ES2463670T3 - Procesos para la separación de 2,3,3,3-tetrafluoropropeno del fluoruro de hidrógeno por destilación azeotrópica - Google Patents
Procesos para la separación de 2,3,3,3-tetrafluoropropeno del fluoruro de hidrógeno por destilación azeotrópica Download PDFInfo
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- ES2463670T3 ES2463670T3 ES09713183.3T ES09713183T ES2463670T3 ES 2463670 T3 ES2463670 T3 ES 2463670T3 ES 09713183 T ES09713183 T ES 09713183T ES 2463670 T3 ES2463670 T3 ES 2463670T3
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- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 title claims abstract description 455
- 238000000034 method Methods 0.000 title claims abstract description 111
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 title claims description 448
- 229910000040 hydrogen fluoride Inorganic materials 0.000 title claims description 447
- 238000000926 separation method Methods 0.000 title claims description 49
- 238000010533 azeotropic distillation Methods 0.000 title description 29
- 239000000203 mixture Substances 0.000 claims abstract description 368
- 238000004821 distillation Methods 0.000 claims abstract description 218
- 239000012071 phase Substances 0.000 claims abstract description 135
- 239000007791 liquid phase Substances 0.000 claims abstract description 65
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 239000003795 chemical substances by application Substances 0.000 claims description 184
- FDOPVENYMZRARC-UHFFFAOYSA-N 1,1,1,2,2-pentafluoropropane Chemical compound CC(F)(F)C(F)(F)F FDOPVENYMZRARC-UHFFFAOYSA-N 0.000 claims description 90
- ZDCWZRQSHBQRGN-UHFFFAOYSA-N 1,1,1,2,3-pentafluoropropane Chemical compound FCC(F)C(F)(F)F ZDCWZRQSHBQRGN-UHFFFAOYSA-N 0.000 claims description 84
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 35
- RFCAUADVODFSLZ-UHFFFAOYSA-N 1-Chloro-1,1,2,2,2-pentafluoroethane Chemical compound FC(F)(F)C(F)(F)Cl RFCAUADVODFSLZ-UHFFFAOYSA-N 0.000 claims description 28
- 235000019406 chloropentafluoroethane Nutrition 0.000 claims description 28
- 239000003292 glue Substances 0.000 claims description 28
- QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 claims description 16
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 11
- 238000004064 recycling Methods 0.000 claims description 10
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 claims description 8
- WUMVZXWBOFOYAW-UHFFFAOYSA-N 1,2,3,3,4,4,4-heptafluoro-1-(1,2,3,3,4,4,4-heptafluorobut-1-enoxy)but-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)=C(F)OC(F)=C(F)C(F)(F)C(F)(F)F WUMVZXWBOFOYAW-UHFFFAOYSA-N 0.000 claims description 8
- HTHNTJCVPNKCPZ-UHFFFAOYSA-N 2-chloro-1,1-difluoroethene Chemical group FC(F)=CCl HTHNTJCVPNKCPZ-UHFFFAOYSA-N 0.000 claims description 8
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 8
- 235000019404 dichlorodifluoromethane Nutrition 0.000 claims description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 8
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 claims description 8
- BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- CGZAMBNIGLUBRY-UHFFFAOYSA-N difluoro(methoxy)methane Chemical compound COC(F)F CGZAMBNIGLUBRY-UHFFFAOYSA-N 0.000 claims description 7
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 7
- 238000000746 purification Methods 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 claims description 5
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- ORNGPPZBMMHKPM-UHFFFAOYSA-N 1,1,1,2,2-pentafluoro-2-(1,1,2,2,2-pentafluoroethoxy)ethane Chemical compound FC(F)(F)C(F)(F)OC(F)(F)C(F)(F)F ORNGPPZBMMHKPM-UHFFFAOYSA-N 0.000 claims description 4
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 claims description 4
- GQUXQQYWQKRCPL-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluorocyclopropane Chemical compound FC1(F)C(F)(F)C1(F)F GQUXQQYWQKRCPL-UHFFFAOYSA-N 0.000 claims description 4
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical group FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 4
- BAMUEXIPKSRTBS-UHFFFAOYSA-N 1,1-dichloro-1,2,2,2-tetrafluoroethane Chemical compound FC(F)(F)C(F)(Cl)Cl BAMUEXIPKSRTBS-UHFFFAOYSA-N 0.000 claims description 4
- FRCHKSNAZZFGCA-UHFFFAOYSA-N 1,1-dichloro-1-fluoroethane Chemical compound CC(F)(Cl)Cl FRCHKSNAZZFGCA-UHFFFAOYSA-N 0.000 claims description 4
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 claims description 4
- JSEUKVSKOHVLOV-UHFFFAOYSA-N 1,2-dichloro-1,1,2,3,3,3-hexafluoropropane Chemical compound FC(F)(F)C(F)(Cl)C(F)(F)Cl JSEUKVSKOHVLOV-UHFFFAOYSA-N 0.000 claims description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 4
- BOUGCJDAQLKBQH-UHFFFAOYSA-N 1-chloro-1,2,2,2-tetrafluoroethane Chemical compound FC(Cl)C(F)(F)F BOUGCJDAQLKBQH-UHFFFAOYSA-N 0.000 claims description 4
- YVOASHYXFVSAQN-UHFFFAOYSA-N 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)C(Cl)(Cl)C(F)(F)F YVOASHYXFVSAQN-UHFFFAOYSA-N 0.000 claims description 4
- CYXIKYKBLDZZNW-UHFFFAOYSA-N 2-Chloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)CCl CYXIKYKBLDZZNW-UHFFFAOYSA-N 0.000 claims description 4
- KJGXPVLCSICDQG-UHFFFAOYSA-N 2-chloro-1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)(Cl)C(F)(F)F KJGXPVLCSICDQG-UHFFFAOYSA-N 0.000 claims description 4
- YTCHAEAIYHLXBK-UHFFFAOYSA-N 2-chloro-1,1,3,3,3-pentafluoroprop-1-ene Chemical compound FC(F)=C(Cl)C(F)(F)F YTCHAEAIYHLXBK-UHFFFAOYSA-N 0.000 claims description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 239000004340 Chloropentafluoroethane Substances 0.000 claims description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004338 Dichlorodifluoromethane Substances 0.000 claims description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 claims description 4
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 claims description 4
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 claims description 4
- OOXWYYGXTJLWHA-UHFFFAOYSA-N cyclopropene Chemical compound C1C=C1 OOXWYYGXTJLWHA-UHFFFAOYSA-N 0.000 claims description 4
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- WMIYKQLTONQJES-UHFFFAOYSA-N hexafluoroethane Chemical compound FC(F)(F)C(F)(F)F WMIYKQLTONQJES-UHFFFAOYSA-N 0.000 claims description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 4
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 4
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 claims description 4
- 229960004065 perflutren Drugs 0.000 claims description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims description 4
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 claims description 4
- LCWWNOJPOGPGQK-UHFFFAOYSA-N trifluoro(fluoromethoxy)methane Chemical compound FCOC(F)(F)F LCWWNOJPOGPGQK-UHFFFAOYSA-N 0.000 claims description 4
- GCDWNCOAODIANN-UHFFFAOYSA-N 1,1,1,2,2-pentafluoro-2-methoxyethane Chemical compound COC(F)(F)C(F)(F)F GCDWNCOAODIANN-UHFFFAOYSA-N 0.000 claims description 3
- JQZFYIGAYWLRCC-UHFFFAOYSA-N 1-chloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)(F)Cl JQZFYIGAYWLRCC-UHFFFAOYSA-N 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- WBCLXFIDEDJGCC-UHFFFAOYSA-N hexafluoro-2-butyne Chemical compound FC(F)(F)C#CC(F)(F)F WBCLXFIDEDJGCC-UHFFFAOYSA-N 0.000 claims description 3
- 229940050176 methyl chloride Drugs 0.000 claims description 3
- KAVGMUDTWQVPDF-UHFFFAOYSA-N perflubutane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)F KAVGMUDTWQVPDF-UHFFFAOYSA-N 0.000 claims description 3
- WSJULBMCKQTTIG-OWOJBTEDSA-N (e)-1,1,1,2,3,4,4,4-octafluorobut-2-ene Chemical compound FC(F)(F)C(/F)=C(\F)C(F)(F)F WSJULBMCKQTTIG-OWOJBTEDSA-N 0.000 claims description 2
- XDIDQEGAKCWQQP-OWOJBTEDSA-N (e)-2,3-dichloro-1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)C(\Cl)=C(/Cl)C(F)(F)F XDIDQEGAKCWQQP-OWOJBTEDSA-N 0.000 claims description 2
- LGPPATCNSOSOQH-UHFFFAOYSA-N 1,1,2,3,4,4-hexafluorobuta-1,3-diene Chemical compound FC(F)=C(F)C(F)=C(F)F LGPPATCNSOSOQH-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- BHNZEZWIUMJCGF-UHFFFAOYSA-N 1-chloro-1,1-difluoroethane Chemical compound CC(F)(F)Cl BHNZEZWIUMJCGF-UHFFFAOYSA-N 0.000 claims description 2
- 239000004341 Octafluorocyclobutane Substances 0.000 claims description 2
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 claims description 2
- 229940099364 dichlorofluoromethane Drugs 0.000 claims description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
- 239000001282 iso-butane Substances 0.000 claims description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 2
- 235000019407 octafluorocyclobutane Nutrition 0.000 claims description 2
- BCCOBQSFUDVTJQ-UHFFFAOYSA-N octafluorocyclobutane Chemical compound FC1(F)C(F)(F)C(F)(F)C1(F)F BCCOBQSFUDVTJQ-UHFFFAOYSA-N 0.000 claims description 2
- SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 claims description 2
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims description 2
- 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 claims 1
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 claims 1
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims 1
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- 238000009835 boiling Methods 0.000 description 45
- 239000007788 liquid Substances 0.000 description 24
- 238000010992 reflux Methods 0.000 description 22
- 238000005796 dehydrofluorination reaction Methods 0.000 description 17
- 150000001336 alkenes Chemical class 0.000 description 15
- SUAMPXQALWYDBK-UHFFFAOYSA-N 1,1,1,2,2,3-hexafluoropropane Chemical compound FCC(F)(F)C(F)(F)F SUAMPXQALWYDBK-UHFFFAOYSA-N 0.000 description 14
- 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 description 12
- 239000001294 propane Substances 0.000 description 12
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
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- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
- B01D3/36—Azeotropic distillation
-
- 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
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Separation By Low-Temperature Treatments (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3035908P | 2008-02-21 | 2008-02-21 | |
| US30359 | 2008-02-21 | ||
| PCT/US2009/034470 WO2009105512A1 (en) | 2008-02-21 | 2009-02-19 | Processes for separation of 2,3,3,3-tetrafluoropropene from hydrogen fluoride by azeotropic distillation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2463670T3 true ES2463670T3 (es) | 2014-05-28 |
Family
ID=40513940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09713183.3T Active ES2463670T3 (es) | 2008-02-21 | 2009-02-19 | Procesos para la separación de 2,3,3,3-tetrafluoropropeno del fluoruro de hidrógeno por destilación azeotrópica |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP2247561B1 (https=) |
| JP (1) | JP2011513227A (https=) |
| KR (4) | KR20100138933A (https=) |
| CN (1) | CN101952230B (https=) |
| BR (1) | BRPI0906014A2 (https=) |
| CA (1) | CA2713086A1 (https=) |
| ES (1) | ES2463670T3 (https=) |
| MX (1) | MX2010009080A (https=) |
| RU (1) | RU2476416C2 (https=) |
| WO (1) | WO2009105512A1 (https=) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8766020B2 (en) * | 2008-07-31 | 2014-07-01 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| JP5439177B2 (ja) | 2006-08-24 | 2014-03-12 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 共沸蒸留によってフッ化水素からフルオロオレフィンを分離する方法 |
| EP4328213A3 (en) * | 2006-10-27 | 2024-04-03 | Honeywell International Inc. | A high purity 2,3,3,3-tetrafluoropropene |
| WO2011052559A1 (ja) * | 2009-10-27 | 2011-05-05 | 昭和電工株式会社 | フッ素含有化合物の精製方法 |
| KR101458679B1 (ko) * | 2009-11-10 | 2014-11-05 | 다이킨 고교 가부시키가이샤 | 2,3,3,3-테트라플루오로프로펜의 정제 방법 |
| WO2011099604A2 (en) * | 2010-02-12 | 2011-08-18 | Daikin Industries, Ltd. | Process for producing fluorine-containing alkene |
| WO2012011609A1 (en) | 2010-07-23 | 2012-01-26 | Daikin Industries, Ltd. | Purification method of 2,3,3,3-tetrafluoropropene |
| US8518293B2 (en) | 2010-09-03 | 2013-08-27 | Honeywell International Inc. | 1,3,3,3-tetrafluoropropene process azeotropes with HF |
| FR2977584B1 (fr) * | 2011-07-08 | 2014-12-05 | Arkema France | Procede de separation et recuperation du 2,3,3,3-tetrafluoropropene et de l'acide fluorhydrique |
| FR2986525B1 (fr) * | 2012-02-03 | 2014-02-14 | Arkema France | Procede de production de 2,3,3,3-tetrafluoropropene |
| WO2013154059A1 (ja) * | 2012-04-09 | 2013-10-17 | 旭硝子株式会社 | 共沸または共沸様組成物、および２，３，３，３－テトラフルオロプロペンまたはクロロメタンの製造方法 |
| JP6011008B2 (ja) * | 2012-04-27 | 2016-10-19 | 旭硝子株式会社 | 共沸または共沸様組成物、および２，３，３，３−テトラフルオロプロペンまたはヘキサフルオロプロペンの製造方法 |
| FR3000093B1 (fr) * | 2012-12-26 | 2015-07-17 | Arkema France | Composition azeotropique ou quasi-azeotropique de chloromethane |
| FR3000096B1 (fr) | 2012-12-26 | 2015-02-20 | Arkema France | Composition comprenant du 2,3,3,3-tetrafluoropropene |
| FR3003565B1 (fr) * | 2013-03-20 | 2018-06-29 | Arkema France | Composition comprenant hf et 2,3,3,3-tetrafluoropropene |
| KR101486361B1 (ko) * | 2013-04-09 | 2015-01-27 | 주식회사 세라젬 | 온열치료기용 자동 장력조절장치 |
| FR3023286B1 (fr) * | 2014-07-02 | 2018-02-16 | Arkema France | Procede de fabrication de tetrafluoropropene |
| EP3141587B1 (en) | 2015-02-19 | 2019-05-08 | Daikin Industries, Ltd. | Composition containing mixture of fluorinated hydrocarbons, and method for producing same |
| GB2540427B (en) | 2015-07-17 | 2017-07-19 | Mexichem Fluor Sa De Cv | Process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) |
| FR3046165B1 (fr) * | 2015-12-23 | 2019-12-13 | Arkema France | Procede de production et de purification du 2,3,3,3-tetrafluoro-1-propene |
| JP2017122063A (ja) * | 2016-01-06 | 2017-07-13 | ダイキン工業株式会社 | ２，３，３，３−テトラフルオロプロペンの製造方法 |
| 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 |
| 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 |
| FR3077572B1 (fr) * | 2018-02-05 | 2021-10-08 | Arkema France | Composition azeotropique ou quasi-azeotropique ternaire comprenant hf, 2,3,3,3-tetrafluoropropene et 1,1,1,2,2,-pentafluoropropane. |
| EP3861083B1 (en) * | 2018-10-04 | 2024-03-20 | The Chemours Company FC, LLC | Azeotropic composition of hfo-1234yf and ethane |
| JP6863489B2 (ja) * | 2019-01-28 | 2021-04-21 | ダイキン工業株式会社 | １，２−ジフルオロエチレン又は１，１，２−トリフルオロエチレンと、フッ化水素とを含む共沸様組成物 |
| CN114940888B (zh) * | 2022-06-29 | 2023-02-28 | 珠海格力电器股份有限公司 | 制冷剂及其制备方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53116314A (en) * | 1977-03-19 | 1978-10-11 | Mitsui Petrochem Ind Ltd | Separation of acetic acid and water |
| US4975156A (en) * | 1989-05-04 | 1990-12-04 | Atochem North America, Inc. | Process for the separation of hydrogen fluoride, 1,1-dichloro-1-fluoroethane and 1-chloro-1,1-difluoroethane from liquid mixtures thereof |
| IT1256631B (it) * | 1992-12-10 | 1995-12-12 | Ausimont Spa | Procedimento per la separazione di hf da sue miscele con gli idroclorofluorcarburi 123 e/o 124 |
| WO1999020585A1 (en) * | 1997-10-17 | 1999-04-29 | E.I. Du Pont De Nemours And Company | Separating 1,1,1,3,3-pentafluoropropane from hydrogen fluoride |
| US6521803B1 (en) * | 1998-12-18 | 2003-02-18 | Solvay (Societe Anonyme) | Method for separating a mixture comprising at least an hydrofluoroalkane and hydrogen fluoride, methods for preparing a hydrofluoroalkane and azeotropic compositions |
| WO2002059067A1 (en) * | 2001-01-25 | 2002-08-01 | Honeywell International, Inc. | Process for the manufacture of fluorocarbons |
| US20050177012A1 (en) * | 2001-07-20 | 2005-08-11 | Pcbu Services, Inc. | Halocarbon production processes, halocarbon separation processes, and halocarbon separation systems |
| 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 |
| US20060116538A1 (en) * | 2004-10-29 | 2006-06-01 | Ralph Newton Miller | Azeotrope compositions comprising 1,1,3,3,3-pentafluoropropene and hydrogen fluoride and uses thereof |
| 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 |
| US7423188B2 (en) * | 2005-11-01 | 2008-09-09 | E. I. Du Pont De Nemours And Company | Azeotrope compositions comprising E-1,3,3,3-tetrafluoropropene 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 |
| 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 |
| JP5439177B2 (ja) * | 2006-08-24 | 2014-03-12 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 共沸蒸留によってフッ化水素からフルオロオレフィンを分離する方法 |
-
2009
- 2009-02-19 WO PCT/US2009/034470 patent/WO2009105512A1/en not_active Ceased
- 2009-02-19 JP JP2010547739A patent/JP2011513227A/ja active Pending
- 2009-02-19 KR KR1020107020746A patent/KR20100138933A/ko not_active Ceased
- 2009-02-19 CN CN200980105927.9A patent/CN101952230B/zh active Active
- 2009-02-19 EP EP09713183.3A patent/EP2247561B1/en active Active
- 2009-02-19 KR KR1020197003238A patent/KR20190016124A/ko not_active Ceased
- 2009-02-19 BR BRPI0906014-6A patent/BRPI0906014A2/pt not_active IP Right Cessation
- 2009-02-19 MX MX2010009080A patent/MX2010009080A/es active IP Right Grant
- 2009-02-19 CA CA2713086A patent/CA2713086A1/en not_active Abandoned
- 2009-02-19 RU RU2010138783/04A patent/RU2476416C2/ru not_active IP Right Cessation
- 2009-02-19 ES ES09713183.3T patent/ES2463670T3/es active Active
- 2009-02-19 KR KR1020167027807A patent/KR101842380B1/ko active Active
- 2009-02-19 KR KR1020187007744A patent/KR101946378B1/ko active Active
Also Published As
| Publication number | Publication date |
|---|---|
| KR20180031811A (ko) | 2018-03-28 |
| WO2009105512A1 (en) | 2009-08-27 |
| EP2247561B1 (en) | 2014-03-26 |
| MX2010009080A (es) | 2010-09-07 |
| KR101842380B1 (ko) | 2018-03-26 |
| CA2713086A1 (en) | 2009-08-27 |
| BRPI0906014A2 (pt) | 2015-06-30 |
| EP2247561A1 (en) | 2010-11-10 |
| KR101946378B1 (ko) | 2019-02-12 |
| KR20190016124A (ko) | 2019-02-15 |
| JP2011513227A (ja) | 2011-04-28 |
| CN101952230B (zh) | 2015-07-22 |
| RU2010138783A (ru) | 2012-03-27 |
| KR20100138933A (ko) | 2010-12-31 |
| RU2476416C2 (ru) | 2013-02-27 |
| KR20160120804A (ko) | 2016-10-18 |
| CN101952230A (zh) | 2011-01-19 |
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