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Improvement of lubricant materials using ruthenium isomerization

Kenneth M. Doll, Erin L. Walter, Grigor B. Bantchev, Michael A. Jackson, Rex E. Murray
Chemical engineering communications 2016 v.203 no.7 pp. 901-907
additives, alkanes, biolubricants, catalysts, chemical engineering, ingredients, isomerization, nuclear magnetic resonance spectroscopy, phosphonates, polymerization, ruthenium, vegetable oil
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 1H 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.