ES2383910T3 - Composiciones de azeótropos que comprenden 1,2,3,3,3-pentafluoropropeno y fluoruro de hidrógeno y su uso - Google Patents
Composiciones de azeótropos que comprenden 1,2,3,3,3-pentafluoropropeno y fluoruro de hidrógeno y su uso Download PDFInfo
- Publication number
- ES2383910T3 ES2383910T3 ES06827293T ES06827293T ES2383910T3 ES 2383910 T3 ES2383910 T3 ES 2383910T3 ES 06827293 T ES06827293 T ES 06827293T ES 06827293 T ES06827293 T ES 06827293T ES 2383910 T3 ES2383910 T3 ES 2383910T3
- Authority
- ES
- Spain
- Prior art keywords
- composition
- hfc
- mole percent
- pressure
- azeotropic
- 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.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 266
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 title claims abstract description 157
- 229910000040 hydrogen fluoride Inorganic materials 0.000 title claims abstract description 153
- DMUPYMORYHFFCT-UPHRSURJSA-N (z)-1,2,3,3,3-pentafluoroprop-1-ene Chemical compound F\C=C(/F)C(F)(F)F DMUPYMORYHFFCT-UPHRSURJSA-N 0.000 title claims abstract description 12
- 238000004821 distillation Methods 0.000 claims description 96
- 238000000034 method Methods 0.000 claims description 78
- 239000003292 glue Substances 0.000 claims description 50
- 239000000047 product Substances 0.000 claims description 25
- 238000000926 separation method Methods 0.000 claims description 21
- 238000005796 dehydrofluorination reaction Methods 0.000 claims description 15
- FYIRUPZTYPILDH-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoropropane Chemical compound FC(F)C(F)C(F)(F)F FYIRUPZTYPILDH-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 238000000746 purification Methods 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 238000004064 recycling Methods 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 238000009835 boiling Methods 0.000 description 25
- 238000010992 reflux Methods 0.000 description 16
- 238000010533 azeotropic distillation Methods 0.000 description 15
- 239000007788 liquid Substances 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 238000004364 calculation method Methods 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000004579 marble Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003575 carbonaceous material Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910000856 hastalloy Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NDMMKOCNFSTXRU-UHFFFAOYSA-N 1,1,2,3,3-pentafluoroprop-1-ene Chemical class FC(F)C(F)=C(F)F NDMMKOCNFSTXRU-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910000792 Monel Inorganic materials 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000004035 construction material Substances 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
- 238000013461 design Methods 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- -1 heat transfer media Substances 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 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
- 239000007858 starting material Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002699 waste material Substances 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
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B7/00—Halogens; Halogen acids
- C01B7/19—Fluorine; Hydrogen fluoride
- C01B7/191—Hydrogen fluoride
- C01B7/195—Separation; Purification
- C01B7/196—Separation; Purification by distillation
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73204105P | 2005-11-01 | 2005-11-01 | |
| US732041P | 2005-11-01 | ||
| PCT/US2006/042667 WO2007053688A2 (en) | 2005-11-01 | 2006-11-01 | Azeotrope compositions comprising 1,1,1,2,3-pentafluoropropene and hydrogen fluoride and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2383910T3 true ES2383910T3 (es) | 2012-06-27 |
Family
ID=37943754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES06827293T Active ES2383910T3 (es) | 2005-11-01 | 2006-11-01 | Composiciones de azeótropos que comprenden 1,2,3,3,3-pentafluoropropeno y fluoruro de hidrógeno y su uso |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7388117B2 (enExample) |
| EP (2) | EP2292575A1 (enExample) |
| JP (2) | JP5144525B2 (enExample) |
| KR (2) | KR101458650B1 (enExample) |
| CN (2) | CN101300215B (enExample) |
| AR (1) | AR058501A1 (enExample) |
| BR (1) | BRPI0619645A2 (enExample) |
| CA (1) | CA2627054A1 (enExample) |
| ES (1) | ES2383910T3 (enExample) |
| RU (1) | RU2444509C2 (enExample) |
| UA (1) | UA95083C2 (enExample) |
| WO (1) | WO2007053688A2 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7279451B2 (en) | 2002-10-25 | 2007-10-09 | Honeywell International Inc. | Compositions containing fluorine substituted olefins |
| AU2005236039B2 (en) | 2004-04-16 | 2008-08-21 | Honeywell International Inc. | Azeotrope-like compositions of tetrafluoropropene and trifluoroiodomethane |
| US8008244B2 (en) | 2004-04-29 | 2011-08-30 | Honeywell International Inc. | Compositions of tetrafluoropropene and hydrocarbons |
| 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 |
| 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 |
| JP5393454B2 (ja) | 2006-06-27 | 2014-01-22 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | １，２，３，３，３−ペンタフルオロプロペンの製造方法 |
| EP2041054B1 (en) * | 2006-07-13 | 2014-08-27 | E.I. Du Pont De Nemours And Company | Catalytic production processes for making 1,2,3,3,3-pentafluoropropene |
| US7803975B2 (en) | 2006-07-13 | 2010-09-28 | E.I. Du Pont De Nemours And Company | Process for separating a fluoroolefin from HF by liquid-liquid extraction |
| GB0614927D0 (en) * | 2006-07-27 | 2006-09-06 | Ineos Fluor Holdings Ltd | Separation process |
| 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 |
| US8232435B2 (en) * | 2006-09-05 | 2012-07-31 | E I Du Pont De Nemours And Company | 1,2,3,3,3-pentafluoropropene production processes |
| EP3345888B1 (en) | 2006-09-08 | 2020-11-25 | The Chemours Company FC, LLC | Extractive distillation processes to separate e-1,2,3,3,3-pentafluoropropene from z-1,2,3,3,3-pentafluoropropene |
| PL2185488T3 (pl) | 2007-09-13 | 2018-04-30 | Arkema Inc. | Kompozycje zawierające połączenie stereoizomerów Z i E fluorowodoroolefin |
| CN101952230B (zh) * | 2008-02-21 | 2015-07-22 | 纳幕尔杜邦公司 | 通过共沸蒸馏使2,3,3,3-四氟丙烯与氟化氢分离的方法 |
| 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 |
| 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 |
| 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 |
| US8436218B2 (en) * | 2010-05-27 | 2013-05-07 | Honeywell International Inc. | Azeotrope-like composition of hexafluoropropane, hexafluoropropene and hydrogen fluoride |
| US9309116B2 (en) * | 2011-09-26 | 2016-04-12 | Honeywell International Inc. | Method for producing high concentration aqueous HF solutions |
| FR2989084B1 (fr) * | 2012-04-04 | 2015-04-10 | Arkema France | Compositions a base de 2,3,3,4,4,4-hexafluorobut-1-ene |
| KR20160017661A (ko) | 2016-01-29 | 2016-02-16 | 한국과학기술연구원 | 헥사플루오로프로필렌으로부터 2,3,3,3-테트라플루오로프로펜과 1,3,3,3-테트라플루오로프로펜의 제조방법 |
| FR3067347B1 (fr) * | 2017-06-09 | 2020-07-24 | Arkema France | 1,1,1,2,3,3-hexafluoropropane de haute purete, son procede de fabrication et utilisation |
| CN110945099B (zh) | 2017-07-27 | 2024-07-05 | 科慕埃弗西有限公司 | 包含氟化氢和氟碳化合物的共沸组合物 |
| CN108359121B (zh) * | 2017-12-14 | 2019-03-15 | 浙江衢化氟化学有限公司 | 一种共沸和类共沸组合物 |
Family Cites Families (17)
| 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 |
| BR9306493A (pt) | 1992-06-05 | 1998-09-15 | Daikin Ind Ltd | Método para a manufatura de 1,1,1,2,3-pentafluoropropeno e método para a manufatura de 1,1,1,2,3-pentafluoropropano |
| WO1994018282A1 (en) * | 1993-02-05 | 1994-08-18 | E.I. Du Pont De Nemours And Company | Compositions of a hydrofluorocarbon and a hydrocarbon |
| US5538659A (en) | 1993-03-29 | 1996-07-23 | E. I. Du Pont De Nemours And Company | Refrigerant compositions including hexafluoropropane and a hydrofluorocarbon |
| US5396000A (en) * | 1993-05-24 | 1995-03-07 | E. I. Du Pont De Nemours And Company | Process for the manufacture of 1,1,1,2,3,-pentafluoropropane |
| US5563304A (en) * | 1994-05-26 | 1996-10-08 | E. I. Du Pont De Nemours And Company | Production of 1,2-dihydro and 2,2-dihydro hexafluoropropanes and azeotropes thereof with HF |
| MX9800871A (es) * | 1995-08-01 | 1998-04-30 | Du Pont | Proceso para la manufactura de halocarburos y compuestos seleccionados y azeotropos con hf. |
| 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 |
| JP2933014B2 (ja) * | 1996-01-23 | 1999-08-09 | ダイキン工業株式会社 | ペンタフルオロプロパンとフッ化水素の共沸混合物およびペンタフルオロプロパンの分離精製方法 |
| EP0958265B1 (en) | 1997-01-31 | 2003-04-02 | E.I. Du Pont De Nemours And Company | The catalytic manufacture of pentafluoropropenes |
| US6031141A (en) | 1997-08-25 | 2000-02-29 | E. I. Du Pont De Nemours And Company | Fluoroolefin manufacturing process |
| JP3525701B2 (ja) * | 1997-09-22 | 2004-05-10 | 信越化学工業株式会社 | 含フッ素アミド化合物 |
| US5918481A (en) * | 1997-11-20 | 1999-07-06 | Alliedsignal Inc. | Process for separating hydrogen fluoride from fluorocarbons |
| RU2210559C2 (ru) * | 1999-08-20 | 2003-08-20 | Институт элементоорганических соединений им.А.Н. Несмеянова РАН | Способ получения фторолефинов |
| US20060094911A1 (en) * | 2004-10-29 | 2006-05-04 | Rao Velliyur N M | Noncatalytic manufacture of 1,1,3,3,3-pentafluoropropene from 1,1,1,3,3,3-hexafluoropropane |
| 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 |
| 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
- 2006-10-30 US US11/590,448 patent/US7388117B2/en active Active
- 2006-11-01 RU RU2008121966/04A patent/RU2444509C2/ru not_active IP Right Cessation
- 2006-11-01 WO PCT/US2006/042667 patent/WO2007053688A2/en not_active Ceased
- 2006-11-01 KR KR1020087013109A patent/KR101458650B1/ko active Active
- 2006-11-01 ES ES06827293T patent/ES2383910T3/es active Active
- 2006-11-01 CN CN2006800408423A patent/CN101300215B/zh active Active
- 2006-11-01 EP EP10009450A patent/EP2292575A1/en not_active Withdrawn
- 2006-11-01 KR KR1020147017249A patent/KR101495013B1/ko active Active
- 2006-11-01 CN CN201210020745.5A patent/CN102516020B/zh active Active
- 2006-11-01 CA CA002627054A patent/CA2627054A1/en not_active Abandoned
- 2006-11-01 AR ARP060104799A patent/AR058501A1/es not_active Application Discontinuation
- 2006-11-01 EP EP06827293A patent/EP1948579B1/en not_active Revoked
- 2006-11-01 JP JP2008539002A patent/JP5144525B2/ja active Active
- 2006-11-01 UA UAA200804902A patent/UA95083C2/ru unknown
- 2006-11-01 BR BRPI0619645-4A patent/BRPI0619645A2/pt not_active IP Right Cessation
-
2012
- 2012-07-25 JP JP2012165143A patent/JP5567627B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN101300215B (zh) | 2012-03-28 |
| KR101495013B1 (ko) | 2015-02-24 |
| CN101300215A (zh) | 2008-11-05 |
| JP5567627B2 (ja) | 2014-08-06 |
| AR058501A1 (es) | 2008-02-06 |
| UA95083C2 (ru) | 2011-07-11 |
| CN102516020A (zh) | 2012-06-27 |
| BRPI0619645A2 (pt) | 2011-10-04 |
| JP2012207045A (ja) | 2012-10-25 |
| JP5144525B2 (ja) | 2013-02-13 |
| US7388117B2 (en) | 2008-06-17 |
| WO2007053688A3 (en) | 2007-08-02 |
| CN102516020B (zh) | 2014-12-24 |
| RU2008121966A (ru) | 2009-12-10 |
| EP2292575A1 (en) | 2011-03-09 |
| WO2007053688A2 (en) | 2007-05-10 |
| KR101458650B1 (ko) | 2014-11-05 |
| KR20140085609A (ko) | 2014-07-07 |
| EP1948579B1 (en) | 2012-03-21 |
| EP1948579A2 (en) | 2008-07-30 |
| RU2444509C2 (ru) | 2012-03-10 |
| KR20080066839A (ko) | 2008-07-16 |
| JP2009513714A (ja) | 2009-04-02 |
| US20070100174A1 (en) | 2007-05-03 |
| CA2627054A1 (en) | 2007-05-10 |
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