CN102408302B - 包含十三氟-3-庚烯和氟化氢的共沸物组合物及其用途 - Google Patents
包含十三氟-3-庚烯和氟化氢的共沸物组合物及其用途 Download PDFInfo
- Publication number
- CN102408302B CN102408302B CN201110278129.5A CN201110278129A CN102408302B CN 102408302 B CN102408302 B CN 102408302B CN 201110278129 A CN201110278129 A CN 201110278129A CN 102408302 B CN102408302 B CN 102408302B
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- China
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- 239000000203 mixture Substances 0.000 title claims abstract description 383
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical group F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 179
- 238000000034 method Methods 0.000 claims abstract description 77
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 168
- 239000000047 product Substances 0.000 claims description 95
- 238000005796 dehydrofluorination reaction Methods 0.000 claims description 13
- 230000005587 bubbling Effects 0.000 claims description 12
- 238000000926 separation method Methods 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 abstract description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract description 10
- IMFRQXJTPNCKAO-UHFFFAOYSA-N 1,1,1,2,2,3,5,5,6,6,7,7,7-tridecafluorohept-3-ene Chemical compound FC(F)(F)C(F)(F)C(F)=CC(F)(F)C(F)(F)C(F)(F)F IMFRQXJTPNCKAO-UHFFFAOYSA-N 0.000 abstract description 3
- HTKQZWCWSRBOKO-UHFFFAOYSA-N 1,1,1,2,2,4,5,5,6,6,7,7,7-tridecafluorohept-3-ene Chemical compound FC(F)(F)C(F)(F)C=C(F)C(F)(F)C(F)(F)C(F)(F)F HTKQZWCWSRBOKO-UHFFFAOYSA-N 0.000 abstract description 3
- 238000004821 distillation Methods 0.000 description 59
- 238000009835 boiling Methods 0.000 description 26
- 238000010992 reflux Methods 0.000 description 19
- 239000007788 liquid Substances 0.000 description 13
- 239000000463 material Substances 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- 238000009833 condensation Methods 0.000 description 10
- 230000005494 condensation Effects 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 7
- 230000008859 change Effects 0.000 description 6
- 239000012071 phase Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000007789 gas Substances 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
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 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
- 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
- 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
- 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
- 238000010521 absorption reaction Methods 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
- 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
- 239000003054 catalyst Substances 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
- 238000013461 design Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73208805P | 2005-11-01 | 2005-11-01 | |
| US60/732088 | 2005-11-01 | ||
| CN200680049484.2A CN101351431B (zh) | 2005-11-01 | 2006-11-01 | 包含十三氟-3-庚烯和氟化氢的共沸物组合物及其用途 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200680049484.2A Division CN101351431B (zh) | 2005-11-01 | 2006-11-01 | 包含十三氟-3-庚烯和氟化氢的共沸物组合物及其用途 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102408302A CN102408302A (zh) | 2012-04-11 |
| CN102408302B true CN102408302B (zh) | 2015-11-25 |
Family
ID=37907833
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110278129.5A Expired - Fee Related CN102408302B (zh) | 2005-11-01 | 2006-11-01 | 包含十三氟-3-庚烯和氟化氢的共沸物组合物及其用途 |
| CN200680049484.2A Expired - Fee Related CN101351431B (zh) | 2005-11-01 | 2006-11-01 | 包含十三氟-3-庚烯和氟化氢的共沸物组合物及其用途 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200680049484.2A Expired - Fee Related CN101351431B (zh) | 2005-11-01 | 2006-11-01 | 包含十三氟-3-庚烯和氟化氢的共沸物组合物及其用途 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7385094B2 (enExample) |
| EP (1) | EP1948581A2 (enExample) |
| JP (1) | JP2009513816A (enExample) |
| CN (2) | CN102408302B (enExample) |
| WO (1) | WO2007053735A2 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7897823B2 (en) * | 2004-10-29 | 2011-03-01 | E. I. Du Pont De Nemours And Company | Process for production of azeotrope compositions comprising hydrofluoroolefin and hydrogen fluoride and uses of said azeotrope compositions in separation processes |
| MY145459A (en) * | 2005-11-01 | 2012-02-15 | Du Pont | Solvent compositions comprising unsaturated fluorinated hydrocarbons |
| CN101541715B (zh) | 2006-08-24 | 2013-09-11 | 纳幕尔杜邦公司 | 通过共沸蒸馏将氟代烯烃与氟化氢分离的方法 |
| RU2474569C2 (ru) | 2008-02-21 | 2013-02-10 | Е.И.Дюпон Де Немур Энд Компани | Способ отделения 1,3,3,3-тетрафторпропена от фтороводорода азеотропной дистилляцией |
| KR102035526B1 (ko) | 2008-02-21 | 2019-10-24 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | 3,3,3-트라이플루오로프로펜 및 플루오르화수소를 포함하는 공비 조성물 및 이의 분리방법 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5458674A (en) * | 1993-08-24 | 1995-10-17 | E. I. Du Pont De Nemours And Company | Organic separation from HF |
| US5918481A (en) * | 1997-11-20 | 1999-07-06 | Alliedsignal Inc. | Process for separating hydrogen fluoride from fluorocarbons |
| CN1284053A (zh) * | 1997-11-25 | 2001-02-14 | 帝国化学工业公司 | 含氟有机化合物的制备 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US7476331B2 (en) | 2005-02-09 | 2009-01-13 | E I Du Pont Nemours And Company | Compositions comprising 1,1,1,2,2,3,4,5,5,6,6,7,7,7-tetradecafluoroheptane and uses thereof |
| MY145459A (en) * | 2005-11-01 | 2012-02-15 | Du Pont | Solvent compositions comprising unsaturated fluorinated hydrocarbons |
-
2006
- 2006-10-31 US US11/590,455 patent/US7385094B2/en active Active
- 2006-11-01 EP EP06836795A patent/EP1948581A2/en not_active Withdrawn
- 2006-11-01 JP JP2008539016A patent/JP2009513816A/ja not_active Ceased
- 2006-11-01 WO PCT/US2006/042770 patent/WO2007053735A2/en not_active Ceased
- 2006-11-01 CN CN201110278129.5A patent/CN102408302B/zh not_active Expired - Fee Related
- 2006-11-01 CN CN200680049484.2A patent/CN101351431B/zh not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5458674A (en) * | 1993-08-24 | 1995-10-17 | E. I. Du Pont De Nemours And Company | Organic separation from HF |
| US5918481A (en) * | 1997-11-20 | 1999-07-06 | Alliedsignal Inc. | Process for separating hydrogen fluoride from fluorocarbons |
| CN1284053A (zh) * | 1997-11-25 | 2001-02-14 | 帝国化学工业公司 | 含氟有机化合物的制备 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102408302A (zh) | 2012-04-11 |
| JP2009513816A (ja) | 2009-04-02 |
| CN101351431B (zh) | 2013-01-02 |
| WO2007053735A3 (en) | 2007-07-26 |
| CN101351431A (zh) | 2009-01-21 |
| US20070100176A1 (en) | 2007-05-03 |
| EP1948581A2 (en) | 2008-07-30 |
| WO2007053735A2 (en) | 2007-05-10 |
| US7385094B2 (en) | 2008-06-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: DE Ref document number: 1169097 Country of ref document: HK |
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| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20180104 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. |
|
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20151125 Termination date: 20201101 |