TW201335111A - 製造２，３，３，３－四氟丙烯的方法 - Google Patents
製造２，３，３，３－四氟丙烯的方法 Download PDFInfo
- Publication number
- TW201335111A TW201335111A TW101137935A TW101137935A TW201335111A TW 201335111 A TW201335111 A TW 201335111A TW 101137935 A TW101137935 A TW 101137935A TW 101137935 A TW101137935 A TW 101137935A TW 201335111 A TW201335111 A TW 201335111A
- Authority
- TW
- Taiwan
- Prior art keywords
- ppm
- composition
- less
- present
- impurities
- Prior art date
Links
- 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 39
- 238000000034 method Methods 0.000 title claims description 150
- 230000008569 process Effects 0.000 title claims description 49
- 239000003054 catalyst Substances 0.000 claims abstract description 123
- 239000012535 impurity Substances 0.000 claims abstract description 100
- 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 39
- UMGQVBVEWTXECF-UHFFFAOYSA-N 1,1,2,3-tetrachloroprop-1-ene Chemical compound ClCC(Cl)=C(Cl)Cl UMGQVBVEWTXECF-UHFFFAOYSA-N 0.000 claims abstract description 31
- 238000004519 manufacturing process Methods 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims description 92
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 47
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 41
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 27
- -1 chromium halide Chemical class 0.000 claims description 27
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 26
- 239000001301 oxygen Substances 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 25
- 150000002894 organic compounds Chemical class 0.000 claims description 25
- 238000006116 polymerization reaction Methods 0.000 claims description 24
- 229910052751 metal Inorganic materials 0.000 claims description 23
- 239000002184 metal Substances 0.000 claims description 23
- 239000011651 chromium Substances 0.000 claims description 21
- 239000003112 inhibitor Substances 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 18
- 239000002994 raw material Substances 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 16
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 16
- 239000012808 vapor phase Substances 0.000 claims description 16
- 238000004821 distillation Methods 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 239000000543 intermediate Substances 0.000 claims description 13
- 229910052742 iron Inorganic materials 0.000 claims description 13
- 229910052804 chromium Inorganic materials 0.000 claims description 9
- 239000012025 fluorinating agent Substances 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 claims description 8
- FEKGWIHDBVDVSM-UHFFFAOYSA-N 1,1,1,2-tetrachloropropane Chemical compound CC(Cl)C(Cl)(Cl)Cl FEKGWIHDBVDVSM-UHFFFAOYSA-N 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 239000011777 magnesium Substances 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- LIPPKMMVZOHCIF-UHFFFAOYSA-N 1,1,2-trichloroprop-1-ene Chemical compound CC(Cl)=C(Cl)Cl LIPPKMMVZOHCIF-UHFFFAOYSA-N 0.000 claims description 6
- ZAIDIVBQUMFXEC-UHFFFAOYSA-N 1,1-dichloroprop-1-ene Chemical compound CC=C(Cl)Cl ZAIDIVBQUMFXEC-UHFFFAOYSA-N 0.000 claims description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910017052 cobalt Inorganic materials 0.000 claims description 6
- 239000010941 cobalt Substances 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- FTCVHAQNWWBTIV-UHFFFAOYSA-N 1,1,1,2,2-pentachloropropane Chemical compound CC(Cl)(Cl)C(Cl)(Cl)Cl FTCVHAQNWWBTIV-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 5
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 5
- UAZUEJTXWAXSMA-UHFFFAOYSA-N 1,1-dichlorobut-1-ene Chemical compound CCC=C(Cl)Cl UAZUEJTXWAXSMA-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- AVGQTJUPLKNPQP-UHFFFAOYSA-N 1,1,1-trichloropropane Chemical compound CCC(Cl)(Cl)Cl AVGQTJUPLKNPQP-UHFFFAOYSA-N 0.000 claims description 3
- MAXQCYDCBHPIAB-UHFFFAOYSA-N 1,1,2,3,3-pentachloroprop-1-ene Chemical compound ClC(Cl)C(Cl)=C(Cl)Cl MAXQCYDCBHPIAB-UHFFFAOYSA-N 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 239000000395 magnesium oxide Substances 0.000 claims description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 3
- 229910000480 nickel oxide Inorganic materials 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- DUXFNSHYXUDNPA-UHFFFAOYSA-N 1,1,2,3,4,5-hexachlorohexa-1,3-diene Chemical compound CC(Cl)C(Cl)=C(Cl)C(Cl)=C(Cl)Cl DUXFNSHYXUDNPA-UHFFFAOYSA-N 0.000 claims description 2
- 229910021503 Cobalt(II) hydroxide Inorganic materials 0.000 claims description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 claims description 2
- 229910000428 cobalt oxide Inorganic materials 0.000 claims description 2
- ASKVAEGIVYSGNY-UHFFFAOYSA-L cobalt(ii) hydroxide Chemical compound [OH-].[OH-].[Co+2] ASKVAEGIVYSGNY-UHFFFAOYSA-L 0.000 claims description 2
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 claims description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 2
- 239000000347 magnesium hydroxide Substances 0.000 claims description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 2
- BFDHFSHZJLFAMC-UHFFFAOYSA-L nickel(ii) hydroxide Chemical compound [OH-].[OH-].[Ni+2] BFDHFSHZJLFAMC-UHFFFAOYSA-L 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 claims description 2
- FFTOUVYEKNGDCM-OWOJBTEDSA-N (e)-1,3,3-trifluoroprop-1-ene Chemical group F\C=C\C(F)F FFTOUVYEKNGDCM-OWOJBTEDSA-N 0.000 claims 2
- 150000001993 dienes Chemical class 0.000 claims 1
- 238000006213 oxygenation reaction Methods 0.000 claims 1
- 238000003682 fluorination reaction Methods 0.000 abstract description 36
- 230000006872 improvement Effects 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 54
- 239000000047 product Substances 0.000 description 52
- 238000004817 gas chromatography Methods 0.000 description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 229910000856 hastalloy Inorganic materials 0.000 description 13
- 230000008859 change Effects 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 238000002161 passivation Methods 0.000 description 10
- 230000015556 catabolic process Effects 0.000 description 9
- 238000006731 degradation reaction Methods 0.000 description 9
- 239000007791 liquid phase Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 239000007789 gas Substances 0.000 description 7
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 7
- 229910001507 metal halide Inorganic materials 0.000 description 7
- 150000005309 metal halides Chemical class 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 6
- 238000009834 vaporization Methods 0.000 description 6
- 230000008016 vaporization Effects 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 3
- 229910016569 AlF 3 Inorganic materials 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 229910052787 antimony Inorganic materials 0.000 description 3
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 229910001092 metal group alloy Inorganic materials 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 239000003507 refrigerant Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- GVVUPGXFVJLPDE-OWOJBTEDSA-N (e)-1,3,3,3-tetrachloroprop-1-ene Chemical compound Cl\C=C\C(Cl)(Cl)Cl GVVUPGXFVJLPDE-OWOJBTEDSA-N 0.000 description 2
- IAPGBTZUBKUKOR-UHFFFAOYSA-N 2,3-dichloro-3,3-difluoroprop-1-ene Chemical compound FC(F)(Cl)C(Cl)=C IAPGBTZUBKUKOR-UHFFFAOYSA-N 0.000 description 2
- NCSLNDWBXYOBGV-UHFFFAOYSA-N 3,3,3-trichloro-1-fluoroprop-1-ene Chemical compound FC=CC(Cl)(Cl)Cl NCSLNDWBXYOBGV-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- 229910000792 Monel Inorganic materials 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 229910021563 chromium fluoride Inorganic materials 0.000 description 2
- UOUJSJZBMCDAEU-UHFFFAOYSA-N chromium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Cr+3].[Cr+3] UOUJSJZBMCDAEU-UHFFFAOYSA-N 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000004088 foaming agent Substances 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- DBGPLCIFYUHWKA-UHFFFAOYSA-H hexachloromolybdenum Chemical compound Cl[Mo](Cl)(Cl)(Cl)(Cl)Cl DBGPLCIFYUHWKA-UHFFFAOYSA-H 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229910001026 inconel Inorganic materials 0.000 description 2
- 229910001119 inconels 625 Inorganic materials 0.000 description 2
- 235000013980 iron oxide Nutrition 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000000711 locust bean gum Substances 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 239000006200 vaporizer Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-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
- PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical compound FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 description 1
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- AAGQOEBQGAJHNT-UHFFFAOYSA-N 2-oxopropyl 2,2,2-trifluoroacetate Chemical compound CC(=O)COC(=O)C(F)(F)F AAGQOEBQGAJHNT-UHFFFAOYSA-N 0.000 description 1
- DGBGIIPEHWOEQZ-UHFFFAOYSA-N 2-phenylmethoxyoxane Chemical compound C=1C=CC=CC=1COC1CCCCO1 DGBGIIPEHWOEQZ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 229910000934 Monel 400 Inorganic materials 0.000 description 1
- 229910018287 SbF 5 Inorganic materials 0.000 description 1
- OSOVKCSKTAIGGF-UHFFFAOYSA-N [Ni].OOO Chemical compound [Ni].OOO OSOVKCSKTAIGGF-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 description 1
- QCMJBECJXQJLIL-UHFFFAOYSA-L chromium(6+);oxygen(2-);difluoride Chemical compound [O-2].[O-2].[F-].[F-].[Cr+6] QCMJBECJXQJLIL-UHFFFAOYSA-L 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- OANFWJQPUHQWDL-UHFFFAOYSA-N copper iron manganese nickel Chemical compound [Mn].[Fe].[Ni].[Cu] OANFWJQPUHQWDL-UHFFFAOYSA-N 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910001293 incoloy Inorganic materials 0.000 description 1
- 229910001055 inconels 600 Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 235000014413 iron hydroxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 229940074869 marquis Drugs 0.000 description 1
- 150000001247 metal acetylides Chemical class 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910000483 nickel oxide hydroxide Inorganic materials 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- CEOCDNVZRAIOQZ-UHFFFAOYSA-N pentachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C(Cl)=C1Cl CEOCDNVZRAIOQZ-UHFFFAOYSA-N 0.000 description 1
- YHBDIEWMOMLKOO-UHFFFAOYSA-I pentachloroniobium Chemical compound Cl[Nb](Cl)(Cl)(Cl)Cl YHBDIEWMOMLKOO-UHFFFAOYSA-I 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- VBUNOIXRZNJNAD-UHFFFAOYSA-N ponazuril Chemical compound CC1=CC(N2C(N(C)C(=O)NC2=O)=O)=CC=C1OC1=CC=C(S(=O)(=O)C(F)(F)F)C=C1 VBUNOIXRZNJNAD-UHFFFAOYSA-N 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 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
- 238000012360 testing method Methods 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- 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
- C07C17/093—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/087—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- 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
- C07C21/04—Chloro-alkenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161547249P | 2011-10-14 | 2011-10-14 | |
| US201161547169P | 2011-10-14 | 2011-10-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW201335111A true TW201335111A (zh) | 2013-09-01 |
Family
ID=48082425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW101137935A TW201335111A (zh) | 2011-10-14 | 2012-10-15 | 製造２，３，３，３－四氟丙烯的方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9359273B2 (enExample) |
| EP (2) | EP2766331B1 (enExample) |
| JP (2) | JP6375498B2 (enExample) |
| KR (1) | KR20140104947A (enExample) |
| CN (2) | CN104080759A (enExample) |
| AR (1) | AR088336A1 (enExample) |
| ES (1) | ES2854833T3 (enExample) |
| MX (1) | MX344948B (enExample) |
| PL (1) | PL2766331T3 (enExample) |
| PT (1) | PT2766331T (enExample) |
| TW (1) | TW201335111A (enExample) |
| WO (1) | WO2013055894A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI770558B (zh) * | 2014-10-16 | 2022-07-11 | 捷克商史波克專業化學杭尼維洛普合股公司 | 用於製備高純度1,1,1,2,3-五氯丙烷產物之方法 |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2766331T3 (pl) * | 2011-10-14 | 2021-09-20 | Honeywell International, Inc. | Sposób wytwarzania 2,3,3,3-tetrafluoropropenu |
| US20140215970A1 (en) * | 2013-02-04 | 2014-08-07 | Honeywell International Inc. | METHODS OF HANDLING CHLORINATED COMPOUNDS USED FOR MANUFACTURING HFO-1234yf |
| CA2948504C (en) * | 2014-05-16 | 2024-02-27 | Occidental Chemical Corporation | Method for making 1,1,3,3-tetrachloropropene |
| CN104151131B (zh) * | 2014-08-08 | 2015-11-18 | 浙江衢化氟化学有限公司 | 一种2,3,3,3-四氟丙烯的制备方法 |
| JP6822964B2 (ja) | 2014-10-16 | 2021-01-27 | スポレク プロ ヘミコウ アー フツニ ブイロブ，アクツィオバ スポレチェノスト | 高純度塩素化アルカンの製造方法 |
| MX389521B (es) * | 2014-10-16 | 2025-03-04 | Spolek Pro Chemickou A Hutni Vyrobu As | Proceso. |
| CN107635955A (zh) | 2015-05-21 | 2018-01-26 | 科慕埃弗西有限公司 | 通过SbF5进行的1233xf至244bb的氢氟化 |
| EP3337777B1 (en) | 2015-08-19 | 2025-01-01 | SPOLCHEMlE Zebra, a.s. | Process for producing c3 chlorinated alkane and alkene compounds |
| WO2017178857A1 (en) | 2016-04-13 | 2017-10-19 | Arkema France | Process for the manufacture of 2,3,3,3-tetrafluoropropene |
| US10793496B2 (en) | 2016-04-13 | 2020-10-06 | Spolek Pro Chemickou A Hutni Vyrobu A.S. | Process for producing a chlorinated alkane |
| FR3078700B1 (fr) * | 2018-03-07 | 2020-07-10 | Arkema France | Procede de production du 2,3,3,3-tetrafluoropropene |
| FR3078699B1 (fr) * | 2018-03-07 | 2020-02-21 | Arkema France | Procede de production du 2,3,3,3-tetrafluoropropene |
| FR3078698B1 (fr) * | 2018-03-07 | 2020-02-21 | Arkema France | Procede de production du 2-chloro-3,3,3-trifluoropropene |
| EP4647419A3 (en) | 2018-08-24 | 2026-01-07 | BL TECHNOLOGIES, Inc. | Synergistic combination for inhibiting polymerization |
| JP7250654B2 (ja) * | 2018-10-09 | 2023-04-03 | ダイキン工業株式会社 | パーフルオロアルキン化合物の製造方法 |
| WO2025019191A2 (en) * | 2023-07-17 | 2025-01-23 | The Chemours Company Fc, Llc | A process to produce 1252zc from 1230xa or 252dc and compositions thereof |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2931840A (en) | 1958-11-25 | 1960-04-05 | Du Pont | Process for preparing 2, 3, 3, 3-tetrafluoropropene |
| US3258500A (en) | 1959-08-17 | 1966-06-28 | Du Pont | Process for fluorinating halohydro-carbons |
| FR2126899B1 (enExample) | 1970-10-16 | 1974-04-26 | Rhone Progil | |
| US4650914A (en) * | 1983-07-06 | 1987-03-17 | Monsanto Company | Process for producing 1,1,2,3-tetrachloropropene |
| US4535194A (en) * | 1983-07-06 | 1985-08-13 | Monsanto Co. | Process for producing 1,1,2,3-tetrachloropropene |
| JPH01207250A (ja) | 1988-02-12 | 1989-08-21 | Daikin Ind Ltd | 含フツ素オレフインの製造方法 |
| US5162594A (en) | 1990-10-11 | 1992-11-10 | E. I. Du Pont De Nemours And Company | Process for production of polyfluoroolefins |
| US5155082A (en) | 1991-04-12 | 1992-10-13 | Allied-Signal Inc. | Catalyst for the manufacture of chlorofluorocarbons, hydrochlorofluorocarbons and hydrofluorocarbons |
| EP1153906B1 (en) | 2000-05-08 | 2003-05-21 | Atofina Chemicals, Inc. | Preparation of 245fa |
| US6313360B1 (en) | 2000-09-29 | 2001-11-06 | Vulcan Materials Company | Process for the manufacture of 1, 1, 1, 3, 3-pentachloropropane |
| US6720466B2 (en) | 2002-04-17 | 2004-04-13 | Vulcan Chemicals, a division of Vulcan Materials Company | 1,1,1,3,3-pentachloropropane process purge stream concentration using a secondary refluxed evaporator and secondary product recovery |
| JP2005285153A (ja) | 2004-03-26 | 2005-10-13 | Toshiba Corp | 情報記録媒体、情報再生装置、情報再生方法、および情報記録方法 |
| WO2005108334A1 (en) * | 2004-04-29 | 2005-11-17 | Honeywell International, Inc. | Processes for synthesis of 1,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropene |
| US8084653B2 (en) | 2004-04-29 | 2011-12-27 | Honeywell International, Inc. | Method for producing fluorinated organic compounds |
| US8058486B2 (en) * | 2004-04-29 | 2011-11-15 | Honeywell International Inc. | Integrated process to produce 2,3,3,3-tetrafluoropropene |
| US8664455B2 (en) * | 2008-08-08 | 2014-03-04 | Honeywell International Inc. | Process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) |
| PL3336074T3 (pl) * | 2006-01-03 | 2025-10-20 | Honeywell International Inc. | Sposób produkcji fluorowanych związków organicznych |
| US8952208B2 (en) * | 2006-01-03 | 2015-02-10 | Honeywell International Inc. | Method for prolonging a catalyst's life during hydrofluorination |
| US8563789B2 (en) * | 2007-06-27 | 2013-10-22 | Arkema Inc. | Process for the manufacture of hydrofluoroolefins |
| US7795480B2 (en) * | 2007-07-25 | 2010-09-14 | Honeywell International Inc. | Method for producing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) |
| US8258355B2 (en) * | 2007-07-25 | 2012-09-04 | Honeywell International Inc. | Processes for preparing 1,1,2,3-tetrachloropropene |
| DK2231565T3 (da) * | 2007-12-19 | 2014-05-26 | Occidental Chem Co | Fremgangsmåder til fremstilling af clorerede carbonhydrider |
| CN101597209A (zh) * | 2008-03-20 | 2009-12-09 | 霍尼韦尔国际公司 | 用于制备2,3,3,3-四氟丙烯的一体式方法 |
| WO2010045104A2 (en) | 2008-10-13 | 2010-04-22 | Dow Global Technologies, Inc. | Process for the production of chlorinated and/or fluorinated propenes |
| KR101392589B1 (ko) | 2009-04-23 | 2014-05-21 | 다이킨 고교 가부시키가이샤 | 2-클로로-3,3,3-트리플루오로프로펜의 제조 방법 |
| KR20120091192A (ko) | 2009-10-09 | 2012-08-17 | 다우 글로벌 테크놀로지스 엘엘씨 | 등온 다중튜브 반응기 및 이를 도입한 방법 |
| CN105664811B (zh) | 2009-10-09 | 2018-10-09 | 蓝立方知识产权公司 | 生产氯化和/或氟化丙烯和高级烯烃的绝热活塞流反应器及方法 |
| CN102686544B (zh) | 2009-10-09 | 2017-02-15 | 蓝立方知识产权公司 | 用于生产氯化和/或氟化丙烯和高级烯烃的方法 |
| CN102639475A (zh) * | 2009-11-16 | 2012-08-15 | 阿科玛股份有限公司 | 纯化和稳定化氯烯烃的方法 |
| WO2011077191A1 (en) | 2009-12-23 | 2011-06-30 | Arkema France | Catalytic gas phase fluorination of 1230xa to 1234yf |
| CN101955414A (zh) * | 2010-04-20 | 2011-01-26 | 南通泰禾化工有限公司 | 1,1,2,3-四氯丙烯生产工艺 |
| CN102911006B (zh) * | 2011-08-04 | 2015-06-17 | 上海泰禾化工有限公司 | 一种制备高纯度低水份四氯丙烯的方法 |
| PL2766331T3 (pl) * | 2011-10-14 | 2021-09-20 | Honeywell International, Inc. | Sposób wytwarzania 2,3,3,3-tetrafluoropropenu |
| JP6056776B2 (ja) | 2014-01-22 | 2017-01-11 | トヨタ自動車株式会社 | 内燃機関の制御装置 |
-
2012
- 2012-10-11 PL PL12840714T patent/PL2766331T3/pl unknown
- 2012-10-11 WO PCT/US2012/059716 patent/WO2013055894A1/en not_active Ceased
- 2012-10-11 CN CN201280061573.4A patent/CN104080759A/zh active Pending
- 2012-10-11 JP JP2014535866A patent/JP6375498B2/ja not_active Expired - Fee Related
- 2012-10-11 EP EP12840714.5A patent/EP2766331B1/en active Active
- 2012-10-11 EP EP20213432.6A patent/EP3808723A1/en active Pending
- 2012-10-11 CN CN201810585977.2A patent/CN109251123A/zh active Pending
- 2012-10-11 MX MX2014004351A patent/MX344948B/es active IP Right Grant
- 2012-10-11 ES ES12840714T patent/ES2854833T3/es active Active
- 2012-10-11 KR KR1020147012569A patent/KR20140104947A/ko not_active Abandoned
- 2012-10-11 US US14/351,732 patent/US9359273B2/en active Active - Reinstated
- 2012-10-11 PT PT128407145T patent/PT2766331T/pt unknown
- 2012-10-15 TW TW101137935A patent/TW201335111A/zh unknown
- 2012-10-15 AR ARP120103833A patent/AR088336A1/es not_active Application Discontinuation
-
2018
- 2018-06-18 JP JP2018115340A patent/JP2018158938A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI770558B (zh) * | 2014-10-16 | 2022-07-11 | 捷克商史波克專業化學杭尼維洛普合股公司 | 用於製備高純度1,1,1,2,3-五氯丙烷產物之方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2766331A4 (en) | 2015-05-27 |
| ES2854833T3 (es) | 2021-09-23 |
| JP2018158938A (ja) | 2018-10-11 |
| MX2014004351A (es) | 2014-09-12 |
| CN109251123A (zh) | 2019-01-22 |
| JP2014530236A (ja) | 2014-11-17 |
| KR20140104947A (ko) | 2014-08-29 |
| JP6375498B2 (ja) | 2018-08-22 |
| US9359273B2 (en) | 2016-06-07 |
| PT2766331T (pt) | 2021-04-08 |
| EP3808723A1 (en) | 2021-04-21 |
| WO2013055894A1 (en) | 2013-04-18 |
| PL2766331T3 (pl) | 2021-09-20 |
| CN104080759A (zh) | 2014-10-01 |
| AR088336A1 (es) | 2014-05-28 |
| EP2766331B1 (en) | 2021-01-06 |
| MX344948B (es) | 2017-01-12 |
| US20140316170A1 (en) | 2014-10-23 |
| EP2766331A1 (en) | 2014-08-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2766331B1 (en) | Process for producing 2,3,3,3-tetrafluoropropene | |
| KR102052141B1 (ko) | 2,3,3,3-테트라플루오로프로펜의 제조 방법 | |
| EP2766329B1 (en) | Process for producing 2,3,3,3-tetrafluoropropene | |
| US20140256995A1 (en) | Process for producing 2,3,3,3-tetrafluoropropene | |
| US8846990B2 (en) | Process for producing 2,3,3,3-tetrafluoropropene | |
| JP6184968B2 (ja) | ２，３，３，３−テトラフルオロプロペンの製造方法 | |
| JP2014530213A (ja) | ２，３，３，３−テトラフルオロプロペンの製造方法 | |
| JP2018008998A (ja) | ２，３，３，３−テトラフルオロプロペンの製造方法 | |
| US9540295B2 (en) | Process for producing 2-chloro-3,3,3-trifluoropropene and 2,3,3,3-tetrafluoropropene |