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Products from the reaction of fatty acids with ketones and their characteristic properties as cutting fluids additives
Author(s) -
Watanabe S.,
Fujita T.,
Suga K.,
Sugahara K.
Publication year - 1983
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/bf02540907
Subject(s) - chemistry , yield (engineering) , cyclohexanone , organic chemistry , triethanolamine , lubricity , fatty acid , diethylamine , materials science , catalysis , analytical chemistry (journal) , metallurgy
Hydroxy acids were synthesized in good yields from ketones and fatty acids by the use of lithium naphthalene in the presence of diethylamine. For example, from cyclohexanone and undecylenic acid (I), 2‐(1‐hydroxy‐1‐cyclohexyl)‐10‐undecenoic acid (III) was obtained in 92% yield. Hydroxy acids were treated with p ‐toluenesulphonic acid to give corresponding unsaturated fatty acids. From the reaction of (III), 2‐(1‐cyclohexenyl)‐10‐undecenoic acid (IV), a 3,4‐unsaturated acid was obtained (yield 59%). Corrosion and lubricity tests for these products as water‐based cutting fluid additives were carried out. We have found that triethanolamine salts of 2‐cyclohexenyl and 2‐hydroxycyclohexyl fatty acids showed effective rust‐inhibiting and antiwear properties for water‐based cutting fluids.