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Synthesis and isolation of epoxy secondary amides via direct amidation of Vernonia galamensis seed oil
Author(s) -
Bryant Kent A. A.,
Nwaonicha Chukwuma P.,
Hassan Mahmoud,
Anderson Melissa A.,
Ayorinde Folahan O.
Publication year - 1993
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/bf02542575
Subject(s) - hexane , chemistry , solvent , epoxy , alkyl , reactivity (psychology) , amine gas treating , butylamine , organic chemistry , medicine , alternative medicine , pathology
Vernonia galamensis oil, containing naturally epoxidized triglycerides, was reacted with n ‐butylamine, n ‐pentylamine and n ‐hexylamine to afford high yields of epoxidized secondary amides. Three reaction conditions were investigated: (i) reflux with amines as solvents, (ii) reflux with hexane as the solvent and (iii) room temperature with the amines as solvents. Reactions with amines as refluxing solvents were completed in 1–5 h, while those with hexane went to completion within 2 to 5 d. Room temperature reactions were only ca. 80% complete after several days. Reactivity was increased with higher amine homologs at both reflux and room temperature reaction conditions. Isolated yields of epoxy‐containing amides were about 80% with purity exceeding 96% in all cases. Spectroscopic characterization of the previously unreported alkyl‐vernolamides is provided.