Substituted Phenylbutyl Adipates and Hydrocarbons as Oxidatively Autoinhibitive Compounds

Abstract

The color of a 10W 20 hydrotreated base oil did not increase 2 ,-XSTM Union color units in 528 hours, while the color of a highly conventionally refined SAE 10 base oil increased 2 color units in 36 hours.Heavy oils and bright stocks can also be made by hydrotreating deasphalted residua with no other treatment.

Structural Effects of Arylstearic Acids as Combination Oxidation and Rust Inhibitors

“…The addition of methyl, tert-butyl, and other alkyl groups ortho and para on the aryl ring should increase electron density about the tertiary carbon atom, promoting autoxidation of the compound and thus facilitating inhibitor formation. The influence of electron-releasing substituents on the oxidation rates of substituted phenylbutyl adipates, phenyldodecanes, and phenylhexadecanes in recent work has confirmed this hypothesis (7). In the present study, additional alkyl groups produced only a minor increase in inhibition; however, an additional hydroxyl group in the ring was much more effective.…”

“…Preparation of Additives a-Arylstearic Acids. The «-substituted arylstearic acids were prepared by the malonic ester synthesis in a manner similar to the preparation of -phenylstearic acid from diethyl phenyl malonate and cetyl bromide (7). a-Methoxyphenylstearic acid was obtained from cetyl bromide and diethyl /i-methoxyphenyl malonate.…”

“…The 9,12-diarylstearic acids were prepared in a similar manner by reaction of linoleic acid with benzene or phenol. All these products are viscous, dark oils which are mixed isomers resulting from substitution of the aryl groups at various points along the stearic acid chain (7). Analytical data on the compounds are in Table I.…”

Substituted Biphenyls and Terphenyls as Oxidatively Autoinhibitive Compounds

“…Previous work showed that phenolic inhibitors formed during oxidation could not be detected by infrared spectroscopy or gas and paper chromatography, presumably because they reacted further as soon as they were formed (7). I n order to obtain evidence that an inhibitor was formed as a product of oxidation, experiments a t 100' C. were run on mixtures of oxidatively unstable compounds and compounds believed to be autoinhibitive.…”

“…HE phenomenon of autoinhibition was previously explored T i n the autoxidation (100' C.) of methoxy-and alkylsubstituted phenyldodecanes, hexadecanes, and phenylbutyl adipates having an aryl group attached to a tertiary carbon (7). The latter compound, however, oxidized at a much slower rate than sec-butylbenzene.…”