Patent GB-190314758-A (GB)
Title: Manufacture of Alcohols and Alcohol Derivatives applicable as or in the Manufacture of Perfumes Flavourings or the like, and of Primary Alcohols generally.
Inventor: BOUVEAULT LOUIS
Filed: 1903-07-02
Granted: 1904-06-16
Abstract: 14,758. Bouveault, L., and Blanc, G. July 2. Alcohols; ethers.-Alcohols or alcohol derivatives applicable as or in the manufacture of perfumes, flavourings, or the like, or as parent materials in the manufacture of aldehydes, halogen derivatives, or the like, are produced from the esters of the corresponding carboxylic-acid derivatives, by reducing them by means of sodium and absolute ethyl or other alcohol. In practice, a mixture of absolute alcohol and the ester is run slowly into a vessel containing sodium, and fitted with a reflux condenser. The alcohol so produced is separated by fractionation, steam distillation, or other suitable method. The process is applicable to all fatty acids and hydroaromatic acids, but not to aromatic acids having the carboxylic group attached to the nucleus, or to acids which give rise to sodio-derivatives or condensation products. Substituted acetoacetates are attacked. Unsaturated acids having alpha-#-ethylenic linking are reduced to the corresponding saturated alcohols. In examples, normal butyl alcohol is produced from ethyl butyrate ; normal amyl alcohol from ethyl normal propyl acetoacetate, or normal ethyl valerate ; normal hexyl alcohol from ethyl caproate ; isohexyl alcohol, methyl-4-pentanol-1, from ethyl isobutyl acetoacetate, or ethyl isocaproate ; isohexyl alcohol, methyl-2-pentanol-1, from ethylmethylpropyl acetoacetate; normal octyl alcohol and its acetate, butyrate, valerate, phenylurethane, or its methyl etber from ethyl octoate ; normal nonyl alcohol or its formate, butyrate, acetate, or valerate, from ethyl pelargonate ; normal decyl alcohol from ethyl decoate ; isodecyl alcohol, methyl-3-nonanol-1, from ethyl- #-#-hexylmethylacrylate ; normal dodecyl alcohol or its acetate, butyrate, or valerate, from ethyl laurate ; myristic alcohol or tetradecyl alcohol from methyl myristate ; pentenyl alcohol from ethyl allyl acetate, or ethyl allyl acetoacetate ; decylenyl alcohol, dimethyl-3: 7-octene-6-ol-1, from ethyl 3 : 7 dimethyl-6-octene-1-oate; undecylenyl alcohol from ethyl undecylenate ; oleic alcohol from oleic acid ; hexahydrobenzyl alcohol and its phenylurethane, from ethyl hexahydrobenzoate ; campholene alcohol and its acetate, butyrate, or oxide, from ethyl campholenate ; campholic alcohol from ethyl campholate ; phenylethyl alcohol and its formate, acetate, butyrate, or valerate, from ethyl phenyl ethanoate ; phenylpropyl alcohol or its formate, acetate, butyrate, or valerate, from ethyl benzyl acetoacetate, or ethyl cinnamate: p-methoxyphenylethyl alcohol or its acetate, from ethyl p-methoxyphenylacetate; 2 : 2-dimethylbutane-1 : 4-diol from ethyl alpha-alpha-dimethyl succinate; 2 : 2-dimethylpentane-1 : 5-diol from ethyl alpha-alpha-dimethyl glutarate ; hexane-1 : 6- diol, from methyl adipate ; 2-methylhexane-1 : 6 diol from methyl #-methyl adipate ; octane-1 8-diol from ethyl suberate; decane-1 : 10-diol from ethyl sebacate. The esters mentioned above are produced from the alcohols by known methods. According to the Provisional Specification, phenyl glycol can be produced in a similar manner from ethyl mandelate.