Abstract Esters of methacrylic acid or acrylic acid are produced by the oxidative carbonylation of propylene or ethylene by contacting the olefin, oxygen and carbon monoxide in the presence of an alcohol, a Group VIII noble metal catalyst and, as a cocatalyst, an alkyl, cycloalkyl, aromatic or heterocyclic compound containing an oxide of nitrogen preferably in an aromatic or heterocyclic ring. The oxidation can also be performed in the presence of a redox agent. In a typical embodiment the olefin, carbon monoxide and oxygen are contacted with an alcoholic solution of Group VIII noble metal at a concentration from 0.001 to 1.0 molar, a nitrogen oxide compound, pyridine 1-oxide, at a concentration from 0.01 to 25 weight percent and a redox agent, cupric chloride, at a concentration from 1 to about 35 weight percent. The carbon monoxide partial pressure used is from 10 to about 70 percent of the total pressure which is from 300 to 3,000 p.s.i.g. Under these conditions a substantial portion of the product comprises the desired ester of methacrylic acid.
Inventors
👤 Donald N Brattesani
Bibliographic Details
Application Number—
JurisdictionUS
Data Sourcegoogle_patents
Last Synchronized2026-10-30 04:17
CPC Classifications
C; C07; C07C; C07C67/00; C07C67/36; C07C67/38
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
11 words
The oxidative carbonylation of claim 1 wherein said olefin is propylene.
Claim 2
Dependent Claim
11 words
The oxidative carbonylation of claim 1 wherein said olefin is ethylene.
Claim 3
Dependent Claim
38 words
The oxidative carbonylation of claim 1 wherein said catalyst also contains a redox agent selected from the class consisting of salts of multivalent metals and C1-C5 alkyl and halo substituted quinones having from six to about 15 carbons.
Claim 4
Dependent Claim
14 words
The oxidative carbonylation of claim 1 wherein said cocatalyst is a heterocyclic nitrogen oxide.
Claim 5
Dependent Claim
12 words
The oxidative carbonylation of claim 5 wherein said cocatalyst is pyridine oxide.
Claim 6
Dependent Claim
12 words
The oxidative carbonylation of claim 1 wherein said cocatalyst is a nitroaromatic.
Claim 7
Dependent Claim
11 words
The oxidative carbonylation of claim 7 wherein said cocatalyst is nitronaphthalene.
Claim 8
Dependent Claim
25 words
The oxidative carbonylation of claim 1 wherein said olefin and carbon monoxide are contacted with a liquid reaction medium containing said alcohol, catalyst and cocatalyst.
Claim 9
Dependent Claim
25 words
The oxidative carbonylation of claim 1 wherein oxygen is also contacted with said platinum group metal to maintain said metal at said elevated oxidation state.
Claim 10
Dependent Claim
142 words
The oxidative carbonylation of an olefin selected from the class consisting of propylene and ethylene which comprises contacting said olefin, oxygen, carbon monoxide and a monohydroxy alcohol having from one to about 20 carbons in the presence of a catalyst comprising a Group VIII noble metal in an elevated oxidation state, a redox agent comprising a multivalent metal salt having an oxidation potential more positive than said Group VIII noble metal and from 0.01 to 25 weight percent of a cocatalyst selected from the class consisting of aromatic, saturated aliphatic and alicyclic and heterocyclic nitro and nitroso compounds having from one to about 15 carbons, at conditions comprising a temperature from about 25* to about 300* C. and a pressure from atmospheric to about 2,500 p.s.i.g., sufficient to replace a hydrogen on an unsaturated carbon of said olefin with an alkoxycarbonyl group.