BRPI0507454B1 - Purificação de 1,1,1,3,3,3-hexafluoroisopropanol - Google Patents
Purificação de 1,1,1,3,3,3-hexafluoroisopropanol Download PDFInfo
- Publication number
- BRPI0507454B1 BRPI0507454B1 BRPI0507454-1A BRPI0507454A BRPI0507454B1 BR PI0507454 B1 BRPI0507454 B1 BR PI0507454B1 BR PI0507454 A BRPI0507454 A BR PI0507454A BR PI0507454 B1 BRPI0507454 B1 BR PI0507454B1
- Authority
- BR
- Brazil
- Prior art keywords
- mixture
- trifluoroacetone
- hexafluoroisopropanol
- fractional distillation
- subjecting
- Prior art date
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 40
- 238000000746 purification Methods 0.000 title claims description 31
- 239000000203 mixture Substances 0.000 claims abstract description 85
- 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
- 239000007788 liquid Substances 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000001816 cooling Methods 0.000 claims abstract description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 51
- 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
- 239000003054 catalyst Substances 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 37
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 36
- 238000005984 hydrogenation reaction Methods 0.000 claims description 22
- 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
- 238000001914 filtration Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 235000003270 potassium fluoride Nutrition 0.000 claims description 3
- 239000011698 potassium fluoride Substances 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims 1
- 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 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 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
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 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
- 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 (2)
| Publication Number | Publication Date |
|---|---|
| BRPI0507454A BRPI0507454A (pt) | 2007-07-10 |
| BRPI0507454B1 true BRPI0507454B1 (pt) | 2014-07-29 |
Family
ID=34860222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0507454-1A BRPI0507454B1 (pt) | 2004-02-04 | 2005-02-04 | Purificação de 1,1,1,3,3,3-hexafluoroisopropanol |
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 |
| 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 |
| JP5048342B2 (ja) | 2012-10-17 |
| EP2275396B1 (en) | 2013-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 04/02/2005, OBSERVADAS AS CONDICOES LEGAIS. |
|
| B21F | Lapse acc. art. 78, item iv - on non-payment of the annual fees in time |
Free format text: REFERENTE A 12A ANUIDADE. |
|
| B24J | Lapse because of non-payment of annual fees (definitively: art 78 iv lpi, resolution 113/2013 art. 12) |