JPS6345231A - ３，４−ジクロロ−６−トリフルオロメチルトルエンの製造法 - Google Patents
３，４−ジクロロ−６−トリフルオロメチルトルエンの製造法Info
- Publication number
- JPS6345231A JPS6345231A JP61188575A JP18857586A JPS6345231A JP S6345231 A JPS6345231 A JP S6345231A JP 61188575 A JP61188575 A JP 61188575A JP 18857586 A JP18857586 A JP 18857586A JP S6345231 A JPS6345231 A JP S6345231A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- dichloro
- ccl4
- reaction product
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- OARYHYOOIUIKFZ-UHFFFAOYSA-N 1,2-dichloro-4-methyl-5-(trifluoromethyl)benzene Chemical compound CC1=CC(Cl)=C(Cl)C=C1C(F)(F)F OARYHYOOIUIKFZ-UHFFFAOYSA-N 0.000 title claims 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims abstract description 24
- WYUIWKFIFOJVKW-UHFFFAOYSA-N 1,2-dichloro-4-methylbenzene Chemical compound CC1=CC=C(Cl)C(Cl)=C1 WYUIWKFIFOJVKW-UHFFFAOYSA-N 0.000 claims abstract description 10
- -1 aluminum halide Chemical class 0.000 claims description 11
- 229910052782 aluminium Inorganic materials 0.000 claims description 8
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 5
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 5
- CBXDCGQZMAUIHD-UHFFFAOYSA-N 1-methyl-2-(trichloromethyl)benzene Chemical compound CC1=CC=CC=C1C(Cl)(Cl)Cl CBXDCGQZMAUIHD-UHFFFAOYSA-N 0.000 claims 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract description 10
- 239000007795 chemical reaction product Substances 0.000 abstract description 7
- 239000007864 aqueous solution Substances 0.000 abstract description 3
- 238000009835 boiling Methods 0.000 abstract description 3
- JZWZPWDFZGTMIF-UHFFFAOYSA-N 1,2-dichloro-4-methyl-5-(trichloromethyl)benzene Chemical compound CC1=CC(Cl)=C(Cl)C=C1C(Cl)(Cl)Cl JZWZPWDFZGTMIF-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 4
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 239000003905 agrochemical Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 238000005292 vacuum distillation Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DLESTTCLFWLCBX-UHFFFAOYSA-N 1,2-dichloro-5-methyl-3-(trifluoromethyl)benzene Chemical compound CC1=CC(Cl)=C(Cl)C(C(F)(F)F)=C1 DLESTTCLFWLCBX-UHFFFAOYSA-N 0.000 description 1
- DVFVNJHIVAPTMS-UHFFFAOYSA-N 1-methyl-2-(trifluoromethyl)benzene Chemical compound CC1=CC=CC=C1C(F)(F)F DVFVNJHIVAPTMS-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61188575A JPS6345231A (ja) | 1986-08-13 | 1986-08-13 | ３，４−ジクロロ−６−トリフルオロメチルトルエンの製造法 |
| US07/084,019 US4876404A (en) | 1986-08-13 | 1987-08-11 | Preparation of dichlorotrifluoromethyltoluenes including novel isomers |
| DE19873726890 DE3726890A1 (de) | 1986-08-13 | 1987-08-12 | Verfahren zur herstellung von dichlortrifluormethyltoluolen und nach dem verfahren hergestellte neue isomere |
| FR878711502A FR2602764B1 (fr) | 1986-08-13 | 1987-08-12 | Composes dichlorotrifluoromethyltoluenes et procede de preparation de ces composes |
| GB8719063A GB2194235B (en) | 1986-08-13 | 1987-08-12 | Dichlorotrifluoromethyltoluenes and preparation thereof |
| IT8721651A IT1228929B (it) | 1986-08-13 | 1987-08-13 | Preparazione di diclorotrifluorometiltolueni, inclusi isomeri |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61188575A JPS6345231A (ja) | 1986-08-13 | 1986-08-13 | ３，４−ジクロロ−６−トリフルオロメチルトルエンの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6345231A true JPS6345231A (ja) | 1988-02-26 |
| JPH0474340B2 JPH0474340B2 (enrdf_load_stackoverflow) | 1992-11-26 |
Family
ID=16226080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61188575A Granted JPS6345231A (ja) | 1986-08-13 | 1986-08-13 | ３，４−ジクロロ−６−トリフルオロメチルトルエンの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6345231A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03161450A (ja) * | 1989-11-17 | 1991-07-11 | Asahi Glass Co Ltd | 新規フルオロベンゾトリクロリド化合物およびフルオロ安息香酸類の製造方法 |
| KR20180074695A (ko) * | 2015-10-26 | 2018-07-03 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 2-알킬-4-트리플루오로메틸-3-알킬설포닐벤조산의 합성 방법 |
-
1986
- 1986-08-13 JP JP61188575A patent/JPS6345231A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03161450A (ja) * | 1989-11-17 | 1991-07-11 | Asahi Glass Co Ltd | 新規フルオロベンゾトリクロリド化合物およびフルオロ安息香酸類の製造方法 |
| KR20180074695A (ko) * | 2015-10-26 | 2018-07-03 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 2-알킬-4-트리플루오로메틸-3-알킬설포닐벤조산의 합성 방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0474340B2 (enrdf_load_stackoverflow) | 1992-11-26 |
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