NL8105149A - Werkwijze ter bereiding van de monoalkylethers van hydrochinon alsmede de derivaten daarvan. - Google Patents
Werkwijze ter bereiding van de monoalkylethers van hydrochinon alsmede de derivaten daarvan. Download PDFInfo
- Publication number
- NL8105149A NL8105149A NL8105149A NL8105149A NL8105149A NL 8105149 A NL8105149 A NL 8105149A NL 8105149 A NL8105149 A NL 8105149A NL 8105149 A NL8105149 A NL 8105149A NL 8105149 A NL8105149 A NL 8105149A
- Authority
- NL
- Netherlands
- Prior art keywords
- hydroquinone
- autoclave
- reaction
- process according
- methanol
- Prior art date
Links
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 150000001346 alkyl aryl ethers Chemical class 0.000 title claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 hydroquinone compound Chemical class 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000001301 oxygen Substances 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 7
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 49
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 150000001805 chlorine compounds Chemical group 0.000 claims description 4
- 230000005587 bubbling Effects 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- 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 claims 1
- 239000003456 ion exchange resin Substances 0.000 claims 1
- 229920003303 ion-exchange polymer Polymers 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 23
- 239000003054 catalyst Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 6
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 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 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229960003280 cupric chloride Drugs 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 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 2
- LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 238000002474 experimental method Methods 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
- 239000002904 solvent Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 2
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 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
- QXCOHSRHFCHCHN-UHFFFAOYSA-N 2-chloropyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(Cl)=C1 QXCOHSRHFCHCHN-UHFFFAOYSA-N 0.000 description 1
- QXZBVXIQHVQHNX-UHFFFAOYSA-N 2-tert-butyl-3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1C(C)(C)C QXZBVXIQHVQHNX-UHFFFAOYSA-N 0.000 description 1
- BVCOHOSEBKQIQD-UHFFFAOYSA-N 2-tert-butyl-6-methoxyphenol Chemical compound COC1=CC=CC(C(C)(C)C)=C1O BVCOHOSEBKQIQD-UHFFFAOYSA-N 0.000 description 1
- NCCTVAJNFXYWTM-UHFFFAOYSA-N 2-tert-butylcyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)(C)C1=CC(=O)C=CC1=O NCCTVAJNFXYWTM-UHFFFAOYSA-N 0.000 description 1
- 101150073426 Ctsj gene Proteins 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 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
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001879 copper 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
- 238000001035 drying Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 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
- 150000002505 iron Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
- 239000000178 monomer Substances 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
- 150000004053 quinones Chemical class 0.000 description 1
- 238000011084 recovery 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
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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 (4)
| 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 |
| IT2593380 | 1980-11-13 | ||
| IT2593480 | 1980-11-13 | ||
| IT25933/80A IT1134242B (it) | 1980-11-13 | 1980-11-13 | Procedimento per la preparazione di monoalchileteri dell'idrochinone e dei suoi derivati |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8105149A true NL8105149A (nl) | 1982-06-01 |
Family
ID=26328631
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8105149A NL8105149A (nl) | 1980-11-13 | 1981-11-13 | Werkwijze ter bereiding van de monoalkylethers van hydrochinon alsmede de derivaten daarvan. |
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 |
| NO813814L (no) | 1982-05-14 |
| SE8106743L (sv) | 1982-05-14 |
| FR2493834A1 (fr) | 1982-05-14 |
| US4469897A (en) | 1984-09-04 |
| DE3145212C2 (de) | 1983-10-13 |
| 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 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| A85 | Still pending on 85-01-01 | ||
| BC | A request for examination has been filed | ||
| DNT | Communications of changes of names of applicants whose applications have been laid open to public inspection |
Free format text: ENICHEM ANIC S.P.A. |
|
| CNR | Transfer of rights (patent application after its laying open for public inspection) |
Free format text: ENICHEM SYNTHESIS S.P.A. |
|
| BV | The patent application has lapsed |