JP2006509829A - フェノール、アセトン、α−メチルスチレン及び酸化プロピレンのコプロダクション及びその触媒 - Google Patents
フェノール、アセトン、α−メチルスチレン及び酸化プロピレンのコプロダクション及びその触媒 Download PDFInfo
- Publication number
- JP2006509829A JP2006509829A JP2004563715A JP2004563715A JP2006509829A JP 2006509829 A JP2006509829 A JP 2006509829A JP 2004563715 A JP2004563715 A JP 2004563715A JP 2004563715 A JP2004563715 A JP 2004563715A JP 2006509829 A JP2006509829 A JP 2006509829A
- Authority
- JP
- Japan
- Prior art keywords
- group
- catalyst
- metals
- cumene hydroperoxide
- acetone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 title claims abstract description 132
- 239000003054 catalyst Substances 0.000 title claims abstract description 112
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 71
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 23
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 title claims abstract description 22
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 title claims description 13
- 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 description 110
- 238000000034 method Methods 0.000 claims abstract description 77
- BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 claims abstract description 66
- 230000002378 acidificating effect Effects 0.000 claims abstract description 28
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 72
- 229910052751 metal Inorganic materials 0.000 claims description 52
- 239000002184 metal Substances 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 36
- 150000002739 metals Chemical class 0.000 claims description 35
- 238000005984 hydrogenation reaction Methods 0.000 claims description 30
- 239000003999 initiator Substances 0.000 claims description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 230000003647 oxidation Effects 0.000 claims description 19
- 238000007254 oxidation reaction Methods 0.000 claims description 19
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 19
- 229910044991 metal oxide Inorganic materials 0.000 claims description 16
- 150000004706 metal oxides Chemical class 0.000 claims description 16
- 239000011973 solid acid Substances 0.000 claims description 14
- 238000010790 dilution Methods 0.000 claims description 13
- 239000012895 dilution Substances 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 13
- 150000003254 radicals Chemical class 0.000 claims description 13
- 229910052723 transition metal Inorganic materials 0.000 claims description 13
- 150000003624 transition metals Chemical class 0.000 claims description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 238000006735 epoxidation reaction Methods 0.000 claims description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 12
- 239000010941 cobalt Substances 0.000 claims description 11
- 229910017052 cobalt Inorganic materials 0.000 claims description 11
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 11
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 10
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 10
- 239000000377 silicon dioxide Substances 0.000 claims description 10
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 10
- 239000003377 acid catalyst Substances 0.000 claims description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 8
- 239000002808 molecular sieve Substances 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000002638 heterogeneous catalyst Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 6
- 229910003455 mixed metal oxide Inorganic materials 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 6
- GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000004927 clay Substances 0.000 claims description 4
- 229910052570 clay Inorganic materials 0.000 claims description 4
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical group [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 4
- 229910000314 transition metal oxide Inorganic materials 0.000 claims description 4
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052750 molybdenum Inorganic materials 0.000 claims description 3
- 239000011733 molybdenum Substances 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 229910000420 cerium oxide Inorganic materials 0.000 claims 3
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims 3
- 238000003776 cleavage reaction Methods 0.000 abstract description 56
- 230000007017 scission Effects 0.000 abstract description 56
- 239000002253 acid Substances 0.000 abstract description 7
- 238000006297 dehydration reaction Methods 0.000 abstract description 4
- 230000018044 dehydration Effects 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 24
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 239000006227 byproduct Substances 0.000 description 16
- 239000000463 material Substances 0.000 description 11
- 238000006722 reduction reaction Methods 0.000 description 11
- 238000011084 recovery Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- -1 zirconium oxide Chemical class 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- 238000010828 elution Methods 0.000 description 5
- 238000010517 secondary reaction Methods 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 150000002432 hydroperoxides Chemical class 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- JESIHYIJKKUWIS-UHFFFAOYSA-N 1-(4-Methylphenyl)ethanol Chemical compound CC(O)C1=CC=C(C)C=C1 JESIHYIJKKUWIS-UHFFFAOYSA-N 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 241001147665 Foraminifera Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000011949 solid catalyst Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000588731 Hafnia Species 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 150000001298 alcohols 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 1
- QGUAJWGNOXCYJF-UHFFFAOYSA-N cobalt dinitrate hexahydrate Chemical compound O.O.O.O.O.O.[Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O QGUAJWGNOXCYJF-UHFFFAOYSA-N 0.000 description 1
- 229910001981 cobalt nitrate Inorganic materials 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- CJNBYAVZURUTKZ-UHFFFAOYSA-N hafnium(IV) oxide Inorganic materials O=[Hf]=O CJNBYAVZURUTKZ-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000013335 mesoporous material Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 1
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
- C07C409/10—Cumene hydroperoxide
-
- 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
- C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
-
- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/75—Cobalt
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/185—Phosphorus; Compounds thereof with iron group metals or platinum group metals
- B01J27/1853—Phosphorus; Compounds thereof with iron group metals or platinum group metals with iron, cobalt or nickel
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/03—Precipitation; Co-precipitation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
- C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/24—Chromium, molybdenum or tungsten
- C07C2523/28—Molybdenum
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
- C07C2527/053—Sulfates or other compounds comprising the anion (SnO3n+1)2-
- C07C2527/054—Sulfuric acid or other acids with the formula H2Sn03n+1
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/320,237 US6984761B2 (en) | 2002-12-16 | 2002-12-16 | Co-production of phenol, acetone, α-methylstyrene and propylene oxide, and catalyst therefor |
| PCT/US2003/040283 WO2004058672A1 (en) | 2002-12-16 | 2003-12-16 | Co-production of phenol, acetone, alpha-methylstyrene and propylene oxide, and catalyst therefor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006509829A true JP2006509829A (ja) | 2006-03-23 |
| JP2006509829A5 JP2006509829A5 (enExample) | 2007-02-08 |
Family
ID=32506828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004563715A Pending JP2006509829A (ja) | 2002-12-16 | 2003-12-16 | フェノール、アセトン、α−メチルスチレン及び酸化プロピレンのコプロダクション及びその触媒 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6984761B2 (enExample) |
| EP (1) | EP1575888B1 (enExample) |
| JP (1) | JP2006509829A (enExample) |
| KR (1) | KR101084379B1 (enExample) |
| CN (2) | CN1726176A (enExample) |
| AT (1) | ATE483674T1 (enExample) |
| AU (1) | AU2003297321A1 (enExample) |
| DE (1) | DE60334493D1 (enExample) |
| TW (1) | TWI310027B (enExample) |
| WO (1) | WO2004058672A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010517933A (ja) * | 2006-08-03 | 2010-05-27 | エクソンモービル・ケミカル・パテンツ・インク | アルキル芳香族化合物の酸化法 |
| JP2013535484A (ja) * | 2010-12-01 | 2013-09-12 | エルジー・ケム・リミテッド | αメチルスチレンの製造方法 |
| JP2014522381A (ja) * | 2011-07-15 | 2014-09-04 | エルジー・ケム・リミテッド | クミルアルコールの製造方法およびフェノール、アセトン、およびアルファメチルスチレンの製造方法 |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7455762B2 (en) * | 2004-08-31 | 2008-11-25 | Exxonmobil Research And Engineering Company | Selective hydrodesulfurization process |
| US7285512B2 (en) * | 2004-08-31 | 2007-10-23 | Exxonmobile Research And Engineering Company | Selective hydrodesulfurization catalyst |
| US8189615B2 (en) * | 2004-12-23 | 2012-05-29 | Nokia Corporation | Method and apparatus for communicating scheduling information from a UE to a radio access network |
| ES2261080B1 (es) * | 2005-04-19 | 2007-12-16 | Universidad Politecnica De Valencia | Procedimiento y catalizadores para la expoxidacion de compuestos olefinicos en presencia de oxigeno. |
| US7452841B2 (en) * | 2005-09-23 | 2008-11-18 | Eastman Chemical Company | Catalysts selective for the preparation of mixed ketones from a mixture of carboxylic acids |
| WO2007137020A2 (en) * | 2006-05-16 | 2007-11-29 | Shell Oil Company | Method for decomposing di(phenylalkyl)peroxides to produce hydroxybenzenes and phenylalkenes using solid catalysts |
| US7417003B2 (en) * | 2006-12-29 | 2008-08-26 | Uop Llc | Solid acid catalyst and process for decomposition of cumene hydroperoxide |
| US8680355B2 (en) * | 2008-12-01 | 2014-03-25 | Mitsui Chemcials, Inc. | Olefin production process |
| WO2010106966A1 (ja) * | 2009-03-16 | 2010-09-23 | 三井化学株式会社 | オレフィンの製造方法 |
| KR101403518B1 (ko) | 2010-12-21 | 2014-06-10 | 주식회사 엘지화학 | 알파 메틸 스티렌의 제조방법 |
| KR101476376B1 (ko) * | 2011-07-15 | 2014-12-26 | 주식회사 엘지화학 | 페놀, 아세톤 및 알파 메틸 스티렌의 제조방법 |
| KR101447255B1 (ko) * | 2011-07-22 | 2014-10-07 | 주식회사 엘지화학 | 페놀, 아세톤 및 알파 메틸 스티렌의 제조방법 |
| KR101431122B1 (ko) * | 2011-08-12 | 2014-08-19 | 주식회사 엘지화학 | 페놀, 아세톤 및 알파 메틸 스티렌의 제조방법 |
| KR101476375B1 (ko) * | 2011-09-02 | 2014-12-26 | 주식회사 엘지화학 | 페놀, 아세톤 및 알파 메틸 스티렌의 제조방법 |
| US9115105B2 (en) | 2011-09-30 | 2015-08-25 | Exxonmobil Chemical Patents Inc. | Production of propylene oxide |
| WO2017118887A1 (en) * | 2016-01-05 | 2017-07-13 | Sabic Global Technologies B.V. | Systems and methods for the co-production of hydrogen and alkylene oxides |
| CN112079691A (zh) * | 2020-09-17 | 2020-12-15 | 吉化集团油脂化工有限公司 | 提升苯酚产品质量的方法 |
| RU2750718C1 (ru) * | 2020-12-04 | 2021-07-01 | федеральное государственное бюджетное образовательное учреждение высшего образования "Казанский национальный исследовательский технологический университет" (ФГБОУ ВО "КНИТУ") | Способ разложения гидропероксида изопропилбензола с получением диметилфенилкарбинола |
| EP4043420B1 (en) | 2020-12-21 | 2024-10-09 | LG Chem, Ltd. | Method for producing alpha-methylstyrene |
Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2757209A (en) * | 1951-04-26 | 1956-07-31 | Allied Chem & Dye Corp | Recovery of phenol and alphamethylstyrene from cumene oxidation reaction mixtures |
| JPS5832831A (ja) * | 1981-06-22 | 1983-02-25 | アライド・コ−ポレ−シヨン | クメン酸化生成物の分解法 |
| JPS60174737A (ja) * | 1984-02-22 | 1985-09-09 | Mitsui Petrochem Ind Ltd | 芳香族アルコ−ルの製造法 |
| JPH01100136A (ja) * | 1987-10-13 | 1989-04-18 | Mitsubishi Petrochem Co Ltd | α−メチルスチレンの製造方法 |
| JPH02149534A (ja) * | 1988-11-30 | 1990-06-08 | Mitsui Petrochem Ind Ltd | クメンの製造方法 |
| JPH02231442A (ja) * | 1988-11-28 | 1990-09-13 | Mitsui Petrochem Ind Ltd | フェノールの製造方法 |
| JPH06192151A (ja) * | 1992-09-11 | 1994-07-12 | Aristech Chem Corp | クメンヒドロペルオキシドの二段階分解 |
| JPH0920699A (ja) * | 1995-07-07 | 1997-01-21 | Mitsui Petrochem Ind Ltd | フェノールの製造方法 |
| JP2001511787A (ja) * | 1997-02-11 | 2001-08-14 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ヒドロペルオキシドの分解法 |
| JP2002543052A (ja) * | 1999-04-22 | 2002-12-17 | モービル・オイル・コーポレイション | フェノールの製造 |
| JP2003506342A (ja) * | 1999-08-03 | 2003-02-18 | モービル・オイル・コーポレイション | フェノール及びアセトンの製造方法 |
| JP2003518047A (ja) * | 1999-12-21 | 2003-06-03 | エクソンモービル・オイル・コーポレイション | 反応性蒸留によるフェノールの製法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2854487A (en) * | 1955-04-12 | 1958-09-30 | Distillers Co Yeast Ltd | Process for the manufacture of carbinols |
| BE657838A (enExample) | 1964-01-07 | 1965-06-30 | ||
| US3403193A (en) * | 1965-06-28 | 1968-09-24 | Halcon International Inc | Process for the co-production of a styrene and a di-olefin |
| SU462812A1 (ru) * | 1972-03-28 | 1975-03-05 | Предприятие П/Я Р-6235 | Способ совместного получени фенола, ацетона и -метилстирола |
| JPS56140935A (en) | 1980-04-03 | 1981-11-04 | Sumitomo Chem Co Ltd | Preparation of styrene compound |
| JPS5916843A (ja) | 1982-07-20 | 1984-01-28 | Mitsui Toatsu Chem Inc | 芳香族アルコ−ルの連続製造法 |
| US4853197A (en) * | 1987-06-04 | 1989-08-01 | Uop | Crystalline metal aluminophosphates |
| RU1839668C (ru) * | 1988-11-28 | 1993-12-30 | МИЦУИ ПЕТРОКЕМИКАЛ ИНДАСТРИЗ, Лтд (JP) | Способ получени фенола |
| US5371305A (en) * | 1992-12-31 | 1994-12-06 | Hercules Incorporated | Process for producing phenol from cumene |
| US5463136A (en) * | 1994-12-22 | 1995-10-31 | Shell Oil Company | Cumene hydroperoxide cleavage process |
| WO1998027030A1 (en) | 1996-12-17 | 1998-06-25 | Alliedsignal Inc. | Process for the production of alpha methylstyrenes |
| DE69907148T2 (de) | 1998-02-17 | 2003-10-16 | Shell Internationale Research Maatschappij B.V., Den Haag | Verfahren zur herstellung von styrolen |
| US5905178A (en) * | 1998-04-20 | 1999-05-18 | Catalytic Distillation Technologies | Removal of α-methyl styrene from cumene |
| US5932751A (en) * | 1998-06-23 | 1999-08-03 | Arco Chemical Technology, L.P. | Epoxidation catalyst and process |
| US6169215B1 (en) * | 1999-03-25 | 2001-01-02 | Mobil Oil Corporation | Production of phenol |
| US6114551A (en) * | 1999-10-04 | 2000-09-05 | Mobil Oil Corporation | Olefin epoxidation catalysts |
-
2002
- 2002-12-16 US US10/320,237 patent/US6984761B2/en not_active Expired - Fee Related
-
2003
- 2003-12-16 CN CNA2003801061712A patent/CN1726176A/zh active Pending
- 2003-12-16 CN CN2010105394660A patent/CN102060653A/zh active Pending
- 2003-12-16 TW TW092135625A patent/TWI310027B/zh not_active IP Right Cessation
- 2003-12-16 AU AU2003297321A patent/AU2003297321A1/en not_active Abandoned
- 2003-12-16 JP JP2004563715A patent/JP2006509829A/ja active Pending
- 2003-12-16 DE DE60334493T patent/DE60334493D1/de not_active Expired - Lifetime
- 2003-12-16 AT AT03814132T patent/ATE483674T1/de not_active IP Right Cessation
- 2003-12-16 KR KR1020057010980A patent/KR101084379B1/ko not_active Expired - Fee Related
- 2003-12-16 WO PCT/US2003/040283 patent/WO2004058672A1/en not_active Ceased
- 2003-12-16 EP EP03814132A patent/EP1575888B1/en not_active Expired - Lifetime
Patent Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2757209A (en) * | 1951-04-26 | 1956-07-31 | Allied Chem & Dye Corp | Recovery of phenol and alphamethylstyrene from cumene oxidation reaction mixtures |
| JPS5832831A (ja) * | 1981-06-22 | 1983-02-25 | アライド・コ−ポレ−シヨン | クメン酸化生成物の分解法 |
| JPS60174737A (ja) * | 1984-02-22 | 1985-09-09 | Mitsui Petrochem Ind Ltd | 芳香族アルコ−ルの製造法 |
| JPH01100136A (ja) * | 1987-10-13 | 1989-04-18 | Mitsubishi Petrochem Co Ltd | α−メチルスチレンの製造方法 |
| JPH02231442A (ja) * | 1988-11-28 | 1990-09-13 | Mitsui Petrochem Ind Ltd | フェノールの製造方法 |
| JPH02149534A (ja) * | 1988-11-30 | 1990-06-08 | Mitsui Petrochem Ind Ltd | クメンの製造方法 |
| JPH02172927A (ja) * | 1988-12-26 | 1990-07-04 | Mitsui Petrochem Ind Ltd | クメンの製造方法 |
| JPH06192151A (ja) * | 1992-09-11 | 1994-07-12 | Aristech Chem Corp | クメンヒドロペルオキシドの二段階分解 |
| JPH0920699A (ja) * | 1995-07-07 | 1997-01-21 | Mitsui Petrochem Ind Ltd | フェノールの製造方法 |
| JP2001511787A (ja) * | 1997-02-11 | 2001-08-14 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ヒドロペルオキシドの分解法 |
| JP2002543052A (ja) * | 1999-04-22 | 2002-12-17 | モービル・オイル・コーポレイション | フェノールの製造 |
| JP2003506342A (ja) * | 1999-08-03 | 2003-02-18 | モービル・オイル・コーポレイション | フェノール及びアセトンの製造方法 |
| JP2003518047A (ja) * | 1999-12-21 | 2003-06-03 | エクソンモービル・オイル・コーポレイション | 反応性蒸留によるフェノールの製法 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010517933A (ja) * | 2006-08-03 | 2010-05-27 | エクソンモービル・ケミカル・パテンツ・インク | アルキル芳香族化合物の酸化法 |
| JP2013535484A (ja) * | 2010-12-01 | 2013-09-12 | エルジー・ケム・リミテッド | αメチルスチレンの製造方法 |
| JP2014522381A (ja) * | 2011-07-15 | 2014-09-04 | エルジー・ケム・リミテッド | クミルアルコールの製造方法およびフェノール、アセトン、およびアルファメチルスチレンの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE483674T1 (de) | 2010-10-15 |
| CN102060653A (zh) | 2011-05-18 |
| CN1726176A (zh) | 2006-01-25 |
| US6984761B2 (en) | 2006-01-10 |
| TW200508186A (en) | 2005-03-01 |
| EP1575888B1 (en) | 2010-10-06 |
| EP1575888A1 (en) | 2005-09-21 |
| KR101084379B1 (ko) | 2011-11-18 |
| AU2003297321A1 (en) | 2004-07-22 |
| DE60334493D1 (de) | 2010-11-18 |
| WO2004058672A1 (en) | 2004-07-15 |
| KR20050088178A (ko) | 2005-09-02 |
| US20040116749A1 (en) | 2004-06-17 |
| TWI310027B (en) | 2009-05-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2006509829A (ja) | フェノール、アセトン、α−メチルスチレン及び酸化プロピレンのコプロダクション及びその触媒 | |
| AU2002217114B2 (en) | Process for preparing oxirane compounds | |
| JP2951510B2 (ja) | クメンヒドロペルオキシドの二段階分解 | |
| KR20090123949A (ko) | 프로필렌 옥사이드의 제조 방법 | |
| JP2774607B2 (ja) | フェノールの製造方法およびその製造時の副生アセトンからプロピレンを得る方法 | |
| JP2005097206A (ja) | プロピレンオキサイドの製造方法 | |
| JP4385700B2 (ja) | プロピレンオキサイドの製造方法 | |
| JP2003081953A (ja) | プロピレンオキサイドの製造方法 | |
| JP2005097185A (ja) | プロピレンオキサイドの製造方法 | |
| JP2005097184A (ja) | プロピレンオキサイドの製造方法 | |
| JP2005097208A (ja) | プロピレンオキサイドの製造方法 | |
| CN116848076A (zh) | 丙烯的制造方法 | |
| JP2005097175A (ja) | プロピレンオキサイドの製造方法 | |
| JP2025188234A (ja) | プロピレンの製造方法 | |
| JP2005097183A (ja) | プロピレンオキサイドの製造方法 | |
| JP2005097210A (ja) | クメンの製造方法 | |
| JP2017533208A (ja) | 連結した反応器−蒸留系を用いた酸化エステル化反応からのその場での水の除去のための方法 | |
| WO2005030743A1 (ja) | プロピレンオキサイドの製造方法 | |
| JP2005097174A (ja) | プロピレンオキサイドの製造方法 | |
| JP2005097209A (ja) | プロピレンオキサイドの製造方法 | |
| JP2005097212A (ja) | プロピレンオキサイドの製造方法 | |
| JP2005097178A (ja) | プロピレンオキサイドの製造方法 | |
| JP2005097214A (ja) | プロピレンオキサイドの製造方法 | |
| JP2005097211A (ja) | プロピレンオキサイドの製造方法 | |
| JP2004292336A (ja) | クメンの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20061215 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20061215 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20100129 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100223 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20100518 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20100525 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100618 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20110517 |
|
| RD13 | Notification of appointment of power of sub attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7433 Effective date: 20110602 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20110602 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110915 |
|
| A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20110928 |
|
| RD13 | Notification of appointment of power of sub attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7433 Effective date: 20130228 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20130228 |