DE2813570C2 - Verfahren zur Herstellung von Naphthylaminhydroxysulfosäuren - Google Patents
Verfahren zur Herstellung von NaphthylaminhydroxysulfosäurenInfo
- Publication number
- DE2813570C2 DE2813570C2 DE19782813570 DE2813570A DE2813570C2 DE 2813570 C2 DE2813570 C2 DE 2813570C2 DE 19782813570 DE19782813570 DE 19782813570 DE 2813570 A DE2813570 A DE 2813570A DE 2813570 C2 DE2813570 C2 DE 2813570C2
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- acid
- naphthylamine
- melt
- 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
- -1 naphthylamine hydroxysulfonic acids Chemical class 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 2
- 239000012670 alkaline solution Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 53
- 239000000243 solution Substances 0.000 description 23
- 235000011121 sodium hydroxide Nutrition 0.000 description 17
- 239000000047 product Substances 0.000 description 15
- 239000000155 melt Substances 0.000 description 14
- KZCSUEYBKAPKNH-UHFFFAOYSA-N 6-aminonaphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KZCSUEYBKAPKNH-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- ZCNCWYFISJTFHB-UHFFFAOYSA-N 4-hydroxy-7-(methylamino)naphthalene-2-sulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(NC)=CC=C21 ZCNCWYFISJTFHB-UHFFFAOYSA-N 0.000 description 2
- GFPQSWFFPRQEHH-UHFFFAOYSA-N 7-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1S(O)(=O)=O GFPQSWFFPRQEHH-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- VNWVMZDJPMCAKD-UHFFFAOYSA-N 3-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1O VNWVMZDJPMCAKD-UHFFFAOYSA-N 0.000 description 1
- ZKOUEUSBTLIJBN-UHFFFAOYSA-N 6-(methylamino)naphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(NC)=CC=C21 ZKOUEUSBTLIJBN-UHFFFAOYSA-N 0.000 description 1
- CMOLPZZVECHXKN-UHFFFAOYSA-N 7-aminonaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 CMOLPZZVECHXKN-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- GRDCROBOCRWKQQ-UHFFFAOYSA-L disodium;6-(methylamino)naphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(S([O-])(=O)=O)=CC2=CC(NC)=CC=C21 GRDCROBOCRWKQQ-UHFFFAOYSA-L 0.000 description 1
- YKOUFOHKVHDKRS-UHFFFAOYSA-L disodium;6-aminonaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(S([O-])(=O)=O)=CC2=CC(N)=CC=C21 YKOUFOHKVHDKRS-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000005002 naphthylamines Chemical class 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000008237 rinsing water Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH406777A CH630067A5 (de) | 1977-03-31 | 1977-03-31 | Verfahren zur herstellung von naphthylaminhydroxysulfosaeuren. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2813570A1 DE2813570A1 (de) | 1978-10-12 |
| DE2813570C2 true DE2813570C2 (de) | 1986-02-06 |
Family
ID=4269196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782813570 Expired DE2813570C2 (de) | 1977-03-31 | 1978-03-29 | Verfahren zur Herstellung von Naphthylaminhydroxysulfosäuren |
Country Status (8)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2716030C3 (de) * | 1977-04-09 | 1981-07-16 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Monoalkalisalzes der 1-Amino-8-naphthol-3,6-disulfonsäure |
| DE2843680A1 (de) * | 1978-10-06 | 1980-04-24 | Bayer Ag | Verfahren zur herstellung von 1-amino-8-naphthol-4,6-disulfonsaeure (k-saeure) |
| DE3330445A1 (de) * | 1983-08-24 | 1985-03-21 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von als feststoffe anfallenden chemischen verbindungen aus fluessigen ausgangsstoffen |
| US20090036918A1 (en) * | 2006-11-13 | 2009-02-05 | Burgess James E | Method and Apparatus for the Containment of a Surgical Site |
| CN104961661B (zh) * | 2015-06-15 | 2016-06-08 | 金华恒利康化工有限公司 | 一种制备1-氨基-8-萘酚-4，6-二磺酸的方法 |
| CN104860852B (zh) * | 2015-06-15 | 2016-06-22 | 项敬来 | 一种制备1-氨基-8-萘酚-4，6-二磺酸的系统 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US458286A (en) * | 1891-08-25 | Werke | ||
| US540412A (en) * | 1895-06-04 | Moritz ulrich and johann bammann | ||
| CA550645A (en) * | 1957-12-24 | General Aniline And Film Corporation | Process for the preparation of beta-naphthol sulphonic acid | |
| US1670406A (en) * | 1925-05-09 | 1928-05-22 | Newport Co | Process of preparing h-acid |
| US1573056A (en) * | 1925-05-09 | 1926-02-16 | Newport Co | Process of preparing 1, 8-aminonaphthol sulphonic acids |
| US2272272A (en) * | 1939-09-02 | 1942-02-10 | Allied Chem & Dye Corp | Process for preparing hydroxy naphthalene compounds |
-
1977
- 1977-03-31 CH CH406777A patent/CH630067A5/de not_active IP Right Cessation
-
1978
- 1978-03-29 DE DE19782813570 patent/DE2813570C2/de not_active Expired
- 1978-03-29 FR FR7809090A patent/FR2385692A1/fr active Granted
- 1978-03-30 BE BE186391A patent/BE865480A/xx not_active IP Right Cessation
- 1978-03-30 GB GB1256078A patent/GB1602926A/en not_active Expired
- 1978-03-30 BR BR7801949A patent/BR7801949A/pt unknown
- 1978-03-31 JP JP3696378A patent/JPS53121750A/ja active Granted
-
1979
- 1979-06-25 US US06/051,659 patent/US4376737A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2385692A1 (fr) | 1978-10-27 |
| JPS53121750A (en) | 1978-10-24 |
| JPS6317057B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-04-12 |
| FR2385692B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-07-25 |
| CH630067A5 (de) | 1982-05-28 |
| BE865480A (fr) | 1978-10-02 |
| DE2813570A1 (de) | 1978-10-12 |
| BR7801949A (pt) | 1979-01-02 |
| GB1602926A (en) | 1981-11-18 |
| US4376737A (en) | 1983-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAM | Search report available | ||
| OC | Search report available | ||
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: SCHWABE, H., DIPL.-ING. SANDMAIR, K., DIPL.-CHEM. |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: BAYER AG, 5090 LEVERKUSEN, DE |
|
| 8339 | Ceased/non-payment of the annual fee |