US4174348A
Expired / Lapsed
US
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Preparation of cyclopropanecarbonitriles
Assignee: Shell Internationale Research Maatschappij BV
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Filing: 1978-05-30
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Granted: 1979-11-13
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Expires: 1998-05-30
Abstract
Abstract A novel process is disclosed for the preparation of cyclopropanecarbonitriles of the general formula: <IMAGE> (I) wherein R1, R2 and Hal have the meanings given in the description; which comprises heating the corresponding ammonium or aminium cyclopropanecarboxylate in the presence of a polar aprotic solvent. The process produces cyclopropanecarbonitriles, in high yields, which are useful as intermediates in the production of insecticidally active compounds.
Inventors
- 👤 Petrus A. Kramer
- 👤 Helena Austermuhle-Bertola
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 16:22
CPC Classifications
C; C07; C07C; C07C255/00; C07C255/45
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
87 words
A process for the preparation of a cyclopropanecarbonitrile of the general formula: ##STR5## wherein R 1 and R 1 each individually represent an alkyl group of from one to six carbon atoms and Hal represents a fluorine, chlorine or bromine atom; which comprises heating, in the presence of a polar aprotic solvent, a cyclopropanecarboxylate of the general formula: ##STR6## wherein R 1 , R 2 and Hal in general formula II have the same meanings as in general formula I and X represents a quaternary ammonium group.
Claim 2
Dependent Claim
87 words
A process for the preparation of a cyclopropanecarbonitrile of the general formula: ##STR5## wherein R 1 and R 1 each individually represent an alkyl group of from one to six carbon atoms and Hal represents a fluorine, chlorine or bromine atom; which comprises heating, in the presence of a polar aprotic solvent, a cyclopropanecarboxylate of the general formula: ##STR6## wherein R 1 , R 2 and Hal in general formula II have the same meanings as in general formula I and X represents a quaternary ammonium group.
Claim 3
Dependent Claim
18 words
The process according to claim 1 wherein the polar aprotic solvent is N,N-dimethylacetamide, dimethyl sulphoxide, N-methylpyrrolidone or acetonitrile.
Claim 4
Dependent Claim
13 words
The process according to claim 1 wherein the polar aprotic solvent is N,N-dimethylformamide.
Claim 5
Dependent Claim
25 words
The process according to claim 1, 2 or 3, wherein the quaternary ammonium group is an ammonium, pyridinium, quinolinium, isoquinolinium, n-hexylaminium, anilinium, N-methylanilinium, or N,N-dimethylanilinium.
Claim 6
Dependent Claim
27 words
The process according to claim 1, 2 or 3, wherein heating is effected at a temperature in the range of from about 100° to about 200° C.
Claim 7
Dependent Claim
25 words
The process according to claim 4 wherein heating is effected at a temperature in the range of from about 100° C. to about 200° C.
Claim 8
Dependent Claim
75 words
A process for the preparation of a cyclopropanecarbonitrile of the general formula: ##STR7## wherein R 1 and R 2 each individually represents an alkyl group of from one to six carbon atoms and Hal represents a fluorine, chlorine or bromine atom; which comprises (a) contacting a carboxylic acid of the general formula ##STR8## with ammonia or an amine to form a cyclopropanecarboxylate, and (b) heating the cyclopropanecarboxylate in the presence of a polar aprotic solvent.
Claim 9
Dependent Claim
75 words
A process for the preparation of a cyclopropanecarbonitrile of the general formula: ##STR7## wherein R 1 and R 2 each individually represents an alkyl group of from one to six carbon atoms and Hal represents a fluorine, chlorine or bromine atom; which comprises (a) contacting a carboxylic acid of the general formula ##STR8## with ammonia or an amine to form a cyclopropanecarboxylate, and (b) heating the cyclopropanecarboxylate in the presence of a polar aprotic solvent.
References Cited (Backward Citations)
US4000180A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-11-12 | 1983-05-14 | 1983-11-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-11-12 | 1987-05-14 | 1987-11-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-11-12 | 1991-05-14 | 1991-11-13 | $7700.00 | Window Closed / Lapsed |