JP5450426B2 - プロパン及びイソブタンのアンモ酸化又は酸化方法 - Google Patents
プロパン及びイソブタンのアンモ酸化又は酸化方法 Download PDFInfo
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- JP5450426B2 JP5450426B2 JP2010528872A JP2010528872A JP5450426B2 JP 5450426 B2 JP5450426 B2 JP 5450426B2 JP 2010528872 A JP2010528872 A JP 2010528872A JP 2010528872 A JP2010528872 A JP 2010528872A JP 5450426 B2 JP5450426 B2 JP 5450426B2
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- catalyst
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- antimony
- mixed metal
- metal oxide
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- 238000000034 method Methods 0.000 title claims description 78
- 238000007254 oxidation reaction Methods 0.000 title claims description 37
- 230000003647 oxidation Effects 0.000 title claims description 36
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 title description 60
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 title description 42
- 239000001294 propane Substances 0.000 title description 30
- 239000001282 iso-butane Substances 0.000 title description 21
- 239000003054 catalyst Substances 0.000 claims description 279
- 239000000203 mixture Substances 0.000 claims description 202
- 229910003455 mixed metal oxide Inorganic materials 0.000 claims description 71
- 239000003607 modifier Substances 0.000 claims description 58
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- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 48
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 48
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- 229910052750 molybdenum Inorganic materials 0.000 claims description 42
- 239000011733 molybdenum Substances 0.000 claims description 42
- 229910052758 niobium Inorganic materials 0.000 claims description 40
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 40
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 36
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- 229910052787 antimony Inorganic materials 0.000 claims description 30
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- 238000002156 mixing Methods 0.000 claims description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 25
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- 229920006395 saturated elastomer Polymers 0.000 claims description 20
- 229910021529 ammonia Inorganic materials 0.000 claims description 18
- 229910052721 tungsten Inorganic materials 0.000 claims description 18
- 229910052726 zirconium Inorganic materials 0.000 claims description 18
- 229910052684 Cerium Inorganic materials 0.000 claims description 17
- 238000001027 hydrothermal synthesis Methods 0.000 claims description 17
- 229910052714 tellurium Inorganic materials 0.000 claims description 17
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- 229910052746 lanthanum Inorganic materials 0.000 claims description 16
- 229910052744 lithium Inorganic materials 0.000 claims description 16
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- 229910052691 Erbium Inorganic materials 0.000 claims description 15
- 229910052693 Europium Inorganic materials 0.000 claims description 15
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- 229910052689 Holmium Inorganic materials 0.000 claims description 15
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- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Inorganic materials O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 claims description 11
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 8
- 239000010936 titanium Substances 0.000 claims description 8
- XUGISPSHIFXEHZ-GPJXBBLFSA-N [(3r,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C1C=C2C[C@H](OC(C)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 XUGISPSHIFXEHZ-GPJXBBLFSA-N 0.000 claims description 7
- 238000005470 impregnation Methods 0.000 claims description 7
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- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 6
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- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 5
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 5
- 239000010937 tungsten Substances 0.000 claims description 5
- AHBGXHAWSHTPOM-UHFFFAOYSA-N 1,3,2$l^{4},4$l^{4}-dioxadistibetane 2,4-dioxide Chemical compound O=[Sb]O[Sb](=O)=O AHBGXHAWSHTPOM-UHFFFAOYSA-N 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- 229910000410 antimony oxide Inorganic materials 0.000 claims description 4
- 229910000411 antimony tetroxide Inorganic materials 0.000 claims description 4
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 claims description 4
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 claims description 4
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 4
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims description 4
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 4
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 4
- KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 claims description 4
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 claims description 4
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims description 4
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 claims description 4
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 claims description 4
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims description 4
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 claims description 4
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 53
- 150000001875 compounds Chemical class 0.000 description 49
- 150000002822 niobium compounds Chemical class 0.000 description 28
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 23
- 239000007864 aqueous solution Substances 0.000 description 23
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 19
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- 239000007787 solid Substances 0.000 description 17
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- 238000010438 heat treatment Methods 0.000 description 15
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 11
- 238000001035 drying Methods 0.000 description 11
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 10
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
- 238000010304 firing Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 150000003609 titanium compounds Chemical class 0.000 description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
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- 150000001639 boron compounds Chemical class 0.000 description 9
- 150000001785 cerium compounds Chemical class 0.000 description 9
- 150000002291 germanium compounds Chemical class 0.000 description 9
- 150000002642 lithium compounds Chemical class 0.000 description 9
- 150000002798 neodymium compounds Chemical class 0.000 description 9
- 239000000047 product Substances 0.000 description 9
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- 150000003343 selenium compounds Chemical class 0.000 description 8
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
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- 229910001947 lithium oxide Inorganic materials 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
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- PLDDOISOJJCEMH-UHFFFAOYSA-N neodymium(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Nd+3].[Nd+3] PLDDOISOJJCEMH-UHFFFAOYSA-N 0.000 description 6
- 150000003018 phosphorus compounds Chemical class 0.000 description 6
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- JCCYXJAEFHYHPP-OLXYHTOASA-L dilithium;(2r,3r)-2,3-dihydroxybutanedioate Chemical compound [Li+].[Li+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O JCCYXJAEFHYHPP-OLXYHTOASA-L 0.000 description 4
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- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical group [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 3
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- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 3
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- GMQPBTKWMZBSCT-UHFFFAOYSA-K neodymium(3+);triacetate;hydrate Chemical compound O.[Nd+3].CC([O-])=O.CC([O-])=O.CC([O-])=O GMQPBTKWMZBSCT-UHFFFAOYSA-K 0.000 description 3
- ATINCSYRHURBSP-UHFFFAOYSA-K neodymium(iii) chloride Chemical compound Cl[Nd](Cl)Cl ATINCSYRHURBSP-UHFFFAOYSA-K 0.000 description 3
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- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- GAPRPFRDVCCCHR-UHFFFAOYSA-N 3-bromoprop-1-ynyl(trimethyl)silane Chemical compound C[Si](C)(C)C#CCBr GAPRPFRDVCCCHR-UHFFFAOYSA-N 0.000 description 1
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- 229910005793 GeO 2 Inorganic materials 0.000 description 1
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- 238000005299 abrasion Methods 0.000 description 1
- QPBWWHHFCKKZJQ-UHFFFAOYSA-N acetic acid;praseodymium;hydrate Chemical compound O.[Pr].CC(O)=O.CC(O)=O.CC(O)=O QPBWWHHFCKKZJQ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 229910000379 antimony sulfate Inorganic materials 0.000 description 1
- MVMLTMBYNXHXFI-UHFFFAOYSA-H antimony(3+);trisulfate Chemical compound [Sb+3].[Sb+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O MVMLTMBYNXHXFI-UHFFFAOYSA-H 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- JITPFBSJZPOLGT-UHFFFAOYSA-N cerium(3+);propan-2-olate Chemical compound [Ce+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] JITPFBSJZPOLGT-UHFFFAOYSA-N 0.000 description 1
- AERUOEZHIAYQQL-UHFFFAOYSA-K cerium(3+);triacetate;hydrate Chemical compound O.[Ce+3].CC([O-])=O.CC([O-])=O.CC([O-])=O AERUOEZHIAYQQL-UHFFFAOYSA-K 0.000 description 1
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- 238000005859 coupling reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
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- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
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- 238000000151 deposition Methods 0.000 description 1
- JVLRYPRBKSMEBF-UHFFFAOYSA-K diacetyloxystibanyl acetate Chemical compound [Sb+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JVLRYPRBKSMEBF-UHFFFAOYSA-K 0.000 description 1
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 1
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- 238000007599 discharging Methods 0.000 description 1
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- 238000004821 distillation Methods 0.000 description 1
- XPEKDHWAGKXPST-UHFFFAOYSA-N dysprosium(3+);propan-2-olate Chemical compound [Dy+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] XPEKDHWAGKXPST-UHFFFAOYSA-N 0.000 description 1
- AAGMOWMTSATFBV-UHFFFAOYSA-K dysprosium(3+);triacetate;hydrate Chemical compound O.[Dy+3].CC([O-])=O.CC([O-])=O.CC([O-])=O AAGMOWMTSATFBV-UHFFFAOYSA-K 0.000 description 1
- BOXVSFHSLKQLNZ-UHFFFAOYSA-K dysprosium(iii) chloride Chemical compound Cl[Dy](Cl)Cl BOXVSFHSLKQLNZ-UHFFFAOYSA-K 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- VOCNVTAXVORJBI-UHFFFAOYSA-N erbium(3+);propan-2-olate Chemical compound [Er+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] VOCNVTAXVORJBI-UHFFFAOYSA-N 0.000 description 1
- DBUHPIKTDUMWTR-UHFFFAOYSA-K erbium(3+);triacetate Chemical compound [Er+3].CC([O-])=O.CC([O-])=O.CC([O-])=O DBUHPIKTDUMWTR-UHFFFAOYSA-K 0.000 description 1
- HDGGAKOVUDZYES-UHFFFAOYSA-K erbium(iii) chloride Chemical compound Cl[Er](Cl)Cl HDGGAKOVUDZYES-UHFFFAOYSA-K 0.000 description 1
- JGJIXMFWDPQYRL-UHFFFAOYSA-K europium(3+);triacetate;hydrate Chemical compound O.[Eu+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JGJIXMFWDPQYRL-UHFFFAOYSA-K 0.000 description 1
- NNMXSTWQJRPBJZ-UHFFFAOYSA-K europium(iii) chloride Chemical compound Cl[Eu](Cl)Cl NNMXSTWQJRPBJZ-UHFFFAOYSA-K 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
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- GXCUBNRUECGTSC-UHFFFAOYSA-K gadolinium(3+);triacetate;hydrate Chemical compound O.[Gd+3].CC([O-])=O.CC([O-])=O.CC([O-])=O GXCUBNRUECGTSC-UHFFFAOYSA-K 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
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- 239000001307 helium Substances 0.000 description 1
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- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- LCCGYXRQAXROOW-UHFFFAOYSA-K holmium(3+);triacetate;hydrate Chemical compound O.[Ho+3].CC([O-])=O.CC([O-])=O.CC([O-])=O LCCGYXRQAXROOW-UHFFFAOYSA-K 0.000 description 1
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- 239000012535 impurity Substances 0.000 description 1
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- JLRJWBUSTKIQQH-UHFFFAOYSA-K lanthanum(3+);triacetate Chemical compound [La+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JLRJWBUSTKIQQH-UHFFFAOYSA-K 0.000 description 1
- ICAKDTKJOYSXGC-UHFFFAOYSA-K lanthanum(iii) chloride Chemical compound Cl[La](Cl)Cl ICAKDTKJOYSXGC-UHFFFAOYSA-K 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
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- 239000000463 material Substances 0.000 description 1
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- 238000000465 moulding Methods 0.000 description 1
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- ZTILUDNICMILKJ-UHFFFAOYSA-N niobium(v) ethoxide Chemical compound CCO[Nb](OCC)(OCC)(OCC)OCC ZTILUDNICMILKJ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- MPARYNQUYZOBJM-UHFFFAOYSA-N oxo(oxolutetiooxy)lutetium Chemical compound O=[Lu]O[Lu]=O MPARYNQUYZOBJM-UHFFFAOYSA-N 0.000 description 1
- MMKQUGHLEMYQSG-UHFFFAOYSA-N oxygen(2-);praseodymium(3+) Chemical compound [O-2].[O-2].[O-2].[Pr+3].[Pr+3] MMKQUGHLEMYQSG-UHFFFAOYSA-N 0.000 description 1
- UZLYXNNZYFBAQO-UHFFFAOYSA-N oxygen(2-);ytterbium(3+) Chemical compound [O-2].[O-2].[O-2].[Yb+3].[Yb+3] UZLYXNNZYFBAQO-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
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- UMIVUKFKISBKQB-UHFFFAOYSA-N praseodymium(3+);propan-2-olate Chemical compound [Pr+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] UMIVUKFKISBKQB-UHFFFAOYSA-N 0.000 description 1
- LHBNLZDGIPPZLL-UHFFFAOYSA-K praseodymium(iii) chloride Chemical compound Cl[Pr](Cl)Cl LHBNLZDGIPPZLL-UHFFFAOYSA-K 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- HJCRVWSKQNDSPZ-UHFFFAOYSA-N propan-2-olate;samarium(3+) Chemical compound [Sm+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] HJCRVWSKQNDSPZ-UHFFFAOYSA-N 0.000 description 1
- RAKJHSBPOPJWKI-UHFFFAOYSA-N propan-2-olate;ytterbium(3+) Chemical compound [Yb+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] RAKJHSBPOPJWKI-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- LKSVMAKMHXTSQX-UHFFFAOYSA-K samarium(3+);triacetate;hydrate Chemical compound O.[Sm+3].CC([O-])=O.CC([O-])=O.CC([O-])=O LKSVMAKMHXTSQX-UHFFFAOYSA-K 0.000 description 1
- BHXBZLPMVFUQBQ-UHFFFAOYSA-K samarium(iii) chloride Chemical compound Cl[Sm](Cl)Cl BHXBZLPMVFUQBQ-UHFFFAOYSA-K 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- JQBILSNVGUAPMM-UHFFFAOYSA-K terbium(3+);triacetate Chemical compound [Tb+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JQBILSNVGUAPMM-UHFFFAOYSA-K 0.000 description 1
- GFISHBQNVWAVFU-UHFFFAOYSA-K terbium(iii) chloride Chemical compound Cl[Tb](Cl)Cl GFISHBQNVWAVFU-UHFFFAOYSA-K 0.000 description 1
- SCRZPWWVSXWCMC-UHFFFAOYSA-N terbium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[Tb+3].[Tb+3] SCRZPWWVSXWCMC-UHFFFAOYSA-N 0.000 description 1
- FRNOGLGSGLTDKL-UHFFFAOYSA-N thulium atom Chemical compound [Tm] FRNOGLGSGLTDKL-UHFFFAOYSA-N 0.000 description 1
- SNMVVAHJCCXTQR-UHFFFAOYSA-K thulium(3+);triacetate Chemical compound [Tm+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SNMVVAHJCCXTQR-UHFFFAOYSA-K 0.000 description 1
- ILOTUXNTERMOJL-UHFFFAOYSA-K thulium(iii) chloride Chemical compound Cl[Tm](Cl)Cl ILOTUXNTERMOJL-UHFFFAOYSA-K 0.000 description 1
- PYOOBRULIYNHJR-UHFFFAOYSA-K trichloroholmium Chemical compound Cl[Ho](Cl)Cl PYOOBRULIYNHJR-UHFFFAOYSA-K 0.000 description 1
- 230000005514 two-phase flow Effects 0.000 description 1
- UUUGYDOQQLOJQA-UHFFFAOYSA-L vanadyl sulfate Chemical compound [V+2]=O.[O-]S([O-])(=O)=O UUUGYDOQQLOJQA-UHFFFAOYSA-L 0.000 description 1
- 229940041260 vanadyl sulfate Drugs 0.000 description 1
- 229910000352 vanadyl sulfate Inorganic materials 0.000 description 1
- 229910003454 ytterbium oxide Inorganic materials 0.000 description 1
- 229940075624 ytterbium oxide Drugs 0.000 description 1
- OSCVBYCJUSOYPN-UHFFFAOYSA-K ytterbium(3+);triacetate Chemical compound [Yb+3].CC([O-])=O.CC([O-])=O.CC([O-])=O OSCVBYCJUSOYPN-UHFFFAOYSA-K 0.000 description 1
- CKLHRQNQYIJFFX-UHFFFAOYSA-K ytterbium(III) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Yb+3] CKLHRQNQYIJFFX-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/24—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/24—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons
- C07C253/26—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons containing carbon-to-carbon multiple bonds, e.g. unsaturated aldehydes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/215—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of saturated hydrocarbyl groups
-
- 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
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
-
- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97928507P | 2007-10-11 | 2007-10-11 | |
| US97927607P | 2007-10-11 | 2007-10-11 | |
| US60/979,285 | 2007-10-11 | ||
| US60/979,276 | 2007-10-11 | ||
| PCT/US2008/011551 WO2009048553A2 (en) | 2007-10-11 | 2008-10-07 | Process for the ammoxidation or oxidation of propane and isobutane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011500564A JP2011500564A (ja) | 2011-01-06 |
| JP5450426B2 true JP5450426B2 (ja) | 2014-03-26 |
Family
ID=40342454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010528872A Expired - Fee Related JP5450426B2 (ja) | 2007-10-11 | 2008-10-07 | プロパン及びイソブタンのアンモ酸化又は酸化方法 |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP2205554A2 (pt) |
| JP (1) | JP5450426B2 (pt) |
| KR (1) | KR20100090252A (pt) |
| CN (1) | CN101878194A (pt) |
| BR (1) | BRPI0817877A2 (pt) |
| EG (1) | EG26218A (pt) |
| MX (1) | MX2010003907A (pt) |
| MY (1) | MY154935A (pt) |
| RU (1) | RU2495024C2 (pt) |
| WO (1) | WO2009048553A2 (pt) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TR201810575T4 (tr) | 2010-05-13 | 2018-08-27 | Asahi Chemical Ind | Karışık katalizör. |
| JP5694727B2 (ja) * | 2010-10-04 | 2015-04-01 | 旭化成ケミカルズ株式会社 | 不飽和酸又は不飽和ニトリルの製造方法 |
| JP5866292B2 (ja) * | 2010-11-05 | 2016-02-17 | 旭化成ケミカルズ株式会社 | 酸化物触媒、酸化物触媒の製造方法、不飽和酸の製造方法及び不飽和ニトリルの製造方法 |
| JP5879029B2 (ja) * | 2010-11-09 | 2016-03-08 | 日立造船株式会社 | アンモニア酸化・分解触媒 |
| CN103402976B (zh) | 2011-03-02 | 2016-03-30 | 旭化成化学株式会社 | 不饱和腈的制造方法 |
| DE102013202048A1 (de) * | 2013-02-07 | 2013-04-18 | Basf Se | Verfahren zur Herstellung einer katalytisch aktiven Masse, die ein Gemisch aus einem die Elemente Mo und V enthaltenden Multielementoxid und wenigstens einem Oxid des Molybdäns ist |
| CN104645984B (zh) * | 2013-11-20 | 2017-09-19 | 正大能源材料(大连)有限公司 | 一种饱和烷烃氨氧化制取不饱和腈的催化剂及其应用 |
| CN105771959B (zh) * | 2014-12-22 | 2018-12-18 | 中触媒有限公司 | 一种复合金属氧化物催化剂及其制备方法和应用 |
| CN107282060B (zh) * | 2016-04-13 | 2020-01-03 | 中国石油化工股份有限公司 | 氨氧化工艺丙烯腈催化剂 |
| CN107282061B (zh) * | 2016-04-13 | 2020-01-03 | 中国石油化工股份有限公司 | 氨氧化制丙烯腈的催化剂 |
| CN107282064B (zh) * | 2016-04-13 | 2020-05-05 | 中国石油化工股份有限公司 | 用于生产丙烯腈的催化剂 |
| CN107282062A (zh) * | 2016-04-13 | 2017-10-24 | 中国石油化工股份有限公司 | 丙烯氨氧化制丙烯腈的催化剂及其制备方法 |
| CN107282063B (zh) * | 2016-04-13 | 2020-01-03 | 中国石油化工股份有限公司 | 丙烯氨氧化法丙烯腈催化剂 |
| CN107282065B (zh) * | 2016-04-13 | 2020-01-03 | 中国石油化工股份有限公司 | 丙烯腈催化剂及其制备方法 |
| CN107282092B (zh) * | 2016-04-13 | 2020-03-31 | 中国石油化工股份有限公司 | 用于烯烃氨氧化合成丙烯腈的催化剂 |
| CN107282093A (zh) * | 2016-04-13 | 2017-10-24 | 中国石油化工股份有限公司 | 丙烯氨氧化制丙烯腈的催化剂 |
| CN106076413A (zh) * | 2016-06-05 | 2016-11-09 | 王金明 | 一种异丁烷生产甲基丙烯酸催化剂的制备方法 |
| WO2026004428A1 (ja) * | 2024-06-28 | 2026-01-02 | 旭化成株式会社 | 気相接触酸化反応触媒の製造方法、不飽和ニトリルの製造方法、及びアルケンの製造方法 |
| WO2026004414A1 (ja) * | 2024-06-28 | 2026-01-02 | 旭化成株式会社 | 触媒及びその製造方法並びに不飽和ニトリル又はアルケンの製造方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0529853B1 (en) * | 1991-08-08 | 1996-02-28 | Mitsubishi Chemical Corporation | Catalyst and process for producing nitriles |
| JP3168716B2 (ja) * | 1992-02-04 | 2001-05-21 | 三菱化学株式会社 | ニトリルの製造法 |
| JP3217794B2 (ja) * | 1996-03-12 | 2001-10-15 | 旭化成株式会社 | 不飽和ニトリルを製造する方法 |
| US5994580A (en) * | 1996-10-21 | 1999-11-30 | Toagosei Co., Ltd. | Process for producing acrylic acid |
| JP4179675B2 (ja) * | 1997-08-11 | 2008-11-12 | 旭化成ケミカルズ株式会社 | 不飽和ニトリルを製造する方法 |
| JP4484995B2 (ja) * | 2000-01-31 | 2010-06-16 | 旭化成ケミカルズ株式会社 | 不飽和ニトリルを製造する方法 |
| WO2001096016A1 (en) * | 2000-06-15 | 2001-12-20 | Asahi Kasei Kabushiki Kaisha | Catalyst for vapor-phase catalytic oxidation or vapor-phase catalytic ammoxidation of propane or isobutane |
| JP2003048870A (ja) * | 2001-05-30 | 2003-02-21 | Mitsubishi Chemicals Corp | アクリロニトリルおよび／またはアクリル酸の製造方法 |
| JP4688499B2 (ja) * | 2002-12-02 | 2011-05-25 | イネオス・ユーエスエイ・エルエルシー | オレフィンのアクリロニトリル及びメタクリロニトリルへの転化用の触媒組成物およびその転化方法 |
| DE60336348D1 (de) * | 2003-06-09 | 2011-04-21 | Asahi Kasei Chemicals Corp | Katalysator zur oxidation oder ammoxidation |
| JP2005193172A (ja) * | 2004-01-08 | 2005-07-21 | Daiyanitorikkusu Kk | 流動反応方法およびアクリロニトリルの製造方法 |
-
2008
- 2008-10-07 JP JP2010528872A patent/JP5450426B2/ja not_active Expired - Fee Related
- 2008-10-07 MX MX2010003907A patent/MX2010003907A/es not_active Application Discontinuation
- 2008-10-07 EP EP08837190A patent/EP2205554A2/en not_active Withdrawn
- 2008-10-07 WO PCT/US2008/011551 patent/WO2009048553A2/en not_active Ceased
- 2008-10-07 BR BRPI0817877-1A patent/BRPI0817877A2/pt not_active IP Right Cessation
- 2008-10-07 MY MYPI2010001637A patent/MY154935A/en unknown
- 2008-10-07 KR KR1020107010308A patent/KR20100090252A/ko not_active Abandoned
- 2008-10-07 CN CN2008801183712A patent/CN101878194A/zh active Pending
- 2008-10-07 RU RU2010118525/04A patent/RU2495024C2/ru not_active IP Right Cessation
-
2010
- 2010-04-11 EG EG2010040582A patent/EG26218A/en active
Also Published As
| Publication number | Publication date |
|---|---|
| CN101878194A (zh) | 2010-11-03 |
| BRPI0817877A2 (pt) | 2015-03-31 |
| EP2205554A2 (en) | 2010-07-14 |
| JP2011500564A (ja) | 2011-01-06 |
| MX2010003907A (es) | 2010-09-14 |
| EG26218A (en) | 2013-04-29 |
| MY154935A (en) | 2015-08-28 |
| KR20100090252A (ko) | 2010-08-13 |
| RU2495024C2 (ru) | 2013-10-10 |
| RU2010118525A (ru) | 2011-11-20 |
| WO2009048553A3 (en) | 2009-06-11 |
| WO2009048553A2 (en) | 2009-04-16 |
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