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Synthesis of 13(14)‐hydroxy‐ cis ‐10‐nonadecenyl amine hydrochloride
Author(s) -
Balakrishnan S.,
Raghavan D.
Publication year - 2003
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/s11746-003-0728-7
Subject(s) - chemistry , nitrile , polymer , amine gas treating , polymer chemistry , epoxide , nuclear chemistry , organic chemistry , catalysis
Compatibility between a hydrophilic nanoclay reinforcement and organophilic polymer matrix resin is achieved by ion exchange reaction substitution of intra gallery mono‐ or divalent cation with foreign aliphatic long‐chain cation. The exchange of long‐chain cation increases the organophilicity of the clay layers and provides sufficient layer separation for polymer chains to impregnate into the formation of a nanocomposite. This study demonstrates the synthesis of hydroxy functional longchain amine hydrochloride from Vernonia galamensis oil (VO). Vernonia galamensis oil, containing a naturally epoxidized long‐chain TG, was transesterified under basic conditions to yield VO methyl esters (VOMe). The VOMe were reduced using lithium aluminum hydride (LAH) in hexane to obtain cis ‐12,13‐epoxy‐ cis ‐9‐octadecenol (vernanol) as the primary product. Vernanol was then converted to vernanyl mesylate, followed by reaction with potassium cyanide to obtain cis ‐13,14‐epoxy‐ cis ‐10‐nonadecenitrile (C 19 nitrile). The C 19 nitrile was reduced with LAH in diethyl ether medium and later reacted with hydrochloric acid to obtain the title product. 1 H and 13 C NMR, FTIR, and matrixassisted laser desorption/ionization time‐of‐flight mass spectrometry (MALDI‐TOFMS) techniques were used to characterize the intermediates and the title product.