JP5048342B2 - １，１，１，３，３，３−ヘキサフルオロイソプロパノールの精製 - Google Patents
１，１，１，３，３，３−ヘキサフルオロイソプロパノールの精製 Download PDFInfo
- Publication number
- JP5048342B2 JP5048342B2 JP2006552229A JP2006552229A JP5048342B2 JP 5048342 B2 JP5048342 B2 JP 5048342B2 JP 2006552229 A JP2006552229 A JP 2006552229A JP 2006552229 A JP2006552229 A JP 2006552229A JP 5048342 B2 JP5048342 B2 JP 5048342B2
- Authority
- JP
- Japan
- Prior art keywords
- trifluoroacetone
- hexafluoroisopropanol
- mixture
- product mixture
- fractional distillation
- 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 37
- 238000000746 purification Methods 0.000 title claims description 33
- 239000000203 mixture Substances 0.000 claims abstract description 79
- 238000004508 fractional distillation Methods 0.000 claims abstract description 33
- 238000009835 boiling Methods 0.000 claims abstract description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 10
- 238000001816 cooling Methods 0.000 claims abstract description 8
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 54
- 239000003054 catalyst Substances 0.000 claims description 47
- FHUDAMLDXFJHJE-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-one Chemical compound CC(=O)C(F)(F)F FHUDAMLDXFJHJE-UHFFFAOYSA-N 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 42
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 34
- 238000005984 hydrogenation reaction Methods 0.000 claims description 29
- 229910052763 palladium Inorganic materials 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 claims description 3
- 235000003270 potassium fluoride Nutrition 0.000 claims description 3
- 239000011698 potassium fluoride Substances 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 238000010531 catalytic reduction reaction Methods 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 27
- QPJSUIGXIBEQAC-UHFFFAOYSA-N n-(2,4-dichloro-5-propan-2-yloxyphenyl)acetamide Chemical group CC(C)OC1=CC(NC(C)=O)=C(Cl)C=C1Cl QPJSUIGXIBEQAC-UHFFFAOYSA-N 0.000 description 13
- 238000006722 reduction reaction Methods 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 238000013459 approach Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010626 work up procedure Methods 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
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54181804P | 2004-02-04 | 2004-02-04 | |
| US60/541,818 | 2004-02-04 | ||
| PCT/US2005/003366 WO2005077873A1 (en) | 2004-02-04 | 2005-02-04 | Purification of 1,1,1,3,3,3-hexafluoroisopropanol |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007520561A JP2007520561A (ja) | 2007-07-26 |
| JP2007520561A5 JP2007520561A5 (enExample) | 2008-03-13 |
| JP5048342B2 true JP5048342B2 (ja) | 2012-10-17 |
Family
ID=34860222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006552229A Expired - Fee Related JP5048342B2 (ja) | 2004-02-04 | 2005-02-04 | １，１，１，３，３，３−ヘキサフルオロイソプロパノールの精製 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7659433B2 (enExample) |
| EP (2) | EP1711449B1 (enExample) |
| JP (1) | JP5048342B2 (enExample) |
| KR (1) | KR101321760B1 (enExample) |
| CN (1) | CN1934060B (enExample) |
| AT (1) | ATE486833T1 (enExample) |
| BR (1) | BRPI0507454B1 (enExample) |
| CA (1) | CA2555653C (enExample) |
| DE (1) | DE602005024516D1 (enExample) |
| ES (1) | ES2353389T3 (enExample) |
| WO (1) | WO2005077873A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5157478B2 (ja) * | 2008-01-25 | 2013-03-06 | ダイキン工業株式会社 | オレフィン−アルコール共沸混合物の分離方法 |
| US7524995B1 (en) | 2008-06-12 | 2009-04-28 | E.I. Du Pont De Nemours And Company | Continuous process to produce hexafluoroisopropanol |
| BR112013021431A2 (pt) * | 2011-02-16 | 2016-10-25 | Halocarbon Prod Corp | processo para a preparação de dióis fluorados |
| 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 |
| CN111205166B (zh) * | 2019-12-30 | 2022-04-22 | 天津市长芦化工新材料有限公司 | 气相加氢制备六氟异丙醇的方法 |
| WO2021187369A1 (ja) * | 2020-03-19 | 2021-09-23 | セントラル硝子株式会社 | （ハイドロ）ハロカーボンの製造方法 |
| CN117123214A (zh) * | 2022-05-20 | 2023-11-28 | 浙江蓝天环保高科技股份有限公司 | 一种用于制备六氟异丙醇的催化剂、其制备方法及应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES289529A1 (es) * | 1962-07-03 | 1963-11-01 | Allied Chem | Procedimiento de obtencion de alcohol hexafluoroisopropilico |
| US3702872A (en) | 1970-07-27 | 1972-11-14 | Baxter Laboratories Inc | Production of hexafluoropropanol |
| US4314087A (en) * | 1979-12-26 | 1982-02-02 | Baxter Travenol Laboratories, Inc. | Methods of synthesizing hexafluoroisopropanol from impure mixtures and synthesis of a fluoromethyl ether therefrom |
| JPH06184026A (ja) * | 1992-12-21 | 1994-07-05 | Central Glass Co Ltd | １，１，１，３，３，３−ヘキサフルオロプロパン−２−オ−ルの精製方法 |
| JP2002069020A (ja) * | 2000-08-24 | 2002-03-08 | Asahi Glass Co Ltd | フッ化アルコールの製造方法 |
-
2005
- 2005-02-04 US US10/599,472 patent/US7659433B2/en not_active Expired - Fee Related
- 2005-02-04 ES ES05706171T patent/ES2353389T3/es not_active Expired - Lifetime
- 2005-02-04 KR KR1020067017438A patent/KR101321760B1/ko not_active Expired - Fee Related
- 2005-02-04 CA CA2555653A patent/CA2555653C/en not_active Expired - Fee Related
- 2005-02-04 JP JP2006552229A patent/JP5048342B2/ja not_active Expired - Fee Related
- 2005-02-04 EP EP05706171A patent/EP1711449B1/en not_active Expired - Lifetime
- 2005-02-04 AT AT05706171T patent/ATE486833T1/de not_active IP Right Cessation
- 2005-02-04 WO PCT/US2005/003366 patent/WO2005077873A1/en not_active Ceased
- 2005-02-04 BR BRPI0507454-1A patent/BRPI0507454B1/pt not_active IP Right Cessation
- 2005-02-04 CN CN2005800086745A patent/CN1934060B/zh not_active Expired - Fee Related
- 2005-02-04 EP EP10189687.6A patent/EP2275396B1/en not_active Expired - Lifetime
- 2005-02-04 DE DE602005024516T patent/DE602005024516D1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US20080058560A1 (en) | 2008-03-06 |
| BRPI0507454A (pt) | 2007-07-10 |
| EP1711449A4 (en) | 2008-02-20 |
| EP1711449B1 (en) | 2010-11-03 |
| EP2275396A3 (en) | 2011-03-02 |
| BRPI0507454B1 (pt) | 2014-07-29 |
| CA2555653A1 (en) | 2005-08-25 |
| KR101321760B1 (ko) | 2013-10-25 |
| ATE486833T1 (de) | 2010-11-15 |
| US7659433B2 (en) | 2010-02-09 |
| CA2555653C (en) | 2012-08-28 |
| KR20070001980A (ko) | 2007-01-04 |
| EP1711449A1 (en) | 2006-10-18 |
| EP2275396A2 (en) | 2011-01-19 |
| JP2007520561A (ja) | 2007-07-26 |
| WO2005077873A1 (en) | 2005-08-25 |
| CN1934060A (zh) | 2007-03-21 |
| CN1934060B (zh) | 2010-09-01 |
| DE602005024516D1 (de) | 2010-12-16 |
| ES2353389T3 (es) | 2011-03-01 |
| EP2275396B1 (en) | 2013-07-31 |
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