173602-45-4Relevant academic research and scientific papers
Ruthenium-alkylidene catalysed cross-metathesis of fatty acid derivatives with acrylonitrile and methyl acrylate: A key step toward long-chain bifunctional and amino acid compounds
Miao,Malacea,Fischmeister,Bruneau,Dixneuf
, p. 2911 - 2919 (2011)
The ruthenium catalysed cross-metathesis of fatty-esters arising from plant oils with acrylonitrile is presented. The resulting linear nitrile ester products have potential as new intermediates for polyamides synthesis. A series of commercially available catalysts are able to promote the transformation of methyl 10-undecenoate 1, dimethyl octadec-9-en-1,18-dioate 5 and methyl ricinoleate 9 with acrylonitrile and a protocol based on the slow addition of catalyst allowed TONs as high as 1900 (92% yield) to be reached for cross-metathesis with acrylonitrile. These cross-metathesis conditions have been applied to methyl acrylate and TONs up to 7600 were obtained.
USE OF RUTHENIUM COMPLEXES IN OLEFIN METATHESIS REACTION
-
Page/Page column 18-19, (2018/05/27)
The invention relates to the use of ruthenium complexes, which are homogeneous catalysts and/or precatalysts of the olefin metathesis reaction, which lead to the production of alkenes containing an internal (non-terminal) double C=C bond.
CROSS METATHESIS APPROACH TO C11-C13 FATTY-CHAIN AMINO ESTERS FORM OLEIC ACID DERIVATIVES
-
Paragraph 0059; 0060; 0061, (2016/05/24)
A concise method of producing nylon 11, 12, or 13 precursors from oleic acid or an ester of oleic acid is described. The method involves cross-metathesis reactions as the key C-C bond formation step. Subsequent steps are provided to convert the metathesis product to the corresponding nylon precursors. Also provided are the products of the method.
Alkylidene-ruthenium-tin catalysts for the formation of fatty nitriles and esters via cross-metathesis of plant oil derivatives
Miao, Xiaowei,Blokhin, Anton,Pasynskii, Alexandr,Nefedov, Sergey,Osipov, Sergey N.,Roisnel, Thierry,Bruneau, Christian,Dixneuf, Pierre H.
experimental part, p. 5257 - 5262 (2011/01/09)
The reaction of SnCl2 with the Ru-Cl bond of the Grubbs I catalyst RuCl2(=CHPh)(PCy3)2 (1) gives the complex {[Ru(=CHPh)(SnCl3)(PCy3)]2(μ-Cl) 3}-[HPCy3]+ (2), but containing two diethyl ether solvate molecules. The formal insertion of SnCl2 into one Ru-Cl bond of the Hoveyda II catalyst RuCl2(=CH-C 6H4OPri)(H2IMes) (3) (H 2IMes = N,N′-dimesityl-4,5-dihydroimidazol-2-ylidene) results in formation of the new complex RuCl(SnCl3)(=CH-C6H 4OPri)(H2IMes) (4). The X-ray analyses of 2 and 4 show the presence of very short Ru-Sn bonds (2.5834(9) A mean bond for 2 and 2.5925(12) A for 4) and the retention of short Ru=C bonds (1.895(10) and 1.825(8) A, respectively). Complex 4 shows an excellent catalytic activity for the cross-metathesis of plant oil derivatives, the C11 ω-unsaturated ester and aldehyde and the unsaturated C18 diester with acrylonitrile, and a good activity for their cross-metathesis with methyl acrylate. Good to excellent yield of α,ω-bifunctional compounds, precursors of polyesters and polyamides, were obtained. Complex 2 shows catalytic activity for the self-metathesis of C11 ω-unsaturated aldehyde at low concentration to produce C20 α,ω-dialdehyde.
