EP2976319A1 - Composition comprising hf and 3,3,3-trifluoropropene - Google Patents
Composition comprising hf and 3,3,3-trifluoropropeneInfo
- Publication number
- EP2976319A1 EP2976319A1 EP14711824.4A EP14711824A EP2976319A1 EP 2976319 A1 EP2976319 A1 EP 2976319A1 EP 14711824 A EP14711824 A EP 14711824A EP 2976319 A1 EP2976319 A1 EP 2976319A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- hfo
- hcfo
- chloro
- hfc
- trifluoropropene
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 89
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 title claims abstract description 41
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 43
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 43
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims abstract description 31
- SMCNZLDHTZESTK-UHFFFAOYSA-N 2-chloro-1,1,1,2-tetrafluoropropane Chemical compound CC(F)(Cl)C(F)(F)F SMCNZLDHTZESTK-UHFFFAOYSA-N 0.000 claims abstract description 28
- QAERDLQYXMEHEB-UHFFFAOYSA-N 1,1,3,3,3-pentafluoroprop-1-ene Chemical compound FC(F)=CC(F)(F)F QAERDLQYXMEHEB-UHFFFAOYSA-N 0.000 claims abstract description 20
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 claims abstract description 20
- FDOPVENYMZRARC-UHFFFAOYSA-N 1,1,1,2,2-pentafluoropropane Chemical compound CC(F)(F)C(F)(F)F FDOPVENYMZRARC-UHFFFAOYSA-N 0.000 claims abstract description 19
- HMAHQANPHFVLPT-UHFFFAOYSA-N 1,3,3-trifluoroprop-1-yne Chemical compound FC#CC(F)F HMAHQANPHFVLPT-UHFFFAOYSA-N 0.000 claims abstract description 19
- OQISUJXQFPPARX-UHFFFAOYSA-N 2-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Cl)=C OQISUJXQFPPARX-UHFFFAOYSA-N 0.000 claims abstract description 18
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 claims abstract description 17
- 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 claims abstract description 17
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 238000009835 boiling Methods 0.000 claims description 13
- 150000002894 organic compounds Chemical class 0.000 claims description 9
- -1 halocarbon compound Chemical class 0.000 claims description 7
- CDOOAUSHHFGWSA-UPHRSURJSA-N (z)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C/C(F)(F)F CDOOAUSHHFGWSA-UPHRSURJSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 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 claims description 3
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 claims 1
- 125000001145 hydrido group Chemical class *[H] 0.000 abstract 1
- 150000008282 halocarbons Chemical class 0.000 description 20
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- NEHMKBQYUWJMIP-UHFFFAOYSA-N anhydrous methyl chloride Natural products ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- INEMUVRCEAELBK-UHFFFAOYSA-N 1,1,1,2-tetrafluoropropane Chemical compound CC(F)C(F)(F)F INEMUVRCEAELBK-UHFFFAOYSA-N 0.000 description 4
- KDWQLICBSFIDRM-UHFFFAOYSA-N 1,1,1-trifluoropropane Chemical compound CCC(F)(F)F KDWQLICBSFIDRM-UHFFFAOYSA-N 0.000 description 4
- BLEZTPDKUBSTII-UHFFFAOYSA-N 1-chloro-1-fluoroprop-1-ene Chemical compound CC=C(F)Cl BLEZTPDKUBSTII-UHFFFAOYSA-N 0.000 description 4
- SBICOSJPCBAFED-UHFFFAOYSA-N 2-chloro-1,1-difluoroprop-1-ene Chemical compound CC(Cl)=C(F)F SBICOSJPCBAFED-UHFFFAOYSA-N 0.000 description 4
- XTRPJEPJFXGYCI-UHFFFAOYSA-N 3-chloro-1,1,1,2,2-pentafluoropropane Chemical compound FC(F)(F)C(F)(F)CCl XTRPJEPJFXGYCI-UHFFFAOYSA-N 0.000 description 4
- 238000010908 decantation Methods 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- MWDWMQNTNBHJEI-UHFFFAOYSA-N 1,1,2,3,3-pentafluoropropane Chemical compound FC(F)C(F)C(F)F MWDWMQNTNBHJEI-UHFFFAOYSA-N 0.000 description 3
- AYNJDIUGIVKMNZ-UHFFFAOYSA-N 1,1,2,3-tetrafluoropropane Chemical compound FCC(F)C(F)F AYNJDIUGIVKMNZ-UHFFFAOYSA-N 0.000 description 3
- BNYODXFAOQCIIO-UHFFFAOYSA-N 1,1,3,3-tetrafluoroprop-1-ene Chemical compound FC(F)C=C(F)F BNYODXFAOQCIIO-UHFFFAOYSA-N 0.000 description 3
- YHLIEGBCOUQKHU-UHFFFAOYSA-N 1,1-difluoroprop-1-ene Chemical compound CC=C(F)F YHLIEGBCOUQKHU-UHFFFAOYSA-N 0.000 description 3
- FFTOUVYEKNGDCM-UHFFFAOYSA-N 1,3,3-trifluoroprop-1-ene Chemical compound FC=CC(F)F FFTOUVYEKNGDCM-UHFFFAOYSA-N 0.000 description 3
- ATJSHGXKPLTCEG-UHFFFAOYSA-N 1-chloro-1,1-difluoropropane Chemical compound CCC(F)(F)Cl ATJSHGXKPLTCEG-UHFFFAOYSA-N 0.000 description 3
- LOCOMRPWMOCMPV-UHFFFAOYSA-N 2,3-dichloro-1,1,1,2-tetrafluoropropane Chemical compound FC(F)(F)C(F)(Cl)CCl LOCOMRPWMOCMPV-UHFFFAOYSA-N 0.000 description 3
- XPRPUIGRQWCMGD-UHFFFAOYSA-N 2,3-dichloro-1,1-difluoroprop-1-ene Chemical compound FC(F)=C(Cl)CCl XPRPUIGRQWCMGD-UHFFFAOYSA-N 0.000 description 3
- BKWAVXQSZLEURV-UHFFFAOYSA-N 2-chloro-1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)C(Cl)C(F)(F)F BKWAVXQSZLEURV-UHFFFAOYSA-N 0.000 description 3
- VRVIDSRWPUGFBU-UHFFFAOYSA-N 2-chloro-1,1,1-trifluoropropane Chemical compound CC(Cl)C(F)(F)F VRVIDSRWPUGFBU-UHFFFAOYSA-N 0.000 description 3
- COAUHYBSXMIJDK-UHFFFAOYSA-N 3,3-dichloro-1,1,1,2,2-pentafluoropropane Chemical compound FC(F)(F)C(F)(F)C(Cl)Cl COAUHYBSXMIJDK-UHFFFAOYSA-N 0.000 description 3
- IJTAKAGEJXIJPQ-UHFFFAOYSA-N 3-chloro-1,1,2,3,3-pentafluoroprop-1-ene Chemical compound FC(F)=C(F)C(F)(F)Cl IJTAKAGEJXIJPQ-UHFFFAOYSA-N 0.000 description 3
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 3
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- WFLOTYSKFUPZQB-OWOJBTEDSA-N (e)-1,2-difluoroethene Chemical group F\C=C\F WFLOTYSKFUPZQB-OWOJBTEDSA-N 0.000 description 2
- INPRTAFPJCUIBZ-OWOJBTEDSA-N (e)-1,3-difluoroprop-1-ene Chemical compound FC\C=C\F INPRTAFPJCUIBZ-OWOJBTEDSA-N 0.000 description 2
- 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 description 2
- ZDCWZRQSHBQRGN-UHFFFAOYSA-N 1,1,1,2,3-pentafluoropropane Chemical compound FCC(F)C(F)(F)F ZDCWZRQSHBQRGN-UHFFFAOYSA-N 0.000 description 2
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 2
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 2
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 2
- AWTOFSDLNREIFS-UHFFFAOYSA-N 1,1,2,2,3-pentafluoropropane Chemical compound FCC(F)(F)C(F)F AWTOFSDLNREIFS-UHFFFAOYSA-N 0.000 description 2
- NDMMKOCNFSTXRU-UHFFFAOYSA-N 1,1,2,3,3-pentafluoroprop-1-ene Chemical compound FC(F)C(F)=C(F)F NDMMKOCNFSTXRU-UHFFFAOYSA-N 0.000 description 2
- WGZYQOSEVSXDNI-UHFFFAOYSA-N 1,1,2-trifluoroethane Chemical compound FCC(F)F WGZYQOSEVSXDNI-UHFFFAOYSA-N 0.000 description 2
- LNGDLROYEAUMEQ-UHFFFAOYSA-N 1,1,2-trifluoroprop-1-ene Chemical compound CC(F)=C(F)F LNGDLROYEAUMEQ-UHFFFAOYSA-N 0.000 description 2
- JDLOJZBMTBIATO-UHFFFAOYSA-N 1,1,3,3-tetrafluoropropane Chemical compound FC(F)CC(F)F JDLOJZBMTBIATO-UHFFFAOYSA-N 0.000 description 2
- URZZGOOCQOQVOC-UHFFFAOYSA-N 1,1,3-trifluoroprop-1-ene Chemical compound FCC=C(F)F URZZGOOCQOQVOC-UHFFFAOYSA-N 0.000 description 2
- ITUYSFNEDBHHCL-UHFFFAOYSA-N 1,1-dichloro-1,2,3,3-tetrafluoropropane Chemical compound FC(F)C(F)C(F)(Cl)Cl ITUYSFNEDBHHCL-UHFFFAOYSA-N 0.000 description 2
- ISCYUDAHBJMFNT-UHFFFAOYSA-N 1,1-dichloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C(Cl)Cl ISCYUDAHBJMFNT-UHFFFAOYSA-N 0.000 description 2
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 2
- TXHNVFGQJAAUNB-UHFFFAOYSA-N 1,2,3-trifluoroprop-1-ene Chemical compound FCC(F)=CF TXHNVFGQJAAUNB-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- XXSZLFRJEKKBDJ-UHFFFAOYSA-N 1-chloro-1,1,2,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)Cl XXSZLFRJEKKBDJ-UHFFFAOYSA-N 0.000 description 2
- XDVGPJTXCYGVQM-UHFFFAOYSA-N 1-chloro-1,1,3-trifluoropropane Chemical compound FCCC(F)(F)Cl XDVGPJTXCYGVQM-UHFFFAOYSA-N 0.000 description 2
- BHNZEZWIUMJCGF-UHFFFAOYSA-N 1-chloro-1,1-difluoroethane Chemical compound CC(F)(F)Cl BHNZEZWIUMJCGF-UHFFFAOYSA-N 0.000 description 2
- BOUGCJDAQLKBQH-UHFFFAOYSA-N 1-chloro-1,2,2,2-tetrafluoroethane Chemical compound FC(Cl)C(F)(F)F BOUGCJDAQLKBQH-UHFFFAOYSA-N 0.000 description 2
- FGUQBEGFRUTZFO-UHFFFAOYSA-N 1-chloro-1,2,3-trifluoroprop-1-ene Chemical compound FCC(F)=C(F)Cl FGUQBEGFRUTZFO-UHFFFAOYSA-N 0.000 description 2
- SEXCLMKCCLUUKC-UHFFFAOYSA-N 1-chloro-1,3,3-trifluoroprop-1-ene Chemical compound FC(F)C=C(F)Cl SEXCLMKCCLUUKC-UHFFFAOYSA-N 0.000 description 2
- USCSECLOSDIOTA-UHFFFAOYSA-N 1-chloro-2,3,3-trifluoroprop-1-ene Chemical compound FC(F)C(F)=CCl USCSECLOSDIOTA-UHFFFAOYSA-N 0.000 description 2
- DCWQLZUJMHEDKD-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoropropane Chemical compound CC(Cl)(Cl)C(F)(F)F DCWQLZUJMHEDKD-UHFFFAOYSA-N 0.000 description 2
- JMRIJKGIVGYIAD-UHFFFAOYSA-N 2,3,3-trifluoroprop-1-ene Chemical compound FC(F)C(F)=C JMRIJKGIVGYIAD-UHFFFAOYSA-N 0.000 description 2
- CYXIKYKBLDZZNW-UHFFFAOYSA-N 2-Chloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)CCl CYXIKYKBLDZZNW-UHFFFAOYSA-N 0.000 description 2
- UZTWWVBZLLQHRB-UHFFFAOYSA-N 2-chloro-1,1,3-trifluoroprop-1-ene Chemical compound FCC(Cl)=C(F)F UZTWWVBZLLQHRB-UHFFFAOYSA-N 0.000 description 2
- IEFKUHVUFVKRMJ-UHFFFAOYSA-N 2-chloro-1,3,3-trifluoroprop-1-ene Chemical compound ClC(=CF)C(F)F IEFKUHVUFVKRMJ-UHFFFAOYSA-N 0.000 description 2
- PLTIOZOVDUUXDQ-UHFFFAOYSA-N 3,3-dichloro-1,1,1-trifluoropropane Chemical compound FC(F)(F)CC(Cl)Cl PLTIOZOVDUUXDQ-UHFFFAOYSA-N 0.000 description 2
- AWRHGKKFIUAKHZ-UHFFFAOYSA-N 3,3-dichloro-1,1,2,3-tetrafluoroprop-1-ene Chemical compound FC(F)=C(F)C(F)(Cl)Cl AWRHGKKFIUAKHZ-UHFFFAOYSA-N 0.000 description 2
- SLAYHOJJZUBYEK-UHFFFAOYSA-N 3,3-dichloro-1,3-difluoroprop-1-ene Chemical compound FC=CC(F)(Cl)Cl SLAYHOJJZUBYEK-UHFFFAOYSA-N 0.000 description 2
- ZPIFKCVYZBVZIV-UHFFFAOYSA-N 3-chloro-1,1,1-trifluoropropane Chemical compound FC(F)(F)CCCl ZPIFKCVYZBVZIV-UHFFFAOYSA-N 0.000 description 2
- HXNJCCYKKHPFIO-UHFFFAOYSA-N 3-chloro-1,1,2,3-tetrafluoroprop-1-ene Chemical compound FC(Cl)C(F)=C(F)F HXNJCCYKKHPFIO-UHFFFAOYSA-N 0.000 description 2
- HLKBDWUYTHOCIJ-UHFFFAOYSA-N 3-chloro-1,1,2-trifluoroprop-1-ene Chemical compound FC(F)=C(F)CCl HLKBDWUYTHOCIJ-UHFFFAOYSA-N 0.000 description 2
- FFIDRWZHRKKSAS-UHFFFAOYSA-N 3-chloro-1,1,3-trifluoroprop-1-ene Chemical compound FC(Cl)C=C(F)F FFIDRWZHRKKSAS-UHFFFAOYSA-N 0.000 description 2
- UAHVVXPNJLRMPX-UHFFFAOYSA-N 3-chloro-1,2,3-trifluoroprop-1-ene Chemical compound FC=C(F)C(F)Cl UAHVVXPNJLRMPX-UHFFFAOYSA-N 0.000 description 2
- VTOPKRLXDFCFGJ-UHFFFAOYSA-N 3-chloro-2,3,3-trifluoroprop-1-ene Chemical compound FC(=C)C(F)(F)Cl VTOPKRLXDFCFGJ-UHFFFAOYSA-N 0.000 description 2
- DASQIKOOFDJYKA-UHFFFAOYSA-N CCIF Chemical compound CCIF DASQIKOOFDJYKA-UHFFFAOYSA-N 0.000 description 2
- 239000004340 Chloropentafluoroethane Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 235000019406 chloropentafluoroethane Nutrition 0.000 description 2
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical group FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 2
- UKACHOXRXFQJFN-UHFFFAOYSA-N heptafluoropropane Chemical compound FC(F)C(F)(F)C(F)(F)F UKACHOXRXFQJFN-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 description 2
- 229960004065 perflutren Drugs 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- DMUPYMORYHFFCT-OWOJBTEDSA-N (e)-1,2,3,3,3-pentafluoroprop-1-ene Chemical compound F\C=C(\F)C(F)(F)F DMUPYMORYHFFCT-OWOJBTEDSA-N 0.000 description 1
- PNWJILFKWURCIR-UPHRSURJSA-N (e)-1-chloro-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C(Cl)=C/C(F)(F)F PNWJILFKWURCIR-UPHRSURJSA-N 0.000 description 1
- ZUAQTIHDWIHCSV-UPHRSURJSA-N (z)-1,2,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C(/F)C(F)F ZUAQTIHDWIHCSV-UPHRSURJSA-N 0.000 description 1
- ZHJBJVPTRJNNIK-UPHRSURJSA-N (z)-1,2-dichloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(\Cl)=C\Cl ZHJBJVPTRJNNIK-UPHRSURJSA-N 0.000 description 1
- LDTMPQQAWUMPKS-UPHRSURJSA-N (z)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C/Cl LDTMPQQAWUMPKS-UPHRSURJSA-N 0.000 description 1
- 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 1
- 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 description 1
- 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 1
- PFFGXVGPSGJOBV-UHFFFAOYSA-N 1,1,1,3-tetrafluoropropane Chemical compound FCCC(F)(F)F PFFGXVGPSGJOBV-UHFFFAOYSA-N 0.000 description 1
- ZXVZGGVDYOBILI-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoropropane Chemical compound FC(F)C(F)(F)C(F)F ZXVZGGVDYOBILI-UHFFFAOYSA-N 0.000 description 1
- WXGNWUVNYMJENI-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)F WXGNWUVNYMJENI-UHFFFAOYSA-N 0.000 description 1
- XWUSALIIUZARQE-UHFFFAOYSA-N 1,1,2,2-tetrafluoropropane Chemical compound CC(F)(F)C(F)F XWUSALIIUZARQE-UHFFFAOYSA-N 0.000 description 1
- PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical compound FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 description 1
- HHRQYHKSSIGXJV-UHFFFAOYSA-N 1,1,2-trifluoropropane Chemical compound CC(F)C(F)F HHRQYHKSSIGXJV-UHFFFAOYSA-N 0.000 description 1
- GQSMEOJGQJMOHA-UHFFFAOYSA-N 1,1,3-trifluoropropane Chemical compound FCCC(F)F GQSMEOJGQJMOHA-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- FMKLGBFKHKIUKZ-UHFFFAOYSA-N 1,1-dichloro-1,2,2,3,3,3-hexafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(Cl)Cl FMKLGBFKHKIUKZ-UHFFFAOYSA-N 0.000 description 1
- VOOXKKSIKFHMTJ-UHFFFAOYSA-N 1,1-dichloro-1,2,2-trifluoropropane Chemical compound CC(F)(F)C(F)(Cl)Cl VOOXKKSIKFHMTJ-UHFFFAOYSA-N 0.000 description 1
- YERASKROMPMIBM-UHFFFAOYSA-N 1,1-dichloro-1,2,3,3,3-pentafluoropropane Chemical compound FC(F)(F)C(F)C(F)(Cl)Cl YERASKROMPMIBM-UHFFFAOYSA-N 0.000 description 1
- LQJXGJWGNXVENX-UHFFFAOYSA-N 1,1-dichloro-1,2,3-trifluoropropane Chemical compound FCC(F)C(F)(Cl)Cl LQJXGJWGNXVENX-UHFFFAOYSA-N 0.000 description 1
- JBSUEXFKGWKQFC-UHFFFAOYSA-N 1,1-dichloro-1,3,3,3-tetrafluoropropane Chemical compound FC(F)(F)CC(F)(Cl)Cl JBSUEXFKGWKQFC-UHFFFAOYSA-N 0.000 description 1
- DAVKAFRSHGCHSH-UHFFFAOYSA-N 1,1-dichloro-1,3,3-trifluoropropane Chemical compound FC(F)CC(F)(Cl)Cl DAVKAFRSHGCHSH-UHFFFAOYSA-N 0.000 description 1
- GELJRWJPYZKUPR-UHFFFAOYSA-N 1,1-dichloro-2,2,3-trifluoropropane Chemical compound FCC(F)(F)C(Cl)Cl GELJRWJPYZKUPR-UHFFFAOYSA-N 0.000 description 1
- QGYLHZMNVGBXDQ-UHFFFAOYSA-N 1,1-dichloro-2,3,3,3-tetrafluoroprop-1-ene Chemical compound ClC(Cl)=C(F)C(F)(F)F QGYLHZMNVGBXDQ-UHFFFAOYSA-N 0.000 description 1
- DSKXWQYJAQZRHW-UHFFFAOYSA-N 1,1-dichloro-2,3,3-trifluoroprop-1-ene Chemical compound FC(F)C(F)=C(Cl)Cl DSKXWQYJAQZRHW-UHFFFAOYSA-N 0.000 description 1
- MBGGDBNQMJYEBF-UHFFFAOYSA-N 1,1-dichloro-2,3-difluoroprop-1-ene Chemical compound FCC(F)=C(Cl)Cl MBGGDBNQMJYEBF-UHFFFAOYSA-N 0.000 description 1
- WZBFBGLQXCGMFG-UHFFFAOYSA-N 1,1-dichloro-3,3-difluoroprop-1-ene Chemical compound FC(F)C=C(Cl)Cl WZBFBGLQXCGMFG-UHFFFAOYSA-N 0.000 description 1
- DONSGGANNRCHDL-UHFFFAOYSA-N 1,2,2-trifluoropropane Chemical compound CC(F)(F)CF DONSGGANNRCHDL-UHFFFAOYSA-N 0.000 description 1
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- DPCCJAXLIOFIFF-UHFFFAOYSA-N 3-chloro-1,2-difluoroprop-1-ene Chemical compound ClCC(=CF)F DPCCJAXLIOFIFF-UHFFFAOYSA-N 0.000 description 1
- FSZWJXAHNJBOAW-UHFFFAOYSA-N 3-chloro-1,3,3-trifluoroprop-1-ene Chemical compound FC=CC(F)(F)Cl FSZWJXAHNJBOAW-UHFFFAOYSA-N 0.000 description 1
- ARNCZNGVHUUPIX-UHFFFAOYSA-N 3-chloro-1,3-difluoroprop-1-ene Chemical compound ClC(C=CF)F ARNCZNGVHUUPIX-UHFFFAOYSA-N 0.000 description 1
- NXRVIYWUCXPXLM-UHFFFAOYSA-N 3-chloro-1-fluoroprop-1-ene Chemical compound FC=CCCl NXRVIYWUCXPXLM-UHFFFAOYSA-N 0.000 description 1
- UWZSCAKKXYDSJZ-UHFFFAOYSA-N 3-chloro-2,3-difluoroprop-1-ene Chemical compound FC(Cl)C(F)=C UWZSCAKKXYDSJZ-UHFFFAOYSA-N 0.000 description 1
- OOFDLUQVLPGWMM-UHFFFAOYSA-N 3-chloro-2-fluoroprop-1-ene Chemical compound FC(=C)CCl OOFDLUQVLPGWMM-UHFFFAOYSA-N 0.000 description 1
- AQBMNBSTXOCKKZ-UHFFFAOYSA-N 3-chloro-3,3-difluoroprop-1-ene Chemical compound FC(F)(Cl)C=C AQBMNBSTXOCKKZ-UHFFFAOYSA-N 0.000 description 1
- OUYIACQXDKRNFZ-UHFFFAOYSA-N 3-chloro-3-fluoroprop-1-ene Chemical compound FC(Cl)C=C OUYIACQXDKRNFZ-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- YKLNYHDKMLSDSA-ODZAUARKSA-N FC(C#C)(F)F.FC(\C=C/Cl)(F)F Chemical compound FC(C#C)(F)F.FC(\C=C/Cl)(F)F YKLNYHDKMLSDSA-ODZAUARKSA-N 0.000 description 1
- IDYFBRKPOSDRGG-UHFFFAOYSA-N FC=C(C(F)F)F.FC(=C(CF)F)F Chemical compound FC=C(C(F)F)F.FC(=C(CF)F)F IDYFBRKPOSDRGG-UHFFFAOYSA-N 0.000 description 1
- 239000003082 abrasive agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000013529 heat transfer fluid Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000001577 simple distillation Methods 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/30—Materials not provided for elsewhere for aerosols
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
- C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
Definitions
- the present invention relates to azeotropic or quasi-azeotropic compositions comprising 3,3,3-trifluoropropene and hydrogen fluoride. These compositions may be derived from intermediate 3,3,3-trifluoropropene production compositions and are generally useful in hydrogen fluoride recycle processes.
- Fluids based on 3,3,3-trifluoropropene have found many applications in various industrial fields, including heat transfer fluid, propellants, foaming agents, blowing agents, gaseous dielectrics, polymerization medium or monomer, carrier fluids, abrasive agents, drying agents and power generating unit fluids.
- the present invention relates to an azeotropic or quasi-azeotropic composition
- an azeotropic or quasi-azeotropic composition comprising hydrogen fluoride, 3,3,3-trifluoropropene, and one or more compound (s) (hydro) halocarbon (s) comprising between 1 and 3 atom (s) carbon.
- the composition is heteroazeotropic or quasi-heteroazeotropic.
- a hetero-azeotropic or quasi-heteroazeotropic mixture is an azeotropic or quasi-azeotropic mixture of which the condensed liquid forms two immiscible solutions which can be easily separated, for example by decantation.
- quadsi-azeotropic or “quasi-hetero-azeotropic” has a broad meaning and is intended to include compositions that are strictly azeotropic or strictly heteroazeotropic and those that behave as an azeotropic or heteroazeotropic mixture.
- a mixture is azeotropic when the pressure at the dew point is equal to that at the bubble-forming point, which means that the vapor composition is equal to that of the condensed liquid.
- a mixture is considered quasi-azeotropic when the dew point pressure is substantially equal to that at the bubble-forming point, which means that the vapor composition is substantially equal to that of the condensed liquid.
- compositions according to the invention relate in particular to the following compounds whose acronyms represent:
- HCFC-1 15 chloropentafluoroethane, or C 2 F 5 CI
- HFC-125 pentafluoroethane, or C 2 HF 5
- HCFC-133a 1-chloro-2,2,2-trifluoroethane, or C 2 H 2 F 3 CI
- HCFC-142b 1-chloro-1,1-difluoroethane, or C 2 H 3 F 2 CI
- - HFO-1 132 1, 2-difluoroethylene, or C 2 H 2 F 2
- HFO-1 252 difluoropropene, or C 3 H 4 F 2
- HCFC-235 chloropentafluoropropane, or C 3 H 2 F 5
- CI HFC-236 hexafluoropropane, or C 3 H 2 F 6
- HCFC-244 chlorotetrafluoropropane, or C 3 H 3 F 4 CI
- HCFC-244bb 2-chloro, 1, 1, 1, 2-tetrafluoropropane or CF 3 -CFCI-CH 3 - HFC-245fa: 1, 1, 1, 3,3-pentafluoropropane or CF 3 -CH 2 -CHF 2
- HCFC-253 chlorotrifluoropropane, or C 3 H 4 F 3 CI
- HFC-263 trifluoropropane, or C 3 H 5 F 3
- composition according to the invention may optionally be a mixture of one or more azeotropic and / or heteroazeotropic ternary, quaternary, pentane, six-compound system, seven-compound system , eight-component system or higher.
- the compound (s) with 1 and / or 2 carbon atom (s) may be chosen in particular from chloromethane, chloropentafluoroethane, 1-chloro-1, 2,2,2-tetrafluoroethane. , 1-chloro-1,1,2,2-tetrafluoroethane, pentafluoroethane, 1-chloro-1,2,2-trifluoroethane, 1-chloro-2,2,2-trifluoroethane, 1, 1, 2,2-tetrafluoroethane, 1,1,1,2-tetrafluoroethane, 1-chloro-1,2-difluoroethane, 1-chloro-1,1-difluoroethane, 1,1,2-trifluoroethane, 1 1,1,1-Trifluoroethane, 1,1,2-trifluoroethane, 1,1-difluoroethane, 1,2-difluoroethylene and fluoroethylene.
- the compound (s) having 3 carbon atoms may be chosen in particular from 1, 2-dichloro-1, 1, 2,3,3,3-hexafluoropropane, 1,3-dichloro 1, 1, 2,2,3,3-hexafluoropropane, 1,1-dichloro-1, 2,2,3,3,3-hexafluoropropane, 2,2-dichloro-1,1,1,3 , 3,3-Hexafluoropropane, 1-chloro-1,1,2,2,3,3,3-heptafluoropropane, 2-chloro-1,1,1,2,3,3,3-heptafluoropropane, octafluoropropane , dichloropentafluoropropane, 2,2-dichloro-1,1,1,3,3-pentafluoropropane, 2,3-dichloro-1,1,1,2,3-pentafluoropropane, 1,2-dichloro-1 , 1, 2,3,3-pentafluoro
- the present invention also relates to an azeotropic or quasi-azeotropic composition
- an azeotropic or quasi-azeotropic composition comprising hydrogen fluoride, 3,3,3-trifluoropropene, and one or more compound (s) chosen from 1, 1, 1, 2,2-pentafluoropropane, 2,3,3,3-tetrafluoropropene, E-3,3,3-trifluoro-1-chloropropene, 3,3,3-trifluoro-2-chloropropene, 1,3 3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2- chloro, 1, 1, 1, 2-tetrafluoropropane.
- compound (s) chosen from 1, 1, 1, 2,2-pentafluoropropane, 2,3,3,3-tetraflu
- the present invention further relates to a composition
- a composition comprising hydrogen fluoride, 3,3,3-trifluoropropene and at least one or more organic compound (s) selected from E-1, 3,3, 3-tetrafluoropropene, Z-1, 3,3,3-tetrafluoropropene, 3,3,3-trifluoro-2-chloropropene, E-3,3,3-trifluoro-1-chloropropene, 1, 1, 1,2,2-pentafluoropropane and 2,3,3,3-tetrafluoropropene.
- organic compound selected from E-1, 3,3, 3-tetrafluoropropene, Z-1, 3,3,3-tetrafluoropropene, 3,3,3-trifluoro-2-chloropropene, E-3,3,3-trifluoro-1-chloropropene, 1, 1, 1,2,2-pentafluoropropane and 2,3,3,3-tetrafluoropropene.
- the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, 1,1,1,2,2-pentafluoropropane and optionally one or more compound (s) chosen from 2,3,3,3-tetrafluoropropene, E-3,3,3-trifluoro-1-chloropropene, 3,3,3-trifluoro-2- chloropropene, 1,3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2, 3-pentafluoropropene and 2-chloro-1, 1, 1, 2-tetrafluoropropane.
- compound (s) chosen from 2,3,3,3-tetrafluoropropene, E-3,3,3-trifluoro-1-chloropropene, 3,3,3-trifluoro-2- chloropropene, 1,3,3,3-t
- the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, 2,3,3,3-tetrafluoropropene and optionally one or more compound (s) chosen ( s) from E-3,3,3-trifluoro-1-chloropropene, 3,3,3-trifluoro-2-chloropropene, 1,3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1 3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
- the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, E-3,3,3-trifluoro-1-chloropropene and optionally one or more compounds (s) chosen from 3,3,3-trifluoro-2-chloropropene, 1, 3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1, 1, 1, 3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
- the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, 3,3,3-trifluoro-2-chloropropene and optionally one or more compound ( s) selected from 1, 3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,3,3-pentafluoropropane, 1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
- compound ( s) selected from 1, 3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,3,3-pentafluoropropane, 1,2,3-pentafluoropropene and 2-
- the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, 1, 3,3,3-tetrafluoropropene and optionally one or more compound (s) chosen (s). ) from trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro-1, 1, 1, 2-tetrafluoropropane.
- the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, trifluoropropyne and optionally one or more compound (s) chosen from 1, 1 1,1,3,3-Pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
- the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, 1,1,1,3,3-pentafluoropropane and optionally one or more compound (s). ) selected from the 1, 1, 1, 3,3- pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
- the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, 1,1,1,3,3-pentafluoropropene and optionally one or more compound ( s) selected from 1, 1, 1, 2,3-pentafluoropropene and 2-chloro-1, 1, 1, 2-tetrafluoropropane.
- the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, 1,1,1,2,3-pentafluoropropene and optionally 2-chloro-1 , 1, 1, 2-tetrafluoropropane.
- the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
- the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, E-1, 3,3,3-tetrafluoropropene and optionally one or more compound (s) selected from Z-1, 3,3,3-tetrafluoropropene, 3,3,3-trifluoro-2-chloropropene, E-3,3,3-trifluoro-1-chloropropene, 1, 1 1,2,3-pentafluoropropane, 2,3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1, 1, 1, 2,3-pentafluoropropene and 2-chloro, 1, 1, 1, 2-tetrafluoropropane.
- the composition comprises hydrogen fluoride, 3,3,3-trifluoropropene, Z-1, 3,3,3-tetrafluoropropene and optionally one or more compound (s) ) selected from 3,3,3-trifluoro-2-chloropropene, E-3,3,3-trifluoro-1-chloropropene, 1,1,1,2,2-pentafluoropropane, 2, 3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro, 1, 1, 1, 2-tetrafluoropropane.
- compound (s) ) selected from 3,3,3-trifluoro-2-chloropropene, E-3,3,3-trifluoro-1-chloropropene, 1,1,1,2,2-pentafluoropropane, 2,
- the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, 3,3,3-trifluoro-2-chloropropene and optionally one or more compound ( s) selected from E-3,3,3-trifluoro-1-chloropropene, 1,1,1,2,2-pentafluoropropane, 2,3,3,3-tetrafluoropropene, trifluoropropyne, 1, 1, 1, 3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro, 1, 1, 1, 2 tetrafluoropropane.
- compound ( s) selected from E-3,3,3-trifluoro-1-chloropropene, 1,1,1,2,2-pentafluoropropane, 2,3,3,3-tetrafluoropropene, trifluoropropyne, 1, 1, 1, 3,3-pent
- the composition comprises hydrogen fluoride, 3,3,3-trifluoropropene, E-3,3,3-trifluoro-1-chloropropene and optionally one or more compound (s). ) chosen from 1, 1, 1, 2,2- pentafluoropropane, 2,3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2 , 3-pentafluoropropene and 2-chloro, 1, 1, 1, 2-tetrafluoropropane.
- compound (s) chosen from 1, 1, 1, 2,2- pentafluoropropane, 2,3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2 , 3-pentafluoropropene
- the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, 1,1,1,2,2-pentafluoropropane and optionally one or more compound (s) selected from 2,3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1, 1, 1,2,3-pentafluoropropene and 2-chloro, 1,1,1,2-tetrafluoropropane.
- the composition comprises hydrogen fluoride, 3,3,3-trifluoropropene, 2,3,3,3-tetrafluoropropene and optionally one or more compound (s) chosen (s) among trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro , 1, 1, 1, 2-tetrafluoropropane.
- the composition preferably comprises from 1 to 95%, and advantageously from 5 to 80% by weight of hydrogen fluoride and from 99 to 5%, and advantageously from 20 to 95% by weight. of the sum of the organic compounds, more particularly the composition comprises from 1 to 85% by weight of hydrogen fluoride and from 99 to 15% by weight of the sum of the organic compounds (HFO-1243zf and the (hydro) halocarbon compounds) .
- the boiling point of the composition according to the invention is between -20 ' ⁇ and 80' ⁇ , and at a pressure between 0.1 and 44 bar absolute, preferably between 0 ' ⁇ and 40 ' ⁇ and preferably at a pressure of between 0.7 and 18 bar absolute, advantageously between 0.9 and 12.5 absolute bar.
- compositions according to the invention have advantageous properties, in particular for the recycling of HF at the reaction stage.
- the condensed phase of these compositions optionally when they are subjected to a distillation step and / or a liquid / liquid separation step, such as by decantation, form two immiscible liquid phases.
- These beaches Decantation as a function of the HF content in the compositions was characterized for at least isotherms at 0 ° C, 25 ° C and 40 ° C.
- I, 1, 1, 2,3-pentafluoropropene and 2-chloro, 1, 1, 1, 2-tetrafluoropropane are characterized by a HF-depleted phase and an HF-enriched phase for at least 0 ° C isotherms, 25 ° C and 40 ° C.
- a preferred azeotropic or quasi-azeotropic composition according to the invention comprises from 1 to 85% by weight of hydrogen fluoride, and from 99 to 15% by weight of the sum of HFO-1243zf and HFC-245cb, the point d
- the boiling point of this preferred composition is from 0 to 40 ° C at a pressure of from 0.9 to 11.6 bar absolute.
- a preferred azeotropic or quasi-azeotropic composition according to the invention preferably comprises from 5 to 80% by weight of hydrogen fluoride and from 95 to 20% by weight of the sum of HFO-1243zf and HFC-245cb. boiling point of this preferred composition is between 0 and 40 ° C at a pressure of between 0.9 and
- a preferred azeotropic or quasi-azeotropic composition according to the invention comprises from 1 to 85% by weight of hydrogen fluoride, and from 99 to 15% by weight of the sum of HFO-1243zf, HCFC-244bb, HFC- 245fa, trifluoropropyne, HFO-1225yeZ and HFO-1225zc, the boiling point of this preferred composition is between 0 and 40 ⁇ at a pressure between 0.7 and 18 bar absolute.
- a preferred azeotropic or quasi-azeotropic composition according to the invention preferably comprises from 5 to 80% by weight of hydrogen fluoride, and from 95 to 20% by weight of the sum of HFO-1243zf, HCFC-244bb, HFC-245fa, trifluoropropyne, HFO-1225yeZ and HFO-1225zc, the boiling point of this preferred composition is between 0 and 40 ° C at a pressure between 0.7 and 18 bar absolute.
- Examples 2, 5, 8, 11, 14, 17 and 20 represent the boiling and pressure ranges of the mixtures and Examples 3, 6, 9, 12, 15, 18 and 21 represent the settling ranges.
- the settling ranges of Examples 3, 6, 9, 12, 15, 18 and 21 are calculated for mixtures of organic compounds having equimassic contents.
- a ternary mixture a mixture containing 50% by weight of each of the two organic compounds is considered; for a pentane mixture, a mixture containing 25% by weight of each of the four organic compounds is considered, the mass fraction of HF ranging from 0 to 1.
- Example 1 Ternary mixtures, isothermal at 25 ° C.
- Example 4 Quaternary mixtures, isothermal at 25 ° C.
- Example 5 Temperature and pressure range of quaternary mixtures
- Example 7 Pentane mixtures, isothermal at 25 ° C.
- Example 13 Seven-compound systems, isothermal at 25 ° C.
- Example 17 Temperature and pressure range of 8 compound system
- Example 19 13 HF Systems - HFO-1234yf - HFC-245cb - HCFO-1233xf - HCFO-1233zdE - HFO-1234zeE - HFO-1234zeZ - HFC-1243zf - HCFC-244bb - TFP - HFC-245fa - HFO-1225yeZ -
- Example 20 Temperature and pressure range of 13 compound system
Abstract
Description
Claims
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FR1352486A FR3003567B1 (en) | 2013-03-20 | 2013-03-20 | COMPOSITION COMPRISING HF AND 3,3,3-TRIFLUOROPROPENE |
PCT/FR2014/050371 WO2014147314A1 (en) | 2013-03-20 | 2014-02-24 | Composition comprising hf and 3,3,3-trifluoropropene |
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EP2976319A1 true EP2976319A1 (en) | 2016-01-27 |
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EP14711824.4A Pending EP2976319A1 (en) | 2013-03-20 | 2014-02-24 | Composition comprising hf and 3,3,3-trifluoropropene |
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US (1) | US10550054B2 (en) |
EP (1) | EP2976319A1 (en) |
JP (1) | JP6373356B2 (en) |
CN (1) | CN105050990A (en) |
FR (1) | FR3003567B1 (en) |
WO (1) | WO2014147314A1 (en) |
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FR2937328B1 (en) | 2008-10-16 | 2010-11-12 | Arkema France | HEAT TRANSFER METHOD |
FR3003565B1 (en) * | 2013-03-20 | 2018-06-29 | Arkema France | COMPOSITION COMPRISING HF AND 2,3,3,3-TETRAFLUOROPROPENE |
FR3003567B1 (en) | 2013-03-20 | 2015-03-06 | Arkema France | COMPOSITION COMPRISING HF AND 3,3,3-TRIFLUOROPROPENE |
FR3003566B1 (en) * | 2013-03-20 | 2018-07-06 | Arkema France | COMPOSITION COMPRISING HF AND E-3,3,3-TRIFLUORO-1-CHLOROPROPENE |
FR3003569B1 (en) * | 2013-03-20 | 2015-12-25 | Arkema France | COMPOSITION COMPRISING HF AND 1,3,3,3-TETRAFLUOROPROPENE |
JP6213194B2 (en) | 2013-11-29 | 2017-10-18 | セントラル硝子株式会社 | Method for converting thermal energy into mechanical energy, organic Rankine cycle device, and method for replacing working fluid |
FR3015478B1 (en) * | 2013-12-19 | 2015-12-25 | Arkema France | AZEOTROPIC COMPOSITIONS BASED ON HYDROGEN FLUORIDE AND Z-3,3,3-TRIFLUORO-1-CHLOROPROPENE |
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US10550054B2 (en) | 2020-02-04 |
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FR3003567B1 (en) | 2015-03-06 |
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CN105050990A (en) | 2015-11-11 |
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