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US3981937A Expired / Lapsed US ⏱️ 0.0 years remaining

Dehydrohalogenation of 3,4-dichloro-1-butene

Assignee: EIDP Inc
•
Filing: 1970-02-13
•
Granted: 1976-09-21
•
Expires: 1990-02-13
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Abstract

Abstract Dichlorobutene is treated with aqueous inorganic alkali in the presence of a catalytic amount of a quaternary ammonium compound catalyst to dehydrochlorinate the dichlorobutene and directly form chloroprene.

Inventors

  • 👤 John B. Campbell
  • 👤 Robert Edward Tarney

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 23:15
CPC Classifications
C; C07; C07C; C07C17/00; C07C17/25

Claims Analysis

Total Claims: 24
Claim 1
Independent Claim 232 words
In a process for directly producing 2-chloro-1,3-butadiene by reacting 3,4-dichloro-1-butene with an aqueous solution containing at least about 15% by weight of alkaline material selected from the group consisting of alkali metal hydroxides and alkaline earth metal hydroxides the improvement of obtaining very substantial increases in reaction rate with a higher percentage conversion and a reduction in the percentage of the unwanted by-product, alpha-chloroprene, by carrying out the process at a temperature of about 0°-100°C and in the presence of from about 0.01% to 10% by weight, based on the weight of 3,4-dichloro-1-butene, of an organic quaternary ammonium compound catalyst in which the nitrogen is attached to four radicals by covalent bonds wherein: a. at least one of the radicals is a (C 6 -C 20 ) alkyl or alkenyl radical or at least two of the radicals are (C 7 -C 20 ) aralkyl radicals, or b. at least one of the radicals is a (C 7 -C 20 ) aralkyl radical having bonded thereto a (C 6 -C 20 ) alkyl or alkenyl radical, or c. at least one radical is an alkyl, alkenyl, or aralkyl radical containing up to 20 carbon atoms and containing a hydroxy or ether group in a position beta to the nitrogen, and d. the remaining radicals are (C 1 -C 20 ) alkyl or alkenyl radicals, or (C 7 -C 20 ) aralkyl radicals.
Claim 2
Dependent Claim 232 words
In a process for directly producing 2-chloro-1,3-butadiene by reacting 3,4-dichloro-1-butene with an aqueous solution containing at least about 15% by weight of alkaline material selected from the group consisting of alkali metal hydroxides and alkaline earth metal hydroxides the improvement of obtaining very substantial increases in reaction rate with a higher percentage conversion and a reduction in the percentage of the unwanted by-product, alpha-chloroprene, by carrying out the process at a temperature of about 0°-100°C and in the presence of from about 0.01% to 10% by weight, based on the weight of 3,4-dichloro-1-butene, of an organic quaternary ammonium compound catalyst in which the nitrogen is attached to four radicals by covalent bonds wherein: a. at least one of the radicals is a (C 6 -C 20 ) alkyl or alkenyl radical or at least two of the radicals are (C 7 -C 20 ) aralkyl radicals, or b. at least one of the radicals is a (C 7 -C 20 ) aralkyl radical having bonded thereto a (C 6 -C 20 ) alkyl or alkenyl radical, or c. at least one radical is an alkyl, alkenyl, or aralkyl radical containing up to 20 carbon atoms and containing a hydroxy or ether group in a position beta to the nitrogen, and d. the remaining radicals are (C 1 -C 20 ) alkyl or alkenyl radicals, or (C 7 -C 20 ) aralkyl radicals.
Claim 3
Dependent Claim 21 words
The process of claim 1 in which any two of said radicals are joined to form a ring containing said nitrogen.
Claim 4
Dependent Claim 15 words
The process of claim 1 in which the alkaline material is an alkali metal hydroxide.
Claim 5
Dependent Claim 21 words
The process of claim 3 wherein the mole ratio of alkali metal hydroxide to 3,4-dichloro-1-butene ranges from about 0.5:1 to 20:1.
Claim 6
Dependent Claim 13 words
The process of claim 4 wherein the alkali metal hydroxide is sodium hydroxide.
Claim 7
Dependent Claim 77 words
The process of claim 3 wherein the quaternary ammonium compound has the general formula R 1 R 2 R 3 R 4 NCl wherein R 1 , R 2 and R 3 are alkyl, alkenyl, or aralkyl radicals of up to about 20 carbon atoms and R 4 is an alkyl or alkenyl radical having from about 6 to 20 carbon atoms or a benzyl or a (C 6 -C 20 ) alkyl- or alkenyl-substituted benzyl radical.
Claim 8
Dependent Claim 14 words
The process of claim 6 wherein the quaternary ammonium compound is trioctylmethyl ammonium chloride.
Claim 9
Dependent Claim 28 words
The process of claim 6 wherein R 1 and R 2 are methyl, R 3 is C 12 to C 16 alkyl radicals and R 4 is benzyl.
Claim 10
Dependent Claim 32 words
The process of claim 6 wherein at least one of R 1 , R 2 and R 3 contains a hydroxy or ether group in a position beta to the nitrogen atom.
Claim 11
Dependent Claim 78 words
The process of claim 3 wherein the quaternary ammonium compound has the general formula ##EQU7## wherein R 1 is a (C 6 -C 20 ) alkyl or alkenyl radical, R 2 is a (C 1 -C 20 ) alkyl or alkenyl or a benzyl or (C 1 -C 20 ) alkyl-substituted benzyl radical, R 3 is H or methyl, R 4 is H or methyl, and the sum of x + y ranges from about 2 to 15.
Claim 12
Dependent Claim 18 words
The process of claim 3 wherein the quaternary ammonium compound has the formula (C.sub.12 -C.sub.18 alkyl)(benzyl)N(CH.sub.2 CHOHCH.sub.3).sub.2 Cl.
Claim 13
Dependent Claim 19 words
The process of claim 3 wherein the quaternary ammonium compound has the formula (C.sub.12 -C.sub.18 alkyl)(benzyl)N(CH.sub.2 CH.sub.2 OH).sub.2 Cl.
Claim 14
Dependent Claim 19 words
The process of claim 3 wherein the quaternary ammonium compound has the formula (C.sub.12 -C.sub.18 alkylbenzyl)N(CH.sub.2 CH.sub.2 OH).sub.3 Cl.
Claim 15
Dependent Claim 186 words
In a process for directly producing 2-chloro-1,3-butadiene with an aqueous solution containing at least about 5% by weight of alkaline material selected from the group consisting of alkali metal hydroxides and alkaline earth metal hydroxides, the improvement of obtaining very substantial increases in reaction rate with a higher percentage conversion and a reduction in the percentage of the unwanted by-product, alpha -chloroprene, by carrying out the process at a temperature of about 0°-100°C and in the presence of from about 0.01% to 10% by weight, based on the weight of 3,4-dichloro-1-butene, of an organic quaternary ammonium compound catalyst in which the nitrogen is attached to four radicals by covalent bonds wherein: a. at least one of the radicals is a (C 6 -C 20 ) alkyl, alkenyl, or aralkyl radical, and b. at least one radical is an alkyl, alkenyl, or aralkyl radical containing up to 20 carbon atoms and containing a hydroxy or ether group in a position beta to the nitrogen, and c. the remaining radicals are (C 1 -C 20 ) alkyl or alkenyl radicals or (C 7 -C 20 ) aralkyl radicals.
Claim 16
Dependent Claim 186 words
In a process for directly producing 2-chloro-1,3-butadiene with an aqueous solution containing at least about 5% by weight of alkaline material selected from the group consisting of alkali metal hydroxides and alkaline earth metal hydroxides, the improvement of obtaining very substantial increases in reaction rate with a higher percentage conversion and a reduction in the percentage of the unwanted by-product, alpha -chloroprene, by carrying out the process at a temperature of about 0°-100°C and in the presence of from about 0.01% to 10% by weight, based on the weight of 3,4-dichloro-1-butene, of an organic quaternary ammonium compound catalyst in which the nitrogen is attached to four radicals by covalent bonds wherein: a. at least one of the radicals is a (C 6 -C 20 ) alkyl, alkenyl, or aralkyl radical, and b. at least one radical is an alkyl, alkenyl, or aralkyl radical containing up to 20 carbon atoms and containing a hydroxy or ether group in a position beta to the nitrogen, and c. the remaining radicals are (C 1 -C 20 ) alkyl or alkenyl radicals or (C 7 -C 20 ) aralkyl radicals.
Claim 17
Dependent Claim 15 words
The process of claim 14 in which the alkaline material is an alkali metal hydroxide.
Claim 18
Dependent Claim 21 words
The process of claim 15 wherein the mole ratio of alkali metal hydroxide to 3,4-dichloro-1-butene ranges from about 0.5:1 to 20:1.
Claim 19
Dependent Claim 13 words
The process of claim 16 wherein the alkali metal hydroxide is sodium hydroxide.
Claim 20
Dependent Claim 104 words
The process of claim 15 wherein the quaternary ammonium compound has the general formula R 1 R 2 R 3 R 4 NCl wherein R 1 , R 2 and R 3 are alkyl, alkenyl, or aralkyl radicals of up to about 20 carbon atoms and R 4 is an alkyl or alkenyl radical having from about 6 to 20 carbon atoms or a benzyl or (C 6 -C 20 ) alkyl- or alkenyl-substituted benzyl radical and wherein at least one of R 1 , R 2 and R 3 contains a hydroxy or ether group in a position beta to the nitrogen atom.
Claim 21
Dependent Claim 78 words
The process of claim 15 wherein the quaternary ammonium compound has the general formula ##EQU8## wherein R 1 is a (C 6 -C 20 ) alkyl or alkenyl radical, R 2 is a (C 1 -C 20 ) alkyl or alkenyl or a benzyl or (C 1 -C 20 ) alkyl-substituted benzyl radical, R 3 is H or methyl, R 4 is H or methyl, and the sum of x + y ranges from about 2 to 15.
Claim 22
Dependent Claim 18 words
The process of claim 15 wherein the quaternary ammonium compound has the formula (C.sub.12 -C.sub.18 alkyl)(benzyl)N(CH.sub.2 CHOHCH.sub.3).sub.2 Cl.
Claim 23
Dependent Claim 19 words
The process of claim 15 wherein the quaternary ammonium compound has the formula (C.sub.12 -C.sub.18 alkyl)(benzyl)N(CH.sub.2 CH.sub.2 OH).sub.2 Cl.
Claim 24
Dependent Claim 19 words
The process of claim 15 wherein the quaternary ammonium compound has the formula (C.sub.12 -C.sub.18 alkylbenzyl)N(CH.sub.2 CH.sub.2 OH).sub.3 Cl.

References Cited (Backward Citations)

US2430016A Cited
US2879311A Cited
US3024283A Cited
BE657378A Cited
GB1055064A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-09-21 1980-03-22 1980-09-21 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-09-21 1984-03-22 1984-09-21 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-09-21 1988-03-22 1988-09-21 $7700.00 Window Closed / Lapsed

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