DE60001246T2 - Hydroxylierungskatalysator und Verfahren für die Herstellung von hydroxyaromatische Verbindungen - Google Patents
Hydroxylierungskatalysator und Verfahren für die Herstellung von hydroxyaromatische VerbindungenInfo
- Publication number
- DE60001246T2 DE60001246T2 DE60001246T DE60001246T DE60001246T2 DE 60001246 T2 DE60001246 T2 DE 60001246T2 DE 60001246 T DE60001246 T DE 60001246T DE 60001246 T DE60001246 T DE 60001246T DE 60001246 T2 DE60001246 T2 DE 60001246T2
- Authority
- DE
- Germany
- Prior art keywords
- compound
- crystalline titanium
- reaction
- titanium silicate
- catalyst
- 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.)
- Expired - Lifetime
Links
- -1 hydroxy aromatic compounds Chemical class 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 31
- 239000003054 catalyst Substances 0.000 title claims description 28
- 238000005805 hydroxylation reaction Methods 0.000 title description 6
- 230000033444 hydroxylation Effects 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 4
- 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 claims description 37
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 18
- 125000005375 organosiloxane group Chemical group 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000005224 alkoxybenzenes Chemical class 0.000 claims description 5
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 28
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 13
- 150000001491 aromatic compounds Chemical class 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- 239000010936 titanium Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229910052719 titanium Inorganic materials 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000000640 hydroxylating effect Effects 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 150000004292 cyclic ethers Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 3
- BXJGUBZTZWCMEX-UHFFFAOYSA-N 2,3-dimethylbenzene-1,4-diol Chemical compound CC1=C(C)C(O)=CC=C1O BXJGUBZTZWCMEX-UHFFFAOYSA-N 0.000 description 2
- PGSWEKYNAOWQDF-UHFFFAOYSA-N 3-methylcatechol Chemical compound CC1=CC=CC(O)=C1O PGSWEKYNAOWQDF-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 238000010420 art technique Methods 0.000 description 2
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- 238000001027 hydrothermal synthesis Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical class CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- CKJAETQXQRJXLM-UHFFFAOYSA-N 1,4-dimethylcyclohexa-2,5-diene-1,4-diol Chemical compound CC1(O)C=CC(C)(O)C=C1 CKJAETQXQRJXLM-UHFFFAOYSA-N 0.000 description 1
- WGCUZUDACXOATC-UHFFFAOYSA-N 1,4-dimethylcyclohexa-3,5-diene-1,2-diol Chemical compound CC1=CC(O)C(C)(O)C=C1 WGCUZUDACXOATC-UHFFFAOYSA-N 0.000 description 1
- WASRVAMMCHZMDA-UHFFFAOYSA-N 1,6-dimethylcyclohexa-3,5-diene-1,2-diol Chemical compound CC1=CC=CC(O)C1(C)O WASRVAMMCHZMDA-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- YGLVLWAMIJMBPF-UHFFFAOYSA-N 3,5-dimethylbenzene-1,2-diol Chemical compound CC1=CC(C)=C(O)C(O)=C1 YGLVLWAMIJMBPF-UHFFFAOYSA-N 0.000 description 1
- ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 description 1
- QEYQMWSESURNPP-UHFFFAOYSA-N 4-propan-2-yloxyphenol Chemical compound CC(C)OC1=CC=C(O)C=C1 QEYQMWSESURNPP-UHFFFAOYSA-N 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- 229910018557 Si O Inorganic materials 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- ZYNMJJNWXVKJJV-UHFFFAOYSA-N propan-2-yloxybenzene Chemical compound CC(C)OC1=CC=CC=C1 ZYNMJJNWXVKJJV-UHFFFAOYSA-N 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RCYJPSGNXVLIBO-UHFFFAOYSA-N sulfanylidenetitanium Chemical compound [S].[Ti] RCYJPSGNXVLIBO-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of other oxidants than molecular oxygen or their mixtures with molecular oxygen
-
- 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
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/123—Organometallic polymers, e.g. comprising C-Si bonds in the main chain or in subunits grafted to the main chain
- B01J31/124—Silicones or siloxanes or comprising such units
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12164799 | 1999-04-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60001246D1 DE60001246D1 (de) | 2003-02-27 |
| DE60001246T2 true DE60001246T2 (de) | 2003-09-04 |
Family
ID=14816438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60001246T Expired - Lifetime DE60001246T2 (de) | 1999-04-28 | 2000-04-28 | Hydroxylierungskatalysator und Verfahren für die Herstellung von hydroxyaromatische Verbindungen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6479711B1 (enExample) |
| EP (1) | EP1048639B1 (enExample) |
| KR (1) | KR20000071797A (enExample) |
| DE (1) | DE60001246T2 (enExample) |
| IN (1) | IN187869B (enExample) |
| SG (1) | SG87107A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19954322A1 (de) * | 1999-11-10 | 2001-05-17 | Basf Ag | Oxid und Verfahren zu dessen Herstellung |
| WO2003074179A1 (en) * | 2002-03-04 | 2003-09-12 | Sumitomo Chemical Company, Limited | Method for improving crystalline titanosilicate catalyst having mww structure |
| US7148386B2 (en) | 2004-07-30 | 2006-12-12 | General Electric Company | Processes for preparing benzoquinones and hydroquinones |
| JP2010159245A (ja) * | 2008-09-19 | 2010-07-22 | Sumitomo Chemical Co Ltd | 酸化化合物の製造方法 |
| US11654426B2 (en) | 2018-05-21 | 2023-05-23 | Mitsui Chemicals, Inc. | Method for manufacturing modified aluminosilicate, modified aluminosilicate, and method for manufacturing aromatic dihydroxy compound using the same |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP0230949B1 (en) * | 1986-01-28 | 1992-07-22 | ENIRICERCHE S.p.A. | A process for the epoxydation of olefinic compounds |
| US5254746A (en) | 1987-10-29 | 1993-10-19 | Rhone-Poulenc Chimie | Hydroxylation of phenols/phenol ethers |
| JPH02298350A (ja) | 1989-05-15 | 1990-12-10 | Tosoh Corp | 芳香族化合物のヒドロキシル化反応用触媒 |
| FR2655332A1 (fr) | 1989-12-05 | 1991-06-07 | Rhone Poulenc Chimie | Procede d'hydroxylation de phenols et d'ethers de phenols. |
| JP2866715B2 (ja) | 1990-07-04 | 1999-03-08 | 三井化学株式会社 | 芳香族ヒドロキシ化合物の製造法 |
| US5426244A (en) | 1991-12-20 | 1995-06-20 | Mitsubishi Gas Chemical Company, Inc. | Method for preparing dihydric phenols |
| US5262550A (en) * | 1992-04-30 | 1993-11-16 | Arco Chemical Technology, L.P. | Epoxidation process using titanium-rich silicalite catalysts |
| JPH072714A (ja) | 1993-06-16 | 1995-01-06 | Mitsubishi Gas Chem Co Inc | 二価フェノール類の製造方法 |
| DE69426907T2 (de) | 1993-08-11 | 2001-09-27 | Mitsubishi Gas Chemical Co., Inc. | Titanosilikate Katalysatorteilchen |
| FR2730722B1 (fr) * | 1995-02-17 | 1997-04-30 | Rhone Poulenc Chimie | Zeolithe ti-beta a haute teneur en silice, son procede de preparation et son utilisation comme catalyseur d'oxydation |
| IT1293496B1 (it) * | 1997-07-29 | 1999-03-01 | Enichem Spa | Procedimento per la sintesi di fenolo da benzene |
-
2000
- 2000-04-24 KR KR1020000021610A patent/KR20000071797A/ko not_active Abandoned
- 2000-04-26 IN IN248CA2000 patent/IN187869B/en unknown
- 2000-04-27 SG SG200002295A patent/SG87107A1/en unknown
- 2000-04-28 DE DE60001246T patent/DE60001246T2/de not_active Expired - Lifetime
- 2000-04-28 EP EP00303590A patent/EP1048639B1/en not_active Expired - Lifetime
- 2000-04-28 US US09/559,069 patent/US6479711B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE60001246D1 (de) | 2003-02-27 |
| EP1048639B1 (en) | 2003-01-22 |
| IN187869B (enExample) | 2002-07-13 |
| US6479711B1 (en) | 2002-11-12 |
| SG87107A1 (en) | 2002-03-19 |
| KR20000071797A (ko) | 2000-11-25 |
| EP1048639A1 (en) | 2000-11-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2425681A1 (de) | Alkylaether von polyglyzerin und deren herstellung | |
| DE3135559A1 (de) | Verfahren zur hydroxylierung von aromatischen kohlenwasserstoffen | |
| EP0102508A1 (de) | Verfahren zur Reinigung von rohen Polyether-Polyolen | |
| WO1994009024A1 (de) | Verfahren zum alkylieren von östronderivaten | |
| DE60003264T2 (de) | Verfahren zur herstellung von glycerylethern | |
| DE69929415T2 (de) | Verfahren zur kontinuierlichen Herstellung von Propylenoxid und weiteren Alkenoxiden | |
| DE19524245C1 (de) | Verfahren zur Herstellung von Guerbetalkoholen | |
| DE60001246T2 (de) | Hydroxylierungskatalysator und Verfahren für die Herstellung von hydroxyaromatische Verbindungen | |
| DE2804063C3 (de) | Verfahren zur Herstellung von Protocatechualdehyd oder 3-Methoxy- bzw. Äthoxy-4-hydroxybenzaldehyd | |
| EP0915890A1 (de) | Verfahren zur herstellung von alkoxysilanen | |
| DE69214227T2 (de) | Verfahren zur Herstellung von Polyphenylsilsesquioxanen | |
| EP1541541B1 (de) | Verfahren zur Herstellung alkoxyreiner Erdalkalialkoxide | |
| EP0772602A2 (de) | Verfahren zur herstellung 1,3-disubstituierter imidazolidinone | |
| DE2548384C3 (de) | Verfahren zur Herstellung von Hydroxyphenyläthern | |
| EP0394984B1 (de) | Verfahren zur Reinigung von Alkylenoxid-Addukten | |
| DE60104789T2 (de) | Verfahren zur Herstellung von 2,4,5-Trialkylbenzaldehyden | |
| DE60011673T2 (de) | Verfahren zur herstellung von dl-alpha-tocopherol mit hoher ausbeute und hoher reinheit | |
| DE3107518A1 (de) | Verfahren zur herstellung von estern und aethern der glykolsaeure | |
| DE2628778A1 (de) | Verfahren zur herstellung von mono- oder polyglykolaethern | |
| DE69926495T2 (de) | VERFAHREN ZUR HERSTELLUNG VON ε-CAPROLACTAM | |
| DE3335186C2 (de) | Verfahren zur Herstellung von Dinitrophenylethern | |
| EP0516017A2 (de) | Verfahren zur Herstellung von Alkoxylaten mit enger Homologenverteilung unter Verwendung von Antimonpentahalogenid-Komplexen als Katalysator | |
| DE3883353T2 (de) | Verfahren zur herstellung von dihydroxynaphthalen. | |
| DE3128962A1 (de) | "verfahren zur herstellung von alkylenglykoldiethern | |
| DE2922688A1 (de) | Nitrosierungsverfahren |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |