Abstract
The direct chemical conversion of cocoa butter triglycerides, a material available as a postmanufacture waste stream from the food industry, to 1-decene by way of ethenolysis is reported. The conversion of the raw waste material was made possible by use of 1 mol % of the [RuCl2(iBu-phoban)2(3-phenylindenyl)] catalyst. The process has been investigated in both batch and flow conditions, where the latter approach employs a Teflon AF-2400 tube-in-tube gas–liquid membrane contactor to deliver ethylene to the reaction system. These preliminary studies culminate in a continuous processing system, which maintained a constant output over a 150 min period tested.
Highlights
Biofeedstocks in general and biowaste in particular represent an attractive source of useful chemical functionality, which to date is still largely untapped in terms of its application in the fine chemicals industry
Used cooking oils have been intensively investigated as a feedstock for biodiesel production.[6]. We have identified another source of waste triglycerides from food manufacturing: food ingredients that are discarded after primary food manufacturing
Such tube-in-tube membrane contactors have been applied in several important synthetic reactions and are becoming a generally accepted tool of mesoscale flow chemistry.[40−58] Very recently, ring-closing metathesis was shown to be effectively performed in such a reactor, whereby the ethylene produced could be removed by applying a vacuum across the porous polymeric Teflon AF-2400 membrane.[59]
Summary
Biofeedstocks in general and biowaste in particular represent an attractive source of useful chemical functionality, which to date is still largely untapped in terms of its application in the fine chemicals industry. With the recent introduction of thin and chemically resistant membrane contactors based on Teflon AF-2400 (poly(tetrafluoroethylene-co-2,2-bis(trisfluoromethyl)-4,5-difluoro-1,3-dioxole)) by DuPont, the scope of applications and efficiency of membrane contactors has improved significantly.[39] Such tube-in-tube membrane contactors have been applied in several important synthetic reactions and are becoming a generally accepted tool of mesoscale flow chemistry.[40−58] Very recently, ring-closing metathesis was shown to be effectively performed in such a reactor, whereby the ethylene produced could be removed by applying a vacuum across the porous polymeric Teflon AF-2400 membrane.[59] This technology offers an efficient alternative to the heterogenization of metathesis catalysts allowing truly continuous operation of an optimized catalytic system under its best conditions, we designed our flow system to incorporate the porous membrane gas−liquid contactor design by employing the Teflon AF-2400 tube-in-tube reactor In this context, we report here the direct ethenolysis of raw cocoa butter triglyceride as a waste material from a food manufacturer to provide 1-decene as the major lower weight alkene product. Solvents and reagents were obtained from Sigma-Aldrich and used without further purification
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