JPS63280040A - ２，３，５−トリメチルベンゾキノンの製造方法 - Google Patents
２，３，５−トリメチルベンゾキノンの製造方法Info
- Publication number
- JPS63280040A JPS63280040A JP62116665A JP11666587A JPS63280040A JP S63280040 A JPS63280040 A JP S63280040A JP 62116665 A JP62116665 A JP 62116665A JP 11666587 A JP11666587 A JP 11666587A JP S63280040 A JPS63280040 A JP S63280040A
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- reaction
- trimethylbenzoquinone
- catalyst
- producing
- 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.)
- Granted
Links
- QIXDHVDGPXBRRD-UHFFFAOYSA-N 2,3,5-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C(C)=C(C)C1=O QIXDHVDGPXBRRD-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 49
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims abstract description 40
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 236TMPh Natural products CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 claims abstract description 38
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims abstract description 36
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 239000002904 solvent Substances 0.000 claims abstract description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 23
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 21
- 229960003280 cupric chloride Drugs 0.000 claims abstract description 18
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims abstract description 18
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 14
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 9
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000008096 xylene Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 25
- 238000007254 oxidation reaction Methods 0.000 claims description 22
- 239000007789 gas Substances 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 230000003647 oxidation Effects 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 abstract description 22
- -1 2,3,6-trimethylphenyl Chemical group 0.000 abstract description 11
- 239000007864 aqueous solution Substances 0.000 abstract description 10
- 230000001590 oxidative effect Effects 0.000 abstract description 7
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 229930003427 Vitamin E Natural products 0.000 abstract description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 abstract description 2
- 229940046009 vitamin E Drugs 0.000 abstract description 2
- 235000019165 vitamin E Nutrition 0.000 abstract description 2
- 239000011709 vitamin E Substances 0.000 abstract description 2
- OGRAOKJKVGDSFR-UHFFFAOYSA-N 2,3,5-trimethylphenol Chemical compound CC1=CC(C)=C(C)C(O)=C1 OGRAOKJKVGDSFR-UHFFFAOYSA-N 0.000 abstract 2
- 229940079593 drug Drugs 0.000 abstract 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 49
- 239000008346 aqueous phase Substances 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000012043 crude product Substances 0.000 description 13
- 239000007810 chemical reaction solvent Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 10
- 238000004817 gas chromatography Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000011259 mixed solution Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000012046 mixed solvent Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 238000005273 aeration Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QRKCWASFYYFORH-UHFFFAOYSA-N 2-(6-hydroxy-2,3,4-trimethylphenyl)-3,4,5-trimethylphenol Chemical compound CC1=C(C)C(C)=CC(O)=C1C1=C(C)C(C)=C(C)C=C1O QRKCWASFYYFORH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- FINHMKGKINIASC-UHFFFAOYSA-N Tetramethylpyrazine Chemical compound CC1=NC(C)=C(C)N=C1C FINHMKGKINIASC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- OKDOZOFJAUITTD-UHFFFAOYSA-N propan-1-ol;toluene Chemical compound CCCO.CC1=CC=CC=C1 OKDOZOFJAUITTD-UHFFFAOYSA-N 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/02—Quinones with monocyclic quinoid structure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
- C07C46/06—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring
- C07C46/08—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring with molecular oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/02—Quinones with monocyclic quinoid structure
- C07C50/04—Benzoquinones, i.e. C6H4O2
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)
- Catalysts (AREA)
- Pyrane Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62116665A JPS63280040A (ja) | 1987-05-13 | 1987-05-13 | ２，３，５−トリメチルベンゾキノンの製造方法 |
| EP88107105A EP0294584B1 (en) | 1987-05-13 | 1988-05-03 | Process for preparing 2,3,5-trimethylbenzoquinone |
| ES198888107105T ES2037760T3 (es) | 1987-05-13 | 1988-05-03 | Un procedimiento para preparar 2,3,5-trimetilbenzoquinona. |
| AT88107105T ATE71612T1 (de) | 1987-05-13 | 1988-05-03 | Verfahren zur herstellung von 2,3,5trimethylbenzochinon. |
| DE8888107105T DE3867711D1 (de) | 1987-05-13 | 1988-05-03 | Verfahren zur herstellung von 2,3,5-trimethylbenzochinon. |
| KR1019880005410A KR910004483B1 (ko) | 1987-05-13 | 1988-05-10 | 2,3,5-트리메틸벤조퀴논의 제조방법 |
| US07/192,661 US5104996A (en) | 1987-05-13 | 1988-05-11 | Process for preparing 2,3,5-trimethylbenzoquinone |
| CN88102750A CN1024188C (zh) | 1987-05-13 | 1988-05-12 | 2.3.5-三甲基苯醌的制备方法 |
| CA000566580A CA1312615C (en) | 1987-05-13 | 1988-05-12 | Process for preparing 2,3,5-trimethylbenzoquinone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62116665A JPS63280040A (ja) | 1987-05-13 | 1987-05-13 | ２，３，５−トリメチルベンゾキノンの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63280040A true JPS63280040A (ja) | 1988-11-17 |
| JPH0451536B2 JPH0451536B2 (en, 2012) | 1992-08-19 |
Family
ID=14692862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62116665A Granted JPS63280040A (ja) | 1987-05-13 | 1987-05-13 | ２，３，５−トリメチルベンゾキノンの製造方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5104996A (en, 2012) |
| EP (1) | EP0294584B1 (en, 2012) |
| JP (1) | JPS63280040A (en, 2012) |
| KR (1) | KR910004483B1 (en, 2012) |
| CN (1) | CN1024188C (en, 2012) |
| AT (1) | ATE71612T1 (en, 2012) |
| CA (1) | CA1312615C (en, 2012) |
| DE (1) | DE3867711D1 (en, 2012) |
| ES (1) | ES2037760T3 (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016526549A (ja) * | 2013-07-02 | 2016-09-05 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ２，３，６−トリメチルフェノールの酸化による２，３，５−トリメチルベンゾキノンの製造方法 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0338666B1 (en) * | 1988-03-16 | 1992-05-20 | Japan as represented by Director-General, Agency of Industrial Science and Technology | Method for the preparation of 2,3,5-trimethylbenzoquinone |
| EP0369823B1 (en) * | 1988-11-18 | 1993-06-16 | THE STATE OF JAPAN, as Represented by the DIRECTOR GENERAL of the AGENCY of INDUSTRIAL SCIENCE and TECHNOLOGY | Method for the preparation of 2,3,5-trimethylbenzoquinone |
| DE3908768A1 (de) * | 1989-03-17 | 1990-09-20 | Basf Ag | Verfahren zur herstellung von 2,3,5-trimethyl-p-benzochinon |
| DE4029198A1 (de) * | 1990-09-14 | 1992-03-19 | Basf Ag | Verfahren zur herstellung von 2,3,5-trimethyl-p-benzochinon |
| DE19949795A1 (de) | 1999-10-15 | 2001-04-19 | Degussa | Verfahren zur Herstellung von 2,3,5-Trimethyl-p-benzochinon |
| RU2165406C1 (ru) * | 2000-04-10 | 2001-04-20 | Институт катализа им. Г.К. Борескова СО РАН | Способ получения 2,3,5-триметил-1,4-бензохинона и катализатор для его осуществления |
| US20050137409A1 (en) * | 2003-12-18 | 2005-06-23 | Sunil Ashtekar | Processes for preparing benzoquinones and hydroquinones |
| CN102584559B (zh) * | 2012-01-10 | 2013-10-16 | 西北化工研究院 | 一种分离纯化2,3,5-三甲基苯醌的方法 |
| KR20160029026A (ko) | 2013-07-02 | 2016-03-14 | 바스프 에스이 | 2-에틸헥사날 및 3-헵틸 포르메이트를 함유하는 혼합물로부터의 3-헵타놀의 제조 방법 |
| CN113083339B (zh) * | 2021-04-15 | 2022-11-08 | 万华化学(四川)有限公司 | 一种用于制备维生素e的催化剂及其制备方法和应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1952652A1 (de) * | 1969-10-18 | 1971-04-29 | Basf Ag | Verfahren zur katalytischen Oxydation von alkylsubstituierten Hydrochinonen zu den entsprechenden p-Benzochinonen |
| IL39225A (en) * | 1971-05-17 | 1975-07-28 | Sparamedica Ag | Process for the manufacture of methyl substituted p-benzoquinones |
| DE2630896C3 (de) * | 1976-07-09 | 1979-10-04 | Balcke-Duerr Ag, 4030 Ratingen | Vorrichtung zum Abbiegen großflächiger Bauteile |
| FR2408570A1 (fr) * | 1977-06-27 | 1979-06-08 | Rhone Poulenc Ind | Procede de preparation de para-benzoquinone |
| CA1192212A (en) * | 1981-07-20 | 1985-08-20 | James E. Lyons | Process for oxidizing phenol to p-benzoquinone |
| JPS59225137A (ja) * | 1983-06-06 | 1984-12-18 | Mitsubishi Gas Chem Co Inc | ２，３，５−トリメチルベンゾキノンの製造方法 |
| JPS6117532A (ja) * | 1984-07-03 | 1986-01-25 | Mitsubishi Gas Chem Co Inc | ２，３，５−トリメチルベンゾキノンの製造法 |
-
1987
- 1987-05-13 JP JP62116665A patent/JPS63280040A/ja active Granted
-
1988
- 1988-05-03 EP EP88107105A patent/EP0294584B1/en not_active Expired - Lifetime
- 1988-05-03 DE DE8888107105T patent/DE3867711D1/de not_active Expired - Fee Related
- 1988-05-03 AT AT88107105T patent/ATE71612T1/de not_active IP Right Cessation
- 1988-05-03 ES ES198888107105T patent/ES2037760T3/es not_active Expired - Lifetime
- 1988-05-10 KR KR1019880005410A patent/KR910004483B1/ko not_active Expired
- 1988-05-11 US US07/192,661 patent/US5104996A/en not_active Expired - Lifetime
- 1988-05-12 CN CN88102750A patent/CN1024188C/zh not_active Expired - Fee Related
- 1988-05-12 CA CA000566580A patent/CA1312615C/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016526549A (ja) * | 2013-07-02 | 2016-09-05 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ２，３，６−トリメチルフェノールの酸化による２，３，５−トリメチルベンゾキノンの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0451536B2 (en, 2012) | 1992-08-19 |
| CA1312615C (en) | 1993-01-12 |
| ES2037760T3 (es) | 1993-07-01 |
| US5104996A (en) | 1992-04-14 |
| CN88102750A (zh) | 1988-11-30 |
| DE3867711D1 (de) | 1992-02-27 |
| CN1024188C (zh) | 1994-04-13 |
| KR880013868A (ko) | 1988-12-22 |
| ATE71612T1 (de) | 1992-02-15 |
| EP0294584A1 (en) | 1988-12-14 |
| EP0294584B1 (en) | 1992-01-15 |
| KR910004483B1 (ko) | 1991-06-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313111 |
|
| R350 | Written notification of registration of transfer |
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