US4079090A
Expired / Lapsed
US
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Preparation of trichloromethyl-trifluoro methyl-benzenes
Assignee: Bayer AG
•
Filing: 1976-10-12
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Granted: 1978-03-14
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Expires: 1996-10-12
Abstract
Abstract A process for preparing a xylene which is fluorinated and chlorinated in the side chain, having the formula ##STR1## wherein X represents hydrogen or fluorine and Y represents hydrogen or chlorine and R 1 and R 2 are identical or different and represent hydrogen, halogen, a trifluoromethyl or trichloromethyl group or an aliphatic or aromatic radical and R 1 and R 2 can be bonded via hydrocarbon members to form an aromatic ring, By contacting a compound of the formula ##STR2## wherein X, R 1 and R 2 have the above-mentioned meanings, WITH A COMPOUND OF THE FORMULA ##STR3## wherein X, R 1 and R 2 have the above-mentioned meanings, in the presence of a halogen transfer catalyst at elevated temperature.
Inventors
- 👤 Gerhard Buttner
- 👤 Erich Klauke
- 👤 Herbert Schwarz
- 👤 Fritz Doring
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 03:35
CPC Classifications
C; C07; C07C; C07C17/00; C07C17/093; C07C17/20; C07C17/202
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
123 words
A process for preparing a xylene which is fluorinated and chlorinated in the side chain, of the formula ##STR13## wherein X represents hydrogen or fluorine and Y represents hydrogen or chlorine and R 1 and R 2 are identical or different and represent hydrogen, halogen, a trifluoromethyl or trichloromethyl group or an aliphatic or aromatic radical and R 1 and R 2 can be bonded via hydrocarbon members to form an aromatic ring, which comprises contacting a compound of the formula ##STR14## wherein X, R 1 and R 2 have the above-mentioned meanings, with a compound of the formula ##STR15## wherein Y, R 1 and R 2 have the above-mentioned meanings, in the presence of a halogen transfer catalyst at an elevated temperature.
Claim 2
Dependent Claim
123 words
A process for preparing a xylene which is fluorinated and chlorinated in the side chain, of the formula ##STR13## wherein X represents hydrogen or fluorine and Y represents hydrogen or chlorine and R 1 and R 2 are identical or different and represent hydrogen, halogen, a trifluoromethyl or trichloromethyl group or an aliphatic or aromatic radical and R 1 and R 2 can be bonded via hydrocarbon members to form an aromatic ring, which comprises contacting a compound of the formula ##STR14## wherein X, R 1 and R 2 have the above-mentioned meanings, with a compound of the formula ##STR15## wherein Y, R 1 and R 2 have the above-mentioned meanings, in the presence of a halogen transfer catalyst at an elevated temperature.
Claim 3
Dependent Claim
21 words
A process according to claim 1 wherein said elevated temperature includes a temperature in the range of 10° to 180° C.
Claim 4
Dependent Claim
18 words
A process according to claim 2 wherein the temperature is in the range of 50° to 150° C.
Claim 5
Dependent Claim
47 words
A process according to claim 3 wherein the hydrogen transfer catalyst is selected from the group consisting of a halide of antimony, a halide of aluminum, a halide of copper, a halide of iron, a halide of titanium, a halide of tin and a halide of chromium.
Claim 6
Dependent Claim
16 words
A process according to claim 4 carried out at a pressure of 0.5 to 200 bars.
Claim 7
Dependent Claim
18 words
A process according to claim 5 wherein the process is carried out in the presence of a promoter.
Claim 8
Dependent Claim
20 words
A process according to claim 6 wherein the promoter is a compound which forms a complex anion with the catalyst.
Claim 9
Dependent Claim
17 words
A process according to claim 7 wherein the promoter is a metal chloride or a hydrogen chloride.
Claim 10
Dependent Claim
17 words
A process according to claim 8 wherein the promoter is an alkali metal chloride or hydrogen chloride.
Claim 11
Dependent Claim
29 words
A process according to claim 9 wherein the promoter is selected from the group consisting of sodium chloride, potassium chloride, lithium chloride, potassium fluoride, sodium fluoride and hydrogen fluoride.
Claim 12
Dependent Claim
12 words
A process according to claim 6 wherein the promoter is hydrogen chloride.
Claim 13
Dependent Claim
22 words
A process according to claim 6 wherein the promoter is a compound which activates the catalyst by the formation of a complex.
Claim 14
Dependent Claim
38 words
A process according to claim 5 wherein the molar ratio of the compound of the formula ##STR16## to the compound of the formula ##STR17## is in the range of 0.3 up to 0.7 to 0.7 down to 0.3.
Claim 15
Dependent Claim
25 words
A process according to claim 13 wherein said compounds are employed in a molar ratio of 0.4 up to 0.6 to 0.6 down to 0.4.
Claim 16
Dependent Claim
43 words
A process according to claim 13 wherein the compound having the formula ##STR18## is selected from the group consisting of 1,3-bis-(trifluoromethyl)-benzene, 2-chloro-1,3-bis-(trifluoromethyl)-benzene, 4-chloro-1,3-bis-(trifluoromethyl)-benzene, 5-chloro-1,3-(trifluoromethyl)-benzene, 4,5-dichloro-1,3-bis-(trifluoromethyl)-benzene, 2,4,5-trichloro-1,3-bis-(trifluoromethyl)-benzene, 2-bromo-1,3-bis-(trifluoromethyl)-benzene, 4-bromo-1,3-bis-(trifluoromethyl)-benzene, 4-iodo-1,3-bis-(trifluoromethyl)-benzene, 4-fluoro-1,3-bis-(trifluoromethyl)-benzene, 1,4-bis-(trifluoromethyl)-benzene, 2-chloro-1,4-bis-(trifluoromethyl)-benzene, pg,24 2-bromo-1,4-bis-(trifluoromethyl)-benzene, 2-iodo-1,4-bis-(trifluoromethyl)-benzene, 2,5-dichloro-1,4-bis-(trifluoromethyl)-benzene, 2,5-dibromo-1,4-bis-(trifluoromethyl)-benzene, 2,3,6-tetrachloro-1,4-bis-(trifluoromethyl)-benzene, 1,3,5-tris-(trifluoromethyl)-benzene, 2-fluoro-1,3,5-tris-(trifluoromethyl)-benzene, 2-bromo-1,3,5-tris-(trifluoromethyl)-benzene and 3,4,6-trichloro-1,3,5-tris-(trifluoromethyl)-benzene.
Claim 17
Dependent Claim
37 words
A process according to claim 13 wherein the compound of the formula ##STR19## is selected from the group consisting of 1,3-bis-(trichloromethyl)-benzene, 2-chloro-1,3-bis(trichloromethyl)-benzene, 4-chloro-1,3-bis-(trichloromethyl)-benzene, 5-chloro-1,3-bis-(trichloromethyl)-benzene, 4,5-dichloro-1,3-bis-(trichloromethyl)-benzene, 2,4,5-(trichloro-1,3-bis-(trichloromethyl)-benzene, 2-bromo-1,3-bis-(trichloromethyl)-benzene, 4-bromo-1,3-bis-(trichloromethyl)-benzene, 4-fluoro-1,3-bis-(trichloromethyl)-benzene, 1,4-bis-(trichloromethyl)-benzene, 2-chloro-1,4-bis-(trichloromethyl)-benzene, 2-bromo-1,4-bis-(trichloromethyl)-benzene, 2,5-dichloro-1,4-bis-(trichloromethyl)-benzene, 2,5-dibromo-1,4-bis-(trichloromethyl)-benzene, 2,3,5,6-tetrachloro-1,4-bis-(trichloromethyl)-benzene and 1,4-bis-(dichloromethyl)-benzene.
Claim 18
Dependent Claim
20 words
A process according to claim 13 wherein a trifluoromethyl benzal fluoride is reacted with the compound of the formula ##STR20##
Claim 19
Dependent Claim
20 words
A process according to claim 13 wherein a trichloromethyl benzal chloride is reacted with a compound of the formula ##STR21##
Claim 20
Dependent Claim
44 words
A process according to claim 13 wherein the reaction is carried out in the presence of a hydrogen transfer catalyst and promoter selected from the group consisting of aluminum chloride/hydrogen chloride, antimony pentachloride/hydrogen chloride, titanium tetrachloride/hydrogen chloride, ferric chloride/hydrogen chloride and tin tetrachloride/hydrogen chloride.
Claim 21
Dependent Claim
15 words
A process according to claim 5 wherein the pressure is between 1 and 80 bars.
Claim 22
Dependent Claim
29 words
A process according to claim 4 wherein said hydrogen transfer catalyst is selected from the group consisting of ferric chloride, titanium tetrachloride, aluminum chloride and an antimony V halide.
Claim 23
Dependent Claim
29 words
A process according to claim 21 wherein the hydrogen transfer catalyst is an antimony V halide selected from the group consisting of antimony pentachloride, antimony pentafluoride, antimony V chloride
Claim 24
Dependent Claim
165 words
A process for preparing a xylene which is fluorinated and chlorinated in the side chain, of the formula ##STR22## wherein X represents hydrogen or fluorine and Y represents hydrogen or chlorine and R 1 and R 2 are identical or different and represent hydrogen, halogen, a trifluoromethyl or trichloromethyl group or an aliphatic or aromatic radical and R 1 and R 2 can be bonded via hydrocarbon members to form an aromatic ring, which comprises contacting a compound of the formula ##STR23## wherein X, R 1 and R 2 have the above-mentioned meanings, with a compound of the formula ##STR24## wherein Y, R 1 and R 2 have the above-mentioned meanings, in the presence of a halogen transfer catalyst selected from the group consisting of a halide of antimony, a halide of aluminum, a halide of copper, a halide of iron, a halide of titanium, a halide of tin and a halide of chromium at a temperature in the range of 10° to 180° C.
Claim 25
Dependent Claim
165 words
A process for preparing a xylene which is fluorinated and chlorinated in the side chain, of the formula ##STR22## wherein X represents hydrogen or fluorine and Y represents hydrogen or chlorine and R 1 and R 2 are identical or different and represent hydrogen, halogen, a trifluoromethyl or trichloromethyl group or an aliphatic or aromatic radical and R 1 and R 2 can be bonded via hydrocarbon members to form an aromatic ring, which comprises contacting a compound of the formula ##STR23## wherein X, R 1 and R 2 have the above-mentioned meanings, with a compound of the formula ##STR24## wherein Y, R 1 and R 2 have the above-mentioned meanings, in the presence of a halogen transfer catalyst selected from the group consisting of a halide of antimony, a halide of aluminum, a halide of copper, a halide of iron, a halide of titanium, a halide of tin and a halide of chromium at a temperature in the range of 10° to 180° C.
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) | 1981-03-13 | 1981-09-12 | 1982-03-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-03-13 | 1985-09-12 | 1986-03-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-03-13 | 1989-09-12 | 1990-03-14 | $7700.00 | Window Closed / Lapsed |