JP2020100520A - 酸化亜鉛修飾mfi型ゼオライト及びそれを用いた芳香族化合物の製造方法 - Google Patents
酸化亜鉛修飾mfi型ゼオライト及びそれを用いた芳香族化合物の製造方法 Download PDFInfo
- Publication number
- JP2020100520A JP2020100520A JP2018238109A JP2018238109A JP2020100520A JP 2020100520 A JP2020100520 A JP 2020100520A JP 2018238109 A JP2018238109 A JP 2018238109A JP 2018238109 A JP2018238109 A JP 2018238109A JP 2020100520 A JP2020100520 A JP 2020100520A
- Authority
- JP
- Japan
- Prior art keywords
- aromatic compound
- mfi
- type zeolite
- zinc
- zinc oxide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 title claims abstract description 145
- 239000010457 zeolite Substances 0.000 title claims abstract description 138
- 229910021536 Zeolite Inorganic materials 0.000 title claims abstract description 132
- 239000011701 zinc Substances 0.000 title claims abstract description 112
- 229910052725 zinc Inorganic materials 0.000 title claims abstract description 112
- 150000001491 aromatic compounds Chemical class 0.000 title claims abstract description 110
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 title claims abstract description 94
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 41
- 239000003054 catalyst Substances 0.000 claims abstract description 40
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 22
- 238000005259 measurement Methods 0.000 claims abstract description 20
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 17
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 15
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 14
- 239000002131 composite material Substances 0.000 claims description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000013256 coordination polymer Substances 0.000 claims description 20
- 229920001795 coordination polymer Polymers 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 12
- 238000010304 firing Methods 0.000 claims description 10
- 239000011787 zinc oxide Substances 0.000 claims description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 7
- 239000008096 xylene Substances 0.000 claims description 7
- 238000012986 modification Methods 0.000 claims description 3
- 230000004048 modification Effects 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 39
- 230000001747 exhibiting effect Effects 0.000 abstract description 3
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- -1 zinc oxide-modified MFI Chemical class 0.000 description 69
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 58
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
- 239000001294 propane Substances 0.000 description 29
- 239000007789 gas Substances 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000002994 raw material Substances 0.000 description 21
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 13
- 239000000843 powder Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 10
- XIOUDVJTOYVRTB-UHFFFAOYSA-N 1-(1-adamantyl)-3-aminothiourea Chemical compound C1C(C2)CC3CC2CC1(NC(=S)NN)C3 XIOUDVJTOYVRTB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000005119 centrifugation Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 239000012188 paraffin wax Substances 0.000 description 5
- 239000011148 porous material Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 4
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 4
- 150000003752 zinc compounds Chemical class 0.000 description 4
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910000323 aluminium silicate Inorganic materials 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 3
- JXTGICXCHWMCPM-UHFFFAOYSA-N (methylsulfinyl)benzene Chemical compound CS(=O)C1=CC=CC=C1 JXTGICXCHWMCPM-UHFFFAOYSA-N 0.000 description 2
- LOWMYOWHQMKBTM-UHFFFAOYSA-N 1-butylsulfinylbutane Chemical compound CCCCS(=O)CCCC LOWMYOWHQMKBTM-UHFFFAOYSA-N 0.000 description 2
- AIDFJGKWTOULTC-UHFFFAOYSA-N 1-butylsulfonylbutane Chemical compound CCCCS(=O)(=O)CCCC AIDFJGKWTOULTC-UHFFFAOYSA-N 0.000 description 2
- JEXYCADTAFPULN-UHFFFAOYSA-N 1-propylsulfonylpropane Chemical compound CCCS(=O)(=O)CCC JEXYCADTAFPULN-UHFFFAOYSA-N 0.000 description 2
- SLLDUURXGMDOCY-UHFFFAOYSA-N 2-butyl-1h-imidazole Chemical compound CCCCC1=NC=CN1 SLLDUURXGMDOCY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 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 2
- 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 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 238000009616 inductively coupled plasma Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 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 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- BHHYHSUAOQUXJK-UHFFFAOYSA-L zinc fluoride Chemical compound F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 description 2
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 102100025490 Slit homolog 1 protein Human genes 0.000 description 1
- 101710123186 Slit homolog 1 protein Proteins 0.000 description 1
- 102100027340 Slit homolog 2 protein Human genes 0.000 description 1
- 101710133576 Slit homolog 2 protein Proteins 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000004323 axial length Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 238000004993 emission spectroscopy Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000013335 mesoporous material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000012229 microporous material Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- PRCNQQRRDGMPKS-UHFFFAOYSA-N pentane-2,4-dione;zinc Chemical compound [Zn].CC(=O)CC(C)=O.CC(=O)CC(C)=O PRCNQQRRDGMPKS-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003196 poly(1,3-dioxolane) Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001028 reflection method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- DJWUNCQRNNEAKC-UHFFFAOYSA-L zinc acetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- RKQOSDAEEGPRER-UHFFFAOYSA-L zinc diethyldithiocarbamate Chemical compound [Zn+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S RKQOSDAEEGPRER-UHFFFAOYSA-L 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- CITILBVTAYEWKR-UHFFFAOYSA-L zinc trifluoromethanesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F CITILBVTAYEWKR-UHFFFAOYSA-L 0.000 description 1
- SQOXTAJBVHQIOO-UHFFFAOYSA-L zinc;dicarbamothioate Chemical class [Zn+2].NC([O-])=S.NC([O-])=S SQOXTAJBVHQIOO-UHFFFAOYSA-L 0.000 description 1
- RXBXBWBHKPGHIB-UHFFFAOYSA-L zinc;diperchlorate Chemical compound [Zn+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O RXBXBWBHKPGHIB-UHFFFAOYSA-L 0.000 description 1
- JXNCWJJAQLTWKR-UHFFFAOYSA-N zinc;methanolate Chemical compound [Zn+2].[O-]C.[O-]C JXNCWJJAQLTWKR-UHFFFAOYSA-N 0.000 description 1
- WEHCCWCYFYMBQX-UHFFFAOYSA-L zinc;n,n,n',n'-tetramethylethane-1,2-diamine;dichloride Chemical compound Cl[Zn]Cl.CN(C)CCN(C)C WEHCCWCYFYMBQX-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B25—HAND TOOLS; PORTABLE POWER-DRIVEN TOOLS; MANIPULATORS
- B25J—MANIPULATORS; CHAMBERS PROVIDED WITH MANIPULATION DEVICES
- B25J9/00—Programme-controlled manipulators
- B25J9/16—Programme controls
- B25J9/1694—Programme controls characterised by use of sensors other than normal servo-feedback from position, speed or acceleration sensors, perception control, multi-sensor controlled systems, sensor fusion
- B25J9/1697—Vision controlled systems
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B25—HAND TOOLS; PORTABLE POWER-DRIVEN TOOLS; MANIPULATORS
- B25J—MANIPULATORS; CHAMBERS PROVIDED WITH MANIPULATION DEVICES
- B25J9/00—Programme-controlled manipulators
- B25J9/16—Programme controls
- B25J9/1656—Programme controls characterised by programming, planning systems for manipulators
- B25J9/1664—Programme controls characterised by programming, planning systems for manipulators characterised by motion, path, trajectory planning
- B25J9/1666—Avoiding collision or forbidden zones
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B25—HAND TOOLS; PORTABLE POWER-DRIVEN TOOLS; MANIPULATORS
- B25J—MANIPULATORS; CHAMBERS PROVIDED WITH MANIPULATION DEVICES
- B25J9/00—Programme-controlled manipulators
- B25J9/16—Programme controls
- B25J9/1656—Programme controls characterised by programming, planning systems for manipulators
- B25J9/1661—Programme controls characterised by programming, planning systems for manipulators characterised by task planning, object-oriented languages
-
- 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
- Engineering & Computer Science (AREA)
- Robotics (AREA)
- Mechanical Engineering (AREA)
- Silicates, Zeolites, And Molecular Sieves (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Manipulator (AREA)
Abstract
Description
さらには、少なくとも下記(A)工程及び(B)工程を含む酸化亜鉛修飾MFI型ゼオライトの製造方法に関するものでもある。
(A)工程;MFIゼオライトと、一般式(1)で示される単位組成の配位高分子とを含む亜鉛複合MFI型ゼオライトを製造する工程。
(B)工程;(A)工程により得られた亜鉛複合MFI型ゼオライトを焼成し、酸化亜鉛修飾MFI型ゼオライトを製造する工程。
(A)工程;MFIゼオライトと、上記一般式(1)の単位組成で示される配位高分子とを含む、亜鉛複合MFI型ゼオライトを製造する工程。
(B)工程;(A)工程により得られた亜鉛複合MFI型ゼオライトを焼成し、酸化亜鉛修飾MFI型ゼオライトを製造する工程。
そして、その際の亜鉛化合物としては、亜鉛を含み水溶性のものであれば制限はなく、例えば塩化亜鉛(II)、フッ化亜鉛(II)、臭化亜鉛(II)、ヨウ化亜鉛(II)等のハロゲン化亜鉛(II)、酢酸亜鉛(II)、硝酸亜鉛(II)、硫酸亜鉛(II)、炭酸亜鉛(II)、リン酸亜鉛(II)、過塩素酸亜鉛(II)、ステアリン酸亜鉛(II)、テトラフルオロホウ酸亜鉛(II)、ホウ酸亜鉛(II)、トリフルオロメタンスルホン酸亜鉛(II)等の無機/有機オキソ酸亜鉛(II)、ジメチルジチオカルバミン酸亜鉛(II)、ジエチルジチオカルバミン酸亜鉛(II)等のチオカルバミン酸亜鉛(II)塩、塩化(N,N,N’,N’−テトラメチルエチレンジアミン)亜鉛(II)、亜鉛(II)アセチルアセトナート等の亜鉛(II)キレート錯体、亜鉛(II)メトキシド等の亜鉛(II)アルコキシド化合物、ビス[ビス(トリメチルシリル)アミド]亜鉛などの亜鉛(II)アミド等を挙げることができ、特に亜鉛複合MFI型ゼオライトの収率に優れることから、硝酸亜鉛(II)、硫酸亜鉛(II)等の無機/有機オキソ酸亜鉛(II)であることが好ましく、硝酸亜鉛(II)がより好ましい。
実施例により得られた酸化亜鉛修飾MFI型ゼオライト、それを含む芳香族化合物製造用触媒は、以下の方法により調製し、芳香族化合物の製造評価を行った。
触媒温度:520℃。
流通ガス:原料炭化水素50mol%+窒素50mol%の混合ガス、60mL/分。
触媒体積に対する原料炭化水素の体積の比:1000/時間。
触媒重量:0.9g。
触媒形状:酸化亜鉛修飾MFI型ゼオライト粉末を油圧プレスで400kgf/cm2で1分間圧縮成型した後に粉砕し、約1mmのペレット形状とした。
製造圧力:0.1MPa。
粉末X線回折パターンの測定は、リガク社製Smart Lab装置(X線管球:CuKα、管電流:30mA、管電圧:40kV、単色化法:Kβフィルター法)を用いて、入射平衡スリットの開口角:5°、入射長手制限スリットの長さ:10mm、受光平衡スリットの開口角:5°、入射スリット:1/2°、受光スリット1:20mm、受光スリット2:20mmとして、回折角(2θ)=5〜50°の範囲を走査速度2°/分で走査し、対称反射法で測定した。ピーク高さは、統合粉末X線解析ソフトウェアPDXLを用いて、バックグラウンド除去及びKα2除去した回折パターンより求めた。
テトラプロピルアンモニウム(以降、TPAと略記する。)水酸化物と水酸化ナトリウムの水溶液に不定形アルミノシリケートゲルを添加して懸濁させた。得られた懸濁液にMFI型ゼオライトを種晶として加え原料組成物とした。その際の種晶の添加量は、原料組成物中のAl2O3とSiO2の重量の和に対して、0.7重量%とした。また、副生したエタノールは濃縮して除いた。
SiO2/Al2O3モル比=44、TPA/Siモル比=0.05、Na/Siモル比=0.16、OH/Siモル比=0.21、H2O/Siモル比=10
得られた原料組成物をステンレス製オートクレーブに密閉し、115℃で撹拌しながら4日間結晶化させ、スラリー状混合液を得た。結晶化後のスラリー状混合液を遠心沈降機で固液分離した後、十分量の純水で固体粒子を洗浄し、110℃で乾燥して乾燥粉末を得た。得られた粉末を、粉末X線回折を測定したところ、典型的なMFI型ゼオライトの粉末X線回折パターンを示した。
参考例1で得られたMFI型ゼオライト2.65gに、硝酸亜鉛六水和物0.30gと水0.81gからなる水溶液を加えて混練し、110℃で12時間乾燥した後、540℃で2時間焼成することで酸化亜鉛修飾MFI型ゼオライト(C−1)を調製した。
参考例1で得られたMFI型ゼオライト2.51gに、硝酸亜鉛六水和物0.21gと水0.79gからなる水溶液を加えて混練し、110℃で12時間乾燥した後、540℃で2時間焼成することで酸化亜鉛修飾MFI型ゼオライト(C−2)を調製した。
参考例1で得られたMFI型ゼオライト2.90gに、硝酸亜鉛六水和物0.16gと水0.97gからなる水溶液を加えて混練し、110℃で12時間乾燥した後、540℃で2時間焼成することで酸化亜鉛修飾MFI型ゼオライト(C−3)を調製した。
参考例1で得られたMFI型ゼオライト2.51gに、硝酸亜鉛六水和物230mg(0.773mmol)、2−メチルイミダゾール630mg(7.67mmol)、DMF(28.5mL)を加え、超音波を10分間照射した後、140℃にて24時間加熱した。反応混合物を室温に放冷後、固体を遠心分離にて集め、DMF(30mLx3)、メタノール(30mLx3)で洗浄し、真空乾燥することで、薄黄色粉末の亜鉛複合MFI型ゼオライト1(3.29g)を得た。その際の配位高分子は、Rがメチル基のものであった。
参考例1で得られたMFI型ゼオライト2.51gに、硝酸亜鉛六水和物230mg(0.773mmol)、2−メチルイミダゾール630mg(7.67mmol)、DMF28.5mLを加え、超音波を10分間照射した後、140℃にて24時間加熱撹拌した。反応混合物を室温に放冷後、固体を遠心分離にて集め、DMF(30mLx3)、メタノール(30mLx3)で洗浄し、真空乾燥することで、薄黄色粉末の亜鉛複合MFI型ゼオライト2(3.44g)を得た。その際の配位高分子は、Rがメチル基のものであった。
参考例1で得られたMFI型ゼオライト1.26gに、硝酸亜鉛六水和物229mg(0.770mmol)、2−メチルイミダゾール628mg(7.65mmol)、DMF28.5mLを加え、超音波を10分間照射した後、140℃にて24時間加熱撹拌した。反応混合物を室温に放冷後、固体を遠心分離にて集め、DMF(30mLx3)、メタノール(30mLx3)で洗浄し、真空乾燥した。同じ操作を2回繰り返すことで、薄黄色粉末の亜鉛複合MFI型ゼオライト3(3.20g)を得た。その際の配位高分子は、Rがメチル基のものであった。
参考例1で得られたMFI型ゼオライト2.50gに、硝酸亜鉛六水和物228mg(0.766mmol)、2−ブチルイミダゾール951mg(7.66mmol)、DMF28.5mLを加え、超音波を10分間照射した後、140℃にて24時間加熱撹拌した。反応混合物を室温に放冷後、固体を遠心分離にて集め、DMF(30mLx3)、メタノール(30mLx3)で洗浄し、真空乾燥することで、白色粉末の亜鉛複合MFI型ゼオライト4(3.15g)を得た。その際の配位高分子は、Rがブチル基のものであった。
参考例1で得られたMFI型ゼオライト2.50gに、硝酸亜鉛六水和物228mg(0.766mmol)、2−フェニルイミダゾール1.11g(7.69mmol)、DMF28.5mLを加え、超音波を10分間照射した後、140℃にて24時間加熱撹拌した。反応混合物を室温に放冷後、固体を遠心分離にて集め、DMF(30mLx3)、メタノール(30mLx3)で洗浄し、真空乾燥することで、黄白色粉末の亜鉛複合MFI型ゼオライト5(3.16g)を得た。その際の配位高分子は、Rがフェニル基のものであった。
硝酸亜鉛六水和物228mg(0.766mmol)、2−フェニルイミダゾール1.11g(7.67mmol)、DMF28.5mLを加え、超音波を10分間照射した後、140℃にて24時間加熱撹拌した。反応混合物を室温に放冷後、固体を遠心分離にて集め、DMF(30mLx3)、メタノール(30mLx3)で洗浄し、真空乾燥することで、配位高分子190mgを得た。その際の配位高分子は、Rがフェニル基のものであった。
Claims (6)
- 粉末X線回折測定にて観測した際の回折パターンにおける(1 0 1)面反射に該当するピークの高さa、(0 5 1)面反射に該当するピークの高さb及び(0 3 3)面反射に該当するピークの高さcが、2×c/b≧[5×a/b]−3の関係式を満足し、亜鉛含有量が0.5から4wt%である酸化亜鉛修飾MFI型ゼオライト。
- 下記(A)工程及び(B)工程を含むことを特徴とする、請求項1に記載の酸化亜鉛修飾MFI型ゼオライトの製造方法。
(A)工程;MFI型ゼオライトと、一般式(1)で示される単位組成の配位高分子とを含む亜鉛複合MFI型ゼオライトを製造する工程。
(B)工程;(A)工程により得られた亜鉛複合MFI型ゼオライトを焼成し、酸化亜鉛修飾MFI型ゼオライトを製造する工程。 - 前記一般式(1)におけるRが、炭素数1から4のアルキル基又はフェニル基であることを特徴とする、請求項2に記載の酸化亜鉛修飾MFI型ゼオライトの製造方法。
- 請求項1に記載の酸化亜鉛修飾MFI型ゼオライトに低級炭化水素を接触し、芳香族化合物とすることを特徴とする芳香族化合物の製造方法。
- 芳香族化合物が、ベンゼン、トルエン及びキシレンからなる群から選ばれる少なくとも1つであることを特徴とする請求項4に記載の芳香族化合物の製造方法。
- 請求項1に記載の酸化亜鉛修飾MFI型ゼオライトを含むことを特徴とする芳香族化合物製造用触媒。
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2018238109A JP7181785B2 (ja) | 2018-12-20 | 2018-12-20 | 酸化亜鉛修飾mfi型ゼオライト及びそれを用いた芳香族化合物の製造方法 |
JP2022183046A JP7394950B2 (ja) | 2018-12-20 | 2022-11-16 | 酸化亜鉛修飾mfi型ゼオライト及びそれを用いた芳香族化合物の製造方法 |
US18/385,493 US20240157558A1 (en) | 2018-12-20 | 2023-10-31 | Robot control system, robot control method, and non-transitory computer readable medium |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2018238109A JP7181785B2 (ja) | 2018-12-20 | 2018-12-20 | 酸化亜鉛修飾mfi型ゼオライト及びそれを用いた芳香族化合物の製造方法 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2022183046A Division JP7394950B2 (ja) | 2018-12-20 | 2022-11-16 | 酸化亜鉛修飾mfi型ゼオライト及びそれを用いた芳香族化合物の製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2020100520A true JP2020100520A (ja) | 2020-07-02 |
JP7181785B2 JP7181785B2 (ja) | 2022-12-01 |
Family
ID=71140987
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018238109A Active JP7181785B2 (ja) | 2018-12-20 | 2018-12-20 | 酸化亜鉛修飾mfi型ゼオライト及びそれを用いた芳香族化合物の製造方法 |
JP2022183046A Active JP7394950B2 (ja) | 2018-12-20 | 2022-11-16 | 酸化亜鉛修飾mfi型ゼオライト及びそれを用いた芳香族化合物の製造方法 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2022183046A Active JP7394950B2 (ja) | 2018-12-20 | 2022-11-16 | 酸化亜鉛修飾mfi型ゼオライト及びそれを用いた芳香族化合物の製造方法 |
Country Status (2)
Country | Link |
---|---|
US (1) | US20240157558A1 (ja) |
JP (2) | JP7181785B2 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115558460A (zh) * | 2021-12-30 | 2023-01-03 | 上海都昱新材料科技有限公司 | 一种光伏组件用灌封胶及其制备方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006347862A (ja) * | 2004-09-21 | 2006-12-28 | Tosoh Corp | アルミノシリケートを含む新規な構造体、その製造方法およびその用途 |
JP2013198844A (ja) * | 2012-03-23 | 2013-10-03 | Shoei Chem Ind Co | 多孔性金属錯体と無機触媒材料との複合触媒の製造方法 |
WO2016121377A1 (ja) * | 2015-01-27 | 2016-08-04 | 日本ゼオン株式会社 | 分離膜およびその製造方法 |
JP2018104217A (ja) * | 2016-12-26 | 2018-07-05 | 東ソー株式会社 | 金属含有mfi型ゼオライト及びそれよりなる芳香族化合物製造用触媒 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006305408A (ja) * | 2005-04-26 | 2006-11-09 | Tosoh Corp | 芳香族化反応触媒とその触媒を用いた芳香族炭化水素の製造方法 |
-
2018
- 2018-12-20 JP JP2018238109A patent/JP7181785B2/ja active Active
-
2022
- 2022-11-16 JP JP2022183046A patent/JP7394950B2/ja active Active
-
2023
- 2023-10-31 US US18/385,493 patent/US20240157558A1/en active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006347862A (ja) * | 2004-09-21 | 2006-12-28 | Tosoh Corp | アルミノシリケートを含む新規な構造体、その製造方法およびその用途 |
JP2013198844A (ja) * | 2012-03-23 | 2013-10-03 | Shoei Chem Ind Co | 多孔性金属錯体と無機触媒材料との複合触媒の製造方法 |
WO2016121377A1 (ja) * | 2015-01-27 | 2016-08-04 | 日本ゼオン株式会社 | 分離膜およびその製造方法 |
JP2018104217A (ja) * | 2016-12-26 | 2018-07-05 | 東ソー株式会社 | 金属含有mfi型ゼオライト及びそれよりなる芳香族化合物製造用触媒 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115558460A (zh) * | 2021-12-30 | 2023-01-03 | 上海都昱新材料科技有限公司 | 一种光伏组件用灌封胶及其制备方法 |
CN115558460B (zh) * | 2021-12-30 | 2023-11-28 | 上海都昱新材料科技有限公司 | 一种光伏组件用灌封胶及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
US20240157558A1 (en) | 2024-05-16 |
JP2023014129A (ja) | 2023-01-26 |
JP7181785B2 (ja) | 2022-12-01 |
JP7394950B2 (ja) | 2023-12-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Tago et al. | Selective synthesis for light olefins from acetone over ZSM-5 zeolites with nano-and macro-crystal sizes | |
JP5545114B2 (ja) | 触媒の再生方法 | |
KR101643008B1 (ko) | 파라 치환 방향족 탄화수소의 제조 방법 | |
US9643899B2 (en) | SSZ-13 as a catalyst for conversion of chloromethane to olefins | |
AU2001283021A1 (en) | Catalyst and process for aromatic hydrocarbons production from methane | |
WO2011031017A2 (ko) | 올레핀 크레킹 반응용 제올라이트계 성형촉매 및 합성가스로부터 경질 올레핀의 제조방법 | |
US10155665B2 (en) | Zeolite synthesis with dominant and secondary templates | |
KR20110047178A (ko) | 티엔유-9 제올라이트를 이용한 탄화수소 전환반응 | |
CN109641194B (zh) | 包含小的10-环沸石微晶的催化剂和通过使含氧化合物经由所述催化剂反应来制备烃的方法 | |
WO2014003909A1 (en) | Metallophosphate molecular sieves, method of preparation and use | |
CN110234619B (zh) | 用于提升用于费歇尔-托普希反应的混合催化剂活性的方法 | |
KR101985861B1 (ko) | 메탄 및 프로판 공동 반응물의 직접 탈수소방향족화 반응을 위한 중형기공성 hzsm-11에 담지된 금속 산화물 촉매의 제조 방법 및 상기 촉매를 이용한 btx 제조 방법 | |
WO2018119195A1 (en) | Process to convert synthesis gas to olefins using a bifunctional chromium / zinc oxide-sapo-34 catalyst | |
JP7394950B2 (ja) | 酸化亜鉛修飾mfi型ゼオライト及びそれを用いた芳香族化合物の製造方法 | |
JP2011079815A (ja) | p−キシレンの製造方法 | |
JP5685870B2 (ja) | プロピレンの製造方法 | |
JP2018104217A (ja) | 金属含有mfi型ゼオライト及びそれよりなる芳香族化合物製造用触媒 | |
JP6780369B2 (ja) | 芳香族化合物製造触媒及び芳香族化合物の製造方法 | |
WO2018182948A1 (en) | Methane conversion | |
US8889939B2 (en) | Dehydrocyclodimerization using UZM-44 aluminosilicate zeolite | |
US8921634B2 (en) | Conversion of methane to aromatic compounds using UZM-44 aluminosilicate zeolite | |
WO2016140869A1 (en) | Process for oxygenate to olefin conversion using 2-d pentasil zeolite | |
CN100494129C (zh) | 制备丙烯的方法 | |
WO2018236471A1 (en) | METHODS OF OLIGOMERIZING OLEFINS AND ZEOLITES AND STRUCTURAL ORIENTATION AGENTS THEREOF | |
KR20200066436A (ko) | 니켈계 올리고머화 촉매 및 이를 이용하여 경질 올레핀을 올리고머화하는 방법 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20181225 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190122 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20211110 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20220824 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20220830 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20220927 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20221025 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20221118 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7181785 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |