Ethenolysis of methyl oleate over supported Re-based catalysts

Sibeijn, M.; Mol, J.C.

doi:10.1016/0304-5102(92)80171-c

Cited by 29 publications

(18 citation statements)

References 13 publications

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“…In particular, the metathesis of methyl oleate (MO) with ethylene (ethenolysis) and with 2-butene were investigated on Ru complexes [10,11,12]while the cross-metathesis of MO with 1-hexene was studied on homogeneousWCl 6 /(CH 3 ) 4 Sn catalysts [13]. [14,15],but there are no reportson the use of immobilized Ru complexes for promoting the cross-metathesis of MO with olefins. Precisely, in this work we study the cross-metathesis of MO with 1-hexene (C6) on second generation RuHoveyda-Grubbs complexes supported onsilica.…”

Section: -Introductionmentioning

confidence: 99%

Valorisation of vegetable oils via metathesis reactions on solid catalysts: Cross-metathesis of methyl oleate with 1-hexene

Zelín

Nieres

Trasarti

et al. 2015

Applied Catalysis A: General

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Section: -Introductionmentioning

confidence: 99%

Valorisation of vegetable oils via metathesis reactions on solid catalysts: Cross-metathesis of methyl oleate with 1-hexene

Zelín

Nieres

Trasarti

et al. 2015

Applied Catalysis A: General

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“…Early works in this field started with the utilization of tungsten and rhenium metathesis catalysts operating under high hydrogen pressure (30 atm), in order to minimize self‐metathesis reactions . With the discovery of efficient ruthenium and molybdenum catalysts, this ethenolysis reaction was extensively studied and significant improvements were achieved in terms of catalytic efficiency and productivity.…”

Section: Applications Of Ethenolysis In Scission Processesmentioning

confidence: 99%

Ethenolysis: A Green Catalytic Tool to Cleave Carbon–Carbon Double Bonds

Bidange

Fischmeister

Bruneau

2016

Chemistry A European J

120

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Remarkable innovations have been made in the field of olefin metathesis due to the design and preparation of new catalysts. Ethenolysis, which is cross-metathesis with ethylene, represents one catalytic transformation that has been used with the purpose of cleaving internal carbon-carbon double bonds. The objectives were either the ring opening of cyclic olefins to produce dienes or the shortening of unsaturated hydrocarbon chains to degrade polymers or generate valuable shorter terminal olefins in a controlled manner. This Review summarizes several aspects of this reaction: the catalysts, their degradation in the presence of ethylene, some parameters driving their productivity, the side reactions, and the applications of ethenolysis in organic synthesis and in potential industrial applications.

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“…It is worth mentioning that mostly the catalyst systems supported on either alumina or silica‐alumina supports have been reported for heterogeneous metathesis of unsaturated fatty acid derivatives . Sibeijn et al investigated the activity of Re 2 O 7 species supported either on Al 2 O 3 or SiO 2 .Al 2 O 3 , after promoting with tetraalkyltin, in the ethenolysis of methyl oleate . Though both compositions were found to generate metathesis products, Re 2 O 7 /Al 2 O 3 appeared more active at higher methyl oleate/Re 2 O 7 molar ratios compared to Re 2 O 7 /SiO 2 .Al 2 O 3 (Figure ).…”

Section: Alkylidene‐free Heterogeneous Catalyst Systemsmentioning

confidence: 99%

“…Ethenolysis of methyl oleate − turnover number and conversion as a function of methyl oleate/Re 2 O 7 ratio: (a) 30 mg/g (3 wt%) Re 2 O 7 /SiO 2 .Al 2 O 3 ; (b) 180 mg/g (18 wt%) Re 2 O 7 /Al 2 O 3 (reproduced with permission) …”

Section: Alkylidene‐free Heterogeneous Catalyst Systemsmentioning

confidence: 99%

Heterogeneous olefin‐metathesis: Comparative perspective of the activity with respect to unsaturated fatty acid methyl esters

2017

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Olefin metathesis is one of the most exiting tools in synthetic chemistry that can explicitly be employed to produce higher value products from unsaturated fats and oil feedstock. Contrary to the early stage metathesis catalysts, being extremely sensitive to humidity and to the substrate functionalities, redesigned organometallic species not only exhibit greater activity and selectivity but also offer pronounced stability towards functional olefins and ambient atmosphere. Though a number of highly efficient homogeneous catalysts have been developed, these are generally costly and also lead to product contamination and, consequently, pose environmental concerns. Heterogeneous catalysis can be an alternate route; however it faces a number of hurdles such as support compatibility, multiple active sites, and abridged efficacy. Nevertheless, through careful designing, certain heterogeneous catalyst systems have been suggested for metathesis of functionalized olefins like fatty acid methyl esters (FAMEs). A number of metallic species such as organometallic compounds bearing metal‐alkylidene moieties (e.g. Grubbs‐/Schrock‐type systems), alkylidene‐free complexes (e.g. methyltrioxorhenium), and inorganic (W, Mo, Re) oxides/chlorides have been probed in this regard. Accordingly this mini review deals with the various aspects like heterogenization/immobilization, activity criteria, and reusability of such catalyst systems in the context of olefin metathesis of natural fats/oils derivatives.

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Ethenolysis of methyl oleate over supported Re-based catalysts

Cited by 29 publications

References 13 publications

Valorisation of vegetable oils via metathesis reactions on solid catalysts: Cross-metathesis of methyl oleate with 1-hexene

Valorisation of vegetable oils via metathesis reactions on solid catalysts: Cross-metathesis of methyl oleate with 1-hexene

Ethenolysis: A Green Catalytic Tool to Cleave Carbon–Carbon Double Bonds

Heterogeneous olefin‐metathesis: Comparative perspective of the activity with respect to unsaturated fatty acid methyl esters

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