SE448869B - Sett att framstella monoalkyletrar av hydrokinon och derivat derav - Google Patents
Sett att framstella monoalkyletrar av hydrokinon och derivat deravInfo
- Publication number
- SE448869B SE448869B SE8106743A SE8106743A SE448869B SE 448869 B SE448869 B SE 448869B SE 8106743 A SE8106743 A SE 8106743A SE 8106743 A SE8106743 A SE 8106743A SE 448869 B SE448869 B SE 448869B
- Authority
- SE
- Sweden
- Prior art keywords
- hydroquinone
- autoclave
- salt
- reaction
- methanol
- Prior art date
Links
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract description 52
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- -1 hydroquinone compound Chemical class 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims abstract 8
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 claims abstract 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 43
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- 229910021653 sulphate ion Inorganic materials 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000007664 blowing Methods 0.000 claims 1
- 239000003456 ion exchange resin Substances 0.000 claims 1
- 229920003303 ion-exchange polymer Polymers 0.000 claims 1
- 150000002505 iron Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910052723 transition metal Inorganic materials 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 238000004458 analytical method Methods 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000001914 filtration Methods 0.000 description 6
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000000203 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
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 3
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 3
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 3
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 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 1
- 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 1
- WISWUHHSBKNIBE-UHFFFAOYSA-N 6-tert-butyl-1-methoxycyclohexa-2,4-dien-1-ol Chemical compound C(C)(C)(C)C1C(C=CC=C1)(O)OC WISWUHHSBKNIBE-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 229960004251 hydroquinine Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection 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
- 150000002500 ions Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005406 washing Methods 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 |
|---|---|
| SE8106743L SE8106743L (sv) | 1982-05-14 |
| SE448869B true SE448869B (sv) | 1987-03-23 |
Family
ID=26328631
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8106743A SE448869B (sv) | 1980-11-13 | 1981-11-12 | Sett att framstella monoalkyletrar av hydrokinon och derivat derav |
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 |
| 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 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
Ref document number: 8106743-1 Effective date: 19930610 Format of ref document f/p: F |