US4766258A
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Process for producing hydrocarbon fluoride
Assignee: Asahi Kasei Corp
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Filing: 1986-01-09
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Granted: 1988-08-23
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Expires: 2006-01-09
Abstract
Abstract A process for producing a hydrocarbon fluoride at a high selectivity with minimum formation of by-products is disclosed, which comprises reacting a hydrogen-containing hydrocarbon halide with anhydrous hydrogen fluoride in a liquid phase in the presence of a reaction product of (i) at least one of (a) an oxygen-containing compound selected from the group consisting of H 2 O, H 2 O 2 and an oxygen-containing organic compound, and (b) a nitrogen-containing compound selected from the group consisting of NH 3 and a nitrogen-containing organic compound, (ii) a tin compound selected from the group consisting of a stannic halide, a stannic oxyhalide and an organotin compound, and (iii) anhydrous hydrogen fluoride.
Inventors
- 👤 Takahiro Komatsu
- 👤 Tohru Ide
- 👤 Hirohumi Akiyama
- 👤 Takao Kitamura
- 👤 Shinichi Yamamoto
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 06:35
CPC Classifications
C; C07; C07C; C07C17/00; C07C17/093; C07C17/20; C07C17/202; C07C17/206
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
124 words
A process for producing a hydrocarbon fluoride which comprises reacting a hydrogen-containing hydrocarbon halide with anhydrous hydrogen fluoride in a liquid phase in the presence of reaction product of (i) at least one of (a) an oxygen-containing compound selected from the group consisting of H 2 O, H 2 O 2 and an oxygen-containing organic compound selected from the group consisting of alcohols, ketones, carboxylic acids, aldehydes, ethers, esters and epoxy compounds, and (b) a nitrogen-containing compound selected from the group consisting of HN 3 and a nitrogen-containing organic compound, (ii) a tin compound selected from the group consisting of a stannic halide, a stannic oxyhalide and an organotin compound, and (iii) anhydrous hydrogen fluoride, said reaction product being soluble in anhydrous hydrogen fluoride.
Claim 2
Dependent Claim
124 words
A process for producing a hydrocarbon fluoride which comprises reacting a hydrogen-containing hydrocarbon halide with anhydrous hydrogen fluoride in a liquid phase in the presence of reaction product of (i) at least one of (a) an oxygen-containing compound selected from the group consisting of H 2 O, H 2 O 2 and an oxygen-containing organic compound selected from the group consisting of alcohols, ketones, carboxylic acids, aldehydes, ethers, esters and epoxy compounds, and (b) a nitrogen-containing compound selected from the group consisting of HN 3 and a nitrogen-containing organic compound, (ii) a tin compound selected from the group consisting of a stannic halide, a stannic oxyhalide and an organotin compound, and (iii) anhydrous hydrogen fluoride, said reaction product being soluble in anhydrous hydrogen fluoride.
Claim 3
Dependent Claim
14 words
A process according to claim 1, wherein the tin compound is a stannic halide.
Claim 4
Dependent Claim
13 words
A process according to claim 1, wherein the tin compound is stannic chloride.
Claim 5
Dependent Claim
14 words
A process according to claim 1, wherein the oxygen-containing compound is H 2 O.
Claim 6
Dependent Claim
14 words
A process according to claim 1, wherein the oxygen-containing organic compound is an alcohol.
Claim 7
Dependent Claim
13 words
A process according to claim 5, wherein the alcohol is a monohydric alcohol.
Claim 8
Dependent Claim
15 words
A process according to claim 1, wherein the nitrogen-containing organic compound is pyridine or triethylamine.
Claim 9
Dependent Claim
62 words
A process according to claim 1, wherein the hydrogen-containing hydrocarbon halide is represented by formula (I) ##STR3## wherein X represents a halogen atom other than F; R 1 represents a hydrogen atom, a halogen atom, a hydrocarbon group, or a hydrocarbon halide group; and R 2 and R 3 each represents a halogen atom, a hydrocarbon group, or a hydrocarbon halide group.
Claim 10
Dependent Claim
13 words
A process according to claim 8, wherein the hydrogen-containing hydrocarbon halide is 1,1,1-trichloroethane.
Claim 11
Dependent Claim
13 words
A process according to claim 8, wherein the hydrogen-containing hydrocarbon halide is 1,1,1,2-tetrachloroethane.
Claim 12
Dependent Claim
48 words
A process according to claim 1, wherein the hydrogen-containing hydrocarbon halide is represented by formula (II) ##STR4## wherein X represents a halogen atom other than F; and R 4 and R 5 each represents a hydrogen atom, a halogen atom, a hydrocarbon group, or a hydrocarbon halide group.
Claim 13
Dependent Claim
13 words
A process according to claim 11, wherein the hydrogen-containing hydrocarbon halide is 1,1,2-trichloroethane.
Claim 14
Dependent Claim
13 words
A process according to claim 11, wherein the hydrogen-containing hydrocarbon halide is 1,2-dichloro-1-fluoroethane.
Claim 15
Dependent Claim
81 words
A process according to claim 1, wherein the hydrogen-containing hydrocarbon halide is represented by formula (III) ##STR5## wherein R 6 represents a hydrogen atom, a halogen atom, a hydrocarbon group, or a hydrocarbon halide group; and R 7 and R 8 each represents a halogen atom, a hydrocarbon group, or a hydrocarbon halide group, provided that R 7 and R 8 are not a hydrocarbon groups at the same time when R 6 is a hydrogen atom or a hydrocarbon group.
Claim 16
Dependent Claim
13 words
A process according to claim 14, wherein the hydrogen-containing hydrocarbon halide is 1,1-dichloroethylene.
Claim 17
Dependent Claim
13 words
A process according to claim 14, wherein the hydrogen-containing hydrocarbon halide is trichloroethylene.
Claim 18
Dependent Claim
61 words
A process according to claim 1, wherein the hydrogen-containing hydrocarbon halide is represented by formula (IV-1) or (IV-2): ##STR6## wherein R 9 and R 10 each represents a hydrogen atom, a halogen atom, a hydrocarbon group, or a hydrocarbon halide group, provided that R 9 and R 10 are not a hydrogen atom and/or a hydrocarbon group at the same time.
Claim 19
Dependent Claim
13 words
A process according to claim 17, wherein the hydrogen-containing hydrocarbon halide is 1,2-dichloroethylene.
Claim 20
Dependent Claim
18 words
A process according to claim 1, wherein the reaction pressure ranges from 3 to 30 kg/cm 2 G.
Claim 21
Dependent Claim
16 words
A process according to claim 1, wherein the reaction temperature ranges from 50° to 200° C.
Claim 22
Dependent Claim
23 words
A process according to claim 1, wherein the molar ratio of F to Sn in the reaction liquid ranges from 6/1 to 100/1.
Claim 23
Dependent Claim
23 words
A process according to claim 1, wherein the molar ratio of O to Sn in said reaction product ranges from 0.2/1 to 2/1.
Claim 24
Dependent Claim
51 words
A process according to claim 1, wherein the oxygen-containing compound is H 2 O or an alcohol, the tin compound is a stannic halide, the hydrogen-containing hydrocarbon halide is 1,1,2-trichloroethane, and the molar ratio of O to Sn in said reaction product is in the range of from 0.2/1 to 2/1.
Claim 25
Dependent Claim
53 words
A process according to claim 1, wherein the oxygen-containing compound is H 2 O or an alcohol, the tin compound is a stannic halide, the hydrogen-containing hydrocarbon halide is 1,1-dichloroethylene or 1,1,1-trichloroethane, and the molar ratio of O to Sn in said reaction product is in the range of from 0.2/1 to 2/1.
Claim 26
Dependent Claim
27 words
A process according to claim 1, wherein the hydrogen-containing hydrocarbon halide is a hydrogen-containing hydrocarbon chloride and by-produced hydrogen chloride is continuously withdrawn from the reaction system.
Claim 27
Dependent Claim
22 words
A process according to claim 1, wherein the hydrocarbon fluoride produced is withdrawn from the reaction system in the form of vapor.
Claim 28
Dependent Claim
69 words
A process according to claim 1, wherein the reaction solution obtained by reacting the hydrogen-containing hydrocarbon halide with anhydrous hydrogen fluoride in a liquid phase in the presence of said reaction product is separated into an organic phase predominantly composed of a hydrocarbon halide and a hydrogen fluoride phase predominantly composed of said reaction product and anhydrous hydrogen fluoride, and the hydrocarbon fluoride is obtained from the organic phase.
Claim 29
Dependent Claim
17 words
A process according to claim 27, wherein the hydrogen fluoride phase is recycled to the reaction system.
Claim 30
Dependent Claim
18 words
A process according to claim 1, wherein the hydrogen-containing hydrocarbon halide is continuously reacted with anhydrous hydrogen fluoride.
Claim 31
Dependent Claim
51 words
A process according to claim 1, wherein the oxygen-containing organic compound is selected from the group consisting of methyl alcohol, ethyl alcohol, propyl alcohol, butyl alcohol, ethylene glycol, acetone, methyl ethyl ketone, formic acid, acetic acid, propionic acid, formaldehyde, butyaldehyde, methyl ether, ethyl ether, tetrahydrofuran, 1,4-dioxane and ethylene glycol monoethyl ether.
Claim 32
Dependent Claim
25 words
A process according to claim 1, wherein the nitrogen-containing compound is selected from the group consisting of pyridine, triethylamine, sec-butylamine, hexamethylenediamine, aniline, toluidine and triethanolamine.
Claim 33
Dependent Claim
97 words
A process according to claim 1, wherein the hydrogen-containing hydrocarbon halide is represented by formula (I) ##STR7## wherein X represents a halogen atom other than F; R 1 represents a hydrogen atom, a halogen atom, a hydrocarbon group, or a hydrocarbon halide group; and R 2 and R 3 each represents a halogen atom, a hydrocarbon group, or a hydrocarbon halide group; or formula (II) ##STR8## wherein X represents a halogen atom other than F; and R 4 and R 5 each represents a hydrogen atom, a halogen atom, a hydrocarbon group, or a hydrocarbon halide group.
Claim 34
Dependent Claim
18 words
A process according to claim 1, wherein the tin compound is a stannic halide or an organotin compound.
Claim 35
Dependent Claim
18 words
A process according to claim 12, wherein the hydrocarbon fluorides produced by said process are 1,2-dichloro-1-fluoroethane and 2-chloro-1,1-difluoroethane.
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