EA004784B1 - Микропористые материалы (tiq-6 и metiq-6) с большой площадью поверхности, проявляющие активность в окислительных реакциях - Google Patents
Микропористые материалы (tiq-6 и metiq-6) с большой площадью поверхности, проявляющие активность в окислительных реакциях Download PDFInfo
- Publication number
- EA004784B1 EA004784B1 EA200200583A EA200200583A EA004784B1 EA 004784 B1 EA004784 B1 EA 004784B1 EA 200200583 A EA200200583 A EA 200200583A EA 200200583 A EA200200583 A EA 200200583A EA 004784 B1 EA004784 B1 EA 004784B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- groups
- organic
- combinations
- carbon atoms
- hydroperoxide
- Prior art date
Links
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 15
- 230000003647 oxidation Effects 0.000 title claims abstract description 14
- 239000012229 microporous material Substances 0.000 title claims abstract description 11
- 239000000463 material Substances 0.000 claims abstract description 119
- 238000000034 method Methods 0.000 claims abstract description 59
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 30
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000003054 catalyst Substances 0.000 claims abstract description 26
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 26
- 239000010936 titanium Substances 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 239000002243 precursor Substances 0.000 claims abstract description 24
- -1 trimethylsilylamino groups Chemical group 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 22
- 150000002432 hydroperoxides Chemical class 0.000 claims abstract description 21
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 claims abstract description 20
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000006735 epoxidation reaction Methods 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 15
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 claims abstract description 15
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 14
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 14
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 12
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 150000001336 alkenes Chemical class 0.000 claims abstract description 10
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 10
- 150000001298 alcohols Chemical class 0.000 claims abstract description 9
- 235000012239 silicon dioxide Nutrition 0.000 claims abstract description 9
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 9
- 150000003573 thiols Chemical class 0.000 claims abstract description 9
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 8
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000002576 ketones Chemical class 0.000 claims abstract description 8
- 238000002156 mixing Methods 0.000 claims abstract description 8
- 150000002902 organometallic compounds Chemical class 0.000 claims abstract description 8
- 239000011148 porous material Substances 0.000 claims abstract description 8
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 150000001282 organosilanes Chemical class 0.000 claims abstract description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052732 germanium Inorganic materials 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 6
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 6
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000010306 acid treatment Methods 0.000 claims abstract description 5
- 125000000524 functional group Chemical group 0.000 claims abstract description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims abstract description 5
- FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 claims abstract description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000005700 Putrescine Substances 0.000 claims abstract description 4
- 125000004429 atom Chemical group 0.000 claims abstract description 4
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000004820 halides Chemical class 0.000 claims abstract description 4
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 4
- 230000033444 hydroxylation Effects 0.000 claims abstract description 4
- 238000005805 hydroxylation reaction Methods 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000001694 spray drying Methods 0.000 claims abstract description 4
- 230000008961 swelling Effects 0.000 claims abstract description 4
- PDSNLYSELAIEBU-UHFFFAOYSA-N Longifolene Chemical compound C1CCC(C)(C)C2C3CCC2C1(C)C3=C PDSNLYSELAIEBU-UHFFFAOYSA-N 0.000 claims abstract description 3
- ZPUKHRHPJKNORC-UHFFFAOYSA-N Longifolene Natural products CC1(C)CCCC2(C)C3CCC1(C3)C2=C ZPUKHRHPJKNORC-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 3
- 150000001343 alkyl silanes Chemical class 0.000 claims abstract description 3
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 3
- 238000001354 calcination Methods 0.000 claims abstract description 3
- 239000007789 gas Substances 0.000 claims abstract description 3
- 229910001867 inorganic solvent Inorganic materials 0.000 claims abstract description 3
- 239000003049 inorganic solvent Substances 0.000 claims abstract description 3
- 229940087305 limonene Drugs 0.000 claims abstract description 3
- 235000001510 limonene Nutrition 0.000 claims abstract description 3
- 150000003440 styrenes Chemical class 0.000 claims abstract description 3
- 238000002604 ultrasonography Methods 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims abstract 4
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000010457 zeolite Substances 0.000 claims description 11
- 229910001657 ferrierite group Inorganic materials 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 6
- 238000001228 spectrum Methods 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 claims description 4
- 230000005855 radiation Effects 0.000 claims description 4
- 150000003462 sulfoxides Chemical class 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 238000004108 freeze drying Methods 0.000 claims description 3
- 239000011368 organic material Substances 0.000 claims description 3
- 125000000082 organogermanium group Chemical group 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims description 3
- IPCAPQRVQMIMAN-UHFFFAOYSA-L zirconyl chloride Chemical compound Cl[Zr](Cl)=O IPCAPQRVQMIMAN-UHFFFAOYSA-L 0.000 claims description 3
- 150000004808 allyl alcohols Chemical class 0.000 claims description 2
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims description 2
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- XGZNHFPFJRZBBT-UHFFFAOYSA-N ethanol;titanium Chemical compound [Ti].CCO.CCO.CCO.CCO XGZNHFPFJRZBBT-UHFFFAOYSA-N 0.000 claims 2
- 150000004665 fatty acids Chemical class 0.000 claims 2
- KIFPIAKBYOIOCS-UHFFFAOYSA-N 2-methyl-2-(trioxidanyl)propane Chemical class CC(C)(C)OOO KIFPIAKBYOIOCS-UHFFFAOYSA-N 0.000 claims 1
- KOOADCGQJDGAGA-UHFFFAOYSA-N [amino(dimethyl)silyl]methane Chemical group C[Si](C)(C)N KOOADCGQJDGAGA-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- SVURIXNDRWRAFU-OGMFBOKVSA-N cedrol Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1[C@@](O)(C)CC2 SVURIXNDRWRAFU-OGMFBOKVSA-N 0.000 claims 1
- PCROEXHGMUJCDB-UHFFFAOYSA-N cedrol Natural products CC1CCC2C(C)(C)C3CC(C)(O)CC12C3 PCROEXHGMUJCDB-UHFFFAOYSA-N 0.000 claims 1
- SVURIXNDRWRAFU-UHFFFAOYSA-N juniperanol Natural products C1C23C(C)CCC3C(C)(C)C1C(O)(C)CC2 SVURIXNDRWRAFU-UHFFFAOYSA-N 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 abstract description 3
- 229910052782 aluminium Inorganic materials 0.000 abstract description 3
- 239000005416 organic matter Substances 0.000 abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 3
- 229910052710 silicon Inorganic materials 0.000 abstract description 3
- 150000007513 acids Chemical class 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 229910052718 tin Inorganic materials 0.000 abstract 4
- 229910052681 coesite Inorganic materials 0.000 abstract 3
- 229910052906 cristobalite Inorganic materials 0.000 abstract 3
- 229910052682 stishovite Inorganic materials 0.000 abstract 3
- 229910052905 tridymite Inorganic materials 0.000 abstract 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract 2
- 229910052733 gallium Inorganic materials 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 238000002211 ultraviolet spectrum Methods 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 229910003074 TiCl4 Inorganic materials 0.000 abstract 1
- 229910007932 ZrCl4 Inorganic materials 0.000 abstract 1
- 150000002194 fatty esters Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000010907 mechanical stirring Methods 0.000 abstract 1
- 125000002524 organometallic group Chemical group 0.000 abstract 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 abstract 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 abstract 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 230000003197 catalytic effect Effects 0.000 description 18
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- 150000002118 epoxides Chemical class 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000011521 glass Substances 0.000 description 7
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 5
- ASRSBXRMOCLKQC-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)-n-methoxyacetamide Chemical compound CONC(=O)COC1=CC=C(Cl)C=C1C ASRSBXRMOCLKQC-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 230000032798 delamination Effects 0.000 description 2
- BYLOHCRAPOSXLY-UHFFFAOYSA-N dichloro(diethyl)silane Chemical compound CC[Si](Cl)(Cl)CC BYLOHCRAPOSXLY-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 150000004673 fluoride salts Chemical class 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000009830 intercalation Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000002444 silanisation Methods 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 2
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- YXHQEJLMUHAYAA-UHFFFAOYSA-N 1-hydroxysiline Chemical group O[Si]1=CC=CC=C1 YXHQEJLMUHAYAA-UHFFFAOYSA-N 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- NILZGRNPRBIQOG-UHFFFAOYSA-N 3-iodopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCI NILZGRNPRBIQOG-UHFFFAOYSA-N 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- MKNXBRLZBFVUPV-UHFFFAOYSA-L cyclopenta-1,3-diene;dichlorotitanium Chemical compound Cl[Ti]Cl.C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 MKNXBRLZBFVUPV-UHFFFAOYSA-L 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 150000002291 germanium compounds Chemical class 0.000 description 1
- WJLUBOLDZCQZEV-UHFFFAOYSA-M hexadecyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCCCCCC[N+](C)(C)C WJLUBOLDZCQZEV-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000002687 intercalation Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000013335 mesoporous material Substances 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
Classifications
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0231—Halogen-containing compounds
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/89—Silicates, aluminosilicates or borosilicates of titanium, zirconium or hafnium
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0201—Oxygen-containing compounds
- B01J31/0211—Oxygen-containing compounds with a metal-oxygen link
- B01J31/0212—Alkoxylates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0272—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255
- B01J31/0274—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255 containing silicon
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0272—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255
- B01J31/0275—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255 also containing elements or functional groups covered by B01J31/0201 - B01J31/0269
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/38—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of titanium, zirconium or hafnium
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- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B37/00—Compounds having molecular sieve properties but not having base-exchange properties
- C01B37/005—Silicates, i.e. so-called metallosilicalites or metallozeosilites
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- C01B39/02—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof; Direct preparation thereof; Preparation thereof starting from a reaction mixture containing a crystalline zeolite of another type, or from preformed reactants; After-treatment thereof
- C01B39/06—Preparation of isomorphous zeolites characterised by measures to replace the aluminium or silicon atoms in the lattice framework by atoms of other elements, i.e. by direct or secondary synthesis
- C01B39/08—Preparation of isomorphous zeolites characterised by measures to replace the aluminium or silicon atoms in the lattice framework by atoms of other elements, i.e. by direct or secondary synthesis the aluminium atoms being wholly replaced
- C01B39/085—Group IVB- metallosilicates
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- C01B39/00—Compounds having molecular sieve and base-exchange properties, e.g. crystalline zeolites; Their preparation; After-treatment, e.g. ion-exchange or dealumination
- C01B39/02—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof; Direct preparation thereof; Preparation thereof starting from a reaction mixture containing a crystalline zeolite of another type, or from preformed reactants; After-treatment thereof
- C01B39/46—Other types characterised by their X-ray diffraction pattern and their defined composition
- C01B39/48—Other types characterised by their X-ray diffraction pattern and their defined composition using at least one organic template directing agent
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- C07B41/00—Formation or introduction of functional groups containing oxygen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
- B01J2231/72—Epoxidation
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- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S423/00—Chemistry of inorganic compounds
- Y10S423/23—Ferrierite, e.g. SR-D ZSM-33
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- Life Sciences & Earth Sciences (AREA)
- Inorganic Chemistry (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Geology (AREA)
- Catalysts (AREA)
- Silicates, Zeolites, And Molecular Sieves (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES009902655A ES2178910B1 (es) | 1999-11-24 | 1999-11-24 | Materiales microporosos de alta superficie activos en reacciones de oxidacion. tiq-6 y metiq-6. |
| PCT/ES2000/000456 WO2001037629A2 (es) | 1999-11-24 | 2000-11-24 | Materiales microporosos de alta superficie activos en reacciones de oxidación. tiq-6 y metiq-6 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200200583A1 EA200200583A1 (ru) | 2003-04-24 |
| EA004784B1 true EA004784B1 (ru) | 2004-08-26 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| EA200200583A EA004784B1 (ru) | 1999-11-24 | 2000-11-24 | Микропористые материалы (tiq-6 и metiq-6) с большой площадью поверхности, проявляющие активность в окислительных реакциях |
Country Status (13)
| Country | Link |
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| US (1) | US6843978B2 (enExample) |
| EP (1) | EP1243333B1 (enExample) |
| JP (1) | JP2003514751A (enExample) |
| CN (1) | CN1191884C (enExample) |
| AT (1) | ATE286432T1 (enExample) |
| AU (1) | AU782301B2 (enExample) |
| DE (1) | DE60017286T2 (enExample) |
| DK (1) | DK1243333T3 (enExample) |
| EA (1) | EA004784B1 (enExample) |
| ES (2) | ES2178910B1 (enExample) |
| IN (1) | IN2002KO00840A (enExample) |
| NZ (1) | NZ519657A (enExample) |
| WO (1) | WO2001037629A2 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2179753B1 (es) | 2000-10-11 | 2005-02-16 | Universidad Politecnica De Valencia | Proceso y catalizadores para la eliminacion de compuestos de azufre de la fraccion gasolina. |
| ES2183710B1 (es) | 2001-04-12 | 2004-01-16 | Univ Valencia Politecnica | Proceso y catalizadores para la eliminacion de compuestos de azufre de la fraccion diesel. |
| WO2005012458A1 (en) * | 2003-08-01 | 2005-02-10 | Bp Corporation North America Inc. | Preparation of components for refinery blending of transportation fuels |
| US7491316B2 (en) * | 2004-07-29 | 2009-02-17 | Bp Corporation North America Inc. | Preparation of components for refinery blending of transportation fuels |
| ES2281299B1 (es) * | 2006-03-15 | 2008-12-16 | Universidad Politecnica De Valencia | Un procecimiento para la sintesis de esteres. |
| GB0702327D0 (en) * | 2007-02-07 | 2007-03-21 | Leuven K U Res & Dev | Zeolite materials and synthesis method thereof |
| CN101602012B (zh) * | 2008-06-12 | 2012-04-18 | 中国石油化工股份有限公司 | 含有芳烃磺酸基团的介孔材料及其制备方法和应用 |
| TWI399242B (zh) * | 2009-12-11 | 2013-06-21 | China Petrochemical Dev Corp Taipei Taiwan | Method for preparing large-diameter titanium-silicon molecular sieve and method for producing cyclohexanone oxime using the molecular sieve |
| US9522390B2 (en) * | 2010-12-10 | 2016-12-20 | The Regents Of The University Of California | Oxide materials and synthesis by fluoride/chloride anion promoted exfoliation |
| EA201391089A1 (ru) * | 2011-01-27 | 2014-06-30 | Солвей Са | Способ изготовления 1,2-эпокси-3-хлорпропана |
| CN102442683A (zh) * | 2011-09-27 | 2012-05-09 | 华东理工大学 | 一种制备多级孔道含钛沸石的溶剂挥发法 |
| KR101394133B1 (ko) * | 2012-08-22 | 2014-05-15 | 주식회사 이엔에프테크놀로지 | 몰리브덴 합금막 및 인듐 산화막 식각액 조성물 |
| JP6385428B2 (ja) * | 2013-05-29 | 2018-09-05 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | スルホキシドを酸化する方法 |
| FR3007405B1 (fr) * | 2013-06-21 | 2016-07-29 | Centre Nat De La Rech Scient (C N R S ) | Procede de preparation d'une composition comprenant des particules silico/germano-metalliques fonctionnalisees et composition obtenue |
| JP2021501117A (ja) * | 2017-10-30 | 2021-01-14 | ビーエイエスエフ・ソシエタス・エウロパエアＢａｓｆ Ｓｅ | 層状ケイ酸塩前駆体から遷移金属ナノ粒子をカプセル化したゼオライトの調製方法 |
| CN108947939B (zh) * | 2018-08-16 | 2022-03-11 | 福州大学 | 一种异松油烯4,8-环氧化物的合成方法 |
| CN111924852B (zh) * | 2019-04-26 | 2023-11-03 | 中国石油大学(华东) | 一种钛硅分子筛的制备方法 |
| CN110902691B (zh) * | 2019-11-25 | 2021-07-20 | 北京化工大学 | 一种y型分子筛疏水改性的方法 |
| CN111167471B (zh) * | 2020-01-17 | 2020-10-02 | 浙江新和成股份有限公司 | 一种金属氧化物涂覆的陶瓷波纹板催化剂、制备及其在制备柠檬醛关键中间体中的应用 |
| WO2023210199A1 (ja) * | 2022-04-25 | 2023-11-02 | 住友化学株式会社 | チタン含有珪素酸化物の製造方法、エポキシドの製造方法、及びチタン含有珪素酸化物 |
| CN118620617B (zh) * | 2024-08-09 | 2025-03-04 | 电子科技大学长三角研究院(湖州) | 一种晶态GaTiS-AEP有机开放骨架绿色光致发光源及其制备方法 |
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| US3923843A (en) | 1972-03-13 | 1975-12-02 | Shell Oil Co | Epoxidation process with improved heterogeneous catalyst |
| US4016245A (en) * | 1973-09-04 | 1977-04-05 | Mobil Oil Corporation | Crystalline zeolite and method of preparing same |
| US3966883A (en) * | 1974-10-16 | 1976-06-29 | W. R. Grace & Co. | Synthetic ferrierite synthesis |
| DK84884A (da) * | 1983-03-07 | 1984-09-08 | Res Ass Petroleum Alternat Dev | Krystallinsk aluminiumsilicat og fremgangsmaade til fremstilling deraf |
| GB8818452D0 (en) * | 1988-08-03 | 1988-09-07 | British Petroleum Co Plc | Process for preparation of crystalline(metallo)silicates & germanates |
| US5374747A (en) * | 1993-12-23 | 1994-12-20 | Arco Chemical Technology, L.P. | Epoxidation process and catalyst therefore |
| ES2124154B1 (es) * | 1995-11-08 | 1999-12-01 | Univ Politecnica De Valencia C | Metodo de preparaciion y propiedades cataliticas de un solido microporoso con alta superficie externa. |
| ES2137885B1 (es) * | 1997-12-19 | 2000-08-16 | Univ Valencia Politecnica | Zeolita itq-5. |
| BR9912641B1 (pt) * | 1998-08-04 | 2010-07-13 | sólido microporoso deslaminado. | |
| ES2156514B1 (es) * | 1998-12-04 | 2002-02-16 | Univ Valencia Politecnica | Materiales microporosos de alta superficie activos en reacciones de oxidacion. |
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1999
- 1999-11-24 ES ES009902655A patent/ES2178910B1/es not_active Expired - Fee Related
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2000
- 2000-11-24 EA EA200200583A patent/EA004784B1/ru not_active IP Right Cessation
- 2000-11-24 EP EP00979683A patent/EP1243333B1/en not_active Expired - Lifetime
- 2000-11-24 ES ES00979683T patent/ES2236000T3/es not_active Expired - Lifetime
- 2000-11-24 JP JP2001539268A patent/JP2003514751A/ja active Pending
- 2000-11-24 NZ NZ51965700A patent/NZ519657A/en unknown
- 2000-11-24 AU AU17085/01A patent/AU782301B2/en not_active Ceased
- 2000-11-24 AT AT00979683T patent/ATE286432T1/de not_active IP Right Cessation
- 2000-11-24 DE DE60017286T patent/DE60017286T2/de not_active Expired - Lifetime
- 2000-11-24 DK DK00979683T patent/DK1243333T3/da active
- 2000-11-24 WO PCT/ES2000/000456 patent/WO2001037629A2/es not_active Ceased
- 2000-11-24 CN CNB008186006A patent/CN1191884C/zh not_active Expired - Fee Related
-
2002
- 2002-05-24 US US10/155,564 patent/US6843978B2/en not_active Expired - Fee Related
- 2002-06-24 IN IN840KO2002 patent/IN2002KO00840A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001037629A2 (es) | 2001-05-31 |
| WO2001037629A8 (es) | 2003-02-06 |
| ATE286432T1 (de) | 2005-01-15 |
| EP1243333A2 (en) | 2002-09-25 |
| DK1243333T3 (da) | 2005-04-25 |
| CN1424938A (zh) | 2003-06-18 |
| ES2236000T3 (es) | 2005-07-16 |
| ES2178910B1 (es) | 2003-12-16 |
| US20020193239A1 (en) | 2002-12-19 |
| AU782301B2 (en) | 2005-07-14 |
| EP1243333B1 (en) | 2005-01-05 |
| EA200200583A1 (ru) | 2003-04-24 |
| WO2001037629A3 (es) | 2002-03-14 |
| IN2002KO00840A (enExample) | 2006-03-10 |
| CN1191884C (zh) | 2005-03-09 |
| JP2003514751A (ja) | 2003-04-22 |
| NZ519657A (en) | 2004-01-30 |
| DE60017286T2 (de) | 2005-12-08 |
| ES2178910A1 (es) | 2003-01-01 |
| US6843978B2 (en) | 2005-01-18 |
| DE60017286D1 (de) | 2005-02-10 |
| AU1708501A (en) | 2001-06-04 |
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