US3956357A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Manufacture of 2-cyano-propionate esters
Assignee: Imperial Chemical Industries Ltd
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Filing: 1975-03-13
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Granted: 1976-05-11
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Expires: 1995-03-13
Abstract
Abstract A process for the manufacture of 2-cyano-propionate esters which comprises hydrogenating in the presence of an hydrogenating catalyst a mixture of a cyano-acetic ester, formaldehyde and a condensation catalyst. Typically ethyl cyano-acetate is treated with formalin or paraform and hydrogen in the presence of palladium on carbon and zinc acetate. Preferably an antioxidant or polymerisation inhibitor is also included in the reaction mixture which also usually includes solvents such as glacial acetic acid or toluene.
Inventors
- 👤 Albert Edward Kaye
- 👤 Alan Cyril Tucker
- 👤 Ronald James Hurlock
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 08:45
CPC Classifications
C; C07; C07C; C07C255/00
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
91 words
A process for the manufacture of a lower alkyl 2-cyano-propionate ester which comprises hydrogenating at a temperature of 15° to 80°C and in the presence of a hydrogenation catalyst, a reaction mixture of a cyano-acetic lower alkyl ester, formaldehyde and a condensation catalyst suitable for reacting formaldehyde with active methylene groups, and recovering the lower alkyl 2-cyanopropionate thus produced, hydrogen being introduced to the reaction mixture before the formaldehyde is added thereto and the hydrogenation catalyst being selected from the group consisting of palladium, platinum, rhodium, cobalt, ruthenium and Raney nickel.
Claim 2
Dependent Claim
91 words
A process for the manufacture of a lower alkyl 2-cyano-propionate ester which comprises hydrogenating at a temperature of 15° to 80°C and in the presence of a hydrogenation catalyst, a reaction mixture of a cyano-acetic lower alkyl ester, formaldehyde and a condensation catalyst suitable for reacting formaldehyde with active methylene groups, and recovering the lower alkyl 2-cyanopropionate thus produced, hydrogen being introduced to the reaction mixture before the formaldehyde is added thereto and the hydrogenation catalyst being selected from the group consisting of palladium, platinum, rhodium, cobalt, ruthenium and Raney nickel.
Claim 3
Dependent Claim
12 words
A process as claimed in claim 1 wherein the catalyst is palladium.
Claim 4
Dependent Claim
26 words
A process as claimed in claim 1 in which the formaldehyde is added in the form of a derivative which yields formaldehyde under the reaction conditions.
Claim 5
Dependent Claim
15 words
A process as claimed in claim 1 wherein the condensation catalyst is a basic material.
Claim 6
Dependent Claim
29 words
A process as claimed in claim 4 in which the condensation catalyst is ammonia or an amine or an organic acid salt thereof or a basic ion exchange resin.
Claim 7
Dependent Claim
15 words
A process as claimed in claim 1 wherein the condensation catalyst is an acidic material.
Claim 8
Dependent Claim
20 words
A process as claimed in claim 5 in which the condensation catalyst is an organic acid or a metallic salt.
Claim 9
Dependent Claim
16 words
A process as claimed in claim 1 wherein the condensation catalyst is a Friedel-Crafts type catalyst.
Claim 10
Dependent Claim
19 words
A process as claimed in claim 1 when carried out in the presence of an antioxidant or polymerisation inhibitor.
Claim 11
Dependent Claim
49 words
A process as claimed in claim 1 wherein the condensation catalyst is selected from the group consisting of ammonia, piperidine, diethylamine, salts of piperidine or diethylamine with acetic acid, butyric acid or oxalic acid, zinc chloride, zinc acetate, magnesium chloride, barium chloride, ferric chloride, aluminum chloride, or acetic acid.
References Cited (Backward Citations)
US3173939A
Cited
US3350439A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-05-11 | 1979-11-10 | 1980-05-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-05-11 | 1983-11-10 | 1984-05-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-05-11 | 1987-11-10 | 1988-05-11 | $7700.00 | Window Closed / Lapsed |