BENZOIC ACID
~Benzoic acid is also known as 65-85-0; Benzenecarboxylic acid; Dracylic acid; Carboxybenzene; Benzeneformic acid etc. occurs naturally in many plants and is used as an intermediate in the biosynthesis of many metabolites. It is the simplest aromatic carboxylic acid and is fairly cheap and readily available.
Chemical structure: C7H6O2 (or C6H5COOH)
Odor/ color: faint pleasant, odor, colorless crystalline solid
Production:
a) Commercially it is produced by partial oxidation of toluene with oxygen, and catalyzed by cobalt or manganese naphthenate.
b) Hydrolysis: benzonitrile/ benzamide can be hydrolyzed to benzoic acid or its conjugate base in acid/ basic conditions.
c) Cannizzaro reaction: Disproportionation (redox reaction) of benzaldehyde -> benzoate and benzyl alcohol (can be distilled off)
d) Carboxylation: Bromobenzene can be carboxylated to the intermediate phenylmagnesium bromide for conversion to benzoic acid
e) Benzyl alcohol refluxed with potassium permanganate, then hot filtered to remove manganese dioxide and cooled
f) Oxidation of benzyl chloride with KMnO4: C6H5CH2Cl + 2 KOH + 2 [O] → C6H5COOH + KCl + H2O
Chemical reactions and Uses:
Industrial phenol production by oxidative decarboxylation. Phenol can be converted to cyclohexanol, the starting material for nylon synthesis. It is also used as a precursor to benzoate plasticizers, as well as sodium benzoate and related preservatives. Benzoic acid inhibits mold, yeast and some bacteria and is used in Whitfield’s ointment as an antifungal. Benzoic acid and benzoates are used to preserve acidic food and beverage eg fruit juice, carbonated drinks, pickles. It is also a precursor to benzoyl chloride, a starting material for derivates like benzyl benzoate (used in artificial flavors and insect repellents).
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