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Acetylenic compounds. I. The dehydrohalogenation reactions by sodamide in liquid ammonia and preparation of some mono‐acetylenic substances and their derivatives
Author(s) -
Khan N. A.
Publication year - 1953
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02633768
Subject(s) - dehydrohalogenation , chemistry , organic chemistry , ammonia , stearic acid , potassium hydroxide , liquid ammonia , oleic acid , catalysis , biochemistry
Summary The advantages of dehydrohalogenation by sodamide in liquid ammonia over the alcoholic potassium hydroxide method are noted. The sodamine reaction is found to be a mild and quite suitable reaction for the preparation of mono‐acetylenic acids (especially those having long and balanced alkyl groups on either side of the triple bond) by dehydrobromination of the dibromides obtained from the corresponding olefinic compounds. Dehydrobromination of tetrabromostearic acid was unsuccessful. A large laboratory scale preparation of stearolic acid has been accomplished. Stearolic acid and 9,10‐diketo‐stearic were prepared from the crude olive oil acids. A procedure for detecting oleic acid and stearolic acid in mixtures has been outlined. The sodamide dehydrohalogenation method has been successfully applied to the preparation of 6‐octadecynoic acid (for the first time from a natural source, petroselinic acid), phenyl acetylene and 10‐undecynoic acid from their parent olefinic compounds. An explanation for the low yields of the last two substances has been offered.