Patent US3876716A successfully refreshed from Google Patents.
US3876716A
Expired / Lapsed
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Dehydrochlorination of chlorinated compounds
Assignee: EIDP Inc
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Filing: 1973-01-26
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Granted: 1975-04-08
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Expires: 1993-01-26
Abstract
Abstract The rate of dehydrochlorination of certain chlorinated aliphatic hydrocarbons by reaction with an alkali metal hydroxide in an aqueous medium is accelerated and production of unwanted byproducts is minimized by having present in the aqueous medium a catalytic amount of an amine oxide of a specified class.
Inventors
- 👤 John B Campbell
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 13:16
CPC Classifications
A; A62; A62D; A62D3/00; A62D3/30; A62D3/34; C; C07; C07C; C07C17/00; C07C17/25; A62D2101/00; A62D2101/20; A62D2101/22
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
152 words
IN A PROCESS FOR DEHYDROCHLORINATING A CHLORINATED ALIPHATIC HYDROCARBON SELECTED FROM THE GROUP CONSISTING OF 3,4-DICHLORO-1-BUTENE; 2,3,4-TRICHLORO-1-BUTENE; AND 1,2,3,4TETRACHLOROBUTANE BY REACTING SAID CHLORINATED COMPOUND WITH AN AQUEOUS SOLUTION OF AN ALKALI METAL HYDROXIDE, THE IMPROVEMENT OF CARRYING OUT THE PROCESS IN THE PRESENCE OF FROM ABOUT 0.1 TO ABOUT 10% BY WEIGHT, BASED ON THE WEIGHT OF SAID CHLORINATED COMPOUND, OF AN AMINE OXIDE WHICH IS EITHER: A. A TERTIARY AMINE OXIDE HAVING THE STRUCTURE R1R2R3NO, WHERE R1,R2 AND R3 ARE THE SAME OR DIFFERENT RADICALS SELECTED FROM (A) UNSUBSTITUTED HYDROCARBON RADICALS OF 1 TO 20 CARBON ATOMS, OR ((B) SUBSTITUTED ALIPHATIC HYDROCARBON RADICALS WHEREIN THE SUBSTITUTION CONSISTS OF HYDROXY, ALKOXY, OR CARBOXAMIDE RADICALS IN POSITIONS NO CLOSER TO THE N ATOM THAN THE BETA POSITION, THE ALKYL GROUP OF A SAID ALKOXY SUBSTITUENT RADICAL CONTAINING FROM 1 TO 20 CARBON ATOMS THE CARBOXAMIDE RADICAL BEING SELECTED FROM THE GROUP CONSISTING OF
Claim 2
Dependent Claim
152 words
IN A PROCESS FOR DEHYDROCHLORINATING A CHLORINATED ALIPHATIC HYDROCARBON SELECTED FROM THE GROUP CONSISTING OF 3,4-DICHLORO-1-BUTENE; 2,3,4-TRICHLORO-1-BUTENE; AND 1,2,3,4TETRACHLOROBUTANE BY REACTING SAID CHLORINATED COMPOUND WITH AN AQUEOUS SOLUTION OF AN ALKALI METAL HYDROXIDE, THE IMPROVEMENT OF CARRYING OUT THE PROCESS IN THE PRESENCE OF FROM ABOUT 0.1 TO ABOUT 10% BY WEIGHT, BASED ON THE WEIGHT OF SAID CHLORINATED COMPOUND, OF AN AMINE OXIDE WHICH IS EITHER: A. A TERTIARY AMINE OXIDE HAVING THE STRUCTURE R1R2R3NO, WHERE R1,R2 AND R3 ARE THE SAME OR DIFFERENT RADICALS SELECTED FROM (A) UNSUBSTITUTED HYDROCARBON RADICALS OF 1 TO 20 CARBON ATOMS, OR ((B) SUBSTITUTED ALIPHATIC HYDROCARBON RADICALS WHEREIN THE SUBSTITUTION CONSISTS OF HYDROXY, ALKOXY, OR CARBOXAMIDE RADICALS IN POSITIONS NO CLOSER TO THE N ATOM THAN THE BETA POSITION, THE ALKYL GROUP OF A SAID ALKOXY SUBSTITUENT RADICAL CONTAINING FROM 1 TO 20 CARBON ATOMS THE CARBOXAMIDE RADICAL BEING SELECTED FROM THE GROUP CONSISTING OF
Claim 3
Dependent Claim
12 words
The process of claim 1 wherein the alkali metal hydroxide is sodium
Claim 4
Dependent Claim
14 words
The process of claim 1 wherein said amine oxide is present in an amount
Claim 5
Dependent Claim
155 words
In a process for dehydrochlorinating 3,4-dichloro-1-butene by reacting said 3,4-dichloro-1-butene with an aqueous solution of an alkali metal hydroxide, the improvement of carrying out the process at a temperature within the range of from about 40.degree. to about 85.degree.C. in the presence of from about 0.1 to about 10 percent, by weight, based on the weight of said 3,4-dichloro-1-butene, of an amine oxide which is either: A. a tertiary amine oxide having the structure R.sup.1 R.sup.2 R.sup.3 NO, where R.sup.1, R.sup.2 and R.sup.3 are the same or different radicals selected from (a) unsubstituted hydrocarbon radicals of 1 to 20 carbon atoms, or (b) substituted aliphatic hydrocarbon radicals wherein the substitution consists of hydroxy, alkoxy, or carboxamide radicals in positions no closer to the N atom than the beta position; the alkyl group of said alkoxy substituent radical containing from 1 to 20 carbon atoms and the carboxamide radical being selected from the group consisting of
Claim 6
Dependent Claim
155 words
In a process for dehydrochlorinating 3,4-dichloro-1-butene by reacting said 3,4-dichloro-1-butene with an aqueous solution of an alkali metal hydroxide, the improvement of carrying out the process at a temperature within the range of from about 40.degree. to about 85.degree.C. in the presence of from about 0.1 to about 10 percent, by weight, based on the weight of said 3,4-dichloro-1-butene, of an amine oxide which is either: A. a tertiary amine oxide having the structure R.sup.1 R.sup.2 R.sup.3 NO, where R.sup.1, R.sup.2 and R.sup.3 are the same or different radicals selected from (a) unsubstituted hydrocarbon radicals of 1 to 20 carbon atoms, or (b) substituted aliphatic hydrocarbon radicals wherein the substitution consists of hydroxy, alkoxy, or carboxamide radicals in positions no closer to the N atom than the beta position; the alkyl group of said alkoxy substituent radical containing from 1 to 20 carbon atoms and the carboxamide radical being selected from the group consisting of
Claim 7
Dependent Claim
14 words
The process of claim 4 wherein said amine oxide has at least one radical
Claim 8
Dependent Claim
11 words
The process of claim 4 wherein the amine oxide is (C.sub.8
Claim 9
Dependent Claim
12 words
The process of claim 4 wherein the amine oxide is stearyl dimethylamine
Claim 10
Dependent Claim
13 words
The process of claim 4 wherein the amine oxide is bis(2-hydroxyethyl) stearylamine oxide.
References Cited (Backward Citations)
US2430016A
Cited
US2999888A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-04-07 | 1978-10-07 | 1979-04-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-04-07 | 1982-10-07 | 1983-04-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-04-07 | 1986-10-07 | 1987-04-08 | $7700.00 | Window Closed / Lapsed |