Cross-metathesis of unsaturated natural oils with 2-butene. High conversion and productive catalyst turnovers

Patel, Jim; Elaridi, Jomana; Jackson, W. Roy; Robinson, Andrea J.; Serelis, Algirdas K.; Such, Chris

doi:10.1039/b511626k

Cited by 61 publications

(29 citation statements)

References 17 publications

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“…For example, in the case of glycerol trioleate ethe-nolysis, the triglyceride of a-decenoic acid is the coproduct. [20][21][22][23][24][25] Although thesec oproducts are interesting bi-or trifunctional molecules with potentially valuable applications,t he overall yield of a-olefins is low,f or example, only 43 %w /w of glycerolt rioleate is converted into the desired high-value LAO. Similarly,m etathesis has been used widely to cleave fatty acid derivatives to lead to unsaturated long-chain a-olefins.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Decarbonylation of Biosourced Substrates

et al. 2015

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Linear α-olefins (LAO) are one of the main targets in the field of surfactants, lubricants, and polymers. With the depletion of petroleum resources, the production of LAO from renewable feedstocks has gained increasing interest in recent years. In the present study, we demonstrated that Ir catalysts were suitable to decarbonylate a wide range of biosourced substrates under rather mild conditions (160 °C, 5 h reaction time) in the presence of potassium iodide and acetic anhydride. The resulting LAO were obtained with good conversion and selectivity provided that the purity of the substrate, the nature of the ligand, and the amounts of the additives were controlled accurately. The catalytic system could be recovered efficiently by using a Kugelrohr distillation apparatus and recycled.

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Section: Introductionmentioning

confidence: 99%

Catalytic Decarbonylation of Biosourced Substrates

et al. 2015

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“…One of the major application of the cross metathesis of vegetal oils was presented by Patel et al in 2005. They showed that the cross-metathesis of synthetic and natural triglycerides containing unsaturated fatty acids with 2-butene can be achieved with high conversion and excellent productive turnovers [18]. These reactions are catalysed by second-generation ruthenium-based olefin metathesis catalysts and can be conducted at -5°C in liquid 2-butene.…”

Section: X Scheme 14 Alkene Ruthenium Catalysts Bearing An Ionic Tagmentioning

confidence: 98%

Alkene Metathesis and Renewable Materials: Selective Transformations of Plant Oils

Malacea¹,

Dixneuf

2010

Green Metathesis Chemistry

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The olefin metathesis of natural oils and fats and their derivatives is the basis of clean catalytic reactions relevant to green chemistry processes and the production of generate useful chemicals from renewable raw materials. Three variants of alkene metathesis: self-metathesis, ethenolysis and cross-metathesis applied to plant oil derivatives will show new routes to fine chemicals, bifunctional products, polymer precursours and industry intermediates.

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“…Hoveyda-Grubbs 2 nd generation catalyst was chosen as it gave better results in butenolysis reactions in organic solvent compared to Hoveyda-Grubbs 1 st generation catalyst. 18,39,40 Similar to the aforementioned ethenolysis in scCO 2 , the butenolysis was conducted at a pressure of 300 bar at a temperature of 45°C.…”

Section: Butenolysis Of Model Compounds and Microalgae Oilmentioning

confidence: 99%