CN102056879B - 制备六氟异丙醇的连续方法 - Google Patents
制备六氟异丙醇的连续方法 Download PDFInfo
- Publication number
- CN102056879B CN102056879B CN200980121726.8A CN200980121726A CN102056879B CN 102056879 B CN102056879 B CN 102056879B CN 200980121726 A CN200980121726 A CN 200980121726A CN 102056879 B CN102056879 B CN 102056879B
- Authority
- CN
- China
- Prior art keywords
- reactor
- hexafluoroisopropanol
- hydrogen
- catalyzer
- hfip
- 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.)
- Expired - Fee Related
Links
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 title claims abstract description 106
- 238000010924 continuous production Methods 0.000 title abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract description 69
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 69
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 63
- 239000003054 catalyst Substances 0.000 claims abstract description 58
- 239000007788 liquid Substances 0.000 claims abstract description 47
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 39
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims description 75
- 238000002156 mixing Methods 0.000 claims description 55
- 229910052751 metal Inorganic materials 0.000 claims description 36
- 239000002184 metal Substances 0.000 claims description 36
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 25
- 230000003197 catalytic effect Effects 0.000 claims description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 18
- 229910052759 nickel Inorganic materials 0.000 claims description 12
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical group O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 11
- 238000000926 separation method Methods 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- 238000011084 recovery Methods 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 235000012239 silicon dioxide Nutrition 0.000 claims description 6
- 229960001866 silicon dioxide Drugs 0.000 claims description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 4
- 239000010941 cobalt Substances 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 239000010439 graphite Substances 0.000 claims description 3
- 229910002804 graphite Inorganic materials 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 239000010937 tungsten Substances 0.000 claims description 2
- 238000012423 maintenance Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 70
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000007789 gas Substances 0.000 description 17
- 238000010438 heat treatment Methods 0.000 description 15
- 239000003507 refrigerant Substances 0.000 description 13
- 238000001816 cooling Methods 0.000 description 11
- 239000008187 granular material Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 239000012530 fluid Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229910044991 metal oxide Inorganic materials 0.000 description 6
- 150000004706 metal oxides Chemical class 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- 230000009466 transformation Effects 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000012263 liquid product Substances 0.000 description 4
- 238000013459 approach Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000001351 cycling effect Effects 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- -1 1,1,1,3,3,3-hexafluoro-2-propyl Chemical group 0.000 description 2
- 229910000619 316 stainless steel Inorganic materials 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- 239000010963 304 stainless steel Substances 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229910000589 SAE 304 stainless steel Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- PZZYQPZGQPZBDN-UHFFFAOYSA-N aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- PHTHEUNUXVDUOD-UHFFFAOYSA-N aluminum oxygen(2-) titanium(4+) Chemical compound [O-2].[O-2].[Ti+4].[O-2].[Al+3] PHTHEUNUXVDUOD-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000005243 fluidization Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000002071 nanotube Substances 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000009418 renovation Methods 0.000 description 1
- 230000001020 rhythmical effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000011555 saturated liquid Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000005496 tempering Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
- C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/138,002 US7524995B1 (en) | 2008-06-12 | 2008-06-12 | Continuous process to produce hexafluoroisopropanol |
| PCT/US2009/046078 WO2009152006A2 (en) | 2008-06-12 | 2009-06-24 | Continuous process to produce hexafluoroisopropanol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102056879A CN102056879A (zh) | 2011-05-11 |
| CN102056879B true CN102056879B (zh) | 2014-11-05 |
Family
ID=40568899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200980121726.8A Expired - Fee Related CN102056879B (zh) | 2008-06-12 | 2009-06-24 | 制备六氟异丙醇的连续方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7524995B1 (enExample) |
| EP (1) | EP2398754B1 (enExample) |
| JP (1) | JP5400148B2 (enExample) |
| CN (1) | CN102056879B (enExample) |
| WO (1) | WO2009152006A2 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102716761B (zh) * | 2012-07-03 | 2013-10-23 | 浙江师范大学 | 用于三水六氟丙酮气相加氢生产六氟异丙醇的催化剂 |
| CN106187691B (zh) * | 2015-05-05 | 2019-01-18 | 浙江蓝天环保高科技股份有限公司 | 一种从含六氟异丙醇和氢气的混合气中回收六氟异丙醇的方法 |
| JP2021066674A (ja) * | 2019-10-18 | 2021-04-30 | セントラル硝子株式会社 | ヘキサフルオロイソプロパノールの統合再利用システムおよびヘキサフルオロイソプロパノールの統合再利用方法 |
| CN111960429B (zh) * | 2020-08-26 | 2022-07-12 | 万华化学集团股份有限公司 | 一种多级孔磷酸铝分子筛催化剂的制备方法、由其制备的催化剂及其在烯烃异构中的应用 |
| CN119661320B (zh) * | 2025-02-19 | 2025-06-27 | 淄博飞源化工有限公司 | 六氟异丙醇的合成方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3607952A (en) * | 1969-03-28 | 1971-09-21 | Du Pont | Process for preparation of hexafluoroisopropanol |
| US5256163A (en) * | 1991-09-11 | 1993-10-26 | Philip Morris Incorporated | Flow liquid-phase chemical reaction process |
| US7041857B1 (en) * | 2005-09-07 | 2006-05-09 | Air Products And Chemicals, Inc. | Hydrogenation of acetone |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6036411B2 (ja) | 1980-04-03 | 1985-08-20 | セントラル硝子株式会社 | １，１，１，３，３，３−ヘキサフルオロ−プロパン−２−オ−ルの製造法 |
| JPS6054931B2 (ja) | 1981-11-24 | 1985-12-03 | 旭硝子株式会社 | １，１，１，３，３，３‐ヘキサフルオロ‐２‐プロパノールの製法 |
| JPS59204142A (ja) | 1983-04-28 | 1984-11-19 | Nippon Mektron Ltd | ヘキサフルオロイソプロピルアルコ−ルの製造法 |
| JPS6069047A (ja) * | 1983-09-27 | 1985-04-19 | Central Glass Co Ltd | １．１．１．３．３．３−ヘキサフルオロプロパン−２−オ−ルの製造法 |
| JPH01301631A (ja) | 1988-05-31 | 1989-12-05 | Central Glass Co Ltd | １，１，１，３，３，３−ヘキサフルオロプロパン−２−オールの製造法 |
| JP2834495B2 (ja) * | 1989-10-20 | 1998-12-09 | 三井化学株式会社 | イソプロパノールの製造方法及び装置 |
| JP2638727B2 (ja) | 1992-12-21 | 1997-08-06 | セントラル硝子株式会社 | １，１，１，３，３，３−ヘキサフルオロプロパン−２−オ−ルの製造法 |
| NL1004961C2 (nl) | 1997-01-09 | 1998-07-13 | Dsm Nv | Monolietreactor. |
| US7291257B2 (en) | 1997-06-24 | 2007-11-06 | Process Dynamics, Inc. | Two phase hydroprocessing |
| ES2227852T3 (es) | 1997-06-24 | 2005-04-01 | Process Dynamics, Inc. | Hidroprocesado en dos fases. |
| US6005143A (en) | 1998-08-07 | 1999-12-21 | Air Products And Chemicals, Inc. | Use of a monolith catalyst for the hydrogenation of dinitrotoluene to toluenediamine |
| EP1121976A1 (en) * | 2000-02-03 | 2001-08-08 | Engelhard Corporation | Chemical process in reactor with structured catalyst |
| US6506361B1 (en) | 2000-05-18 | 2003-01-14 | Air Products And Chemicals, Inc. | Gas-liquid reaction process including ejector and monolith catalyst |
| WO2002026679A1 (fr) | 2000-09-27 | 2002-04-04 | Asahi Glass Company, Limited | Procede de production d'alcool fluore |
| JP4288451B2 (ja) | 2001-03-23 | 2009-07-01 | ダイキン工業株式会社 | １，１，１，３，３，３−ヘキサフルオロプロパン−２−オールの製造方法 |
| US6479704B1 (en) | 2001-04-20 | 2002-11-12 | Air Products And Chemicals, Inc. | Hydrogenation with monolith reactor under conditions of immiscible liquid phases |
| JP5028731B2 (ja) | 2001-09-18 | 2012-09-19 | 旭硝子株式会社 | ハロゲン化アルコ−ルの製造方法 |
| BRPI0507454B1 (pt) | 2004-02-04 | 2014-07-29 | Halocarbon Prod Corp | Purificação de 1,1,1,3,3,3-hexafluoroisopropanol |
| CN100420661C (zh) | 2006-11-28 | 2008-09-24 | 上海三爱富新材料股份有限公司 | 1,1,1,3,3,3-六氟异丙醇的合成方法 |
-
2008
- 2008-06-12 US US12/138,002 patent/US7524995B1/en not_active Expired - Fee Related
-
2009
- 2009-06-24 JP JP2011513575A patent/JP5400148B2/ja not_active Expired - Fee Related
- 2009-06-24 CN CN200980121726.8A patent/CN102056879B/zh not_active Expired - Fee Related
- 2009-06-24 WO PCT/US2009/046078 patent/WO2009152006A2/en not_active Ceased
- 2009-06-24 EP EP09763297.0A patent/EP2398754B1/en not_active Not-in-force
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3607952A (en) * | 1969-03-28 | 1971-09-21 | Du Pont | Process for preparation of hexafluoroisopropanol |
| US5256163A (en) * | 1991-09-11 | 1993-10-26 | Philip Morris Incorporated | Flow liquid-phase chemical reaction process |
| US7041857B1 (en) * | 2005-09-07 | 2006-05-09 | Air Products And Chemicals, Inc. | Hydrogenation of acetone |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2398754B1 (en) | 2015-06-03 |
| JP2011523957A (ja) | 2011-08-25 |
| WO2009152006A8 (en) | 2011-08-11 |
| WO2009152006A3 (en) | 2010-03-04 |
| CN102056879A (zh) | 2011-05-11 |
| US7524995B1 (en) | 2009-04-28 |
| EP2398754A2 (en) | 2011-12-28 |
| WO2009152006A2 (en) | 2009-12-17 |
| JP5400148B2 (ja) | 2014-01-29 |
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