DE2601091C3 - Verfahren zur Herstellung von a-Resorcylsäure - Google Patents
Verfahren zur Herstellung von a-ResorcylsäureInfo
- Publication number
- DE2601091C3 DE2601091C3 DE19762601091 DE2601091A DE2601091C3 DE 2601091 C3 DE2601091 C3 DE 2601091C3 DE 19762601091 DE19762601091 DE 19762601091 DE 2601091 A DE2601091 A DE 2601091A DE 2601091 C3 DE2601091 C3 DE 2601091C3
- Authority
- DE
- Germany
- Prior art keywords
- hydrolysis
- acid
- reaction
- ammonium bisulfate
- ammonium
- 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
- UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 24
- 230000007062 hydrolysis Effects 0.000 claims description 22
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- UENRXLSRMCSUSN-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical compound NC1=CC(N)=CC(C(O)=O)=C1 UENRXLSRMCSUSN-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 9
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 8
- 235000011130 ammonium sulphate Nutrition 0.000 description 8
- 238000000605 extraction Methods 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- KKTUQAYCCLMNOA-UHFFFAOYSA-N 2,3-diaminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1N KKTUQAYCCLMNOA-UHFFFAOYSA-N 0.000 description 1
- FRPHFZCDPYBUAU-UHFFFAOYSA-N Bromocresolgreen Chemical compound CC1=C(Br)C(O)=C(Br)C=C1C1(C=2C(=C(Br)C(O)=C(Br)C=2)C)C2=CC=CC=C2S(=O)(=O)O1 FRPHFZCDPYBUAU-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052920 inorganic sulfate Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/542,008 US3984466A (en) | 1972-06-29 | 1975-01-17 | Hydrolysis of 3,5-diamino benzoic acid to produce alpha-resorcylic acid |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2601091A1 DE2601091A1 (de) | 1976-07-22 |
| DE2601091B2 DE2601091B2 (de) | 1978-07-27 |
| DE2601091C3 true DE2601091C3 (de) | 1979-03-22 |
Family
ID=24161974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762601091 Expired DE2601091C3 (de) | 1975-01-17 | 1976-01-14 | Verfahren zur Herstellung von a-Resorcylsäure |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5846495B2 (enExample) |
| BE (1) | BE833181A (enExample) |
| BR (1) | BR7507685A (enExample) |
| CA (1) | CA1041540A (enExample) |
| DE (1) | DE2601091C3 (enExample) |
| FR (1) | FR2297831A2 (enExample) |
| IT (1) | IT1060532B (enExample) |
| NL (1) | NL157886B (enExample) |
-
1975
- 1975-09-05 CA CA234,856A patent/CA1041540A/en not_active Expired
- 1975-09-08 BE BE159837A patent/BE833181A/xx not_active IP Right Cessation
- 1975-09-25 NL NL7511279A patent/NL157886B/xx not_active IP Right Cessation
- 1975-09-25 JP JP11592475A patent/JPS5846495B2/ja not_active Expired
- 1975-11-20 BR BR7507685A patent/BR7507685A/pt unknown
- 1975-12-19 FR FR7539011A patent/FR2297831A2/fr active Granted
-
1976
- 1976-01-05 IT IT4751476A patent/IT1060532B/it active
- 1976-01-14 DE DE19762601091 patent/DE2601091C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5846495B2 (ja) | 1983-10-17 |
| DE2601091B2 (de) | 1978-07-27 |
| FR2297831B2 (enExample) | 1979-07-20 |
| IT1060532B (it) | 1982-08-20 |
| BE833181A (fr) | 1975-12-31 |
| NL157886B (nl) | 1978-09-15 |
| NL7511279A (nl) | 1976-07-20 |
| DE2601091A1 (de) | 1976-07-22 |
| FR2297831A2 (fr) | 1976-08-13 |
| CA1041540A (en) | 1978-10-31 |
| JPS5159833A (en) | 1976-05-25 |
| BR7507685A (pt) | 1976-08-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2360706C3 (de) | Verfahren zur Regeneration von Schwefelsäure | |
| DE68904760T2 (de) | Regeneration von erschoepften schwefelsaeuren mittels wasserstoffperoxyd. | |
| DE2601091C3 (de) | Verfahren zur Herstellung von a-Resorcylsäure | |
| DE2444425A1 (de) | Verfahren zum behandeln eisen(iii)nitrat enthaltender waessriger salpetersaeureloesungen | |
| DE1695253C3 (de) | Verfahren zur gleichzeitigen Herstellung von Caprolactam und w-Dodecalactam | |
| DE2558399C3 (de) | Verfahren zur Herstellung von 3,6-Dichlorpicolinsäure | |
| DE3880902T2 (de) | Verfahren zur herstellung von hydroxybenzoesaeure. | |
| DE2459149C2 (de) | Verfahren zur Herstellung von Resorcin | |
| EP0001792A1 (de) | Verfahren zur Aufbereitung von Abwasser | |
| DE3873983T2 (de) | Verfahren zur herstellung von halogenierten imiden. | |
| DE2421039C2 (de) | Verfahren zur Gewinnung von Diisopropylbenzolmonohydroperoxid | |
| DE2459233C2 (de) | Verfahren zur Herstellung von Hydrochinon | |
| DE1168420B (de) | Verfahren zur Herstellung von Isonitroso-Carbonylverbindungen | |
| DE2601163C3 (de) | Verfahren zur Herstellung von Methylresorcin | |
| EP0084674A1 (de) | Verfahren zur Reinigung von Abfallschwefelsäure | |
| CH644576A5 (de) | Verfahren zur herstellung von anisaldehyd. | |
| DE1808389C3 (de) | Verfahren zur Herstellung von Resorcin durch Säurehydrolyse von m-Phenylendiamin | |
| DE932013C (de) | Verfahren zur Herstellung von ªÏ-Benzoylaminocarbonsaeuren | |
| AT330162B (de) | Verfahren zur herstellung von substituierten 1,1-diphenyl-2-nitropropanen und -butanen | |
| CH426810A (de) | Verfahren zur Herstellung von 2-Äthylisonicotinsäurethioamid aus 2-Äthylpyridin | |
| DE1620478C3 (de) | Verfahren zur Herstellung von omega-Laurinolactam | |
| DE1298979B (de) | Verfahren zur Reinigung von Terephthalsaeure | |
| DE102004012873A1 (de) | Lagerstabile Iminodisuccinatlösungen | |
| DE1917033A1 (de) | Verfahren zur Herstellung von Wasserstoffperoxyd | |
| DE2934495B1 (de) | Verfahren zur Gewinnung farbloser,Trimethylamin- und Dichlorethan-freier waessriger Chlorcholinchloridloesungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |