Production of phosphorus-containing oleochemicals through an epoxide route

• Published in: International journal of sustainable engineering Vol. 5; no. 3; pp. 280 - 285
• Main Authors: Sharma, Brajendra K., Doll, Kenneth M., Pereira, Mirian S.C., Santos, Gabriel F.N., Suarez, Paulo A.Z., Erhan, Sevim Z.
• Format: Journal Article
• Language: English
• Published: Abingdon Taylor & Francis Group 01-09-2012; Taylor & Francis Ltd
• Subjects: Lubricants & lubrication; NMR; Nuclear magnetic resonance; renewable energy technologies; sustainability; sustainable manufacture
• ISSN: 1939-7038; 1939-7046
• DOI: 10.1080/19397038.2011.605183

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.