WO2002055465A1 - Methode et appareil de reaction chimique faisant appel a un catalyseur a membrane - Google Patents
Methode et appareil de reaction chimique faisant appel a un catalyseur a membrane Download PDFInfo
- Publication number
- WO2002055465A1 WO2002055465A1 PCT/JP2001/011542 JP0111542W WO02055465A1 WO 2002055465 A1 WO2002055465 A1 WO 2002055465A1 JP 0111542 W JP0111542 W JP 0111542W WO 02055465 A1 WO02055465 A1 WO 02055465A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- reaction
- activated
- substance
- compound
- group
- Prior art date
Links
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 220
- 239000003054 catalyst Substances 0.000 title claims abstract description 88
- 238000000034 method Methods 0.000 title claims abstract description 81
- 239000000126 substance Substances 0.000 claims abstract description 100
- 239000001301 oxygen Substances 0.000 claims abstract description 87
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 87
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 85
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- 238000004519 manufacturing process Methods 0.000 claims abstract description 41
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 22
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 7
- 150000002576 ketones Chemical class 0.000 claims abstract description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 107
- 239000012528 membrane Substances 0.000 claims description 55
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 40
- 229910052751 metal Inorganic materials 0.000 claims description 36
- 239000002184 metal Substances 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- -1 aromatic alcohols Chemical class 0.000 claims description 30
- 229910044991 metal oxide Inorganic materials 0.000 claims description 30
- 150000004706 metal oxides Chemical class 0.000 claims description 30
- 229930195733 hydrocarbon Natural products 0.000 claims description 29
- 150000002430 hydrocarbons Chemical group 0.000 claims description 29
- 239000007789 gas Substances 0.000 claims description 24
- 239000000956 alloy Substances 0.000 claims description 22
- 229910045601 alloy Inorganic materials 0.000 claims description 22
- 230000003213 activating effect Effects 0.000 claims description 20
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 20
- 229910052763 palladium Inorganic materials 0.000 claims description 20
- 239000004215 Carbon black (E152) Substances 0.000 claims description 15
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 14
- 229910052720 vanadium Inorganic materials 0.000 claims description 14
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 14
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 13
- 150000002602 lanthanoids Chemical class 0.000 claims description 13
- 229910000510 noble metal Inorganic materials 0.000 claims description 12
- 229910052715 tantalum Inorganic materials 0.000 claims description 12
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 12
- 229910052723 transition metal Inorganic materials 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229910052758 niobium Inorganic materials 0.000 claims description 11
- 239000010955 niobium Substances 0.000 claims description 11
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 11
- 229910000314 transition metal oxide Inorganic materials 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 10
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 229910052709 silver Inorganic materials 0.000 claims description 9
- 239000004332 silver Substances 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- 229910052684 Cerium Inorganic materials 0.000 claims description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052797 bismuth Inorganic materials 0.000 claims description 4
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 4
- 150000001717 carbocyclic compounds Chemical class 0.000 claims description 4
- 239000002131 composite material Substances 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 4
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 229910052750 molybdenum Inorganic materials 0.000 claims description 4
- 239000011733 molybdenum Substances 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- 229910052772 Samarium Inorganic materials 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 229910021536 Zeolite Inorganic materials 0.000 claims description 3
- 230000004913 activation Effects 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- 239000011651 chromium Substances 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 3
- 229910001882 dioxygen Inorganic materials 0.000 claims description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052737 gold Inorganic materials 0.000 claims description 3
- 239000010931 gold Substances 0.000 claims description 3
- 229910052746 lanthanum Inorganic materials 0.000 claims description 3
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 3
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052721 tungsten Inorganic materials 0.000 claims description 3
- 239000010937 tungsten Substances 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims description 3
- 239000010457 zeolite Substances 0.000 claims description 3
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000001601 aromatic carbocyclic compounds Chemical class 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 2
- 238000005755 formation reaction Methods 0.000 claims 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 229910052726 zirconium Inorganic materials 0.000 claims 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract description 8
- 238000010960 commercial process Methods 0.000 abstract 1
- 150000002118 epoxides Chemical class 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 39
- 238000007254 oxidation reaction Methods 0.000 description 32
- 239000000047 product Substances 0.000 description 32
- 239000002994 raw material Substances 0.000 description 24
- 230000003647 oxidation Effects 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 230000003197 catalytic effect Effects 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 239000012190 activator Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 239000011148 porous material Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 230000000737 periodic effect Effects 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 238000006356 dehydrogenation reaction Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000005229 chemical vapour deposition Methods 0.000 description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000004880 explosion Methods 0.000 description 3
- 239000001307 helium Substances 0.000 description 3
- 229910052734 helium Inorganic materials 0.000 description 3
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 229910052768 actinide Inorganic materials 0.000 description 2
- 150000001255 actinides Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007809 chemical reaction catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 2
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000001027 hydrothermal synthesis Methods 0.000 description 2
- 239000010416 ion conductor Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- HBVFXTAPOLSOPB-UHFFFAOYSA-N nickel vanadium Chemical compound [V].[Ni] HBVFXTAPOLSOPB-UHFFFAOYSA-N 0.000 description 2
- 239000001272 nitrous oxide Substances 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 239000012466 permeate Substances 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 2
- 238000013341 scale-up Methods 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-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
- SRJCJJKWVSSELL-UHFFFAOYSA-N 2-methylnaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(C)=CC=C21 SRJCJJKWVSSELL-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000010097 foam moulding Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- VRWLBMGRSLQKSU-UHFFFAOYSA-N methanol;pyridine Chemical compound OC.C1=CC=NC=C1 VRWLBMGRSLQKSU-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- SWELZOZIOHGSPA-UHFFFAOYSA-N palladium silver Chemical compound [Pd].[Ag] SWELZOZIOHGSPA-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
-
- 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
- B01J10/00—Chemical processes in general for reacting liquid with gaseous media other than in the presence of solid particles, or apparatus specially adapted therefor
- B01J10/007—Chemical processes in general for reacting liquid with gaseous media other than in the presence of solid particles, or apparatus specially adapted therefor in the presence of catalytically active bodies, e.g. porous plates
-
- 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
- B01J12/00—Chemical processes in general for reacting gaseous media with gaseous media; Apparatus specially adapted therefor
- B01J12/007—Chemical processes in general for reacting gaseous media with gaseous media; Apparatus specially adapted therefor in the presence of catalytically active bodies, e.g. porous plates
-
- 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
- B01J14/00—Chemical processes in general for reacting liquids with liquids; Apparatus specially adapted therefor
- B01J14/005—Chemical processes in general for reacting liquids with liquids; Apparatus specially adapted therefor in the presence of catalytically active bodies, e.g. porous plates
-
- 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
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2475—Membrane reactors
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- B01J35/59—
-
- 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
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/008—Details of the reactor or of the particulate material; Processes to increase or to retard the rate of reaction
- B01J8/009—Membranes, e.g. feeding or removing reactants or products to or from the catalyst bed through a membrane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/58—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of molecular oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of other oxidants than molecular oxygen or their mixtures with molecular oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/36—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in compounds containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/40—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with ozone; by ozonolysis
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00054—Controlling or regulating the heat exchange system
- B01J2219/00056—Controlling or regulating the heat exchange system involving measured parameters
- B01J2219/00058—Temperature measurement
- B01J2219/00063—Temperature measurement of the reactants
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
- B01J2219/00094—Jackets
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
- B01J2219/00099—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor the reactor being immersed in the heat exchange medium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- 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
Definitions
- the present invention relates to a reaction method using a substance activated by the action of a catalyst, a method for producing aromatic alcohols using the method, and a reaction apparatus for these methods.
- Oxygen oxidation which oxidizes hydrocarbons with oxygen or air in the presence of an oxidation catalyst, is very important in the organic chemical industry.
- oxygen-containing organic compound obtained by such a reaction include ketones such as acetate, cyclohexanone, and cyclopentanone; and carboxyls such as terephthalic acid, phthalic anhydride, and maleic anhydride. Acids; examples include alkylene oxides such as ethylene oxide.
- oxygenated organic compounds include aromatic alcohols, many of which are important as basic chemicals in the organic chemical industry, of which phenol and cresol are particularly important. It is a chemical. These are used, for example, for the polycondensation reaction with formaldehyde to produce so-called phenol resin-cresol resin. These resins are widely used as paints, lacquers, or resin materials for compression molding or foam molding.
- phenol is used as a raw material for bisphenol A and bisphenol F, which are important as raw materials for epoxy resins.
- cyclohexanol obtained by hydrogenating phenol is used for ⁇ -caprolactam, a raw material for nylon. Used for manufacturing.
- the most ideal method for industrial production of phenol by the above oxidation method is the direct oxidation method, in which benzene is directly and partially oxidized.
- the direct oxidation method has difficulty in controlling the reaction and further oxidizes the phenol generated by the oxidation of benzene, so a practical production method has not yet been established.
- the cumene method is a method in which propylene and benzene are reacted to produce cumene, which is then oxidized in air with, for example, a cobalt salt catalyst to give a cumene hydroperoxide, which is then decomposed into an acid catalyst to phenol and acetone.
- This method has a high selectivity and is a very good method.However, since acetone is produced in equimolar proportion to phenol production, the price of phenol fluctuates depending on the demand of acetone. There are drawbacks.
- the indirect oxidation method generally has many reaction steps, is complicated, and has the disadvantage of generating unnecessary by-products. Therefore, development of a direct oxidation method for directly reacting oxygen with hydrocarbons has been desired.
- the production of oxygen-containing organic compounds by the direct oxidation method involves mixing raw material hydrocarbons with oxygen-containing gas and flowing the mixture through a fixed-bed flow reactor to a reactor filled with a solid catalyst. Is common. However, this method has a problem that the reaction yield is very low.
- the generated oxygen-containing compound has a lower ionization potential of the molecule, and thus is more susceptible to oxidation than the starting hydrocarbon, and the product over-reacts one after another, that is, undergoes a sequential oxidation reaction.
- the selectivity of the target product is reduced.
- Another reason is that in order to suppress this overreaction, the reaction must be carried out under dilute concentration conditions where the raw material is always in a large excess compared to the product.
- this type of reaction is basically a mixture of combustibles and oxygen (combustion) that causes combustion. Therefore, there is a danger of explosion, and in order to avoid this, it must be operated at low concentration and low reaction rate. All of the above cause low yields.
- Japanese Unexamined Patent Publication (Kokai) No. 11-518017 discloses a gas-phase oxidation reaction of propylene to propylene oxide by a silver catalyst supported on a solid support, but is specifically disclosed.
- the raw material propylene concentration in the mixed gas introduced into the reactor was as low as 10% or less, and the propylene conversion was as low as 3 to 5%. A reaction is taking place.
- membrane reactor for a certain kind of gas-phase oxidation reaction using hydrocarbons as a raw material, a method using a membrane reactor, a so-called membrane reactor (membrane reactor), has been reported.
- a membrane reactor can be used for producing C 2 hydrocarbons by an oxidative pulling reaction of methane.
- the diaphragm type catalyst used here is a composite oxide having high oxygen ion mobility and mixed conductivity, that is, an ion conductor, in which oxygen taken in from one of the diaphragms is oxygen ion O. 2 ⁇ flows to the other side and participates in the reaction.
- oxygen ion O. 2 ⁇ flows to the other side and participates in the reaction.
- Japanese Patent Application Laid-Open No. 5-194281 discloses a method in which a hydrogen permeable membrane is used in combination with a dehydrogenation catalyst in a catalytic dehydrogenation reaction of saturated hydrocarbons. This method converts the hydrogen generated by the dehydrogenation reaction into a membrane. This allows the chemical equilibrium in the system to shift to the dehydrogenation reaction side by passing through the reaction system, thereby achieving a conversion rate that exceeds the equilibrium conversion rate.
- the product is a hydrocarbon compound and not an oxygen-containing organic compound. That is, a method for producing an oxygen-containing organic compound using a membrane reactor has not been proposed so far.
- an object of the present invention is to provide a method for reacting a substance activated by the action of a catalyst such as oxygen or hydrogen with a substance which reacts with the substance such as hydrocarbons, for example.
- An object of the present invention is to provide a method for obtaining a target product safely and in a high yield while avoiding the problem. Disclosure of the invention
- the present invention provides a method of reacting a substance activated by the action of a catalyst with a substance that reacts with the activated substance, wherein the activation of the substance to be activated is performed by passing the activated substance through a membrane catalyst. This is a reaction method characterized in that the reaction is performed in a single step.
- the present invention provides a method in which a substance to be reactivated by the above-mentioned diaphragm type catalyst is provided in one of the adjacent chambers of the plurality of chambers in the reaction vessel divided into a plurality of sections by the diaphragm type catalyst for activating the passing substance. And the compound to be reacted with the activated substance is passed through the other chamber adjacent to the divided chamber, and the substance to be activated passes through the membrane catalyst. In the above reaction method, the compound is activated and reacted with the compound to be reacted.
- the present invention provides a method for producing aromatic alcohols in a single reaction step in which oxygen and hydrogen are reacted with aromatic hydrocarbons, wherein hydrogen activated by a diaphragm type catalyst for activating a substance passing therethrough is provided.
- a method for producing aromatic alcohols characterized by reacting aromatic hydrocarbons and oxygen.
- a diaphragm type catalyst for dividing the vessel into a plurality of sections is provided in the reaction vessel, and hydrogen is contained in one of the chambers adjacent to the plurality of compartments formed in the reaction vessel.
- Aromatic hydrocarbons and oxygen are allowed to flow in the other chamber adjacent to the divided chamber, and hydrogen activated when passing through the membrane catalyst is
- a diaphragm catalyst for activating a substance passing therethrough is provided in the reaction vessel so as to divide the vessel into a plurality of sections, and a plurality of partitioned chambers in the reaction vessel are adjacent to each other.
- a gas of a substance to be reactivated by the above-mentioned diaphragm type catalyst can flow, and in the other chamber adjacent to the divided chamber, the above-mentioned activated substance
- the reaction is characterized in that the compound to be activated is allowed to flow and the substance to be activated is activated when passing through the membrane catalyst, and reacts with the compound to be reacted.
- Device BRIEF DESCRIPTION OF THE FIGURES
- FIG. 1 is a drawing schematically showing a cross section of an embodiment of the diaphragm type catalytic reactor of the present invention.
- FIG. 2 is a drawing schematically showing a cross section of another embodiment of the diaphragm type catalytic reactor of the present invention.
- FIG. 3 is a drawing schematically showing a cross section of another embodiment of the diaphragm type catalytic reactor of the present invention.
- FIG. 4 is a perspective view of another embodiment of the membrane-type catalytic reactor of the present invention.
- FIG. 5 is a cross-sectional view schematically showing still another embodiment of the membrane-type catalytic reactor of the present invention. It is a drawing.
- diaphragm-type catalyst j refers to a catalyst in the form of a film capable of partitioning a reaction zone of a reaction vessel into two or more. Are divided into two, for example, and one of the substances involved in the reaction is activated when passing through the membrane-type catalyst, and this is reacted with the compound to be reacted, which is present on the other side of the membrane-type catalyst.
- the use of a plurality of membrane-type catalysts can make the reaction more efficient and can respond to scale-up.
- the substance to be activated (hereinafter referred to as “activating substance”) is oxygen, and the compound to be reacted with the activated substance (
- the reaction hereinafter referred to as “reaction compound”) is a hydrocarbon, and the resulting compound (hereinafter, referred to as “product”) is an oxygen-containing organic compound (hereinafter, referred to as “first embodiment reaction”).
- first embodiment reaction A reaction in which the substance is hydrogen, the reaction compounds are hydrocarbons and oxygen, and the product is an oxygen-containing organic compound (hereinafter, referred to as “second embodiment reaction”).
- a specific example of the first embodiment reaction is an oxidation reaction in which a raw material hydrocarbon is oxidized with activated oxygen to produce an oxygen-containing organic compound.
- Manufacture of alkylene-based oxides from raw materials Manufacture of ketones from raw-refined hydrocarbons and cyclic hydrocarbons; Manufacture of aldehydes from raw-refined hydrocarbons; Production of carboxylic acids using hydrogen, olefin hydrocarbons, and aromatic hydrocarbons as raw materials is exemplified.
- the second mode reaction there is a reaction of producing a oxygen-containing organic compound by reacting hydrocarbons as raw materials with hydrogen activated by oxygen, for example, propylene-butene and the like. Production of aldehydes, ketones, alkylene oxides or aromatic alcohols using olefins as raw materials.
- An important component in the present invention is a membrane catalyst.
- This diaphragm catalyst has an action of activating a substance passing therethrough.
- the metal or alloy itself which is a catalyst active component, may be formed into a porous film, or the surface of a film-shaped porous support may be used.
- a catalytically active component include the following diaphragm catalysts.
- the metal of (A), the alloy of (B), the noble metal of (C), or the transition metal oxide or lanthanide-based oxide of (D) are active components of the catalyst, respectively.
- the metal film (A) for example, a metal film made of a metal selected from the group consisting of palladium, niobium, tantalum and vanadium can be mentioned. Furthermore, a metal film formed by coating palladium on a metal film composed of a metal selected from the group consisting of niobium, tantalum and vanadium can also be used.
- the alloy film of (B) may be, for example, at least one element selected from the group consisting of a first transition metal element, a second transition metal element, a third transition metal element, a lanthanide element, and an actinide element. And an alloy film composed of an element selected from the group consisting of palladium, nickel, tantalum, and vanadium. Also, an alloy composed of an alloy of at least one element selected from the group consisting of yttrium, cerium, silver, nickel and titanium and a metal selected from the group consisting of palladium, niobium, tantalum and vanadium Membrane can also be used.
- the first transition metal element is an element of Group 4A to Group 8A in the fourth period of the periodic table
- the second transition metal element is an element of Group 4A in the fifth period of the periodic table
- the group 8A element and the third transition metal element mean the group 4A to group 8A elements of the sixth period of the periodic table, respectively.
- a lanthanide element means an element of the lanthanide series of the periodic table
- an actidide element means an element of the actinide series of the periodic table.
- the metal (A) or the alloy (B) is formed into a porous film by itself. It may be shaped, or may be carried on a film such as a porous metal oxide described below.
- the noble metal supported on the porous metal oxide film (C) includes a noble metal selected from the group consisting of silver, gold, platinum and palladium.
- the transition metal oxide supported on the metal oxide porous membrane of (D) includes chromium, manganese, iron, cobalt, nickel, osmium, ruthenium, vanadium, molybdenum, tungsten, and bismuth. Transition metal oxides selected from the group consisting of cerium, lanthanum, and samarium, and the lanthanide-based oxide supported on the metal oxide porous film of (D). Oxides of the elements are mentioned.
- the porous metal oxide used in the above (C) and (D) is not particularly limited as long as it can uniformly disperse and support the active component of the catalyst and is effective as a carrier for the oxidation reaction catalyst and the like.
- a porous body of an oxide composed of a metal selected from the group consisting of silica, alumina, titania and zirconia, and a multi-layer selected from a composite of two or more of these four metal oxides A porous body, or a porous body of a zealite light can be used.
- silica, alumina, titania, zirconia, zirconite, etc. are coated by dip coating, spray coating, spin coating, hydrothermal synthesis, etc. in order to appropriately suppress and reduce gas permeability.
- What is supported on a porous ceramic film can also be used as a porous body.
- the above-described porous metal oxide is basically in the form of a film, but is not particularly limited as long as the gaseous reaction component as a raw material can permeate from one side to the other. Quality materials can be used.
- the pore size of the porous body is selected according to the type and conditions of the desired reaction, but generally a pore size of 0.5 nm to 10 m is appropriate, and a pore size of 0.5 nm to 1 mm. But good Good.
- the specific surface area of the porous body is preferably 0.5 to 1,000 m 2 ng.
- a film having a thickness of 50 m to 5 mm can be used, but a film having a thickness of 100 m to 500 m is preferable in terms of mechanical strength and transmission resistance.
- the above pore diameter and specific surface area can be controlled by the conditions at the time of production of the porous metal oxide or preparation of the catalyst, and are appropriately selected depending on the type of reaction.
- the film has a tubular shape or a plate-like shape.
- a porous body having such a shape can be obtained, for example, by using a method described in Japanese Patent Publication No. 5-63634 (Patent No. 18550556).
- the type of the catalytically active component supported on the porous metal oxide membrane is selected depending on the type of the intended reaction. For example, when an aldehyde is produced by an oxidation reaction, a metal compound containing molybdenum, bismuth or the like is used. When a carboxylic acid is produced, a metal compound containing vanadium or the like is used. What is necessary is just to carry the metal compound containing silver etc.
- a method used for preparing an ordinary oxidation reaction catalyst for example, an impregnation method, a precipitation method, an ion exchange method, a vapor deposition method, a hydrothermal synthesis method, or the like is used. Can be adopted. In addition, CVD (chemical vapor deposition), PVD (physical vapor deposition), dip coating, spray coating, spin coating, etc. can also be applied.
- the content of the catalytically active component supported on the porous metal oxide membrane is appropriately set depending on the type of aromatic hydrocarbons and reaction conditions.
- An embodiment of the method of the present invention is such that an activating substance, for example, oxygen or hydrogen involved in the reaction passes through a membrane catalyst selected from any of the above (A) to (D). Any form can be used as long as it is activated by reacting with a reactive compound, for example, a hydrocarbon or a mixture of hydrocarbon and oxygen. If necessary, nitrogen, steam, helium, carbon dioxide, methane or the like may be used as a diluent for the reaction.
- a reactive compound for example, a hydrocarbon or a mixture of hydrocarbon and oxygen.
- nitrogen, steam, helium, carbon dioxide, methane or the like may be used as a diluent for the reaction.
- a reaction vessel equipped with a diaphragm catalyst hereinafter, may be abbreviated as a diaphragm reactor
- a diaphragm reactor which is advantageously used in the practice of the method of the present invention
- FIG. 1 is a drawing schematically showing a cross section of an embodiment of the diaphragm type catalytic reactor of the present invention.
- 1 is a reaction compound accumulating section
- 2 is an activating substance flowing section
- 3 is a membrane catalyst
- 4 is a reaction compound inlet
- 5 is a reaction compound outlet
- 6 is an activating substance inlet
- 7 is an activating substance outlet
- Reference numeral 8 denotes a reaction vessel.
- the reaction apparatus shown in FIG. 1 has a structure in which a reaction vessel is divided into a reaction compound retaining section 1 and an activated substance flowing section 2 by a single planar catalyst 3.
- the activator and the reactant enter the reactor from opposite directions and flow in opposite directions.
- FIG. 1 is a reaction compound accumulating section
- 2 is an activating substance flowing section
- 3 is a membrane catalyst
- 4 is a reaction compound inlet
- 5 is a reaction compound outlet
- 6 is an activating substance inlet
- 7 is an activating substance outlet
- the reaction apparatus of this embodiment has a structure in which a plurality of reaction compound accumulating sections 1 and an activating substance flowing section 2 are stacked, and is effective when the reaction via the membrane catalyst 3 is performed in a scale-up manner or the like. .
- there are four partitioned chambers but this is not a limitation.For example, if an odd-numbered diaphragm catalyst 3 is used, the reaction vessel is partitioned into an even-numbered chamber one more than the odd-numbered chamber. can do.
- FIG. 3 is a drawing showing another embodiment of the reactor of the present invention.
- the reactor of this embodiment utilizes a cylindrical diaphragm catalyst 3, and is partially or wholly used.
- the space inside the inner tube 9 formed by the diaphragm catalyst 3 becomes the reaction compound retaining portion 1, and the space between the outer tube formed by the reaction vessel 8 and the inner tube 9 becomes the active material flowing portion 2.
- This embodiment has a structure in which the activating substance and the reaction compound flow in parallel with each other.
- FIG. 4 is a drawing showing another embodiment of the reactor of the present invention, and has a structure in which a plurality of internal cylinders 9 of FIG. 3 are provided.
- a plurality of cylindrical diaphragm catalysts 3 are used, whereby the area of the diaphragm catalyst 3 involved in the reaction can be increased.
- FIG. 5 is a longitudinal sectional view of a double-tube reactor for a liquid phase reaction.
- 10 is a gas volatilizer (bubbler 1)
- 11 is a liquid level gauge.
- an aromatic hydrocarbon as a reaction compound is introduced into the reaction compound retaining section 1 from the reaction compound inlet 4a.
- oxygen is introduced into the reaction compound retaining section 1 via the reaction compound inlet 4b and the gas volatilization device 10.
- activated hydrogen is introduced from the activated substance inlet 6 through the diaphragm catalyst 3 into the reaction compound retaining section 1.
- the activated hydrogen reacts with oxygen and aromatic hydrocarbons to generate aromatic alcohols.
- the generated aromatic alcohol is taken out from the reaction compound outlet 5.
- the reaction apparatus used in the present invention has been exemplified.However, in these, a heating device and a cooling device that are generally provided in the reaction container and cover the reaction container, and an instrument for measuring the internal temperature and pressure are omitted. ing. However, it goes without saying that these can be added.
- the reaction compound outlet 5 may be closed, and the whole amount of the supplied hydrocarbon gas may be permeated to the activating substance flowing section 2 side.
- the gas flow can be improved by filling the reactant holding part 1 or the activating substance distribution part 2 with a filler or attaching a baffle plate or the like. The state can be changed.
- reaction conditions for carrying out the oxidation reaction using the apparatus of the present invention vary depending on the type of reaction and the like, but the reaction temperature is generally in the range of ⁇ 200 to 900 ° C., preferably 0 to 600 ° C. ° C range, and the reaction pressure is 0. ⁇ 1 0 0 kg / cm 2 range, preferably in the range of 0.5 ⁇ 5 0 kg / cm 2.
- preferred raw material hydrocarbons in the case of performing the oxidation reaction in the reaction of the first embodiment of the present invention include: paraffins having 1 to 8 carbon atoms, and 2 to 1 carbon atoms. And olefins having a carbon number of 2 and aromatic compounds having 6 to 20 carbon atoms.
- reaction conditions for producing aromatic alcohols by hydrogen gas, aromatic hydrocarbons and oxygen by the reaction of the second embodiment of the method of the present invention are as follows.
- the reaction temperature is in the range of ⁇ 200 to 900 ° C., preferably in the range of 110 to 600 ° C.
- the reaction pressure is in the range of 0.1 to 150 kg / cm 2 , Preferably it is in the range of 0.5 to 50 kg / cm 2 .
- the main raw material used in the reaction of the second embodiment of the present invention is an aromatic hydrocarbon, and is selected from a carbocyclic compound or a heterocyclic compound having at least one aromatic ring.
- a carbocyclic compound having at least one aromatic ring a compound having a monocyclic, bicyclic or tricyclic aromatic ring, or a nucleus-substituted compound of each of these compounds is used.
- monocyclic aromatic carbocyclic compounds are benzene or It is a benzene nucleus-substituted compound represented by the general formula.
- Ar is a benzene ring
- X is an aromatic group selected from an alkyl group having 1 to 24 carbon atoms, an amino group, a hydroxyl group, a propyloxyl group, an ester group, a cyano group, a nitro group, a halogen atom, and oxygen.
- a group on the aromatic ring, and in the case of a plurality of groups, may be the same or different, and n represents an integer of up to 5)
- the bicyclic aromatic carbocyclic compound may be substituted by, for example, naphthalene, tetrauran, biphenyl, cyclohexylbenzene or indane, or a substituent represented by X in the above general formula (I). Nucleus-substituted compound.
- the tricyclic aromatic carbocyclic compound is, for example, anthracene, phenanthrene, fluorene or azulene, or a nuclear-substituted compound obtained by substituting these compounds with the substituent represented by X in the above general formula (I). It is.
- heterocyclic compounds having at least one aromatic ring include, for example, pyran, furan, thiocyanphen, techifenfen, pyrrole, pyridine, thiopyridine, pyridine methoxide, pyrazine, indole, quinoline, It is purine, quinazoline, bibilibin or phenanthroline, or a nuclear-substituted compound obtained by substituting these compounds with the substituent represented by X in the above general formula (I).
- the reaction gas concentration can be increased.
- a reaction equivalent to or higher than the conventional catalytic reaction can be achieved.
- the reaction can be performed at a high speed, and the gaseous materials involved in the oxidation reaction can be easily controlled so that only the necessary degree of contact for the desired reaction occurs by adjusting the amount of gas permeating the diaphragm. So there is no overreaction and there is a significant risk of explosion Decrease.
- the oxygen-containing organic compound generated on one surface of the diaphragm is constantly swept away by a raw material hydrocarbon or a diluent, so that the sequential oxidation of the oxygen-containing organic compound is suppressed. Helps achieve selectivity, resulting in high yields.
- a tube used as a porous membrane was manufactured according to the method described in Example 1 of Patent No. 18550556. That is, using ⁇ -alumina powder having a particle size of 0.3 m, a porous tube made of ⁇ -alumina having an outer diameter of about 2.0 mm, an inner diameter of about 1.6 mm, and a pore diameter of 0.2 was produced. Its specific surface area measured by the mercury intrusion method was 6 m 2 Zg, and the porosity was 43 V 0 I%.
- Example 3 Except that propylene, oxygen and nitrogen were supplied at a rate of 0.04 mmol / min, 0.06 mmol I / min and 0.73 mmol / min, respectively, to the reaction compound retaining section 1 of the same reactor as in Example 1. The reaction was carried out under the same conditions as in Example 1. As a result of the analysis, the oxygen-containing organic compound was acetone, the conversion of propylene was 28 mO I%, and the selectivity for acetone was 76 m 0 I% based on the raw material propylene. Therefore, the yield in this case is 21 m 0 I%.
- Example 3 Example 3
- a benzene oxidation reaction was carried out using the reaction vessel of FIG. 3 incorporating the palladium-supported porous membrane produced in Reference Example 1 as a membrane catalyst. That is, 12.5% hydrogen gas diluted with helium was introduced into the activated substance flowing section 2 of FIG. 3 from the activated substance inlet 6. On the other hand, 5.2% concentration oxygen and 1.6% benzene were introduced into the reaction compound retaining section 1 at a flow rate of 25 ml, respectively. The reactor was heated and reacted continuously at a reaction temperature of 150 ° C. After reacting for 3 hours, a part of the mixed gas was sampled and analyzed. Phenol was obtained as the main product, with a benzene conversion of 13.25% and a phenol yield of 11.3%.
- Example 4 The same reaction as in Example 4 was performed while changing the oxygen concentration and the benzene concentration. That is, 25.0% hydrogen gas diluted with 6 helium at the inlet of the activator was introduced into the activator flow section 2. On the other hand, the reaction compound In 1 were introduced 1.6% oxygen and 10% benzene at a flow rate of 35 ml / h, respectively. The reaction was carried out at a reaction temperature of 160 ° C, and the product was collected and analyzed in the same manner as in Example 4. The main product was phenol, with a benzene conversion rate of 1.6% and a phenol yield of 1. It was 54%.
- Example 6 Example 6
- Example 7 The same reaction as in Example 4 was performed while changing the benzene concentration and the oxygen concentration. Helium-diluted 30.0% concentration hydrogen gas was introduced into the activated substance flowing section 2 from the activated substance inlet 6. On the other hand, 25% oxygen and 1.8% benzene were introduced into the reaction compound retaining section 1 at a flow rate of 35 mI / h, respectively. The reaction was carried out at a reaction temperature of 250 ° C., and the product was analyzed. The main product was phenol, the conversion of benzene was 2.05%, and the yield of phenol was 1.9%.
- Example 7 Example 7
- Example 4 the test was conducted by reversing the introduction pipes of hydrogen, oxygen, and benzene. That is, helium-diluted 10.0% hydrogen gas was introduced into the reaction compound retaining section 1 in Fig. 3, and conversely, 5% oxygen and 0.8% Benzene was introduced at a flow rate of 25 mIh each.
- the reaction was carried out at a reaction temperature of 150 ° C., the main product was phenol, and the conversion of benzene was 2.11% and the yield of phenol was 2.00%.
- Example 9 The reaction and analysis were conducted in the same manner as in Example 4 except that the reaction temperature was set at 200 ° C.
- the main product was phenol, and the conversion of benzene was 12.30%.
- the yield of phenol was 11.0%.
- Example 1 The reaction was carried out in the same manner as in Example 4 except that the reaction temperature was set at 200 ° C.
- the main product was phenol, the conversion of benzene was 3.00%, and the yield of phenol was 2.8%. .
- Example 1 0
- Example 1 2 The reaction was carried out under the conditions of Example 8, and a mixed gas after 24 hours was collected and analyzed.
- the main product was phenol, the conversion of benzene was 11.30%, and the phenol yield was 10.0%.
- Example 1 2 The main product was phenol, the conversion of benzene was 11.30%, and the phenol yield was 10.0%.
- the reaction was carried out under the conditions of Example 10, and after 24 hours, the mixed gas was sampled and analyzed.
- a liquid phase reaction was carried out using the palladium-supported porous membrane produced in Reference Example 1 as a diaphragm catalyst. That is, the reaction compound retention section 1 Inside, 25 mI of benzene was charged from the reaction compound inlet 4a. Next, oxygen was introduced into the retention section 1 from the reaction compound inlet 4 b, and hydrogen was introduced from the activation substance distribution section 2. Oxygen was allowed to reach the diaphragm-type catalyst wall 3 as bubbles through the bubbler 10 as appropriate.
- Example 13 After the reaction of Example 13, the aromatic phase was newly replaced and the experiment was repeated. That is, after the reaction for 24 hours, oxygen was again introduced from the reaction compound inlet 4b into the 25 mI benzene in the reaction compound retaining section, and hydrogen was introduced from the activating substance flowing section 2. The reaction was carried out under the same conditions as in Example 13, and after 24 hours, the main product was phenol, with a conversion of benzene of 9.5% and a phenol yield of 8.4%.
- Example 1 5 Example 1 5
- Example 1 6 The reaction was carried out in the same manner as in Example 4 except that benzene was changed to toluene.
- the main product was an aromatic alcohol (cresols), with a conversion of toluene of 42% and an aromatic alcohol yield of 37%.
- Example 1 6 An aromatic alcohol (cresols), with a conversion of toluene of 42% and an aromatic alcohol yield of 37%.
- Example 1 9 The reaction was carried out in the same manner as in Example 4 except that a silver-palladium alloy-supported membrane (the weight ratio of silver and palladium was 20:80) was used instead of the palladium-supported porous membrane.
- the main product was phenol, with a benzene conversion of 11% and a phenol yield of 9.9%.
- the reaction was carried out in the same manner as in Example 4, except that a nickel-vanadium alloy-supported (nickel-vanadium weight ratio was 1:15) diaphragm was used instead of the palladium-supported porous membrane.
- the main product was phenol, with a benzene conversion of 10.5% and a phenol yield of 9.6%.
- one of the substances in the reaction is reactivated by passing through a membrane catalyst, and the reaction is carried out using the activated substance. Is what you can do.
- aromatic alcohol can be obtained safely and advantageously.
- the contact between the activated substance and the compound reacting with the activated substance can be freely controlled, so that the overreaction of the target product can be prevented and the target compound can be produced in high yield. be able to.
- the process of the present invention is extremely economically advantageous as an industrial process for producing oxygen-containing organic compounds such as aromatic alcohols, ketones, aldehydes, carboxylic acids and epoxides.
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP01273197A EP1357103B1 (en) | 2001-01-05 | 2001-12-27 | Reaction apparatus and method for producing an oxygen-containing organic compound |
US10/451,624 US6911563B2 (en) | 2001-01-05 | 2001-12-27 | Reaction method utilizing diaphram type catalyst and apparatus therefor |
CA002434162A CA2434162C (en) | 2001-01-05 | 2001-12-27 | Reaction method utilizing diaphram type catalyst and apparatus therefor |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2001-403 | 2001-01-05 | ||
JP2001000403A JP2002205968A (ja) | 2001-01-05 | 2001-01-05 | 隔膜型触媒を備えた反応装置 |
JP2001088282A JP2002284727A (ja) | 2001-03-26 | 2001-03-26 | 芳香族アルコール類の製造方法 |
JP2001-88282 | 2001-03-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2002055465A1 true WO2002055465A1 (fr) | 2002-07-18 |
Family
ID=26607348
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2001/011542 WO2002055465A1 (fr) | 2001-01-05 | 2001-12-27 | Methode et appareil de reaction chimique faisant appel a un catalyseur a membrane |
Country Status (4)
Country | Link |
---|---|
US (1) | US6911563B2 (ja) |
EP (1) | EP1357103B1 (ja) |
CA (1) | CA2434162C (ja) |
WO (1) | WO2002055465A1 (ja) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4828185B2 (ja) * | 2004-09-24 | 2011-11-30 | 昭和電工株式会社 | フッ素ガスの製造方法 |
TWI278346B (en) * | 2004-11-17 | 2007-04-11 | Asahi Kasei Chemicals Corp | Oxidation catalyst and oxidation method |
EP2102179B1 (en) | 2006-12-20 | 2014-08-27 | Shell Internationale Research Maatschappij B.V. | Process for removing poly(propylene oxide) from propylene oxide by membrane separation |
CN101570509B (zh) * | 2008-04-29 | 2012-02-22 | 中国石油化工股份有限公司 | 一种n-氧化吡啶的制备方法 |
DE102008044946B4 (de) * | 2008-08-29 | 2022-06-15 | Evonik Superabsorber Gmbh | Einsatz von Schaumkörpern in Oxidations-Reaktoren zur Herstellung ungesättigter Carbonsäuren |
CN105646153B (zh) * | 2015-12-21 | 2018-04-10 | 安徽工业大学 | 一种负载型Au/C3N4@SBA‑15纳米催化剂催化氧化环己烷的方法 |
CN114874161B (zh) * | 2022-04-22 | 2024-02-02 | 浙江恒逸石化研究院有限公司 | 一种借助中空纤维膜管连续合成与提纯5-羟甲基糠醛的方法 |
CN114907293B (zh) * | 2022-04-29 | 2024-03-05 | 浙江恒逸石化研究院有限公司 | 一种耦合反应与萃取便捷生产5-羟甲基糠醛的方法 |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4411362B1 (ja) * | 1964-06-30 | 1969-05-26 | ||
JPS5429423B2 (ja) * | 1976-06-24 | 1979-09-22 | ||
JPS6051125A (ja) * | 1983-08-31 | 1985-03-22 | Japan Storage Battery Co Ltd | 有機化合物の酸化還元方法 |
JPS6311685A (ja) * | 1986-03-05 | 1988-01-19 | Agency Of Ind Science & Technol | 酸化反応方法 |
JPH03122296A (ja) * | 1989-10-06 | 1991-05-24 | Mitsui Toatsu Chem Inc | 芳香族化合物の部分酸化物の製造方法 |
JPH04364144A (ja) * | 1991-05-10 | 1992-12-16 | Mitsui Toatsu Chem Inc | 芳香族化合物の部分酸化物の製造方法 |
JPH05295578A (ja) * | 1992-04-17 | 1993-11-09 | Japan Energy Corp | 芳香族化合物の部分酸化物の製造方法 |
JPH0657470A (ja) * | 1992-08-05 | 1994-03-01 | Kao Corp | 酸化反応方法及びその装置 |
JPH0672919A (ja) * | 1992-08-28 | 1994-03-15 | Mitsui Toatsu Chem Inc | トルエンの部分酸化物の製造方法 |
JPH11300182A (ja) * | 1998-04-17 | 1999-11-02 | Nok Corp | 水素分離膜の製造方法及びその製造装置 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4014657A (en) * | 1972-05-25 | 1977-03-29 | Vladimir Mikhailovich Gryaznov | Catalytic-reactor for carrying out conjugate chemical reactions |
JPH05238961A (ja) | 1992-02-28 | 1993-09-17 | Tokyo Gas Co Ltd | C2 炭化水素の製造方法および該方法に用いられる装置 |
US5223102A (en) * | 1992-03-03 | 1993-06-29 | E. I. Du Pont De Nemours And Company | Process for the electrooxidation of methanol to formaldehyde and methylal |
JPH061738A (ja) | 1992-06-17 | 1994-01-11 | Mitsui Toatsu Chem Inc | フェノールおよびグリコールモノエステル類の併産法 |
EP0893183A3 (en) * | 1993-03-02 | 1999-02-24 | SRI International | Exothermic process with porous means to control reacton rate and exothermic heat |
JPH0769950A (ja) | 1993-07-09 | 1995-03-14 | Mitsui Toatsu Chem Inc | 芳香族ヒドロキシ化合物の製造方法 |
US6033632A (en) * | 1993-12-08 | 2000-03-07 | Eltron Research, Inc. | Solid state oxygen anion and electron mediating membrane and catalytic membrane reactors containing them |
US5625084A (en) | 1996-01-31 | 1997-04-29 | Arco Chemical Technology, L.P. | Vapor phase oxidation of propylene to propylene oxide |
-
2001
- 2001-12-27 CA CA002434162A patent/CA2434162C/en not_active Expired - Lifetime
- 2001-12-27 EP EP01273197A patent/EP1357103B1/en not_active Expired - Lifetime
- 2001-12-27 US US10/451,624 patent/US6911563B2/en not_active Expired - Lifetime
- 2001-12-27 WO PCT/JP2001/011542 patent/WO2002055465A1/ja active Application Filing
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4411362B1 (ja) * | 1964-06-30 | 1969-05-26 | ||
JPS5429423B2 (ja) * | 1976-06-24 | 1979-09-22 | ||
JPS6051125A (ja) * | 1983-08-31 | 1985-03-22 | Japan Storage Battery Co Ltd | 有機化合物の酸化還元方法 |
JPS6311685A (ja) * | 1986-03-05 | 1988-01-19 | Agency Of Ind Science & Technol | 酸化反応方法 |
JPH03122296A (ja) * | 1989-10-06 | 1991-05-24 | Mitsui Toatsu Chem Inc | 芳香族化合物の部分酸化物の製造方法 |
JPH04364144A (ja) * | 1991-05-10 | 1992-12-16 | Mitsui Toatsu Chem Inc | 芳香族化合物の部分酸化物の製造方法 |
JPH05295578A (ja) * | 1992-04-17 | 1993-11-09 | Japan Energy Corp | 芳香族化合物の部分酸化物の製造方法 |
JPH0657470A (ja) * | 1992-08-05 | 1994-03-01 | Kao Corp | 酸化反応方法及びその装置 |
JPH0672919A (ja) * | 1992-08-28 | 1994-03-15 | Mitsui Toatsu Chem Inc | トルエンの部分酸化物の製造方法 |
JPH11300182A (ja) * | 1998-04-17 | 1999-11-02 | Nok Corp | 水素分離膜の製造方法及びその製造装置 |
Non-Patent Citations (2)
Title |
---|
NIWA S. ET AL.: "A one-step conversion of benzene to phenol with a palladium membrane", SCIENCE, vol. 295, 4 January 2002 (2002-01-04), pages 105 - 107, XP002950351 * |
See also references of EP1357103A4 * |
Also Published As
Publication number | Publication date |
---|---|
CA2434162C (en) | 2010-02-02 |
CA2434162A1 (en) | 2002-07-18 |
US6911563B2 (en) | 2005-06-28 |
US20040110995A1 (en) | 2004-06-10 |
EP1357103A4 (en) | 2006-04-26 |
EP1357103A1 (en) | 2003-10-29 |
EP1357103B1 (en) | 2013-02-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US6143928A (en) | Catalysts for low temperature selective oxidation of propylene, methods of making and using the same | |
EP1342710B1 (en) | Method for catalytic dehydrogenation of hydrocarbons using carbon dioxide as a soft oxidant | |
TWI268920B (en) | Preparation of acrolein or acrylic acid or a mixture thereof from propane | |
TWI359131B (en) | Integrated catalytic process for converting alkane | |
Ziaka et al. | A high temperature catalytic membrane reactor for propane dehydrogenation | |
US6956134B2 (en) | Oxidation of methanol and/or dimethyl ether using supported molybdenum-containing heteropolyacid catalysts | |
US5202517A (en) | Process for production of ethylene from ethane | |
US20110196182A1 (en) | Styrene production processes and catalysts for use therein | |
Dalmon et al. | Oxidation in catalytic membrane reactors | |
WO2002055465A1 (fr) | Methode et appareil de reaction chimique faisant appel a un catalyseur a membrane | |
Capannelli et al. | Comparison of the catalytic performance of V2O5/γ-Al2O3 in the oxidehydrogenation of propane to propylene in different reactor configurations: i) packed-bed reactor, ii) monolith-like reactor and iii) Catalytic Membrane Reactor | |
US6458737B1 (en) | Catalyst for oxidizing methylbenzenes and method for producing aromatic aldehyde | |
Kölsch et al. | Development of a membrane reactor for the partial oxidation of hydrocarbons: direct oxidation of propane to acrolein | |
HU180654B (en) | Process for producing nitrozo-benzene | |
JPH05194281A (ja) | 炭化水素類の脱水素方法 | |
JP2002205968A (ja) | 隔膜型触媒を備えた反応装置 | |
GB2201159A (en) | Process and apparatus for the dehydrogenation of organic compounds | |
JP4193967B2 (ja) | 隔膜型触媒を用いるプロピレンオキシドの製造方法 | |
JP2002284727A (ja) | 芳香族アルコール類の製造方法 | |
JP5110561B2 (ja) | 超臨界二酸化炭素反応方法及び装置 | |
Capannelli et al. | Enhancement of the catalytic performance of V 2 O 5/γ-Al 2 O 3 catalysts in the oxidehydrogenation of propane to propylene by the use of a monolith-type reactor | |
RU2137702C1 (ru) | Способ каталитического частичного окисления углеводородов | |
JP4129830B2 (ja) | 環状飽和アルコール類の製造法 | |
Raabová | New catalytic processes for the synthesis of adipic acid | |
WO2013053032A1 (pt) | Processo de obtenção de ácido acético a partir de etanol |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SD SE SG SI SK SL TJ TM TN TR TT TZ UA UG US UZ VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2001273197 Country of ref document: EP Ref document number: 2434162 Country of ref document: CA |
|
WWP | Wipo information: published in national office |
Ref document number: 2001273197 Country of ref document: EP |
|
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 10451624 Country of ref document: US |