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Phosphorus derivatives of fatty acids. The addition of dialkyl phosphonates to unsaturated acids and the synthesis of some 11‐dialkylphosphonoundecanoamides
Author(s) -
Sasin R.,
De Mauriac R. A.,
Leopold E. J.,
Gordon H. B.,
Sasin G. S.
Publication year - 1965
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/bf02545049
Subject(s) - chemistry , oxalyl chloride , organic chemistry , yield (engineering) , oleic acid , boiling , chloride , phosphorus , ammonia , biochemistry , materials science , metallurgy
A series of dialkylphosphonoundecanoic acids and 9(10)‐dialkylphosphonostearic acids was prepared by the addition of dialkylphosphonates to 10‐undecenoic acid and oleic acid under free radical conditions in 58舑66% yield. The phosphonates used were: dimethyl, diethyl, di‐ n ‐butyl, di‐ n ‐hexyl and di‐2‐ethylhexyl. All of the products are colorless, odorless, thermally stable liquids, insoluble in water and soluble in organic solvents. The dialkylphosphonoundecanoic acids were converted into the corresponding acid chlorides by reaction with oxalyl chloride. The acid chlorides were then converted into the corresponding amides by addition of ammonia. All of the amides are white waxy solids except the 2‐ethylhexyl derivative which is a high‐boiling liquid. Two of the dialkylphosphonoundecanoic acids were converted into the N‐decyl substituted amides by heating with n ‐decylamine. The N‐ n ‐decyl‐11‐dialkylphosphonoundecanoamides are white waxy solids.