CA2778250A1 - Hydrogen fluoride-hfc-254eb azeotrope and its uses - Google Patents
Hydrogen fluoride-hfc-254eb azeotrope and its uses Download PDFInfo
- Publication number
- CA2778250A1 CA2778250A1 CA2778250A CA2778250A CA2778250A1 CA 2778250 A1 CA2778250 A1 CA 2778250A1 CA 2778250 A CA2778250 A CA 2778250A CA 2778250 A CA2778250 A CA 2778250A CA 2778250 A1 CA2778250 A1 CA 2778250A1
- Authority
- CA
- Canada
- Prior art keywords
- tetrafluoropropane
- composition
- azeotropic
- hydrogen fluoride
- pentafluoropropane
- 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.)
- Abandoned
Links
- 239000001257 hydrogen Substances 0.000 title description 14
- 229910052739 hydrogen Inorganic materials 0.000 title description 14
- 125000004435 hydrogen atom Chemical class [H]* 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 192
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 146
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 143
- INEMUVRCEAELBK-UHFFFAOYSA-N 1,1,1,2-tetrafluoropropane Chemical compound CC(F)C(F)(F)F INEMUVRCEAELBK-UHFFFAOYSA-N 0.000 claims abstract description 109
- 238000004821 distillation Methods 0.000 claims abstract description 65
- ZDCWZRQSHBQRGN-UHFFFAOYSA-N 1,1,1,2,3-pentafluoropropane Chemical compound FCC(F)C(F)(F)F ZDCWZRQSHBQRGN-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 45
- 238000000926 separation method Methods 0.000 claims description 13
- IATQMZSYBZMIPZ-UHFFFAOYSA-N 1,1,1,2,3-pentafluoropropane 1,1,1,2-tetrafluoropropane Chemical compound CC(F)C(F)(F)F.FCC(F)C(F)(F)F IATQMZSYBZMIPZ-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 230000008901 benefit Effects 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- WFHFXEYKXJKYMG-UHFFFAOYSA-N 1,1,2-trichloro-1,3,3,3-tetrafluoropropane Chemical compound FC(F)(F)C(Cl)C(F)(Cl)Cl WFHFXEYKXJKYMG-UHFFFAOYSA-N 0.000 description 7
- DMUPYMORYHFFCT-UHFFFAOYSA-N 1,2,3,3,3-pentafluoroprop-1-ene Chemical compound FC=C(F)C(F)(F)F DMUPYMORYHFFCT-UHFFFAOYSA-N 0.000 description 6
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 6
- 238000013459 approach Methods 0.000 description 6
- BIPNYHXPHOUMCL-UHFFFAOYSA-N 1,1,2-trichloro-1,2,3,3,3-pentafluoropropane Chemical compound FC(F)(F)C(F)(Cl)C(F)(Cl)Cl BIPNYHXPHOUMCL-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000003507 refrigerant Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005796 dehydrofluorination reaction Methods 0.000 description 2
- 230000000779 depleting effect Effects 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- LDMYCECIGXPKDO-UHFFFAOYSA-N 2-chloro-1,1,1,2,3-pentafluoropropane Chemical compound FCC(F)(Cl)C(F)(F)F LDMYCECIGXPKDO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
- C07C17/38—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
- C07C17/386—Separation; Purification; Stabilisation; Use of additives by distillation with auxiliary compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25634009P | 2009-10-30 | 2009-10-30 | |
| US61/256,340 | 2009-10-30 | ||
| PCT/US2010/052237 WO2011053449A1 (en) | 2009-10-30 | 2010-10-12 | Hydrogen fluoride-hfc-254eb azeotrope and its uses |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2778250A1 true CA2778250A1 (en) | 2011-05-05 |
Family
ID=43447920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2778250A Abandoned CA2778250A1 (en) | 2009-10-30 | 2010-10-12 | Hydrogen fluoride-hfc-254eb azeotrope and its uses |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8486293B2 (enExample) |
| EP (1) | EP2493836B1 (enExample) |
| JP (1) | JP5706909B2 (enExample) |
| KR (1) | KR20120099703A (enExample) |
| CN (1) | CN102666453B (enExample) |
| BR (1) | BR112012009821A2 (enExample) |
| CA (1) | CA2778250A1 (enExample) |
| ES (1) | ES2545740T3 (enExample) |
| HU (1) | HUP1200449A2 (enExample) |
| IN (1) | IN2012DN03132A (enExample) |
| MX (1) | MX2012004921A (enExample) |
| RU (1) | RU2012122225A (enExample) |
| TW (1) | TW201119978A (enExample) |
| WO (1) | WO2011053449A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103396288B (zh) * | 2006-06-27 | 2016-12-28 | 纳幕尔杜邦公司 | 1,2,3,3,3-五氟丙烯制备方法 |
| US8513474B2 (en) | 2010-06-24 | 2013-08-20 | Honeywell International Inc. | Process for the manufacture of fluorinated olefins |
| WO2013130342A1 (en) * | 2012-03-02 | 2013-09-06 | Arkema Inc. | Process for the removal of contaminant from a hydrochlorofluoroolefin by extractive distillation |
| BR112019008414A2 (pt) * | 2016-12-21 | 2019-07-09 | Arkema Inc | processos e sistemas para recuperar r1233zd na forma purificada |
| JP6485493B2 (ja) * | 2017-06-16 | 2019-03-20 | ダイキン工業株式会社 | ペンタフルオロプロパンと水とを含む共沸又は共沸様組成物、並びにペンタフルオロプロパンの製造方法 |
| US10851303B2 (en) | 2017-07-27 | 2020-12-01 | The Chemours Company Fc, Llc | Azeotropic compositions comprising hydrogen fluoride and fluorocarbons |
| CN111094503B (zh) * | 2017-09-11 | 2022-04-01 | 科慕埃弗西有限公司 | 包含氟化氢和含氟烃的共沸组合物 |
| US10351494B1 (en) * | 2018-01-08 | 2019-07-16 | Honeywell International Inc. | Systems and methods for reducing the formation of impurities during 244bb dehydrochlorination to 1234yf |
| JP7670992B2 (ja) | 2020-03-19 | 2025-05-01 | 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 |
| WO2022085544A1 (ja) * | 2020-10-22 | 2022-04-28 | Ａｇｃ株式会社 | 電気設備 |
| JP7861637B2 (ja) * | 2021-01-29 | 2026-05-19 | Ａｇｃ株式会社 | ３－クロロ－１，１，２，２－テトラフルオロプロパンの製造方法および１－クロロ－２，３，３－トリフルオロプロペンの製造方法 |
| CN113624570B (zh) * | 2021-08-06 | 2023-04-28 | 清华大学 | 汽液相平衡装置及氟代烃中的hf的分析方法 |
| CN114350321B (zh) * | 2021-12-03 | 2024-02-09 | 湖北瑞能华辉能源管理有限公司 | 一种节能环保型热泵工质及其应用 |
| CA3267075A1 (en) | 2022-11-18 | 2024-05-23 | The Chemours Company Fc, Llc | METHODS FOR SEPARING MIXTURES COMPRISING 1,1,1,3-TETRAFLUOROPROPANE, 3,3,3-TRIFLUOROPROPENE AND HYDROGEN FLUORIDE AND AZEOTROPES THEREOF |
| JP2025536644A (ja) | 2022-11-18 | 2025-11-07 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | ３－クロロ－３，３－ジフルオロ－１－プロペン、３，３，３－トリフルオロプロペン、及びフッ化水素の共沸性混合物 |
| FR3151590B1 (fr) * | 2023-07-27 | 2026-01-30 | Dehon | Procede et installation pour la separation d’un melange comprenant au moins un fluide fluore et un ou plusieurs contaminants |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4944846A (en) | 1988-08-01 | 1990-07-31 | E. I. Dupont De Nemours And Company | Process for the separation of HF via Azeotropic distillation |
| 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 |
| BR9407232A (pt) * | 1993-08-11 | 1996-09-24 | Bayer Ag | Compostos de tiocarbamoíla |
| US5918481A (en) * | 1997-11-20 | 1999-07-06 | Alliedsignal Inc. | Process for separating hydrogen fluoride from fluorocarbons |
| 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 |
| US7476771B2 (en) | 2005-11-01 | 2009-01-13 | E.I. Du Pont De Nemours + Company | Azeotrope compositions comprising 2,3,3,3-tetrafluoropropene and hydrogen fluoride and uses thereof |
| US7888539B2 (en) | 2007-02-23 | 2011-02-15 | E.I. Du Pont De Nemours And Company | Azeotrope compositions of octafluorocyclobutane and uses thereof |
| GB0801209D0 (en) | 2008-01-23 | 2008-02-27 | Ineos Fluor Holdings Ltd | Process |
| ES2610615T3 (es) | 2008-02-21 | 2017-04-28 | The Chemours Company Fc, Llc | Composiciones de azeótropos que comprenden 3,3,3-trifluoropropeno y fluoruro de hidrógeno y procedimientos para la separación de los mismos |
| EP2098499B2 (en) | 2008-03-06 | 2017-11-22 | Honeywell International Inc. | Azeotrope-like composition of 2-chloro-3,3,3-trifluoropropene (HCFC-1233xf) and hydrogen fluoride (HF) |
| US8845921B2 (en) | 2008-04-09 | 2014-09-30 | Honeywell International Inc. | Separation of close boiling compounds by addition of a third compound |
-
2010
- 2010-10-06 US US12/898,983 patent/US8486293B2/en active Active
- 2010-10-12 HU HU1200449A patent/HUP1200449A2/hu unknown
- 2010-10-12 MX MX2012004921A patent/MX2012004921A/es active IP Right Grant
- 2010-10-12 RU RU2012122225/04A patent/RU2012122225A/ru unknown
- 2010-10-12 WO PCT/US2010/052237 patent/WO2011053449A1/en not_active Ceased
- 2010-10-12 CN CN201080048381.0A patent/CN102666453B/zh active Active
- 2010-10-12 JP JP2012536843A patent/JP5706909B2/ja active Active
- 2010-10-12 BR BR112012009821A patent/BR112012009821A2/pt not_active IP Right Cessation
- 2010-10-12 KR KR1020127013791A patent/KR20120099703A/ko not_active Withdrawn
- 2010-10-12 CA CA2778250A patent/CA2778250A1/en not_active Abandoned
- 2010-10-12 EP EP10768151.2A patent/EP2493836B1/en active Active
- 2010-10-12 ES ES10768151.2T patent/ES2545740T3/es active Active
- 2010-10-18 TW TW099135476A patent/TW201119978A/zh unknown
-
2012
- 2012-04-11 IN IN3132DEN2012 patent/IN2012DN03132A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR112012009821A2 (pt) | 2016-10-18 |
| JP2013509409A (ja) | 2013-03-14 |
| RU2012122225A (ru) | 2013-12-10 |
| TW201119978A (en) | 2011-06-16 |
| CN102666453B (zh) | 2015-11-25 |
| CN102666453A (zh) | 2012-09-12 |
| WO2011053449A1 (en) | 2011-05-05 |
| IN2012DN03132A (enExample) | 2015-09-18 |
| MX2012004921A (es) | 2012-05-22 |
| KR20120099703A (ko) | 2012-09-11 |
| EP2493836A1 (en) | 2012-09-05 |
| US8486293B2 (en) | 2013-07-16 |
| EP2493836B1 (en) | 2015-07-08 |
| HUP1200449A2 (en) | 2012-11-28 |
| US20110101264A1 (en) | 2011-05-05 |
| ES2545740T3 (es) | 2015-09-15 |
| JP5706909B2 (ja) | 2015-04-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20141015 |