PL208572B1 - Sposób wytwarzania hydrofluoroalkanu, którym jest 1,1,1,3,3- pentafluorobutan - Google Patents
Sposób wytwarzania hydrofluoroalkanu, którym jest 1,1,1,3,3- pentafluorobutanInfo
- Publication number
- PL208572B1 PL208572B1 PL385267A PL38526799A PL208572B1 PL 208572 B1 PL208572 B1 PL 208572B1 PL 385267 A PL385267 A PL 385267A PL 38526799 A PL38526799 A PL 38526799A PL 208572 B1 PL208572 B1 PL 208572B1
- Authority
- PL
- Poland
- Prior art keywords
- reaction
- hydrogen fluoride
- hydrofluorobutane
- mixture
- pentafluorobutane
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 37
- 150000005828 hydrofluoroalkanes Chemical class 0.000 title claims description 27
- 238000004519 manufacturing process Methods 0.000 title claims description 18
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 76
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 74
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000006243 chemical reaction Methods 0.000 claims description 69
- 239000003054 catalyst Substances 0.000 claims description 41
- FFBFEBDZFWMXBE-UHFFFAOYSA-N 1,1,1,3,3-pentachlorobutane Chemical compound CC(Cl)(Cl)CC(Cl)(Cl)Cl FFBFEBDZFWMXBE-UHFFFAOYSA-N 0.000 claims description 14
- 239000007791 liquid phase Substances 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 12
- VAOMKNAMFFGULC-UHFFFAOYSA-N 2,3-dichloro-1,1,1-trifluorobutane Chemical class FC(C(C(C)Cl)Cl)(F)F VAOMKNAMFFGULC-UHFFFAOYSA-N 0.000 claims description 3
- 238000000926 separation method Methods 0.000 abstract description 14
- 150000001875 compounds Chemical group 0.000 abstract description 4
- 238000000605 extraction Methods 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 description 65
- 239000002243 precursor Substances 0.000 description 44
- 238000004821 distillation Methods 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 21
- 239000007795 chemical reaction product Substances 0.000 description 14
- 239000000543 intermediate Substances 0.000 description 14
- 239000012535 impurity Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- 241000196324 Embryophyta Species 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 150000002894 organic compounds Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 6
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- -1 1,1,1,3,3-pentafluorobutane hydrofluoroalkane Chemical class 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000003682 fluorination reaction Methods 0.000 description 4
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- MRKAIYYTIQVWCK-UHFFFAOYSA-N 1,1-dichloro-1,3,3-trifluorobutane Chemical compound CC(F)(F)CC(F)(Cl)Cl MRKAIYYTIQVWCK-UHFFFAOYSA-N 0.000 description 2
- XPAUQCAVYXOWFR-UHFFFAOYSA-N 1,1-dichloro-1,3-difluorobut-2-ene Chemical compound CC(F)=CC(F)(Cl)Cl XPAUQCAVYXOWFR-UHFFFAOYSA-N 0.000 description 2
- JZKJJRVPJFNKMB-UHFFFAOYSA-N 1,3-dichloro-1,1,3-trifluorobutane Chemical compound CC(F)(Cl)CC(F)(F)Cl JZKJJRVPJFNKMB-UHFFFAOYSA-N 0.000 description 2
- BSERHUYXVAIRSG-UHFFFAOYSA-N 1-chloro-1,1,3,3-tetrafluorobutane Chemical compound CC(F)(F)CC(F)(F)Cl BSERHUYXVAIRSG-UHFFFAOYSA-N 0.000 description 2
- DOSUCSMNYNCWBY-UHFFFAOYSA-N 1-chloro-1,1,3-trifluorobut-2-ene Chemical class CC(F)=CC(F)(F)Cl DOSUCSMNYNCWBY-UHFFFAOYSA-N 0.000 description 2
- KQBWUCNIYWMKEK-UHFFFAOYSA-N 1-chloro-1-fluorobut-1-ene Chemical class CCC=C(F)Cl KQBWUCNIYWMKEK-UHFFFAOYSA-N 0.000 description 2
- HFZJRXWWTAKJAO-UHFFFAOYSA-N 3,3-dichloro-1,1,1-trifluorobutane Chemical compound CC(Cl)(Cl)CC(F)(F)F HFZJRXWWTAKJAO-UHFFFAOYSA-N 0.000 description 2
- BNUSKMGXRXIWAF-UHFFFAOYSA-N 3-chloro-1,1,1,3-tetrafluorobutane Chemical compound CC(F)(Cl)CC(F)(F)F BNUSKMGXRXIWAF-UHFFFAOYSA-N 0.000 description 2
- 241000183024 Populus tremula Species 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical class ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 235000003270 potassium fluoride Nutrition 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 description 1
- NVSXSBBVEDNGPY-UHFFFAOYSA-N 1,1,1,2,2-pentafluorobutane Chemical compound CCC(F)(F)C(F)(F)F NVSXSBBVEDNGPY-UHFFFAOYSA-N 0.000 description 1
- HCCXTSAGOJXOJG-UHFFFAOYSA-N 1,1,1,3-tetrachloro-3-fluorobutane Chemical compound CC(F)(Cl)CC(Cl)(Cl)Cl HCCXTSAGOJXOJG-UHFFFAOYSA-N 0.000 description 1
- MINPZZUPSSVGJN-UHFFFAOYSA-N 1,1,1,4,4,4-hexachlorobutane Chemical compound ClC(Cl)(Cl)CCC(Cl)(Cl)Cl MINPZZUPSSVGJN-UHFFFAOYSA-N 0.000 description 1
- IZPMJFLFAHTFRK-UHFFFAOYSA-N 1,1,1-trichloro-3,3-difluorobutane Chemical compound CC(F)(F)CC(Cl)(Cl)Cl IZPMJFLFAHTFRK-UHFFFAOYSA-N 0.000 description 1
- XHDSPHHDGAQIDF-UHFFFAOYSA-N 1,1,3,3-tetrachloro-1-fluorobutane Chemical compound CC(Cl)(Cl)CC(F)(Cl)Cl XHDSPHHDGAQIDF-UHFFFAOYSA-N 0.000 description 1
- XQVOZHXFNGMERA-UHFFFAOYSA-N 1,1,3-trichloro-1,3-difluorobutane Chemical compound CC(F)(Cl)CC(F)(Cl)Cl XQVOZHXFNGMERA-UHFFFAOYSA-N 0.000 description 1
- RMDJNEOJTZWCJE-UHFFFAOYSA-N 1,3,3-trichloro-1,1-difluorobutane Chemical compound CC(Cl)(Cl)CC(F)(F)Cl RMDJNEOJTZWCJE-UHFFFAOYSA-N 0.000 description 1
- BLEZTPDKUBSTII-UHFFFAOYSA-N 1-chloro-1-fluoroprop-1-ene Chemical class CC=C(F)Cl BLEZTPDKUBSTII-UHFFFAOYSA-N 0.000 description 1
- OUKWBMHBHGGKQE-UHFFFAOYSA-N 1-chloro-4,4,4-trifluorobut-1-ene Chemical class FC(F)(F)CC=CCl OUKWBMHBHGGKQE-UHFFFAOYSA-N 0.000 description 1
- DZDLBWDCTJUPKD-UHFFFAOYSA-N 3,3-dichloro-1,1-difluorobut-1-ene Chemical class CC(Cl)(Cl)C=C(F)F DZDLBWDCTJUPKD-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 150000001462 antimony Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 150000003608 titanium Chemical class 0.000 description 1
- 150000003609 titanium compounds Chemical group 0.000 description 1
- 238000005406 washing Methods 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
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B7/00—Halogens; Halogen acids
- C01B7/19—Fluorine; Hydrogen fluoride
- C01B7/191—Hydrogen fluoride
- C01B7/195—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B7/00—Halogens; Halogen acids
- C01B7/19—Fluorine; Hydrogen fluoride
- C01B7/191—Hydrogen fluoride
- C01B7/195—Separation; Purification
- C01B7/196—Separation; Purification by distillation
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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 |
|---|---|---|---|
| BE9800910 | 1998-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL208572B1 true PL208572B1 (pl) | 2011-05-31 |
Family
ID=3891577
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL385267A PL208572B1 (pl) | 1998-12-18 | 1999-12-16 | Sposób wytwarzania hydrofluoroalkanu, którym jest 1,1,1,3,3- pentafluorobutan |
| PL349391A PL200329B1 (pl) | 1998-12-18 | 1999-12-16 | Sposób rozdzielania mieszaniny zawierającej co najmniej jeden hydrofluoroalkan i fluorowodór oraz kompozycje azeotropowe lub pseudoazeotropowe |
| PL385268A PL206502B1 (pl) | 1998-12-18 | 1999-12-16 | Sposób wytwarzania 1, 1, 1, 3, 3-pentafluorobutanu |
| PL385266A PL208571B1 (pl) | 1998-12-18 | 1999-12-16 | Sposób wytwarzania 1,1,1,3,3- pentafluorobutanu |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL349391A PL200329B1 (pl) | 1998-12-18 | 1999-12-16 | Sposób rozdzielania mieszaniny zawierającej co najmniej jeden hydrofluoroalkan i fluorowodór oraz kompozycje azeotropowe lub pseudoazeotropowe |
| PL385268A PL206502B1 (pl) | 1998-12-18 | 1999-12-16 | Sposób wytwarzania 1, 1, 1, 3, 3-pentafluorobutanu |
| PL385266A PL208571B1 (pl) | 1998-12-18 | 1999-12-16 | Sposób wytwarzania 1,1,1,3,3- pentafluorobutanu |
Country Status (19)
| Country | Link |
|---|---|
| US (4) | US6521803B1 (https=) |
| EP (3) | EP1140747B1 (https=) |
| JP (2) | JP4785251B2 (https=) |
| KR (1) | KR100684939B1 (https=) |
| CN (5) | CN101284758B (https=) |
| AR (1) | AR021727A1 (https=) |
| AT (1) | ATE430119T1 (https=) |
| AU (1) | AU769820B2 (https=) |
| BR (1) | BR9916345B1 (https=) |
| CA (1) | CA2355385C (https=) |
| CZ (1) | CZ303077B6 (https=) |
| DE (1) | DE69940828D1 (https=) |
| ES (1) | ES2325778T3 (https=) |
| HU (1) | HU227729B1 (https=) |
| PL (4) | PL208572B1 (https=) |
| RU (2) | RU2392260C2 (https=) |
| TW (1) | TW499407B (https=) |
| WO (1) | WO2000037401A1 (https=) |
| ZA (1) | ZA200104829B (https=) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2355385C (fr) * | 1998-12-18 | 2010-04-27 | Solvay (Societe Anonyme) | Procede de separation d'un melange comprenant au moins un hydrofluoroalcane et du fluorure d'hydrogene, procedes de preparation d'un hydrofluoroalcane et compositions azeotropiques |
| WO2002098529A1 (en) | 2001-06-01 | 2002-12-12 | Honeywell International, Inc. | Azeotrope-like compositions of 1,1,1,3,3-pentafluorobutane and hydrogen fluoride |
| US7094936B1 (en) * | 2001-07-20 | 2006-08-22 | Great Lakes Chemical Corporation | Process for preparing halogenated alkanes |
| US20030028057A1 (en) * | 2001-07-20 | 2003-02-06 | Stephen Owens | Methods and materials for the preparation and purification of halogenated hydrocarbons |
| FR2855069B1 (fr) * | 2003-05-22 | 2006-06-16 | Solvay | Procede pour la separation d'au moins un compose organique |
| US6988994B2 (en) * | 2003-08-14 | 2006-01-24 | New York University | Positive airway pressure system and method for treatment of sleeping disorder in patient |
| US8101219B2 (en) * | 2004-03-05 | 2012-01-24 | Eggology, Inc. | Apparatus for preparing egg products in a microwave oven |
| US7709438B2 (en) * | 2005-11-01 | 2010-05-04 | E. I. Du Pont De Nemours And Company | Azeotrope compositions comprising nonafluoropentene and hydrogen fluoride and uses thereof |
| US8766020B2 (en) * | 2008-07-31 | 2014-07-01 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US20070106099A1 (en) * | 2005-11-10 | 2007-05-10 | Pcbu Services, Inc. | Production processes and systems |
| WO2008002500A1 (en) | 2006-06-27 | 2008-01-03 | E. I. Du Pont De Nemours And Company | Tetrafluoropropene production processes |
| US7803975B2 (en) * | 2006-07-13 | 2010-09-28 | E.I. Du Pont De Nemours And Company | Process for separating a fluoroolefin from HF by liquid-liquid extraction |
| US9040759B2 (en) * | 2007-07-06 | 2015-05-26 | Honeywell International Inc. | Preparation of fluorinated olefins via catalytic dehydrohalogenation of halogenated hydrocarbons |
| CN101952230B (zh) * | 2008-02-21 | 2015-07-22 | 纳幕尔杜邦公司 | 通过共沸蒸馏使2,3,3,3-四氟丙烯与氟化氢分离的方法 |
| WO2009105517A2 (en) * | 2008-02-21 | 2009-08-27 | E. I. Du Pont De Nemours And Company | Azeotrope compositions comprising 3,3,3-trifluoropropene and hydrogen fluoride and processes for separation thereof |
| KR102136117B1 (ko) * | 2008-02-21 | 2020-07-22 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | 공비 증류에 의한 플루오르화수소로부터의 1,3,3,3-테트라플루오로프로펜의 분리 방법 |
| US8410040B2 (en) * | 2008-10-31 | 2013-04-02 | Honeywell International Inc. | Azeotrope-like compositions of 1,1,1,2,3-pentachloropropane and hydrogen fluoride |
| US8008243B2 (en) * | 2008-10-31 | 2011-08-30 | Honeywell International Inc. | Azeotrope-like compositions of 1,1,2,3-tetrachloropropene and hydrogen fluoride |
| CN102227395A (zh) * | 2008-11-13 | 2011-10-26 | 苏威氟有限公司 | 氢氟烯烃、氢氟烯烃的制造以及使用氢氟烯烃的方法 |
| WO2010060868A1 (en) * | 2008-11-25 | 2010-06-03 | Solvay Fluor Gmbh | Process for the preparation of chlorofluoroalkenes |
| US8093441B2 (en) * | 2008-12-18 | 2012-01-10 | Exxonmobil Research And Engineering Company | Removal of light fluoroalkanes from hydrocarbon streams |
| US8075797B2 (en) * | 2009-01-29 | 2011-12-13 | Honeywell International Inc. | Azeotrope-like compositions of pentafluoropropane, chlorotrifluoropropene, and hydrogen fluoride |
| TW201103972A (en) | 2009-04-01 | 2011-02-01 | Solvay Fluor Gmbh | Process for the manufacture of etched items |
| EP2552877B1 (en) | 2010-04-02 | 2014-11-26 | Solvay Sa | Process for dehydrochlorination of hydrochlorofluoroalkanes |
| US8921622B2 (en) | 2010-04-02 | 2014-12-30 | Solvay Sa | Process for dehydrofluorinating hydrochlorofluoroalkanes and products obtained thereby |
| US8487155B2 (en) | 2010-12-07 | 2013-07-16 | Exxonmobil Research And Engineering Company | Removal of light fluoroalkanes from hydrocarbon streams |
| US8999909B2 (en) | 2012-02-23 | 2015-04-07 | Honeywell International Inc. | Azeotropic compositions of 1,1,1,3,3-pentachloropropane and hydrogen fluoride |
| CN111094503B (zh) * | 2017-09-11 | 2022-04-01 | 科慕埃弗西有限公司 | 包含氟化氢和含氟烃的共沸组合物 |
| CN110092707B (zh) * | 2018-01-30 | 2020-08-11 | 中昊晨光化工研究院有限公司 | 一种四氟乙烯生产过程中去除氟化氢的方法 |
| CN113939492B (zh) * | 2019-04-05 | 2024-05-17 | 科慕埃弗西有限公司 | 用于制备z-1,1,1,4,4,4-六氟丁-2-烯的方法以及用于制备其的中间体 |
| JP6958596B2 (ja) * | 2019-07-01 | 2021-11-02 | ダイキン工業株式会社 | アルカンの製造方法 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1443616C3 (de) * | 1963-11-13 | 1974-05-09 | Chemische Fabrik Von Heyden Gmbh, 8000 Muenchen | Verbessertes Verfahren zur Fluorierung und Polyfluorierung von Chlor enthaltenden niederen aliphatischen Halogenkohlenwasserstoffen |
| AU6647690A (en) | 1989-10-04 | 1991-04-28 | E.I. Du Pont De Nemours And Company | Fluorocarbon purification process |
| GB9007029D0 (en) * | 1990-03-29 | 1990-05-30 | Ici Plc | Chemical process |
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