CS79791A2 - Method of hydrogenfluorochlorinated hydrocarbons isomerization - Google Patents
Method of hydrogenfluorochlorinated hydrocarbons isomerization Download PDFInfo
- Publication number
- CS79791A2 CS79791A2 CS91797A CS79791A CS79791A2 CS 79791 A2 CS79791 A2 CS 79791A2 CS 91797 A CS91797 A CS 91797A CS 79791 A CS79791 A CS 79791A CS 79791 A2 CS79791 A2 CS 79791A2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hcfc
- isomerization
- dichloro
- difluoroethane
- chloro
- Prior art date
Links
- 238000006317 isomerization reaction Methods 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 25
- 229930195733 hydrocarbon Natural products 0.000 title 1
- 150000002430 hydrocarbons Chemical class 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims description 32
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 claims description 16
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 16
- -1 polytetrafluoroethylene Polymers 0.000 claims description 15
- 238000001354 calcination Methods 0.000 claims description 11
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 11
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 11
- YMRMDGSNYHCUCL-UHFFFAOYSA-N 1,2-dichloro-1,1,2-trifluoroethane Chemical compound FC(Cl)C(F)(F)Cl YMRMDGSNYHCUCL-UHFFFAOYSA-N 0.000 claims description 9
- BHNZEZWIUMJCGF-UHFFFAOYSA-N 1-chloro-1,1-difluoroethane Chemical compound CC(F)(F)Cl BHNZEZWIUMJCGF-UHFFFAOYSA-N 0.000 claims description 7
- BOUGCJDAQLKBQH-UHFFFAOYSA-N 1-chloro-1,2,2,2-tetrafluoroethane Chemical compound FC(Cl)C(F)(F)F BOUGCJDAQLKBQH-UHFFFAOYSA-N 0.000 claims description 7
- SKDFWEPBABSFMG-UHFFFAOYSA-N 1,2-dichloro-1,1-difluoroethane Chemical compound FC(F)(Cl)CCl SKDFWEPBABSFMG-UHFFFAOYSA-N 0.000 claims description 6
- JQZFYIGAYWLRCC-UHFFFAOYSA-N 1-chloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)(F)Cl JQZFYIGAYWLRCC-UHFFFAOYSA-N 0.000 claims description 6
- VLIDBBNDBSNADN-UHFFFAOYSA-N 1,1-dichloro-2,2-difluoroethane Chemical compound FC(F)C(Cl)Cl VLIDBBNDBSNADN-UHFFFAOYSA-N 0.000 claims description 4
- IDSKMUOSMAUASS-UHFFFAOYSA-N 1,2-dichloro-1,2-difluoroethane Chemical compound FC(Cl)C(F)Cl IDSKMUOSMAUASS-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- AFTSHZRGGNMLHC-UHFFFAOYSA-N 1,1-dichloro-1,2,2-trifluoroethane Chemical compound FC(F)C(F)(Cl)Cl AFTSHZRGGNMLHC-UHFFFAOYSA-N 0.000 claims description 2
- 229910017075 AlFxOy Inorganic materials 0.000 claims description 2
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 claims 1
- 229910018404 Al2 O3 Inorganic materials 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 235000015250 liver sausages Nutrition 0.000 claims 1
- XYSQXZCMOLNHOI-UHFFFAOYSA-N s-[2-[[4-(acetylsulfamoyl)phenyl]carbamoyl]phenyl] 5-pyridin-1-ium-1-ylpentanethioate;bromide Chemical compound [Br-].C1=CC(S(=O)(=O)NC(=O)C)=CC=C1NC(=O)C1=CC=CC=C1SC(=O)CCCC[N+]1=CC=CC=C1 XYSQXZCMOLNHOI-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 description 14
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 230000007423 decrease Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- ATEBGNALLCMSGS-UHFFFAOYSA-N 2-chloro-1,1-difluoroethane Chemical compound FC(F)CCl ATEBGNALLCMSGS-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical class 0.000 description 3
- 206010061592 cardiac fibrillation Diseases 0.000 description 3
- 230000002600 fibrillogenic effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 2
- UOVSDUIHNGNMBZ-UHFFFAOYSA-N 1-chloro-1,2-difluoroethane Chemical compound FCC(F)Cl UOVSDUIHNGNMBZ-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000004088 foaming agent Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000221931 Hypomyces rosellus Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 230000000779 depleting effect Effects 0.000 description 1
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910001388 sodium aluminate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
- C01F7/00—Compounds of aluminium
- C01F7/48—Halides, with or without other cations besides aluminium
- C01F7/50—Fluorides
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/12—Fluorides
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/125—Halogens; Compounds thereof with scandium, yttrium, aluminium, gallium, indium or thallium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/358—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by isomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
- C07C19/12—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine having two carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Geology (AREA)
- Inorganic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2083000A JPH03284637A (ja) | 1990-03-31 | 1990-03-31 | ハイドロクロロフルオロカーボンの異性化方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS79791A2 true CS79791A2 (en) | 1991-11-12 |
Family
ID=13789966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS91797A CS79791A2 (en) | 1990-03-31 | 1991-03-26 | Method of hydrogenfluorochlorinated hydrocarbons isomerization |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5118887A (pt) |
| EP (1) | EP0450467A3 (pt) |
| JP (1) | JPH03284637A (pt) |
| KR (1) | KR910016656A (pt) |
| CN (1) | CN1024787C (pt) |
| AU (1) | AU634942B2 (pt) |
| BR (1) | BR9101262A (pt) |
| CA (1) | CA2039430A1 (pt) |
| CS (1) | CS79791A2 (pt) |
| RU (1) | RU2021247C1 (pt) |
| ZA (1) | ZA912381B (pt) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1251951B (it) * | 1991-10-18 | 1995-05-27 | Ausimont Spa | Procedimento per purificare 1,1,1-trifluoro-,2,2 dicloroetano dall`isomero 1,1,2-trifluoro-1,2-dicloroetano. |
| IT1251957B (it) * | 1991-10-18 | 1995-05-27 | Ausimont Spa | Procedimento per isomerizzare 1,1,2-trifluoro-1,2-dicloroetano a 1,1,1- trifluoro-2,2,-dicloroetano |
| US5302766A (en) * | 1993-06-03 | 1994-04-12 | E. I. Du Pont De Nemours And Company | Isomerization process |
| JPH09502223A (ja) * | 1993-09-03 | 1997-03-04 | イー・アイ・デュポン・ドゥ・ヌムール・アンド・カンパニー | 使用済みアルミニウムクロロフルオライドからのアルミニウム有価物および／または弗化物有価物の回収 |
| WO1995011875A1 (en) * | 1993-10-28 | 1995-05-04 | Alliedsignal Inc. | Process for purifying 1,1-dichloro-2,2,2-trifluoroethane and 1-chloro-1,2,2,2-tetrafluoroethane |
| EP1502906A1 (en) * | 2003-07-31 | 2005-02-02 | Solvay Solexis S.p.A. | Process for activation of AIF3 based catalysts and process for isomerising hydrochlorofluorocarbons |
| CN105294387B (zh) * | 2015-10-22 | 2017-04-05 | 北京宇极科技发展有限公司 | 制备氯氟环戊烯同分异构体的方法 |
| JP7036024B2 (ja) * | 2016-11-01 | 2022-03-15 | Ａｇｃ株式会社 | 有機化合物の異性化方法及び有機化合物の異性体の製造方法 |
| WO2020069972A1 (en) * | 2018-10-02 | 2020-04-09 | Basf Se | Processes for carrying out chemical reactions in fluid phase in the presence of films comprising catalyst particles |
| RU2706363C1 (ru) * | 2019-06-14 | 2019-11-18 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Уфимский государственный нефтяной технический университет" | Способ получения гем-дихлорциклопентенов |
| CN113292392B (zh) * | 2021-04-16 | 2022-10-28 | 台州益普高分子材料有限公司 | 一种饱和氢氯氟碳化物间的重排反应及其制备含氟醇的方法 |
| CN114853563B (zh) * | 2022-06-27 | 2024-06-28 | 山东华安新材料有限公司 | 一种2-氯-1,1-二氟乙烷的制备方法 |
| CN117229121B (zh) * | 2023-11-14 | 2024-04-05 | 山东海化集团有限公司 | 一种2-氯-1,1-二氟乙烷的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52121710A (en) * | 1976-04-05 | 1977-10-13 | Mitsubishi Electric Corp | Preparing of stator for canned motor |
| JPS53121710A (en) * | 1977-03-30 | 1978-10-24 | Daikin Ind Ltd | Preparation of isomerized chlorofluorohydrocarbon containing hydrogne |
| JPS59209645A (ja) * | 1983-05-12 | 1984-11-28 | Nippon Oil Co Ltd | 触媒担体の製造方法 |
| US4902838A (en) * | 1988-12-28 | 1990-02-20 | E. I. Du Pont De Nemours And Company | Isomerization of saturated fluorohydrocarbons |
| ATE99662T1 (de) * | 1989-05-25 | 1994-01-15 | Du Pont | Verfahren zur herstellung von 1,1-dichlor-1fluorethan. |
-
1990
- 1990-03-31 JP JP2083000A patent/JPH03284637A/ja active Pending
-
1991
- 1991-03-21 KR KR1019910004423A patent/KR910016656A/ko not_active Abandoned
- 1991-03-26 CS CS91797A patent/CS79791A2/cs unknown
- 1991-03-26 EP EP19910104762 patent/EP0450467A3/en not_active Ceased
- 1991-03-27 AU AU73841/91A patent/AU634942B2/en not_active Ceased
- 1991-03-28 BR BR919101262A patent/BR9101262A/pt not_active Application Discontinuation
- 1991-03-28 ZA ZA912381A patent/ZA912381B/xx unknown
- 1991-03-28 US US07/676,279 patent/US5118887A/en not_active Expired - Fee Related
- 1991-03-28 CA CA002039430A patent/CA2039430A1/en not_active Abandoned
- 1991-03-29 RU SU914895047A patent/RU2021247C1/ru active
- 1991-03-30 CN CN91102051A patent/CN1024787C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BR9101262A (pt) | 1991-11-05 |
| ZA912381B (en) | 1992-01-29 |
| CN1055354A (zh) | 1991-10-16 |
| US5118887A (en) | 1992-06-02 |
| CN1024787C (zh) | 1994-06-01 |
| AU7384191A (en) | 1991-10-03 |
| RU2021247C1 (ru) | 1994-10-15 |
| EP0450467A3 (en) | 1992-07-01 |
| JPH03284637A (ja) | 1991-12-16 |
| EP0450467A2 (en) | 1991-10-09 |
| CA2039430A1 (en) | 1991-10-01 |
| KR910016656A (ko) | 1991-11-05 |
| AU634942B2 (en) | 1993-03-04 |
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