DK171933B1 - Fremgangsmåde til hydroxylering af aromatiske carbonhydrider eller derivater heraf. - Google Patents
Fremgangsmåde til hydroxylering af aromatiske carbonhydrider eller derivater heraf. Download PDFInfo
- Publication number
- DK171933B1 DK171933B1 DK123783A DK123783A DK171933B1 DK 171933 B1 DK171933 B1 DK 171933B1 DK 123783 A DK123783 A DK 123783A DK 123783 A DK123783 A DK 123783A DK 171933 B1 DK171933 B1 DK 171933B1
- Authority
- DK
- Denmark
- Prior art keywords
- phenol
- pitch
- selectivity
- hydroxylation
- yield
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 230000008569 process Effects 0.000 title claims description 13
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title claims description 7
- 230000033444 hydroxylation Effects 0.000 title claims description 6
- 238000005805 hydroxylation reaction Methods 0.000 title claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 29
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 29
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 21
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 20
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical class O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- 229960001413 acetanilide Drugs 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 150000003738 xylenes Chemical class 0.000 claims description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 21
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 16
- 229940022682 acetone Drugs 0.000 description 9
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920002994 synthetic fiber Polymers 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229910008484 TiSi Inorganic materials 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910002026 crystalline silica Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000853 cresyl group Chemical class C1(=CC=C(C=C1)C)* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- -1 mesethylene Chemical compound 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20262/82A IT1150699B (it) | 1982-03-19 | 1982-03-19 | Procedimento per la ossidrilazione di idrocarburi aromatici |
| IT2026282 | 1982-03-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK123783D0 DK123783D0 (da) | 1983-03-17 |
| DK123783A DK123783A (da) | 1983-09-20 |
| DK171933B1 true DK171933B1 (da) | 1997-08-18 |
Family
ID=11165238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK123783A DK171933B1 (da) | 1982-03-19 | 1983-03-17 | Fremgangsmåde til hydroxylering af aromatiske carbonhydrider eller derivater heraf. |
Country Status (10)
| Country | Link |
|---|---|
| BE (1) | BE896225A (enrdf_load_stackoverflow) |
| CH (1) | CH652114A5 (enrdf_load_stackoverflow) |
| DE (1) | DE3309669A1 (enrdf_load_stackoverflow) |
| DK (1) | DK171933B1 (enrdf_load_stackoverflow) |
| FR (1) | FR2523575B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2116974B (enrdf_load_stackoverflow) |
| IT (1) | IT1150699B (enrdf_load_stackoverflow) |
| NL (1) | NL192876C (enrdf_load_stackoverflow) |
| NO (1) | NO156648C (enrdf_load_stackoverflow) |
| SE (1) | SE461730B (enrdf_load_stackoverflow) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2618143B1 (fr) * | 1987-07-17 | 1989-09-22 | Rhone Poulenc Chimie | Procede d'hydroxylation du phenol |
| FR2622574B1 (fr) * | 1987-10-29 | 1990-02-23 | Rhone Poulenc Chimie | Procede d'hydroxylation de phenols et d'ethers de phenols |
| US5254746A (en) * | 1987-10-29 | 1993-10-19 | Rhone-Poulenc Chimie | Hydroxylation of phenols/phenol ethers |
| FR2622575B1 (fr) * | 1987-10-29 | 1990-02-23 | Rhone Poulenc Chimie | Procede d'hydroxylation de phenols et d'ethers de phenols |
| FR2643633B1 (fr) * | 1989-02-28 | 1991-05-10 | Rhone Poulenc Chimie | Procede d'hydroxylation de phenols et d'ethers de phenols |
| FR2666333B1 (fr) * | 1990-08-31 | 1994-04-08 | Rhone Poulenc Chimie | Procede d'hydroxylation de phenols et d'ethers de phenols. |
| EP0466545A1 (fr) * | 1990-06-29 | 1992-01-15 | Rhone-Poulenc Chimie | Zéolithes à base de silice et d'oxydes d'éléments tétravalents, leur procédé de synthèse et leur application |
| EP0473509A3 (fr) * | 1990-08-29 | 1992-03-18 | Rhone-Poulenc Chimie | Procédé de préparation de zéolithes à base de silice et éventuellement d'oxydes d'éléments tétravalents |
| DE4138155A1 (de) | 1991-11-21 | 1993-05-27 | Basf Ag | Verfahren zur herstellung von im wesentlichen alkalifreien titansilikat-kristallen mit zeolithstruktur |
| US5426244A (en) * | 1991-12-20 | 1995-06-20 | Mitsubishi Gas Chemical Company, Inc. | Method for preparing dihydric phenols |
| DE4214174A1 (de) * | 1992-04-30 | 1993-11-04 | Basf Ag | Verfahren zur herstellung von n-hydroxyazolen |
| FR2693457B1 (fr) * | 1992-07-10 | 1994-09-02 | Rhone Poulenc Chimie | Procédé d'hydroxylation de composés phénoliques. |
| US5233097A (en) * | 1992-10-15 | 1993-08-03 | Uop | Oxidation of aromatics to hydroxyaromatics using aluminosilicates containing framework titanium |
| ATE143831T1 (de) * | 1992-12-03 | 1996-10-15 | Kataleuna Gmbh Catalysts | Oxidationskatalysatoren |
| DE4419195A1 (de) * | 1993-07-12 | 1995-01-19 | Degussa | Strukturierter Katalysator, bestehend aus mikroporösen Oxiden von Silicium, Aluminium und Titan |
| RU2074164C1 (ru) * | 1994-04-12 | 1997-02-27 | Институт катализа им.Г.К.Борескова СО РАН | Способ получения фенола или его производных |
| RU2058286C1 (ru) * | 1994-04-12 | 1996-04-20 | Институт катализа им.Г.К.Борескова СО РАН | Способ получения фенола или его производных |
| US5712402A (en) * | 1994-08-22 | 1998-01-27 | Board Of Trustees Operating Michigan State University | Catalytic applications of mesoporous metallosilicate molecular sieves and methods for their preparation |
| DE19607577A1 (de) * | 1996-02-29 | 1997-09-04 | Basf Ag | Netzkatalysator auf Basis von Titan- oder Vanadiumzeolithen und inerten Netzgeweben zur Beschleunigung von Oxidationsreaktionen |
| US5874646A (en) * | 1996-08-07 | 1999-02-23 | Solutia Inc. | Preparation of phenol or phenol derivatives |
| US5892132A (en) * | 1996-08-08 | 1999-04-06 | Solutia Inc. | Transport hydroxylation reactor |
| US5808167A (en) * | 1996-08-20 | 1998-09-15 | Solutia Inc. | Selective introduction of active sites for hydroxylation of benzene |
| US5874647A (en) * | 1996-08-20 | 1999-02-23 | Solutia Inc. | Benzene hydroxylation catalyst stability by acid treatment |
| KR100544044B1 (ko) | 1996-10-07 | 2006-01-23 | 솔루티아인코포레이티드 | 방향족 화합물 및 벤젠의 하이드록실화 방법 및 이를 위한 반응 혼합물 |
| US6156938A (en) * | 1997-04-03 | 2000-12-05 | Solutia, Inc. | Process for making phenol or phenol derivatives |
| WO1999025666A2 (en) * | 1997-11-14 | 1999-05-27 | Du Pont Pharmaceuticals Company | Process for the selective oxidation of organic compounds |
| EP1044196A2 (en) * | 1997-11-24 | 2000-10-18 | E.I. Du Pont De Nemours And Company | Process for the selective oxidation of organic compounds |
| IT1296573B1 (it) * | 1997-11-27 | 1999-07-14 | Enichem Spa | Procedimento per l'ossidazione di composti aromatici a idrossiaromatici |
| DE19939416A1 (de) | 1999-08-20 | 2001-02-22 | Basf Ag | Verfahren zur Herstellung eines kristallinen, zeolithischen Feststoffs |
| US6437197B1 (en) | 2000-04-27 | 2002-08-20 | Shell Oil Company | Process for catalytic hydroxylation of aromatic hydrocarbons |
| JP2005060384A (ja) * | 2003-07-30 | 2005-03-10 | Ube Ind Ltd | フェノール化合物の製造方法 |
| WO2005063664A1 (en) * | 2003-12-31 | 2005-07-14 | Council Of Scientific & Industrial Research | Process for conversion of phenol to hydroquinone and quinones |
| WO2006089193A2 (en) | 2005-02-17 | 2006-08-24 | Monsanto Technology Llc | Transition metal-containing catalysts and catalyst combinations including transition metal-containing catalysts and processes for their preparation and use as oxidation catalysts |
| FR2987046B1 (fr) | 2012-02-17 | 2014-03-21 | Rhodia Operations | Procede d'hydroxylation de composes aromatiques, catalyseur d'hydroxylation et son procede de preparation |
| TWI471299B (zh) * | 2012-10-04 | 2015-02-01 | China Petrochemical Dev Corp Taipei Taiwan | Hydroxylation of phenol |
| CN105523898B (zh) * | 2014-09-29 | 2019-03-22 | 中国石油化工股份有限公司 | 一种氧化苯酚的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1448358A (en) * | 1974-04-04 | 1976-09-08 | Ube Industries | Process for preparint dihydric phenol derivatives |
| US4013727A (en) * | 1974-11-07 | 1977-03-22 | Ube Industries, Ltd. | Process for preparing hydroxyphenyl ethers |
| IT1195029B (it) * | 1980-09-09 | 1988-09-28 | Anic Spa | Procedimento per la ossidrilazione di idrocarburi aromatici |
-
1982
- 1982-03-19 IT IT20262/82A patent/IT1150699B/it active
-
1983
- 1983-03-16 CH CH1454/83A patent/CH652114A5/it not_active IP Right Cessation
- 1983-03-16 GB GB08307296A patent/GB2116974B/en not_active Expired
- 1983-03-16 NO NO830926A patent/NO156648C/no not_active IP Right Cessation
- 1983-03-17 DE DE19833309669 patent/DE3309669A1/de active Granted
- 1983-03-17 NL NL8300962A patent/NL192876C/nl not_active IP Right Cessation
- 1983-03-17 DK DK123783A patent/DK171933B1/da not_active IP Right Cessation
- 1983-03-18 SE SE8301492A patent/SE461730B/sv not_active IP Right Cessation
- 1983-03-18 FR FR8304502A patent/FR2523575B1/fr not_active Expired
- 1983-03-21 BE BE0/210368A patent/BE896225A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO156648C (no) | 1987-10-28 |
| FR2523575B1 (fr) | 1986-10-10 |
| SE461730B (sv) | 1990-03-19 |
| NO156648B (no) | 1987-07-20 |
| CH652114A5 (it) | 1985-10-31 |
| NL8300962A (nl) | 1983-10-17 |
| DE3309669C2 (enrdf_load_stackoverflow) | 1990-10-25 |
| FR2523575A1 (fr) | 1983-09-23 |
| NL192876C (nl) | 1998-04-02 |
| SE8301492D0 (sv) | 1983-03-18 |
| DK123783D0 (da) | 1983-03-17 |
| GB2116974B (en) | 1985-10-02 |
| NL192876B (nl) | 1997-12-01 |
| IT1150699B (it) | 1986-12-17 |
| SE8301492L (sv) | 1983-09-20 |
| IT8220262A0 (it) | 1982-03-19 |
| DK123783A (da) | 1983-09-20 |
| GB2116974A (en) | 1983-10-05 |
| GB8307296D0 (en) | 1983-04-20 |
| NO830926L (no) | 1983-09-20 |
| BE896225A (fr) | 1983-09-21 |
| DE3309669A1 (de) | 1983-09-29 |
| IT8220262A1 (it) | 1983-09-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK171933B1 (da) | Fremgangsmåde til hydroxylering af aromatiske carbonhydrider eller derivater heraf. | |
| DE3135559C2 (de) | Verfahren zur Herstellung phenolischer Verbindungen | |
| JP3049086B2 (ja) | 飽和炭化水素鎖の酸化 | |
| US6042807A (en) | Tellurium-containing molecular sieves | |
| US5233097A (en) | Oxidation of aromatics to hydroxyaromatics using aluminosilicates containing framework titanium | |
| Rao et al. | Catalytic hydroxylation of phenol over a vanadium silicate molecular sieve with MEL structure | |
| US6300506B1 (en) | Process for the preparation of epoxites | |
| US5648562A (en) | Oxidation process | |
| CA2048772A1 (en) | One step synthesis of methyl t-butyl ether from t-butanol using fluorosulfonic acid-modified zeolite catalysts | |
| US6133487A (en) | Process for the oxidation of aromatic compounds to hydroxyaromatic compounds | |
| EP1072599B1 (en) | Process for the preparation of olefin oxides | |
| RU2340591C2 (ru) | Объединенный способ получения фенола из бензола с рециклом побочных продуктов | |
| US6872859B2 (en) | Process for the preparation of bisphenols with zeolites | |
| EP0232742B1 (en) | Method for the preparation of ketones | |
| JP7560279B2 (ja) | ヒドロキシ酸の製造方法。 | |
| JP3010793B2 (ja) | 置換芳香族化合物の酸化方法 | |
| CA1199940A (en) | Ethylbenzene production employing tea-silicate catalysts | |
| JPH1129506A (ja) | ジアリールメタンまたはその誘導体の製造方法 | |
| US5639922A (en) | Process for treatment of hydroperoxide mixture | |
| KR101385020B1 (ko) | 파라벤조퀴논 및 카테콜 제조용 불균일 촉매 및 상기 촉매를 사용한 제조 방법 | |
| TW200407289A (en) | Process for the preparation of hydroxylated aromatic compounds | |
| JP4269111B2 (ja) | 脂環式エーテルの製造方法 | |
| Yashima et al. | Hydroxylation of toluene with hydrogen peroxide on HY zeolites with various Si/Al ratios | |
| JP2002105011A (ja) | 芳香族ジヒドロキシ化合物の製造方法 | |
| JPS6270332A (ja) | ２，６−ジヒドロキシナフタレンの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| PUP | Patent expired |