US4012453A
Expired / Lapsed
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Process for the production of chlorofluorinated aromatic hydrocarbons
Assignee: Honeywell International Inc
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Filing: 1975-12-22
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Granted: 1977-03-15
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Expires: 1995-12-22
Abstract
Abstract Chlorofluorinated aromatic hydrocarbons may be effectively produced by an oxychlorofluorination process by reacting a gaseous mixture of a starting material selected from an aromatic hydrocarbon and an aromatic hydrohalocarbon in which the halo atoms are selected from chloro and fluoro, or mixtures thereof, an oxygen-containing gas, a chlorinating agent selected from the group consisting of HCl and Cl2 and mixtures thereof, and HF, in the presence of a Deacon catalyst supported by a stable, inert metal salt carrier.
Inventors
- 👤 Henry R. Nychka
- 👤 Morris B. Berenbaum
- 👤 Martin A. Robinson
- 👤 Richard E. Eibeck
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 03:53
CPC Classifications
C; C07; C07C; C07C17/00; C07C17/093; C07C17/15; C07C17/152; C07C17/156
Claims Analysis
Total Claims: 57
Claim 1
Independent Claim
140 words
The process for the production of chlorofluorinated aromatic hydrocarbons by the oxychlorofluorination of aromatic hydrocarbons which comprises reacting a gaseous mixture of a starting material selected from an aromatic hydrocarbon and an aromatic hydrohalocarbon in which the halo atoms are selected from chloro and fluoro, or mixtures thereof, at least 0.10 mole oxygen in an oxygen-containing gas, at least 0.25 mole HCl or equivalent of Cl 2 for each C--H bond and C=C bond desired to be reacted in the starting material, and HF, in the presence of a Deacon catalyst supported by a stable, inert metal salt carrier, with the weight percentage of cation in the Deacon catalyst ranging from about 0.6-20 based on the total cation content of the Deacon catalyst and metal salt carrier, at elevated temperatures and with a contact time of from about 0.1-20 seconds.
Claim 2
Dependent Claim
140 words
The process for the production of chlorofluorinated aromatic hydrocarbons by the oxychlorofluorination of aromatic hydrocarbons which comprises reacting a gaseous mixture of a starting material selected from an aromatic hydrocarbon and an aromatic hydrohalocarbon in which the halo atoms are selected from chloro and fluoro, or mixtures thereof, at least 0.10 mole oxygen in an oxygen-containing gas, at least 0.25 mole HCl or equivalent of Cl 2 for each C--H bond and C=C bond desired to be reacted in the starting material, and HF, in the presence of a Deacon catalyst supported by a stable, inert metal salt carrier, with the weight percentage of cation in the Deacon catalyst ranging from about 0.6-20 based on the total cation content of the Deacon catalyst and metal salt carrier, at elevated temperatures and with a contact time of from about 0.1-20 seconds.
Claim 3
Dependent Claim
15 words
The process according to claim 1 in which the starting material is an aromatic hydrocarbon.
Claim 4
Dependent Claim
28 words
The process according to claim 1 in which the catalyst bed is maintained as a fixed bed and in which the contact time is from about 0.1-18 seconds.
Claim 5
Dependent Claim
16 words
The process according to claim 3 in which the contact time is from about 2-5 seconds.
Claim 6
Dependent Claim
17 words
The process according to claim 1 in which the catalyst bed is maintained as a dynamic bed.
Claim 7
Dependent Claim
28 words
The process according to claim 5 in which the catalyst bed is maintained as a fluidized bed and in which the contact time is from about 3-20 seconds.
Claim 8
Dependent Claim
16 words
The process according to claim 6 in which the contact time is from about 6-12 seconds.
Claim 9
Dependent Claim
43 words
The process according to claim 1 in which at least 0.25 mole oxygen in an oxygen-containing gas and at least 0.25 mole HCl or equivalent of Cl 2 for each C--H bond and non-aromatic C=C bond present in the starting material is employed.
Claim 10
Dependent Claim
44 words
The process according to claim 1 in which at least 0.50 mole oxygen in an oxygen containing gas and at least 0.50 mole HCl or equivalent of Cl 2 for each C--H bond and non-aromatic C=C bond present in the starting material is employed.
Claim 11
Dependent Claim
15 words
The process according to claim 1 in which the Deacon catalyst is a metal halide.
Claim 12
Dependent Claim
35 words
The process according to claim 10 in which the Deacon catalyst is promoted with a metal salt in which the metal is selected from the group consisting of Li, Na, K, Rb, La and Cs.
Claim 13
Dependent Claim
15 words
The process according to claim 1 in which the Deacon catalyst is a copper halide.
Claim 14
Dependent Claim
15 words
The process according to claim 1 in which the Deacon catalyst is CuCl 2 .
Claim 15
Dependent Claim
42 words
The process according to claim 1 in which the carrier is a metal salt in which the metal is selected from the group consisting of Al, Mg, Ca, Ba, V, Th, Sr, Co, Ni, Cd, Pb, Cr and Fe, or combinations thereof.
Claim 16
Dependent Claim
16 words
The process according to claim 14 in which the anion of the salt is a fluoride.
Claim 17
Dependent Claim
15 words
The process according to claim 15 in which the metal salt is AlF 3 .
Claim 18
Dependent Claim
16 words
The process according to claim 16 in which the AlF 3 is substantially in alpha form.
Claim 19
Dependent Claim
26 words
The process according to claim 2 in which at least 0.75 mole oxygen in an oxygen-containing gas per C--H bond in the starting material is employed.
Claim 20
Dependent Claim
13 words
The process according to claim 18 in which the aromatic hydrocarbon is benzene.
Claim 21
Dependent Claim
24 words
The process according to claim 18 in which the aromatic hydrocarbon is an alkyl benzene containing from 1-6 carbon atoms in the alkyl group.
Claim 22
Dependent Claim
24 words
The process according to claim 18 in which the aromatic hydrocarbon is a dialkyl benzene containing from 1-6 carbon atoms in each alkyl group.
Claim 23
Dependent Claim
16 words
The process according to claim 18 in which the aromatic hydrocarbon is a fused ring compound.
Claim 24
Dependent Claim
23 words
The process according to claim 18 in which the aromatic hydrocarbon is a diphenylalkane containing from 1-6 carbon atoms in the alkane moiety.
Claim 25
Dependent Claim
13 words
The process according to claim 18 in which the aromatic hydrocarbon is toluene.
Claim 26
Dependent Claim
13 words
The process according to claim 18 in which the aromatic hydrocarbon is benzene.
Claim 27
Dependent Claim
13 words
The process according to claim 18 in which the aromatic hydrocarbon is xylene.
Claim 28
Dependent Claim
13 words
The process according to claim 18 in which the aromatic hydrocarbon is naphthalene.
Claim 29
Dependent Claim
16 words
The process according to claim 18 in which the contact time is from about 2-12 seconds.
Claim 30
Dependent Claim
21 words
The process according to claim 18 in which the starting material containing a gaseous mixture is diluted with an inert gas.
Claim 31
Dependent Claim
24 words
The process according to claim 18 in which one or more halogenated aromatic hydrocarbons from the product mixture are recycled to the reaction mixture.
Claim 32
Dependent Claim
35 words
The process according to claim 18 in which the weight percentage of cation in the Deacon catalyst ranges from about 1-16 based on the total cation content of the Deacon catalyst and metal salt carrier.
Claim 33
Dependent Claim
17 words
The process according to claim 18 in which the catalyst bed is maintained as a dynamic bed.
Claim 34
Dependent Claim
17 words
The process according to claim 31 in which the catalyst bed is maintained as a fluidized bed.
Claim 35
Dependent Claim
16 words
The process according to claim 31 in which the elevated temperatures range from about 300°-500° C.
Claim 36
Dependent Claim
15 words
The process according to claim 31 in which the Deacon catalyst is a metal halide.
Claim 37
Dependent Claim
35 words
The process according to claim 35 in which the Deacon catalyst is promoted with a metal salt in which the metal is selected from the group consisting of Li, Na, K, Rb, La and Cs.
Claim 38
Dependent Claim
15 words
The process according to claim 31 in which the Deacon catalyst is a copper halide.
Claim 39
Dependent Claim
15 words
The process according to claim 31 in which the Deacon catalyst is CuCl 2 .
Claim 40
Dependent Claim
39 words
The process according to claim 31 in which the carrier is a metal salt in which the metal is selected from the group consisting of Al, Mg, Ca, Ba, V, Th, Sr, Co, Ni, Cd, Pb, Cr and Fe.
Claim 41
Dependent Claim
16 words
The process according to claim 39 in which the anion of the salt is a fluoride.
Claim 42
Dependent Claim
15 words
The process according to claim 40 in which the metal salt is AlF 3 .
Claim 43
Dependent Claim
13 words
The process according to claim 31 in which the aromatic hydrocarbon is benzene.
Claim 44
Dependent Claim
13 words
The process according to claim 31 in which the aromatic hydrocarbon is toluene.
Claim 45
Dependent Claim
13 words
The process according to claim 33 in which the aromatic hydrocarbon is xylene.
Claim 46
Dependent Claim
24 words
The process according to claim 31 in which one or more halogenated aromatic hydrocarbons from the product mixture are recycled to the reaction mixture.
Claim 47
Dependent Claim
18 words
The process according to claim 31 in which the reaction gas mixture is diluted with an inert gas.
Claim 48
Dependent Claim
34 words
The process according to claim 31 in which the weight percent of cation in the Deacon catalyst ranges from about 2-8 based on the total cation content of the Deacon catalyst and metal salt.
Claim 49
Dependent Claim
48 words
The process according to claim 31 in which the Deacon catalyst is a metal halide and in which the carrier is a metal salt in which the metal is selected from the group consisting of Al, Mg, Ca, Ba, Th, Sr, Co, Ni, Cd, Pb, Cr and Fe.
Claim 50
Dependent Claim
15 words
The process according to claim 48 in which the Deacon catalyst is CuCl 2 .
Claim 51
Dependent Claim
18 words
The process according to claim 48 in which the anion of the metal salt carrier is a fluoride.
Claim 52
Dependent Claim
15 words
The process according to claim 50 in which the metal salt is AlF 3 .
Claim 53
Dependent Claim
16 words
The process according to claim 49 in which the metal salt carrier is AlF 3 .
Claim 54
Dependent Claim
17 words
The process according to claim 51 in which the AlF 3 is substantially in the alpha form.
Claim 55
Dependent Claim
24 words
The process according to claim 48 in which one or more halogenated aromatic hydrocarbons from the product mixture are recycled to the reaction mixture.
Claim 56
Dependent Claim
137 words
The process for the production of chlorofluorinated aromatic hydrocarbons by the oxychlorofluorination of aromatic hydrocarbons which comprises reacting a gaseous mixture of a starting material selected from an aromatic hydrocarbon and an aromatic hydrohalocarbon in which the halo atoms are selected from chloro and fluoro, or mixtures thereof, at least 0.25 mole oxygen in an oxygen-containing gas for each C--H bond in the starting material, at least 2 mole HCl or equivalent Cl 2 per mole of starting material, and HF, in the presence of a Deacon catalyst supported by a stable, inert metal salt carrier, with the weight percentage of cation in the Deacon catalyst ranging from about 0.6-20 based on the total cation content of the Deacon catalyst and metal salt carrier, at elevated temperatures and with a contact time of from about 0.1-20 seconds.
Claim 57
Dependent Claim
137 words
The process for the production of chlorofluorinated aromatic hydrocarbons by the oxychlorofluorination of aromatic hydrocarbons which comprises reacting a gaseous mixture of a starting material selected from an aromatic hydrocarbon and an aromatic hydrohalocarbon in which the halo atoms are selected from chloro and fluoro, or mixtures thereof, at least 0.25 mole oxygen in an oxygen-containing gas for each C--H bond in the starting material, at least 2 mole HCl or equivalent Cl 2 per mole of starting material, and HF, in the presence of a Deacon catalyst supported by a stable, inert metal salt carrier, with the weight percentage of cation in the Deacon catalyst ranging from about 0.6-20 based on the total cation content of the Deacon catalyst and metal salt carrier, at elevated temperatures and with a contact time of from about 0.1-20 seconds.
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) | 1980-03-14 | 1980-09-13 | 1981-03-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-03-14 | 1984-09-13 | 1985-03-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-03-14 | 1988-09-13 | 1989-03-15 | $7700.00 | Window Closed / Lapsed |