Commercial Potential of Olefin Metathesis of Renewable Feedstocks

Nickel, Andrew; Pederson, Richard L.

doi:10.1002/9781118711613.ch11

Cited by 23 publications

(16 citation statements)

References 55 publications

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“…[93c] To obtain an economically viable process, it was stated that a TON >50 000 is required for the ethenolysis of 2 b , based on the cost of the homogeneous catalyst. [93a] The most promising results have been obtained with Ru catalysts such as C2 and C3 bearing cyclic (amino)alkylcarbene (CAAC) ligands (Scheme 18 ). [101] TONs of 180 000 using 99.95 % pure ethene have been achieved at a catalyst loading of 3 ppm.…”

Section: Low‐molecular‐weight Products: Syntheses New Reactions and Platform Chemicalsmentioning

confidence: 99%

Fatty Acids and their Derivatives as Renewable Platform Molecules for the Chemical Industry

et al. 2021

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Oils and fats of vegetable and animal origin remain an important renewable feedstock for the chemical industry. Their industrial use has increased during the last 10 years from 31 to 51 million tonnes annually. Remarkable achievements made in the field of oleochemistry in this timeframe are summarized herein, including the reduction of fatty esters to ethers, the selective oxidation and oxidative cleavage of C–C double bonds, the synthesis of alkyl‐branched fatty compounds, the isomerizing hydroformylation and alkoxycarbonylation, and olefin metathesis. The use of oleochemicals for the synthesis of a great variety of polymeric materials has increased tremendously, too. In addition to lipases and phospholipases, other enzymes have found their way into biocatalytic oleochemistry. Important achievements have also generated new oil qualities in existing crop plants or by using microorganisms optimized by metabolic engineering.

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Section: Low‐molecular‐weight Products: Syntheses New Reactions and Platform Chemicalsmentioning

confidence: 99%

Fatty Acids and their Derivatives as Renewable Platform Molecules for the Chemical Industry

et al. 2021

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“…1 Although the existing technology already in use in a plant located in Gresik, Indonesia, and planned for a new facility in Lahad Datu, Malaysia, is based on the CM of a palm oil with 1-butene (butenolysis), 2 the alternative process of ethenolysis is seen to be preferred industrially as it produces a less complicated product mixture, containing a higher amount of valuable 9-decenoic acid 9-DA ( 1 , Scheme 1). 3 Therefore, ethenolysis of methyl oleate ( 2a )—the widely used model of natural fatty acid glycerol esters—became a widely studied transformation in the recent years. 4 Many research groups tried to develop the optimal reaction conditions and find the best catalyst for this process.…”

Section: Introductionmentioning

confidence: 99%

Looking for the Noncyclic(amino)(alkyl)carbene Ruthenium Catalyst for Ethenolysis of Ethyl Oleate: Selectivity Is on Target

et al. 2018

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A wide set of 65 diverse Ru metathesis catalysts was investigated in the ethenolysis reaction of biosourced ethyl oleate to allow the comparison between the catalyst structure and its activity and selectivity. Handling of the oleic substrate, weighing of the catalysts, and charging the reactor were done in air, with exclusion of a glovebox or Schlenk techniques. A catalyst bearing the unsymmetrical N-heterocyclic ligand featuring a thiophene fragment ( Ru-63 ) was selected to offer the best combination between high selectivity and sufficient activity under conditions mimicking oil industry practice. A proof-of-concept large-scale ethenolysis experiment was also done with the selected catalyst to prove its high selectivity at the 1 L scale reaction with a 90% pure non-distilled substrate.

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“…Olefin metathesis is a powerful method for the construction of C=C bonds in a large number of synthetic contexts, including target oriented synthesis, 1 polymer chemistry, 2 and renewable feedstock derivatization. 3 Extensive efforts have been made to design tailored catalysts for each application. 4 The development of asymmetric olefin metathesis catalysts has enabled the synthesis of enantioenriched compounds containing olefin functional groups, which are useful functional handles for further transformations.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Olefin Metathesis with Cyclometalated Ruthenium Complexes

2014

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The success of enantioselective olefin metathesis relies on the design of enantioenriched alkylidene complexes capable of transferring stereochemical information from the catalyst structure to the reactants. Cyclometalation of the NHC ligand has proven to be a successful strategy to incorporate stereogenic atoms into the catalyst structure. Enantioenriched complexes incorporating this design element catalyze highly Z- and enantioselective asymmetric ring opening/cross metathesis (AROCM) of norbornenes and cyclobutenes, and the difference in ring strain between these two substrates leads to different propagating species in the catalytic cycle. Asymmetric ring closing metathesis (ARCM) of a challenging class of prochiral trienes has also been achieved. The extent of reversibility and effect of reaction setup was also explored. Finally, promising levels of enantioselectivity in an unprecedented Z-selective asymmetric cross metathesis (ACM) of a prochiral 1,4-diene was demonstrated.

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Commercial Potential of Olefin Metathesis of Renewable Feedstocks

Cited by 23 publications

References 55 publications

Fatty Acids and their Derivatives as Renewable Platform Molecules for the Chemical Industry

Fatty Acids and their Derivatives as Renewable Platform Molecules for the Chemical Industry

Looking for the Noncyclic(amino)(alkyl)carbene Ruthenium Catalyst for Ethenolysis of Ethyl Oleate: Selectivity Is on Target

Enantioselective Olefin Metathesis with Cyclometalated Ruthenium Complexes

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