DE2659046C3 - Verfahren zur Herstellung von 1-Chlor- 1,1-difluoräthan und/oder 1,1,1-Trifluoräthan - Google Patents
Verfahren zur Herstellung von 1-Chlor- 1,1-difluoräthan und/oder 1,1,1-TrifluoräthanInfo
- Publication number
- DE2659046C3 DE2659046C3 DE2659046A DE2659046A DE2659046C3 DE 2659046 C3 DE2659046 C3 DE 2659046C3 DE 2659046 A DE2659046 A DE 2659046A DE 2659046 A DE2659046 A DE 2659046A DE 2659046 C3 DE2659046 C3 DE 2659046C3
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- solvent
- hydrofluoric acid
- anhydrous hydrofluoric
- difluoroethane
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 23
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- BHNZEZWIUMJCGF-UHFFFAOYSA-N 1-chloro-1,1-difluoroethane Chemical compound CC(F)(F)Cl BHNZEZWIUMJCGF-UHFFFAOYSA-N 0.000 title description 29
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 71
- 238000006243 chemical reaction Methods 0.000 claims description 57
- 239000002904 solvent Substances 0.000 claims description 37
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 25
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 18
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003990 capacitor Substances 0.000 description 3
- 229960001701 chloroform Drugs 0.000 description 3
- 238000010924 continuous production Methods 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
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- -1 fluorine Hydrogen Chemical class 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229940035339 tri-chlor Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QVLAWKAXOMEXPM-UHFFFAOYSA-N 1,1,1,2-tetrachloroethane Chemical compound ClCC(Cl)(Cl)Cl QVLAWKAXOMEXPM-UHFFFAOYSA-N 0.000 description 1
- BQNSLJQRJAJITR-UHFFFAOYSA-N 1,1,2-trichloro-1,2-difluoroethane Chemical compound FC(Cl)C(F)(Cl)Cl BQNSLJQRJAJITR-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- AFTSHZRGGNMLHC-UHFFFAOYSA-N 1,1-dichloro-1,2,2-trifluoroethane Chemical compound FC(F)C(F)(Cl)Cl AFTSHZRGGNMLHC-UHFFFAOYSA-N 0.000 description 1
- FRCHKSNAZZFGCA-UHFFFAOYSA-N 1,1-dichloro-1-fluoroethane Chemical compound CC(F)(Cl)Cl FRCHKSNAZZFGCA-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- YMRMDGSNYHCUCL-UHFFFAOYSA-N 1,2-dichloro-1,1,2-trifluoroethane Chemical compound FC(Cl)C(F)(F)Cl YMRMDGSNYHCUCL-UHFFFAOYSA-N 0.000 description 1
- IDSKMUOSMAUASS-UHFFFAOYSA-N 1,2-dichloro-1,2-difluoroethane Chemical compound FC(Cl)C(F)Cl IDSKMUOSMAUASS-UHFFFAOYSA-N 0.000 description 1
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 1
- 101100477498 Caenorhabditis elegans shc-1 gene Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XWCDCDSDNJVCLO-UHFFFAOYSA-N Chlorofluoromethane Chemical compound FCCl XWCDCDSDNJVCLO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- FAWGZAFXDJGWBB-UHFFFAOYSA-N antimony(3+) Chemical compound [Sb+3] FAWGZAFXDJGWBB-UHFFFAOYSA-N 0.000 description 1
- UXHQFZRQIWKEOC-UHFFFAOYSA-D antimony(5+) decachloride Chemical compound [Sb](Cl)(Cl)(Cl)(Cl)Cl.[Sb](Cl)(Cl)(Cl)(Cl)Cl UXHQFZRQIWKEOC-UHFFFAOYSA-D 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
- 229940099364 dichlorofluoromethane Drugs 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- RDCHUGMRDPFLDI-UHFFFAOYSA-N trichloro(methoxy)methane Chemical compound COC(Cl)(Cl)Cl RDCHUGMRDPFLDI-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 238000005406 washing 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50157371A JPS5946211B2 (ja) | 1975-12-29 | 1975-12-29 | １− クロロ −１，１− ジフルオロエタンマタハ ／ オヨビ １，１，１− トリフルオロエタンオセイゾウスルホウホウ |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2659046A1 DE2659046A1 (de) | 1977-07-07 |
| DE2659046B2 DE2659046B2 (de) | 1980-09-11 |
| DE2659046C3 true DE2659046C3 (de) | 1981-07-09 |
Family
ID=15648182
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2659046A Expired DE2659046C3 (de) | 1975-12-29 | 1976-12-27 | Verfahren zur Herstellung von 1-Chlor- 1,1-difluoräthan und/oder 1,1,1-Trifluoräthan |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4091043A (enExample) |
| JP (1) | JPS5946211B2 (enExample) |
| DE (1) | DE2659046C3 (enExample) |
| FR (1) | FR2337120A1 (enExample) |
| GB (1) | GB1571915A (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU532945B2 (en) * | 1979-07-23 | 1983-10-20 | British Nuclear Fuels Ltd. | Controlling vapourisation of hydrogen fluoride |
| US4885416A (en) * | 1985-10-18 | 1989-12-05 | E. I. Du Pont De Nemours And Company | Fluorination process |
| FR2617475B1 (fr) * | 1987-07-03 | 1989-12-01 | Atochem | Synthese du chloro-1 difluoro-1,1 ethane |
| JPH0791202B2 (ja) * | 1988-08-05 | 1995-10-04 | 旭硝子株式会社 | １，１−ジクロロ−２，２，２−トリフルオロエタンの製造法 |
| US4962244A (en) * | 1989-04-03 | 1990-10-09 | Atochem North America, Inc. | Process for producing 1,1-dichloro-1-fluoroethane and/or 1-chloro-1,1-difluoroethane free of vinylidene chloride |
| US4975156A (en) * | 1989-05-04 | 1990-12-04 | Atochem North America, Inc. | Process for the separation of hydrogen fluoride, 1,1-dichloro-1-fluoroethane and 1-chloro-1,1-difluoroethane from liquid mixtures thereof |
| FR2652573B1 (fr) * | 1989-10-03 | 1991-12-13 | Atochem | Procede de fabrication du 1,1,1-chlorodifluoroethane. |
| BE1005095A3 (fr) * | 1991-07-10 | 1993-04-20 | Solvay | Procede pour la preparation de 1,1-dichloro-1,3,3,3-tetrafluoropropane. |
| US5482682A (en) * | 1993-05-17 | 1996-01-09 | Florida Scientific Laboratories Inc. | Apparatus for direct fluorination of a hydrocarbon by molecular fluorine gas |
| US5639924A (en) * | 1994-11-29 | 1997-06-17 | Elf Atochem North America, Inc. | Process for the production of 1,1,1-trifluoroethane |
| KR0152580B1 (ko) * | 1995-08-23 | 1998-10-15 | 김은영 | 1,1,1,2-테트라플루오로에탄, 펜타플루오로에탄 및 1,1,1-트리플루오로에탄의 병산 방법 |
| AU5401698A (en) * | 1996-12-06 | 1998-06-29 | Advanced Phytonics Limited | Materials treatment |
| JP2001523652A (ja) * | 1997-11-18 | 2001-11-27 | アライドシグナル・インコーポレイテッド | ジフルオロメタンの製造方法 |
| DE69921964D1 (de) | 1998-01-16 | 2004-12-23 | Allied Signal Inc | Verfahren zur herstellung von organischen fluorverbindungen |
| US6153802A (en) * | 1998-05-08 | 2000-11-28 | Alliedsignal Inc. | Liquid-fluorination system and method |
| US6080899A (en) * | 1999-01-25 | 2000-06-27 | Alliedsignal Inc. | Method of producing fluorinated organic compounds |
| US7071368B1 (en) * | 2005-02-09 | 2006-07-04 | Honeywell International Inc. | Method of making 1,1,1-trifluoroethane |
| US8889925B2 (en) * | 2010-03-10 | 2014-11-18 | Arkema France | Process of fluorination in liquid phase |
| WO2012066375A1 (en) * | 2010-11-15 | 2012-05-24 | Arkema France | Process for the manufacture of 2 - chloro - 3, 3, 3 - trifluoropropene (hcfo 1233xf) by liquid phase fluorination of pentachloropropane |
| JP6014584B2 (ja) * | 2010-04-26 | 2016-10-25 | アルケマ フランス | ペンタクロロプロパンの液相フッ素化による２−クロロ−３，３，３−トリフルオロプロペン（ＨＣＦＯ１２３３ｘｆ）の製造方法 |
| CN102614678B (zh) * | 2012-03-09 | 2014-01-22 | 常熟三爱富氟化工有限责任公司 | 一氟二氯乙烷生产中分离回收二氟一氯乙烷装置及工艺 |
| FR3008093B1 (fr) * | 2013-07-04 | 2015-12-11 | Rhodia Operations | Procede de fluoration de composes halogenures de sulfonyle |
| CN103920296B (zh) * | 2013-12-20 | 2016-05-25 | 沈文奎 | 低*热源驱动型溶液浓缩-纯化机组 |
| CN114409499B (zh) * | 2020-10-28 | 2024-02-27 | 常熟三爱富中昊化工新材料有限公司 | 1,1-二氟乙烯的制备方法 |
| CN112299948A (zh) * | 2020-12-01 | 2021-02-02 | 山东华安新材料有限公司 | 一种1，1，1-三氟-2-氯乙烷的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2005710A (en) * | 1931-05-20 | 1935-06-18 | Kinetic Chemicals Inc | Preparation of fluorine compounds |
| JPS505681B1 (enExample) * | 1970-07-28 | 1975-03-06 |
-
1975
- 1975-12-29 JP JP50157371A patent/JPS5946211B2/ja not_active Expired
-
1976
- 1976-12-21 US US05/752,926 patent/US4091043A/en not_active Expired - Lifetime
- 1976-12-23 GB GB53982/76A patent/GB1571915A/en not_active Expired
- 1976-12-27 DE DE2659046A patent/DE2659046C3/de not_active Expired
- 1976-12-29 FR FR7639492A patent/FR2337120A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5946211B2 (ja) | 1984-11-10 |
| JPS5283402A (en) | 1977-07-12 |
| DE2659046B2 (de) | 1980-09-11 |
| DE2659046A1 (de) | 1977-07-07 |
| GB1571915A (en) | 1980-07-23 |
| US4091043A (en) | 1978-05-23 |
| FR2337120B1 (enExample) | 1980-03-21 |
| FR2337120A1 (fr) | 1977-07-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) |