SE461730B - Foerfarande foer hydoxylering av aromatiska kolvaeten - Google Patents
Foerfarande foer hydoxylering av aromatiska kolvaetenInfo
- Publication number
- SE461730B SE461730B SE8301492A SE8301492A SE461730B SE 461730 B SE461730 B SE 461730B SE 8301492 A SE8301492 A SE 8301492A SE 8301492 A SE8301492 A SE 8301492A SE 461730 B SE461730 B SE 461730B
- Authority
- SE
- Sweden
- Prior art keywords
- phenol
- tar
- selectivity
- reaction
- anisole
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 34
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 3
- 230000033444 hydroxylation Effects 0.000 claims description 3
- 238000005805 hydroxylation reaction Methods 0.000 claims description 3
- 229960001413 acetanilide Drugs 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 229910052790 beryllium Inorganic materials 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 229910021536 Zeolite Inorganic materials 0.000 claims 1
- 239000010457 zeolite Substances 0.000 claims 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 9
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- 229920002994 synthetic fiber Polymers 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- 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
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 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
- 208000006558 Dental Calculus Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- 241001406423 Leucaena pallida Species 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
- 229910002026 crystalline silica Inorganic materials 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003607 modifier 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
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 150000003738 xylenes 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
-
- 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20262/82A IT1150699B (it) | 1982-03-19 | 1982-03-19 | Procedimento per la ossidrilazione di idrocarburi aromatici |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8301492D0 SE8301492D0 (sv) | 1983-03-18 |
| SE8301492L SE8301492L (sv) | 1983-09-20 |
| SE461730B true SE461730B (sv) | 1990-03-19 |
Family
ID=11165238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8301492A SE461730B (sv) | 1982-03-19 | 1983-03-18 | Foerfarande foer hydoxylering av aromatiska kolvaeten |
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 |
| 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 |
| FR2666333B1 (fr) * | 1990-08-31 | 1994-04-08 | Rhone Poulenc Chimie | Procede d'hydroxylation de phenols et d'ethers de phenols. |
| JPH06340416A (ja) * | 1990-08-29 | 1994-12-13 | Rhone Poulenc Chim | シリカ及び場合によっては四価元素の酸化物を基材とするゼオライトの製造法 |
| 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 |
| WO1998015514A1 (en) | 1996-10-07 | 1998-04-16 | Solutia Inc. | Process for the hydroxylation of benzene |
| US6156938A (en) * | 1997-04-03 | 2000-12-05 | Solutia, Inc. | Process for making phenol or phenol derivatives |
| BR9815311A (pt) * | 1997-11-14 | 2001-08-07 | Du Pont Pharm Co | Processo para oxidacao de compostos organicos e processo para preparacao de um catalisador de peneira molecular |
| JP2001524475A (ja) * | 1997-11-24 | 2001-12-04 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 有機化合物の選択的酸化方法 |
| 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 |
| AU2003304661A1 (en) * | 2003-12-31 | 2005-07-21 | Council Of Scientific And Industrial Research | Process for conversion of phenol to hydroquinone and quinones |
| BRPI0608355B1 (pt) | 2005-02-17 | 2016-05-24 | Monsanto Technology Llc | processo para oxidação de ácido n-(fosfonometil) iminodiacético ou seu sal e catalisador de oxidação |
| 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 NO NO830926A patent/NO156648C/no not_active IP Right Cessation
- 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
- 1983-03-17 DK DK123783A patent/DK171933B1/da 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
- 1983-03-18 FR FR8304502A patent/FR2523575B1/fr not_active Expired
- 1983-03-18 SE SE8301492A patent/SE461730B/sv not_active IP Right Cessation
- 1983-03-21 BE BE0/210368A patent/BE896225A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL192876B (nl) | 1997-12-01 |
| DE3309669A1 (de) | 1983-09-29 |
| NL192876C (nl) | 1998-04-02 |
| SE8301492D0 (sv) | 1983-03-18 |
| CH652114A5 (it) | 1985-10-31 |
| BE896225A (fr) | 1983-09-21 |
| GB8307296D0 (en) | 1983-04-20 |
| DE3309669C2 (enrdf_load_stackoverflow) | 1990-10-25 |
| IT8220262A0 (it) | 1982-03-19 |
| IT1150699B (it) | 1986-12-17 |
| NL8300962A (nl) | 1983-10-17 |
| GB2116974B (en) | 1985-10-02 |
| DK123783D0 (da) | 1983-03-17 |
| DK123783A (da) | 1983-09-20 |
| SE8301492L (sv) | 1983-09-20 |
| FR2523575A1 (fr) | 1983-09-23 |
| NO156648C (no) | 1987-10-28 |
| IT8220262A1 (it) | 1983-09-19 |
| FR2523575B1 (fr) | 1986-10-10 |
| DK171933B1 (da) | 1997-08-18 |
| GB2116974A (en) | 1983-10-05 |
| NO830926L (no) | 1983-09-20 |
| NO156648B (no) | 1987-07-20 |
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Legal Events
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| NAL | Patent in force |
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