DE3145212C2 - Verfahren zur Herstellung von Monoalkyläthern des Hydrochinons und von substituierten Hydrochinonen - Google Patents
Verfahren zur Herstellung von Monoalkyläthern des Hydrochinons und von substituierten HydrochinonenInfo
- Publication number
- DE3145212C2 DE3145212C2 DE3145212A DE3145212A DE3145212C2 DE 3145212 C2 DE3145212 C2 DE 3145212C2 DE 3145212 A DE3145212 A DE 3145212A DE 3145212 A DE3145212 A DE 3145212A DE 3145212 C2 DE3145212 C2 DE 3145212C2
- Authority
- DE
- Germany
- Prior art keywords
- hydroquinone
- autoclave
- methanol
- reaction
- monomethyl ether
- 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
Links
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims abstract description 9
- 150000001346 alkyl aryl ethers Chemical class 0.000 title claims abstract description 5
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 title abstract description 5
- -1 hydroquinone compound Chemical class 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 48
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 7
- 239000001301 oxygen Substances 0.000 abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052723 transition metal Inorganic materials 0.000 abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 11
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 4
- IMOYOUMVYICGCA-UHFFFAOYSA-N 2-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C=C1C(C)(C)C IMOYOUMVYICGCA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 4
- MRBKEAMVRSLQPH-UHFFFAOYSA-N 3-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1 MRBKEAMVRSLQPH-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- 229910015449 FeCU Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 244000078856 Prunus padus Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000008028 pharmaceutical plasticizer Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
Classifications
-
- 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
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25934/80A IT1134243B (it) | 1980-11-13 | 1980-11-13 | Procedimento di preparazione di monoalchileteri dell'idrochinone e dei suoi derivati |
| IT25933/80A IT1134242B (it) | 1980-11-13 | 1980-11-13 | Procedimento per la preparazione di monoalchileteri dell'idrochinone e dei suoi derivati |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3145212A1 DE3145212A1 (de) | 1982-05-19 |
| DE3145212C2 true DE3145212C2 (de) | 1983-10-13 |
Family
ID=26328631
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3145212A Expired DE3145212C2 (de) | 1980-11-13 | 1981-11-13 | Verfahren zur Herstellung von Monoalkyläthern des Hydrochinons und von substituierten Hydrochinonen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4469897A (enExample) |
| CH (1) | CH648279A5 (enExample) |
| DE (1) | DE3145212C2 (enExample) |
| DK (1) | DK496581A (enExample) |
| FR (1) | FR2493834A1 (enExample) |
| GB (1) | GB2087389B (enExample) |
| NL (1) | NL8105149A (enExample) |
| NO (1) | NO154880C (enExample) |
| SE (1) | SE448869B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090312582A1 (en) * | 2005-04-19 | 2009-12-17 | Camlin Fine Chemicals Limited | Synthesis of butylated hydroxyanisole from tertiary butyl hydroquinone |
| US7495097B2 (en) * | 2005-11-23 | 2009-02-24 | Brown University | Rhodium quinonoid catalysts |
| US7569734B2 (en) * | 2005-11-30 | 2009-08-04 | Brown University | Method of using rhodium quinonoid catalysts |
| CN101613260B (zh) * | 2009-07-21 | 2013-05-15 | 广东省食品工业研究所 | 一种特丁基羟基茴香醚的合成及纯化工艺 |
| CN101704727B (zh) * | 2009-10-29 | 2013-03-06 | 广东省食品工业研究所 | 一种从叔丁基羟基茴香醚生产过程中回收叔丁基对苯二酚的工艺 |
| EP3124009A1 (en) | 2015-07-27 | 2017-02-01 | DENTSPLY DETREY GmbH | Dental adhesive |
| EP3124477B1 (en) | 2015-07-27 | 2019-07-17 | DENTSPLY DETREY GmbH | Dental adhesive |
| EP3338757A1 (en) | 2016-12-20 | 2018-06-27 | Dentsply DeTrey GmbH | Direct dental filling composition |
| CN112871190B (zh) * | 2021-01-13 | 2021-08-20 | 泰州九润环保科技有限公司 | 用于合成氢醌单甲醚的铬基金属有机骨架固体酸催化剂及其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2615051A (en) * | 1952-10-21 | Etherification of hydroquinone | ||
| US2781404A (en) * | 1953-12-28 | 1957-02-12 | Universal Oil Prod Co | Synthesis of ortho-alkyl-p-alkoxyphenols |
| US3911022A (en) * | 1973-06-04 | 1975-10-07 | Eastman Kodak Co | Etherification of phenolic compounds |
| JPS51105021A (en) * | 1975-03-13 | 1976-09-17 | Ube Industries | 2 kafuenooruno monoarukirueeterunoseiho |
| JPS5312790A (en) * | 1976-07-23 | 1978-02-04 | Ube Ind Ltd | Vapor phase monoalkyl etherification catalyst for divalent phenols |
-
1981
- 1981-10-21 US US06/313,677 patent/US4469897A/en not_active Expired - Lifetime
- 1981-10-21 GB GB8131713A patent/GB2087389B/en not_active Expired
- 1981-11-03 FR FR8120598A patent/FR2493834A1/fr active Granted
- 1981-11-06 CH CH7128/81A patent/CH648279A5/it not_active IP Right Cessation
- 1981-11-10 DK DK496581A patent/DK496581A/da not_active Application Discontinuation
- 1981-11-11 NO NO813814A patent/NO154880C/no unknown
- 1981-11-12 SE SE8106743A patent/SE448869B/sv not_active IP Right Cessation
- 1981-11-13 NL NL8105149A patent/NL8105149A/nl not_active Application Discontinuation
- 1981-11-13 DE DE3145212A patent/DE3145212C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NO154880B (no) | 1986-09-29 |
| NL8105149A (nl) | 1982-06-01 |
| NO813814L (no) | 1982-05-14 |
| SE8106743L (sv) | 1982-05-14 |
| FR2493834A1 (fr) | 1982-05-14 |
| US4469897A (en) | 1984-09-04 |
| FR2493834B1 (enExample) | 1984-06-01 |
| CH648279A5 (it) | 1985-03-15 |
| DK496581A (da) | 1982-05-14 |
| DE3145212A1 (de) | 1982-05-19 |
| GB2087389B (en) | 1984-05-10 |
| GB2087389A (en) | 1982-05-26 |
| NO154880C (no) | 1987-01-07 |
| SE448869B (sv) | 1987-03-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69407846T2 (de) | Verfahren zur Herstellung von Carbonsäuren oder ihrer Ester in gegenwart des auf Iridium basierten Katalysators | |
| DE2600541C3 (de) | Verfahren zur Herstellung von Phenylbrenztraubensäure oder Arylbrenztraubensäuren | |
| EP0893426A1 (de) | 2-Phasen-Herstellung von Carbonsäureestern | |
| DE3145212C2 (de) | Verfahren zur Herstellung von Monoalkyläthern des Hydrochinons und von substituierten Hydrochinonen | |
| DE69512639T2 (de) | Verfahren zur herstellung von zimtsäurederivaten | |
| DE2427875C3 (de) | Verfahren zur Gewinnung von Dimethylterephthalat und von Zwischenprodukten der Dimethylterephthalat-Herstellung | |
| DE69310017T2 (de) | Verfahren zur Herstellung von funktionalisierten Perfluorpolyoxyalkylenen | |
| DE69516548T2 (de) | Verfahren zur Herstellung von Cyclopropancarboxamid | |
| DE2903890C2 (de) | Verfahren zur kontinuierlichen Herstellung von Äthylenglykolmonoäthylätheracetat | |
| DE69016460T2 (de) | Verfahren zur herstellung von 2-ethylhexyl-para-methoxycinnamat. | |
| EP0234013A1 (de) | Verfahren zur Herstellung von Perfluorcarbonsäuren | |
| EP0052314B2 (de) | Herstellung von Monoalkyläthern von Hydroxyphenolen | |
| EP0087585A1 (de) | Verfahren zur Herstellung von 3-Alkoxi-acrylnitrilen | |
| DE69511384T2 (de) | Verbessertes verfahren zur herstellung von beta-diketonen | |
| DE69014683T2 (de) | Verfahren zur Herstellung von Lithium-Diphenylphosphino-phenyl-m-sulfonat. | |
| EP0455119A2 (de) | Verfahren zur Herstellung von Canthaxanthin und Astaxanthin | |
| DE2503926A1 (de) | Verfahren zur herstellung von vinylestern von carbonsaeuren | |
| DE69301305T2 (de) | Herstellung von Isofluran | |
| DE60317626T2 (de) | Verfahren zur herstellung von 2,5-bis(trifluormethyl)nitrobenzol | |
| DE69104782T2 (de) | Verfahren zur Herstellung von ungesättigten Bromiden. | |
| EP0983223A1 (de) | Verfahren zur herstellung von acetophenonen, die am aromatischen kern mit fluoralkyl substituiert sind | |
| DE3030734C2 (de) | Verfahren zur Herstellung von wasserfreier Diglykolsäure | |
| EP0128489B1 (de) | Verfahren zur Herstellung von Succinylobernsteinsäuredialkylestern | |
| DE69107149T2 (de) | Verfahren zur Herstellung von p-Halogenbenzophenonderivaten. | |
| EP0180801B1 (de) | Trägerkatalysator für die Herstellung von Monocarbonsäureanhydriden |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: ENICHEM SYNTHESIS S.P.A., PALERMO, IT |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: ZUMSTEIN, F., DIPL.-CHEM. DR.RER.NAT. KLINGSEISEN, F., DIPL.-ING., PAT.-ANWAELTE, 8000 MUENCHEN |
|
| 8339 | Ceased/non-payment of the annual fee |