Structural Effects of Arylstearic Acids as Combination Oxidation and Rust Inhibitors

Snead, Joseph; Messina, Joseph; Gisser, Henry

doi:10.1021/i360019a004

Cited by 4 publications

(2 citation statements)

References 6 publications

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“…24,25 Research has shown that the position of the phenyl group had some influence on the performance of the products, and the performance of methyl esters of phenyl fatty acids located in the middle position is better. 26 In this work, a new understanding of Friedel-Crafts alkylation was reported. Carbocation rearrangement, methyl transfer, and hydrogen transfer existed in the alkylation process.…”

Section: Introductionmentioning

confidence: 95%

Carbocation rearrangement, methyl migration, and long-range hydrogen transfer in phenyl fatty acid esters

Lang,

Gang,

et al. 2023

Journal of Chemical Research

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Various isomers can be observed in the Friedel–Crafts alkylation of benzene. However, the mechanism and influence of these isomerization reactions were still unclear. In this work, several methyl phenylundecanoate were analyzed by gas chromatography–mass spectrometry to explore the isomerization of the Friedel–Crafts alkylation. The results showed that there were three isomerization reactions in the Friedel–Crafts alkylation reaction: five isomers of methyl 6–10-phenylundecanoate due to carbocation rearrangement, five isomers of methyl 6–9-methyldecanoate and methyl undecanoate due to methyl migration, and the loss of neutral alcohol molecular fragments due to hydrogen transfer. At higher reaction temperature, carbocation migration was more active and the formation of methyl undecanoate isomers was observed. There was a competitive relationship between the production of methyl undecanoate isomers and methyl phenylundecanoate isomers. In addition, the hydrogen transfer could be initiated in the presence of unsaturated bonds and alcohol molecules lost as a fragment. The hydrogen from the phenyl groups, which were at a different position on the carbon chain of fatty acid esters, could be transferred to the ester group. It was found that hydrogen could be transferred intramolecularly over a long range. This work revealed the isomerization process in the Friedel–Crafts alkylation and further deepened the understanding of alkylation.

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Section: Introductionmentioning

confidence: 95%

Carbocation rearrangement, methyl migration, and long-range hydrogen transfer in phenyl fatty acid esters

Lang,

Gang,

et al. 2023

Journal of Chemical Research

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“…In addition to anti-wear and anti-oxidation additive, other additives such as detergent, rust inhibitor, viscosity index improver and friction modifier are also added to the lubricant to enhance specific properties. [3][4][5][6] All these additives are different in structure and action mechanism. Consequently, it is inevitable that the additives will affect each other, which may lead to an anti-synergistic effect.…”

Section: Introductionmentioning

confidence: 99%

A study of P-N compound as multifunctional lubricant additive

Wang

Liu

2011

Lubr. Sci.

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A novel P-N compound was synthesised, and its tribological and anti-oxidation behaviours used as lubricant additive for polyalphaolefins (PAO4) were evaluated. The results demonstrate that adding only low amount (<2 wt.%) of P-N compound into PAO4 could improve its anti-wear performance by 10 times, enhance its load-carrying capacity and oxidative stability, verifying the P-N compound is a kind of multifunctional and high-performance additive. The morphology and the chemical composition of the worn surfaces were characterised by scanning electron microscopy and X-ray photoelectron spectroscopy, indicating that the excellent anti-wear and load-carrying performance could be attributed to the forming of boundary lubrication film composed of iron oxide, iron phosphate, organic phosphine and organic amine, and so on. The work reported here is helpful to pave the practical applications and to understand the action mechanism of the multifunctional lubricant additives.

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A review of corrosion inhibitors for rust preventative fluids

Zheng-lin¹

2019

Current Opinion in Solid State and Materials Science

126

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Structural Effects of Arylstearic Acids as Combination Oxidation and Rust Inhibitors

Cited by 4 publications

References 6 publications

Carbocation rearrangement, methyl migration, and long-range hydrogen transfer in phenyl fatty acid esters

Carbocation rearrangement, methyl migration, and long-range hydrogen transfer in phenyl fatty acid esters

A study of P-N compound as multifunctional lubricant additive

A review of corrosion inhibitors for rust preventative fluids

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