CN104987277A - 含有至少一种含氢氟烷和氟化氢的混合物的分离方法,含氢氟烷的制备方法和共沸组合物 - Google Patents
含有至少一种含氢氟烷和氟化氢的混合物的分离方法,含氢氟烷的制备方法和共沸组合物 Download PDFInfo
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- CN104987277A CN104987277A CN201510305450.6A CN201510305450A CN104987277A CN 104987277 A CN104987277 A CN 104987277A CN 201510305450 A CN201510305450 A CN 201510305450A CN 104987277 A CN104987277 A CN 104987277A
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- Prior art keywords
- hydrofluoroalkane
- mixture
- hydrogen fluoride
- reaction
- precursor
- 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
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- 150000005828 hydrofluoroalkanes Chemical class 0.000 title claims abstract description 152
- 239000000203 mixture Substances 0.000 title claims abstract description 123
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 title claims abstract description 83
- 229910000040 hydrogen fluoride Inorganic materials 0.000 title claims abstract description 83
- 238000000034 method Methods 0.000 title claims abstract description 68
- 239000002243 precursor Substances 0.000 claims abstract description 84
- 238000000926 separation method Methods 0.000 claims abstract description 47
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 33
- 238000002360 preparation method Methods 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims description 78
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical compound [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 claims description 49
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 37
- 150000002894 organic compounds Chemical class 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- 239000007791 liquid phase Substances 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 17
- 239000007795 chemical reaction product Substances 0.000 claims description 15
- FFBFEBDZFWMXBE-UHFFFAOYSA-N 1,1,1,3,3-pentachlorobutane Chemical compound CC(Cl)(Cl)CC(Cl)(Cl)Cl FFBFEBDZFWMXBE-UHFFFAOYSA-N 0.000 claims description 12
- NJCQVAKYBOCUCS-UHFFFAOYSA-N [C].F Chemical compound [C].F NJCQVAKYBOCUCS-UHFFFAOYSA-N 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical group FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- 150000003609 titanium compounds Chemical class 0.000 claims description 4
- MRKAIYYTIQVWCK-UHFFFAOYSA-N 1,1-dichloro-1,3,3-trifluorobutane Chemical compound CC(F)(F)CC(F)(Cl)Cl MRKAIYYTIQVWCK-UHFFFAOYSA-N 0.000 claims description 3
- JZKJJRVPJFNKMB-UHFFFAOYSA-N 1,3-dichloro-1,1,3-trifluorobutane Chemical compound CC(F)(Cl)CC(F)(F)Cl JZKJJRVPJFNKMB-UHFFFAOYSA-N 0.000 claims description 3
- 239000001273 butane Substances 0.000 claims description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 3
- HFZJRXWWTAKJAO-UHFFFAOYSA-N 3,3-dichloro-1,1,1-trifluorobutane Chemical compound CC(Cl)(Cl)CC(F)(F)F HFZJRXWWTAKJAO-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
- 150000001805 chlorine compounds Chemical group 0.000 claims 2
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims 1
- VAOMKNAMFFGULC-UHFFFAOYSA-N 2,3-dichloro-1,1,1-trifluorobutane Chemical compound FC(C(C(C)Cl)Cl)(F)F VAOMKNAMFFGULC-UHFFFAOYSA-N 0.000 claims 1
- 238000004821 distillation Methods 0.000 description 24
- 239000012535 impurity Substances 0.000 description 14
- 238000009835 boiling Methods 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- 230000009466 transformation Effects 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 239000000376 reactant Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 6
- -1 carbon atom hydrofluoroalkane Chemical class 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 229910001512 metal fluoride Inorganic materials 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- 150000003608 titanium Chemical class 0.000 description 3
- RIQRGMUSBYGDBL-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,5-decafluoropentane Chemical compound FC(F)(F)C(F)C(F)C(F)(F)C(F)(F)F RIQRGMUSBYGDBL-UHFFFAOYSA-N 0.000 description 2
- 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 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
- CXIGIYYQHHRBJC-UHFFFAOYSA-N 1,1,1,4,4,4-hexafluorobutane Chemical compound FC(F)(F)CCC(F)(F)F CXIGIYYQHHRBJC-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
- XPAUQCAVYXOWFR-UHFFFAOYSA-N 1,1-dichloro-1,3-difluorobut-2-ene Chemical compound CC(F)=CC(F)(Cl)Cl XPAUQCAVYXOWFR-UHFFFAOYSA-N 0.000 description 2
- BSERHUYXVAIRSG-UHFFFAOYSA-N 1-chloro-1,1,3,3-tetrafluorobutane Chemical compound CC(F)(F)CC(F)(F)Cl BSERHUYXVAIRSG-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- LZOUTMTXULWVSU-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptachloropropane Chemical compound ClC(Cl)(Cl)C(Cl)C(Cl)(Cl)Cl LZOUTMTXULWVSU-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
- ZXPCCXXSNUIVNK-UHFFFAOYSA-N 1,1,1,2,3-pentachloropropane Chemical compound ClCC(Cl)C(Cl)(Cl)Cl ZXPCCXXSNUIVNK-UHFFFAOYSA-N 0.000 description 1
- BBEAZDGZMVABIC-UHFFFAOYSA-N 1,1,1,3,3,3-hexachloropropane Chemical compound ClC(Cl)(Cl)CC(Cl)(Cl)Cl BBEAZDGZMVABIC-UHFFFAOYSA-N 0.000 description 1
- GMWOFVVPEWUYMH-UHFFFAOYSA-N 1,1,1,3,3-pentachloro-2-methylpropane Chemical compound ClC(Cl)C(C)C(Cl)(Cl)Cl GMWOFVVPEWUYMH-UHFFFAOYSA-N 0.000 description 1
- VVWFZKBKXPXGBH-UHFFFAOYSA-N 1,1,1,3,3-pentachloropropane Chemical compound ClC(Cl)CC(Cl)(Cl)Cl VVWFZKBKXPXGBH-UHFFFAOYSA-N 0.000 description 1
- HCCXTSAGOJXOJG-UHFFFAOYSA-N 1,1,1,3-tetrachloro-3-fluorobutane Chemical compound CC(F)(Cl)CC(Cl)(Cl)Cl HCCXTSAGOJXOJG-UHFFFAOYSA-N 0.000 description 1
- IZPMJFLFAHTFRK-UHFFFAOYSA-N 1,1,1-trichloro-3,3-difluorobutane Chemical compound CC(F)(F)CC(Cl)(Cl)Cl IZPMJFLFAHTFRK-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- IYFMQUDCYNWFTL-UHFFFAOYSA-N 1,1,2,2,3-pentachloropropane Chemical compound ClCC(Cl)(Cl)C(Cl)Cl IYFMQUDCYNWFTL-UHFFFAOYSA-N 0.000 description 1
- XHDSPHHDGAQIDF-UHFFFAOYSA-N 1,1,3,3-tetrachloro-1-fluorobutane Chemical compound CC(Cl)(Cl)CC(F)(Cl)Cl XHDSPHHDGAQIDF-UHFFFAOYSA-N 0.000 description 1
- XQVOZHXFNGMERA-UHFFFAOYSA-N 1,1,3-trichloro-1,3-difluorobutane Chemical compound CC(F)(Cl)CC(F)(Cl)Cl XQVOZHXFNGMERA-UHFFFAOYSA-N 0.000 description 1
- LBXIVYAXNJZIAE-UHFFFAOYSA-N 1,1,3-trifluorobut-2-ene Chemical compound CC(F)=CC(F)F LBXIVYAXNJZIAE-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- RMDJNEOJTZWCJE-UHFFFAOYSA-N 1,3,3-trichloro-1,1-difluorobutane Chemical compound CC(Cl)(Cl)CC(F)(F)Cl RMDJNEOJTZWCJE-UHFFFAOYSA-N 0.000 description 1
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
- WGCJTTUVWKJDAX-UHFFFAOYSA-N 1-fluoro-2-methylpropane Chemical compound CC(C)CF WGCJTTUVWKJDAX-UHFFFAOYSA-N 0.000 description 1
- BNUSKMGXRXIWAF-UHFFFAOYSA-N 3-chloro-1,1,1,3-tetrafluorobutane Chemical compound CC(F)(Cl)CC(F)(F)F BNUSKMGXRXIWAF-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- QBTUCBKAWGUMMK-UHFFFAOYSA-N C=CC.[F] Chemical group C=CC.[F] QBTUCBKAWGUMMK-UHFFFAOYSA-N 0.000 description 1
- XWCDCDSDNJVCLO-UHFFFAOYSA-N Chlorofluoromethane Chemical compound FCCl XWCDCDSDNJVCLO-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes 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
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 description 1
- 229960003132 halothane Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
-
- 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
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE9800910 | 1998-12-18 | ||
| BE9800910 | 1998-12-18 | ||
| CNB998162469A CN100387561C (zh) | 1998-12-18 | 1999-12-16 | 含有至少一种含氢氟烷和氟化氢的混合物的分离方法,含氢氟烷的制备方法和共沸组合物 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB998162469A Division CN100387561C (zh) | 1998-12-18 | 1999-12-16 | 含有至少一种含氢氟烷和氟化氢的混合物的分离方法,含氢氟烷的制备方法和共沸组合物 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104987277A true CN104987277A (zh) | 2015-10-21 |
Family
ID=3891577
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510305450.6A Pending CN104987277A (zh) | 1998-12-18 | 1999-12-16 | 含有至少一种含氢氟烷和氟化氢的混合物的分离方法,含氢氟烷的制备方法和共沸组合物 |
| CNB998162469A Ceased CN100387561C (zh) | 1998-12-18 | 1999-12-16 | 含有至少一种含氢氟烷和氟化氢的混合物的分离方法,含氢氟烷的制备方法和共沸组合物 |
| CN2008100854764A Expired - Lifetime CN101284758B (zh) | 1998-12-18 | 1999-12-16 | 含有至少一种含氢氟烷和氟化氢的混合物的分离方法,含氢氟烷的制备方法和共沸组合物 |
| CNA2005100651304A Pending CN1680232A (zh) | 1998-12-18 | 1999-12-16 | 合成含氢氟烷的方法 |
| CNA2008100854779A Pending CN101284757A (zh) | 1998-12-18 | 1999-12-16 | 含有至少一种含氢氟烷和氟化氢的混合物的分离方法,含氢氟烷的制备方法和共沸组合物 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB998162469A Ceased CN100387561C (zh) | 1998-12-18 | 1999-12-16 | 含有至少一种含氢氟烷和氟化氢的混合物的分离方法,含氢氟烷的制备方法和共沸组合物 |
| CN2008100854764A Expired - Lifetime CN101284758B (zh) | 1998-12-18 | 1999-12-16 | 含有至少一种含氢氟烷和氟化氢的混合物的分离方法,含氢氟烷的制备方法和共沸组合物 |
| CNA2005100651304A Pending CN1680232A (zh) | 1998-12-18 | 1999-12-16 | 合成含氢氟烷的方法 |
| CNA2008100854779A Pending CN101284757A (zh) | 1998-12-18 | 1999-12-16 | 含有至少一种含氢氟烷和氟化氢的混合物的分离方法,含氢氟烷的制备方法和共沸组合物 |
Country Status (19)
| Country | Link |
|---|---|
| US (4) | US6521803B1 (https=) |
| EP (3) | EP2368869A1 (https=) |
| JP (2) | JP4785251B2 (https=) |
| KR (1) | KR100684939B1 (https=) |
| CN (5) | CN104987277A (https=) |
| AR (1) | AR021727A1 (https=) |
| AT (1) | ATE430119T1 (https=) |
| AU (1) | AU769820B2 (https=) |
| BR (1) | BR9916345B1 (https=) |
| CA (1) | CA2355385C (https=) |
| CZ (1) | CZ303077B6 (https=) |
| DE (1) | DE69940828D1 (https=) |
| ES (1) | ES2325778T3 (https=) |
| HU (1) | HU227729B1 (https=) |
| PL (4) | PL206502B1 (https=) |
| RU (2) | RU2392260C2 (https=) |
| TW (1) | TW499407B (https=) |
| WO (1) | WO2000037401A1 (https=) |
| ZA (1) | ZA200104829B (https=) |
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| 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 |
| CN101270029A (zh) * | 2001-06-01 | 2008-09-24 | 霍尼韦尔国际公司 | 1,1,1,3,3-五氟丁烷与氟化氢的类共沸组合物的应用 |
| US7094936B1 (en) * | 2001-07-20 | 2006-08-22 | Great Lakes Chemical Corporation | Process for preparing halogenated alkanes |
| US20030028057A1 (en) * | 2001-07-20 | 2003-02-06 | Stephen Owens | Methods and materials for the preparation and purification of halogenated hydrocarbons |
| FR2855069B1 (fr) * | 2003-05-22 | 2006-06-16 | Solvay | Procede pour la separation d'au moins un compose organique |
| US6988994B2 (en) * | 2003-08-14 | 2006-01-24 | New York University | Positive airway pressure system and method for treatment of sleeping disorder in patient |
| US8101219B2 (en) * | 2004-03-05 | 2012-01-24 | Eggology, Inc. | Apparatus for preparing egg products in a microwave oven |
| US7709438B2 (en) * | 2005-11-01 | 2010-05-04 | E. I. Du Pont De Nemours And Company | Azeotrope compositions comprising nonafluoropentene and hydrogen fluoride and uses thereof |
| US8766020B2 (en) * | 2008-07-31 | 2014-07-01 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US20070106099A1 (en) * | 2005-11-10 | 2007-05-10 | Pcbu Services, Inc. | Production processes and systems |
| RU2445302C2 (ru) | 2006-06-27 | 2012-03-20 | Е.И. Дюпон Де Немур Энд Компани | Способы получения тетрафторпропена |
| 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 |
| US9040759B2 (en) * | 2007-07-06 | 2015-05-26 | Honeywell International Inc. | Preparation of fluorinated olefins via catalytic dehydrohalogenation of halogenated hydrocarbons |
| ES2483995T3 (es) * | 2008-02-21 | 2014-08-08 | E. I. Du Pont De Nemours And Company | Procesos para la separación de 1,3,3,3-tetrafluoropropeno del fluoruro de hidrógeno por medio de destilación azeotrópica |
| CA2717216A1 (en) * | 2008-02-21 | 2009-08-27 | Jeffrey P. Knapp | Azeotrope compositions comprising 3,3,3-trifluoropropene and hydrogen fluoride and processes for separation thereof |
| WO2009105512A1 (en) * | 2008-02-21 | 2009-08-27 | E. I. Du Pont De Nemours And Company | Processes for separation of 2,3,3,3-tetrafluoropropene from hydrogen fluoride by azeotropic distillation |
| US8008243B2 (en) * | 2008-10-31 | 2011-08-30 | Honeywell International Inc. | Azeotrope-like compositions of 1,1,2,3-tetrachloropropene and hydrogen fluoride |
| US8410040B2 (en) * | 2008-10-31 | 2013-04-02 | Honeywell International Inc. | Azeotrope-like compositions of 1,1,1,2,3-pentachloropropane and hydrogen fluoride |
| US20110215273A1 (en) * | 2008-11-13 | 2011-09-08 | Solvay Fluor Gmbh | Hydrofluoroolefins, manufacture of hydrofluoroolefins and methods of using hydrofluoroolefins |
| WO2010060868A1 (en) * | 2008-11-25 | 2010-06-03 | Solvay Fluor Gmbh | Process for the preparation of chlorofluoroalkenes |
| US8093441B2 (en) * | 2008-12-18 | 2012-01-10 | Exxonmobil Research And Engineering Company | Removal of light fluoroalkanes from hydrocarbon streams |
| US8075797B2 (en) * | 2009-01-29 | 2011-12-13 | Honeywell International Inc. | Azeotrope-like compositions of pentafluoropropane, chlorotrifluoropropene, and hydrogen fluoride |
| TW201103972A (en) | 2009-04-01 | 2011-02-01 | Solvay Fluor Gmbh | Process for the manufacture of etched items |
| JP5946821B2 (ja) | 2010-04-02 | 2016-07-06 | ソルヴェイ（ソシエテ アノニム） | ヒドロクロロフルオロアルカン類の脱塩化水素方法 |
| US8921622B2 (en) | 2010-04-02 | 2014-12-30 | Solvay Sa | Process for dehydrofluorinating hydrochlorofluoroalkanes and products obtained thereby |
| US8487155B2 (en) | 2010-12-07 | 2013-07-16 | Exxonmobil Research And Engineering Company | Removal of light fluoroalkanes from hydrocarbon streams |
| US8999909B2 (en) * | 2012-02-23 | 2015-04-07 | Honeywell International Inc. | Azeotropic compositions of 1,1,1,3,3-pentachloropropane and hydrogen fluoride |
| WO2019051390A1 (en) * | 2017-09-11 | 2019-03-14 | The Chemours Company, Fc, Llc | AZEOTROPIC COMPOSITIONS COMPRISING HYDROGEN FLUORIDE AND FLUOROCARBONS |
| CN110092707B (zh) * | 2018-01-30 | 2020-08-11 | 中昊晨光化工研究院有限公司 | 一种四氟乙烯生产过程中去除氟化氢的方法 |
| AU2020256257B2 (en) * | 2019-04-05 | 2026-03-05 | The Chemours Company Fc, Llc | Process for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene and Intermediates for producing same |
| JP6958596B2 (ja) * | 2019-07-01 | 2021-11-02 | ダイキン工業株式会社 | アルカンの製造方法 |
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| DE1443616C3 (de) | 1963-11-13 | 1974-05-09 | Chemische Fabrik Von Heyden Gmbh, 8000 Muenchen | Verbessertes Verfahren zur Fluorierung und Polyfluorierung von Chlor enthaltenden niederen aliphatischen Halogenkohlenwasserstoffen |
| GB9007029D0 (en) * | 1990-03-29 | 1990-05-30 | Ici Plc | Chemical process |
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| ES2118949T3 (es) * | 1992-04-13 | 1998-10-01 | Daikin Ind Ltd | Procedimiento de extraccion de fluoruro de hidrogeno. |
| 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 |
| US5395997A (en) * | 1993-07-29 | 1995-03-07 | Alliedsignal Inc. | Process for the preparation of hydrofluorocarbons having 3 to 7 carbon atoms |
| RU2065430C1 (ru) * | 1994-05-26 | 1996-08-20 | Российский научный центр "Прикладная химия" | Способ получения 1,1,1,3,3-пентафторпропана |
| US5414165A (en) | 1994-07-29 | 1995-05-09 | E. I. Du Pont De Nemours And Company | Process for the manufacture of 1,1,1,3,3,3,-hexafluoropropane |
| WO1996008481A1 (en) | 1994-09-14 | 1996-03-21 | Sagami Chemical Research Center | Epoxycyclohexane derivative and plant growth regulator |
| FR2724928B1 (fr) * | 1994-09-26 | 1996-10-31 | Atochem Elf Sa | Synthese de 1,1,1,3,3-pentafluoropropane |
| WO1997005089A1 (en) | 1995-08-01 | 1997-02-13 | E.I. Du Pont De Nemours And Company | Process for the manufacture of halocarbons and selected compounds and azeotropes with hf |
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| FR2740132B1 (fr) | 1995-10-23 | 1997-12-19 | Solvay | Procede pour la preparation de 1,1,1,3,3-pentafluoropropane |
| FR2744442B1 (fr) * | 1996-02-01 | 1998-02-27 | Atochem Elf Sa | Preparation du 1,1,1,3,3-pentachlorobutane et du 1,1,1,3,3,-pentafluorobutane |
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1999
- 1999-12-16 US US09/868,368 patent/US6521803B1/en not_active Expired - Lifetime
- 1999-12-16 JP JP2000589475A patent/JP4785251B2/ja not_active Expired - Fee Related
- 1999-12-16 DE DE69940828T patent/DE69940828D1/de not_active Expired - Lifetime
- 1999-12-16 KR KR1020017007485A patent/KR100684939B1/ko not_active Expired - Fee Related
- 1999-12-16 CZ CZ20012215A patent/CZ303077B6/cs not_active IP Right Cessation
- 1999-12-16 CN CN201510305450.6A patent/CN104987277A/zh active Pending
- 1999-12-16 CN CNB998162469A patent/CN100387561C/zh not_active Ceased
- 1999-12-16 AU AU24333/00A patent/AU769820B2/en not_active Ceased
- 1999-12-16 PL PL385268A patent/PL206502B1/pl unknown
- 1999-12-16 PL PL385267A patent/PL208572B1/pl unknown
- 1999-12-16 WO PCT/EP1999/010173 patent/WO2000037401A1/fr not_active Ceased
- 1999-12-16 CN CN2008100854764A patent/CN101284758B/zh not_active Expired - Lifetime
- 1999-12-16 RU RU2005122401/04A patent/RU2392260C2/ru not_active IP Right Cessation
- 1999-12-16 HU HU0104672A patent/HU227729B1/hu not_active IP Right Cessation
- 1999-12-16 ES ES99967969T patent/ES2325778T3/es not_active Expired - Lifetime
- 1999-12-16 CN CNA2005100651304A patent/CN1680232A/zh active Pending
- 1999-12-16 CN CNA2008100854779A patent/CN101284757A/zh active Pending
- 1999-12-16 PL PL349391A patent/PL200329B1/pl unknown
- 1999-12-16 EP EP11153263A patent/EP2368869A1/fr not_active Withdrawn
- 1999-12-16 EP EP99967969A patent/EP1140747B1/fr not_active Expired - Lifetime
- 1999-12-16 CA CA2355385A patent/CA2355385C/fr not_active Expired - Fee Related
- 1999-12-16 PL PL385266A patent/PL208571B1/pl unknown
- 1999-12-16 EP EP09158967A patent/EP2078708A1/fr not_active Ceased
- 1999-12-16 BR BRPI9916345-4A patent/BR9916345B1/pt not_active IP Right Cessation
- 1999-12-16 AR ARP990106474A patent/AR021727A1/es not_active Application Discontinuation
- 1999-12-16 RU RU2001119986/04A patent/RU2261856C2/ru not_active IP Right Cessation
- 1999-12-16 AT AT99967969T patent/ATE430119T1/de not_active IP Right Cessation
- 1999-12-27 TW TW088123242A patent/TW499407B/zh not_active IP Right Cessation
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2001
- 2001-06-13 ZA ZA200104829A patent/ZA200104829B/xx unknown
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2002
- 2002-10-29 US US10/282,785 patent/US7074434B2/en not_active Expired - Fee Related
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2006
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Application publication date: 20151021 |