SU890972A3 - Способ получени 4-окси-2,4,6-триметил-циклогексадиен-2,5-она-1 - Google Patents
Способ получени 4-окси-2,4,6-триметил-циклогексадиен-2,5-она-1 Download PDFInfo
- Publication number
- SU890972A3 SU890972A3 SU772531601A SU2531601A SU890972A3 SU 890972 A3 SU890972 A3 SU 890972A3 SU 772531601 A SU772531601 A SU 772531601A SU 2531601 A SU2531601 A SU 2531601A SU 890972 A3 SU890972 A3 SU 890972A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- bis
- oxygen
- mesitol
- ethylenediiminocobalt
- cobalt
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 claims abstract description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000001301 oxygen Substances 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 150000001412 amines Chemical class 0.000 claims abstract description 6
- 239000010941 cobalt Substances 0.000 claims abstract description 4
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000007789 gas Substances 0.000 claims abstract description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract description 2
- ULGPAXANYFUWRP-UHFFFAOYSA-N 4-hydroxy-2,4,6-trimethylcyclohexa-2,5-dien-1-one Chemical compound CC1=CC(C)(O)C=C(C)C1=O ULGPAXANYFUWRP-UHFFFAOYSA-N 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 239000002262 Schiff base Substances 0.000 abstract 1
- 150000004753 Schiff bases Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 239000003426 co-catalyst Substances 0.000 abstract 1
- 229910001882 dioxygen Inorganic materials 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 9
- LJJFDTYXMRFETA-UHFFFAOYSA-N 2-(2,4,6-trimethylphenyl)benzene-1,4-diol Chemical compound CC1=CC(C)=CC(C)=C1C1=CC(O)=CC=C1O LJJFDTYXMRFETA-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 2
- VZHHNBNSMNNUAD-UHFFFAOYSA-N cobalt 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound [Co].OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VZHHNBNSMNNUAD-UHFFFAOYSA-N 0.000 description 2
- 238000001030 gas--liquid chromatography Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- SENUUPBBLQWHMF-UHFFFAOYSA-N 2,6-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C=C(C)C1=O SENUUPBBLQWHMF-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- UCFZBOCMNGFLQX-UHFFFAOYSA-N [Co]N Chemical compound [Co]N UCFZBOCMNGFLQX-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 0.000 description 1
- 230000009466 transformation Effects 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
- C07C45/39—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a secondary hydroxyl group
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7633025A FR2368458A1 (fr) | 1976-10-25 | 1976-10-25 | Procede de preparation d'hydroxy-4 alcoyl-4 cyclohexadiene-2,5 one-1 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU890972A3 true SU890972A3 (ru) | 1981-12-15 |
Family
ID=9179461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772531601A SU890972A3 (ru) | 1976-10-25 | 1977-10-24 | Способ получени 4-окси-2,4,6-триметил-циклогексадиен-2,5-она-1 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4164516A (enExample) |
| BE (1) | BE860084A (enExample) |
| CA (1) | CA1108186A (enExample) |
| CH (1) | CH624657A5 (enExample) |
| DE (1) | DE2747497A1 (enExample) |
| FR (1) | FR2368458A1 (enExample) |
| GB (1) | GB1563045A (enExample) |
| IT (1) | IT1087124B (enExample) |
| NL (1) | NL187204C (enExample) |
| SU (1) | SU890972A3 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1151184B (it) * | 1982-05-20 | 1986-12-17 | Anic Spa | Procedimento per la sintesi di 2,4,6 trimetil-4 idrossicicloesa-2,5 dien-1 one |
| CN102381950B (zh) * | 2011-09-05 | 2014-11-05 | 浙江新和成股份有限公司 | 一种催化氧化制备香兰素的方法 |
| WO2022096701A1 (en) | 2020-11-09 | 2022-05-12 | Dsm Ip Assets B.V. | Formation of p-alkylphenols based on intermolecular reaction of ethyne with 2-alkylfurans in the presence of gold(i) complexes |
| US20240059650A1 (en) * | 2020-12-15 | 2024-02-22 | Dsm Ip Assets B.V. | Photooxidation of 2,4,6-trimethylphenol |
| EP4673421A1 (en) | 2023-03-01 | 2026-01-07 | DSM IP Assets B.V. | Manufacturing 2,3,5-trimethylhydroquinone from a mixture of mesitol and 2,3,6-trimethylphenol |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JPS4897847A (enExample) * | 1972-03-25 | 1973-12-13 | ||
| JPS4949927A (enExample) * | 1972-09-18 | 1974-05-15 | ||
| JPS49134655A (enExample) * | 1973-05-07 | 1974-12-25 | ||
| FR2303785A1 (fr) * | 1975-03-11 | 1976-10-08 | Rhone Poulenc Ind | Procede d'oxydation de cetones b-ethyleniques |
-
1976
- 1976-10-25 FR FR7633025A patent/FR2368458A1/fr active Granted
-
1977
- 1977-10-17 US US05/843,075 patent/US4164516A/en not_active Expired - Lifetime
- 1977-10-20 CA CA289,154A patent/CA1108186A/fr not_active Expired
- 1977-10-22 DE DE19772747497 patent/DE2747497A1/de active Granted
- 1977-10-24 NL NLAANVRAGE7711657,A patent/NL187204C/xx not_active IP Right Cessation
- 1977-10-24 SU SU772531601A patent/SU890972A3/ru active
- 1977-10-24 CH CH1292777A patent/CH624657A5/fr not_active IP Right Cessation
- 1977-10-24 GB GB44217/77A patent/GB1563045A/en not_active Expired
- 1977-10-25 IT IT28975/77A patent/IT1087124B/it active
- 1977-10-25 BE BE182036A patent/BE860084A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7711657A (nl) | 1978-04-27 |
| BE860084A (fr) | 1978-04-25 |
| DE2747497C2 (enExample) | 1988-03-17 |
| CA1108186A (fr) | 1981-09-01 |
| FR2368458A1 (fr) | 1978-05-19 |
| IT1087124B (it) | 1985-05-31 |
| GB1563045A (en) | 1980-03-19 |
| NL187204C (nl) | 1991-07-01 |
| CH624657A5 (enExample) | 1981-08-14 |
| NL187204B (nl) | 1991-02-01 |
| FR2368458B1 (enExample) | 1980-09-19 |
| DE2747497A1 (de) | 1978-04-27 |
| US4164516A (en) | 1979-08-14 |
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