CA2389803A1 - Process for the preparation of halogenated ethanes - Google Patents
Process for the preparation of halogenated ethanes Download PDFInfo
- Publication number
- CA2389803A1 CA2389803A1 CA002389803A CA2389803A CA2389803A1 CA 2389803 A1 CA2389803 A1 CA 2389803A1 CA 002389803 A CA002389803 A CA 002389803A CA 2389803 A CA2389803 A CA 2389803A CA 2389803 A1 CA2389803 A1 CA 2389803A1
- Authority
- CA
- Canada
- Prior art keywords
- stream
- product stream
- crude product
- reactor
- separating
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 103
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 238000002360 preparation method Methods 0.000 title claims description 8
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 179
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 172
- 239000000047 product Substances 0.000 claims abstract description 151
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 239000000203 mixture Substances 0.000 claims abstract description 16
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000012043 crude product Substances 0.000 claims description 88
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 58
- 238000004821 distillation Methods 0.000 claims description 57
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 52
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 52
- 238000009835 boiling Methods 0.000 claims description 27
- 239000013067 intermediate product Substances 0.000 claims description 24
- 238000005191 phase separation Methods 0.000 claims description 17
- 238000003682 fluorination reaction Methods 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 239000007791 liquid phase Substances 0.000 claims description 9
- 238000004064 recycling Methods 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 6
- 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 6
- 238000004519 manufacturing process Methods 0.000 abstract description 15
- 239000006227 byproduct Substances 0.000 abstract description 13
- 239000011541 reaction mixture Substances 0.000 abstract description 3
- -1 pentafluoroethane Chemical class 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 description 29
- 239000000543 intermediate Substances 0.000 description 16
- 239000012071 phase Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 12
- 239000000463 material Substances 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 239000003518 caustics Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000005201 scrubbing Methods 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 238000005200 wet scrubbing Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000007806 chemical reaction intermediate Substances 0.000 description 2
- 229910000423 chromium oxide Inorganic materials 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- RFCAUADVODFSLZ-UHFFFAOYSA-N 1-Chloro-1,1,2,2,2-pentafluoroethane Chemical compound FC(F)(F)C(F)(F)Cl RFCAUADVODFSLZ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 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
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 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
- 238000005094 computer simulation Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000011545 laboratory measurement Methods 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
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000002351 wastewater Substances 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
- C07C17/21—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms with simultaneous increase of the number of halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/432,748 | 1999-11-03 | ||
| US09/432,748 US6417413B1 (en) | 1999-11-03 | 1999-11-03 | Process for the preparation of halogenated ethanes |
| PCT/US2000/030091 WO2001032592A1 (en) | 1999-11-03 | 2000-11-01 | Process for the preparation of halogenated ethanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2389803A1 true CA2389803A1 (en) | 2001-05-10 |
Family
ID=23717444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002389803A Abandoned CA2389803A1 (en) | 1999-11-03 | 2000-11-01 | Process for the preparation of halogenated ethanes |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6417413B1 (https=) |
| EP (1) | EP1226100B1 (https=) |
| JP (1) | JP4897171B2 (https=) |
| KR (1) | KR100846231B1 (https=) |
| AT (1) | ATE356106T1 (https=) |
| AU (1) | AU1451601A (https=) |
| BR (1) | BR0015291A (https=) |
| CA (1) | CA2389803A1 (https=) |
| DE (1) | DE60033836T2 (https=) |
| ES (1) | ES2282146T3 (https=) |
| MX (1) | MXPA02004431A (https=) |
| TW (1) | TW483880B (https=) |
| WO (1) | WO2001032592A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070032688A1 (en) * | 2002-08-02 | 2007-02-08 | Beatrice Boussand | Process for preparing 1,1,1-trifluoro-2, 2-dichloroethane |
| GB0525700D0 (en) * | 2005-12-17 | 2006-01-25 | Ineos Fluor Holdings Ltd | Process |
| GB0525701D0 (en) * | 2005-12-17 | 2006-01-25 | Ineos Fluor Holdings Ltd | Process |
| GB0525699D0 (en) | 2005-12-17 | 2006-01-25 | Ineos Fluor Holdings Ltd | Process |
| CN100999439B (zh) * | 2007-01-04 | 2010-10-06 | 西安近代化学研究所 | 五氟乙烷的制备方法 |
| WO2009078234A1 (ja) * | 2007-12-14 | 2009-06-25 | Daikin Industries, Ltd. | ペンタフルオロエタンの製造方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE445560C (de) | 1925-10-24 | 1927-06-30 | Fried Krupp Grusonwerk Akt Ges | Verstellungen der Druckspindeln in Walzgeruesten |
| DE542290C (de) | 1930-03-18 | 1932-01-22 | Otto Andrew Maunula | OElfilter fuer Brennkraftmaschinen |
| US3258500A (en) | 1959-08-17 | 1966-06-28 | Du Pont | Process for fluorinating halohydro-carbons |
| GB1307224A (en) | 1969-06-27 | 1973-02-14 | Ici Ltd | Chromium oxide catalyst |
| IT1202652B (it) | 1987-03-09 | 1989-02-09 | Ausimont Spa | Processo per la preparazione di 1,1,1-trifluoro-2,2-dicloroetano mediante idrofluorurazione in presenza di catalizzatori |
| US4843181A (en) | 1987-10-22 | 1989-06-27 | E. I. Du Pont De Nemours And Company | Process for the manufacture of 1,1,1-trifluorodichloroethane and 1,1,1,2-tetrafluorochloroethane |
| US4911792A (en) | 1988-08-01 | 1990-03-27 | E. I. Du Pont De Nemours And Company | Process for the separation of HF via phase separation and distillation |
| US5094773A (en) | 1988-08-01 | 1992-03-10 | E. I. Du Pont De Nemours And Company | Azeotropes of HF and process for the separation of HF via azeotropic distillation |
| DE4005945A1 (de) * | 1990-02-26 | 1991-08-29 | Kali Chemie Ag | Verfahren zur herstellung von aethanderivaten |
| EP0464627B2 (en) | 1990-06-29 | 1999-03-24 | Sumitomo Chemical Company Limited | Heat resistant transition alumina and process for producing the same |
| ZA923274B (en) | 1991-05-06 | 1993-11-08 | Du Pont | Process for the manufacture of pentafluoroethane |
| US5087329A (en) | 1991-05-16 | 1992-02-11 | E. I. Du Pont De Nemours And Company | Process for separating pentafluoroethane from a mixture of halogenated hydrocarbons containing chloropentafluoroethane |
| CA2082844A1 (en) * | 1991-11-15 | 1993-05-16 | Wolfgang Dukat | Process for the separation of a mixture containing hydrogen fluoride and 1-chloro-2,2,2-trifluoroethane |
| IT1256631B (it) | 1992-12-10 | 1995-12-12 | Ausimont Spa | Procedimento per la separazione di hf da sue miscele con gli idroclorofluorcarburi 123 e/o 124 |
| US5346595A (en) | 1993-02-23 | 1994-09-13 | Alliedsignal Inc. | Process for the purification of a pentafluoroethane azeotrope |
| US5545778A (en) | 1994-05-25 | 1996-08-13 | Alliedsignal Inc. | Single stage process for producing hydrofluorocarbons from perchloroethylene |
| EP0805137B1 (en) | 1994-10-07 | 2000-05-17 | Daikin Industries, Limited | Method of separating pentafluoroethane and process for producing pentafluoroethane by utilizing said method |
-
1999
- 1999-11-03 US US09/432,748 patent/US6417413B1/en not_active Expired - Lifetime
-
2000
- 2000-11-01 MX MXPA02004431A patent/MXPA02004431A/es active IP Right Grant
- 2000-11-01 DE DE60033836T patent/DE60033836T2/de not_active Expired - Lifetime
- 2000-11-01 EP EP00976785A patent/EP1226100B1/en not_active Expired - Lifetime
- 2000-11-01 WO PCT/US2000/030091 patent/WO2001032592A1/en not_active Ceased
- 2000-11-01 AU AU14516/01A patent/AU1451601A/en not_active Abandoned
- 2000-11-01 BR BR0015291-9A patent/BR0015291A/pt not_active IP Right Cessation
- 2000-11-01 JP JP2001534748A patent/JP4897171B2/ja not_active Expired - Fee Related
- 2000-11-01 CA CA002389803A patent/CA2389803A1/en not_active Abandoned
- 2000-11-01 KR KR1020027005787A patent/KR100846231B1/ko not_active Expired - Fee Related
- 2000-11-01 AT AT00976785T patent/ATE356106T1/de not_active IP Right Cessation
- 2000-11-01 ES ES00976785T patent/ES2282146T3/es not_active Expired - Lifetime
- 2000-12-08 TW TW089123101A patent/TW483880B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BR0015291A (pt) | 2003-02-25 |
| DE60033836T2 (de) | 2007-09-20 |
| ES2282146T3 (es) | 2007-10-16 |
| WO2001032592A1 (en) | 2001-05-10 |
| ATE356106T1 (de) | 2007-03-15 |
| DE60033836D1 (de) | 2007-04-19 |
| TW483880B (en) | 2002-04-21 |
| JP2003513059A (ja) | 2003-04-08 |
| US6417413B1 (en) | 2002-07-09 |
| AU1451601A (en) | 2001-05-14 |
| JP4897171B2 (ja) | 2012-03-14 |
| MXPA02004431A (es) | 2002-09-02 |
| EP1226100B1 (en) | 2007-03-07 |
| KR100846231B1 (ko) | 2008-07-15 |
| KR20020050256A (ko) | 2002-06-26 |
| EP1226100A1 (en) | 2002-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |