Oxidation

Parashar, Rakesh Kumar

doi:10.1002/9781118681299.ch7

Cited by 1 publication

(1 citation statement)

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“…Epoxidation using performic acid proceeds with retention of stereochemistry, introducing chirality at each of the carbon atoms of the epoxide moiety. Thus, epoxidation of the diepoxide results in a total of three stereoisomers (Scheme S1, Supporting Information) which, upon ring opening, gives a mixture of resulting stereoisomers for each of the branched derivatives.…”

Section: Resultsmentioning

confidence: 99%

Branched Biobased Diesters with Exceptional Low Temperature and Flow Properties for Use in Lubricant Formulations

Raghunanan

Narine

2016

ACS Sustainable Chem. Eng.

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A vegetable oil based diester (1,6-hexyldioleate) was branched with propanoic acid (C3) using a green synthetic approach involving solvent-and catalyst-free epoxide ring opening followed by in situ normal esterification. A total of three branched ester derivatives possessing varied numbers of internal protruding branched ester and hydroxyl groups were obtained. All of the pure branched derivatives were comprised of mixtures of positional and/ or stereoisomers. Differential scanning calorimetry showed that, regardless of the compositional inhomogeneity of each branched derivative, crystallization was suppressed completely in all of the branched compounds and they all demonstrated glass transitions below −65 °C. This unique thermal behavior is attributed to the internal protruding branched moieties and hydroxyl groups which dramatically slowed mass transfer. The viscosity of the branched compounds was 1 order of magnitude larger than that of the starting diester due to the increased resistance to flow associated with increased branching and hydrogen bonding introduced by the OH groups. Overall, these branched diesters demonstrated superior low temperature and flow properties comparable to existing nonsustainable commercial lubricants and analogous biobased materials, making them suitable alternatives for use in lubricant formulations, particularly in high performance industrial gear and bearing biolubricants.

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Section: Resultsmentioning

confidence: 99%