FR2478074A1 - Procede de preparation de trifluoromethylbenzenes a partir des trichloro- ou tribromo-methylbenzenes correspondants - Google Patents
Procede de preparation de trifluoromethylbenzenes a partir des trichloro- ou tribromo-methylbenzenes correspondants Download PDFInfo
- Publication number
- FR2478074A1 FR2478074A1 FR8005877A FR8005877A FR2478074A1 FR 2478074 A1 FR2478074 A1 FR 2478074A1 FR 8005877 A FR8005877 A FR 8005877A FR 8005877 A FR8005877 A FR 8005877A FR 2478074 A1 FR2478074 A1 FR 2478074A1
- Authority
- FR
- France
- Prior art keywords
- tribromo
- trichloro
- hydrofluoric acid
- liquid
- methylbenzene
- 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
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 150000005226 trifluoromethylbenzenes Chemical class 0.000 title abstract description 7
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 48
- 239000007788 liquid Substances 0.000 claims abstract description 34
- 238000010924 continuous production Methods 0.000 claims abstract description 3
- 230000001174 ascending effect Effects 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 12
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 claims description 10
- MVDRXYIEGOGRAI-UHFFFAOYSA-N tribromomethylbenzene Chemical compound BrC(Br)(Br)C1=CC=CC=C1 MVDRXYIEGOGRAI-UHFFFAOYSA-N 0.000 claims description 8
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims description 5
- MKSTYJIDBFKGJI-UHFFFAOYSA-N 1,2,3-tribromo-4-methylbenzene Chemical class CC1=CC=C(Br)C(Br)=C1Br MKSTYJIDBFKGJI-UHFFFAOYSA-N 0.000 abstract description 4
- 239000007789 gas Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- 238000003682 fluorination reaction Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- XILPLWOGHPSJBK-UHFFFAOYSA-N 1,2-dichloro-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Cl)C(Cl)=C1 XILPLWOGHPSJBK-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 150000005172 methylbenzenes Chemical class 0.000 description 2
- QULYNCCPRWKEMF-UHFFFAOYSA-N parachlorobenzotrifluoride Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1 QULYNCCPRWKEMF-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- -1 trichloromethyl- Chemical group 0.000 description 2
- ATYLRBXENHNROH-UHFFFAOYSA-N 1,2-dichloro-4-(trichloromethyl)benzene Chemical compound ClC1=CC=C(C(Cl)(Cl)Cl)C=C1Cl ATYLRBXENHNROH-UHFFFAOYSA-N 0.000 description 1
- YTCGOUNVIAWCMG-UHFFFAOYSA-N 1-chloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(Cl)=C1 YTCGOUNVIAWCMG-UHFFFAOYSA-N 0.000 description 1
- NBJZEUQTGLSUOB-UHFFFAOYSA-N 1-chloro-4-isocyanato-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(N=C=O)=CC=C1Cl NBJZEUQTGLSUOB-UHFFFAOYSA-N 0.000 description 1
- GBOWGKOVMBDPJF-UHFFFAOYSA-N 1-fluoro-3-(trifluoromethyl)benzene Chemical compound FC1=CC=CC(C(F)(F)F)=C1 GBOWGKOVMBDPJF-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- HPMLGNIUXVXALD-UHFFFAOYSA-N benzoyl fluoride Chemical compound FC(=O)C1=CC=CC=C1 HPMLGNIUXVXALD-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000013529 heat transfer fluid Substances 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/245—Stationary reactors without moving elements inside placed in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B39/00—Halogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/62—Preparation of carboxylic acid halides by reactions not involving the carboxylic acid halide group
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
- B01J2219/00094—Jackets
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00186—Controlling or regulating processes controlling the composition of the reactive mixture
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8005877A FR2478074A1 (fr) | 1980-03-17 | 1980-03-17 | Procede de preparation de trifluoromethylbenzenes a partir des trichloro- ou tribromo-methylbenzenes correspondants |
| AT81400328T ATE3632T1 (de) | 1980-03-17 | 1981-03-04 | Verfahren zur herstellung von trifluormethylbenzolen aus den uebereinstimmenden trichlor- oder tribrommethylbenzolen. |
| EP81400328A EP0036352B1 (fr) | 1980-03-17 | 1981-03-04 | Procédé de préparation de trifluorométhylbenzènes à partir des trichloro- ou tribromo-méthylbenzènes correspondants |
| DE8181400328T DE3160378D1 (en) | 1980-03-17 | 1981-03-04 | Process for the preparation of trifluoromethyl benzenes from the corresponding trichloro or tribromo methyl benzenes |
| US06/243,205 US4462937A (en) | 1980-03-17 | 1981-03-12 | Process for the preparation of trifluoromethylbenzenes from the corresponding trichloro- or tribromo-methylbenzenes |
| IL62379A IL62379A (en) | 1980-03-17 | 1981-03-16 | Continuous countercurrent process for the preparation of trifluoromethylbenzenes |
| JP3666781A JPS572225A (en) | 1980-03-17 | 1981-03-16 | Manufacture of trifluoromethylbenzenes from corresponding trichloro- or tribromo- methylbenzenes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8005877A FR2478074A1 (fr) | 1980-03-17 | 1980-03-17 | Procede de preparation de trifluoromethylbenzenes a partir des trichloro- ou tribromo-methylbenzenes correspondants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2478074A1 true FR2478074A1 (fr) | 1981-09-18 |
| FR2478074B1 FR2478074B1 (enExample) | 1982-06-25 |
Family
ID=9239720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8005877A Granted FR2478074A1 (fr) | 1980-03-17 | 1980-03-17 | Procede de preparation de trifluoromethylbenzenes a partir des trichloro- ou tribromo-methylbenzenes correspondants |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4462937A (enExample) |
| EP (1) | EP0036352B1 (enExample) |
| JP (1) | JPS572225A (enExample) |
| AT (1) | ATE3632T1 (enExample) |
| DE (1) | DE3160378D1 (enExample) |
| FR (1) | FR2478074A1 (enExample) |
| IL (1) | IL62379A (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4582935A (en) * | 1984-12-21 | 1986-04-15 | Olin Corporation | Process for producing meta-aminobenzotrifluoride |
| JPS62149382U (enExample) * | 1986-03-14 | 1987-09-21 | ||
| JPS6316778U (enExample) * | 1986-07-18 | 1988-02-03 | ||
| US4876404A (en) * | 1986-08-13 | 1989-10-24 | Central Glass Company, Limited | Preparation of dichlorotrifluoromethyltoluenes including novel isomers |
| DE3725659A1 (de) * | 1987-08-03 | 1989-02-16 | Bayer Ag | Verfahren zur herstellung von mit fluor und gegebenenfalls zusaetzlich chlor substituierten benzotrifluoriden und neue benzotrifluoride |
| JP2606875B2 (ja) * | 1988-03-31 | 1997-05-07 | 株式会社トクヤマ | 有機化合物のフッ素化方法 |
| CA2216103A1 (en) * | 1995-03-22 | 1996-09-26 | Michael Bono | Improved nebulizer and inhalation device containing same |
| JP3638790B2 (ja) * | 1998-04-27 | 2005-04-13 | セントラル硝子株式会社 | ビストリフルオロメチルベンゼンの製造方法 |
| CN102134175B (zh) * | 2010-12-31 | 2014-03-26 | 江苏威耳化工有限公司 | 一种苄氟有机化合物的制备方法 |
| CN102320919B (zh) * | 2011-10-31 | 2014-07-23 | 江苏威耳化工有限公司 | 2，6-二氯-三氟甲苯的制备方法 |
| CN103896728A (zh) * | 2014-02-21 | 2014-07-02 | 江苏丰华化学工业有限公司 | 一种3，4-二氯三氟甲苯的制备方法 |
| US9416073B2 (en) * | 2014-10-06 | 2016-08-16 | Honeywell International Inc. | Method to improve halogenation reactions |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2181554A (en) * | 1936-04-18 | 1939-11-28 | Gen Aniline Works Inc | Benzenecarboxylic acid fluorides containing trifluoromethyl groups and process of preparing them |
| DE1618390A1 (de) * | 1967-03-22 | 1970-12-17 | Hoechst Ag | Verfahren zur Herstellung von Benzolderivaten mit einer oder mehreren Trifluormethylgruppen |
| FR2137744A1 (enExample) * | 1971-05-12 | 1972-12-29 | Comprimo Bv | |
| FR2295004A1 (fr) * | 1974-12-19 | 1976-07-16 | Lonza Ag | Procede pour la fabrication de composes trifluoromethyles aromatiques de la serie benzenique |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1967244A (en) * | 1932-08-31 | 1934-07-24 | Kinetic Chemicals Inc | Production of organic fluorine compounds |
| US3859372A (en) * | 1969-12-03 | 1975-01-07 | Hooker Chemicals Plastics Corp | Process for the preparation of organic fluorine compounds |
| CA1029746A (en) * | 1973-11-10 | 1978-04-18 | Hoechst Aktiengesellschaft | Process for preparing derivatives of benzene fluorinated in the lateral chains |
| US4183873A (en) * | 1976-11-01 | 1980-01-15 | Hooker Chemicals & Plastics Corp. | Liquid phase fluorination process |
| JPS6039048B2 (ja) * | 1976-12-27 | 1985-09-04 | ダイキン工業株式会社 | ベンゾトリフルオライドまたはその誘導体の製法 |
| JPS54130524A (en) * | 1978-03-30 | 1979-10-09 | Daikin Ind Ltd | Preraration of trifluoromethylbenzene or its derivative |
-
1980
- 1980-03-17 FR FR8005877A patent/FR2478074A1/fr active Granted
-
1981
- 1981-03-04 AT AT81400328T patent/ATE3632T1/de not_active IP Right Cessation
- 1981-03-04 EP EP81400328A patent/EP0036352B1/fr not_active Expired
- 1981-03-04 DE DE8181400328T patent/DE3160378D1/de not_active Expired
- 1981-03-12 US US06/243,205 patent/US4462937A/en not_active Expired - Fee Related
- 1981-03-16 IL IL62379A patent/IL62379A/xx unknown
- 1981-03-16 JP JP3666781A patent/JPS572225A/ja active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2181554A (en) * | 1936-04-18 | 1939-11-28 | Gen Aniline Works Inc | Benzenecarboxylic acid fluorides containing trifluoromethyl groups and process of preparing them |
| DE1618390A1 (de) * | 1967-03-22 | 1970-12-17 | Hoechst Ag | Verfahren zur Herstellung von Benzolderivaten mit einer oder mehreren Trifluormethylgruppen |
| FR2137744A1 (enExample) * | 1971-05-12 | 1972-12-29 | Comprimo Bv | |
| FR2295004A1 (fr) * | 1974-12-19 | 1976-07-16 | Lonza Ag | Procede pour la fabrication de composes trifluoromethyles aromatiques de la serie benzenique |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE3632T1 (de) | 1983-06-15 |
| EP0036352A1 (fr) | 1981-09-23 |
| FR2478074B1 (enExample) | 1982-06-25 |
| IL62379A0 (en) | 1981-05-20 |
| US4462937A (en) | 1984-07-31 |
| JPS5754488B2 (enExample) | 1982-11-18 |
| EP0036352B1 (fr) | 1983-06-01 |
| DE3160378D1 (en) | 1983-07-07 |
| IL62379A (en) | 1984-12-31 |
| JPS572225A (en) | 1982-01-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |