chemistry-phenol-final-1.pdf

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Chemistry phenol final 1
Bachelors in natural science (Government Holkar Science College)
Studocu is not sponsored or endorsed by any college or university
Chemistry phenol final 1
Bachelors in natural science (Government Holkar Science College)
Downloaded by Tanay Chaudhary (tanaychaudhary46@gmail.com)
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INDORE
CHEMISTRY INVESTIGATORY PROJECT
SESSION: 2021-22
TOPIC: “PHENOLS”
Submit to: Sr.Grace Ann
Guided by: Mr. Ashok Muchhala
Submitted by: Manasvi Joshi (XII)
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Certificate
This is to certify that Manasvi Joshi a student of
class XII PCB has successfully completed the
research on the topic Phenols under the guidance
of Mr.Ashok Muchhala during the year 2021-22.
Principal Examiner’s
Signature
School Stamp Teacher In-
charge
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ACKNOWLEDGEMENT
I would like to express my special thanks
of gratitude to my teacher Mr.Ashok
Muchhala and our principal Sr. Grace
Ann who gave me the golden opportunity
to do this project on the topic Phenols. It
helped me in doing a lot of Research and I
came to know about a lot of things
related to this topic.
Finally, I would also like to thank my
faculties and friends who helped me a lot
in finalizing this project within the limited
time frame.
MANASVI JOSHI
XII (PCB)
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PHENOLS
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INDEX
1. Introduction
2. History
3. Methods of preparation
4. Tests for Phenol
5. Natural occurrence of Phenol
6. Content of Phenol in human food
7. Uses of Phenol
8. Toxicity of Phenol
9. Acidity of Phenol
10. Phenolic content in Tea and Wine
11. Case Study
12. Hazards of Phenol
13. Salicylic Acid and its Derivatives
 Aspirin
 Methyl Salicylate
14. Picric Acid
15. Conclusion
16. Bibliography
INTRODUCTION
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Phenols are the hydroxy derivatives of aromatic
hydrocarbons in which the hydroxyl group is directly
attached to the carbon atom of aromatic ring. Phenol is
also known as carbolic acid. It is a white, crystalline solid
with a characteristic odor and a sharp, burning taste. It
tends to turn pink or pale red when exposed to light if not
perfectly pure. It has tendency to absorb moisture from
the air, changing into an aqueous solution of the
compound. Such solutions have a slightly sweet flavor.
They are more soluble in water than are alcohols and
have higher boiling points. The ability of phenols to form
strong hydrogen bonds
also enhances their solubility in water.
BASIC INFORMATION:
Systematic IUPAC name: Benzenol
Chemical formula: C6H6O
Molar mass: 94.113 g/mol
Density: 1.07g/cm3
Melting point: 40.5 °C (104.9 °F; 313.6 K)
Boiling point: 181.7 °C (359.1 °F; 454.8 K)
Solubility in water: 8.3 g/100mL (20 degree C)
Acidity: 9.95 (in water)
Conjugate base: Phenoxide
Dipole moment: 1.224 D
HISTORY
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Phenol was discovered in 1834 by Friedlieb
Ferdinand Runge, who extracted it (in impure form)
from coal tar. Runge called phenol "Karbolsäure"
(coal-oil-acid, carbolic acid). Coal tar remained the
primary source until the development of
the petrochemical industry. In 1841, the French
chemist Auguste Laurent obtained phenol in pure
form.
In 1836, Auguste Laurent coined the name "phène"
for benzene; this is the root of the word "phenol"
and "phenyl". In 1843, French chemist Charles
Gerhardt coined the name "phénol".
The antiseptic properties of phenol were used by
Sir Joseph Lister (1827–1912) in his pioneering
technique of antiseptic surgery. Lister decided that
the wounds themselves had to be thoroughly
cleaned. He then covered the wounds with a piece
of rag or lint covered in phenol, or carbolic acid as
he called it. The skin irritation caused by continual
exposure to phenol eventually led to the
introduction of aseptic (germ-free) techniques in
surgery. Lister experimented with cloths covered in
carbolic acid after studying the works and
experiments of his contemporary, Louis Pasteur in
sterilizing various biological media. Lister was
inspired to try to find a way to sterilize living
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wounds, which could not be done with the heat
required by Pasteur's experiments. In examining
Pasteur's research, Lister began to piece together
his theory: those patients were being killed by
germs. He theorized that if germs could be killed or
prevented, no infection would occur. Lister
reasoned that a chemical could be used to destroy
the micro-organisms that cause infection.
By 16 March 1867, when the first results of Lister's
work were published in the Lancet, he had treated
a total of eleven patients using his new antiseptic
method. Of those, only one had died, and that was
through a complication that was nothing to do with
Lister's wound-dressing technique. Now, for the
first time, patients with compound fractures were
likely to leave the hospital with all their limbs
intact.
Before antiseptic operations were introduced at the
hospital, there were sixteen deaths in thirty-five
surgical cases. Almost one in every two patients
died. After antiseptic surgery was introduced in the
summer of 1865, there were only six deaths in
forty cases. The mortality rate had dropped from
almost 50 per cent to around 15 per cent. It was a
remarkable achievement.
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METHODS OF PREPARATION
Industrial Methods
1) Preparation from coal tar:
Phenol is commercially prepared from the middle oil fraction (443-
503K) of coal tar distillate in which it occurs
with cresols and naphthalene. First naphthalene is removed by
chilling the fraction. The remaining oil is now treated with
H2SO4 to remove basic impurities and phenol is then extracted
with dilute caustic soda. The aqueous layer is separated and
phenol is precipitated with H2SO4 or CO2. It is finally purified by
distillation.
2) Cumene process:
A route analogous to the cumene process begins
with cyclohexylbenzene. It is oxidized to a hydroperoxide, akin to
the production of cumene hydroperoxide. Via the Hock
rearrangement, cyclohexylbenzene hydroperoxide cleaves to give
phenol and cyclohexanone. Cyclohexanone is an important
precursor to some nylons.
3) Miscellaneous method:
Phenyldiazonium salts hydrolyze to phenol. The method is of no
commercial interest since the precursor is expensive.
C6H5NH2 + HCl/NaNO2 → C6H5OH + N2 + H2O + NaCl
Salicylic acid decarboxylates to phenol.
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TESTS FOR PHENOLS
1.Litmus Test:
Phenol turns blue litmus paper red. This shows that phenol is acidic
in nature. Carboxylic acid also gives this test. Compare to carboxylic
acid phenol is weakly acidic and it does not give an effervescence
with aqueous sodium carbonate.
2.Ferric Chloride Test:
Aqueous solution of phenol reacts with freshly prepared ferric
chloride solution gives coloured complex. Most phenols give dark
coloured solution.
The chemical reaction is given below.
6C6H5OH + FeCl3 → [Fe (C6H5O)6]3–
(violet colour complex)+
3HCl + 3H+
The colours produced by simple phenolic compounds with ferric
chloride solution are listed below.
Phenol,
resorcin
ol, Ortho
cresol,
Para
cresol
Violet
or blue
coloura
tion
Catechol Green
coloura
tion
Hydroqui
none
Violet
or
transie
nt blue
color
Pyrogall
ol
Blue
rapidly
changi
ng to
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red
3.Liebermann’s Test:
Phenol reacts with concentrated sulfuric acid and sodium
nitrite forms a yellow colour quinone monoxime complex.
With excess of phenol and sulfuric acid a deep blue
indophenols complex is formed. On dilution a red colour
indophenols is formed which turns to deep blue colour
sodium salt solution of indophenols on treatment with
sodium hydroxide.
4.Phthalein Dye Test:
Phenol on heating with phthalic anhydride in the presence of
concentrated sulfuric acid forms a colourless condensation
compound called phenolphthalein. On further reaction with
dilute sodium hydroxide solution gives a pink colour
fluorescent compound called fluorescein. Characteristic
colours are produced by different phenolic compounds.
Phenol Reddish
pink
o-cresol Red
m-cresol blue or
violet blue
Hydroquinon
e
deep
purple
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NATURAL OCCURRENCE OF PHENOL
Phenols are found in the natural world, especially in the
plant kingdom.
Occurrences in prokaryotes
Orobol can be found in Streptomyces neyagawaensis (an
Actinobacterium). Phenolic compounds can be found in
the cyanobacterium Arthrospira maxima, used in the
dietary supplement, Spirulina. The
proteobacterium Pseudomonas fluorescens
produces phloroglucinol, phloroglucinol carboxylic acid
and diacetylphloroglucinol. Another example of phenolics
produced in proteobacteria is 3, 5-dihydroxy-4-isopropyl-
trans-stilbene.
Occurrences in fungi
Phenolic acids can be found in
mushroom basidiomycetes species. For
example, protocatechuic acid and pyrocatechol are found
in Agaricus bisporus as well as other phenylated
substances like phenylacetic and phenylpyruvic acids.
In Yeast
Aromatic alcohols (example: tyrosol) are produced
by the yeast Candida albicans.They are also found
in beer. These molecules are quorum
sensing compounds for Saccharomyces cerevisiae.
Occurrence in algae
The green alga Botryococcus braunii is the subject of
research into the natural production of butylated
hydroxytoluene (BHT), an antioxidant, food additive and
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industrial chemical. Phenolic acids such
as protocatechuic, p-hydroxybenzoic, 2, 3-
dihydroxybenzoic, chlorogenic, vanillic, caffeic, p-
coumaric and salicylic acid, cinnamic acid have been
isolated from in vitro culture of the freshwater green
alga Spongiochloris spongiosa.
Occurrences in insects
In the analogous hardening of the cockroach ootheca,
the phenolic substance concerned is 3:4-
dihydroxybenzoic acid (protocatechuic acid).
Acetosyringone is produced by the male leaffooted bug
(Leptoglossus phyllopus) and used in its communication
system. Guaiacol is produced in the gut of Desert
locusts. Guaiacol is one of the main components of the
pheromones that cause locust swarming. Orcinol has
been detected in the "toxic glue" of the ant
species. Other simple and complex phenols can be found
in eusocial ants (such as Crematogaster) as components
of venom.[
Occurrences in mammals
In female elephants, the two compounds 3-ethyl
phenol and 2-ethyl 4, 5 dimethylphenol have been
detected in urine samples.
P-Cresol and o-cresol are also components of the
human sweat. P-cresol is also a major component
in pig odor.
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CONTENT OF PHENOL IN HUMAN
FOOD
Berries, tea, beer, oliveoil, chocolate or cocoa, coffee, po
megranates, popcorn, yerba mate, fruits and fruit based
drinks including wine, vinegar etc. are the main sources
of phenol . Herbs and spices, nuts (walnuts, peanut)
and algae are also potentially significant for supplying
certain natural phenols.
Natural phenols can also be found in fatty matrices
like olive oil. Unfiltered olive oil has the higher levels of
phenols, or polar phenols that form a complex phenol-
protein complex.
Phenolic compounds, when used in beverages, such
as prune juice, have been shown to be helpful in the color
and sensory components, such as alleviating bitterness.
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USES OF PHENOL
1.As disinfectant
Phenol is a disinfectant. It is active against a wide range of
micro-organisms including some fungi and viruses. For
example, it is used in floor cleaner like lizol etc.
2. Use in field of medicine
Phenol is also used as an oral analgesic or anesthetic in
products such as Chloraseptic to treat pharyngitis.
Additionally, phenol and its related compounds are used in
surgical ingrown toenail treatment, a process termed
phenolization.
3. Use in germicidal soap
Soap containing phenol-based compounds is often called
carbolic soap. It’s been used as an antiseptic during surgery.
It provides effective, low-cost hygiene to poverty-stricken
communities.
4. Use in DNA extraction
Phenol extraction is a commonly used method for removing
proteins from a DNA sample, e.g. to remove proteins from cell
lysate during genomic DNA preparation.
5.Industrial Use
In industry, phenol is used as a starting material to
make plastics, explosives such as picric acid, and drugs such
as aspirin. Other substituted phenols are used in
the dye industry to make intensely coloured azo dyes.
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TOXICITY OF PHENOL
With respect to health
Phenol and its vapors are corrosive to the eyes, the skin, and
the respiratory tract. Its corrosive effect on skin and mucous
membranes is due to a protein-degenerating effect. Repeated
or prolonged skin contact with phenol may cause dermatitis,
or even second and third-degree burns. Inhalation of phenol
vapor may cause lung edema. The substance may cause
harmful effects on the central nervous system and heart,
resulting in dysrhythmia, seizures,
and coma. The kidneys may be affected as well. Long-term or
repeated exposure of the substance may have harmful effects
on the liver and kidneys.There is no evidence that phenol
causes cancer in humans. Besides its hydrophobic effects,
another mechanism for the toxicity of phenol may be the
formation of phenoxyl radicals.
With respect to environment
The present of phenol and phenolic compound pollutant are
the common problems faced by worldwide population due to
natural and chemical process that comes from either
industrial or human activity. Higher level of phenol leakage
within the environment can actually affects the whole
ecosystem. A toxicological property of phenol has been
contributed by the formation of organic and free radical
species and also due to its hydrophobicity. The structure of
phenol itself shows its reactivity which lead to its properties
like persistence in environment, toxicity and the possibilities
of carcinogenic properties toward living organism.
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ACIDITY OF PHENOL
The acidity of phenols is due to its ability to lose
hydrogen ion to form phenoxide ions.
In a phenol molecule, the sp2
hybridised carbon atom of
the benzene ring attached directly to the hydroxyl group
acts as an electron-withdrawing group. This sp2
hybridized
carbon atom of a benzene ring attached directly to the
hydroxyl group has higher electronegativity in
comparison to the hydroxyl group. Due to the
higher electronegativity of this carbon atom in
comparison to the hydroxyl group attached, electron
density decreases on the oxygen atom. The decrease in
electron density increases the polarity of O-H bond and
results in the increase in ionization of phenols. Thus, the
phenoxide ion is formed. The phenoxide ion formed is
stabilized by the delocalization of negative charge due to
the resonance in the benzene ring. Phenoxide ion has
greater stability than phenols, as in the case of phenol
charge separation takes place during resonance.
The resonance structures of phenoxide ions explain the
delocalization of negative charge. In the case of
substituted phenols, the acidity of phenols increases in
the presence of the electron-withdrawing group. This is
due to the stability of the phenoxide ion generated. The
acidity of phenols further increases if these groups are
attached at ortho and para positions.
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This is due to the fact that the negative charge in
phenoxide ion is mainly delocalized at ortho and para
positions of the attached benzene ring. On the other
hand, the acidity of phenols decreases in the presence of
electron-donating groups as they prohibit the formation of
phenoxide ion.
PHENOLIC CONTENT IN TEA AND
WINE
In Tea
The phenolic content in tea refers to the phenols
and polyphenols, natural plant compounds which are
found in tea. These chemical compounds affect the flavor
and mouthfeel of tea. Polyphenols in tea
include catechins, theaflavins, tannins, and flavonoids.
Polyphenols found in green tea include, but are not
limited to, epigallocatechin
gallate epigallocatechin, epicatechin gallate,
and epicatechin; flavanols such as kaempferol, quercetin,
and myricitin are also found in green tea.
In Wine
The phenolic content in wine refers to the phenolic
compounds natural phenol and polyphenols in wine,
which include a large group of several hundred chemical
compounds that affect the taste, color and mouthfeel of
wine. These compounds
include phenolicacids, stilbenoids, flavonols, dihydroflavo
nols, anthocyanins, flavanol monomers (catechins)
and flavanol polymers (proanthocyanidins). This large
group of natural phenols can be broadly separated into
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two categories, flavonoids and non-flavonoids. Flavonoids
include the anthocyanins and tannins which contribute to
the color and mouthfeel of the wine. The non-flavonoids
include the stilbenoids such as resveratrol and phenolic
acids such as benzoic, caffeic and cinnamic acids.
CASE STUDY
1) Use of Phenol in World War II
The toxic effect of phenol on the central nervous system causes
sudden collapse and loss of consciousness in both humans and
animals; a state of cramping precedes these symptoms because
of the motor activity controlled by the central nervous
system. Injections of phenol were used as a means of individual
execution by Nazi Germany during the Second World War. It was
originally used by the Nazis in 1939 as part of the Aktion
T4 euthanasia program. The Germans learned that extermination
of smaller groups was more economical by injection of each
victim with phenol. Phenol injections were given to thousands of
people. Maximilian Kolbe was also killed with a phenol injection
after surviving two weeks of dehydration and starvation
in Auschwitz when he volunteered to die in place of a stranger.
Approximately one gram is sufficient to cause death.
2) Great Phenol Plot
At the outbreak of World War I in 1914, most phenol used by
American manufacturers was imported from the United Kingdom.
A major precursor compound in organic chemistry, phenol was
used to make both the salicylic acid used to make aspirin, and the
high explosive picric acid (trinitrophenol).
British phenol was soon being used almost exclusively for making
explosives for the war effort, leaving little for export.
Counterfeiters and Canadian importers and smugglers were
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stepping up to meet demand for aspirin, and the war had
disrupted the links between the American Bayer plant
(in Rensselaer, New York) and the central Bayer headquarters in
Germany. Thomas Edison was also facing phenol supply problems;
in response, he built a factory near Johnstown,
Pennsylvania capable of manufacturing 12 short tons (11 t) of
phenol per day. Edison's excess phenol seemed destined for
American trinitrophenol production, which would be used to
support the British.
HAZARDS OF PHENOL
Exposure to phenol may occur from the use of
some medicinal products (including throat lozenges
and ointments). Phenol is highly irritating to the
skin, eyes, and mucous membranes in humans
after acute (short-term) inhalation or dermal
exposures. Phenol is considered to be quite toxic
to humans via oral exposure. Anorexia,
progressive weight loss, diarrhea, vertigo,
salivation, a dark coloration of the urine, and blood
and liver effects have been reported in chronically
(long-term) exposed humans. Animal studies have
reported reduced fetal body weights, growth
retardation, and abnormal development in the
offspring of animals exposed to phenol by the oral
route.
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SALICYLIC ACID AND ITS DERIVATIVES
SALICYLIC ACID
INTRODUCTION:
Salicylic acid is an organic compound with the formula
HOC6H4CO2H. A colorless, bitter-tasting solid, it is a
precursor to and a metabolite of aspirin (acetylsalicylic
acid). The name is from Latin salix for willow tree. Salts
and esters of salicylic acid are known as salicylates.
Chemical formula: C7H6O3
Appearance: Colorless to white crystals
Density: 1.443 g/cm3
(20 °C)
Melting point:
158.6 °C (317.5 °F; 431.8 K)
Boiling point: 200 °C (392 °F; 473 K)
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USES:
Medicine
Salicylic acid as a medication is used commonly to
remove the outer layer of the skin. It is used to treat
warts, psoriasis, acne vulgaris, ringworm etc.
Uses in manufacturing
Salicylic acid has long been a key starting material for
making acetylsalicylic acid (aspirin). Aspirin
(acetylsalicylic acid or ASA) is prepared by
the esterification of the phenolic hydroxyl group of
salicylic acid with the acetyl group from acetic
anhydride or acetyl chloride.
Chemical Reaction:
Industrial synthesis
Sodium salicylate is commercially prepared by
treating sodium phenolate (the sodium salt of phenol)
with carbon dioxide at high pressure (100 atm) and high
temperature (115 °C) – a method known as the Kolbe-
Schmitt reaction. Acidification of the product with sulfuric
acid gives salicylic acid:
History
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In 1979, salicylates were found to be involved in induced
defenses of tobacco against tobacco mosaic virus. In
1987, salicylic acid was identified as the long-sought
signal that causes thermogenic plants such as the voodoo
lily, Sauromatum guttatum, to heat up.
ASPIRIN
Introduction:
Aspirin also known as acetylsalicylic acid is a no
steroidal anti-inflammatory drug (NSAID). It was the first
of this class of drug to be discovered. Aspirin contains
salicylate, a compound found in plants such as the willow
tree and myrtle. Its use was first recorded around 4,000
years ago.
Chemical Formula: C9H8O4
Density: 1.40 g/cm3
Melting Point: 136 °C (277 °F)
Boiling Point: 140 °C (284 °F)
Medical Uses of Aspirin:
Aspirin is used in the treatment of a number of conditions,
including fever, pain, rheumatic fever, and inflammatory
conditions, such as rheumatoid arthritis, pericarditis,
and Kawasaki disease.
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1.Pain:
Aspirin is an effective analgesic for acute pain, although it is
generally considered inferior to ibuprofen because aspirin is more
likely to cause gastrointestinal bleeding. Aspirin is generally
ineffective for those pains caused by
muscle cramps, bloating, gastric distension, or acute skin
irritation.
2. Fever:
Like its ability to control pain, aspirin's ability to control fever is
due to its action on the prostaglandin system through its
irreversible inhibition of COX. Although aspirin's use as
an antipyretic in adults is well established, many medical
societies and regulatory agencies, including the American
Academy of Family Physicians, the American Academy of
Pediatrics, and the Food and Drug Administration, strongly advise
against using aspirin for treatment of fever in children because of
the risk of Reye's syndrome.
3. Heart attacks and strokes:
Aspirin is an important part of the treatment of those who have
had a heart attack. It is generally not recommended for routine
use by people with no other health problems, including those over
the age of 70.
For people who have already had a heart attack or stroke, taking
aspirin daily for two years prevented 1 in 50 from having a
cardiovascular problem (heart attack, stroke, or death), but also
caused non-fatal bleeding problems to occur in 1 of 400
people. Data from early trials of aspirin in primary prevention
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suggested low dose aspirin is more beneficial for people <70 kg
and high dose aspirin is more beneficial for those ≥70 kg.
4. Cancer prevention:
Aspirin is thought to reduce the overall risk of both getting cancer
and dying from cancer. This effect is particularly beneficial
for colorectal cancer (CRC) but must be taken for at least 10–20
years to see this benefit. It may also slightly reduce the risk
of endometrial cancer breast cancer, and prostate cancer.
Some conclude the benefits are greater than the risks due to
bleeding in those at average risk. Others are unclear if the
benefits are greater than the risk.
Chemical Reaction:
The synthesis of aspirin is classified as
an esterification reaction. Salicylic acid is treated with acetic
anhydride, an acid derivative, causing a chemical reaction that
turns salicylic acid's hydroxyl group into an ester group (R-OH →
R-OCOCH3). This process yields aspirin and acetic acid, which is
considered a byproduct of this reaction. Small amounts of sulfuric
acid (and occasionally phosphoric acid) are almost always used as
a catalyst. This method is commonly demonstrated in
undergraduate teaching labs.
HISTORY:
In 1853, chemist Charles Federic Gerhardt treated sodium
salicylate with acetyl chloride to produce acetylsalicylic acid for
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the first time in the second half of the 19th century; other
academic chemists established the compound's chemical
structure and devised more efficient methods of synthesis. In
1897, scientists at the drug and dye firm Bayer began
investigating acetylsalicylic acid as a less-irritating replacement
for standard common salicylate medicines, and identified a new
way to synthesize it. By 1899, Bayer had dubbed this drug Aspirin
and was selling it globally.
Methyl Salicylate
Introduction:
Methyl salicylate (oil of wintergreen or wintergreen oil) is
an organic compound with the formula C6H4(OH)(CO2CH3). It is the
methyl ester of salicylic acid. It is a colorless, viscous liquid with a
sweet, fruity odor reminiscent of root beer, but
often associatively called "minty", as it is an ingredient in mint
candies. It is produced by many species of plants,
particularly wintergreens. It is also produced synthetically, used
as a fragrance and as a flavoring agent.
Chemical Formula: C8H8O3
Density: 1.174 g/cm3
Melting Point: −8.6 °C (16.5 °F; 264.5 K)
Boiling Point: 222 °C (432 °F; 495 K)
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USES:
Methyl salicylate is used in high concentrations as
a rubefacient and analgesic in deep heating liniments (such
as Bengay) to treat joint and muscular pain. Randomized double
blind trials report that evidence of its effectiveness is weak, but
stronger for acute pain than chronic pain, and that effectiveness
may be due entirely to counter irritation. However, in the body it
metabolizes into salicylates, including salicylic acid, a
known NSAID.
Methyl salicylate is used in low concentrations (0.04% and under)
as a flavoring agent in chewing gum and mints. When mixed with
sugar and dried, it is a potentially entertaining source
of triboluminescence, for example by crushing Wint-O-Green Life
Savers in a dark room. When crushed, sugar crystals emit light;
methyl salicylate amplifies the spark because it fluoresces,
absorbing ultraviolet light and re-emitting it in the visible
spectrum. It is used as an antiseptic in Listerine mouthwash
produced by the Johnson & Johnson Company. It
provides fragrance to various products and as an odor-masking
agent for some organophosphate pesticides.
Chemical Reaction:
When salicylic acid is treated with alcohol it gives methyl
salicylate.
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HISTORY:
Methyl salicylate was first isolated (from the plant Gaultheria
procumbens) in 1843 by the French chemist Auguste André
Thomas Cahours (1813–1891), who identified it as
an ester of salicylic acid and methanol.
PICRIC ACID
Introduction:
Picric acid is an organic compound with the formula
(O2N)3C6H2OH. Its IUPAC name is 2, 4, 6-trinitrophenol (TNP).
The name "picric" comes from the Greek word (pikros), meaning
"bitter", due to its bitter taste. It is one of the most acidic phenols.
Like other strongly nitrated organic compounds, picric acid is
an explosive, which is its primary use. It has also been used as
medicine (antiseptic, burn treatments) and as a dye.
Chemical Formula: C6H3N3O7
Molar mass: 229.10 g·mol−1
Density: 1.763 g·cm−3
, solid
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Melting Point: 122.5 °C (252.5 °F; 395.6 K)
Boiling Point: 300 °C (572 °F; 573 K)
USES:
By far the greatest use has been in munitions and
explosives. Explosive D, also known as Dunnite, is the ammonium
salt of picric acid. Dunnite is more powerful but less stable than
the more common explosive TNT (which is produced in a similar
process to picric acid but with toluene as the feedstock).
Picramide, formed by aminating picric acid (typically beginning
with Dunnite), can be further aminated to produce the very stable
explosive TATB. It has found some use in organic chemistry for the
preparation of crystalline salts of organic bases (picrates) for the
purpose of identification and characterization. Picric acid forms
red isopurpurate with hydrogen cyanide (HCN). By photometric
measurement of the resulting dye picric acid can be used to
quantify hydrogen cyanide.
During the early 20th century, picric acid was used to measure
blood glucose levels. When glucose, picric acid and sodium
carbonate are combined and heated, a characteristic red color
forms. With a calibrating glucose solution, the red color can be
used to measure the glucose levels added. This is known as the
Lewis and Benedict method of measuring glucose.
Chemical Reaction:
Picric acid is basically prepared from phenol by reacting phenol
with concentrated sulphuric acid and concentrated nitric acid. The
nitro groups from nitric acid attacks on ortho and para positions
which is the best suitable and stable position for the newly formed
compound which is picric acid.
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HISTORY:
Picric acid was probably first mentioned in the alchemical writings
of Johann Rudolf Glauber. Initially, it was made
by nitrating substances such as animal horn, silk, indigo, and
natural resin, the synthesis from indigo first being performed
by Peter Woulfe during 1771. Picric acid was given that name by
the French chemist Jean-Baptiste Dumas in 1841. Its synthesis
from phenol, and the correct determination of its formula, was
accomplished during 1841. Not until 1830 did chemists think to
use picric acid as an explosive. Before then, chemists assumed
that only the salts of picric acid were explosive, not the acid
itself. In 1871 Hermann Sprengel proved it could be
detonated and most military powers used picric acid as their
main high explosive material. Picric acid is also used in the
analytical chemistry of metals, ores, and minerals.
CONCLUSION
From the above content it can be concluded
that:
Phenols are the simplest hydroxy derivative of
benzene . It is an aromatic compound in which
hydroxyl group is directly attached to the carbon
atom of aromatic ring. Phenol was discovered in
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1834 by Friedlieb Ferdinand Runge who extracted it
(in impure form) from coal tar. In 1843, French
chemist Charles Gerhardt coined the name
"phénol".
Its methods of preparation involve: preparation
from coal tar, from cumene etc.
It occurs in yeast , plants, prokaryotes, fungi ,
algae, insects and mammals.
Berries, coffee, yeast, vinegar are the main sources
of phenol in human diet. Herbs and nuts also
include phenol.
Phenol is used as disinfectant, in medicine, in
germicidal soap, in DNA extraction and in many
industries.
Phenol is very toxic for our health and environment
causing harm to eyes and skin and causing
pollution too.
The acidity of phenols is due to its ability to lose
hydrogen ion to form phenoxide ions.
There are several compounds of phenol found in
tea and wine catechins, theaflavins,
caffeic and cinnamic acids.
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The phenol was widely used during World War II by
Nazis. The rising demand of phenol for
manufacturing of medicines during World War I led
to the occurrence of Great Phenol Plot.
Direct exposure to phenol can cause many
hazards.
The important derivatives of phenol are Salicylic
acid and picric acid.
Many useful drugs are obtained from salicylic acid
such as Aspirin and Methyl salicylate.
As Phenol has many uses it can be of great
importance to the mankind if it is used in proper
manner.
BIBLIOGRAPHY
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NCERT Chemistry (Part 2)
en.wikipedia.org
pubmed.ncbi.nlm.nih.gov
go.drugbank.com
bitesizebio.com
www.britannica.com
cdc.gov.in
medicalnewstoday.com
THANK YOU
lOMoARcPSD|34030076

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