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Homogeneous catalytic hydrogenation of long-chain esters by an osmium pincer complex and its potential application in the direct conversion of triglycerides into fatty alcohols†
Alberto Acosta-Ramirez,Marcello Bertoli,Dmitry G. Gusev,Marcel Schlaf
Green Chemistry Pub Date : 03/06/2012 00:00:00 , DOI:10.1039/C2GC15960K
Abstract

The osmium hydride complexes OsH2(CO)[NH(CH2PiPr2)2] (1) and OsHCl(CO)[NH(CH2PiPr2)2] (2) were evaluated in the catalytic hydrogenation of hexyl octanoate and cis-3-hexenyl hexanoate to alcohols as model substrates for triglycerides. Both complexes achieve full conversion of the saturated ester at 220 °C and 800 psi pressure of hydrogen gas. In the presence of unsaturated substrates, the complexes hydrogenate C[double bond, length as m-dash]C bonds, but are subsequently ineffective in the reduction of the ester moiety. However complex 1 is capable of hydrogenating fully saturated triglycerides (i.e., hardened fats as obtained by separate initial hydrogenation of seed oils using either 1 or 2 or a standard heterogeneous hydrogenation catalyst) giving cetyl and stearyl alcohols as the main products.

Graphical abstract: Homogeneous catalytic hydrogenation of long-chain esters by an osmium pincer complex and its potential application in the direct conversion of triglycerides into fatty alcohols
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