JPH04210954A - 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 - Google Patents
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Info
- Publication number
- JPH04210954A JPH04210954A JP5406491A JP5406491A JPH04210954A JP H04210954 A JPH04210954 A JP H04210954A JP 5406491 A JP5406491 A JP 5406491A JP 5406491 A JP5406491 A JP 5406491A JP H04210954 A JPH04210954 A JP H04210954A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- disulfonic acid
- reaction
- disulfonic
- dinitronaphthalene
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- 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 claims abstract 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 61
- 238000000034 method Methods 0.000 claims abstract description 20
- 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 abstract description 15
- 238000006722 reduction reaction Methods 0.000 claims abstract description 13
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 11
- 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 abstract description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000006396 nitration reaction Methods 0.000 claims abstract description 9
- 230000007062 hydrolysis Effects 0.000 claims abstract description 8
- 230000000802 nitrating effect Effects 0.000 claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 40
- 239000002253 acid Substances 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 12
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 12
- 229910017604 nitric acid Inorganic materials 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- 235000019270 ammonium chloride Nutrition 0.000 claims description 6
- 230000018044 dehydration Effects 0.000 claims description 6
- 238000006297 dehydration reaction Methods 0.000 claims description 6
- 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 5
- 239000003792 electrolyte Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 3
- 239000007810 chemical reaction solvent Substances 0.000 claims description 3
- YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000006277 sulfonation reaction Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 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 abstract description 3
- 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 22
- 239000000543 intermediate Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 7
- -1 ammonium H acid salt Chemical class 0.000 description 6
- 238000004811 liquid chromatography Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-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
- 238000004458 analytical method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 238000011946 reduction process Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 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 1
- RJKGJBPXVHTNJL-UHFFFAOYSA-N 1-nitronaphthalene Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1 RJKGJBPXVHTNJL-UHFFFAOYSA-N 0.000 description 1
- 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
- TZBROGJRQUABOK-UHFFFAOYSA-N 4-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 TZBROGJRQUABOK-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 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 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- UTFRXVRPQCQDAD-UHFFFAOYSA-L dipotassium;naphthalene-2,7-disulfonate Chemical compound [K+].[K+].C1=CC(S([O-])(=O)=O)=CC2=CC(S(=O)(=O)[O-])=CC=C21 UTFRXVRPQCQDAD-UHFFFAOYSA-L 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000000975 dye 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
- 239000012467 final product Substances 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 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
- ZPBSAMLXSQCSOX-UHFFFAOYSA-N naphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 ZPBSAMLXSQCSOX-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 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 |
|---|---|---|---|
| JP5406491A 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 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5406491A 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 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16013482A Division 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04210954A true JPH04210954A (ja) | 1992-08-03 |
| JPH0524146B2 JPH0524146B2 (enrdf_load_html_response) | 1993-04-06 |
Family
ID=12960190
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5406491A Granted 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 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04210954A (enrdf_load_html_response) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102775808A (zh) * | 2012-08-23 | 2012-11-14 | 楚源高新科技集团股份有限公司 | 一种利用t酸母液废水回收硫酸铵和合成酸性染料的工艺 |
| CN102936213A (zh) * | 2011-08-15 | 2013-02-20 | 中国中化股份有限公司 | 一种1,8-二硝基-3,6-萘二磺酸的清洁制备方法 |
| CN106698744A (zh) * | 2016-12-06 | 2017-05-24 | 浙江力禾集团有限公司 | 一种去除h酸废水中水合肼的方法 |
-
1991
- 1991-02-25 JP JP5406491A patent/JPH04210954A/ja active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102936213A (zh) * | 2011-08-15 | 2013-02-20 | 中国中化股份有限公司 | 一种1,8-二硝基-3,6-萘二磺酸的清洁制备方法 |
| CN102775808A (zh) * | 2012-08-23 | 2012-11-14 | 楚源高新科技集团股份有限公司 | 一种利用t酸母液废水回收硫酸铵和合成酸性染料的工艺 |
| CN106698744A (zh) * | 2016-12-06 | 2017-05-24 | 浙江力禾集团有限公司 | 一种去除h酸废水中水合肼的方法 |
| CN106698744B (zh) * | 2016-12-06 | 2019-10-18 | 浙江力禾集团有限公司 | 一种去除h酸废水中水合肼的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0524146B2 (enrdf_load_html_response) | 1993-04-06 |
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