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General
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Benzoic acid, C7H6O2 (or C6H5COOH), is a colorless crystalline solid and
the simplest aromatic carboxylic acid; melting at 122 C; boiling at 249
C; slightly soluble in water, soluble in ethanol, very slightly soluble
in benzene and acetone.
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The
name derived from gum benzoin, which was for a long time the only source
for benzoic acid.
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Benzoic acid is an important precursor for the synthesis of many other
organic substances.
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Benzoic Acid occurs as white laminar crystals or needles. It is odorless
or has a slight odor of benzaldehyde.
Production Process
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The
most of commercial benzoic acid is produced by the reaction of toluene
with oxygen at temperatures around 200 C in the liquid phase and in the
presence of cobalt and manganese salts as catalysts. The process uses
cheap raw materials, proceeds in high yield, and is considered
environmentally green.
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It can
be prepared also by the oxidation of benzene with concentrated sulphuric
acid or carbon dioxide in the presence of catalysts. Other methods are
such as by the oxidation of benzyl alcohol, benzaldehyde, cinnamic acid;
by hydrolysis of benzonitrile, benzoyl chloride.
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Benzoic acid 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.
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For
all syntheses, benzoic acid can be purified by recrystallization from
water because of its high solubility in hot water and poor solubility in
cold water.
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The
first industrial process involved the reaction of benzotrichloride
(trichloromethyl benzene) with calcium hydroxide in water, using iron or
iron salts as catalyst. Benzoic acid for human consumption was obtained
by dry distillation of gum benzoin.
Applications
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Benzoic acid and its salts are used as a food preservative, represented
by the E-numbers E210, E211, E212, and E213.
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Acidic
food and beverage like fruit juice (citric acid), sparkling drinks
(carbon dioxide), soft drinks (phosphoric acid), pickles (vinegar) or
other acidified food are preserved with benzoic acid and benzoates.
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Benzoic acid is a constituent of Whitfield's Ointment which is used for
the treatment of fungal skin diseases such as tinea, ringworm, and
athlete's foot.
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Benzoic acid is used as an anti-microbial agent. It is found in
toothpastes and mouthwashes, cosmetics, and deodorants.
Market
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Benzoic acid continues to outpace the general economy, primarily due to
the healthy demand for benzoate plasticizers.
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Growth
for benzoic acid is forecasted at 2.9 percent per year. On the supply
side, toluene is plentiful and prices hit a low of $0.69 per gallon.
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Capacity is comfortable as the industry is operating at less than 80
percent capacity, including benzoic acid manufactured as an intermediate
for phenol.
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Most
material is consumed captively in the production of a variety of
industrial chemicals. It is estimated that 95 million pounds or 45
percent of Noveon’s benzoic acid is used captively to produce phenol, in
a second partial oxidation process.
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