DE2706842C2 - Verfahren zur Herstellung von 2,3,5-Trimethylhydrochinon - Google Patents
Verfahren zur Herstellung von 2,3,5-TrimethylhydrochinonInfo
- Publication number
- DE2706842C2 DE2706842C2 DE2706842A DE2706842A DE2706842C2 DE 2706842 C2 DE2706842 C2 DE 2706842C2 DE 2706842 A DE2706842 A DE 2706842A DE 2706842 A DE2706842 A DE 2706842A DE 2706842 C2 DE2706842 C2 DE 2706842C2
- Authority
- DE
- Germany
- Prior art keywords
- dimethylformamide
- butyl ether
- trimethylhydroquinone
- weight
- water
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 5
- AUFZRCJENRSRLY-UHFFFAOYSA-N 2,3,5-trimethylhydroquinone Chemical compound CC1=CC(O)=C(C)C(C)=C1O AUFZRCJENRSRLY-UHFFFAOYSA-N 0.000 title description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 70
- 239000003054 catalyst Substances 0.000 claims description 14
- 230000003647 oxidation Effects 0.000 claims description 11
- 238000007254 oxidation reaction Methods 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 229910000510 noble metal Inorganic materials 0.000 claims description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 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 13
- 239000002244 precipitate Substances 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000007791 liquid phase Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- XRUGBBIQLIVCSI-UHFFFAOYSA-N 2,3,4-trimethylphenol Chemical compound CC1=CC=C(O)C(C)=C1C XRUGBBIQLIVCSI-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000000926 separation method Methods 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
- -1 B. Dimethylformamide Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000004700 cobalt complex Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 236TMPh Natural products CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-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
- 206010067482 No adverse event Diseases 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004697 chelate complex Chemical class 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation
- C07C37/07—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation with simultaneous reduction of C=O group in that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/08—Dihydroxy benzenes; Alkylated derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/10—Separation; Purification; Stabilisation; Use of additives
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 |
|---|---|---|---|
| GB660676 | 1976-02-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2706842A1 DE2706842A1 (de) | 1977-09-01 |
| DE2706842C2 true DE2706842C2 (de) | 1985-10-24 |
Family
ID=9817538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2706842A Expired DE2706842C2 (de) | 1976-02-19 | 1977-02-17 | Verfahren zur Herstellung von 2,3,5-Trimethylhydrochinon |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4250335A (enExample) |
| JP (1) | JPS6039056B2 (enExample) |
| CH (1) | CH628317A5 (enExample) |
| DE (1) | DE2706842C2 (enExample) |
| FR (1) | FR2341551A1 (enExample) |
| GB (1) | GB1526571A (enExample) |
| NL (1) | NL7701671A (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS567734A (en) * | 1979-06-28 | 1981-01-27 | Takeda Chem Ind Ltd | Preparation of quinone derivative |
| US4545937A (en) * | 1983-04-18 | 1985-10-08 | University Of Delaware | Binucleating ligand-metal complexes as oxidation catalysts |
| DE3404337A1 (de) * | 1984-02-08 | 1985-08-08 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von trimethylhydrochinon |
| GB8423739D0 (en) * | 1984-09-19 | 1984-10-24 | British Petroleum Co Plc | Preparations of quinones |
| JPS61223870A (ja) * | 1985-03-29 | 1986-10-04 | Mita Ind Co Ltd | 電子写真感光体からの転写紙分離装置 |
| US4806688A (en) * | 1986-05-16 | 1989-02-21 | The Dow Chemical Company | Preparation of diamino- and dialkylaminobenzenediols |
| US8226850B1 (en) * | 2009-09-22 | 2012-07-24 | Clemson University Research Foundation | Thermally enhanced oxygen scavengers including a transition metal and a free radical scavenger |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2259936A (en) * | 1937-07-30 | 1941-10-21 | Merck & Co Inc | Process of preparing durohydroquinone |
| US2229573A (en) * | 1938-05-04 | 1941-01-21 | Merck & Co Inc | Process for the production of trimethylhydroquinones |
| US3658853A (en) * | 1970-03-05 | 1972-04-25 | Searle & Co | 17alpha-(2-alkynyl)-11beta-methylestra-1 3 5(10)-triene-3 17beta-diols and esters thereof |
| JPS5442964B2 (enExample) * | 1972-03-03 | 1979-12-17 | ||
| FR2213927B1 (enExample) * | 1973-01-15 | 1977-07-22 | Rhone Poulenc Ind |
-
1977
- 1977-02-17 JP JP52015604A patent/JPS6039056B2/ja not_active Expired
- 1977-02-17 GB GB6606/76A patent/GB1526571A/en not_active Expired
- 1977-02-17 CH CH198977A patent/CH628317A5/de not_active IP Right Cessation
- 1977-02-17 DE DE2706842A patent/DE2706842C2/de not_active Expired
- 1977-02-17 NL NL7701671A patent/NL7701671A/xx not_active Application Discontinuation
- 1977-02-17 FR FR7704542A patent/FR2341551A1/fr active Granted
- 1977-02-17 US US05/769,810 patent/US4250335A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1526571A (en) | 1978-09-27 |
| JPS6039056B2 (ja) | 1985-09-04 |
| NL7701671A (nl) | 1977-08-23 |
| FR2341551A1 (fr) | 1977-09-16 |
| CH628317A5 (de) | 1982-02-26 |
| DE2706842A1 (de) | 1977-09-01 |
| US4250335A (en) | 1981-02-10 |
| JPS52100430A (en) | 1977-08-23 |
| FR2341551B1 (enExample) | 1979-03-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: JUNG, E., DIPL.-CHEM. DR.PHIL. SCHIRDEWAHN, J., DI |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |