CS276566B6 - Process for preparing 1,1-dichlorotetrafluoroethane - Google Patents
Process for preparing 1,1-dichlorotetrafluoroethane Download PDFInfo
- Publication number
- CS276566B6 CS276566B6 CS905322A CS532290A CS276566B6 CS 276566 B6 CS276566 B6 CS 276566B6 CS 905322 A CS905322 A CS 905322A CS 532290 A CS532290 A CS 532290A CS 276566 B6 CS276566 B6 CS 276566B6
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- dichlorotetrafluoroethane
- trichlorotrifluoroethane
- reaction
- cfc
- temperature
- Prior art date
Links
- BAMUEXIPKSRTBS-UHFFFAOYSA-N 1,1-dichloro-1,2,2,2-tetrafluoroethane Chemical compound FC(F)(F)C(F)(Cl)Cl BAMUEXIPKSRTBS-UHFFFAOYSA-N 0.000 title claims description 34
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 28
- 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 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 22
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 18
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 229910052787 antimony Inorganic materials 0.000 claims description 10
- -1 antimony halide Chemical class 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 8
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 239000007791 liquid phase Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000012429 reaction media Substances 0.000 claims description 7
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 238000010924 continuous production Methods 0.000 claims 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 238000003682 fluorination reaction Methods 0.000 description 10
- 239000007789 gas Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 6
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 6
- 239000012808 vapor phase Substances 0.000 description 6
- 238000006317 isomerization reaction Methods 0.000 description 5
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- 229940117975 chromium trioxide Drugs 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 229910001220 stainless steel Inorganic materials 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
- WXGNWUVNYMJENI-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)F WXGNWUVNYMJENI-UHFFFAOYSA-N 0.000 description 2
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 description 2
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- GUNJVIDCYZYFGV-UHFFFAOYSA-K antimony trifluoride Chemical compound F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 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 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004604 Blowing Agent Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 229910000792 Monel Inorganic materials 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910021563 chromium fluoride Inorganic materials 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- QCMJBECJXQJLIL-UHFFFAOYSA-L chromium(6+);oxygen(2-);difluoride Chemical compound [O-2].[O-2].[F-].[F-].[Cr+6] QCMJBECJXQJLIL-UHFFFAOYSA-L 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- YOCUPQPZWBBYIX-UHFFFAOYSA-N copper nickel Chemical compound [Ni].[Cu] YOCUPQPZWBBYIX-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910000623 nickel–chromium alloy Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42912689A | 1989-10-30 | 1989-10-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS532290A3 CS532290A3 (en) | 1992-01-15 |
| CS276566B6 true CS276566B6 (en) | 1992-06-17 |
Family
ID=23701920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS905322A CS276566B6 (en) | 1989-10-30 | 1990-10-30 | Process for preparing 1,1-dichlorotetrafluoroethane |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0426343B1 (de) |
| JP (1) | JP2930697B2 (de) |
| KR (1) | KR950004888B1 (de) |
| CN (1) | CN1026690C (de) |
| AR (1) | AR248389A1 (de) |
| AT (1) | ATE101846T1 (de) |
| AU (1) | AU641190B2 (de) |
| BR (1) | BR9005385A (de) |
| CA (1) | CA2028486A1 (de) |
| CS (1) | CS276566B6 (de) |
| DE (1) | DE69006820T2 (de) |
| ES (1) | ES2062402T3 (de) |
| RU (1) | RU2010789C1 (de) |
| ZA (1) | ZA908686B (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9311742D0 (en) * | 1992-06-10 | 1993-07-21 | Ici Plc | Production of hydrofluoroalkanes |
| US5866730A (en) * | 1993-04-02 | 1999-02-02 | E. I. Du Pont De Nemours And Company | Process for enriching 1,2-dichloro-1,1,2,2-tetrafluoroethane from a mixture of dichlorotetrafluoroethane isomers |
| WO1995012564A1 (en) * | 1993-11-01 | 1995-05-11 | E.I. Du Pont De Nemours And Company | Process for manufacture of high purity 1,1-dichlorotetrafluoroethane |
| US5446216A (en) * | 1993-11-01 | 1995-08-29 | E. I. Du Pont De Nemours And Company | Process for manufacture of high purity 1,1-dichlorotetrafluoroethane |
| US5831136A (en) * | 1994-09-01 | 1998-11-03 | E. I. Du Pont De Nemours And Company | Process for manufacture of high purity 1,1-dichlorotetrafluoroethane |
| CN105621482B (zh) * | 2014-11-05 | 2017-08-25 | 山东森福新材料有限公司 | 氟氯化锑化合物及其制备方法和1,1,2‑三氟三氯乙烷的制备方法 |
| CN110818527A (zh) * | 2019-11-19 | 2020-02-21 | 常熟三爱富氟化工有限责任公司 | 反应精馏制备高纯度1,1,1-三氯三氟乙烷的连续工艺 |
| US20250066276A1 (en) * | 2023-08-22 | 2025-02-27 | Honeywell International Inc. | Catalysts and methods for conversion of 1,1,2-trichloro-1,2,2-trifluoroethane (cfc-113) to 1,1,2-trifluoroethane (hfc-143) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2005713A (en) * | 1933-02-02 | 1935-06-18 | Kinetic Chemicals Inc | Production of fluorinated acyclic hydrocarbons |
| US2005708A (en) * | 1933-08-24 | 1935-06-18 | Kinetic Chemicals Inc | Production of halogenated ethane derivatives containing fluorine |
| US2824900A (en) * | 1954-06-01 | 1958-02-25 | Montedison Spa | Process for the production of 1,1,1-trifluoro-2-chloroethane |
| JPH0788326B2 (ja) * | 1987-11-26 | 1995-09-27 | 旭硝子株式会社 | １，１−ジクロロ−１，２，２，２−テトラフルオロエタンの製造方法 |
-
1990
- 1990-10-19 DE DE69006820T patent/DE69006820T2/de not_active Expired - Fee Related
- 1990-10-19 AT AT90311508T patent/ATE101846T1/de not_active IP Right Cessation
- 1990-10-19 ES ES90311508T patent/ES2062402T3/es not_active Expired - Lifetime
- 1990-10-19 EP EP90311508A patent/EP0426343B1/de not_active Expired - Lifetime
- 1990-10-24 BR BR909005385A patent/BR9005385A/pt not_active Application Discontinuation
- 1990-10-24 CA CA002028486A patent/CA2028486A1/en not_active Abandoned
- 1990-10-29 KR KR1019900017378A patent/KR950004888B1/ko not_active Expired - Fee Related
- 1990-10-29 RU SU904831546A patent/RU2010789C1/ru active
- 1990-10-29 AR AR90318224A patent/AR248389A1/es active
- 1990-10-30 CS CS905322A patent/CS276566B6/cs unknown
- 1990-10-30 CN CN90108727A patent/CN1026690C/zh not_active Expired - Fee Related
- 1990-10-30 AU AU65611/90A patent/AU641190B2/en not_active Ceased
- 1990-10-30 JP JP2290974A patent/JP2930697B2/ja not_active Expired - Lifetime
- 1990-10-30 ZA ZA908686A patent/ZA908686B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2010789C1 (ru) | 1994-04-15 |
| BR9005385A (pt) | 1991-09-17 |
| CA2028486A1 (en) | 1991-05-01 |
| KR950004888B1 (ko) | 1995-05-15 |
| CN1051351A (zh) | 1991-05-15 |
| JP2930697B2 (ja) | 1999-08-03 |
| JPH03218329A (ja) | 1991-09-25 |
| KR910007846A (ko) | 1991-05-30 |
| EP0426343A1 (de) | 1991-05-08 |
| ES2062402T3 (es) | 1994-12-16 |
| DE69006820T2 (de) | 1994-07-28 |
| AR248389A1 (es) | 1995-08-18 |
| EP0426343B1 (de) | 1994-02-23 |
| ZA908686B (en) | 1992-06-24 |
| AU641190B2 (en) | 1993-09-16 |
| AU6561190A (en) | 1991-05-02 |
| ATE101846T1 (de) | 1994-03-15 |
| CN1026690C (zh) | 1994-11-23 |
| DE69006820D1 (de) | 1994-03-31 |
| CS532290A3 (en) | 1992-01-15 |
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