GB456565A - Process for the manufacture of organic chlorine and bromine derivatives - Google Patents

Abstract

Organic chlorine or bromine compounds are produced by reacting chlorine or bromine with salts of organic carboxylic acids with metals, particularly with metals of the first, second, and third groups of the periodic system. Thus, simple acids yield alkyl halides; a -hydroxy acids yield hydrohalogen compounds of the aldehydes; hydroxy acids in which the hydroxyl is not in the a -position yield hydroxyalkyl halides; polyhydroxy acids with one hydroxyl in the a -position yield hydrohalogen compounds of hydroxy-aldehydes; a -halogen fatty acids yield 1,1-dihalogen hydrocarbons; dicarboxylic acids yield dihalogen hydrocarbons; ester acids yield halogen fatty acid esters; a -keto acids yield acid halides; cycloalkane mono- and polycarboxylic acids yield cycloalkyl halides; and amino acids (other than a -amino-acids) yield halogen alkylamines; in each case with the liberation of carbon dioxide. In examples, bromine is reacted with the silver salts of palmitic, lauric, acetic, coconut fatty acids, hydroxy-palmitic, a -brom-stearic, 9--10 dichlor octadecanic (from chlorinated oleic acid) sebacic, sebacic monoethyl ester, pyroracemic and mandelic acids, yielding pentadecyl, undecyl, methyl and mixed alkyl bromides, an aldehyde hydrobromide, dibromheptadecane, 1-brom-8,9-dichlor heptadecane, 1 - 8 - dibrom octane, 9-brom-nonylic acid ethyl ester, acetyl bromide, and benzaldehyde hydrobromide respectively; chlorine is reacted with silver stearate yielding heptadecyl chloride; bromine is reacted with mercurous caprylate and with mercuric palmitate yielding heptyl bromide and pentadecyl bromide (as pentadecyl pyridinium bromide) respectively; and chlorine or bromine is reacted with thallium oenanthate yielding hexyl chloride or bromide. Diluents such as air, carbon tetrachloride, chloroform or ether may be employed.