EP1178950A1 - Production de 1,1,1,2,3,3,3-heptafluoropropane - Google Patents
Production de 1,1,1,2,3,3,3-heptafluoropropaneInfo
- Publication number
- EP1178950A1 EP1178950A1 EP00927586A EP00927586A EP1178950A1 EP 1178950 A1 EP1178950 A1 EP 1178950A1 EP 00927586 A EP00927586 A EP 00927586A EP 00927586 A EP00927586 A EP 00927586A EP 1178950 A1 EP1178950 A1 EP 1178950A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- hydrogen fluoride
- phase
- hfc
- hfp
- liquid
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 title description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 105
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 104
- 239000007791 liquid phase Substances 0.000 claims abstract description 40
- 238000004821 distillation Methods 0.000 claims abstract description 34
- 239000012071 phase Substances 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 239000011541 reaction mixture Substances 0.000 claims abstract description 7
- 238000004064 recycling Methods 0.000 claims abstract description 7
- 230000005484 gravity Effects 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 239000012074 organic phase Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 abstract description 6
- 239000000047 product Substances 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 14
- 238000000926 separation method Methods 0.000 description 9
- 150000002894 organic compounds Chemical class 0.000 description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 238000003682 fluorination reaction Methods 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000005201 scrubbing Methods 0.000 description 4
- 241001469893 Oxyzygonectes dovii Species 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 229910019787 NbF5 Inorganic materials 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910004546 TaF5 Inorganic materials 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical class F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- QCMJBECJXQJLIL-UHFFFAOYSA-L chromium(6+);oxygen(2-);difluoride Chemical compound [O-2].[O-2].[F-].[F-].[Cr+6] QCMJBECJXQJLIL-UHFFFAOYSA-L 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000005828 hydrofluoroalkanes Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- AOLPZAHRYHXPLR-UHFFFAOYSA-I pentafluoroniobium Chemical compound F[Nb](F)(F)(F)F AOLPZAHRYHXPLR-UHFFFAOYSA-I 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YRGLXIVYESZPLQ-UHFFFAOYSA-I tantalum pentafluoride Chemical compound F[Ta](F)(F)(F)F YRGLXIVYESZPLQ-UHFFFAOYSA-I 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/087—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated 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
Definitions
- the present invention relates to a process for the production of 1,1,1,2,3,3,3-heptafluoropropane from hexafluoropropene and to a process for the separation of mixtures comprising 1,1,1,2,3,3,3-heptafluoropropane and hydrogen fluoride.
- reaction product phase-separates in the liquid phase to afford an organic-rich phase, which comprises HFC 227ea and HFP, and a hydrogen fluoride-rich phase.
- the mole fraction of HF to 227ea in the reaction product may be from about 0.1 to 0.9.
- the reaction mixture charged to the liquid-phase separator in Step (A) comprises an HFC 227ea/HF azeotrope, or azeotrope-like mixture, and optionally an HFP/HF azeotrope, or azeotrope-like mixture.
- the reaction mixture charged to the liquid-phase separator in Step A may be the mixture arising directly from the reactor in which HFP is reacted with hydrogen fluoride (direct mixture). It is often preferred, however, that the mixture charged to the liquid-phase separator is essentially an HFC 227ea/hydrogen fluoride azeotrope, for example obtained from distillation of the direct mixture.
- reaction of HFP with hydrogen fluoride in the process according to the first aspect of the present invention may be carried out in the liquid phase or in the vapour phase.
- Step A is preferably carried out at below ambient temperature, typically at below 30°C.
- Bottoms line (9) from the liquid-phase separator (7) is in fluid-flow communication with a second distillation column (10), which is for example a packed column.
- Distillation column (10) is typically operated at a pressure of around 12 bars with a tops temperature of 37°C and a bottoms temperature of around 60°C.
- Distillation column (10) is provided with an exit pipe for product (11) and a tops pipe (12).
- a stream comprising HFP and essentially all the hydrogen fluoride content of the stream entering distillation column (10) via line (9) is removed from the top of distillation column (1Q) via line (12) and the product stream HFC 227ea is removed from the bottom of column (10) via exit pipe (11).
- feed pipe (1) leads to a reactor (2), which optionally contains a fluorination catalyst.
- Line (14) from reactor (2) is provided with a feed line (13) and is in fluid-flow communication with a liquid-phase separator (7).
- Tops line (8) from the liquid-phase separator (7) is in fluid- flow communication with feed-pipe (1).
- Bottoms line (9) from the liquid-phase separator (7) is in fluid-flow communication with a distillation column (10), which is for example a packed column.
- Distillation column (10) is typically operated at a pressure of around 12 bars with a tops temperature of 37°C and a bottoms temperature of around 60°C.
- Distillation column (10) is provided with an exit pipe for product (11) and a tops pipe (12) which is in fluid flow communication with line (14) to liquid-phase separator (7).
- the organics-rich phase flows via bottoms line (9) to distillation column (10).
- a stream comprising HFP and essentially all the hydrogen fluoride content of the stream entering distillation column (10) via line (9) is removed from the top of distillation column (10) via line (12) and returned to the liquid phase separator (7) via line (14).
- the product stream HFC 227ea is removed from the bottom of column (10) via exit pipe (11).
- compositions in the area of the figure designated A phase-separate namely compositions comprising 0.4-0.6 mole % HF, greater than 0.4 mole % HFP and less than 0.6 mole % HFC 227ea.
- a phase-separate namely compositions comprising 0.4-0.6 mole % HF, greater than 0.4 mole % HFP and less than 0.6 mole % HFC 227ea.
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)
- Physical Or Chemical Processes And Apparatus (AREA)
Abstract
La présente invention concerne un procédé de préparation de 1,1,1,2,3,3,3-heptafluoropropane (HFC 227ea) consistant à faire réagir un hexafluoropropane (HFP) avec un fluorure d'hydrogène. Ledit procédé consiste: à charger le mélange réactionnel dans un séparateur en phase liquide; à permettre à une phase riche en HFC 227ea de se séparer par effet de gravité; à recycler la phase riche en fluorure d'hydrogène; à charger la phase riche en HFC 227ea dans une colonne de distillation; à récupérer séparément le HFC 227ea et un mélange riche en fluorure d'hydrogène contenus dans la colonne de distillation; puis à recycler le mélange riche en fluorure d'hydrogène dans le réacteur.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13465799P | 1999-05-18 | 1999-05-18 | |
| US134657P | 1999-05-18 | ||
| GBGB9911475.3A GB9911475D0 (en) | 1999-05-18 | 1999-05-18 | Production of 1,1,1,2,3,3,3-heptafluoropropane liquid phase separation |
| GB9911475 | 1999-05-18 | ||
| PCT/GB2000/001861 WO2000069797A1 (fr) | 1999-05-18 | 2000-05-15 | Production de 1,1,1,2,3,3,3-heptafluoropropane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1178950A1 true EP1178950A1 (fr) | 2002-02-13 |
Family
ID=26315556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP00927586A Withdrawn EP1178950A1 (fr) | 1999-05-18 | 2000-05-15 | Production de 1,1,1,2,3,3,3-heptafluoropropane |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1178950A1 (fr) |
| JP (1) | JP2002544248A (fr) |
| AU (1) | AU769137B2 (fr) |
| CA (1) | CA2373437A1 (fr) |
| WO (1) | WO2000069797A1 (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1291337A1 (fr) * | 2001-09-07 | 2003-03-12 | SOLVAY (Société Anonyme) | Procédé pour l'obtention d'heptafluoropropane purifié |
| US20070106099A1 (en) * | 2005-11-10 | 2007-05-10 | Pcbu Services, Inc. | Production processes and systems |
| US8008243B2 (en) * | 2008-10-31 | 2011-08-30 | Honeywell International Inc. | Azeotrope-like compositions of 1,1,2,3-tetrachloropropene and hydrogen fluoride |
| CN107635955A (zh) * | 2015-05-21 | 2018-01-26 | 科慕埃弗西有限公司 | 通过SbF5进行的1233xf至244bb的氢氟化 |
| CN117164427A (zh) * | 2023-09-04 | 2023-12-05 | 临海市利民化工有限公司 | 一种七氟丙烷的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2675496B1 (fr) * | 1991-04-17 | 1993-09-03 | Atochem | Procede de separation du fluorure d'hydrogene de ses melanges avec le 1,1,1-trifluoro-2-chloroethane. |
| AU747117B2 (en) * | 1997-11-25 | 2002-05-09 | Ineos Fluor Holdings Limited | Preparation of fluorine-containing organic compounds |
| DE69911186T2 (de) * | 1998-04-03 | 2004-07-15 | E.I. Du Pont De Nemours And Co., Wilmington | Verfahren zur reinigung und verwendung von 2-chloro-1,1,1,2,3,3,3-heptafluorpropan und ihre azeotrope mit hf |
-
2000
- 2000-05-15 CA CA002373437A patent/CA2373437A1/fr not_active Abandoned
- 2000-05-15 JP JP2000618218A patent/JP2002544248A/ja active Pending
- 2000-05-15 WO PCT/GB2000/001861 patent/WO2000069797A1/fr not_active Ceased
- 2000-05-15 EP EP00927586A patent/EP1178950A1/fr not_active Withdrawn
- 2000-05-15 AU AU45977/00A patent/AU769137B2/en not_active Ceased
Non-Patent Citations (1)
| Title |
|---|
| See references of WO0069797A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002544248A (ja) | 2002-12-24 |
| AU769137B2 (en) | 2004-01-15 |
| CA2373437A1 (fr) | 2000-11-23 |
| WO2000069797A1 (fr) | 2000-11-23 |
| AU4597700A (en) | 2000-12-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed |
Effective date: 20011116 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE |
|
| AX | Request for extension of the european patent |
Free format text: AL;LT;LV;MK;RO;SI |
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| 17Q | First examination report despatched |
Effective date: 20030108 |
|
| GRAP | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOSNIGR1 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
| 18D | Application deemed to be withdrawn |
Effective date: 20040224 |