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The preparation and properties of some petroselinylamine derivatives
Author(s) -
Placek Lida L.,
Dollear F. G.,
Sumrell Gene
Publication year - 1967
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/bf02666787
Subject(s) - ethylene oxide , acrylonitrile , chemistry , yield (engineering) , xylene , amine gas treating , organic chemistry , oxide , ethanol , hydrochloride , salt (chemistry) , polymer chemistry , materials science , toluene , polymer , copolymer , metallurgy
Petroselinylamine ( cis ‐6‐octadecenylamine) has been prepared by an improved process in which petroselinic acid in xylene is subjected to ammonolysis and treated further to yield the pri‐mary amine without isolating the intermediate products. In addition, the petroselinylamine has been reacted with acrylonitrile, followed by reduc‐tion with metallic sodium and alcohol, to give N‐substituted petroselinyl‐l,3‐trimethylenediamine adducts, and with ethylene oxide under pressure to yield the oxyethylated tertiary amine deriva‐tives. The crude products in each case were mix‐tures of derivatives of various molecular weights. It was possible to isolate the N‐petroselinyl‐1,3‐trimethylenediamine in its pure form from the crude mixture of hydrochloride salts by repeated recrystallizations from aqueous ethanol. The mix‐ture of petroselinylamine‐ethylene oxide deriva‐tives could not be separated.