Carboxylic Acids


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All about Carboxylic Acids

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Carboxylic Acids

  1. 1. -are organic acids characterized by the presence of at leastone carboxyl group-the general formula of a carboxylic acid is R-COOH, whereR is some monovalent functional group-A carboxyl group is a functional group consisting ofa carbonyl and a hydroxyl, which has the formula -C(=O)OH, usually written as -COOH or -CO2H.
  2. 2. Monocarboxylic Acids – are the organic acids that containone carboxyl group ( one –COOH ) ex: Formic Acid, Acetic Acid, Propionic Acid, Butyric Acid, Fatty Acids: Palmitic Acid, Myristic Acid, Linolic Acid, Stearic AcidDicarboxylic Acids - are the organic acids that contain twocarboxyl group ( two –COOH ) ex: Oxalic Acid, Malonic Acid, Succinic Acid, Glutaric Acid, Adipic Acid, Pimelic AcidTricarboxylic Acids - are the organic acids that contain twocarboxyl group ( three –COOH ) ex: Citric Acid, Isocitric acid, Aconitic Acid, Carballylic acid, Trimetic Acid
  3. 3. Carbon-Chain Common Name IUPAC name Molecular formula Structural formula C-12 LAURIC ACID dodecanoic acid C12H24O2 C-14 MYRISTIC ACID Tetradecanoic C14H28O2 acid C-16 PALMITIC ACID Hexadecanoic C16H32O2 acid C-18 STEARIC ACID Octadecanoic C18H36O2 acid C-18 OLEIC ACID cis-9- C18H32O2 (unsaturated) Octadecenoic acid C-18 LINOLEIC ACID cis, cis-9,12- C18H34O2(polyunsaturated) octadecadienoic acid
  4. 4. C12H24O2-also called as dodecanoic acid, a saturated fatty acid, isa white, powdery solid with a faint odor of bay oil or soap.-Lauric acid is a medium chain fatty acid which isabundant in coconut oil and is considered responsible formany of its health benefits. Coconut oil is about 50percent lauric acid. The only other abundant sourcefound in nature is in human breast milk.
  5. 5. C12H24O2
  6. 6. C12H24O2Importance/Uses-Lauric acid is inexpensive, has a long shelf-life, and is non-toxic and safe to handle. Thus, it is often used in laboratoryinvestigations offreezing-point depression. Lauric acid is asolid at room temperature but melts easily in boiling water,so liquid lauric acid can be treated with various solutes andused to determine their molecular masses.- a useful component in a treatment for acne and skindisorders.-Used mainly in nutritional supplements- slightly increases cholesterol but it decreases triglyceridelevels and it contains anti-viral, anti-bacterial and anti-protozoal properties.
  7. 7. C12H24O2Harmful Effects-even though it only slightly increases the cholesterol in theblood and good for the heart, high-intake of lauric acid willcause blurred vision, painful migraine, chapped lips and liverdamage.
  8. 8. C14H28O2 -also called tetradecanoic acid- is a common saturated fatty acid with the molecularformula CH3(CH2)12COOH. Amyristate is a salt or ester ofmyristic acid.Myristic acid is named after the nutmeg Myristica fragrans.Nutmeg butter is 75% trimyristin, the triglyceride of myristicacid. Besides nutmeg, myristic acid is also found in palmkernel oil, coconut oil, butter fat and is a minor component ofmany other animal fats
  9. 9. C14H28O2
  10. 10. C14H28O2-Myristic acid is also commonly added co-translationally tothe penultimate, nitrogen-terminus, glycine in receptor-associated kinases to confer the membrane localisation ofthe enzyme.-The myristic acid has a sufficiently high hydrophobicity tobecome incorporated into the fatty acyl core ofthe phospholipid bilayer of the plasma membrane ofthe eukaryotic cell. In this way, myristic acid acts as a lipidanchor in biomembranes.
  11. 11. C14H28O2Harmful Effects-Food that contains myristic acid increases the amount-levelof bad cholesterol in the body and so increases risk ofcoronary heart and cerebrovascular disease-too much intake may cause obesity
  12. 12. C16H32O2CH3(CH2)14COOH or hexadecanoic acid in IUPACnomenclature, is one of the most common saturated fattyacids found in animals and plants.-As its name indicates, it is a major component of the oilfrom palm trees (palm oil, palm kernel oil and coconut oil).The word palmitic is from the French "palmitique", the pith ofthe palm tree. Palmitic acid was discovered by EdmondFrémy in 1840, in saponified palmoil.Butter, cheese, milk and meat also contain this fatty acid.
  13. 13. C16H32O2
  14. 14. C16H32O2Importance/uses-Derivatives of palmitic acid were used in combinationwith naphtha during World War II toproduce napalm (aluminumnaphthenate andaluminum palmitate-is an essential ingredient in soap making-Palmitic acid derivatives are used in different anti-psychoticmedicines, especially in the treatment of schizophrenia
  15. 15. C16H32O2Harmful Effects-palmitic acid has been found to cause obesity and insulinresistance-In contrast, too content of palmitic acid in the body,impairs hypothalamic insulin and leptin signaling. Leptin isan adipocyte synthesized hormone that influences appetitecontrol and signaling. Regardless of obesity, excessdietary palmitic acid impairs leptin and insulins ability toregulate food intake and body weight.-dietary intake of palmitic acid increases risk of developingcardiovascular diseases
  16. 16. C18H36O2-is a saturated fatty acid with the formal IUPACname octadecanoic acid. It is a waxy solid, and its chemicalformula is C18H36O2, or CH3(CH2)16COOH. Its name comesfrom the Greek word stéar (genitive:stéatos), whichmeans tallow. The salts and esters of stearic acid arecalled stearates-It occurs in many animal and vegetable fats and oils, but itis more common in animal fat than vegetable fat. Theimportant exceptions are cocoa butter and sheabutter whose fatty acids consist of 28–45% stearic acid
  17. 17. C18H36O2
  18. 18. C18H36O2Importance/Uses-is useful as an ingredient inmaking candles, plastics, dietary supplements, oilpastels and cosmetics, and for softeningrubber.-It is used to harden soaps, particularly those made withvegetable oil. Stearic acid is used in aerosol shavingcream products.-is also used as a parting compound when making plastercastings from a plaster piece mold or waste mold and whenmaking the mold from a shellacked clay original-used to produce a pearly effect in shampoos, soaps, andother cosmetic products.
  19. 19. C18H36O2Importance/Uses-In fireworks, stearic acid is often used to coat metal powderssuch as aluminium and iron. This prevents oxidation, allowingcompositions to be stored for a longer period of time.-It is used along with simple sugar or corn syrup as a hardenerin candies.-It is used with zinc as zinc stearate as fanning powder forcards to deliver smooth fanning motion.-Stearic acid is one of most commonly used lubricantsduring injection molding and pressing of ceramic powders.-Stearic acid serves as an epilame (or barrier film) treatment,applied to precision mechanical components to modifythe surface properties to reduce the spreading (or creep) ofsubsequently-applied lubricant films.
  20. 20. C18H36O2Harmful Effects-like the other saturated fats, a high-diet in stearic acidincreases LDL in the blood (hypercholesterolemia) thatleads to coronary heart disease and cerebrovasculardiseases-it also leads to obesity
  21. 21. C18H32O2-is a mono-unsaturated omega-9 fatty acid found in variousanimal and vegetable sources. It has the formulaCH3(CH2)7CH=CH(CH2)7COOH. The trans-isomer of oleicacid is called elaidic acid.The term Oleic means related to, or derived from, oil or oliveImportance/Uses-As an excipient in pharmaceuticals, oleic acid is used as anemulsifying or solubilizing agent in aerosol products.-may hinder the progression of ALD, oradrenoleukodystrophy, a fatal disease that affects the brainand adrenal glands-may help boost memory
  22. 22. C18H32O2
  23. 23. C18H32O2Harmful Effects-Oleic and monounsaturated fatty acid levels in themembranes of red blood cells have been associated withincreased risk of breast cancer.-too much body content of Oleic acid may be responsible forthe hypotension ( lower blood pressure) effects of olive oil.
  24. 24. C18H34O2Linoleic acid (LA) is an unsaturated omega-6 fatty acid. It isa colorless liquid at room temperature. In physiologicalliterature, it is called 18:2(n-6). Chemically, linoleic acid isa carboxylic acid with an 18-carbon chain and two cis doublebonds; the first double bond is located at the sixth carbonfrom the omega end.
  25. 25. C18H34O2
  26. 26. C18H34O2Importance/Uses- polyunsaturated fatty acid used in the biosynthesisof arachidonic acid (AA) and thus some prostaglandins. It isfound in the lipids of cell membranes. It is abundant inmany vegetable oils, comprising over half (by weight)of poppy seed, safflower, sunflower, and corn oils.-use for treatment of cancer, Cystic fibrosis, Dermatitis,Diabetes-use for the treatment of hypothyroidism
  27. 27. C18H34O2Harmful Effects-high-diet in linoleic acid cause suppresses the normal oftissue sensitivity to thyroid hormones; greatlysuppresses the livers response to thyroxine andtriiodothyronine, it causes excessive adipose [fat] tissuedevelopment.
  28. 28. Common name IUPAC name Chemical formula Structural formula OXALIC ACID Ethanedioic acid HOOC-COOHMALONIC ACID Propanedioic acid HOOC-(CH2)-COOHSUCCINIC ACID Butanedioic acid HOOC-(CH2) 2-COOHGLUTARIC ACID Pentanedioic acid HOOC-(CH2) 3-COOH ADIPIC ACID Hexanedioic acid HOOC-(CH2) 4-COOH PIMELIC ACID Heptanedioic acid HOOC-(CH2) 5-COOH
  29. 29. HOOC-COOH- is the chemical compound with the IUPAC name,ethanedioic acid.-This colourless solid is a dicarboxylic acid.-In terms of acid strength, it is about 3,000 times strongerthan acetic acid. Its conjugate base, known asoxalate(C2O42-), is a reducing agent as well as a chelatingagent for metal cations. Typically oxalic acid occurs as thedihydrate with the formula C2O4H2·2H2O.
  30. 30. HOOC-COOH
  31. 31. HOOC-COOHImportance/Uses-Oxalic acids main applications include cleaning orbleaching, especially for the removal of rust-About 25% of produced oxalic acid is used as a mordant indyeing processes.-It is used in bleaches, especially for pulpwood-an important reagent in lanthanide chemistry.
  32. 32. HOOC-COOHImportance/Uses-Oxalic acid is used in the restoration of old wood. Itsreducing properties are utilized in platinotype, the earlyphotographic platinum/palladium printing process.-Vaporized oxalic acid, or a 6% solution of oxalic acid insugar syrup, is used by some bee keepers asa miticide against the parasitic Varroa mite.
  33. 33. HOOC-COOHHarmful Effects-Those with kidney disorders, gout, rheumatoid arthritis, orcertain forms of chronic vulvar pain (vulvodynia) are typicallyadvised to avoid foods high in oxalic acid.- The calcium oxalate crystals or precipitate (better knownas kidney stones) can obstruct the kidney tubules. Anestimated 80% of kidney stones are formed from calciumoxalate.
  34. 34. HOOC-COOHHarmful Effects- Oxalic acid is corrosive to body tissue. When ingested,oxalic acid removes calcium from the blood. Kidney damagecan be expected as the calcium is removed from the bloodin the form of calcium oxalate. The calcium oxalate thenobstructs the kidney tubules.
  35. 35. HOOC-(CH2)-COOH-(IUPAC systematic name: propanedioic acid) isa dicarboxylic acid..- is a white crystalline C-3 dicarboxylic acid; melting at 135 -136 C; readily soluble in water, alcohol and ether; solution inwater is medium-strong acidic. It can be derived by oxidizingmalic acid or by the hydrolysis of cyanacetic acid. Malonicacid itself is rather unstable and has few applications. Itsdiethyl ester (diethyl malonate) is more importantcommercially.Malonic acid and its esters contain activemethylene groups which have relatively acidic alpha-protonsdue to H atoms adjacent to two carbonyl groups.The nameoriginates from the Greek word μᾶλον (malon) meaningapple.
  36. 36. HOOC-(CH2)-COOH
  37. 37. HOOC-(CH2)-COOHImportance/Uses-It decomposes above its melting point to ethanoic acid.Propanedioic acid is used in the synthesis of otherdicarboxylic acids.-they are important intermediates in syntheses of vitaminsB1 and B6, barbiturates, non-steroidal anti-inflammatoryagents, other numerous pharmaceuticals, agrochemicalsand flavors & fragrances compounds.
  38. 38. HOOC-(CH2)-COOHHarmful Effects-When inhaled causes Cough. Sore throat. Skin and Eyes:Redness and PainIngestion: Abdominal pain. Diarrhoea.Nausea. Vomiting.- Chronic administration of malonic acid produces selectiveneural degeneration and transient changes in calbindinimmunoreactivity in humans.
  39. 39. HOOC-(CH2) 2-COOH(IUPAC systematic name: butanedioic acid; historicallyknown as spirit of amber), a dicarboxylic acid. The namederives from Latin succinum, meaning amber, from whichthe acid may be obtained.-Succinic Acid (Butanedioic Acid) is a dicarboxylic acid offour carbon atoms. It occurs naturally in plant and animaltissues.-Succinic acid is a colourless crystalline solid with a meltingpoint of 185 -187 C; soluble in water; slightly dissolved inethanol, ether, acetone and glycerine; not dissolved inbenzene, carbon sulfide, carbon tetrachloride and oil ether.The common method of synthesis of succinic acid is thecatalytic hydrogenation of maleic acid or its anhydride.
  40. 40. HOOC-(CH2) 2-COOH
  41. 41. HOOC-(CH2) 2-COOHImportance/Uses-plays a significant role in intermediary metabolism (Krebscycle) in the body. Krebs cycle (also called citric acid cycle;tricarboxylic acid cycle) is a sequence process of enzymaticreaction which a two-carbon acetyl unit is oxidized to carbondioxide and water to provide energy in the form of high-energy phosphate bonds-helpful in normalizing red blood cell glutathione levels inchildren with autism.
  42. 42. HOOC-(CH2) 2-COOHImportance/Uses-Flavoring agent for food and beverages;-Intermediate for dyes, perfumes, lacquers, photographicchemicals, alkyd resins, plasticizer, Metal treatmentchemical, vehicle water cooling systems and coatings.-Medicines of sedative, antispasmer, antiplegm,antiphogistic, anrhoter, contraception and cancer-curing.
  43. 43. HOOC-(CH2) 2-COOHImportance/Uses-Succinate helps reduce the effects of alcohol toxicityincluding hangover by activating the second half-cycle oftricarboxylic acids to help accelerate the decomposition ofacetaldehyde and the energization of the oxidationprocesses in the mitochondria into CO2 and H2O throughaerobic metabolism.
  44. 44. HOOC-(CH2) 2-COOHHarmful Effects-the lack production of succinic acid by the GABA in thebrain may cause Succinic semialdehyde dehydrogenasedeficiency (SSADHD), also known as 4-hydroxybutyricaciduria or gamma-hydroxybutyric aciduria.- Over-production of succinic acid by the GABA in the brainmay inhibits metabolic and neuronal disorders and abnormalfunction of the body systems. It may cause such disorderlike epilepsy.
  45. 45. HOOC-(CH2) 3-COOH-is the organic compound with the IUPAC namePentanedioic acid. Although the related "linear" dicarboxylicacids adipic and succinic acids are water-soluble only to afew percent at room temperature, the water-solubility ofglutaric acid is over 50%.
  46. 46. HOOC-(CH2) 3-COOH
  47. 47. HOOC-(CH2) 3-COOHImportance/Uses-is a dicarboxylic acid with five carbon atoms, occurring inplant and animal tissues. Glutaric acid is found in the bloodand urine. Alpha-ketoglutaric acid, a derivative of glutaricacid which has a ketone group on the carbon atom next tothe acid group, is produced from glutamate in amino groupand found as an intermediate in the Krebs cycle in the body.-In industrial field, ketoglutaric acid exhibits typical carboxylgroup chemistry useful in a variety of industrial applications.It is a white crystalline solid having has the lowest meltingpoint among dicarboxylic acids (98 C).
  48. 48. HOOC-(CH2) 3-COOHHarmful Effects-excessive breakdown of Glutaric acid in the body maycause Glutaric acidemia/glutaric aciduria, it can accumulateand cause damage to the brain (and also other organs), butparticularly the basal ganglia, which are regions that helpregulate movement. GAtype1 causes secondary carnitinedeficiency, as glutaric acid, like other organic acids, isdetoxified by carnitine. Mental retardation may also occur.
  49. 49. HOOC-(CH2) 4-COOH-is the organic compound with is the organic compound withthe IUPAC name, hexanedioic acid. From the industrialperspective, it is the most important dicarboxylic acid: About2.5 billion kilograms of this white crystalline powder areproduced annually, mainly as a precursor for the productionof nylon. Adipic acid otherwise rarely occurs in nature.
  50. 50. HOOC-(CH2) 4-COOH
  51. 51. HOOC-(CH2) 4-COOHImportance/Uses-adipic acid produced annually is used as monomer for theproduction of nylon by a polycondensation reaction withhexamethylene diamine forming 6,6-nylon. Other majorapplications also involve polymers: it is a monomer forproduction of Polyurethane and its esters are plasticizers,especially in PVC.
  52. 52. HOOC-(CH2) 4-COOHImportance/Uses-In medicine, adipic acid has been incorporated intocontrolled-release formulation matrix tablets to obtain pH-independent release for both weakly basic and weakly acidicdrugs. It has also been incorporated into the polymericcoating of hydrophilic monolithic systems to modulate theintragel pH, resulting in zero-order release of a hydrophilicdrug.
  53. 53. HOOC-(CH2) 4-COOHImportance/UsesIn foods, small but significant amounts of adipic acid areused as a food ingredient as a flavorant and gelling aid. It isused in some calcium carbonate antacids to make them tart.
  54. 54. HOOC-(CH2) 4-COOHHarmful Effects-The large amount of adipic acid production per year, due tothe common product that it produces, has led to anenormous amount of this greenhouse gas to be emitted.There are several specific facts about why N2O is so bad forthe environment. First, N2O is a radioactively and chemicallyactive trace gas believed to contribute to the recent increasein the Earths surface temperature. N2O absorbs reflectedinfrared radiation. Also, estimated atmospheric lifetime ofN2O is 150 years. Last, the estimated impact of anthrogenicN2O is a 6% increase in ozone depletion rate. N2O from theproduction of adipic acid is harmful to the environmentbecause of its heat absorbing and ozone depleting qualities.
  55. 55. HOOC-(CH2) 5-COOH-is the organic compound with -is the organiccompoundwith the IUPAC name, heptanedioic acid,heptanedioic acid . Derivatives of pimelic acid are involvedin the biosynthesis of the amino acid called lysine. Pimelicacid is one methylene longer than a related dicarboxylicacid, adipic acid, a precursor to many polyesters andpolyamides. It is the final member of the mnemonic used toaid recollection of the order of the first six dicarboxylic acidsusing their common (not IUPAC) nomenclature.-Pimelic acid has been synthesized from cyclohexanone andfrom salicylic acid. In the former route, the additional carbonis suppled by dimethyl oxalate, which reacts with theenolate.
  56. 56. HOOC-(CH2) 5-COOH
  57. 57. HOOC-(CH2) 5-COOHHarmful Effects-high-toxicity to humans, including carcinogenicity,reproductive and developmental toxicity, neurotoxicity, andacute toxicity- teratogenic in animals or humans