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Sodium benzoate also known as benzoate of soda is the sodium salt of benzoic acid, widely used as a food preservative (with an E number of E211) and a pickling agent. It appears as a white crystalline chemical with the formula C 6 H 5 COONa.
It is usually prepared by the dehydration reaction of benzoic acid, e.g. using acetic anhydride: [3] 2 C 6 H 5 CO 2 H + (CH 3 CO) 2 O → (C 6 H 5 CO) 2 O + 2 CH 3 CO 2 H. Alternatively, sodium benzoate can be treated with benzoyl chloride. It can be produced by dehydrating benzoic acid by heating. [citation needed]
Benzyl benzoate is produced industrially by the reaction of sodium benzoate with benzyl chloride in the presence of a base, or by transesterification of methyl benzoate and benzyl alcohol. [8] It is a byproduct of benzoic acid synthesis by toluene oxidation. [11]
The first industrial process involved the reaction of benzotrichloride (trichloromethyl benzene) with calcium hydroxide in water, using iron or iron salts as catalyst. The resulting calcium benzoate is converted to benzoic acid with hydrochloric acid. The product contains significant amounts of chlorinated benzoic acid derivatives.
An electrosynthesis employing alternating current gives phenol from benzene. [27] The oxidation of toluene, as developed by Dow Chemical, involves copper-catalyzed reaction of molten sodium benzoate with air: C 6 H 5 CH 3 + 2 O 2 → C 6 H 5 OH + CO 2 + H 2 O. The reaction is proposed to proceed via formation of benzyoylsalicylate. [8]
The Shorigen reaction is also used in the generation of phenylsodium, where an alkyl sodium compound is treated with benzene: [3] RNa + C 6 H 6 → RH + C 6 H 5 Na. The method can also result in the addition of a second sodium. This dimetallation occurs in the meta and para positions. The use of certain alkyl sodium compounds such as n-amyl ...
Due to the strongly alkaline reaction conditions, aldehydes that have alpha hydrogen atom(s) instead undergo deprotonation there, leading to enolates and possible aldol reactions. Under ideal conditions the reaction produces 50% of both the alcohol and the carboxylic acid (it takes two aldehydes to produce one acid and one alcohol). [5]
The aromatic products of the reaction are then separated from the reaction mixture (or reformate) by extraction with any one of a number of solvents, including diethylene glycol or sulfolane, and benzene is then separated from the other aromatics by distillation. The extraction step of aromatics from the reformate is designed to produce ...