Production of phosphorus-containing oleochemicals through an epoxide route

Brajendra K. Sharma, Kenneth M. Doll, Mirian S.C. Pereira, Gabriel F.N. Santos, Paulo A.Z. Suarez, Sevim Z. Erhan

Research output: Contribution to journalArticlepeer-review


Phosphorus-containing moieties can be added to the ninth and/or tenth positions of a fatty chain of a methyl ester utilising an epoxide route. In this route, methyl oleate is epoxidised, and then ring opened using dibutyl phosphate to yield - among others - a dioxaphospholane-containing derivative of methyl octadecanoate. Progress of the reaction was determined by gas chromatography-mass spectrometry and compounds were identified by nuclear magnetic resonance spectroscopy. Addition of a titanium and zirconium oxide catalyst increased the yield of dioxaphospholane from 27%, observed without catalyst, to 37%. A similar reaction using bis-2-ethylhexyl phosphate gave 22% and 29% yield. However, an aryl phosphate, diphenyl phosphate, was not active in these reactions. The aliphatic compounds obtained are likely to be useful sulphur and metal-free extreme pressure lubricant additives which are highly compatible with vegetable oil-based lubricants.

Original languageEnglish (US)
Pages (from-to)280-285
Number of pages6
JournalInternational Journal of Sustainable Engineering
Issue number3
StatePublished - Sep 2012


  • renewable energy technologies
  • sustainability
  • sustainable manufacture

ASJC Scopus subject areas

  • Engineering(all)


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