TW201800374A - 製備氯化碳氫化合物之方法 - Google Patents
製備氯化碳氫化合物之方法 Download PDFInfo
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- TW201800374A TW201800374A TW106134154A TW106134154A TW201800374A TW 201800374 A TW201800374 A TW 201800374A TW 106134154 A TW106134154 A TW 106134154A TW 106134154 A TW106134154 A TW 106134154A TW 201800374 A TW201800374 A TW 201800374A
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- Prior art keywords
- product
- reaction
- pentachloropropane
- compound
- reactor
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 83
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 title abstract description 9
- 230000008569 process Effects 0.000 title description 41
- UMGQVBVEWTXECF-UHFFFAOYSA-N 1,1,2,3-tetrachloroprop-1-ene Chemical class ClCC(Cl)=C(Cl)Cl UMGQVBVEWTXECF-UHFFFAOYSA-N 0.000 claims abstract description 108
- ZXPCCXXSNUIVNK-UHFFFAOYSA-N 1,1,1,2,3-pentachloropropane Chemical compound ClCC(Cl)C(Cl)(Cl)Cl ZXPCCXXSNUIVNK-UHFFFAOYSA-N 0.000 claims abstract description 105
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims abstract description 71
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims abstract description 71
- 150000001336 alkenes Chemical class 0.000 claims abstract description 64
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 60
- -1 pentachloropropanes Chemical class 0.000 claims abstract description 59
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims abstract description 52
- ZDINGUUTWDGGFF-UHFFFAOYSA-N antimony(5+) Chemical compound [Sb+5] ZDINGUUTWDGGFF-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000000460 chlorine Substances 0.000 claims description 98
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 61
- 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 claims description 49
- 239000000758 substrate Substances 0.000 claims description 40
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 37
- 238000010438 heat treatment Methods 0.000 claims description 29
- 150000001785 cerium compounds Chemical class 0.000 claims description 20
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
- 150000002178 europium compounds Chemical class 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 6
- 150000002429 hydrazines Chemical class 0.000 claims description 6
- FAWGZAFXDJGWBB-UHFFFAOYSA-N antimony(3+) Chemical compound [Sb+3] FAWGZAFXDJGWBB-UHFFFAOYSA-N 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 238000011437 continuous method Methods 0.000 claims 1
- UTACNSITJSJFHA-UHFFFAOYSA-N 1,1,1,3-tetrachloropropane Chemical compound ClCCC(Cl)(Cl)Cl UTACNSITJSJFHA-UHFFFAOYSA-N 0.000 abstract description 60
- 238000002360 preparation method Methods 0.000 abstract description 18
- FEKGWIHDBVDVSM-UHFFFAOYSA-N 1,1,1,2-tetrachloropropane Chemical class CC(Cl)C(Cl)(Cl)Cl FEKGWIHDBVDVSM-UHFFFAOYSA-N 0.000 abstract description 10
- FTCVHAQNWWBTIV-UHFFFAOYSA-N 1,1,1,2,2-pentachloropropane Chemical class CC(Cl)(Cl)C(Cl)(Cl)Cl FTCVHAQNWWBTIV-UHFFFAOYSA-N 0.000 abstract description 9
- 150000001463 antimony compounds Chemical class 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 241
- 238000006243 chemical reaction Methods 0.000 description 219
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 105
- 238000004821 distillation Methods 0.000 description 95
- 229910052801 chlorine Inorganic materials 0.000 description 87
- 238000007033 dehydrochlorination reaction Methods 0.000 description 78
- 238000005660 chlorination reaction Methods 0.000 description 66
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 62
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 39
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 39
- 239000003054 catalyst Substances 0.000 description 32
- 239000012043 crude product Substances 0.000 description 32
- 150000003304 ruthenium compounds Chemical class 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
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- 230000015572 biosynthetic process Effects 0.000 description 27
- 238000004817 gas chromatography Methods 0.000 description 21
- 239000000376 reactant Substances 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
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- 230000000052 comparative effect Effects 0.000 description 13
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- 239000002243 precursor Substances 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- 238000000926 separation method Methods 0.000 description 12
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- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- 238000010923 batch production Methods 0.000 description 7
- 239000012527 feed solution Substances 0.000 description 7
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
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- 238000013019 agitation Methods 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000001273 butane Substances 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 229910000420 cerium oxide Inorganic materials 0.000 description 6
- 238000010924 continuous production Methods 0.000 description 6
- 150000001924 cycloalkanes Chemical class 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 6
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 150000001345 alkine derivatives Chemical class 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 150000001491 aromatic compounds Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 238000013461 design Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- GIDBEKINLBHYLA-UHFFFAOYSA-I pentachlororuthenium Chemical compound Cl[Ru](Cl)(Cl)(Cl)Cl GIDBEKINLBHYLA-UHFFFAOYSA-I 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- 229910052707 ruthenium Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 4
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- 230000007797 corrosion Effects 0.000 description 4
- 150000001925 cycloalkenes Chemical class 0.000 description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 4
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- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 4
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 238000000066 reactive distillation Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 4
- 239000012953 triphenylsulfonium Substances 0.000 description 4
- 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 3
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- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 3
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- XPIGFCKQOOBTLK-UHFFFAOYSA-N 1,1,3,3-tetrachloroprop-1-ene Chemical compound ClC(Cl)C=C(Cl)Cl XPIGFCKQOOBTLK-UHFFFAOYSA-N 0.000 description 2
- JFEVIPGMXQNRRF-UHFFFAOYSA-N 1,1,3-trichloroprop-1-ene Chemical compound ClCC=C(Cl)Cl JFEVIPGMXQNRRF-UHFFFAOYSA-N 0.000 description 2
- GVVUPGXFVJLPDE-UHFFFAOYSA-N 1,3,3,3-tetrachloroprop-1-ene Chemical compound ClC=CC(Cl)(Cl)Cl GVVUPGXFVJLPDE-UHFFFAOYSA-N 0.000 description 2
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- BBEAZDGZMVABIC-UHFFFAOYSA-N 1,1,1,3,3,3-hexachloropropane Chemical compound ClC(Cl)(Cl)CC(Cl)(Cl)Cl BBEAZDGZMVABIC-UHFFFAOYSA-N 0.000 description 1
- VVWFZKBKXPXGBH-UHFFFAOYSA-N 1,1,1,3,3-pentachloropropane Chemical compound ClC(Cl)CC(Cl)(Cl)Cl VVWFZKBKXPXGBH-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
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- 229920006362 Teflon® Polymers 0.000 description 1
- MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical compound CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 description 1
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- YQNJLSQOZXCWPG-UHFFFAOYSA-N [Cl-].[Cl-].C(CCC)[PH+](CCCC)CCCC.C(CCC)[PH+](CCCC)CCCC Chemical compound [Cl-].[Cl-].C(CCC)[PH+](CCCC)CCCC.C(CCC)[PH+](CCCC)CCCC YQNJLSQOZXCWPG-UHFFFAOYSA-N 0.000 description 1
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- CZPQOMDTTZCPTK-UHFFFAOYSA-N [He].Cl.Cl.Cl.Cl.Cl Chemical compound [He].Cl.Cl.Cl.Cl.Cl CZPQOMDTTZCPTK-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000002355 alkine group Chemical group 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 1
- 150000001622 bismuth compounds Chemical class 0.000 description 1
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- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 1
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- 239000004927 clay Substances 0.000 description 1
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- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
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- ZPWOOKQUDFIEIX-UHFFFAOYSA-N cyclooctyne Chemical compound C1CCCC#CCC1 ZPWOOKQUDFIEIX-UHFFFAOYSA-N 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
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- 239000000945 filler Substances 0.000 description 1
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- 238000001914 filtration Methods 0.000 description 1
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- YVXHZKKCZYLQOP-UHFFFAOYSA-N hept-1-yne Chemical compound CCCCCC#C YVXHZKKCZYLQOP-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
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- 239000003507 refrigerant Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-O tributylphosphanium Chemical compound CCCC[PH+](CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-O 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- RXPQRKFMDQNODS-UHFFFAOYSA-N tripropyl phosphate Chemical compound CCCOP(=O)(OCCC)OCCC RXPQRKFMDQNODS-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical class [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/10—Chlorides
-
- 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
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/275—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of hydrocarbons and halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
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| US201361789786P | 2013-03-15 | 2013-03-15 | |
| US61/789,786 | 2013-03-15 | ||
| US14/060,957 | 2013-10-23 | ||
| US14/060,957 US8889930B2 (en) | 2013-01-22 | 2013-10-23 | Process for producing chlorinated hydrocarbons |
Publications (1)
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|---|---|
| TW201800374A true TW201800374A (zh) | 2018-01-01 |
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| TW106134154A TW201800374A (zh) | 2013-01-22 | 2014-01-03 | 製備氯化碳氫化合物之方法 |
| TW103100233A TWI617535B (zh) | 2013-01-22 | 2014-01-03 | 製備氯化碳氫化合物之方法 |
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| TW103100233A TWI617535B (zh) | 2013-01-22 | 2014-01-03 | 製備氯化碳氫化合物之方法 |
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| US (3) | US8889930B2 (enExample) |
| EP (1) | EP2948420B1 (enExample) |
| JP (1) | JP6258973B2 (enExample) |
| CN (1) | CN105164091A (enExample) |
| TW (2) | TW201800374A (enExample) |
| WO (1) | WO2014116562A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9067858B2 (en) * | 2013-02-12 | 2015-06-30 | Occidental Chemical Corporation | Methods for recovering 1,1,1,2,3-pentachloropropane |
| US9139497B2 (en) * | 2013-10-23 | 2015-09-22 | Axiall Ohio, Inc. | Process for producing chlorinated hydrocarbons in the presence of a polyvalent bismuth compound |
| FR3027303B1 (fr) * | 2014-10-16 | 2016-10-07 | Arkema France | Compositions a base de 1,1,1,2,3-pentachloropropane |
| US10081582B2 (en) | 2014-10-22 | 2018-09-25 | Eagle Us 2 Llc | Process for producing chlorinated hydrocarbons in the presence of a polyvalent molybdenum compound |
| US20160115106A1 (en) * | 2014-10-22 | 2016-04-28 | Axiall Ohio, Inc. | Stabilization of Chlorinated Olefins |
| FR3036398B1 (fr) * | 2015-05-22 | 2019-05-03 | Arkema France | Compositions a base de 1,1,3,3-tetrachloropropene |
| EP3337777B1 (en) | 2015-08-19 | 2025-01-01 | SPOLCHEMlE Zebra, a.s. | Process for producing c3 chlorinated alkane and alkene compounds |
| WO2017177988A1 (en) | 2016-04-13 | 2017-10-19 | Spolek Pro Chemickou A Hutni Vyrobu, Akciova Spolecnost | Process |
| FI3490963T3 (fi) | 2016-07-26 | 2023-12-21 | Occidental Chem Co | Menetelmä kloorattujen hiilivetyjen tuottamiseksi |
| JP7500430B2 (ja) * | 2018-04-03 | 2024-06-17 | ブルー キューブ アイピー エルエルシー | ハロゲン化アルカンの触媒化脱ハロゲン化水素によりハロゲン化アルケンを生成する方法 |
| FR3081158B1 (fr) | 2018-05-16 | 2020-07-31 | Arkema France | Procede de production du 1-chloro-3,3,3-trifluoropropene. |
| FR3083232B1 (fr) | 2018-06-27 | 2021-11-12 | Arkema France | Procede de production du 1-chloro-3,3,3-trifluoropropene |
| FR3086287B1 (fr) | 2018-09-26 | 2020-09-18 | Arkema France | Stabilisation du 1-chloro-3,3,3-trifluoropropene |
| 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 |
| CN111604041B (zh) * | 2020-06-18 | 2023-04-07 | 大连九信精细化工有限公司 | 一种γ-氧化铝改性催化剂、其制备方法及在合成1,1,3-三氯丙烯中的应用 |
| CN115108882B (zh) * | 2022-06-07 | 2024-04-12 | 浙江衢化氟化学有限公司 | 一种1,1,1,2,3-五氯丙烷的连续制备方法 |
| CN115722255B (zh) * | 2022-10-13 | 2024-08-27 | 浙江衢化氟化学有限公司 | 一种用于生产1,1,1,2,3-五氯丙烷的负载型催化剂及其制备方法和应用 |
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|---|---|---|---|---|
| CH207500A (de) | 1937-04-17 | 1939-11-15 | Consortium Elektrochem Ind | Verfahren zur Herstellung der Chlorkohlenstoffverbindung C4CI6. |
| US2765349A (en) | 1955-04-05 | 1956-10-02 | Ethyl Corp | Dehydrochlorination process |
| US2894044A (en) | 1956-02-16 | 1959-07-07 | Monsanto Chemicals | Preparation of 1, 1-dichloro-1-fluoroethane |
| US3732322A (en) * | 1969-08-19 | 1973-05-08 | Toa Gosei Chem Ind | Process for the production of chloroethylenes |
| AR219135A1 (es) | 1977-11-18 | 1980-07-31 | Goodrich Co B F | Procedimiento para producir cloruro de vinilo |
| US4535194A (en) | 1983-07-06 | 1985-08-13 | Monsanto Co. | Process for producing 1,1,2,3-tetrachloropropene |
| EP0131561B1 (en) | 1983-07-06 | 1986-10-15 | Monsanto Company | Process for producing monoadducts of olefins and telogens reactive therewith |
| US4650914A (en) | 1983-07-06 | 1987-03-17 | Monsanto Company | Process for producing 1,1,2,3-tetrachloropropene |
| US5608127A (en) | 1990-02-09 | 1997-03-04 | E. I. Dupont De Nemours And Company | Halogen exchange process for manufacture of hydrochlorofluoropropanes |
| US5902914A (en) | 1995-08-14 | 1999-05-11 | Alliedsignal Inc. | Process for the preparation of halogenated alkanes |
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2013
- 2013-10-23 US US14/060,957 patent/US8889930B2/en active Active
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2014
- 2014-01-03 TW TW106134154A patent/TW201800374A/zh unknown
- 2014-01-03 TW TW103100233A patent/TWI617535B/zh active
- 2014-01-21 EP EP14703493.8A patent/EP2948420B1/en active Active
- 2014-01-21 CN CN201480017362.XA patent/CN105164091A/zh active Pending
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| TW201434799A (zh) | 2014-09-16 |
| EP2948420B1 (en) | 2018-08-08 |
| EP2948420A1 (en) | 2015-12-02 |
| WO2014116562A1 (en) | 2014-07-31 |
| US20150031925A1 (en) | 2015-01-29 |
| JP6258973B2 (ja) | 2018-01-10 |
| JP2016507518A (ja) | 2016-03-10 |
| USRE47429E1 (en) | 2019-06-11 |
| US20140206911A1 (en) | 2014-07-24 |
| TWI617535B (zh) | 2018-03-11 |
| US8889930B2 (en) | 2014-11-18 |
| CN105164091A (zh) | 2015-12-16 |
| US9255048B2 (en) | 2016-02-09 |
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