- Tandem catalytic acrylonitrile cross-metathesis and hydrogenation of nitriles with ruthenium catalysts: Direct access to linear α,ω- aminoesters from renewables
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Fraternité, Solidarité & complémentarité en Catalyse: Tandem alkene cross-metathesis of acrylonitrile with long-chain alkene and hydrogenation catalysis is performed by using a single ruthenium-alkylidene catalyst precursor. The protocol allows the catalytic transformation of unsaturated fatty acids, derivatives of plant oils, into α,ω-aminoesters. A key step involves the reduction of nitrile-ester intermediates into aminoesters, the precursors of polyamides, with alkene metathesis catalyst residue under mild conditions. Copyright
- Miao, Xiaowei,Fischmeister, Cédric,Bruneau, Christian,Dixneuf, Pierre H.,Dubois, Jean-Luc,Couturier, Jean-Luc
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- COMBINED SYNTHESIS OF A NITRILE-ESTER/ACID AND OF A DIESTER/DIACID
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A method for the combined synthesis of a mono-unsaturated nitrile-ester(acid) and of a bi-functional carbonyl compound, wherein it includes a step including the cross metathesis mc1 of an unsaturated fatty acid/ester compound with an unsaturated nitrile compound, in which mc1 is performed with partial conversion such as to obtain and recover, separately, at least the following products: a mono-unsaturated nitrile-ester/acid and a symmetrical compound, diester or diacid respectively including a double bond located in the middle of the molecular chain of compound, and subsequently a step including the oxidation cleavage cp2 of the double bond of compound, such as to form a single type of carbonyl compound having formula R2-(CH2)n-COR′, in which R′ is H or OH, depending on the operating conditions selected for the oxidation cleavage cp2. Also, the production of monomers for the polymer industry.
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Paragraph 0132-0136
(2016/03/13)
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- CROSS METATHESIS PROCESS
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A process for the synthesis of an unsaturated product by cross metathesis between a first unsaturated compound having at least 8 carbon atoms and a second unsaturated compound having less than 8 carbon atoms, the first unsaturated compound being capable of producing an unsaturated coproduct comprising more than 14 carbon atoms, by homometathesis, said process including at least one production phase which includes: feeding a reactor with the first unsaturated compound; feeding the reactor with the second unsaturated compound; feeding the reactor with at least a first metathesis catalysts, then feeding the reactor with at least a second metathesis catalyst; withdrawing a product stream arising from the reactor; the turnover number of the first catalyst being higher than the turnover number of the second catalyst so as to achieve the same target degree of conversion of the first unsaturated compound.
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Page/Page column 0188-0197
(2016/01/09)
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- CROSS METATHESIS PROCESS
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A process for the synthesis of an unsaturated product by cross metathesis between a first unsaturated compound having at least 8 carbon atoms and a second unsaturated compound having less than 8 carbon atoms, including: feeding a reactor with the first unsaturated compound, the second unsaturated compound and a metathesis catalyst; withdrawing an output stream, at the output of the reactor; separating the output stream, making it possible to recover at least: on the one hand, the unsaturated product and, on the other hand, the first unsaturated compound and the second unsaturated compound; recycling the first unsaturated compound and the second unsaturated compound to the reactor; in which the first unsaturated compound is capable of producing an unsaturated coproduct, including at least 14 carbon atoms, by homometathesis; and in which the flow rates for feeding the reactor with first unsaturated compound and with second unsaturated compound are adjusted.
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Paragraph 0214-0216
(2015/12/30)
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- Cross-metathesis approach to produce precursors of nylon 12 and nylon 13 from microalgae
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A two-step synthesis for producing methyl 12-aminododecanoate and 13-aminotridecanoate, the precursors of nylon 12 and nylon 13, from methyl oleate is described. First, methyl 11-cyano-9-undecenoate or 12-cyano-9-dodecenoate were prepared by cross metathesis of methyl oleate with either allyl cyanide or homoallyl cyanide, respectively. Subsequently, all the unsaturation of the two intermediates was hydrogenated to deliver the final products. This method represents the first synthesis of nylon 12 and 13 precursors from methyl oleate, an ester of an abundant and renewable natural fatty acid present in vegetable oil or microalgae. It also represents the shortest synthesis of nylon precursors from fatty acids, and as demonstrated in this study, can be directly applied to crude fatty acid methyl ester extracts from microalgae.
- Ameh Abel, Godwin,Oliver Nguyen, Kim,Viamajala, Sridhar,Varanasi, Sasidhar,Yamamoto, Kana
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p. 55622 - 55628
(2015/02/02)
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- Renewable materials as precursors of linear nitrile-acid derivatives via cross-metathesis of fatty esters and acids with acrylonitrile and fumaronitrile
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The cross-metathesis of fatty acids and esters, as renewable raw materials, with acrylonitrile and fumaronitrile is presented. The cross-metathesis reactions of both terminal and internal double bond containing compounds were performed using a ruthenium c
- Malacea, Raluca,Fischmeister, Cedric,Bruneau, Christian,Dubois, Jean-Luc,Couturier, Jean-Luc,Dixneuf, Pierre H.
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supporting information; experimental part
p. 152 - 155
(2010/04/22)
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