JP5498381B2 - フッ素化有機化合物を製造する方法 - Google Patents
フッ素化有機化合物を製造する方法 Download PDFInfo
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- JP5498381B2 JP5498381B2 JP2010518402A JP2010518402A JP5498381B2 JP 5498381 B2 JP5498381 B2 JP 5498381B2 JP 2010518402 A JP2010518402 A JP 2010518402A JP 2010518402 A JP2010518402 A JP 2010518402A JP 5498381 B2 JP5498381 B2 JP 5498381B2
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- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 150000002894 organic compounds Chemical class 0.000 title claims description 3
- 239000003054 catalyst Substances 0.000 claims description 76
- 239000003381 stabilizer Substances 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 36
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 33
- UMGQVBVEWTXECF-UHFFFAOYSA-N 1,1,2,3-tetrachloroprop-1-ene Chemical compound ClCC(Cl)=C(Cl)Cl UMGQVBVEWTXECF-UHFFFAOYSA-N 0.000 claims description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 claims description 12
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 12
- 229940043279 diisopropylamine Drugs 0.000 claims description 11
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 9
- 229910016569 AlF 3 Inorganic materials 0.000 claims description 9
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 claims description 8
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 claims description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000005844 Thymol Substances 0.000 claims description 4
- 150000001412 amines Chemical group 0.000 claims description 4
- 229910052804 chromium Inorganic materials 0.000 claims description 4
- 229960000790 thymol Drugs 0.000 claims description 4
- 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 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000002140 halogenating effect Effects 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 36
- 239000011651 chromium Substances 0.000 description 22
- 230000008569 process Effects 0.000 description 19
- 238000003682 fluorination reaction Methods 0.000 description 15
- 239000007789 gas Substances 0.000 description 15
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 13
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 12
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- OQISUJXQFPPARX-UHFFFAOYSA-N 2-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Cl)=C OQISUJXQFPPARX-UHFFFAOYSA-N 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- ZXPCCXXSNUIVNK-UHFFFAOYSA-N 1,1,1,2,3-pentachloropropane Chemical compound ClCC(Cl)C(Cl)(Cl)Cl ZXPCCXXSNUIVNK-UHFFFAOYSA-N 0.000 description 5
- PQUUGVDRLWLNGR-UHFFFAOYSA-N 2,3,3,3-tetrachloroprop-1-ene Chemical compound ClC(=C)C(Cl)(Cl)Cl PQUUGVDRLWLNGR-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000012025 fluorinating agent Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 229910000792 Monel Inorganic materials 0.000 description 4
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
- 229910000423 chromium oxide Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 238000010574 gas phase reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 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 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 238000004939 coking Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- NRZWYNLTFLDQQX-UHFFFAOYSA-N p-tert-Amylphenol Chemical compound CCC(C)(C)C1=CC=C(O)C=C1 NRZWYNLTFLDQQX-UHFFFAOYSA-N 0.000 description 3
- 230000002572 peristaltic effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- FFTOUVYEKNGDCM-OWOJBTEDSA-N (e)-1,3,3-trifluoroprop-1-ene Chemical compound F\C=C\C(F)F FFTOUVYEKNGDCM-OWOJBTEDSA-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- 239000004088 foaming agent Substances 0.000 description 2
- -1 heat transfer media Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000003507 refrigerant Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 239000012808 vapor phase Substances 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
- PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical compound FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 description 1
- YHLIEGBCOUQKHU-UHFFFAOYSA-N 1,1-difluoroprop-1-ene Chemical compound CC=C(F)F YHLIEGBCOUQKHU-UHFFFAOYSA-N 0.000 description 1
- XPRPUIGRQWCMGD-UHFFFAOYSA-N 2,3-dichloro-1,1-difluoroprop-1-ene Chemical compound FC(F)=C(Cl)CCl XPRPUIGRQWCMGD-UHFFFAOYSA-N 0.000 description 1
- SMCNZLDHTZESTK-UHFFFAOYSA-N 2-chloro-1,1,1,2-tetrafluoropropane Chemical compound CC(F)(Cl)C(F)(F)F SMCNZLDHTZESTK-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- 229910000975 Carbon steel Inorganic materials 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 230000004075 alteration Effects 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000010962 carbon steel Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 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
- 238000010924 continuous production Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 235000013980 iron oxide 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
- 230000007774 longterm Effects 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
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 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
- 238000005191 phase separation Methods 0.000 description 1
- 230000000704 physical effect Effects 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/06—Preparation of halogenated hydrocarbons by addition of halogens combined with replacement of hydrogen atoms by halogens
-
- 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
- C07C17/20—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
- C07C17/25—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
- C07C17/42—Use of additives, e.g. for stabilisation
-
- 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
Description
CH2ClCCl=CCl2+3HF→CF3CCl=CH2+3HCl
これらの実施例では、安定剤の非存在下での気相反応におけるCH2ClCCl=CCl2へのフッ化水素の添加を説明する。これは以下の反応スキームで示される:
CH2ClCCl=CCl2+3HF→CF3CCl=CH2+3HCl
これらの実施例では、安定剤の存在下での気相反応におけるCH2ClCCl=CCl2へのフッ化水素の添加を説明する。
これらの実施例では、炭素鋼、ステンレス鋼およびモネル金属片の存在下に種々の安定剤を用い、種々の温度で実施したCH2ClCCl=CCl2の安定性試験を説明する。それぞれの安定剤は濃度100ppmで用い、室温から100℃および/または150℃まで加熱した。次にそれぞれの安定剤を結果に従って順位付けし、最も安定性の悪い組合せを評点1、150℃において最も安定な組合せを評点10とした。結果を以下の表IIIに示す。
この実施例では、安定剤としてジイソプロピルアミンを用い、触媒接触時間を約2秒と比較的長くした気相反応におけるCH2ClCCl=CCl2へのフッ化水素の添加を説明する。2.54cm(1インチ)のモネル製管状反応器に、大気圧下、300℃の温度で320ccの新鮮なCr2O3触媒を仕込んだ。有機供給原料(CH2ClCCl=CCl2)およびフッ化水素を、それぞれ約0.11kg/時間(0.24ポンド/時間)および約0.25kg/時間(0.55ポンド/時間)の速度で蠕動ポンプを通じて反応器に供給し、HF/有機物モル比を約20:1とした。CH2ClCCl=CCl2供給原料に10ppmの量のジイソプロピルアミン安定剤を加えた。有機供給原料、HFおよび安定剤を含むガス流を、約85時間までの間にわたって触媒床に通した。Cr2O3床を通した接触時間は約2.05秒であった。
この実施例では、安定剤としてジイソプロピルアミンを用い、触媒接触時間を約8〜約10秒と比較的長くした気相反応におけるCH2ClCCl=CCl2へのフッ化水素の添加を説明する。5.08cm(2インチ)のモネル製管状反応器に、大気圧下、最初は200℃の温度で1800ccの新鮮なCr2O3触媒を仕込み、そして225℃に、次に250℃に昇温した。有機供給原料(CH2ClCCl=CCl2)およびフッ化水素を、それぞれ約0.16kg/時間(0.35ポンド/時間)および約0.35kg/時間(0.78ポンド/時間)の速度で蠕動ポンプを通じて反応器に供給し、HF/有機物モル比を約20:1とした。CH2ClCCl=CCl2に10ppmの量のジイソプロピルアミン安定剤を加えた。有機供給原料、HFおよび安定剤を含むガス流を、約278時間までの間にわたって触媒床に通した。Cr2O3床を通した接触時間は約8〜10秒であった。
この実施例では、3種の異なったTCP供給原料を用いた以下の反応:
1,1,2,3−テトラクロロプロペン(TCP)+HF→1233xf+3HCl
の間のCr2O3触媒の安定性を実証する。実験Aでは非安定化TCPを用い、実験Bでは13ppmのp−tap(4−tert−アミルフェノール)で安定化したTCPを用い、実験Cでは13ppmのメトキシヒドロキノンで安定化したTCPを用いた。これら3つの実験のすべてで、310cc(約448g)の新たに前処理したCr2O3触媒を仕込んだ2.54cm(1インチ)の反応器を用いた。触媒床のホットスポット反応温度は、すべての実験について実験の期間中243〜254℃の範囲に保たれていた。また、HFおよびTCPの流量をすべての実験について同一とし、最初の触媒の生産性および接触時間を3実験すべてについて同一に保った。すべての実験は大気圧下で行った。
[本発明の態様]
1.テトラクロロプロペンおよびペンタクロロプロパンからなる群から選択される少なくとも1種のクロロカーボンを、C3ハロオレフィンを生成するために有効な条件下で、少なくとも1種の触媒および少なくとも1種の安定剤の存在下に、ハロゲン化剤と接触させることを含む、フッ素化有機化合物を製造する方法。
2.前記C3ハロオレフィンが2−クロロ−3,3,3−トリフルオロプロペンである、1に記載の方法。
3.前記クロロカーボンが、1,1,2,3−テトラクロロプロペン、2,3,3,3−テトラクロロプロペン、1,1,1,2,3−ペンタクロロプロパンからなる群から選択される少なくとも1種の化合物である、2に記載の方法。
4.前記ハロゲン化剤がフッ化水素を含む、1に記載の方法。
5.前記の接触させる工程が、前記接触工程の少なくとも一部を気相で実施することを含む、1に記載の方法。
6.前記少なくとも1種のフッ素化触媒が、Cr2O3、FeCl3/C、Cr2O3/Al2O3、Cr2O3/AlF3、Cr2O3/炭素、CoCl2/Cr2O3/Al2O3、NiCl2/Cr2O3/Al2O3、CoCl2/AlF3、NiCl2/AlF3およびそれらの組合せからなる群から選択される、1に記載の方法。
7.前記安定剤が、トリエチルアミンおよびジイソプロピルアミンからなる群から選択されるアミン安定剤を含む、1に記載の方法。
8.前記安定剤が、メトキシヒドロキノンおよび4−メトキシフェノール(HQMME)からなる群から選択されるヒドロキノン安定剤を含む、1に記載の方法。
9.前記安定剤が、p−tap(4−tert−アミルフェノール)、メトキシヒドロキノン、4−メトキシフェノール(HQMME)、トリエチルアミン、ジイソプロピルアミン、ブチルヒドロキシアニソール(BHA)、チモールおよびそれらの組合せからなる群から選択される、1に記載の方法。
10.前記安定剤の濃度が約300ppm未満である、1に記載の方法。
Claims (3)
- テトラクロロプロペンおよびペンタクロロプロパンからなる群から選択される少なくとも1種のクロロカーボンを、C3ハロオレフィンを生成するために、少なくとも1種の触媒および少なくとも1種の安定剤の存在下に、ハロゲン化剤と接触させることを含む、フッ素化有機化合物を製造する方法であって、
前記少なくとも1種の安定剤が、アミン安定剤、ヒドロキノン安定剤、メトキシヒドロキノン、トリエチルアミン、ジイソプロピルアミン、ブチルヒドロキシアニソール(BHA)、チモールおよびそれらの組合せからなる群から選択される、方法。 - 前記少なくとも1種の触媒が、Cr2O3、FeCl3/C、Cr2O3/Al2O3、Cr2O3/AlF3、Cr2O3/炭素、CoCl2/Cr2O3/Al2O3、NiCl2/Cr2O3/Al2O3、CoCl2/AlF3、NiCl2/AlF3およびそれらの組合せからなる群から選択され、
前記安定剤が、アミン安定剤、ヒドロキノン安定剤、メトキシヒドロキノン、トリエチルアミン、ジイソプロピルアミン、ブチルヒドロキシアニソール(BHA)、チモールおよびそれらの組合せからなる群から選択される、請求項1に記載の方法。 - 前記安定剤の濃度が300ppm未満である、請求項2に記載の方法。
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EP3196182B1 (en) | 2021-09-01 |
US20110004035A1 (en) | 2011-01-06 |
EP2170786B1 (en) | 2017-03-08 |
ES2893702T3 (es) | 2022-02-09 |
KR101553543B1 (ko) | 2015-09-16 |
US9573867B2 (en) | 2017-02-21 |
US20120136182A1 (en) | 2012-05-31 |
US7795480B2 (en) | 2010-09-14 |
EP3196182A1 (en) | 2017-07-26 |
CN101874009A (zh) | 2010-10-27 |
ES2625141T3 (es) | 2017-07-18 |
US20160194261A1 (en) | 2016-07-07 |
EP2170786A4 (en) | 2015-04-15 |
US8367878B2 (en) | 2013-02-05 |
EP2170786B2 (en) | 2019-12-18 |
KR20100039352A (ko) | 2010-04-15 |
JP2010534680A (ja) | 2010-11-11 |
CN101874009B (zh) | 2014-07-16 |
MX2010000768A (es) | 2010-03-04 |
EP2170786A1 (en) | 2010-04-07 |
US20130197282A1 (en) | 2013-08-01 |
ES2625141T5 (es) | 2020-07-01 |
WO2009015317A1 (en) | 2009-01-29 |
US20170233314A1 (en) | 2017-08-17 |
US20090030244A1 (en) | 2009-01-29 |
US9227893B2 (en) | 2016-01-05 |
US20150105595A1 (en) | 2015-04-16 |
US8119845B2 (en) | 2012-02-21 |
US9902671B2 (en) | 2018-02-27 |
US8912368B2 (en) | 2014-12-16 |
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