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1. WO2000037411 - PROCESS FOR THE PREPARATION OF BETA-GAMMA UNSATURATED ESTERS

Publication Number WO/2000/037411
Publication Date 29.06.2000
International Application No. PCT/US1999/028247
International Filing Date 30.11.1999
Chapter 2 Demand Filed 10.07.2000
IPC
C07C 67/37 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
67Preparation of carboxylic acid esters
36by reaction with carbon monoxide or formates
37by reaction of ethers with carbon monoxide
C07C 67/38 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
67Preparation of carboxylic acid esters
36by reaction with carbon monoxide or formates
38by addition to an unsaturated carbon-to-carbon bond
CPC
C07C 67/37
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
67Preparation of carboxylic acid esters
36by reaction with carbon monoxide or formates
37by reaction of ethers with carbon monoxide
C07C 67/38
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
67Preparation of carboxylic acid esters
36by reaction with carbon monoxide or formates
38by addition to an unsaturated carbon-to-carbon bond
Applicants
  • E.I. DU PONT DE NEMOURS AND COMPANY [US]/[US]
  • DSM N.V. [NL]/[NL]
Inventors
  • BURKE, Patrick, Michael
Agents
  • STEVENSON, Robert, B.
Priority Data
09/215,40918.12.1998US
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) PROCESS FOR THE PREPARATION OF BETA-GAMMA UNSATURATED ESTERS
(FR) PROCEDE DE PREPARATION D'ESTERS INSATURES BETA-GAMMA
Abstract
(EN)
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.
(FR)
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, AlI3, SnI4, TiI4, CrI3, et CoI2 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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