Premium
Synthesis and Antioxidancy of Some n ‐Alkyl, t ‐Alkyl, Homologous and Isomeric Lipidic Alkylthiobisphenols
Author(s) -
Tyman John H. P.,
Johnson Robert A.
Publication year - 2007
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/s11746-007-1060-6
Subject(s) - alkyl , homologous series , chemistry , steric effects , phenol , medicinal chemistry , side chain , petrochemical , organic chemistry , stereochemistry , polymer
To study the relationship between structure and properties of members of the lipidic thiobis phenol series, as extreme pressure additives in lubricants, a series of homologous compounds has been synthesised by the reaction of alkylphenols with sulphur dichloride. The isomeric n ‐nonylphenols have been reacted to form the C9 isomeric 2,2′‐and 4,4′‐thiobisphenols. Longer alkyl side‐chains resulted mainly in the formation of 4,4′‐thiobisphenols and some of the 2,2′ isomer. With short alkyl, particularly t ‐alkyl side‐chains, steric hindrance resulted in the 2,2′‐compound. Additive studies have indicated that the longer chain 4,4′ compounds possessed antioxidant properties comparable and superior to former commercial branched chain 2,2′ compounds produced from petrochemical intermediates.