DE2237750C2 - Verfahren zur Herstellung von Brenzcatechin - Google Patents
Verfahren zur Herstellung von BrenzcatechinInfo
- Publication number
- DE2237750C2 DE2237750C2 DE2237750A DE2237750A DE2237750C2 DE 2237750 C2 DE2237750 C2 DE 2237750C2 DE 2237750 A DE2237750 A DE 2237750A DE 2237750 A DE2237750 A DE 2237750A DE 2237750 C2 DE2237750 C2 DE 2237750C2
- Authority
- DE
- Germany
- Prior art keywords
- chlorophenol
- theory
- mol
- catechol
- copper
- 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
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 title claims description 50
- 238000000034 method Methods 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title description 3
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical class OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 claims description 31
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 20
- 229910052802 copper Inorganic materials 0.000 claims description 16
- 239000010949 copper Substances 0.000 claims description 16
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 12
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 5
- 230000020477 pH reduction Effects 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 46
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 26
- 235000011121 sodium hydroxide Nutrition 0.000 description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VXHYVVAUHMGCEX-UHFFFAOYSA-N 2-(2-hydroxyphenoxy)phenol Chemical compound OC1=CC=CC=C1OC1=CC=CC=C1O VXHYVVAUHMGCEX-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical class OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- JERCPDZTVRGVSH-UHFFFAOYSA-N benzene-1,2-diol;benzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1.OC1=CC=CC=C1O JERCPDZTVRGVSH-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 150000005205 dihydroxybenzenes Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- BYTCDABWEGFPLT-UHFFFAOYSA-L potassium;sodium;dihydroxide Chemical compound [OH-].[OH-].[Na+].[K+] BYTCDABWEGFPLT-UHFFFAOYSA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/02—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of halogen
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)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2237750A DE2237750C2 (de) | 1972-08-01 | 1972-08-01 | Verfahren zur Herstellung von Brenzcatechin |
| US382233A US3919334A (en) | 1972-08-01 | 1973-07-24 | Process for preparing pyrocatechol |
| JP48085035A JPS504032A (enExample) | 1972-08-01 | 1973-07-30 | |
| NL7310540A NL7310540A (enExample) | 1972-08-01 | 1973-07-30 | |
| BE133991A BE802944A (fr) | 1972-08-01 | 1973-07-30 | Procede de fabrication de pyrocatechine |
| DD168122A DD106349A5 (enExample) | 1972-08-01 | 1973-07-31 | |
| FR7328258A FR2194674A1 (enExample) | 1972-08-01 | 1973-08-01 | |
| GB3653773A GB1414535A (en) | 1972-08-01 | 1973-08-01 | Process for the production of pyrocatechol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2237750A DE2237750C2 (de) | 1972-08-01 | 1972-08-01 | Verfahren zur Herstellung von Brenzcatechin |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2237750A1 DE2237750A1 (enExample) | 1973-10-25 |
| DE2237750B1 DE2237750B1 (de) | 1973-10-25 |
| DE2237750C2 true DE2237750C2 (de) | 1974-06-12 |
Family
ID=5852321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2237750A Expired DE2237750C2 (de) | 1972-08-01 | 1972-08-01 | Verfahren zur Herstellung von Brenzcatechin |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3919334A (enExample) |
| JP (1) | JPS504032A (enExample) |
| BE (1) | BE802944A (enExample) |
| DD (1) | DD106349A5 (enExample) |
| DE (1) | DE2237750C2 (enExample) |
| FR (1) | FR2194674A1 (enExample) |
| GB (1) | GB1414535A (enExample) |
| NL (1) | NL7310540A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS583228B2 (ja) * | 1972-10-02 | 1983-01-20 | 株式会社リコー | デンシシヤシンフクシヤキ ニ オケル ジキゲンゾウブラシ |
| JP2000212330A (ja) | 1999-01-26 | 2000-08-02 | Nippon Zeon Co Ltd | 加硫性ゴム組成物 |
| CN102911018B (zh) * | 2011-08-04 | 2015-05-20 | 浙江龙盛化工研究有限公司 | 一种从间苯二胺酸性水解液中分离含酚有机物的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2041592A (en) * | 1934-10-11 | 1936-05-19 | Pennsylvania Coal Products Com | Process of hydrolyzing chlor phenols |
| US3536767A (en) * | 1967-04-06 | 1970-10-27 | Dow Chemical Co | Manufacture of pyrocatechol |
-
1972
- 1972-08-01 DE DE2237750A patent/DE2237750C2/de not_active Expired
-
1973
- 1973-07-24 US US382233A patent/US3919334A/en not_active Expired - Lifetime
- 1973-07-30 BE BE133991A patent/BE802944A/xx unknown
- 1973-07-30 JP JP48085035A patent/JPS504032A/ja active Pending
- 1973-07-30 NL NL7310540A patent/NL7310540A/xx unknown
- 1973-07-31 DD DD168122A patent/DD106349A5/xx unknown
- 1973-08-01 GB GB3653773A patent/GB1414535A/en not_active Expired
- 1973-08-01 FR FR7328258A patent/FR2194674A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB1414535A (en) | 1975-11-19 |
| DE2237750A1 (enExample) | 1973-10-25 |
| BE802944A (fr) | 1974-01-30 |
| NL7310540A (enExample) | 1974-02-05 |
| FR2194674A1 (enExample) | 1974-03-01 |
| JPS504032A (enExample) | 1975-01-16 |
| US3919334A (en) | 1975-11-11 |
| DE2237750B1 (de) | 1973-10-25 |
| DD106349A5 (enExample) | 1974-06-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Publication of the examined application without previous publication of unexamined application | ||
| C2 | Grant after previous publication (2nd publication) |