BENZOIC ACID

Benzoic acid is an organic compound which is described by the chemical

formula C6H5COOH. It consists of a carboxyl group attached to a benzene ring.
Therefore, benzoic acid is said to be an aromatic carboxylic acid. This
compound exists as a crystalline, colourless solid under normal conditions. The
name derived from gum benzoin, which was for a long time the only source for
benzoic acid. This weak acid and its salts are used as a food preservative.
Benzoic acid is an important precursor for the synthesis of many other organic
substances.
History:

Benzoic acid was discovered in the 16th century. The dry distillation of gum
benzoin was first described by Nostradamus (1556), and subsequently by
Alexius Pedemontanus (1560) and Blaise de Vigenère (1596). Justus von
Liebig and Friedrich Wöhler determined the structure of benzoic acid in 1832

Selection of route of synthesis:

Benzoic acid is produced commercially by partial

oxidation of toluene with oxygen. The process is catalyzed
by cobalt or manganese naphthenates. The process uses abundant materials,
and proceeds in high yield. It is cheap and readily available, so the laboratory
synthesis of benzoic acid is mainly practiced for its pedagogical value. It is a
common undergraduate preparation.
Benzoic acid can be purified by recrystallization from water because of its high
solubility in hot water and poor solubility in cold water. The avoidance of
organic solvents for the recrystallization makes this experiment particularly
safe. This process usually gives a yield of around 65%.
Route of synthesis:
By hydrolysis
Like other nitriles and amides, benzonitrile and benzamide can be hydrolyzed
to benzoic acid or its conjugate base in acid or basic conditions.
From Grignard reagent
Bromobenzene can be converted to benzoic acid by "carboxylation" of the
intermediate phenylmagnesium bromide.[15] This synthesis offers a convenient
exercise for students to carry out a Grignard reaction, an important class
of carbon–carbon bond forming reaction in organic chemistry.
Oxidation of benzyl compounds
Benzyl alcohol and benzyl chloride and virtually all benzyl derivatives are
readily oxidized to benzoic acid.
Benzotrichloride to benzoic acid
The method of producing benzoic acid from benzotrichloride which comprises
hydrolyzing the benzotrichloride directly with water in the presence of an
anhydrous metal compound at a temperature of about 100 to 120

Pthalic anhydride to benzoic acid

The formation of benzoic acid by the interaction of phthalic anhydride and

water in the vapor phase at a temperature of 125 to 350C in the presence of a
phthalate of a member of the group consisting of the alkali metals, alkali earth
metals and Nickel.
Process Flow diagram of Benzoic acid:

Block flow diagram of benzoic acid:

Demand in Market:
Asia Pacific region holds a major share in the benzoic acid market, primarily
due to extensive application in various end-user industries. Apart from the
food and beverage industries, the per capita consumption of plastic is high in
India and China, which in turn has increased the use of plasticizers resulting in
boosting the benzoic acid market. The Region has strongly registered a rising
demand for sodium and potassium benzoate which is yet another factor
driving the overall benzoic acid market. The animal feed industry has is also
attaining maturing in various Asian countries such as India, which is again
boosting the demand for benzoic acid in the region. The stringent government
regulations and an increasing number of small scale food and beverage
industries are also major contributors to fueling the growth of the market.
The benzoic acid is a highly fragmented market with the presence of a large
number of local players across the globe. The extensive application of benzoic
acid in various end-user industries have resulted in an increasing number of
product launches by active manufacturers to consolidate their presence in the
global market. The key players are also expanding their product range to
capture maximum application areas of benzoic acid and attain a prominent
share in the market. Key global players have thus intensified their R&D efforts,
in order to develop a niche and innovative products based on the
requirements of the end-user industry. Key global players have thus intensified
their R&D efforts, in order to develop a niche and innovative products based
on the requirements of the end-user industry.
Safety precautions:
Benzoic acid is non-toxic and stable under ordinary conditions. While
occupational exposure limits have not been established, benzoic acid
may still pose a health risk and, therefore, the safe work practices
should always be followed:

 Wash hands thoroughly after handling

 Use only in a well-ventilated area
 Minimize dust generation and accumulation
 Avoid contact with eyes, skin, and clothing
 Wash clothing before reuse
  Avoid breathing dust
Health precautions:
Immediately or shortly after exposure to benzoic acid, the following health
effects can occur:

 Eye damage
 Irritation of the skin, resulting in a rash, redness, and/or a burning
feeling
 Irritation to the nose, throat and lungs if inhaled, which may cause
coughing, wheezing and/or shortness of breath
In addition to these short-term exposure effects, prolonged or repeated
exposure to benzoic acid can cause drying and cracking of the skin with
redness and itching. Exposure to benzoic acid in high concentrations,
particularly in susceptible individuals, may cause a skin allergy. If an allergy
develops, even exposure to very low levels can cause itching and a skin rash.

Eye Contact

Immediately flush eyes with large amounts of water for at least 15 minutes. If
wearing contact lenses, be sure to remove them before flushing. Seek medical
attention.

Skin Contact

Quickly remove contaminated clothing and wash contaminated skin

immediately with large amounts of soap and water. Seek medical attention.

Inhalation

Individual should be removed from exposure and immediately moved to an

area with fresh air. Seek medical attention immediately.

Ingestion

Get medical aid immediately. Rinse mouth and drink 2-4 cupfuls of milk or
water. Do NOT induce vomiting.

Environmental Precautions:
Immediately or shortly after exposure to benzoic acid, the following
health effects can occur: