Process for the preparation of beta-gamma unsaturated esters

Details Process for the preparation of beta-gamma unsaturated esters Process for the preparation of beta-gamma unsaturated esters

C - Chemistry, Metallurgy

07

C

C07C 67/37 (2006.01) C07C 67/38 (2006.01) C07C 69/533 (2006.01)

Patent

CA 2347451

A process for the carbonylation of allylic butenyl ether (e.g., methyl crotyl ether, 3-methoxybutene-1 and mixtures thereof) or mixture of butadiene and alcohol (e.g., methanol) and production of beta-gamma unsaturated carboxylic acid esters (e.g., methyl-3-pentenoate) utilizing a rhodium-containing catalyst (e.g., dicarbonylacetylacetonate rhodium(I) or the like) promoted with an iodide-containing compound (e.g., HI, AlI3, SnI4, TiI4, CrI3, and CoI2 or the like). Such a process is particularly useful in the production of difunctional monomers and intermediates in the synthesis of adipic acid. The representative reaction showing (a) butadiene in the presence of methanol under catalytic reaction conditions producing the 3-methoxybutene-1 intermediate (a positional isomer of methyl crotyl ether) which is then combined with carbon monoxide to produce methyl pentenoate is illustrative of the overall carbonylation.

L'invention concerne un procédé de carbonylation de butényl éther allylique (notamment le méthyl crotyl éther, 3-méthoxybutène-1 et leurs mélanges) ou de mélange de butadiène et d'alcool (p. ex, le méthanol) et de production de esters d'acide carboxylique béta-gamma insaturés (p. ex., le méthyl-3-penténoate) au moyen d'un catalyseur contenant du rhodium (p. ex., le dicarbonylacetylacétonate rhodium(I) ou analogue) activé par un composé contenant du iodure (p.ex., HI, AlI¿3?, SnI¿4?, TiI¿4?, CrI¿3?, et CoI¿2? ou analogue). Un tel procédé est particulièrement utile dans la production de monomères difonctionnels et d'intermédiaires dans la synthèse de l'acide adipique. La réaction représentative (a), dans laquelle un butadiène est en présence du méthanol dans des conditions de réaction catalytique permettant de produire l'intermédiaire 3-méthoxybutène-1 (un isomère positionnel de méthyl crotyl éther) qui est ensuite combiné avec un monoxyde de carbone afin d'obtenir un méthyl penténoate, illustre bien la carbonylation dans sa globalité.

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