US3974199A
Expired / Lapsed
US
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Process for production of cyclopropylcyanide
Assignee: Dow Chemical Co
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Filing: 1975-06-16
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Granted: 1976-08-10
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Expires: 1995-06-16
Abstract
Abstract Cyclopropylcyanide is prepared by an improved process comprising reacting by contacting a γ-halo-butyronitrile or mixture thereof, with an alkali metal hydroxide in the presence of a catalytic amount of an onium salt. For example, the reaction of 4-chlorobutyronitrile with sodium hydroxide in the presence of benzyltriethylammonium chloride produces cyclopropylcyanide in high yield.
Inventors
- 👤 James H. Plonka
- 👤 R. Garth Pews
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 23:03
CPC Classifications
C; C07; C07C; C07C255/00; C07C255/45
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
130 words
A process for the preparation of cyclopropylcyanide comprising reacting by contacting a γ--halobutyronitrile selected from the group consisting of 4-chlorobutyronitrile, 4-bromobutyronitrile, 4-iodobutyronitrile, and combinations thereof, with an alkali metal hydroxide in the presence of at least a trace amount of water and a catalytic amount of an onium salt of the formula ##EQU1## wherein: Q is a quaternized nitrogen or phosphorus atom, A - is a neutralizing anion, and R 1 -R 4 are hydrocarbyl groups of from 1 to about 16 carbon atoms each with a combined minimum total of about 10 carbon atoms, at an alkali metal hydroxide to γ-halobutyronitrile mole ratio of between about 1 to 1 and 1.5 to 1 and at a temperature at which the γ-halobutyronitrile, alkali metal hydroxide and onium salt are liquid.
Claim 2
Dependent Claim
130 words
A process for the preparation of cyclopropylcyanide comprising reacting by contacting a γ--halobutyronitrile selected from the group consisting of 4-chlorobutyronitrile, 4-bromobutyronitrile, 4-iodobutyronitrile, and combinations thereof, with an alkali metal hydroxide in the presence of at least a trace amount of water and a catalytic amount of an onium salt of the formula ##EQU1## wherein: Q is a quaternized nitrogen or phosphorus atom, A - is a neutralizing anion, and R 1 -R 4 are hydrocarbyl groups of from 1 to about 16 carbon atoms each with a combined minimum total of about 10 carbon atoms, at an alkali metal hydroxide to γ-halobutyronitrile mole ratio of between about 1 to 1 and 1.5 to 1 and at a temperature at which the γ-halobutyronitrile, alkali metal hydroxide and onium salt are liquid.
Claim 3
Dependent Claim
10 words
The process of claim 1 wherein the γ-halobutyronitrile is 4-chlorobutyronitrile.
Claim 4
Dependent Claim
15 words
The process of claim 1 wherein the alkali metal hydroxide is sodium or potassium hydroxide.
Claim 5
Dependent Claim
13 words
The process of claim 1 wherein the onium salt catalyst is benzyltriethylammonium chloride.
Claim 6
Dependent Claim
27 words
The process of claim 1 wherein the mole ratio of alkali metal hydroxide to 65 -halobutyronitrile is between about 1.1 to 1 and about 1.3 to 1.
Claim 7
Dependent Claim
31 words
The process of claim 1 wherein the onium salt catalyst is present in an amount from about .25 to about 10 weight percent based on the total weight of the reactants.
Claim 8
Dependent Claim
31 words
The process of claim 1 wherein the onium salt catalyst is present in an amount from about 1 to about 5 weight percent based on the total weight of the reactants.
Claim 9
Dependent Claim
31 words
The process of claim 1 wherein the contacting is conducted at a temperature of between about 70°C and about 85°C, at autogenous pressure, and in the absence of an organic solvent.
Claim 10
Dependent Claim
30 words
The process of claim 7 wherein water is present in an amount between about that found in reagent grade alkali metal hydroxide and about 10 percent of the reaction mass.
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) | 1979-08-10 | 1980-02-09 | 1980-08-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-10 | 1984-02-09 | 1984-08-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-10 | 1988-02-09 | 1988-08-10 | $7700.00 | Window Closed / Lapsed |