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Castor‐based derivatives: Synthesis of some amides
Author(s) -
Applewhite T. H.,
Nelson Jane S.,
Goldblatt L. A.
Publication year - 1963
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/bf02640699
Subject(s) - aminolysis , chemistry , steric effects , sodium methoxide , primary (astronomy) , amide , ricinoleic acid , organic chemistry , yield (engineering) , methanol , ammonia , catalysis , castor oil , physics , materials science , astronomy , metallurgy
Various amides of ricinoleic acid and the related ricinelaidic, hydroxystearic, dihydroxystearic, and trihydroxystearic acids have been synthesized and characterized. Ester aminolysis in methanol solution with sodium methoxide catalyst at room temperature has limited utility since it suffers severe rate retadations due to steric effects with secondary amines. In addition, with primary amines and ammonia, extended reaction times are generally necessary for reasonable, yields. The use of mixed carboxylic‐carbonic anhydrides in amide syntheses was investigated and found applicable without interference from the secondary hydroxyl groups. Also, no appreciable steric effects were observed with most amines. This rapid, high yield method has been employed in the synthesis of a number of new amides from castor‐based acids, ammonia, and primary and secondary amines.