- General procedures for the purification of Acid chlorides
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The corresponding acid and hydrogen chloride are the most likely impurities. Usually these can be removed by efficient fractional distillation. Where acid chlorides are not readily hydrolysed (e.g. aryl sulfonyl chlorides) the compound can be freed from contaminants by dissolving in a suitable solvent such as alcohol-free chloroform, dry toluene or petroleum ether and shaking with dilute sodium bicarbonate solution. The organic phase is then washed with water, dried with anhydrous sodium sulfate or magnesium sulfate, and distilled or recrystallised.
This procedure is hazardous with readily hydrolysable acid chlorides such as acetyl chloride and benzoyl chloride. Solid acid chlorides should be thoroughly dried in vacuo over strong drying agents and are satisfactorily recrystallised from toluene, toluene-petroleum ether, petroleum ethers, alcohol-free chlorofodtoluene, and, occasionally, from dry diethyl ether. Hydroxylic or basic solvents should be strictly avoided. All operations should be carried out in a fume cupboard because of the irritant nature of these compounds which also attack the skin.
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