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US4156785A
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Method of preparing α,β-unsaturated carboxylic acid esters
Assignee: Dynamit Nobel AG
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Filing: 1975-07-28
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Granted: 1979-05-29
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Expires: 1995-07-28
Abstract
Abstract Process of preparing an alpha , beta -unsaturated carboxylic acid ester, comprising contacting an alpha , beta -unsaturated halogen compound with carbon monoxide, an alkali alcoholate in the presence of a metal carbonyl as catalyst, in an alcohol that is the basis of the alkali alcoholate, at a pH of 8.5-11.5. Thereby, for example, crotonic acid methyl ester can be produced from allyl chloride.
Inventors
- 👤 Uwe Prange
- 👤 Hermann Richtzenhain
- 👤 Wilhelm Vogt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 01:21
CPC Classifications
C; C07; C07C; C07C69/00; C07C69/52
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
75 words
Process of preparing an α,β-unsaturated carboxylic acid ester, comprising contacting an α,β-unsaturated halogen compound with carbon monoxide, an alkali alcoholate and in the presence of a catalystic amount of nickel or cobalt carbonyl in an alcohol that is the basis of the alkali alcoholate in a pH range between 8.5 and 11.5, at a temperature and for a time sufficient for the reaction of said α,β-unsaturated halogen compound to form said α,β-unsaturated carboxylic acid ester.
Claim 2
Dependent Claim
75 words
Process of preparing an α,β-unsaturated carboxylic acid ester, comprising contacting an α,β-unsaturated halogen compound with carbon monoxide, an alkali alcoholate and in the presence of a catalystic amount of nickel or cobalt carbonyl in an alcohol that is the basis of the alkali alcoholate in a pH range between 8.5 and 11.5, at a temperature and for a time sufficient for the reaction of said α,β-unsaturated halogen compound to form said α,β-unsaturated carboxylic acid ester.
Claim 3
Dependent Claim
22 words
Process of claim 1, wherein said metal carbonyl and α,β-unsaturated halogen compound are present in the molar ratio of 1:10 to 1:500.
Claim 4
Dependent Claim
21 words
Process of claim 1, wherein said alcohol is a primary, secondary or tertiary univalent alcohol having 1 to 20 carbon atoms.
Claim 5
Dependent Claim
12 words
Process of claim 1, wherein said alcoholate is sodium or potassium alcoholate.
Claim 6
Dependent Claim
10 words
Process of claim 1, wherein the temperature is 0°-100° C.
Claim 7
Dependent Claim
19 words
Process of claim 1, wherein the contacting is performed at a carbon monoxide pressure of 0.5 to 5 atmospheres.
Claim 8
Dependent Claim
99 words
Process of claim 1 wherein said α,β-unsaturated halogen compound is an allyl halide of the formula: ##STR2## and said α,β-unsaturated carboxylic acid ester is of the formula ##STR3## R 1 , R 2 , R 3 and R 4 is each hydrogen, alkyl, cycloalkyl, aryl, or aryl-substituted alkyl radical having 1 to 20 carbon atoms, with the proviso that R 1 and R 3 or R 4 may represent a component of cycloalkyl having 3 to 20 carbon atoms; X is chlorine, bromine, or iodine; and R is straight chained or branched alkyl having 1 to 20 carbon atoms.
Claim 9
Dependent Claim
74 words
Process of claim 7, wherein the catalyst is a nickel or cobalt carbonyl, said metal carbonyl and α,β-unsaturated halogen compound are present in the molar ratio of 1:10 to 1:50, said alcohol is a primary, secondary or tertiary univalent alcohol having 1 to 20 carbon atoms, said alcoholate is sodium or potassium alcoholate, the temperature zone is 0°-100° C., and the contacting is performed at a carbon monoxide pressure of 0.5 to 5 atmospheres.
Claim 10
Dependent Claim
14 words
Process of claim 1, wherein water or alkali hydroxide is present during said contacting.
Claim 11
Dependent Claim
19 words
Process of claim 1, wherein alkali hydroxide in amount of 0.01 to 5.0 wt.% is present during said contacting.
Claim 12
Dependent Claim
18 words
Process of claim 1, wherein said contacting is in the presence of a catalytic amount of nickel carbonyl.
Claim 13
Dependent Claim
18 words
Process of claim 1, wherein said contacting is in the presence of a catalytic amount of cobalt carbonyl.
References Cited (Backward Citations)
US3116306A
Cited
US3974202A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-05-28 | 1982-11-27 | 1983-05-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-05-28 | 1986-11-27 | 1987-05-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-05-28 | 1990-11-27 | 1991-05-29 | $7700.00 | Window Closed / Lapsed |