SK6752000A3 - Process for the selective oxidation of organic compounds - Google Patents

Process for the selective oxidation of organic compounds Download PDF

Info

Publication number: SK6752000A3
Authority: SK; Slovakia
Prior art keywords: catalyst; group; hydrogen peroxide; formula; integer
Prior art date: 1997-11-14

Application number

SK675-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Prahlad R Singh

Gerald P Tercho

Jack N Wentz Jr

Keith R Olewine

Original Assignee

Du Pont Pharm Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-11-14

Filing date

1998-11-12

Publication date

2000-10-09

1998-11-12 Application filed by Du Pont Pharm Co filed Critical Du Pont Pharm Co

2000-10-09 Publication of SK6752000A3 publication Critical patent/SK6752000A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 35
150000002894 organic compounds Chemical class 0.000 title claims abstract description 15
238000007254 oxidation reaction Methods 0.000 title description 20
230000003647 oxidation Effects 0.000 title description 18
239000003054 catalyst Substances 0.000 claims abstract description 74
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 55
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 21
239000000377 silicon dioxide Substances 0.000 claims abstract description 9
229920001577 copolymer Polymers 0.000 claims abstract description 7
ZXPDYFSTVHQQOI-UHFFFAOYSA-N diethoxysilane Chemical compound CCO[SiH2]OCC ZXPDYFSTVHQQOI-UHFFFAOYSA-N 0.000 claims abstract description 5
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 5
230000001590 oxidative effect Effects 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 40
239000010936 titanium Substances 0.000 claims description 25
150000001336 alkenes Chemical class 0.000 claims description 21
-1 cyclic olefins Chemical class 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 16
239000003795 chemical substances by application Substances 0.000 claims description 14
229910052719 titanium Inorganic materials 0.000 claims description 13
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 8
229930195733 hydrocarbon Natural products 0.000 claims description 8
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
229910052751 metal Inorganic materials 0.000 claims description 7
239000002184 metal Substances 0.000 claims description 7
150000001298 alcohols Chemical class 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
239000002808 molecular sieve Substances 0.000 claims description 6
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 5
150000003997 cyclic ketones Chemical class 0.000 claims description 5
230000000694 effects Effects 0.000 claims description 5
230000003213 activating effect Effects 0.000 claims description 4
125000002877 alkyl aryl group Chemical group 0.000 claims description 4
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
102220500397 Neutral and basic amino acid transport protein rBAT_M41T_mutation Human genes 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
229910052750 molybdenum Inorganic materials 0.000 claims description 3
239000011733 molybdenum Substances 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
150000001282 organosilanes Chemical class 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
239000010703 silicon Substances 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
229910052720 vanadium Inorganic materials 0.000 claims description 3
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
239000004215 Carbon black (E152) Substances 0.000 claims description 2
229910052684 Cerium Inorganic materials 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
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 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000011651 chromium Substances 0.000 claims description 2
229910052804 chromium Inorganic materials 0.000 claims description 2
229910017052 cobalt Inorganic materials 0.000 claims description 2
239000010941 cobalt Substances 0.000 claims description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
229910052802 copper Inorganic materials 0.000 claims description 2
239000010949 copper Substances 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 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
239000011630 iodine Substances 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
125000005647 linker group Chemical group 0.000 claims description 2
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 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 claims description 2
229910052814 silicon oxide Inorganic materials 0.000 claims description 2
229910052709 silver Inorganic materials 0.000 claims description 2
239000004332 silver Substances 0.000 claims description 2
230000002194 synthesizing effect Effects 0.000 claims description 2
NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 claims 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical class O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract description 11
239000000758 substrate Substances 0.000 abstract description 4
KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 42
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 23
238000006735 epoxidation reaction Methods 0.000 description 15
238000004817 gas chromatography Methods 0.000 description 14
150000002978 peroxides Chemical class 0.000 description 12
239000000243 solution Substances 0.000 description 11
NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 10
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
239000007787 solid Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
238000003756 stirring Methods 0.000 description 8
XCOBLONWWXQEBS-KPKJPENVSA-N N,O-bis(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)O\C(C(F)(F)F)=N\[Si](C)(C)C XCOBLONWWXQEBS-KPKJPENVSA-N 0.000 description 7
GNKTZDSRQHMHLZ-UHFFFAOYSA-N [Si].[Si].[Si].[Ti].[Ti].[Ti].[Ti].[Ti] Chemical compound [Si].[Si].[Si].[Ti].[Ti].[Ti].[Ti].[Ti] GNKTZDSRQHMHLZ-UHFFFAOYSA-N 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 7
239000000463 material Substances 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
238000002441 X-ray diffraction Methods 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
150000002924 oxiranes Chemical class 0.000 description 5
238000006884 silylation reaction Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
MELPJGOMEMRMPL-UHFFFAOYSA-N 9-oxabicyclo[6.1.0]nonane Chemical compound C1CCCCCC2OC21 MELPJGOMEMRMPL-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
150000002432 hydroperoxides Chemical class 0.000 description 4
239000002243 precursor Substances 0.000 description 4
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910010413 TiO 2 Inorganic materials 0.000 description 3
150000001335 aliphatic alkanes Chemical class 0.000 description 3
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
238000006555 catalytic reaction Methods 0.000 description 3
239000011248 coating agent Substances 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 3
OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
229910004298 SiO 2 Inorganic materials 0.000 description 2
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
239000004809 Teflon Substances 0.000 description 2
229920006362 Teflon® Polymers 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
238000000576 coating method Methods 0.000 description 2
229910052681 coesite Inorganic materials 0.000 description 2
229910052906 cristobalite Inorganic materials 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
SFVWPXMPRCIVOK-UHFFFAOYSA-N cyclododecanol Chemical compound OC1CCCCCCCCCCC1 SFVWPXMPRCIVOK-UHFFFAOYSA-N 0.000 description 2
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
229910044991 metal oxide Inorganic materials 0.000 description 2
150000004706 metal oxides Chemical class 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000002923 oximes Chemical class 0.000 description 2
239000002245 particle Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
150000004760 silicates Chemical class 0.000 description 2
229910052710 silicon Inorganic materials 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
238000004611 spectroscopical analysis Methods 0.000 description 2
229910052682 stishovite Inorganic materials 0.000 description 2
LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 2
239000004408 titanium dioxide Substances 0.000 description 2
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
229910052905 tridymite Inorganic materials 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
HTVZZSMSDRZVED-UHFFFAOYSA-N CC[SiH2]N([SiH3])CC Chemical compound CC[SiH2]N([SiH3])CC HTVZZSMSDRZVED-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
229930194542 Keto Chemical group 0.000 description 1
WVGXAWUYNHSWRO-UHFFFAOYSA-N N-propan-2-ylsilyl-N-silylpropan-2-amine Chemical compound CC(C)[SiH2]N([SiH3])C(C)C WVGXAWUYNHSWRO-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
239000005062 Polybutadiene Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000007824 aliphatic compounds Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000008064 anhydrides Chemical group 0.000 description 1
238000000137 annealing Methods 0.000 description 1
238000007262 aromatic hydroxylation reaction Methods 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
VMYTYUVXHJVTTL-UHFFFAOYSA-N bromo-chloro-dimethylsilane Chemical compound C[Si](C)(Cl)Br VMYTYUVXHJVTTL-UHFFFAOYSA-N 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
KWYZNESIGBQHJK-UHFFFAOYSA-N chloro-dimethyl-phenylsilane Chemical compound C[Si](C)(Cl)C1=CC=CC=C1 KWYZNESIGBQHJK-UHFFFAOYSA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical group O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
229910021485 fumed silica Inorganic materials 0.000 description 1
239000003349 gelling agent Substances 0.000 description 1
150000004820 halides Chemical group 0.000 description 1
239000002638 heterogeneous catalyst Substances 0.000 description 1
125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910021331 inorganic silicon compound Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000013335 mesoporous material Substances 0.000 description 1
238000006384 oligomerization reaction Methods 0.000 description 1
125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229920002857 polybutadiene Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
150000004756 silanes Chemical class 0.000 description 1
150000003376 silicon Chemical class 0.000 description 1
150000003377 silicon compounds Chemical class 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003608 titanium Chemical class 0.000 description 1
150000003623 transition metal compounds Chemical class 0.000 description 1
238000011282 treatment Methods 0.000 description 1
150000005671 trienes Chemical class 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
238000012982 x-ray structure analysis Methods 0.000 description 1
239000010457 zeolite Substances 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61N—ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
- A61N5/00—Radiation therapy
- A61N5/10—X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy
- A61N5/1001—X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy using radiation sources introduced into or applied onto the body; brachytherapy
- A61N5/1027—Interstitial radiation therapy
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/12—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by a special physical form, e.g. emulsion, microcapsules, liposomes, characterized by a special physical form, e.g. emulsions, dispersions, microcapsules
- A61K51/1282—Devices used in vivo and carrying the radioactive therapeutic or diagnostic agent, therapeutic or in vivo diagnostic kits, stents
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B41/00—Formation or introduction of functional groups containing oxygen
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61N—ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
- A61N5/00—Radiation therapy
- A61N5/10—X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy
- A61N5/1001—X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy using radiation sources introduced into or applied onto the body; brachytherapy
- A61N2005/1019—Sources therefor
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61N—ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
- A61N5/00—Radiation therapy
- A61N5/10—X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy
- A61N5/1001—X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy using radiation sources introduced into or applied onto the body; brachytherapy
- A61N2005/1019—Sources therefor
- A61N2005/1024—Seeds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Optics & Photonics (AREA)
Biomedical Technology (AREA)
Physics & Mathematics (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Inorganic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Radiology & Medical Imaging (AREA)
Heart & Thoracic Surgery (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Dispersion Chemistry (AREA)
Medicinal Chemistry (AREA)
Pathology (AREA)
Epidemiology (AREA)
Chemical Kinetics & Catalysis (AREA)
Materials Engineering (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Epoxy Compounds (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Radiation-Therapy Devices (AREA)
Prostheses (AREA)
Medicinal Preparation (AREA)
Materials For Medical Uses (AREA)

SK675-2000A 1997-11-14 1998-11-12 Process for the selective oxidation of organic compounds SK6752000A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US6599397P	1997-11-14	1997-11-14
PCT/US1998/024180 WO1999025666A2 (fr)	1997-11-14	1998-11-12	Procede d'oxydation selective de composes organique

Publications (1)

Publication Number	Publication Date
SK6752000A3 true SK6752000A3 (en)	2000-10-09

Family

ID=22066559

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK675-2000A SK6752000A3 (en)	1997-11-14	1998-11-12	Process for the selective oxidation of organic compounds

Country Status (17)

Country	Link
US (1)	US6391279B1 (fr)
EP (1)	EP1056683A2 (fr)
JP (1)	JP2001523651A (fr)
KR (1)	KR20010032082A (fr)
CN (1)	CN1278808A (fr)
AR (1)	AR014027A1 (fr)
AU (1)	AU2197099A (fr)
BR (1)	BR9815311A (fr)
EE (1)	EE200000234A (fr)
HR (1)	HRP980595A2 (fr)
HU (1)	HUP0004411A3 (fr)
IL (1)	IL136124A0 (fr)
NO (1)	NO20002406D0 (fr)
PL (1)	PL340827A1 (fr)
SK (1)	SK6752000A3 (fr)
WO (1)	WO1999025666A2 (fr)
ZA (1)	ZA9810409B (fr)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6547816B1 (en) *	1999-07-12	2003-04-15	Civatech Corporation	Formable integral source material for medical devices
DE19959525A1 (de) *	1999-12-09	2001-06-13	Bayer Ag	Katalysatoren auf Basis Edelmetall- und Titan-haltiger, organisch-anorganisch Hybridmaterialien zur selektiven Oxidation von Kohlenwasserstoffen
ATE359122T1 (de) *	2000-01-31	2007-05-15	Solvay	Verfahren zur oxidation mit einem katalysator von einer antimontrifluorid und siliziumdioxid enthaltenden zusammensatzung
AU2003267309A1 (en)	2000-11-16	2004-04-08	Microspherix Llc	Flexible and/or elastic brachytherapy seed or strand
US6746661B2 (en)	2000-11-16	2004-06-08	Microspherix Llc	Brachytherapy seed
CN1926124B (zh) *	2004-03-31	2011-03-23	科学与工业研究会	从烯烃制备环氧化物的改进催化方法
US8187159B2 (en)	2005-07-22	2012-05-29	Biocompatibles, UK	Therapeutic member including a rail used in brachytherapy and other radiation therapy
US7736293B2 (en) *	2005-07-22	2010-06-15	Biocompatibles Uk Limited	Implants for use in brachytherapy and other radiation therapy that resist migration and rotation
JP5176426B2 (ja) *	2007-03-16	2013-04-03	住友化学株式会社	シクロアルカノール及び／又はシクロアルカノンの製造方法
KR100987379B1 (ko) *	2008-01-07	2010-10-12	이도형	해양 오염 방지용 오일 방제선
KR200452158Y1 (ko) *	2008-04-18	2011-02-10	조병호	해상 오염 크리닝 장치
US8663210B2 (en)	2009-05-13	2014-03-04	Novian Health, Inc.	Methods and apparatus for performing interstitial laser therapy and interstitial brachytherapy
AU2010200556B2 (en) *	2010-02-15	2012-02-02	Oncobeta International Gmbh	Brachytherapy method of treating skin tumours using a tailor-made radioactive source
JP2012006887A (ja) *	2010-06-28	2012-01-12	Sumitomo Chemical Co Ltd	プロピレンオキサイドの製造方法
CN102757304B (zh) *	2011-04-29	2014-12-17	岳阳昌德化工实业有限公司	一种环己烷氧化的方法
CN102757306B (zh) *	2011-04-29	2015-01-28	岳阳昌德化工实业有限公司	一种环己酮的制备方法
CN102757303B (zh) *	2011-04-29	2014-12-17	岳阳昌德化工实业有限公司	一种环己烷氧化的方法
CN102757305B (zh) *	2011-04-29	2014-12-17	岳阳昌德化工实业有限公司	一种环己烷氧化的方法
CN102766031A (zh) *	2011-05-05	2012-11-07	岳阳昌德化工实业有限公司	一种环己烷氧化的方法
CN102766026B (zh) *	2011-05-05	2014-12-17	岳阳昌德化工实业有限公司	一种环己烷氧化制环己醇的方法
CN105712954A (zh) *	2014-12-05	2016-06-29	中国科学院大连化学物理研究所	一种1-辛烯环氧化制备1,2-环氧辛烷的方法
CN107552031B (zh) *	2016-07-01	2020-12-11	东联化学股份有限公司	含钛氧化硅材料的制备方法及应用
CN107262147B (zh) *	2017-06-14	2019-09-27	昆明理工大学	一种耐硫性催化燃烧催化剂及制备方法
CN116332200B (zh) *	2021-12-22	2025-09-05	中国石油化工股份有限公司	钛硅分子筛及其制备方法和制备环己酮肟的方法、制备己内酯的方法
WO2024011452A1 (fr) *	2022-07-13	2024-01-18	深圳先进技术研究院	Procédé de préparation d'un film mince et utilisation d'un film mince

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3351049A (en)	1965-04-12	1967-11-07	Hazleton Nuclear Science Corp	Therapeutic metal seed containing within a radioactive isotope disposed on a carrier and method of manufacture
US3640093A (en) *	1969-03-10	1972-02-08	Owens Illinois Inc	Process of converting metalorganic compounds and high purity products obtained therefrom
US3923843A (en) *	1972-03-13	1975-12-02	Shell Oil Co	Epoxidation process with improved heterogeneous catalyst
IT1127311B (it) *	1979-12-21	1986-05-21	Anic Spa	Materiale sintetico,cristallino,poroso costituito da ossidi di silicio e titanio,metodo per la sua preparazione e suoi usi
US4323055A (en) *	1980-04-08	1982-04-06	Minnesota Mining And Manufacturing Company	Radioactive iodine seed
US4510924A (en)	1980-07-10	1985-04-16	Yale-New Haven Hospital, Inc.	Brachytherapy devices and methods employing americium-241
IT1150699B (it) *	1982-03-19	1986-12-17	Anic Spa	Procedimento per la ossidrilazione di idrocarburi aromatici
US4697575A (en)	1984-11-21	1987-10-06	Henry Ford Hospital	Delivery system for interstitial radiation therapy including substantially non-deflecting elongated member
US4702228A (en)	1985-01-24	1987-10-27	Theragenics Corporation	X-ray-emitting interstitial implants
ES2033693T3 (es) *	1986-01-28	1993-04-01	Eniricerche S.P.A.	Un procedimiento para la exposidacion de compuestos olefinicos.
US4994013A (en) *	1988-07-28	1991-02-19	Best Industries, Inc.	Pellet for a radioactive seed
US5084002A (en)	1988-08-04	1992-01-28	Omnitron International, Inc.	Ultra-thin high dose iridium source for remote afterloader
GB8904177D0 (en)	1989-02-23	1989-04-05	Amersham Int Plc	Low energy radiation source and devices
US5405309A (en)	1993-04-28	1995-04-11	Theragenics Corporation	X-ray emitting interstitial implants
DE4419195A1 (de)	1993-07-12	1995-01-19	Degussa	Strukturierter Katalysator, bestehend aus mikroporösen Oxiden von Silicium, Aluminium und Titan
JP3658790B2 (ja) *	1995-03-30	2005-06-08	住友化学株式会社	触媒及びオキシラン化合物の製造方法
US5713828A (en) *	1995-11-27	1998-02-03	International Brachytherapy S.A	Hollow-tube brachytherapy device
DE19545042A1 (de) *	1995-12-02	1997-06-05	Studiengesellschaft Kohle Mbh	Amorphe mikroporöse Mischoxidkatalysatoren mit kontrollierter Oberflächenpolarität für die selektive heterogene Katalyse Adsorption und Stofftrennung
US5759945A (en) *	1997-03-26	1998-06-02	Arco Chemical Technology, L.P.	Preparation of titanium-containing catalysts using titanosiloxane polymers
JP2002502676A (ja) *	1998-02-12	2002-01-29	ロバート、ロバートソン	カプセル収容の低エネルギーブラキ治療線源
US5997463A (en) *	1998-03-26	1999-12-07	North American Scientific	Laser welded brachytherapy source and method of making the same
US6007475A (en) *	1998-08-12	1999-12-28	Cns Technology, Inc.	Radioactive therapeutic seeds
US6200258B1 (en) *	1999-08-10	2001-03-13	Syntheon, Llc	Radioactive therapeutic seed having selective marker configuration

1998
- 1998-11-12 JP JP2000521054A patent/JP2001523651A/ja active Pending
- 1998-11-12 HU HU0004411A patent/HUP0004411A3/hu unknown
- 1998-11-12 AU AU21970/99A patent/AU2197099A/en not_active Abandoned
- 1998-11-12 PL PL98340827A patent/PL340827A1/xx unknown
- 1998-11-12 BR BR9815311-0A patent/BR9815311A/pt not_active IP Right Cessation
- 1998-11-12 EE EEP200000234A patent/EE200000234A/xx unknown
- 1998-11-12 IL IL13612498A patent/IL136124A0/xx unknown
- 1998-11-12 SK SK675-2000A patent/SK6752000A3/sk unknown
- 1998-11-12 CN CN98811049A patent/CN1278808A/zh active Pending
- 1998-11-12 WO PCT/US1998/024180 patent/WO1999025666A2/fr not_active Ceased
- 1998-11-12 KR KR1020007005206A patent/KR20010032082A/ko not_active Withdrawn
- 1998-11-12 EP EP98965958A patent/EP1056683A2/fr not_active Withdrawn
- 1998-11-13 ZA ZA9810409A patent/ZA9810409B/xx unknown
- 1998-11-13 AR ARP980105785A patent/AR014027A1/es unknown
- 1998-11-13 US US09/191,672 patent/US6391279B1/en not_active Expired - Fee Related
- 1998-11-16 HR HR60/065,993A patent/HRP980595A2/hr not_active Application Discontinuation
2000
- 2000-05-09 NO NO20002406A patent/NO20002406D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
IL136124A0 (en)	2001-05-20
JP2001523651A (ja)	2001-11-27
PL340827A1 (en)	2001-02-26
HUP0004411A2 (hu)	2001-04-28
AR014027A1 (es)	2001-01-31
BR9815311A (pt)	2001-08-07
AU2197099A (en)	1999-06-07
NO20002406L (no)	2000-05-09
HUP0004411A3 (en)	2001-06-28
KR20010032082A (ko)	2001-04-16
EE200000234A (et)	2001-06-15
WO1999025666A3 (fr)	1999-09-10
WO1999025666A2 (fr)	1999-05-27
HRP980595A2 (en)	2000-02-29
CN1278808A (zh)	2001-01-03
ZA9810409B (en)	2000-05-15
US6391279B1 (en)	2002-05-21
NO20002406D0 (no)	2000-05-09
EP1056683A2 (fr)	2000-12-06

Publication	Publication Date	Title
SK6752000A3 (en)	2000-10-09	Process for the selective oxidation of organic compounds
EP0659685B1 (fr)	2002-03-27	Procédé d'époxydation et catalyseur à cet effet
KR970010334B1 (ko)	1997-06-25	규소, 알루미늄 및 티탄의 미세다공성 산화물로 이루어진 구조화된 촉매
US5262550A (en)	1993-11-16	Epoxidation process using titanium-rich silicalite catalysts
EP2595921A1 (fr)	2013-05-29	Titanosilicate mésoporeux ordonné et son procédé de préparation
HUP0200811A2 (en)	2002-06-29	Solid composition, its producing and using
US5081267A (en)	1992-01-14	Epoxidation process
KR19990087478A (ko)	1999-12-27	귀금속을 함유하지 않는 촉매 조성물
JP2000511912A (ja)	2000-09-12	ゼオライト酸化触媒を使用してオレフィンおよび過酸化水素またはヒドロペルオキシドからエポキシドを製造する方法
CA2370815A1 (fr)	2000-11-02	Matieres hybrides sol-gel contenant des metaux nobles utilisees comme catalyseurs pour l'oxydation partielle d'hydrocarbures
KR20020048431A (ko)	2002-06-22	산화물 및 그의 제조법
EP1044196A2 (fr)	2000-10-18	Procede d'oxydation selective de composes organiques
Dusi et al.	1999	Chemo-and diastereoselective epoxidation of allylic alcohols with a titania–silica aerogel
US6251851B1 (en)	2001-06-26	Process for the selective oxidation of organic compounds
Samantaray et al.	2005	Amine-modified titania–silica mixed oxides: 1. Effect of amine concentration and activation temperature towards epoxidation of cyclohexene
CZ20001646A3 (cs)	2000-09-13	Způsob selektivní oxidace organických sloučenin
JP2013523422A (ja)	2013-06-17	前処理されたエポキシ化触媒及びそれによりオレフィンを製造する方法
US20110288316A1 (en)	2011-11-24	Method for producing propylene oxide
MXPA00004647A (en)	2001-05-07	Process for the selective oxidation of organic compounds
EP3283468B1 (fr)	2020-09-30	Performances catalytiques améliorées dans l'époxydation de propylène
WO1998051811A1 (fr)	1998-11-19	Procede d'oxydation selective de composes organiques
Cheong et al.	2003	Preparation of titanium-containing carbon–silica composite catalysts and their liquid-phase epoxidation activity
JP2002320860A (ja)	2002-11-05	部分酸化触媒及びその製造方法
WO2003101977A1 (fr)	2003-12-11	Procede d'epoxydation utilisant un catalyseur d'oxyde de niobium sur support
HK1112900A (en)	2008-09-19	Method for producing olefin oxides and peroxides, reactor and the use thereof