ES2798771T3 - Procedimiento integrado para producir 2,3,3,3-tetrafluoropropeno - Google Patents
Procedimiento integrado para producir 2,3,3,3-tetrafluoropropeno Download PDFInfo
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- ES2798771T3 ES2798771T3 ES12194295T ES12194295T ES2798771T3 ES 2798771 T3 ES2798771 T3 ES 2798771T3 ES 12194295 T ES12194295 T ES 12194295T ES 12194295 T ES12194295 T ES 12194295T ES 2798771 T3 ES2798771 T3 ES 2798771T3
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- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 238000000034 method Methods 0.000 title claims abstract description 48
- 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 70
- 239000000203 mixture Substances 0.000 claims abstract description 48
- 239000006227 byproduct Substances 0.000 claims abstract description 29
- 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 21
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000000460 chlorine Substances 0.000 claims abstract description 21
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 21
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 20
- 239000012025 fluorinating agent Substances 0.000 claims abstract description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 12
- 239000011737 fluorine Substances 0.000 claims abstract description 8
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 4
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims description 68
- 238000006243 chemical reaction Methods 0.000 claims description 55
- 239000000047 product Substances 0.000 claims description 33
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 28
- 238000004821 distillation Methods 0.000 claims description 28
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 23
- 239000000543 intermediate Substances 0.000 claims description 23
- 239000012808 vapor phase Substances 0.000 claims description 21
- 238000003682 fluorination reaction Methods 0.000 claims description 20
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical class [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 claims description 17
- 239000007791 liquid phase Substances 0.000 claims description 17
- 229910052759 nickel Inorganic materials 0.000 claims description 12
- UMGQVBVEWTXECF-UHFFFAOYSA-N 1,1,2,3-tetrachloroprop-1-ene Chemical compound ClCC(Cl)=C(Cl)Cl UMGQVBVEWTXECF-UHFFFAOYSA-N 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- ZXPCCXXSNUIVNK-UHFFFAOYSA-N 1,1,1,2,3-pentachloropropane Chemical compound ClCC(Cl)C(Cl)(Cl)Cl ZXPCCXXSNUIVNK-UHFFFAOYSA-N 0.000 claims description 10
- 238000007033 dehydrochlorination reaction Methods 0.000 claims description 8
- 239000012071 phase Substances 0.000 claims description 8
- UOUJSJZBMCDAEU-UHFFFAOYSA-N chromium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Cr+3].[Cr+3] UOUJSJZBMCDAEU-UHFFFAOYSA-N 0.000 claims description 7
- 239000000956 alloy Substances 0.000 claims description 5
- 229910045601 alloy Inorganic materials 0.000 claims description 5
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical group Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 5
- 229910001119 inconels 625 Inorganic materials 0.000 claims description 5
- 229910001635 magnesium fluoride Inorganic materials 0.000 claims description 5
- 239000010935 stainless steel Substances 0.000 claims description 4
- 229910001220 stainless steel Inorganic materials 0.000 claims description 4
- PQUUGVDRLWLNGR-UHFFFAOYSA-N 2,3,3,3-tetrachloroprop-1-ene Chemical compound ClC(=C)C(Cl)(Cl)Cl PQUUGVDRLWLNGR-UHFFFAOYSA-N 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 238000011084 recovery Methods 0.000 description 34
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 27
- 239000006200 vaporizer Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000010410 layer Substances 0.000 description 15
- 229910001868 water Inorganic materials 0.000 description 15
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 14
- -1 hydrofluoropropenes Chemical class 0.000 description 12
- 229910000423 chromium oxide Inorganic materials 0.000 description 11
- 235000011149 sulphuric acid Nutrition 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 238000005191 phase separation Methods 0.000 description 8
- 229910001507 metal halide Inorganic materials 0.000 description 7
- 150000005309 metal halides Chemical class 0.000 description 7
- 238000004448 titration Methods 0.000 description 7
- FDOPVENYMZRARC-UHFFFAOYSA-N 1,1,1,2,2-pentafluoropropane Chemical compound CC(F)(F)C(F)(F)F FDOPVENYMZRARC-UHFFFAOYSA-N 0.000 description 6
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000003518 caustics Substances 0.000 description 6
- 239000002274 desiccant Substances 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 238000004064 recycling Methods 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 229910000792 Monel Inorganic materials 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000005498 polishing Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 229910052593 corundum Inorganic materials 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000000463 material 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
- 150000002739 metals Chemical class 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 229910001845 yogo sapphire Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004604 Blowing Agent Substances 0.000 description 2
- 229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 229910001026 inconel Inorganic materials 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 2
- 150000004812 organic fluorine compounds Chemical class 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000003507 refrigerant Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 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
- SHXHPUAKLCCLDV-UHFFFAOYSA-N 1,1,1-trifluoropentane-2,4-dione Chemical compound CC(=O)CC(=O)C(F)(F)F SHXHPUAKLCCLDV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910000934 Monel 400 Inorganic materials 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- 229910010165 TiCu Inorganic materials 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling 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
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910001055 inconels 600 Inorganic materials 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229940074869 marquis Drugs 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 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
- 238000002360 preparation method Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 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
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 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
- 238000011282 treatment Methods 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/04—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated 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
- C07C21/18—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
- C01B7/01—Chlorine; Hydrogen chloride
- C01B7/03—Preparation from chlorides
- C01B7/035—Preparation of hydrogen chloride from chlorides
-
- 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
- C01B7/01—Chlorine; Hydrogen chloride
- C01B7/07—Purification ; Separation
- C01B7/0706—Purification ; Separation of hydrogen chloride
-
- 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
- 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
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
-
- 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
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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| US3832708P | 2008-03-20 | 2008-03-20 | |
| US12/404,130 US8058486B2 (en) | 2004-04-29 | 2009-03-13 | Integrated process to produce 2,3,3,3-tetrafluoropropene |
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| ES2798771T3 true ES2798771T3 (es) | 2020-12-14 |
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| ES12194295T Active ES2798771T3 (es) | 2008-03-20 | 2009-03-16 | Procedimiento integrado para producir 2,3,3,3-tetrafluoropropeno |
| ES09155292T Active ES2329867T5 (es) | 2008-03-20 | 2009-03-16 | Procedimiento integrado para producir 2,3,3,3-tetrafluoropropeno |
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| ES09155292T Active ES2329867T5 (es) | 2008-03-20 | 2009-03-16 | Procedimiento integrado para producir 2,3,3,3-tetrafluoropropeno |
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| EP (3) | EP2103587B2 (enExample) |
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| MX (1) | MX2009002967A (enExample) |
| PL (1) | PL2583959T3 (enExample) |
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Families Citing this family (178)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9024092B2 (en) * | 2006-01-03 | 2015-05-05 | 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 |
| US8084653B2 (en) * | 2004-04-29 | 2011-12-27 | Honeywell International, Inc. | Method for producing fluorinated organic compounds |
| US20230150900A1 (en) * | 2004-04-29 | 2023-05-18 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US8952208B2 (en) * | 2006-01-03 | 2015-02-10 | Honeywell International Inc. | Method for prolonging a catalyst's life during hydrofluorination |
| US8071825B2 (en) | 2006-01-03 | 2011-12-06 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| GB0806422D0 (en) * | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
| US9670117B2 (en) * | 2007-01-03 | 2017-06-06 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US10343962B2 (en) * | 2007-01-03 | 2019-07-09 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US8063257B2 (en) * | 2007-01-03 | 2011-11-22 | Honeywell International Inc. | Method for producing 2,3,3,3-tetrafluoropropene |
| US8563789B2 (en) * | 2007-06-27 | 2013-10-22 | Arkema Inc. | Process for the manufacture of hydrofluoroolefins |
| US9416074B2 (en) | 2007-07-06 | 2016-08-16 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| WO2013055726A1 (en) | 2011-10-14 | 2013-04-18 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US9493384B2 (en) | 2007-07-06 | 2016-11-15 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US8846990B2 (en) | 2007-07-06 | 2014-09-30 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US9035111B2 (en) * | 2007-08-22 | 2015-05-19 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US8845921B2 (en) * | 2008-04-09 | 2014-09-30 | Honeywell International Inc. | Separation of close boiling compounds by addition of a third compound |
| US8975454B2 (en) | 2008-07-31 | 2015-03-10 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| CA2739924C (en) * | 2008-10-13 | 2017-03-07 | Dow Global Technologies Llc | Process for the production of chlorinated and/or fluorinated propenes |
| 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 |
| JP5418603B2 (ja) * | 2009-04-23 | 2014-02-19 | ダイキン工業株式会社 | 2,3,3,3−テトラフルオロプロペンの製造方法 |
| US8779219B2 (en) * | 2009-05-13 | 2014-07-15 | Daikin Industries, Ltd. | Process for preparing chlorine-containing fluorocarbon compound |
| CN102596387B (zh) | 2009-10-09 | 2015-11-25 | 陶氏环球技术有限责任公司 | 生产氯化和/或氟化丙烯和高级烯烃的等温多管反应器和方法 |
| JP5706432B2 (ja) | 2009-10-09 | 2015-04-22 | ダウ グローバル テクノロジーズ エルエルシー | 塩素化及び/又はフッ素化プロペンの製造方法 |
| KR20120084729A (ko) | 2009-10-09 | 2012-07-30 | 다우 글로벌 테크놀로지스 엘엘씨 | 염화 및/또는 불화 프로펜 및 고급 알켄의 제조 방법 |
| US8618340B2 (en) * | 2009-11-03 | 2013-12-31 | Honeywell International Inc. | Integrated process for fluoro-olefin production |
| JP5626345B2 (ja) * | 2009-11-10 | 2014-11-19 | ダイキン工業株式会社 | 2,3,3,3−テトラフルオロプロペンの精製方法 |
| SI2845891T1 (sl) | 2009-12-22 | 2020-02-28 | The Chemours Company Fc, Llc | Sestavki, ki obsegajo 2,3,3,3-tetrafluoropropen in 2,3-dikloro-3,3-difluoropropen |
| CN102686543B (zh) | 2009-12-23 | 2015-04-15 | 阿克马法国公司 | 1230xa到1234yf的催化气相氟化 |
| ES2556955T3 (es) * | 2009-12-23 | 2016-01-21 | Arkema France | Fluoración catalítica en fase gaseosa de 243db para dar 1234yf |
| WO2011077191A1 (en) * | 2009-12-23 | 2011-06-30 | Arkema France | Catalytic gas phase fluorination of 1230xa to 1234yf |
| EP2516366B1 (en) | 2009-12-23 | 2016-11-16 | Arkema France | Catalytic gas phase fluorination of 1233xf to 1234yf |
| MX2012009204A (es) | 2010-02-12 | 2012-09-07 | Daikin Ind Ltd | Proceso para producir un compuesto de alqueno que contiene fluor. |
| US8114308B2 (en) * | 2010-03-30 | 2012-02-14 | Honeywell International Inc. | Azeotrope-like composition of 2,3-dichloro-3,3-difluoropropene (HCFO-1232xf) and hydrogen fluoride (HF) |
| US8426656B2 (en) | 2010-04-05 | 2013-04-23 | Honeywell International Inc. | Integrated process to co-produce trans-1-chloro-3,3,3-trifluoropropene and trans-1,3,3,3-tetrafluoropropene |
| WO2012066375A1 (en) * | 2010-11-15 | 2012-05-24 | Arkema France | Process for the manufacture of 2 - chloro - 3, 3, 3 - trifluoropropene (hcfo 1233xf) by liquid phase fluorination of pentachloropropane |
| EP2563750B1 (en) * | 2010-04-26 | 2017-10-04 | Arkema France | Process for the manufacture of 2-chloro-3, 3, 3-trifluoropropene (hcfo 1233xf) by liquid phase fluorination of pentachloropropane |
| WO2011135395A1 (en) * | 2010-04-26 | 2011-11-03 | Arkema France | Process for the manufacture of 2-chloro-3, 3,3-trifluoropropene (hcfo1233xf) by liquid phase fluorination of pentachloropropane |
| US8436218B2 (en) | 2010-05-27 | 2013-05-07 | Honeywell International Inc. | Azeotrope-like composition of hexafluoropropane, hexafluoropropene and hydrogen fluoride |
| US8263817B2 (en) * | 2010-07-06 | 2012-09-11 | E I Du Pont De Nemours And Company | Synthesis of 1234YF by selective dehydrochlorination of 244BB |
| FR2962442B1 (fr) | 2010-07-09 | 2016-02-26 | Arkema France | Composition stable de 2,3,3,3-tetrafluoropropene |
| CN101913989B (zh) * | 2010-09-07 | 2013-06-05 | 西安近代化学研究所 | 2,3,3,3-四氟丙烯的生产方法 |
| WO2012052797A1 (en) | 2010-10-22 | 2012-04-26 | Arkema France | Process for the preparation of 2,3,3,3 tetrafluoropropene |
| US9284240B2 (en) | 2010-10-22 | 2016-03-15 | Arkema France | Process for the manufacture of 2-chloro-3,3,3-trifluoropropene by gas phase fluorination of pentachloropropane |
| EP2632881B1 (en) | 2010-10-25 | 2017-07-26 | Arkema France | Process for the manufacture of 2-chloro-1,1,1,2-tetrafluoropropane by liquid phase fluorination of 2-chloro-3,3,3-trifluoropropene |
| EP2632882B2 (en) | 2010-10-27 | 2023-04-12 | Daikin Industries, Ltd. | Process for producing 2,3,3,3-tetrafluoropropene |
| CN103119005B (zh) | 2010-12-16 | 2016-10-26 | 株式会社德山 | 碳数为3的氯化烃的制备方法 |
| US9156752B2 (en) * | 2011-01-04 | 2015-10-13 | Honeywell International Inc. | High purity E-1-chloro-3,3,3-trifluoropropene and methods of making the same |
| US8680345B2 (en) * | 2011-01-07 | 2014-03-25 | Honeywell International Inc. | Low temperature production of 2-chloro-3,3,3-trifluoropropene |
| US9890096B2 (en) * | 2011-01-19 | 2018-02-13 | Honeywell International Inc. | Methods of making 2,3,3,3-tetrafluoro-2-propene |
| EP3135658B1 (en) | 2011-01-21 | 2020-04-22 | Arkema France | Process for the manufacture of 2,3,3,3-tetrafluoropropene by gas phase fluorination of pentachloropropane |
| RU2571415C2 (ru) * | 2011-01-21 | 2015-12-20 | Аркема Франс | Каталитическое газофазное фторирование |
| EP3466912B1 (en) | 2011-01-21 | 2022-04-13 | Arkema France | Catalytic gas phase fluorination |
| US8741828B2 (en) | 2011-02-23 | 2014-06-03 | Honeywell International Inc. | Azeotrope and azeotrope-like compositions useful for the production of haloolefins |
| EP2714631B1 (en) | 2011-05-31 | 2020-05-13 | Blue Cube IP LLC | Process for the production of chlorinated propenes |
| CA2836493A1 (en) | 2011-05-31 | 2012-12-06 | Max Markus Tirtowidjojo | Process for the production of chlorinated propenes |
| JP6267114B2 (ja) | 2011-06-08 | 2018-01-24 | ダウ アグロサイエンシィズ エルエルシー | 塩素化および/またはフッ素化プロペンを生成するためのプロセス |
| FR2977584B1 (fr) | 2011-07-08 | 2014-12-05 | Arkema France | Procede de separation et recuperation du 2,3,3,3-tetrafluoropropene et de l'acide fluorhydrique |
| GB2492847A (en) * | 2011-07-15 | 2013-01-16 | Mexichem Amanco Holding Sa | A process for reducing TFMA content in R-1234 |
| CN103717560B (zh) | 2011-07-26 | 2016-04-27 | 大金工业株式会社 | 用于制备2,3,3,3-四氟丙烯的方法 |
| WO2013022676A1 (en) | 2011-08-07 | 2013-02-14 | Dow Global Technologies, Llc | Process for the production of chlorinated propenes |
| WO2013022806A1 (en) | 2011-08-07 | 2013-02-14 | Dow Global Technologies, Llc | Process for the production of chlorinated propenes |
| EP3608304A1 (en) | 2011-09-15 | 2020-02-12 | Daikin Industries, Ltd. | Method for purifying chlorinated hydrocarbon |
| IN2014DN02371A (enExample) | 2011-09-30 | 2015-05-15 | Honeywell Int Inc | |
| CN103946197B (zh) * | 2011-09-30 | 2017-02-22 | 霍尼韦尔国际公司 | 制造2,3,3,3‑四氟丙烯的方法 |
| US8796493B2 (en) | 2011-09-30 | 2014-08-05 | Honeywell International Inc. | Methods to separate halogentated olefins from 2-chloro-1,1,1,2-tetrafluoropropane using a solid adsorbent |
| IN2014DN02372A (enExample) * | 2011-09-30 | 2015-05-15 | Honeywell Int Inc | |
| EP3808723A1 (en) | 2011-10-14 | 2021-04-21 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| CN107954828A (zh) * | 2011-10-14 | 2018-04-24 | 霍尼韦尔国际公司 | 制备2,3,3,3-四氟丙烯的方法 |
| KR20140079508A (ko) | 2011-10-31 | 2014-06-26 | 다이킨 고교 가부시키가이샤 | 2-클로로-3,3,3-트리플루오로프로펜의 제조방법 |
| ES2752461T3 (es) * | 2011-11-04 | 2020-04-06 | Honeywell Int Inc | Proceso para producir 2,3,3,3-tetrafluoropropeno |
| MX357840B (es) | 2011-11-04 | 2018-07-26 | Bektesevic Selma | Proceso para producir 2,3,3,3-tetrafluoropropeno. |
| US9102580B2 (en) | 2011-11-10 | 2015-08-11 | The Chemours Company Fc, Llc | Catalytic fluorination process of making hydrohaloalkane |
| WO2013078035A1 (en) | 2011-11-21 | 2013-05-30 | Dow Global Technologies, Llc | Process for the production of chlorinated alkanes |
| WO2013082410A1 (en) | 2011-12-02 | 2013-06-06 | Dow Global Technologies, Llc | Process for the production of chlorinated alkanes |
| EP2785670B1 (en) | 2011-12-02 | 2017-10-25 | Blue Cube IP LLC | Process for the production of chlorinated alkanes |
| CN104024188B (zh) | 2011-12-13 | 2018-05-01 | 蓝立方知识产权有限责任公司 | 生产氯化丙烷和丙烯的方法 |
| PL2791093T3 (pl) | 2011-12-14 | 2018-01-31 | Arkema France | Sposób wytwarzania 2,3,3,3-tetrafluoropropenu |
| CA2860203C (en) | 2011-12-22 | 2018-01-30 | Dow Global Technologies Llc | Process for the production of tetrachloromethane |
| WO2013096706A1 (en) | 2011-12-23 | 2013-06-27 | Dow Global Technologies, Llc | Process for the production of alkenes and/or aromatic compounds |
| FR2986525B1 (fr) | 2012-02-03 | 2014-02-14 | Arkema France | Procede de production de 2,3,3,3-tetrafluoropropene |
| CN109232172A (zh) * | 2012-02-10 | 2019-01-18 | 汪海有 | 用于制造2,3,3,3-四氟丙烯的改进的方法 |
| WO2013130385A1 (en) | 2012-02-29 | 2013-09-06 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US9162945B2 (en) | 2012-03-22 | 2015-10-20 | Daikin Industries, Ltd. | Process for preparing 2-chloro-3,3,3-trifluoropropene |
| US9000239B2 (en) | 2012-05-15 | 2015-04-07 | Honeywell International Inc. | Methods for producing 1-chloro-3,3,3-trifluoropropene from 2-chloro-3,3,3-trifluoropropene |
| WO2013184865A1 (en) * | 2012-06-06 | 2013-12-12 | E.I. Du Pont De Nemours And Company | PROCESS FOR THE REDUCTION OF RfCCX IMPURITIES IN FLUOROOLEFINS |
| WO2014025065A1 (en) | 2012-08-08 | 2014-02-13 | Daikin Industries, Ltd. | Process for producing 2,3,3,3-tetrafluoropropene |
| JP2015529247A (ja) | 2012-09-20 | 2015-10-05 | ダウ グローバル テクノロジーズ エルエルシー | 塩素化プロペンの生成のためのプロセス |
| WO2014046970A1 (en) | 2012-09-20 | 2014-03-27 | Dow Global Technologies, Llc | Process for the production of chlorinated propenes |
| CN104718020A (zh) | 2012-09-30 | 2015-06-17 | 陶氏环球技术有限公司 | 堰式骤冷器和并入所述堰式骤冷器的工艺 |
| US10065157B2 (en) | 2012-10-26 | 2018-09-04 | Blue Cube Ip Llc | Mixer and processes incorporating the same |
| JP6247311B2 (ja) | 2012-12-18 | 2017-12-13 | ブルー キューブ アイピー エルエルシー | 塩素化プロペンを生成するための方法 |
| US9475740B2 (en) | 2012-12-19 | 2016-10-25 | Blue Cube Ip Llc | Process for the production of chlorinated propenes |
| US8889930B2 (en) | 2013-01-22 | 2014-11-18 | Axiall Ohio, Inc. | Process for producing chlorinated hydrocarbons |
| US9289758B2 (en) | 2013-01-22 | 2016-03-22 | Axiall Ohio, Inc. | Processes for producing chlorinated hydrocarbons and methods for recovering polyvalent antimony catalysts therefrom |
| US8907147B2 (en) | 2013-02-04 | 2014-12-09 | Honeywell International Inc. | Synthesis of 1,1,2,3-tetrachloropropene |
| US8889929B2 (en) | 2013-02-19 | 2014-11-18 | Honeywell International Inc. | Process to make 1,1,2,3-tetrachloropropene from 1,1,3-trichloropropene and/or 3,3,3-trichloropropene |
| JP2016507590A (ja) | 2013-02-27 | 2016-03-10 | ブルー キューブ アイピー エルエルシー | 塩素化プロペンを生成するための方法 |
| EP2964597B1 (en) | 2013-03-09 | 2017-10-04 | Blue Cube IP LLC | Process for the production of chlorinated alkanes |
| CN107021868A (zh) * | 2013-03-12 | 2017-08-08 | 霍尼韦尔国际公司 | 用于减少1233xf氢氟化为244bb过程中245cb形成的方法 |
| WO2014165094A1 (en) * | 2013-03-13 | 2014-10-09 | Honeywell International Inc. | Staged fluorination process and reactor system |
| US10022576B2 (en) * | 2013-03-13 | 2018-07-17 | Arkema Inc. | Methods for purifying and stabilizing hydrofluoroolefins and hydrochlorofluoroolefins |
| US9180433B2 (en) | 2013-03-14 | 2015-11-10 | Honeywell International, Inc. | Catalysts for 2-chloro-1,1,1,2-tetrafluoropropane dehydrochlorination |
| US9353029B2 (en) * | 2013-03-14 | 2016-05-31 | Honeywell International, Inc. | Fluorination process and reactor |
| US9090531B2 (en) | 2013-03-14 | 2015-07-28 | Honeywell International Inc. | Method for mitigating HCL generation during 1,1,2,3-tetrachloropropene purification |
| US8859829B2 (en) * | 2013-03-14 | 2014-10-14 | Honeywell International Inc. | Stabilizer and inhibitor for chloropropenes, such as tetrachloropropene 1,1,2,3-tetrachloropropene (1230xa), used in the manufacture of 2,3,3,3-tetrafluoropropene (1234yf) |
| US20150259267A1 (en) | 2014-03-14 | 2015-09-17 | E.I. Du Pont De Nemours And Company | PROCESS FOR THE REDUCTION OF RfC=CX IMPURITIES IN FLUOROOLEFINS |
| CN107827707A (zh) * | 2013-03-15 | 2018-03-23 | 霍尼韦尔国际公司 | 制备2‑氯‑1,1,1,2‑四氟丙烷(HCFC‑244bb)的方法 |
| US9233895B2 (en) | 2013-03-15 | 2016-01-12 | Honeywell International, Inc. | Process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) |
| PL2970058T3 (pl) * | 2013-03-15 | 2024-05-06 | Honeywell International Inc. | Sposób usuwania fluorowcowanego etylenu stanowiącego zanieczyszczenia z mieszaniny fluoroolefin |
| US20140275651A1 (en) | 2013-03-15 | 2014-09-18 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US10995047B2 (en) | 2013-03-15 | 2021-05-04 | The Chemours Company Fc, Llc | Process for the reduction of RƒC≡CX impurities in fluoroolefins |
| US9334206B2 (en) * | 2013-03-15 | 2016-05-10 | Honeywell International Inc. | Integrated process to produce 2,3,3,3-tetrafluoropropene |
| EP2970055B1 (en) * | 2013-03-15 | 2018-07-25 | The Chemours Company FC, LLC | Process for the reduction of alkyne impurities in fluoroolefins |
| EP2986583B1 (en) * | 2013-04-18 | 2019-07-17 | Honeywell International Inc. | Reaction system and process to produce fluorinated organics |
| JP5825299B2 (ja) | 2013-07-12 | 2015-12-02 | ダイキン工業株式会社 | 2,3,3,3−テトラフルオロプロペンの製造方法 |
| JPWO2015022731A1 (ja) | 2013-08-13 | 2017-03-02 | 日立オートモティブシステムズ株式会社 | 電池監視装置、電池システムおよび車両制御システム |
| US9139497B2 (en) | 2013-10-23 | 2015-09-22 | Axiall Ohio, Inc. | Process for producing chlorinated hydrocarbons in the presence of a polyvalent bismuth compound |
| EP3104965B1 (en) | 2014-02-10 | 2019-09-25 | Honeywell International Inc. | Reactor for liquid phase fluorination reactions |
| US9663425B2 (en) | 2014-03-31 | 2017-05-30 | Honeywell International Inc. | Method to produce 1,1,2,3-tetrachloropropene with high yield |
| FR3023286B1 (fr) | 2014-07-02 | 2018-02-16 | Arkema France | Procede de fabrication de tetrafluoropropene |
| JP5939283B2 (ja) * | 2014-07-15 | 2016-06-22 | ダイキン工業株式会社 | クロロプロペンの製造方法及び2,3,3,3−テトラフルオロプロペンの製造方法 |
| 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 |
| CN107074695A (zh) | 2014-09-30 | 2017-08-18 | 大金工业株式会社 | 2,3,3,3-四氟丙烯的制造方法 |
| FR3027303B1 (fr) * | 2014-10-16 | 2016-10-07 | Arkema France | Compositions a base de 1,1,1,2,3-pentachloropropane |
| CN105777484B (zh) * | 2014-12-13 | 2018-04-27 | 西安近代化学研究所 | 2,3,3,3-四氟丙烯的制备方法 |
| FR3033791B1 (fr) | 2015-03-18 | 2017-04-14 | Arkema France | Stabilisation du 1-chloro-3,3,3-trifluoropropene |
| MX2017013511A (es) * | 2015-04-24 | 2018-02-09 | Honeywell Int Inc | Proceso para reducir la concentracion de 1233xf en 244bb. |
| KR102847526B1 (ko) | 2015-05-21 | 2025-08-20 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | SbF5에 의한 1233xf의 244bb로의 히드로플루오린화 |
| GB2540427B (en) | 2015-07-17 | 2017-07-19 | Mexichem Fluor Sa De Cv | Process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) |
| GB2559056B (en) | 2015-07-17 | 2019-09-11 | Mexichem Fluor Sa De Cv | Process for preparing 245cb and 1234yf from 243db |
| GB201512510D0 (en) | 2015-07-17 | 2015-08-19 | Mexichem Fluor Sa De Cv | Process |
| CN107848915A (zh) * | 2015-08-05 | 2018-03-27 | 阿科玛股份有限公司 | 具有高氟化活性的氟氧化铬催化剂 |
| JP6038251B2 (ja) * | 2015-08-20 | 2016-12-07 | アルケマ フランス | ペンタクロロプロパンの気相フッ素化による2−クロロ−3,3,3−トリフルオロプロペンの製造方法 |
| JP6043415B2 (ja) * | 2015-08-20 | 2016-12-14 | アルケマ フランス | 2,3,3,3−テトラフルオロプロペンの製造方法 |
| KR102645472B1 (ko) | 2015-10-15 | 2024-03-07 | 허니웰 인터내셔날 인코포레이티드 | 탈할로겐화수소 반응기 및 방법 |
| US9856193B2 (en) | 2015-11-12 | 2018-01-02 | Honeywell International Inc. | Process for the production of fluorinated cyclobutane |
| US10005705B2 (en) | 2015-11-12 | 2018-06-26 | Honeywell International Inc. | Process for the production of fluorinated cyclobutane |
| US9790151B2 (en) | 2015-11-12 | 2017-10-17 | Honeywell International Inc. | Process for making 2,3,3,3-tetrafluoropropene and/or vinylidine fluoride |
| FR3045029B1 (fr) | 2015-12-14 | 2025-10-31 | Arkema France | Fluoration catalytique en phase gazeuse avec des catalyseurs a base de chrome |
| AU2017281894A1 (en) * | 2016-06-23 | 2019-01-17 | 3M Innovative Properties Company | Personal protective equipment system having analytics engine with integrated monitoring, alerting, and predictive safety event avoidance |
| FR3056210B1 (fr) | 2016-09-22 | 2020-03-13 | Arkema France | Procede de separation du 2-chloro-1,1,1,2-tetrafluoropropane et du 2-chloro-3,3,3-trifluoropropene. |
| EP4253355A3 (en) | 2016-11-02 | 2023-12-06 | Honeywell International Inc. | Process for reducing 3,3,3-trifluoropropyne in 2,3,3,3-tetrafluoropropene |
| JP6968162B2 (ja) | 2016-11-08 | 2021-11-17 | ハネウェル・インターナショナル・インコーポレーテッドHoneywell International Inc. | フッ素化シクロブタンを生成するためのプロセス |
| FR3066927B1 (fr) * | 2017-06-06 | 2019-06-21 | Arkema France | Procede de modification de la distribution en fluor dans un compose hydrocarbure. |
| FR3066926B1 (fr) * | 2017-06-06 | 2020-05-22 | Arkema France | Procede de modification de la distribution en fluor dans un compose hydrocarbure. |
| FR3068969B1 (fr) | 2017-07-17 | 2019-07-26 | Arkema France | Procede de production du 2,3,3,3-tetrafluoropropene. |
| KR101992230B1 (ko) | 2017-08-08 | 2019-06-25 | (주)후성 | 기상 촉매를 이용한 1,1,1-트리플루오로-2-클로로프로펜과 1,1,1,2-테트라플루오로프로펜의 동시 제조 방법 |
| US10233137B1 (en) | 2017-10-13 | 2019-03-19 | Honeywell International Inc. | Method for removing unsaturated halogenated impurities from 2,3,3,3-tetrafluoropropene (HFO-1234yf) |
| CN107721809B (zh) | 2017-10-19 | 2020-06-19 | 浙江衢化氟化学有限公司 | 一种2,3,3,3-四氟丙烯和反式-1,3,3,3-四氟丙烯的联产方法 |
| FR3073516B1 (fr) | 2017-11-13 | 2019-10-18 | Arkema France | Procede de production du 2,3,3,3-tetrafluoropropene. |
| US10125066B1 (en) | 2017-11-29 | 2018-11-13 | Honeywell International Inc. | Process for making high purity 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) |
| US10246389B1 (en) | 2018-01-08 | 2019-04-02 | Honeywell International Inc. | Compositions containing 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) |
| US10351494B1 (en) | 2018-01-08 | 2019-07-16 | Honeywell International Inc. | Systems and methods for reducing the formation of impurities during 244bb dehydrochlorination to 1234yf |
| FR3078699B1 (fr) | 2018-03-07 | 2020-02-21 | Arkema France | Procede de production du 2,3,3,3-tetrafluoropropene |
| FR3078697B1 (fr) | 2018-03-07 | 2020-02-21 | Arkema France | Procede de dehydrofluoration d'un compose hydrocarbure. |
| FR3078700B1 (fr) | 2018-03-07 | 2020-07-10 | 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 |
| CN119118782A (zh) * | 2018-06-06 | 2024-12-13 | 霍尼韦尔国际公司 | 用于HCFC-244bb的脱氯化氢以制备HFO-1234yf的方法 |
| FR3082201A1 (fr) | 2018-06-12 | 2019-12-13 | Arkema France | Procede de production de 2,3,3,3-tetrafluoropropene, reacteur et installation pour la mise en oeuvre de celui-ci. |
| FR3098127B1 (fr) | 2018-06-12 | 2022-10-21 | Arkema France | Procédé de production de 2,3,3,3-tétrafluoropropène et réacteur pour la mise en œuvre de celui-ci |
| FR3082203B1 (fr) | 2018-06-12 | 2020-08-14 | Arkema France | Procede de production de 2,3,3,3-tetrafluoropropene et installation pour la mise en oeuvre de celui-ci. |
| FR3082200B1 (fr) | 2018-06-12 | 2020-08-28 | Arkema France | Procede de production de 2,3,3,3-tetrafluoropropene et reacteur pour la mise en oeuvre de celui-ci. |
| FR3082204B1 (fr) | 2018-06-12 | 2020-08-14 | Arkema France | Procede de production de 2-chloro-3,3,3-trifluoropropene et installation pour la mise en oeuvre de celui-ci. |
| FR3082202B1 (fr) | 2018-06-12 | 2020-08-28 | Arkema France | Procede de production de 2,3,3,3-tetrafluoropropene et installation pour la mise en oeuvre de celui-ci. |
| WO2020014130A1 (en) * | 2018-07-09 | 2020-01-16 | The Chemours Company Fc, Llc | Compositions and methods for an integrated 2,3,3,3-tetrafluoropropene manufacturing process |
| FR3084359B1 (fr) | 2018-07-25 | 2021-11-26 | Arkema France | Procede de production et de purification du 2-chloro-1,1,1,2-tetrafluoropropane. |
| KR102863123B1 (ko) | 2018-08-24 | 2025-09-22 | 허니웰 인터내셔날 인코포레이티드 | 트라이플루오로요오도메탄 및 트라이플루오로아세틸 요오다이드의 제조 방법 |
| CN109438171B (zh) * | 2018-11-27 | 2022-02-01 | 浙江三美化工股份有限公司 | 一种气相连续合成2,3,3,3-四氟丙烯的方法 |
| US10941091B2 (en) | 2018-12-03 | 2021-03-09 | Honeywell International Inc. | Processes for producing high-purity trifluoroiodomethane |
| JP2022514907A (ja) | 2018-12-21 | 2022-02-16 | ハネウェル・インターナショナル・インコーポレーテッド | 1,2,2-トリフルオロ-1-トリフルオロメチルシクロブタンを含有する起泡剤組成物、及び発泡方法 |
| CN109796300B (zh) | 2018-12-29 | 2020-12-18 | 浙江巨化技术中心有限公司 | 一种2,3,3,3-四氟丙烯的连续制备方法 |
| US11554956B2 (en) | 2019-04-16 | 2023-01-17 | Honeywell International Inc. | Integrated process and catalysts for manufacturing hydrogen iodide from hydrogen and iodine |
| CN110013853B (zh) | 2019-05-08 | 2021-10-01 | 西安近代化学研究所 | 一种气相加氢脱氯制备2,3,3,3-四氟丙烯用催化剂 |
| CN121135558A (zh) * | 2019-11-06 | 2025-12-16 | 霍尼韦尔国际公司 | Hcfc-244bb和水的共沸物或类共沸物组合物 |
| FR3098216B1 (fr) | 2020-07-03 | 2023-01-13 | Arkema France | Procédé de production de 2,3,3,3-tétrafluoropropène et installation pour la mise en œuvre de celui-ci |
| CN115350504A (zh) * | 2022-08-26 | 2022-11-18 | 浙江工程设计有限公司 | 一种HCFC-142b的制备装置及方法 |
Family Cites Families (16)
| 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 |
| 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 |
| JP3821514B2 (ja) * | 1996-06-20 | 2006-09-13 | セントラル硝子株式会社 | 1,3,3,3−テトラフルオロプロペンの製造法 |
| WO1999026907A1 (en) * | 1997-11-25 | 1999-06-03 | Imperial Chemical Industries Plc | Preparation of fluorine-containing organic compounds |
| US7285690B2 (en) * | 2003-10-14 | 2007-10-23 | E.I. Du Pont De Nemours And Company | Process for the preparation of 1,1,1,3,3-pentafluoropropane and 1,1,1,3,3,3-hexafluoropropane |
| 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 |
| US8071825B2 (en) * | 2006-01-03 | 2011-12-06 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| HUE072581T2 (hu) | 2006-01-03 | 2025-11-28 | Honeywell Int Inc | Eljárás fluorozott szerves vegyületek elõállítására |
| JP5416587B2 (ja) * | 2006-10-03 | 2014-02-12 | メキシケム、アマンコ、ホールディング、ソシエダッド、アノニマ、デ、カピタル、バリアブレ | プロセス |
| GB0806422D0 (en) | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
| JP5337799B2 (ja) * | 2007-06-27 | 2013-11-06 | アーケマ・インコーポレイテッド | ヒドロフルオロオレフィンの製造方法 |
| US7795480B2 (en) * | 2007-07-25 | 2010-09-14 | Honeywell International Inc. | Method for producing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) |
| JP5136111B2 (ja) * | 2008-02-19 | 2013-02-06 | セントラル硝子株式会社 | フルオロオレフィンとフッ化水素の分離方法 |
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