US3725458A
Expired / Lapsed
US
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Process for preparing cyano-compounds
Assignee: ConocoPhillips Co
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Filing: 1971-11-17
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Granted: 1973-04-03
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Expires: 1991-11-17
Abstract
Abstract A process for the preparation of terminally substituted cyanocompounds from 1-alkenes. The process involves the preparation of a 1-bromoalkane from the reaction of the 1-alkene and HBr in the presence of an initiator followed by a catalyzed halogen exchange reaction with HC1 wherein a 1-chloroalkane is formed and HBr is regenerated. The 1-chloroalkane is then reacted with a cyanide containing compound in the presence of an organic quaternary salt catalyst to produce the desired terminally substituted cyanocompound, a 1-cyanoalkane.
Inventors
- 👤 C Starks
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 02:46
CPC Classifications
C; C07; C07C; C07C253/00; C07C253/14; C07C17/00; C07C17/07; C07C17/08; C07C17/093; C07C17/20; C07C17/202; C07C17/206
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
49 words
The process according to claim 1 wherein said 1-chloroalkane and said aqueous solution of an alkali or alkaline earth metal cyanide salt are present in a molar ratio of about 1:1 and said reaction is carried out at a temperature within the range of about 100* to 150* C.
Claim 2
Dependent Claim
79 words
The process of claim 2 which includes the following purification steps: a. washing the 1-bromoalkane sequentially with water, an aqueous sodium carbonate solution, and water to purify the 1-bromoalkane prior to reacting said with HCl; and washing the 1-chloroalkane with an aqueous solution containing 5 weight percent sodium hydroxide and drying the washed product over sodium sulfate prior to contacting same with said aqueous solution of an alkali or alkaline earth metal cyanide salt to produce the desired 1-cyanoalkane.
Claim 3
Dependent Claim
25 words
The process according to claim 3 wherein said M'' of said organic quaternary salt catalyst is selected from the group consisting of nitrogen and phosphorous.
Claim 4
Dependent Claim
14 words
The process according to claim 4 wherein said cyanide containing salt is sodium cyanide.
Claim 5
Dependent Claim
249 words
A process for preparing a 1-cyanoalkane from a 1-alkene having four to 18 carbon atoms per molecule which comprises the sequential steps of: a. reacting the 1-alkene in the presence of an effective amount of a free radical initiator selected from the group consisting of benzoyl peroxide, air, ultraviolet light, di-t-butyl peroxide, and t-butyl hydroperoxide at a temperature of about 25* to 60* C to produce a 1-bromoalkane; b. reacting said 1-bromoalkane with 1 to 100 moles of HC1 per mole of 1-bromoalkane in the presence of an amount of tributyloctydecylphosphonium bromide sufficient to effect halogen exchange at a temperature of 100* C to 250* C and a pressure of from about atmospheric to about 2,000 psig in a reaction environment characterized by the substantial complete absence of any added solvent to form a 1-chloroalkane having four to 14 carbon atoms per molecule; c. reacting said 1-chloroalkane with sodium cyanide in aqueous medium in a molar ratio of about 1:0.5 to 1:4 at a temperature in the range of about 50* to 200* C in the presence of 0.01 to 10 weight percent, based on the weight of the 1-chloroalkane, of an organic quaternary salt catalyst selected from the group consisting of tridecylammonium chloride, tributylhexadecylphosphonium chloride, and an oleophilic ion exchange resin prepared by treating trioctylamine with chloromethylated cross-linked polystyrene resin to replace the chlorine constituent of the 1-chloroalkane with the cyanide constituent of the sodium cyanide; and d. recovering from the reaction mixture of step (c) the 1-cyanoalkane.
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) | 1976-04-02 | 1976-10-02 | 1977-04-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1980-04-02 | 1980-10-02 | 1981-04-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1984-04-02 | 1984-10-02 | 1985-04-03 | $7700.00 | Window Closed / Lapsed |