DE3602180A1 - Verfahren zur herstellung von brenzkatechin und hydrochinon - Google Patents
Verfahren zur herstellung von brenzkatechin und hydrochinonInfo
- Publication number
- DE3602180A1 DE3602180A1 DE19863602180 DE3602180A DE3602180A1 DE 3602180 A1 DE3602180 A1 DE 3602180A1 DE 19863602180 DE19863602180 DE 19863602180 DE 3602180 A DE3602180 A DE 3602180A DE 3602180 A1 DE3602180 A1 DE 3602180A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen peroxide
- phenol
- mol
- sulfur dioxide
- reaction
- 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
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 99
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 35
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims abstract description 34
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims abstract description 24
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 claims abstract description 20
- 230000033444 hydroxylation Effects 0.000 claims abstract description 9
- 238000005805 hydroxylation reaction Methods 0.000 claims abstract description 9
- 235000010269 sulphur dioxide Nutrition 0.000 abstract 1
- 239000004291 sulphur dioxide Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000002253 acid Substances 0.000 description 17
- 150000007513 acids Chemical class 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 5
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 239000008139 complexing agent Substances 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000012190 activator Substances 0.000 description 3
- 150000003934 aromatic aldehydes Chemical class 0.000 description 3
- 150000005205 dihydroxybenzenes Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- -1 pyrophosphoric acid Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001030 gas--liquid chromatography Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000000640 hydroxylating effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- 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
- C07C37/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of other oxidants than molecular oxygen or their mixtures with molecular oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863602180 DE3602180A1 (de) | 1986-01-25 | 1986-01-25 | Verfahren zur herstellung von brenzkatechin und hydrochinon |
| AT86117703T ATE40984T1 (de) | 1986-01-25 | 1986-12-18 | Verfahren zur herstellung von brenzkatechin und hydrochinon. |
| EP86117703A EP0230625B1 (de) | 1986-01-25 | 1986-12-18 | Verfahren zur Herstellung von Brenzkatechin und Hydrochinon |
| DE8686117703T DE3662187D1 (en) | 1986-01-25 | 1986-12-18 | Process for the production of pyrocatechin and hydroquinone |
| ES86117703T ES2007296B3 (es) | 1986-01-25 | 1986-12-18 | Procedimiento para la preparacion de pirocatequina e hidroquinona. |
| BE0/217617A BE906063A (fr) | 1986-01-25 | 1986-12-29 | Procede de preparation de pyrocatechol et d'hydroquinone. |
| JP62009203A JPS62178531A (ja) | 1986-01-25 | 1987-01-20 | ピロカテキンおよびヒドロキノンの製造法 |
| BR8700297A BR8700297A (pt) | 1986-01-25 | 1987-01-23 | Processo para a preparacao de pirocatequina e de hidroquinona |
| US07/007,351 US5026925A (en) | 1986-01-25 | 1987-01-27 | Method of producing catechol and hydroquinone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863602180 DE3602180A1 (de) | 1986-01-25 | 1986-01-25 | Verfahren zur herstellung von brenzkatechin und hydrochinon |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3602180A1 true DE3602180A1 (de) | 1987-07-30 |
| DE3602180C2 DE3602180C2 (en, 2012) | 1987-10-29 |
Family
ID=6292582
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19863602180 Granted DE3602180A1 (de) | 1986-01-25 | 1986-01-25 | Verfahren zur herstellung von brenzkatechin und hydrochinon |
| DE8686117703T Expired DE3662187D1 (en) | 1986-01-25 | 1986-12-18 | Process for the production of pyrocatechin and hydroquinone |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8686117703T Expired DE3662187D1 (en) | 1986-01-25 | 1986-12-18 | Process for the production of pyrocatechin and hydroquinone |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5026925A (en, 2012) |
| EP (1) | EP0230625B1 (en, 2012) |
| JP (1) | JPS62178531A (en, 2012) |
| AT (1) | ATE40984T1 (en, 2012) |
| BE (1) | BE906063A (en, 2012) |
| BR (1) | BR8700297A (en, 2012) |
| DE (2) | DE3602180A1 (en, 2012) |
| ES (1) | ES2007296B3 (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3308726C2 (de) * | 1983-03-11 | 1991-01-24 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Dihydroxybenzolen |
| DE3643206C1 (de) * | 1986-12-18 | 1988-03-24 | Degussa | Verfahren zur Herstellung von substituierten Dihydroxybenzolen |
| KR100394582B1 (ko) * | 1995-11-03 | 2003-11-20 | 삼성종합화학주식회사 | 카테콜과히드로퀴논의제조방법 |
| FR2971783B1 (fr) | 2011-02-17 | 2013-02-15 | Rhodia Operations | Procede d'hydroxylation de phenols et d'ethers de phenols |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2616791A (en) * | 1950-09-30 | 1952-11-04 | Glidden Co | Process for preparing selenium dioxide |
| GB1301709A (en, 2012) * | 1969-12-30 | 1973-01-04 | ||
| DE2138735A1 (de) * | 1971-08-03 | 1973-03-01 | Haarmann & Reimer Gmbh | Verfahren zur herstellung von polyhydroxybenzolen |
| US3943179A (en) * | 1972-09-28 | 1976-03-09 | Rhone-Poulenc Textile | Hydroxylation of aromatic compounds |
| DE2410742B2 (de) * | 1974-03-06 | 1980-04-30 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Brenzkatechin und Hydrochinon durch Kernhydroxylierung von Phenol |
| DE3308763C2 (de) * | 1983-03-11 | 1985-01-24 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Dihydroxybenzolen |
| DE3308737C2 (de) * | 1983-03-11 | 1985-01-24 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Brenzcatechin und Hydrochinon |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3953530A (en) * | 1972-01-10 | 1976-04-27 | S. A. Texaco Belgium N.V. | Process for making o- and p-chlorophenols |
| DE3308769C2 (de) * | 1983-03-11 | 1985-01-24 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Dihydroxybenzolen |
-
1986
- 1986-01-25 DE DE19863602180 patent/DE3602180A1/de active Granted
- 1986-12-18 AT AT86117703T patent/ATE40984T1/de not_active IP Right Cessation
- 1986-12-18 EP EP86117703A patent/EP0230625B1/de not_active Expired
- 1986-12-18 DE DE8686117703T patent/DE3662187D1/de not_active Expired
- 1986-12-18 ES ES86117703T patent/ES2007296B3/es not_active Expired - Lifetime
- 1986-12-29 BE BE0/217617A patent/BE906063A/fr not_active IP Right Cessation
-
1987
- 1987-01-20 JP JP62009203A patent/JPS62178531A/ja active Pending
- 1987-01-23 BR BR8700297A patent/BR8700297A/pt unknown
- 1987-01-27 US US07/007,351 patent/US5026925A/en not_active Expired - Fee Related
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2616791A (en) * | 1950-09-30 | 1952-11-04 | Glidden Co | Process for preparing selenium dioxide |
| GB1301709A (en, 2012) * | 1969-12-30 | 1973-01-04 | ||
| DE2064497C3 (de) * | 1969-12-30 | 1978-08-31 | Rhone-Poulenc S.A., Paris | Verfahren zur Kernhydroxylierung von aromatischen Verbindungen |
| DE2138735A1 (de) * | 1971-08-03 | 1973-03-01 | Haarmann & Reimer Gmbh | Verfahren zur herstellung von polyhydroxybenzolen |
| US3943179A (en) * | 1972-09-28 | 1976-03-09 | Rhone-Poulenc Textile | Hydroxylation of aromatic compounds |
| DE2410742B2 (de) * | 1974-03-06 | 1980-04-30 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Brenzkatechin und Hydrochinon durch Kernhydroxylierung von Phenol |
| DE3308763C2 (de) * | 1983-03-11 | 1985-01-24 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Dihydroxybenzolen |
| DE3308737C2 (de) * | 1983-03-11 | 1985-01-24 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Brenzcatechin und Hydrochinon |
Non-Patent Citations (1)
| Title |
|---|
| Chemiker-Zeitung, 1941, 65, S. 194-95 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0230625A1 (de) | 1987-08-05 |
| JPS62178531A (ja) | 1987-08-05 |
| ATE40984T1 (de) | 1989-03-15 |
| EP0230625B1 (de) | 1989-03-01 |
| ES2007296B3 (es) | 1990-08-16 |
| US5026925A (en) | 1991-06-25 |
| DE3602180C2 (en, 2012) | 1987-10-29 |
| DE3662187D1 (en) | 1989-04-06 |
| BR8700297A (pt) | 1987-12-08 |
| BE906063A (fr) | 1987-06-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8363 | Opposition against the patent | ||
| 8365 | Fully valid after opposition proceedings | ||
| 8330 | Complete renunciation |