Improvement of Lubricant Materials Using Ruthenium Isomerization. Issue 7 (2nd July 2016)

• Record Type: Journal Article
• Authors: Doll, Kenneth M.; Walter, Erin L.; Bantchev, Grigor B.; Jackson, Michael A.; Murray, Rex E.; Rich, Joseph O.
• Is Part Of: Chemical engineering communications. Volume 203:Issue 7(2016)
• Page Start: 901
• Page End: 907
• Publication Date: 2016-07-02
• Subjects: Isomerization -- Octadecenoic acid -- Phosphonate -- Polyalphaolefin -- Ruthenium carbonyl carboxylate; Chemical engineering -- Periodicals; 660.205
• DOI: 10.1080/00986445.2015.1122596
• Languages: English
• ISSNs: 0098-6445

Abstract

Abstract : Production of an effective industrial lubricant additive from vegetable oils is a high profile and difficult undertaking. One candidate is alkyl 9(10)-dibutylphosphonostearate, which has been made through a radical transformation of alkyl 9-cis-octadecanoate. It is effective, but still suffers from drawbacks. In this report, that synthesis is combined with a ruthenium based isomerization process to create not just one, but an entire series of new chemical compounds. A low level of [Ru(CO)2 (EtCO2 )]n is first used for the isomerization of the starting material, then radical chemistry is employed. A series of methyl dibutylphosphonooctadecanoates was made. In an analogous fashion, trans-7-tetradecene was also isomerized and then polymerized. As in the phosphonate case, the follow-up chemistry could be performed in the presence of the residual isomerization catalyst. The alkane:alkene ratio, observed by 1 H NMR, was found to change from 14:1 in the isomerized starting material to a value of 41:1 in the polymerized material. This methodology, isomerization in tandem with other reactions, gives suitable routes to both biobased polyolefins, and biobased phosphonates, potential key ingredients in biobased lubrication formulations.