ACID ANHYDRIDE

An organic acid anhydride is an organic compound. An

acid anhydride is a compound that has two acylgroup
bonded to the same oxygen atom. A common type of
organic acid anhydride is a carboxylic anhydride, thus
(CH3CO)2 Acidic oxides are often classified as acid
anhydride.

PREPARATION:
Acid anhydrides are prepared in industry by divers
means. Acidic anhydride is mainly products by the
carboxylation of methyl acetate. Maleic anhydride is
produced by the oxidation of benzene or butane.
Laboratory routes emphasize the dehydration of the
corresponding acid. The condition varies from acid to
acid, but phosphorous pent oxide is a common
dehydrating agent.
2CH3COOH + P4O10

CH3C(O)CH3 + (HO)2P4O9

Acid chlorides are also effective precursors:

CH3(O)CL + HCO2Na

HCO2COCH3 +NaCl

Mixed anhydride contains acetyl group are prepared from

ketone.
RCO2 + H2C=C=O

RCO2(O)CH3

APPLICATION & OCCURANCE

Acetic anhydride is produced on a large scale for many
applications.
Napthelenetetracarboxylic dianhydride, a building
block for complex organic compound, is an example
of dianhydrides.
Maleic anhydride is cyclic anhydrides, widely used to
make industrial coating.
ATP in its protonated from is an anhydride derived
from phosphoric acid.
The mixed anhydride 1, 3-bibisphosphogrycerate
occurs widely in metabolic pathways.
Acetic anhydride is a major industrial chemical widely
used to preparing acetates ester,
Example: cellulose acetate. Maleic anhydride is the
precursor to various vesins by so polymerization with
styrene.

BENZOIC ACID
Benzoic acid C7H6O2 (or C6H5COOH) is a colorless
crystalline solid and a simple aromatic carboxylic acid.
The name is derived from gum benzoic, which was for a
long time its only known source. Benzoic acid occurs
naturally in many plants and it serves as an intermediate
in the biosynthesis of many secondary metabolites. Salts
of Benzoic acid are used as food preservation and benzoic
acid is an important precursor for the industrial synthesis
of many other organic substances. The salts and ester of
benzoic acid are known as benzoates.

HISTORY :
Benzoic acid was discovered in the 16 th century. The dry
distillation of gum benzoic was first described by
Nestradamus (156) and then by Alexis Pedemontanus
(1560) and Blaise de Vigenere (1596).
Pioneer work in 1830 through a variety of experience
based on amygdalin, obtained from bitter almonds oil. In
1875 Salkowki
discovered the antifungal abilities of
benzoic acid, which was used for a long time in the
preservation benzoate containing cloudberry fruits.
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It is also one of the chemical compounds found in

castoreum. This compound is gathered from the beaver
plant food.

USES
Benzoic acid is mainly consumed in the production of
phenol by oxidative decarboxylation at 300-400.C.
C6H5CO2H + 1/2O2

C6H5OH + CO2

The temperature required can be lowered to 200.C by

addition of catalytic amount of copper salts.

MEDICINAL:
Benzoic acid is a constituent Whitfields ointment which is
used for the treatment of fungal skin diseases such as
tinea, ringworm and athletes foot. As the principle
component of benzoic resin, benzoic acid also a major
ingredient in both tincture of benzoic and priers balsan.
Benzoic acid was used as an expectorant ,analgesis &
antiseptic in the early 20th century.

BIOLOGY AND HEALTH EFFECTS

Benzoic acid is relatively non-toxic. It occurs naturally as
do its esters in many plants in many species
Appreciable amounts have been found in most berries.
Benzoic acid is also found in apples after infection with
the fungus nectria galigena.
In Taipei, Taiwan, a city health survey in 2010 found
that 30% of dried &pickled food products had too much
benzoic acid, which may affect the liver and kidney of a
person.

PRODUCTION
INDUSTRIAL PREPRATION:
Benzoic acid is produced commercially by partially
oxidation of toluene with oxygen. The process is
catalyzed by cobalt &manganese napthenates. The
process uses cheap raw material and proceeds in high
yield.

LABORATORY SYNTHESIS:
Benzoic acid is cheap & readily available, so the
laboratory synthesis is mainly practiced for its
pedagogical value. It is a common undergraduate
preparation.
Benzoic acid is can be purified by the
recrystillation from water because of its high solubility in
hot water and poor solubility in cold water.

FROM BROMOBENZENE:
Bromobenzene can be converted into benzoic acid by the
carbonation of the intermediate phenyl magnesium
bromide, this synthesis offers of the convenient exercise
for the students to carry out a Grignard reaction, an
important class of carbon-carbon bond from forming
reaction in organic chemistry.

FROM BENZYLOHLORIDE:
Benzoic acid can be prepared by oxidation of benzyl
chloride in the presence of alkaline KMnO4.
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C6H5CH2Cl + 2KOH + 2[O]

+ H2O

C6H5COOH + KCl

REACTION
AROMATIC RING:
O

OH

OH

H2SO4
HSO3

OOH

HNO3

-H2O

-H2O

NO2

NO2

The second substitution reaction (on right) is slower

because the first nitro group is deactivating. Conversely,
if an activating group (electron-donating) was introduced
a second substation reaction would occur more readily
than the first and the distributed product might
accumulate to a significant extent.

CARBOXYL GROUP:
All the reactions mentioned for carboxylic acid are also
possible for benzoic acid.
Benzoic acid, ester are the products of the acid
catalyzed reaction with alcohols.
The more active benzoic anhydride is formed by the
dehydration using acetic anhydride or phosphorus
oxide.
Orthoester can be obtained by the reaction of the
alcohol under acidic water free condition with
benzonitrile.
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 Highly reactive acid derivate such as acid halides are

easily obtained by mixing with halogenations argents
like phosphorus chlorides or thionyl chloride.

LABORATERY PRACTICAL
AIM: To prepare benzoic anhydride & to study
properties.

MATERIAL REQUIRED: China dish, glass funnel,

benzoic acid, cotton healthy source, filter paper.

THEORY: Benzoic anhydride has melting point 42

degree Celsius may be repaired by heating of sodium
benzoate and benzoyl chloride.
C6H5COONa + C6H5COOCl
+ NaCl

(C6H5CO)2O

Better fields are obtaining by the shaking of aqua solution

of benzoate with benzoyl chloride at room temperature in
the presence of pyridine as a solvent.
An alternative method is to slowly distilled a mixture of
benzoic acid & acidic anhydride.
2COH5COOH + (CH3CH)2O
2CH3COOH

(C6H5CO)2 +

Mr. Goo kin (1951) has prepared benzoic anhydride by the

action of dry silver oxide or yellow mercuric oxide on
benzoyl chloride in benzene.
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2C6H5 COCl + Ag2O

(C6H5CO)2O + AgCl

PROCEDURE:
Take benzoic acid in china dish.
Cover the china dish with the funnel has its
cylindrical opening blocked with cotton.
Heat the china dish.
Crystal gets deposits on the walls of the funnel.
Gently collect the crystals on the filter paper.
The crystals obtained are the benzoic anhydride
crystals.

PROPERTIES:
Benzoic anhydride has a melting point of 42 degree
Celsius.
Benzoic anhydride is very slowly decomposed by
water.

BIBLIOGRAPHY

En. Wikipedia.org
N.C.E.R.T Book of class 11th & 12th.
Wiki.answer.com
Knowledge.com

Thank
you..

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