DE2716030C3 - Verfahren zur Herstellung von Monoalkalisalzes der 1-Amino-8-naphthol-3,6-disulfonsäure - Google Patents
Verfahren zur Herstellung von Monoalkalisalzes der 1-Amino-8-naphthol-3,6-disulfonsäureInfo
- Publication number
- DE2716030C3 DE2716030C3 DE19772716030 DE2716030A DE2716030C3 DE 2716030 C3 DE2716030 C3 DE 2716030C3 DE 19772716030 DE19772716030 DE 19772716030 DE 2716030 A DE2716030 A DE 2716030A DE 2716030 C3 DE2716030 C3 DE 2716030C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- salt
- water
- naphthylamine
- 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.)
- Expired
Links
- 150000003839 salts Chemical class 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title claims description 4
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 title description 3
- 239000002253 acid Substances 0.000 claims description 103
- 239000000203 mixture Substances 0.000 claims description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 9
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 8
- 239000011707 mineral Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims description 2
- 230000008021 deposition Effects 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
- UBDHSURDYAETAL-UHFFFAOYSA-N 8-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 UBDHSURDYAETAL-UHFFFAOYSA-N 0.000 description 44
- 235000002639 sodium chloride Nutrition 0.000 description 32
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 235000011121 sodium hydroxide Nutrition 0.000 description 18
- 150000007513 acids Chemical class 0.000 description 16
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 10
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 10
- -1 B. 1-naphthylamine-3 Chemical class 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- 235000011118 potassium hydroxide Nutrition 0.000 description 5
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical class [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VEUACKUBDLVUAC-UHFFFAOYSA-N [Na].[Ca] Chemical compound [Na].[Ca] VEUACKUBDLVUAC-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 3
- AFGPCIMUGMJQPD-UHFFFAOYSA-L disodium;4,5-dihydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(O)=C2C(O)=CC(S([O-])(=O)=O)=CC2=C1 AFGPCIMUGMJQPD-UHFFFAOYSA-L 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- HLVXFWDLRHCZEI-UHFFFAOYSA-N chromotropic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HLVXFWDLRHCZEI-UHFFFAOYSA-N 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 229940099990 ogen Drugs 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 2
- 229910052939 potassium sulfate Inorganic materials 0.000 description 2
- 235000011151 potassium sulphates Nutrition 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- DEUOBQUHDSDIFY-UHFFFAOYSA-N sulfur trioxide;hydrate Chemical compound O.O=S(=O)=O DEUOBQUHDSDIFY-UHFFFAOYSA-N 0.000 description 2
- RJKGJBPXVHTNJL-UHFFFAOYSA-N 1-nitronaphthalene Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1 RJKGJBPXVHTNJL-UHFFFAOYSA-N 0.000 description 1
- JQIUQZOYSRHTBE-UHFFFAOYSA-N 4-nitronaphthalene-1,2,3-trisulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(S(O)(=O)=O)C(S(=O)(=O)O)=C([N+]([O-])=O)C2=C1 JQIUQZOYSRHTBE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 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
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 description 1
- 101100346764 Mus musculus Mtln gene Proteins 0.000 description 1
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 description 1
- 241000238633 Odonata Species 0.000 description 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- 241000109329 Rosa xanthina Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- GBAOBIBJACZTNA-UHFFFAOYSA-L calcium sulfite Chemical compound [Ca+2].[O-]S([O-])=O GBAOBIBJACZTNA-UHFFFAOYSA-L 0.000 description 1
- 235000010261 calcium sulphite Nutrition 0.000 description 1
- 229960002173 citrulline Drugs 0.000 description 1
- 235000013477 citrulline Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- WFWWBGDDTJRGQF-UHFFFAOYSA-N naphthalen-1-amine Chemical compound C1=CC=C2C(N)=CC=CC2=C1.C1=CC=C2C(N)=CC=CC2=C1 WFWWBGDDTJRGQF-UHFFFAOYSA-N 0.000 description 1
- KLYWOECPXNAJPC-UHFFFAOYSA-N naphthalen-1-amine;naphthalen-2-amine Chemical compound C1=CC=CC2=CC(N)=CC=C21.C1=CC=C2C(N)=CC=CC2=C1 KLYWOECPXNAJPC-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 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
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772716030 DE2716030C3 (de) | 1977-04-09 | 1977-04-09 | Verfahren zur Herstellung von Monoalkalisalzes der 1-Amino-8-naphthol-3,6-disulfonsäure |
| GB13142/78A GB1577697A (en) | 1977-04-09 | 1978-04-04 | Process for the preparation of 1 - amino - 8 - naphthol-3,6-disulphonic acid (h-acid) |
| CH371478A CH634045A5 (en) | 1977-04-09 | 1978-04-06 | Process for preparing mono alkali-metal salts of 1-amino-8-naphthol-3,6-disulphonic acid |
| JP4045178A JPS53127448A (en) | 1977-04-09 | 1978-04-07 | Method for production of 11aminoo88naphtholl3 * 66disulfonate of monoalkalimetal |
| BE2056856A BE865774A (fr) | 1977-04-09 | 1978-04-07 | Procede de preparation de l'acide 1-amino-8-naphtol-3,6-disulfonique (acide "h") |
| FR7810429A FR2386520A1 (fr) | 1977-04-09 | 1978-04-07 | Procede de preparation de l'acide 1-amino-8-naphtol-3,6-disulfonique (acide " h ") |
| BR7802175A BR7802175A (pt) | 1977-04-09 | 1978-04-07 | Processo para a preparacao de sais monoalcalinos de acido 1-amino-8-naftol-3,6-dissulfonico |
| IT48792/78A IT1156158B (it) | 1977-04-09 | 1978-04-07 | Procedimento per produrre sali mono-alcalini di acido 1-ammino-8-naftol-3,6-disolfonico |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772716030 DE2716030C3 (de) | 1977-04-09 | 1977-04-09 | Verfahren zur Herstellung von Monoalkalisalzes der 1-Amino-8-naphthol-3,6-disulfonsäure |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2716030A1 DE2716030A1 (de) | 1978-10-19 |
| DE2716030B2 DE2716030B2 (de) | 1980-09-11 |
| DE2716030C3 true DE2716030C3 (de) | 1981-07-16 |
Family
ID=6006077
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772716030 Expired DE2716030C3 (de) | 1977-04-09 | 1977-04-09 | Verfahren zur Herstellung von Monoalkalisalzes der 1-Amino-8-naphthol-3,6-disulfonsäure |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS53127448A (cg-RX-API-DMAC7.html) |
| BE (1) | BE865774A (cg-RX-API-DMAC7.html) |
| BR (1) | BR7802175A (cg-RX-API-DMAC7.html) |
| CH (1) | CH634045A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2716030C3 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2386520A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1577697A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1156158B (cg-RX-API-DMAC7.html) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2834166A1 (de) * | 1978-08-04 | 1980-02-28 | Bayer Ag | Verfahren zur herstellung von 1-amino-8-naphthol-3,6-disulfonsaeure (h-saeure) |
| DE2843680A1 (de) * | 1978-10-06 | 1980-04-24 | Bayer Ag | Verfahren zur herstellung von 1-amino-8-naphthol-4,6-disulfonsaeure (k-saeure) |
| DE3118147A1 (de) * | 1981-05-07 | 1982-12-02 | Bayer Ag, 5090 Leverkusen | Verfahren zur isolierung von h-saeure und k-saeure |
| JPS6388617A (ja) * | 1986-10-01 | 1988-04-19 | Mitsubishi Electric Corp | 比例制御ガバナ |
| CN109096154A (zh) * | 2018-08-16 | 2018-12-28 | 山东裕源集团有限公司 | 一种h酸生产工艺 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR550850A (fr) * | 1921-12-12 | 1923-03-21 | Nouveau procédé de préparation de l'acide h | |
| US1670406A (en) * | 1925-05-09 | 1928-05-22 | Newport Co | Process of preparing h-acid |
| US2272272A (en) * | 1939-09-02 | 1942-02-10 | Allied Chem & Dye Corp | Process for preparing hydroxy naphthalene compounds |
| JPS52156844A (en) * | 1976-06-21 | 1977-12-27 | Sumitomo Chem Co Ltd | Preparation of 8-amino-1-naphthol-3,6-disulfonic acid |
| CH630067A5 (de) * | 1977-03-31 | 1982-05-28 | Ciba Geigy Ag | Verfahren zur herstellung von naphthylaminhydroxysulfosaeuren. |
| DE2732291A1 (de) * | 1977-07-16 | 1979-02-01 | Bayer Ag | Verfahren zur herstellung von 1-amino-8-naphthol-3,6-disulfonsaeure (h-saeure) |
-
1977
- 1977-04-09 DE DE19772716030 patent/DE2716030C3/de not_active Expired
-
1978
- 1978-04-04 GB GB13142/78A patent/GB1577697A/en not_active Expired
- 1978-04-06 CH CH371478A patent/CH634045A5/de not_active IP Right Cessation
- 1978-04-07 BR BR7802175A patent/BR7802175A/pt unknown
- 1978-04-07 FR FR7810429A patent/FR2386520A1/fr active Granted
- 1978-04-07 BE BE2056856A patent/BE865774A/xx not_active IP Right Cessation
- 1978-04-07 JP JP4045178A patent/JPS53127448A/ja active Granted
- 1978-04-07 IT IT48792/78A patent/IT1156158B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS53127448A (en) | 1978-11-07 |
| CH634045A5 (en) | 1983-01-14 |
| IT1156158B (it) | 1987-01-28 |
| BE865774A (fr) | 1978-10-09 |
| FR2386520B1 (cg-RX-API-DMAC7.html) | 1984-08-31 |
| FR2386520A1 (fr) | 1978-11-03 |
| GB1577697A (en) | 1980-10-29 |
| BR7802175A (pt) | 1978-12-19 |
| JPS5645910B2 (cg-RX-API-DMAC7.html) | 1981-10-29 |
| DE2716030B2 (de) | 1980-09-11 |
| IT7848792A0 (it) | 1978-04-07 |
| DE2716030A1 (de) | 1978-10-19 |
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