organization, evidence is "convincing" that consumption of palmitic acid increases risk of developing cardiovascular diseases, placing it in the same evidence category as trans fatty acids. [16] Retinyl palmitate is an antioxidant and a source of vitamin A added to low fat milk to replace the vitamin content lost through the removal of milk fat. Palmitate is attached to the alcohol form of vitamin A, retinol, to make vitamin A stable in milk. References [1] Merck Index, 12th Edition, 7128. [2] http://www.commonchemistry.org/ChemicalDetail.aspx?ref=57-10-3 [3] http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=985 [4] https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL82293 [5] http://www.iuphar-db.org/DATABASE/LigandDisplayForward?ligandId=1055 [6] http://chemapps.stolaf.edu/jmol/jmol.php?model=CCCCCCCCCCCCCCCC%28%3DO%29O [7] Beare-Rogers, J.; Dieffenbacher, A.; Holm, J.V. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)" (http://iupac.org/ publications/pac/73/4/0685/). Pure and Applied Chemistry 73 (4): 685–744. doi:10.1351/pac200173040685. . [8] Palmitic acid (http://www.inchem.org/documents/icsc/icsc/eics0530.htm) at Inchem.org [9] http://en.wikipedia.org/wiki/Special%3Acomparepages?rev1=415315408&page2=%3ASodium+palmate [10][10] Gunstone, F. D., John L. Harwood, and Albert J. Dijkstra. The Lipid Handbook with Cd-Rom. 3rd ed. Boca Raton: CRC Press, 2007. ISBN-10: 0849396883 | ISBN-13: 978-0849396885 [11] Palmitic acid mediates hypothalamic insulin resistance by altering PKC-θ subcellular localization in rodents (http://www.jci.org/articles/ view/36714), Journal of Clinical Investigation [12] E. Frémy, Memoire sur les produits de la saponification de l’huile de palme, Journal de Pharmacie et de Chimie XII (1842), p. 757. [13][13] David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2 [14] Fatty acid biosynthesis - Reference pathway (http://www.genome.jp/kegg/pathway/map/map00061.html) [15][15] US Soil Association standard 50.5.3 [16] DIET, NUTRITION AND THE PREVENTION OF CHRONIC DISEASES (http://www.who.int/hpr/NPH/docs/ who_fao_expert_report.pdf), WHO Technical Report Series 916, Report of a Joint WHO/FAO Expert Consultation, World Health Organization, Geneva, 2003, p. 88 (Table 10)
  35. 35. Sodium stearate 31 Sodium stearate Sodium stearate Identifiers CAS number 822-16-2 [1]   PubChem 2724691 [2] ChemSpider 12639 [3]   UNII QU7E2XA9TG [4]   Jmol-3D images Image 1 [5] Properties Molecular formula C18 H35 NaO2 Molar mass 306.46 g mol −1 Appearance Yellow/white solid Melting point 245-255 °C, 518-528 K, 473-491 °F Solubility in water soluble   (verify) [6]  (what is:  / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references Sodium stearate is the sodium salt of stearic acid. This white solid is the most common soap. It is found in many types of solid deodorants, rubbers, latex paints, and inks. It is also a component of some food additives and food flavorings. [7] Use Characteristic of soaps, sodium stearate has both hydrophilic and hydrophobic parts, the carboxylate and the long hydrocarbon chain, respectively. These two chemically different components induce the formation of micelles, which present the hydrophilic heads outwards and their hydrophobic (hydrocarbon) tails inwards, providing a lipophilic environment for hydrophobic compounds. It is also used in the pharmaceutical industry as a surfactant to aid the solubility of hydrophobic compounds in the production of various mouth foams.
  36. 36. Sodium stearate 32 Production Sodium stearate is produced as a major component of soap upon saponification of oils and fats. The percentage of the sodium stearate depends on the ingredient fats. Tallow is especially high in stearic acid content (as the triglyceride), whereas most fats only contain a few percent. The idealized equation for the formation of sodium stearate from stearin (the triglyceride of stearic acid) follows: (C 18 H 35 O 2 ) 3 C 3 H 5 + 3 NaOH → C 3 H 5 (OH) 3 + 3 C 17 H 35 CO 2 Na Purified sodium stearate can be made by neutralizing stearic acid with sodium hydroxide. References [1] http://www.commonchemistry.org/ChemicalDetail.aspx?ref=822-16-2 [2] http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=2724691 [3] http://www.chemspider.com/12639 [4] http://fdasis.nlm.nih.gov/srs/srsdirect.jsp?regno=QU7E2XA9TG [5] http://chemapps.stolaf.edu/jmol/jmol.php?model=%5BNa%2B%5D.%5BO-%5DC%28%3DO%29CCCCCCCCCCCCCCCCC [6] http://en.wikipedia.org/wiki/Special%3Acomparepages?rev1=464404070&page2=%3ASodium+stearate [7] Klaus Schumann, Kurt Siekmann, "Soaps" in Ullmann's Encyclopedia of Industrial Chemistry, 2005 Wiley-VCH, Weinheim. doi:10.1002/14356007.a24_247 External links • Safety Data (http://physchem.ox.ac.uk/MSDS/SO/sodium_stearate.html) Sodium tallowate A collection of decorative soaps, often found in hotels In chemistry, soap is a salt of a fatty acid. [1] Soaps are mainly used as surfactants for washing, bathing, and cleaning, but they are also used in textile spinning and are important components of lubricants. Soaps for cleansing are obtained by treating vegetable or animal oils and fats with a strongly alkaline solution. Fats and oils are composed of triglycerides: three molecules of fatty acids attached to a single molecule of glycerol. [2] The alkaline solution, often called lye, brings about a chemical reaction known as saponification. In saponification, the fats are first hydrolyzed into free fatty acids, which then combine with the alkali to form crude soap. Glycerol, often called glycerine, is liberated and is either left in or washed out and recovered as a useful by-product according to the process employed. [2]
  37. 37. Sodium tallowate 33 Two equivalent images of the chemical structure of sodium stearate, a typical soap. Soaps are key components of most lubricating greases, which are usually emulsions of calcium soap or lithium soaps and mineral oil. These calcium- and lithium-based greases are widely used. Many other metallic soaps are also useful, including those of aluminium, sodium, and mixtures of them. Such soaps are also used as thickeners to increase the viscosity of oils. In ancient times, lubricating greases were made by the addition of lime to olive oil. [3] Mechanism of cleansing soaps Structure of a micelle, a cell-like structure formed by the aggregation of soap subunits (such as sodium stearate). The exterior of the micelle is hydrophilic (attracted to water) and the interior is lipophilic (attracted to oils). When used for cleaning, soap serves as a surfactant in conjunction with water. The cleaning action of this mixture is attributed to the action of micelles, tiny spheres coated on the outside with polar hydrophilic (water-loving) groups, encasing a lipophilic (fat-loving) pocket that can surround the grease particles, causing them to disperse in water. The lipophilic portion is made up of the long hydrocarbon chain from the fatty acid. In other words, whereas normally oil and water do not mix, the addition of soap allows oils to disperse in water and be rinsed away. Synthetic detergents operate by similar mechanisms to soap. Effect of the alkali The type of alkali metal used determines the kind of soap produced. Sodium soaps, prepared from sodium hydroxide, are firm, whereas potassium soaps, derived from potassium hydroxide, are softer or often liquid. Historically, potassium hydroxide was extracted from the ashes of bracken or other plants. Lithium soaps also tend to be hard—these are used exclusively in greases. Effects of fats Soaps are derivatives of fatty acids. Traditionally they have been made from triglycerides (oils and fats). [4] Triglyceride is the chemical name for the triesters of fatty acids and glycerin. Tallow, i.e., rendered beef fat, is the most available triglyceride from animals. Its saponified product is called sodium tallowate. Typical vegetable oils used in soap making are palm oil, coconut oil, olive oil, and laurel oil. Each species offers quite different fatty acid content and, hence, results in soaps of distinct feel. The seed oils give softer but milder soaps. Soap made from pure olive oil is sometimes called Castile soap or Marseille soap and is reputed for being extra-mild. The term "Castile" is also sometimes applied to soaps from a mixture of oils, but a high percentage of olive oil.
  38. 38. Sodium tallowate 34 Fatty acid content of various fats used for soap-making Lauric acid Myristic acid Palmitic acid Stearic acid Oleic acid Linoleic acid Linolenic acid fats C 12 , saturated C 14 saturated C 16 saturated C 18 saturated C 18 monounsaturated C 18 diunsaturated C 18 triunsaturated Tallow 0 4 28 23 35 2 1 Coconut oil 48 18 9 3 7 2 0 Palm kernel oil 46 16 8 3 12 2 0 Laurel oil 54 0 0 0 15 17 0 Olive oil 0 0 11 2 78 10 0 Canola 0 1 3 2 58 9 23 |+ History of cleansing soaps Early history Box for Amigo de Obrero (Worker's friend) soap from 20th century. Part of the Museo del Objeto del Objeto collection The earliest recorded evidence of the production of soap-like materials dates back to around 2800 BC in Ancient Babylon. [5] In the reign of Nabonidus (556–539 BCE) a recipe for soap consisted of uhulu [ashes], cypress [oil] and sesame [seed oil] "for washing the stones for the servant girls". [6] A formula for soap consisting of water, alkali, and cassia oil was written on a Babylonian clay tablet around 2200 BC. The Ebers papyrus (Egypt, 1550 BC) indicates that ancient Egyptians bathed regularly and combined animal and vegetable oils with alkaline salts to create a soap-like substance. Egyptian documents mention that a soap-like substance was used in the preparation of wool for weaving. Roman history The word sapo, Latin for soap, first appears in Pliny the Elder's Historia Naturalis, which discusses the manufacture of soap from tallow and ashes, but the only use he mentions for it is as a pomade for hair; he mentions rather disapprovingly that the men of the Gauls and Germans were more likely to use it than their female counterparts. [7] Aretaeus of Cappadocia, writing in the first century AD, observes among "Celts, which are men called Gauls, those alkaline substances that are made into balls, called soap". [8] A popular belief encountered in some places claims that soap takes its name from a supposed Mount Sapo, where animal sacrifices were supposed to take place—tallow from these sacrifices would then have mixed with ashes from fires associated with these sacrifices and with water to produce soap. But there is no evidence of a Mount Sapo within the Roman world and no evidence for the apocryphal story. The Latin word sapo simply means "soap"; it was likely borrowed from an early Germanic language and is cognate with Latin sebum, "tallow", which appears in Pliny the Elder's account. [9] Roman animal sacrifices usually burned only the bones and inedible entrails of the sacrificed animals; edible meat and fat from the sacrifices were taken by the humans rather than the gods. Zosimos of Panopolis, ca. 300 AD, describes soap and soapmaking. [10] Galen describes soap-making using lye and prescribes washing to carry away impurities from the body and clothes. According to Galen, the best soaps were Germanic, and soaps from Gaul were second best. This is a reference to true soap in antiquity. [10]
  39. 39. Sodium tallowate 35 Islamic history A 12th century Islamic document has the world's first extant description of the process of soap production. [11] It mentions the key ingredient, alkali, which later becomes crucial to modern chemistry, derived from al-qaly or "ashes". By the thirteenth century the manufacture of soap in the Islamic world had become virtually industrialized, with sources in Fes, Damascus, and Aleppo. Medieval history Soap-makers in Naples were members of a guild in the late sixth century, [12] and in the 8th century, soap-making was well known in Italy and Spain. [13] The Carolingian capitulary De Villis, dating to around 800, representing the royal will of Charlemagne, mentions soap as being one of the products the stewards of royal estates are to tally. Soap-making is mentioned both as "women's work" and as the produce of "good workmen" alongside other necessities such as the produce of carpenters, blacksmiths, and bakers. [14] 15th–20th centuries Ad for Pear' Soap, 1889 In France, by the second half of the 15th century, the semi-industrialized professional manufacture of soap was concentrated in a few centers of Provence— Toulon, Hyères, and Marseille — which supplied the rest of France. [15] In Marseilles, by 1525, production was concentrated in at least two factories, and soap production at Marseille tended to eclipse the other Provençal centers. [16] English manufacture tended to concentrate in London. [17] Finer soaps were later produced in Europe from the 16th century, using vegetable oils (such as olive oil) as opposed to animal fats. Many of these soaps are still produced, both industrially and by small-scale artisans. Castile soap is a popular example of the vegetable-only soaps derived by the oldest "white soap" of Italy. In modern times, the use of soap has become universal in industrialized nations due to a better understanding of the role of hygiene in reducing the population size of pathogenic microorganisms. Industrially manufactured bar soaps first became available in the late eighteenth century, as advertising campaigns in Europe and the United States promoted popular awareness of the relationship between cleanliness and health. [18] Until the Industrial Revolution, soapmaking was conducted on a small scale and the product was rough. Andrew Pears started making a high-quality, transparent soap in 1789 in London. His son-in-law, Thomas J. Barratt, opened a factory in Isleworth in 1862. William Gossage produced low-price good-quality soap from the 1850s. Robert Spear Hudson began manufacturing a soap powder in 1837, initially by grinding the soap with a mortar and pestle. American manufacturer Benjamin T. Babbitt introduced marketing innovations that included sale of bar soap and distribution of product samples. William Hesketh
  40. 40. Sodium tallowate 36 1922 magazine advertisement for Palmolive Soap. Liquid soap Manufacturing process of soaps/detergents Lever and his brother, James, bought a small soap works in Warrington in 1886 and founded what is still one of the largest soap businesses, formerly called Lever Brothers and now called Unilever. These soap businesses were among the first to employ large-scale advertising campaigns. Soap-making processes The industrial production of soap involves continuous processes, involving continuous addition of fat and removal of product. Smaller-scale production involve the traditional batch processes. There are three variations: the cold-process, wherein the reaction takes place substantially at room temperature, the semi-boiled or hot-process, wherein the reaction takes place at near-boiling point, and the fully boiled process, wherein the reactants are boiled at least once and the glycerol recovered. The cold-process and hot-process (semi-boiled) are the simplest and typically used by small artisans and hobbyists producing handmade decorative soaps and similar. The glycerine remains in the soap and the reaction continues for many days after the soap is poured into moulds. The glycerine is left during the hot-process method, but at the high temperature employed the reaction is practically completed in the kettle, before the soap is poured into moulds. This process is simple and quick and is the one employed in small factories all over the world. Handmade soap from the cold process also differs from industrially made soap in that an excess of fat is used, beyond that which is used to consume the alkali (in a cold-pour process this excess fat is called "superfatting"), and the glycerine left in acts as a moisturizing agent. However, the glycerine also makes the soap softer and less resistant to becoming "mushy" if left wet. Since it is better to add too much oil and have left-over fat, than to add too much lye and have left-over lye, soap produced from the hot process also contains left-over glycerine and its concomitant pros and cons. Further addition of glycerine and processing of this soap produces glycerin soap. Superfatted soap is more skin-friendly than one without extra fat. However, if too much fat is added, it can leave a "greasy" feel to the skin. Sometimes an emollient additive such as jojoba oil or shea butter is added "at trace" (i.e., the point at which the saponification process is sufficiently advanced that the soap has begun to thicken in the cold process method) in the belief that nearly all the lye will be spent and it will escape saponification and remain intact. In the case of hot-process soap, an emollient may be added after the initial oils have saponified so that they remain unreacted in the finished soap. Superfatting can also be accomplished through a process known as "lye discount" in which the soap maker uses less alkali than required instead of adding extra fats.
  41. 41. Sodium tallowate 37 Cold process Even in the cold-soapmaking process, some heat is usually required; the temperature is usually raised to a point sufficient to ensure complete melting of the fat being used. The batch may also be kept warm for some time after mixing to ensure that the alkali (hydroxide) is completely used up. This soap is safe to use after approximately 12–48 hours but is not at its peak quality for use for several weeks. Cold-process soapmaking requires exact measurements of lye and fat amounts and computing their ratio, using saponification charts to ensure that the finished product does not contain any excess hydroxide or too much free unreacted fat. Saponification charts should also be used in hot-processes, but are not necessary for the "fully boiled hot-process" soaping. A cold-process soapmaker first looks up the saponification value of the fats being used on a saponification chart. This value is used to calculate the appropriate amount of lye. Excess unreacted lye in the soap will result in a very high pH and can burn or irritate skin; not enough lye and the soap is greasy. Most soap makers formulate their recipes with a 4–10% deficit of lye so that all of the lye is converted and that excess fat is left for skin conditioning benefits. The lye is dissolved in water. Then oils are heated, or melted if they are solid at room temperature. Once the oils are liquefied and the lye is fully dissolved in water, they are combined. This lye-fat mixture is mixed until the two phases (oils and water) are fully emulsified. Emulsification is most easily identified visually when the soap exhibits some level of "trace", which is the thickening of the mixture. (Modern-day amateur soapmakers often use a stick blender to speed this process). There are varying levels of trace. Depending on how additives will affect trace, they may be added at light trace, medium trace, or heavy trace. After much stirring, the mixture turns to the consistency of a thin pudding. "Trace" corresponds roughly to viscosity. Essential oils and fragrance oils can be added with the initial soaping oils, but solid additives such as botanicals, herbs, oatmeal, or other additives are most commonly added at light trace, just as the mixture starts to thicken. Handmade soaps sold at a shop in Hyères, France The batch is then poured into moulds, kept warm with towels or blankets, and left to continue saponification for 12 to 48 hours. (Milk soaps or other soaps with sugars added are the exception. They typically do not require insulation, as the presence of sugar increases the speed of the reaction and thus the production of heat.) During this time, it is normal for the soap to go through a "gel phase", wherein the opaque soap will turn somewhat transparent for several hours, before once again turning opaque. After the insulation period, the soap is firm enough to be removed from the mould and cut into bars. At this time, it is safe to use the soap, since saponification is in essence complete. However, cold-process soaps are typically cured and hardened on a drying rack for 2–6 weeks before use. During this cure period, trace amounts of residual lye are consumed by saponification and excess water evaporates. During the curing process, some molecules in the outer layer of the solid soap react with the carbon dioxide of the air and produce a dusty sheet of sodium carbonate. This reaction is more intense if the mass is exposed to wind or low temperatures.
  42. 42. Sodium tallowate 38 Traditional Marseille soap Hot processes Hot-processed soaps are created by encouraging the saponification reaction by adding heat to the reaction. This speeds the reaction. Unlike cold-processed soap, in hot-process soaping the oils are completely saponified by the end of the handling period, whereas with cold-pour soap the bulk of the saponification happens after the oils and lye solution emulsification is poured into moulds. In the hot process, the hydroxide and the fat are heated and mixed together at 80–100 °C, a little below boiling point, until saponification is complete, which, before modern scientific equipment, the soapmaker determined by taste (the sharp, distinctive taste of the hydroxide disappears after it is saponified) or by eye; the experienced eye can tell when gel stage and full saponification has occurred. Beginners can find this information through research and classes. Tasting soap for readiness is not recommended, as sodium and potassium hydroxides, when not saponified, are highly caustic. An advantage of the fully boiled hot process in soap making is that the exact amount of hydroxide required need not be known with great accuracy. They originated when the purity of the alkali hydroxides were unreliable, as these processes can use even naturally found alkalis such as wood ashes and potash deposits. In the fully boiled process, the mix is actually boiled (100 °C+), and, after saponification has occurred, the "neat soap" is precipitated from the solution by adding common salt, and the excess liquid drained off. This excess liquid carries away with it much of the impurities and color compounds in the fat, to leave a purer, whiter soap, and with practically all the glycerine removed. The hot, soft soap is then pumped into a mould. The spent hydroxide solution is processed for recovery of glycerine. Molds Many commercially available soap moulds are made of silicone or various types of plastic, although many soap-making hobbyists may use cardboard boxes lined with a plastic film. Soaps can be made in long bars that are cut into individual portions, or cast into individual moulds. Purification and finishing A generic bar of soap, after purification and finishing In the fully boiled process on factory scale, the soap is further purified to remove any excess sodium hydroxide, glycerol, and other impurities, colour compounds, etc. These components are removed by boiling the crude soap curds in water and then precipitating the soap with salt. At this stage, the soap still contains too much water, which has to be removed. This was traditionally done on chill rolls, which produced the soap flakes commonly used in the 1940s and 1950s. This process was superseded by spray dryers and then by vacuum dryers. The dry soap (approximately 6–12% moisture) is then compacted into small pellets or noodles. These pellets or noodles are then ready for soap finishing, the process of converting raw soap pellets into a saleable product, usually bars.

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