US3843709A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Preparation of cyclopropyl cyanide from 4-hlorobutyronitrile
Assignee: Gulf Research and Development Co
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Filing: 1973-10-15
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Granted: 1974-10-22
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Expires: 1993-10-15
Abstract
Abstract Cyclopropyl cyanide is prepared by reacting 4chlorobutyronitrile with a base in the presence of a polar, aprotic solvent. For example, the reaction of 4chlorobutyronitrile with sodium hydroxide in the presence of dimethyl sulfoxide produces cyclopropyl cyanide in high yield.
Inventors
- 👤 J Bacha
- 👤 C Selwitz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 11:03
CPC Classifications
C; C07; C07C; C07C253/00; C07C253/30; C07C255/00; C07C255/01; C07C255/19; C07C255/23; C07C255/31; C07C255/45; C07C255/46; C07C2601/00; C07C2601/02; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/582
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
128 words
A METHOD FOR PREPARING CYCLOPROPYL CYANIDE WHICH COMPRISES REACTING 4-CHLOROBUTYRONITRILE WITH A BASE SELECTED FROM ALKALI METAL HYDROXIDE OR LOWER ALKOXIDE HAVING FROM ONE TO ABOUT FOUR CARBON ATOMS; OR CALCIUM, BARIUM OR STRONTIUM OXIDE OR HYDROXIDE; OR MAGNESIUM OXIDE, HYDROXIDE OR LOWER ALKOXIDE HAVING FROM ONE TO ABOUT FOUR CARBON ATOMS; OR A MIXTURE THEREOF IN A POLAR, APROTIC SOLVENT AT A VOLUME RATIO OF THE POLAR, APROTIC SOLVENT TO THE 4-CHLOROBUTYRONITRILE OF BETWEEN ABOUT 1:1 AND ABOUT 100:1, A RATIO OF THE POLAR, APROTIC SOLVENT IN LITERS OF THE BASE IN MOLS OF BETWEEN ABOUT 0.05:1 AND ABOUT 20:1, AND A MOLAR RATIO OF THE BASE TO THE 4CHLOROBUTYRONITRILE OF BETWEEN ABOUT 0.5:1 AND ABOUT 2:1; AND AT A TEMPERATURE BETWEEN ABOUT 0* AND ABOUT 160*C.
Claim 2
Independent Claim
128 words
A METHOD FOR PREPARING CYCLOPROPYL CYANIDE WHICH COMPRISES REACTING 4-CHLOROBUTYRONITRILE WITH A BASE SELECTED FROM ALKALI METAL HYDROXIDE OR LOWER ALKOXIDE HAVING FROM ONE TO ABOUT FOUR CARBON ATOMS; OR CALCIUM, BARIUM OR STRONTIUM OXIDE OR HYDROXIDE; OR MAGNESIUM OXIDE, HYDROXIDE OR LOWER ALKOXIDE HAVING FROM ONE TO ABOUT FOUR CARBON ATOMS; OR A MIXTURE THEREOF IN A POLAR, APROTIC SOLVENT AT A VOLUME RATIO OF THE POLAR, APROTIC SOLVENT TO THE 4-CHLOROBUTYRONITRILE OF BETWEEN ABOUT 1:1 AND ABOUT 100:1, A RATIO OF THE POLAR, APROTIC SOLVENT IN LITERS OF THE BASE IN MOLS OF BETWEEN ABOUT 0.05:1 AND ABOUT 20:1, AND A MOLAR RATIO OF THE BASE TO THE 4CHLOROBUTYRONITRILE OF BETWEEN ABOUT 0.5:1 AND ABOUT 2:1; AND AT A TEMPERATURE BETWEEN ABOUT 0* AND ABOUT 160*C.
Claim 3
Dependent Claim
113 words
A method in accordance with claim 1 in which the polar, aprotic solvent is a sulfoxide defined by the formula R1(R2)S:O in which R1 and R2 are independently lower alkyl, phenyl or benzyl, or a chlorine substituted derivative thereof; a sulfone defined by the formula R3(R4)SO2 in which R3 and R4 are independently selected from lower alkyl and can be joined together in a cyclic compound having from three to eight members in the ring; a di-N-substituted carboxylic acid amide defined by the formula R5CONR6(R7) in which R5 is H or lower alkyl and R6 and R7 are independently lower alkyl; an N-lower alkyl alpha or beta pyrrolidone; hexamethylenephosphoramide or a mixture thereof.
Claim 4
Dependent Claim
24 words
A method for preparing cyclopropyl cyanide in accordance with claim 1 in which the polar, aprotic solvent is dimethyl sulfoxide, dimethylformamide, dimethylacetamide or sulfolane.
Claim 5
Dependent Claim
27 words
A method in accordance with claim 1 in which the volume ratio of the polar, aprotic solvent to the 4-chlorobutyronitrile is between about 5:1 and about 50:1.
Claim 6
Dependent Claim
30 words
A method in accordance with claim 1 in which the ratio of the polar, aprotic solvent in liters to the base in mols is between about 0.3:1 and about 5:1.
Claim 7
Dependent Claim
25 words
A method in accordance with claim 1 in which the molar ratio of the base to the 4-chlorobutyronitrile is between about 1:1 and about 1.5:1.
Claim 8
Dependent Claim
19 words
A method in accordance with claim 1 in which the temperature is between about 15* and about 145* C.
Claim 9
Dependent Claim
19 words
A method in accordance with claim 1 in which the temperature is between about 25* and about 125* C.
Claim 10
Independent Claim
90 words
A method for preparing cyclopropyl cyanide which comprises reacting 4-chlorobutyronitrile with sodium hydroxide in a solvent selected from dimethyl sulfoxide, dimethylformamide, dimethylacetamide or sulfolane at a volume ratio of the solvent to the 4-chlorobutyronitrile of between about 1:1 and about 100: 1, a ratio of the solvent in liters to the sodium hydroxide in mols of between about 0.05:1 and about 20:1, and a molar ratio of the sodium hydroxide to the 4-chlorobutyronitrile of between about 0.5:1 and about 2:1; and at a temperature between about 0* and about 160*C.
Claim 11
Independent Claim
90 words
A method for preparing cyclopropyl cyanide which comprises reacting 4-chlorobutyronitrile with sodium hydroxide in a solvent selected from dimethyl sulfoxide, dimethylformamide, dimethylacetamide or sulfolane at a volume ratio of the solvent to the 4-chlorobutyronitrile of between about 1:1 and about 100: 1, a ratio of the solvent in liters to the sodium hydroxide in mols of between about 0.05:1 and about 20:1, and a molar ratio of the sodium hydroxide to the 4-chlorobutyronitrile of between about 0.5:1 and about 2:1; and at a temperature between about 0* and about 160*C.
Claim 12
Dependent Claim
25 words
A method in accordance with claim 9 in which the solvent is dimethyl sulfoxide and the temperature is between about 15* and about 145* C.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1977-10-21 | 1978-04-22 | 1978-10-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1981-10-21 | 1982-04-22 | 1982-10-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1985-10-21 | 1986-04-22 | 1986-10-22 | $7700.00 | Window Closed / Lapsed |