US3941827A
Expired / Lapsed
US
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Preparation of halogenated nitriles
Assignee: Velsicol Chemical LLC
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Filing: 1974-02-04
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Granted: 1976-03-02
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Expires: 1994-02-04
Abstract
Abstract A process is disclosed for preparing halogenated hydrocarbyl nitriles comprising reacting a metal or ammonium cyanide with a dihalogenated aliphatic or alicyclic hydrocarbon of the formula X--R--CH 2 --X 1 where X and X 1 are chloro, bromo or iodo and R is a divalent aliphatic, alicyclic or aralkyl hydrocarbon group, In an aqueous medium in the presence of a phase transfer catalyst.
Inventors
- 👤 Robert Phillip Johnson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 11:05
CPC Classifications
C; C07; C07C; C07C255/00; C07C255/01; C07C255/10; C07C253/00; C07C253/30; C07C253/14; C07C255/19
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
64 words
A process for preparing 4-halobutyronitrile wherein said nitrile is 4-chlorobutyronitrile, 4-bromobutyronitrile or mixtures thereof comprising reacting a water ionizable metal or ammonium cyanide with 1-chloro-3-bromopropane, in a molar ratio of 1-chloro-3-bromopropane to cyanide of about 1:1 to about 2:1, the reaction medium being water, and in the presence of a phase transfer catalyst, the reaction temperature being maintained at about 50° to about 100°C.
Claim 2
Dependent Claim
64 words
A process for preparing 4-halobutyronitrile wherein said nitrile is 4-chlorobutyronitrile, 4-bromobutyronitrile or mixtures thereof comprising reacting a water ionizable metal or ammonium cyanide with 1-chloro-3-bromopropane, in a molar ratio of 1-chloro-3-bromopropane to cyanide of about 1:1 to about 2:1, the reaction medium being water, and in the presence of a phase transfer catalyst, the reaction temperature being maintained at about 50° to about 100°C.
Claim 3
Dependent Claim
17 words
A process according to claim 1 wherein said metal or ammonium cyanide is an alkali metal cyanide.
Claim 4
Dependent Claim
14 words
A process according to claim 2 wherein said alkali metal cyanide is sodium cyanide.
Claim 5
Dependent Claim
18 words
A process according to claim 1 wherein said phase transfer catalyst is a quaternary ammonium or phosphonium compound.
Claim 6
Dependent Claim
16 words
A process according to claim 1 wherein said phase transfer catalyst is a quaternary ammonium halide.
Claim 7
Dependent Claim
15 words
A process according to claim 5 wherein said quaternary ammonium halide is cetyltrimethyl ammonium bromide.
Claim 8
Dependent Claim
18 words
A process according to claim 1 wherein said reaction temperature is from about 65° to about 85° C.
Claim 9
Dependent Claim
18 words
A process according to claim 7 wherein said reaction temperature is from about 70° to about 75° C.
Claim 10
Dependent Claim
17 words
A process according to claim 8 wherein said molar ratio is from about 1.5:1 to about 2:1.
Claim 11
Dependent Claim
12 words
A process according to claim 9 wherein said molar ratio is 1.5:1.
Claim 12
Dependent Claim
12 words
A process according to claim 9 wherein said molar ratio is 2:1.
Claim 13
Dependent Claim
27 words
A process according to claim 1 wherein the aqueous layer of the reaction mixture is washed with a metal chloride solution prior to removal of said 4-halobutyronitrile.
Claim 14
Dependent Claim
69 words
A process for preparing 4-halobutyronitrile wherein said nitrile is selected from the group consisting of 4-chlorobutyronitrile, 4-bromobutyronitrile or mixtures thereof comprising reacting an alkali metal cyanide with 1-chloro-3-bromopropane in a molar ratio of about 1:5 to 2:1, the reaction medium being water, in the presence of a quaternary ammonium halide phase transfer catalyst having at least 10 carbon atoms, the reaction temperature being maintained at about 50° to 100°C.
Claim 15
Dependent Claim
69 words
A process for preparing 4-halobutyronitrile wherein said nitrile is selected from the group consisting of 4-chlorobutyronitrile, 4-bromobutyronitrile or mixtures thereof comprising reacting an alkali metal cyanide with 1-chloro-3-bromopropane in a molar ratio of about 1:5 to 2:1, the reaction medium being water, in the presence of a quaternary ammonium halide phase transfer catalyst having at least 10 carbon atoms, the reaction temperature being maintained at about 50° to 100°C.
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) | 1979-03-02 | 1979-09-01 | 1980-03-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-03-02 | 1983-09-01 | 1984-03-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-03-02 | 1987-09-01 | 1988-03-02 | $7700.00 | Window Closed / Lapsed |