Patent US4141915A successfully refreshed from Google Patents.
US4141915A
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Method of preparing α-substituted cyanoacetic acid alkyl esters
Assignee: Dynamit Nobel AG
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Filing: 1977-08-30
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Granted: 1979-02-27
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Expires: 1997-08-30
Abstract
Abstract A process for preparing an α-substituted cyanoacetic acid alkyl ester which comprises contacting an unsaturated nitrile of the formula ##STR1## wherein R 2 is a hydrogen atom or a methyl group and R 3 is CH 2 , CHCH 3 , CHCN, CHC 6 H 5 or C(CH 3 ) 2 with an alcohol of the formula ROH II wherein R is a primary, secondary or tertiary saturated alkyl moiety of 1 to 20 carbon atoms and carbon monoxide in the presence of Co 2 (CO) 8 and an α-substituted pyridine in the absence of hydrogen at an elevated temperature and pressure.
Inventors
- 👤 Moustafa El-Chahawi
- 👤 Uwe Prange
- 👤 Hermann Richtzenhain
- 👤 Wilhelm Vogt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 18:33
CPC Classifications
C; C07; C07C; C07C255/00
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
187 words
A process for preparing an α-substituted cyanoacetic acid alkyl ester of the formula ##STR6## wherein R is a primary, secondary or tertiary saturated alkyl moiety of 1 to 20 carbon atoms, R 1 is methyl, ethyl, isopropyl, cyanomethyl or benzyl, R 2 is hydrogen or methyl which comprises contacting an α,β-unsaturated nitrile of the formula ##STR7## wherein R 2 has the previously assigned significance and R 3 is CH 2 , CHCH 3 , CHCN, CHC 6 H 5 or C(CH 3 ) 2 with an alcohol of the formula ROH II wherein R has the previously assigned significance and carbon monoxide in the presence of Co 2 (CO) 8 and an α-substituted pyridine which has the formula ##STR8## wherein X is a primary or secondary or tertiary alkyl moiety of 1 to 4 carbon atoms, which can be olefinically unsaturated, or a benzyl moiety which can be alkyl-substituted, or halogen or a phenyl moiety, or an alpha-pyridyl moiety, Y is a C 1 to C 4 alkyl moiety or halogen, a is 0 to 2 in the absence of hydrogen at an elevated temperature and pressure.
Claim 2
Dependent Claim
187 words
A process for preparing an α-substituted cyanoacetic acid alkyl ester of the formula ##STR6## wherein R is a primary, secondary or tertiary saturated alkyl moiety of 1 to 20 carbon atoms, R 1 is methyl, ethyl, isopropyl, cyanomethyl or benzyl, R 2 is hydrogen or methyl which comprises contacting an α,β-unsaturated nitrile of the formula ##STR7## wherein R 2 has the previously assigned significance and R 3 is CH 2 , CHCH 3 , CHCN, CHC 6 H 5 or C(CH 3 ) 2 with an alcohol of the formula ROH II wherein R has the previously assigned significance and carbon monoxide in the presence of Co 2 (CO) 8 and an α-substituted pyridine which has the formula ##STR8## wherein X is a primary or secondary or tertiary alkyl moiety of 1 to 4 carbon atoms, which can be olefinically unsaturated, or a benzyl moiety which can be alkyl-substituted, or halogen or a phenyl moiety, or an alpha-pyridyl moiety, Y is a C 1 to C 4 alkyl moiety or halogen, a is 0 to 2 in the absence of hydrogen at an elevated temperature and pressure.
Claim 3
Dependent Claim
27 words
A process according to claim 1 wherein the reaction is conducted at a temperature between 100° and 250° C. under an elevated pressure up to 250 bars.
Claim 4
Dependent Claim
20 words
A process according to claim 2 wherein the process is conducted under carbon monoxide pressure of 50 to 250 bars.
Claim 5
Dependent Claim
21 words
A process according to claim 3 wherein the process is conducted at a carbon monoxide pressure of 100 to 180 bars.
Claim 6
Dependent Claim
19 words
A process according to claim 3 wherein the process is conducted at a temperature between 120° and 220° C.
Claim 7
Dependent Claim
23 words
A process according to claim 2 wherein R is a primary, secondary, or tertiary saturated alkyl moiety of 1 to 4 carbon atoms.
Claim 8
Dependent Claim
19 words
A process according to claim 2 wherein said α-substituted pyridine is α-picoline, 2,4-lutidine, 2,6-lutidine, 2,4,6-collidine, 2-ethylpyridine, 2-vinylpyridine or 2-chloropyridine.
Claim 9
Dependent Claim
19 words
A process according to claim 2 wherein the molar ratio of α-substituted pyridine to nitrile is 1:1 to 1:100.
Claim 10
Dependent Claim
19 words
A process according to claim 8 wherein the molar ratio of α-substituted pyridine to nitrile is 1:10 to 1:50.
Claim 11
Dependent Claim
75 words
A process according to claim 2 wherein the α-substituted pyridine has the formula ##STR9## wherein a is 0 to 2, X is a primary, secondary or tertiary alkyl moiety of 1 to 4 carbon atoms which can be olefinically unsaturated or a benzyl moiety which can be alkyl-substituted or halogen or a phenyl moiety or an α-pyridyl moiety, and Y is a primary, secondary or tertiary saturated C 1 -C 4 alkyl moiety or halogen.
Claim 12
Dependent Claim
20 words
A process according to claim 10 wherein the Y substituents are in the 4- and/or 6-position on the pyridine nucleus.
Claim 13
Dependent Claim
32 words
A process according to claim 10 wherein the α-substituted pyridine is α-picoline, 2,4-lutidine, 2,6-lutidine, 2,4,6-collidine, 2-ethylpyridine, 2-n-propyl- and 2-isopropylpyridine, 2-n-butyl- and 2-tert.-butylpyridine, 2-vinylpyridine, 2-propenylpyridine, 2-chloropyridine, 2-bromo- or 2-iodopyridine, 2-benzylpyridine, 2-phenylpyridine and α,α'-bipyridyl.
Claim 14
Dependent Claim
38 words
A process according to claim 2 wherein the Co 2 (CO) 8 is employed in a molar amount with respect to said nitrile such that the ratio of Co 2 (CO) 8 to nitrile is 1:10 to 1:1000.
Claim 15
Dependent Claim
21 words
A process according to claim 13 wherein the molar ratio of Co 2 (CO) 8 to nitrile is 1:50 to 1:500.
Claim 16
Dependent Claim
19 words
A process according to claim 2 wherein the process is carried out in a closed vessel at autogeneous pressure.
Claim 17
Dependent Claim
17 words
A process according to claim 2 wherein said alcohol is ethanol, methanol, isopropanol, tertiary butanol, or 2-ethylhexanol.
Claim 18
Dependent Claim
32 words
A process according to claim 1 wherein said alpha-substituted pyridine is alpha-picoline, 2,4-lutidine, 2,6-lutidine, 2,4,6-collidine, 2-ethylpyridine, 2-n-propyl- and 2-isopropylpyridine, 2-n-butyl- and 2-tert.-butylpyridine, 2-vinylpyridine, 2-propenylpyridine, 2-chloropyridine, 2-bromo- and 2-iodopyridine, 2-benzylpyridine, 2-phenylpyridine or alpha-alpha'-bipyridyl.
Claim 19
Dependent Claim
32 words
A process according to claim 1 wherein said alpha-substituted pyridine is alpha-picoline, 2,4-lutidine, 2,6-lutidine, 2,4,6-collidine, 2-ethylpyridine, 2-n-propyl- and 2-isopropylpyridine, 2-n-butyl- and 2-tert.-butylpyridine, 2-vinylpyridine, 2-propenylpyridine, 2-chloropyridine, 2-bromo- and 2-iodopyridine, 2-benzylpyridine, 2-phenylpyridine or alpha-alpha'-bipyridyl.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-02-26 | 1982-08-28 | 1983-02-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-02-26 | 1986-08-28 | 1987-02-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-02-26 | 1990-08-28 | 1991-02-27 | $7700.00 | Window Closed / Lapsed |