Synthesis of branched methyl hydroxy stearates including an ester from bio-based levulinic acid

Kenneth M. Doll, Brajendra K. Sharma, Sevim Z. Erhan

Research output: Contribution to journalArticlepeer-review

Abstract

We report the synthesis of five useful branched methyl α-hydroxy stearate esters from commercially available methyl oleate and common organic acids. Of special interest is the synthesis utilizing the natural byproduct, levulinic acid. The other common organic acids, used herein, were propionic acid, hexanoic acid, octanoic acid, and 2-ethylhexanoic acid. The kinetics of the ring opening reaction were studied under pseudo-first-order conditions in the propionic acid system. An Arrhenius activation energy of 66.7 kJ mol -1 (16.0 kcal mol-1) was found. One product, the octanoic ester of methyl hydroxy stearate, was shown to have pour point, cloud point, and viscosity indices of -31 °C, -33 °C, and 101, respectively, all favorable properties in the synthesis of a bio-based lubrication fluid. These products may also prove useful in the synthesis of agriculturally based surfactants and fuel additives.

Original languageEnglish (US)
Pages (from-to)3513-3519
Number of pages7
JournalIndustrial and Engineering Chemistry Research
Volume46
Issue number11
DOIs
StatePublished - May 23 2007
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Industrial and Manufacturing Engineering

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