CN102516017B - 包含十氟戊烷和氟化氢的共沸物组合物和近共沸物组合物及其用途 - Google Patents
包含十氟戊烷和氟化氢的共沸物组合物和近共沸物组合物及其用途 Download PDFInfo
- Publication number
- CN102516017B CN102516017B CN201110309787.6A CN201110309787A CN102516017B CN 102516017 B CN102516017 B CN 102516017B CN 201110309787 A CN201110309787 A CN 201110309787A CN 102516017 B CN102516017 B CN 102516017B
- Authority
- CN
- China
- Prior art keywords
- hfc
- 10mee
- composition
- mole
- azeotrope
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 327
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 title claims abstract description 189
- 229910000040 hydrogen fluoride Inorganic materials 0.000 title claims abstract description 179
- RIQRGMUSBYGDBL-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,5-decafluoropentane Chemical compound FC(F)(F)C(F)C(F)C(F)(F)C(F)(F)F RIQRGMUSBYGDBL-UHFFFAOYSA-N 0.000 claims abstract description 153
- 238000000034 method Methods 0.000 claims description 77
- 230000008569 process Effects 0.000 claims description 18
- 230000005587 bubbling Effects 0.000 claims description 14
- 238000000926 separation method Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 239000000047 product Substances 0.000 description 78
- 238000004821 distillation Methods 0.000 description 69
- 238000004364 calculation method Methods 0.000 description 24
- 238000009835 boiling Methods 0.000 description 23
- 238000010992 reflux Methods 0.000 description 18
- 239000007788 liquid Substances 0.000 description 15
- 238000005259 measurement Methods 0.000 description 15
- 238000005796 dehydrofluorination reaction Methods 0.000 description 13
- 239000000463 material Substances 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- 238000009833 condensation Methods 0.000 description 10
- 230000005494 condensation Effects 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 230000008859 change Effects 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000003575 carbonaceous material Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000005057 refrigeration Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- KLZDCUBZWUSEGO-UHFFFAOYSA-N CC.F.F.F.F.F Chemical compound CC.F.F.F.F.F KLZDCUBZWUSEGO-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- -1 HF hydrocarbon Chemical class 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910001566 austenite Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- YOCUPQPZWBBYIX-UHFFFAOYSA-N copper nickel Chemical compound [Ni].[Cu] YOCUPQPZWBBYIX-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910000623 nickel–chromium alloy Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002699 waste material 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
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- 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
-
- 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
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
-
- 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
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
- C07C17/386—Separation; Purification; Stabilisation; Use of additives by distillation with auxiliary compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5036—Azeotropic mixtures containing halogenated solvents
- C11D7/504—Azeotropic mixtures containing halogenated solvents all solvents being halogenated hydrocarbons
- C11D7/505—Mixtures of (hydro)fluorocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73232005P | 2005-11-01 | 2005-11-01 | |
| US60/732320 | 2005-11-01 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2006800492777A Division CN101346330B (zh) | 2005-11-01 | 2006-11-01 | 包含九氟戊烯和氟化氢的共沸物组合物及其用途 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102516017A CN102516017A (zh) | 2012-06-27 |
| CN102516017B true CN102516017B (zh) | 2014-12-24 |
Family
ID=37909705
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2006800492777A Expired - Fee Related CN101346330B (zh) | 2005-11-01 | 2006-11-01 | 包含九氟戊烯和氟化氢的共沸物组合物及其用途 |
| CN201110309787.6A Expired - Fee Related CN102516017B (zh) | 2005-11-01 | 2006-11-01 | 包含十氟戊烷和氟化氢的共沸物组合物和近共沸物组合物及其用途 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2006800492777A Expired - Fee Related CN101346330B (zh) | 2005-11-01 | 2006-11-01 | 包含九氟戊烯和氟化氢的共沸物组合物及其用途 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7709438B2 (enExample) |
| JP (1) | JP2009513817A (enExample) |
| KR (1) | KR101497709B1 (enExample) |
| CN (2) | CN101346330B (enExample) |
| MY (1) | MY145650A (enExample) |
| WO (1) | WO2007053738A2 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US7388117B2 (en) * | 2005-11-01 | 2008-06-17 | E.I. Du Pont De Nemours And Company | Azeotrope compositions comprising 1,2,3,3,3-pentafluoropropene and hydrogen fluoride and uses thereof |
| RU2466979C2 (ru) | 2006-08-24 | 2012-11-20 | Е.И.Дюпон Де Немур Энд Компани | Способ отделения фторолефинов от фтороводорода путем азеотропной дистилляции |
| EP3147274B1 (en) | 2008-02-21 | 2018-09-05 | The Chemours Company FC, LLC | Processes for separation of 3,3,3-trifluoropropene and hydrogen fluoride |
| MX2010009081A (es) | 2008-02-21 | 2010-09-07 | Du Pont | Procesos para separar 1,3,3,3-tetrafluoropropeno de fluoruro de hidrogeno mediante destilacion azeotropica. |
| US20110144395A1 (en) * | 2008-08-29 | 2011-06-16 | E.I. Du Pont De Nemours And Company | Process to remove hf from 1,1,1,2,2,3,4,5,5,5-decafluoropentane |
| WO2010092085A1 (en) * | 2009-02-11 | 2010-08-19 | Arkema France | Azeotrope and azeotrope-like compositions of chlorotrifluoropropene and pentane |
| US8747691B2 (en) * | 2010-05-06 | 2014-06-10 | Honeywell International Inc. | Azeotrope-like compositions of tetrafluoropropene and water |
| US8951431B2 (en) * | 2010-05-06 | 2015-02-10 | E I Du Pont De Nemours And Company | Azeotrope-like compositions of pentafluoropropene and water |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1196716A (zh) * | 1995-08-01 | 1998-10-21 | 纳幕尔杜邦公司 | 制备卤化碳的方法和制得的化合物及其与氟化氢的恒沸物 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1706690A1 (ru) * | 1988-04-19 | 1992-01-23 | Всесоюзный Научно-Исследовательский Институт Технического Углерода | Пористый углеродный материал |
| US5171902A (en) * | 1990-10-11 | 1992-12-15 | E. I. Du Pont De Nemours And Company | Saturated linear polyfluorohydrocarbons, processes for their production, and their use in cleaning compositions |
| US5268122A (en) * | 1991-08-28 | 1993-12-07 | E. I. Du Pont De Nemours And Company | Gem-dihydropolyfluoroalkanes and monohydropolyfluoroalkenes, processes for their production, and use of gem-dihydropolyfluoroalkanes in cleaning compositions |
| US6755942B1 (en) * | 1995-08-01 | 2004-06-29 | E. I. Du Pont De Nemours And Company | Process for the manufacture of halocarbons and selected compounds and azeotropes with HF |
| JP3514041B2 (ja) * | 1996-06-27 | 2004-03-31 | ダイキン工業株式会社 | １，１，１，３，３−ペンタフルオロプロパンの精製方法 |
| FR2768717B1 (fr) * | 1997-09-24 | 1999-11-12 | Solvay | Procede de separation de fluorure d'hydrogene de ses melanges avec un hydrofluoroalcane contenant de 3 a 6 atomes de carbone |
| US5918481A (en) * | 1997-11-20 | 1999-07-06 | Alliedsignal Inc. | Process for separating hydrogen fluoride from fluorocarbons |
| WO1999026907A1 (en) * | 1997-11-25 | 1999-06-03 | Imperial Chemical Industries Plc | Preparation of fluorine-containing organic compounds |
| HU227729B1 (en) * | 1998-12-18 | 2012-01-30 | Solvay | Method for separating a mixture comprising at least an hydrofluoroalkane and hydrogen fluoride, methods for preparing a hydrofluoroalkane and azeotropic compositions |
| JP4085520B2 (ja) * | 1999-06-16 | 2008-05-14 | 三菱マテリアル株式会社 | 劣化ｕｆ６の処理設備及びその処理方法 |
| US20050080303A1 (en) * | 2003-10-08 | 2005-04-14 | Akira Sekiya | Porous calcium fluoride, its producing method, catalyst for hydrogenation reaction, and method for producing trihydrofluorocarbon |
| 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 |
-
2006
- 2006-10-31 US US11/590,457 patent/US7709438B2/en not_active Expired - Fee Related
- 2006-11-01 MY MYPI20081388A patent/MY145650A/en unknown
- 2006-11-01 WO PCT/US2006/042773 patent/WO2007053738A2/en not_active Ceased
- 2006-11-01 KR KR1020087013107A patent/KR101497709B1/ko not_active Expired - Fee Related
- 2006-11-01 CN CN2006800492777A patent/CN101346330B/zh not_active Expired - Fee Related
- 2006-11-01 CN CN201110309787.6A patent/CN102516017B/zh not_active Expired - Fee Related
- 2006-11-01 JP JP2008539019A patent/JP2009513817A/ja active Pending
-
2010
- 2010-04-26 US US12/714,674 patent/US20100203167A1/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1196716A (zh) * | 1995-08-01 | 1998-10-21 | 纳幕尔杜邦公司 | 制备卤化碳的方法和制得的化合物及其与氟化氢的恒沸物 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101346330B (zh) | 2013-03-27 |
| KR101497709B1 (ko) | 2015-03-02 |
| CN102516017A (zh) | 2012-06-27 |
| WO2007053738A3 (en) | 2007-09-20 |
| WO2007053738A2 (en) | 2007-05-10 |
| KR20080066838A (ko) | 2008-07-16 |
| US20100203167A1 (en) | 2010-08-12 |
| US20070099811A1 (en) | 2007-05-03 |
| CN101346330A (zh) | 2009-01-14 |
| MY145650A (en) | 2012-03-15 |
| JP2009513817A (ja) | 2009-04-02 |
| US7709438B2 (en) | 2010-05-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102603462B (zh) | 包含2,3,3,3-四氟丙烯和氟化氢的共沸物组合物及其用途 | |
| JP5567627B2 (ja) | １，１，１，２，３−ペンタフルオロプロペンおよびフッ化水素を含む共沸組成物およびその使用 | |
| US7423188B2 (en) | Azeotrope compositions comprising E-1,3,3,3-tetrafluoropropene and hydrogen fluoride and uses thereof | |
| EP2382300B1 (en) | Azeotrope-like compositions of pentafluoropropane, chlorotrifluoropropene, and hydrogen fluoride | |
| US20100203167A1 (en) | Azeotrope compositions comprising decafluoropentane and hydrogen fluoride and uses thereof | |
| CN102408302B (zh) | 包含十三氟-3-庚烯和氟化氢的共沸物组合物及其用途 | |
| CN111094503B (zh) | 包含氟化氢和含氟烃的共沸组合物 | |
| HK1169097A (en) | Azeotrope compositions comprising tridecafluoro-3-heptene and hydrogen fluoride and uses thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20171221 Address after: Delaware, USA Patentee after: Como Efsee Co.,Ltd. Address before: Wilmington, Delaware, USA Patentee before: E. I. du Pont de Nemours and Co. |
|
| TR01 | Transfer of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20141224 Termination date: 20201101 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |