JPH0419987B2 - - Google Patents
Info
- Publication number
- JPH0419987B2 JPH0419987B2 JP16013482A JP16013482A JPH0419987B2 JP H0419987 B2 JPH0419987 B2 JP H0419987B2 JP 16013482 A JP16013482 A JP 16013482A JP 16013482 A JP16013482 A JP 16013482A JP H0419987 B2 JPH0419987 B2 JP H0419987B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- reaction
- disulfonic acid
- dinitronaphthalene
- disulfonic
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 51
- 238000006243 chemical reaction Methods 0.000 claims description 49
- 239000002253 acid Substances 0.000 claims description 37
- 238000004519 manufacturing process Methods 0.000 claims description 24
- VILFVXYKHXVYAB-UHFFFAOYSA-N naphthalene-2,7-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 VILFVXYKHXVYAB-UHFFFAOYSA-N 0.000 claims description 12
- XFKRPUUIHKVIDM-UHFFFAOYSA-N 4,5-dinitronaphthalene-2,7-disulfonic acid Chemical compound [O-][N+](=O)C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC([N+]([O-])=O)=C21 XFKRPUUIHKVIDM-UHFFFAOYSA-N 0.000 claims description 11
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 11
- 229910017604 nitric acid Inorganic materials 0.000 claims description 11
- VGHJNLKOGBNGTR-UHFFFAOYSA-N 4-nitronaphthalene-2,7-disulfonic acid Chemical compound [O-][N+](=O)C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 VGHJNLKOGBNGTR-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 230000018044 dehydration Effects 0.000 claims description 8
- 238000006297 dehydration reaction Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- 239000007810 chemical reaction solvent Substances 0.000 claims description 5
- -1 1-nitronaphthalene- 1,8-dinitronaphthalene Chemical compound 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 230000000802 nitrating effect Effects 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000005070 ripening Effects 0.000 claims description 2
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 claims 1
- 230000002250 progressing effect Effects 0.000 claims 1
- 239000000543 intermediate Substances 0.000 description 14
- 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 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- 238000006396 nitration reaction Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 238000004811 liquid chromatography Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- BRSYMBVQGUKXPE-UHFFFAOYSA-N 4,5-diaminonaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 BRSYMBVQGUKXPE-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002159 abnormal effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- AVCSMMMOCOTIHF-UHFFFAOYSA-N 1,8-dinitronaphthalene Chemical compound C1=CC([N+]([O-])=O)=C2C([N+](=O)[O-])=CC=CC2=C1 AVCSMMMOCOTIHF-UHFFFAOYSA-N 0.000 description 2
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- RWSMEUGBSLLVNA-UHFFFAOYSA-N 3,4-dinitronaphthalene-2,7-disulfonic acid Chemical compound [O-][N+](=O)C1=C([N+]([O-])=O)C(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 RWSMEUGBSLLVNA-UHFFFAOYSA-N 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical compound [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- OESVLPLHBXKGGT-UHFFFAOYSA-L disodium 4,5-diaminonaphthalene-2,7-disulfonate Chemical compound [Na+].NC1=CC(=CC2=CC(=CC(=C12)N)S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+] OESVLPLHBXKGGT-UHFFFAOYSA-L 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000007788 liquid Substances 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
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 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 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16013482A JPS5951253A (ja) | 1982-09-14 | 1982-09-14 | １・８―ジニトロナフタレン―３・６―ジスルホン酸の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16013482A JPS5951253A (ja) | 1982-09-14 | 1982-09-14 | １・８―ジニトロナフタレン―３・６―ジスルホン酸の製造法 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5406491A Division JPH04210954A (ja) | 1991-02-25 | 1991-02-25 | １−アミノ−８−ヒドロキシナフタレン−３・６−ジスルホン酸の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5951253A JPS5951253A (ja) | 1984-03-24 |
| JPH0419987B2 true JPH0419987B2 (en]) | 1992-03-31 |
Family
ID=15708602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16013482A Granted JPS5951253A (ja) | 1982-09-14 | 1982-09-14 | １・８―ジニトロナフタレン―３・６―ジスルホン酸の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5951253A (en]) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110256302B (zh) * | 2019-06-27 | 2020-07-17 | 山东创蓝垚石环保技术有限公司 | 一种络合萃取生产h酸的方法 |
| CN112774616A (zh) * | 2020-12-18 | 2021-05-11 | 尹诺士国际股份有限公司 | 二硝基萘的制备方法 |
-
1982
- 1982-09-14 JP JP16013482A patent/JPS5951253A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5951253A (ja) | 1984-03-24 |
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