US4028201A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Electrolytic monocarboxylation of activated olefins
Assignee: Monsanto Co
•
Filing: 1972-11-13
•
Granted: 1977-06-07
•
Expires: 1992-11-13
Abstract
Abstract Olefinic nitriles, esters and amides are electrolytically mono-carboxylated in the presence of carbon dioxide and a proton donor.
Inventors
- 👤 Donald Armon Tyssee
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 12:04
CPC Classifications
C; C25; C25B; C25B3/00; C25B3/20; C25B3/25; C25B3/01; C25B3/07; C25B3/09
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
65 words
The method of electrolytic carboxylation of alpha,beta-olefinic nitriles, esters and amides which comprises electrically reducing such olefinic compounds at the cathode, in an electrolysis medium comprising solvent and supporting electrolyte and in the presence of carbon dioxide and a small amount of water sufficient to direct the carboxylation substantially toward mono-carboxylation and recovering a product in which mono-carboxylation of the said olefinic compound has occurred.
Claim 2
Independent Claim
65 words
The method of electrolytic carboxylation of alpha,beta-olefinic nitriles, esters and amides which comprises electrically reducing such olefinic compounds at the cathode, in an electrolysis medium comprising solvent and supporting electrolyte and in the presence of carbon dioxide and a small amount of water sufficient to direct the carboxylation substantially toward mono-carboxylation and recovering a product in which mono-carboxylation of the said olefinic compound has occurred.
Claim 3
Dependent Claim
19 words
The method of claim 1 in which a molecule of carbon dioxide has been added at the β-carbon atom.
Claim 4
Dependent Claim
12 words
The method of claim 1 in which the olefinic compound is acrylonitrile.
Claim 5
Dependent Claim
13 words
The method of claim 1 in which acrylonitrile is converted to β-cyanopropionic acid.
Claim 6
Dependent Claim
23 words
The method of claim 1 in which the olefinic compound is provided at approximately the rate it is reacted under the electrolysis conditions.
Claim 7
Dependent Claim
13 words
The method of claim 1 in which an undivided electrolysis cell is employed.
Claim 8
Dependent Claim
27 words
The method of claim 1 in which the electrolysis is conducted in an aprotic solvent containing a quaternary ammonium salt and 0.5 to 15% by weight water.
Claim 9
Dependent Claim
18 words
The method of claim 7 in which the olefinic compound is acrylonitrile and the product is β-cyanopropionic acid.
Claim 10
Dependent Claim
34 words
The method of claim 1 in which the cathode potential was controlled to a value sufficient for but not greatly differing from that needed for reduction of the olefinic compound under the electrolysis conditions.
Claim 11
Dependent Claim
26 words
The method of claim 1 in which the concentration of olefinic reactant is no more than 10 times that of carbon dioxide on a molar basis.
Claim 12
Dependent Claim
39 words
The method of claim 1 in which an aprotic solvent containing a supporting electrolyte salt and a small amount of water is used as the electrolysis medium and the concentration of olefinic reactant therein does not exceed 1 molar.
Claim 13
Dependent Claim
16 words
The method of claim 1 in which the cathode is lead and the solvent is acetonitrile.
Claim 14
Dependent Claim
16 words
The method of claim 1 in which the cathode is lead and the solvent is dimethylformamide.
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) | 1980-06-06 | 1980-12-06 | 1981-06-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-06-06 | 1984-12-06 | 1985-06-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-06-06 | 1988-12-06 | 1989-06-07 | $7700.00 | Window Closed / Lapsed |