SU633467A3 - Способ получени триметил -бензохинона - Google Patents
Способ получени триметил -бензохинонаInfo
- Publication number
- SU633467A3 SU633467A3 SU691357561A SU1357561A SU633467A3 SU 633467 A3 SU633467 A3 SU 633467A3 SU 691357561 A SU691357561 A SU 691357561A SU 1357561 A SU1357561 A SU 1357561A SU 633467 A3 SU633467 A3 SU 633467A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- theoretical
- oxygen
- trimethyl
- benzoquinones
- solvent
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 236TMPh Natural products CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 7
- -1 tetramethyl-substituted benzoquinones Chemical class 0.000 description 6
- 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 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000004054 benzoquinones Chemical class 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- OGRAOKJKVGDSFR-UHFFFAOYSA-N 2,3,5-trimethylphenol Chemical compound CC1=CC(C)=C(C)C(O)=C1 OGRAOKJKVGDSFR-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 150000004700 cobalt complex Chemical class 0.000 description 1
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- ZNUSBSVDROQNFN-UHFFFAOYSA-N pentane-2,3-diamine Chemical compound CCC(N)C(C)N ZNUSBSVDROQNFN-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Classifications
-
- 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
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681793183 DE1793183B1 (de) | 1968-08-13 | 1968-08-13 | Verfahren zur Herstellung von Trimethyl-p-benzochinon |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU633467A3 true SU633467A3 (ru) | 1978-11-15 |
Family
ID=5707604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU691357561A SU633467A3 (ru) | 1968-08-13 | 1969-08-11 | Способ получени триметил -бензохинона |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3658852A (enExample) |
| JP (1) | JPS4840341B1 (enExample) |
| AT (1) | AT289084B (enExample) |
| BE (1) | BE737375A (enExample) |
| CH (1) | CH501573A (enExample) |
| CS (1) | CS150986B2 (enExample) |
| DE (1) | DE1793183B1 (enExample) |
| DK (1) | DK143444C (enExample) |
| ES (1) | ES370464A1 (enExample) |
| FR (1) | FR2015576A1 (enExample) |
| GB (1) | GB1268653A (enExample) |
| NL (1) | NL156389B (enExample) |
| SU (1) | SU633467A3 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4360469A (en) * | 1970-06-11 | 1982-11-23 | Eastman Kodak Company | Preparation of quinones by salcomine-catalyzed oxidation of phenols |
| US3966818A (en) * | 1972-03-25 | 1976-06-29 | Teijin Limited | Novel process for preparation of 4-hydroxy-2,4,6-trimethyl-2,5-cyclohexadiene-1-one |
| US3966776A (en) * | 1973-03-09 | 1976-06-29 | Takasago Perfumery Co., Ltd. | Process for preparing parabenzoquinones |
| US3859317A (en) * | 1973-09-28 | 1975-01-07 | Goodyear Tire & Rubber | Process of preparing p-benzoquinone |
| US3935247A (en) * | 1973-09-28 | 1976-01-27 | The Goodyear Tire & Rubber Company | Oxidation of alkylated phenols to p-benzoquinones |
| FR2249062B1 (enExample) * | 1973-10-25 | 1976-10-01 | Rhone Poulenc Ind | |
| GB1455753A (en) * | 1974-01-08 | 1976-11-17 | Shell Int Research | Process for de preparation of p-quinones |
| US4132722A (en) * | 1976-11-26 | 1979-01-02 | Ici Americas Inc. | Oxidative coupling of alkylphenols catalyzed by metal complexes of diimino acid |
| JPS55121196U (enExample) * | 1979-02-22 | 1980-08-28 | ||
| JPS567734A (en) * | 1979-06-28 | 1981-01-27 | Takeda Chem Ind Ltd | Preparation of quinone derivative |
| US4909965A (en) * | 1981-08-03 | 1990-03-20 | E. I. Du Pont De Nemours And Company | Salcomine-catalyzed oxidation of phenols |
| DE3215095A1 (de) * | 1982-04-23 | 1983-10-27 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 2,3,5-trimethyl-l-p-benzochinon |
| US6693221B1 (en) | 2003-04-04 | 2004-02-17 | General Electric Company | Method of preparing mixtures of bromophenols and benzoquinones |
| US6815565B2 (en) * | 2003-04-04 | 2004-11-09 | General Electric Company | Method for preparing hydroquinones and dihydroxybiphenyl compounds from mixtures of bromophenols and benzoquinones |
| CN117402050B (zh) * | 2022-07-06 | 2025-07-25 | 大连理工大学 | 一种钴催化2,3,6-三甲基苯酚合成2,3,5-三甲基苯醌的方法 |
-
1968
- 1968-08-13 DE DE19681793183 patent/DE1793183B1/de active Pending
-
1969
- 1969-07-25 AT AT719769A patent/AT289084B/de not_active IP Right Cessation
- 1969-08-05 CH CH1190369A patent/CH501573A/de not_active IP Right Cessation
- 1969-08-05 US US847726A patent/US3658852A/en not_active Expired - Lifetime
- 1969-08-11 SU SU691357561A patent/SU633467A3/ru active
- 1969-08-11 FR FR6927518A patent/FR2015576A1/fr active Pending
- 1969-08-12 NL NL6912263.A patent/NL156389B/xx not_active IP Right Cessation
- 1969-08-12 DK DK432369A patent/DK143444C/da not_active IP Right Cessation
- 1969-08-12 CS CS5571A patent/CS150986B2/cs unknown
- 1969-08-12 GB GB40176/69A patent/GB1268653A/en not_active Expired
- 1969-08-12 BE BE737375D patent/BE737375A/xx not_active IP Right Cessation
- 1969-08-13 ES ES370464A patent/ES370464A1/es not_active Expired
- 1969-08-13 JP JP44063581A patent/JPS4840341B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL156389B (nl) | 1978-04-17 |
| CH501573A (de) | 1971-01-15 |
| US3658852A (en) | 1972-04-25 |
| ES370464A1 (es) | 1971-04-16 |
| DE1793183B1 (de) | 1972-03-16 |
| BE737375A (enExample) | 1970-02-12 |
| FR2015576A1 (enExample) | 1970-04-30 |
| NL6912263A (enExample) | 1970-02-17 |
| JPS4840341B1 (enExample) | 1973-11-30 |
| DK143444B (da) | 1981-08-24 |
| AT289084B (de) | 1971-04-13 |
| DK143444C (da) | 1981-12-28 |
| CS150986B2 (enExample) | 1973-09-17 |
| GB1268653A (en) | 1972-03-29 |
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