CA1041540A - Hydrolysis of 3,5-diamino benzoic acid to produce alpha-resorcylic acid - Google Patents
Hydrolysis of 3,5-diamino benzoic acid to produce alpha-resorcylic acidInfo
- Publication number
- CA1041540A CA1041540A CA234,856A CA234856A CA1041540A CA 1041540 A CA1041540 A CA 1041540A CA 234856 A CA234856 A CA 234856A CA 1041540 A CA1041540 A CA 1041540A
- Authority
- CA
- Canada
- Prior art keywords
- alpha
- acid
- benzoic acid
- diamino benzoic
- resorcylic
- 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 abstract description 57
- 238000006460 hydrolysis reaction Methods 0.000 title claims abstract description 28
- UENRXLSRMCSUSN-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical compound NC1=CC(N)=CC(C(O)=O)=C1 UENRXLSRMCSUSN-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 230000007062 hydrolysis Effects 0.000 title abstract description 24
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000011541 reaction mixture Substances 0.000 claims abstract description 13
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 235000011130 ammonium sulphate Nutrition 0.000 claims abstract description 12
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims abstract description 11
- 239000007864 aqueous solution Substances 0.000 claims abstract description 7
- 239000000243 solution Substances 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 abstract description 4
- 239000000376 reactant Substances 0.000 abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- 238000000605 extraction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 3
- 238000000354 decomposition reaction 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
- 239000000155 melt 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
- 239000012736 aqueous medium Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 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
- 239000011368 organic material Substances 0.000 description 2
- 238000003303 reheating Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000252067 Megalops atlanticus Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 230000000332 continued effect Effects 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052920 inorganic sulfate Inorganic materials 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
- 239000000463 material Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 230000004580 weight loss Effects 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 (1)
| Publication Number | Publication Date |
|---|---|
| CA1041540A true CA1041540A (en) | 1978-10-31 |
Family
ID=24161974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA234,856A Expired CA1041540A (en) | 1975-01-17 | 1975-09-05 | Hydrolysis of 3,5-diamino benzoic acid to produce alpha-resorcylic acid |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5846495B2 (enrdf_load_html_response) |
| BE (1) | BE833181A (enrdf_load_html_response) |
| BR (1) | BR7507685A (enrdf_load_html_response) |
| CA (1) | CA1041540A (enrdf_load_html_response) |
| DE (1) | DE2601091C3 (enrdf_load_html_response) |
| FR (1) | FR2297831A2 (enrdf_load_html_response) |
| IT (1) | IT1060532B (enrdf_load_html_response) |
| NL (1) | NL157886B (enrdf_load_html_response) |
-
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 JP JP11592475A patent/JPS5846495B2/ja not_active Expired
- 1975-09-25 NL NL7511279A patent/NL157886B/xx not_active IP Right Cessation
- 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 |
|---|---|
| NL7511279A (nl) | 1976-07-20 |
| DE2601091C3 (de) | 1979-03-22 |
| DE2601091B2 (de) | 1978-07-27 |
| JPS5159833A (en) | 1976-05-25 |
| BR7507685A (pt) | 1976-08-24 |
| FR2297831A2 (fr) | 1976-08-13 |
| JPS5846495B2 (ja) | 1983-10-17 |
| NL157886B (nl) | 1978-09-15 |
| BE833181A (fr) | 1975-12-31 |
| FR2297831B2 (enrdf_load_html_response) | 1979-07-20 |
| DE2601091A1 (de) | 1976-07-22 |
| IT1060532B (it) | 1982-08-20 |
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