JP2003513059A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2003513059A5 JP2003513059A5 JP2001534748A JP2001534748A JP2003513059A5 JP 2003513059 A5 JP2003513059 A5 JP 2003513059A5 JP 2001534748 A JP2001534748 A JP 2001534748A JP 2001534748 A JP2001534748 A JP 2001534748A JP 2003513059 A5 JP2003513059 A5 JP 2003513059A5
- Authority
- JP
- Japan
- Prior art keywords
- stream
- product stream
- reactor
- crude product
- separation
- 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
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 200
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 197
- 239000000047 product Substances 0.000 description 177
- 238000000034 method Methods 0.000 description 141
- 239000012043 crude product Substances 0.000 description 117
- 238000004821 distillation Methods 0.000 description 71
- 238000000926 separation method Methods 0.000 description 66
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 61
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 51
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 51
- 239000000543 intermediate Substances 0.000 description 50
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 36
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 35
- 229950011008 tetrachloroethylene Drugs 0.000 description 35
- 238000009835 boiling Methods 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 33
- 238000005191 phase separation Methods 0.000 description 25
- 238000003682 fluorination reaction Methods 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- 238000004519 manufacturing process Methods 0.000 description 16
- 238000000746 purification Methods 0.000 description 15
- 238000004064 recycling Methods 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 14
- 239000007795 chemical reaction product Substances 0.000 description 13
- 239000012071 phase Substances 0.000 description 13
- 239000006227 byproduct Substances 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 239000007791 liquid phase Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- -1 ethane halide Chemical class 0.000 description 11
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 description 11
- BOUGCJDAQLKBQH-UHFFFAOYSA-N 1-chloro-1,2,2,2-tetrafluoroethane Chemical compound FC(Cl)C(F)(F)F BOUGCJDAQLKBQH-UHFFFAOYSA-N 0.000 description 10
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 7
- 238000004140 cleaning Methods 0.000 description 6
- 239000003518 caustics Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005406 washing 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007806 chemical reaction intermediate Substances 0.000 description 3
- 150000001875 compounds Chemical class 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
- 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 229910000423 chromium oxide Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007670 refining Methods 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
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-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
- 238000010936 aqueous wash Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 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
- 238000007796 conventional method Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 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
- 238000010348 incorporation Methods 0.000 description 1
- 238000011545 laboratory measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- QVRVXSZKCXFBTE-UHFFFAOYSA-N n-[4-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)butyl]-2-(2-fluoroethoxy)-5-methylbenzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCCCNC(=O)C1=CC(C)=CC=C1OCCF QVRVXSZKCXFBTE-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 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
- 238000004088 simulation Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000126 substance Substances 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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/432,748 US6417413B1 (en) | 1999-11-03 | 1999-11-03 | Process for the preparation of halogenated ethanes |
| US09/432,748 | 1999-11-03 | ||
| PCT/US2000/030091 WO2001032592A1 (en) | 1999-11-03 | 2000-11-01 | Process for the preparation of halogenated ethanes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003513059A JP2003513059A (ja) | 2003-04-08 |
| JP2003513059A5 true JP2003513059A5 (https=) | 2010-12-09 |
| JP4897171B2 JP4897171B2 (ja) | 2012-03-14 |
Family
ID=23717444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001534748A Expired - Fee Related JP4897171B2 (ja) | 1999-11-03 | 2000-11-01 | ハロゲン化エタンの調製プロセス |
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 |
| GB0525699D0 (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 |
| GB0525700D0 (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 |
| JP5146466B2 (ja) * | 2007-12-14 | 2013-02-20 | ダイキン工業株式会社 | 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 |
| DE69112514T3 (de) | 1990-06-29 | 1999-10-21 | Sumitomo Chemical Co., Ltd. | Wärmebeständige Übergangsalumina und Verfahren zu deren Herstellung. |
| 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 |
| JPH05255144A (ja) * | 1991-11-15 | 1993-10-05 | Hoechst Ag | 弗化水素および１−クロロ−２，２，２−トリフルオロエタンを含有する混合物の分離方法 |
| 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 |
| ES2147857T3 (es) | 1994-10-07 | 2000-10-01 | Daikin Ind Ltd | Procedimiento que permite separar pentafluoroetano y procedimiento de preparacion de pentafluoroetano con la ayuda de dicho procedimiento de separacion. |
-
1999
- 1999-11-03 US US09/432,748 patent/US6417413B1/en not_active Expired - Lifetime
-
2000
- 2000-11-01 WO PCT/US2000/030091 patent/WO2001032592A1/en not_active Ceased
- 2000-11-01 AT AT00976785T patent/ATE356106T1/de not_active IP Right Cessation
- 2000-11-01 KR KR1020027005787A patent/KR100846231B1/ko not_active Expired - Fee Related
- 2000-11-01 EP EP00976785A patent/EP1226100B1/en not_active Expired - Lifetime
- 2000-11-01 DE DE60033836T patent/DE60033836T2/de not_active Expired - Lifetime
- 2000-11-01 MX MXPA02004431A patent/MXPA02004431A/es active IP Right Grant
- 2000-11-01 BR BR0015291-9A patent/BR0015291A/pt not_active IP Right Cessation
- 2000-11-01 ES ES00976785T patent/ES2282146T3/es not_active Expired - Lifetime
- 2000-11-01 JP JP2001534748A patent/JP4897171B2/ja not_active Expired - Fee Related
- 2000-11-01 AU AU14516/01A patent/AU1451601A/en not_active Abandoned
- 2000-11-01 CA CA002389803A patent/CA2389803A1/en not_active Abandoned
- 2000-12-08 TW TW089123101A patent/TW483880B/zh not_active IP Right Cessation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102307831B (zh) | (z)-1-氯-3,3,3-三氟丙烯的精制方法 | |
| EP0864554B1 (en) | Method for purifying crude 1,1,1,3,3-pentafluoropropane | |
| JP5788380B2 (ja) | フッ化水素からのｒ−１２３３の分離 | |
| US5763706A (en) | Process for the manufacture of 1,1,1,3,3-pentafluoropropane and 1,1,1,3,3,3-hexafluoropropane | |
| EP0734366B1 (en) | Production of pentafluoroethane | |
| US6759381B1 (en) | Azeotrope-like compositions of 1-chloro-1,3,3,3-tetrafluoropropane and 1,2-dichloro-3,3,3-trifluoropropene | |
| EP0840719B1 (en) | Distillation processes for recovering HFC-125 and HFC-32 | |
| US20050013764A1 (en) | Methods of purifying hydrogen fluoride | |
| JP3279449B2 (ja) | フッ化水素及びジフルオロメタンの分離方法 | |
| US7214839B2 (en) | Method of making hydrofluorocarbons | |
| WO2019152368A1 (en) | PROCESS FOR THE PRODUCTION OF 1-CHLORO-3,3,3-TRIFLUOROPROPENE (HCFO-1233zd) | |
| JP4897171B2 (ja) | ハロゲン化エタンの調製プロセス | |
| KR100504672B1 (ko) | 플루오르화수소 회수 방법 | |
| JPH11116511A (ja) | １，１，１，２，２−ペンタフルオロエタンの製造方法 | |
| JP2003513059A5 (https=) | ||
| JP3853397B2 (ja) | ペンタフルオロエタンの製造方法及びペンタフルオロエタンに転化するのに適当な組成物 | |
| JPH10310541A (ja) | １，１，１，３，３−ペンタフルオロプロパンの分離方法 | |
| US20020183568A1 (en) | Process for producing hexafluoroethane and use thereof | |
| KR20020082793A (ko) | Ｈｆｃ-32의 회수방법 | |
| JP2001520208A (ja) | フッ化水素から１，１，１，３，３−ペンタフルオロプロパンを分離する方法 | |
| EP1029840A1 (en) | Process for separating HFC-32 and HFC-125 |