JPH0354934B2 - - Google Patents
Info
- Publication number
- JPH0354934B2 JPH0354934B2 JP11559787A JP11559787A JPH0354934B2 JP H0354934 B2 JPH0354934 B2 JP H0354934B2 JP 11559787 A JP11559787 A JP 11559787A JP 11559787 A JP11559787 A JP 11559787A JP H0354934 B2 JPH0354934 B2 JP H0354934B2
- Authority
- JP
- Japan
- Prior art keywords
- naphthalenedisulfonic acid
- acid
- added
- salt
- naphthalenedisulfonic
- 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
- FITZJYAVATZPMJ-UHFFFAOYSA-N naphthalene-2,6-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(S(=O)(=O)O)=CC=C21 FITZJYAVATZPMJ-UHFFFAOYSA-N 0.000 claims description 60
- -1 2,6-naphthalenedisulfonic acid diamine salt Chemical class 0.000 claims description 33
- 239000003795 chemical substances by application Substances 0.000 claims description 30
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 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 claims description 16
- 150000001447 alkali salts Chemical class 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 14
- 239000011707 mineral Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 239000003513 alkali Substances 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 150000004984 aromatic diamines Chemical class 0.000 claims description 10
- 239000000706 filtrate Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 238000004064 recycling Methods 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 23
- 239000000203 mixture Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 150000004985 diamines Chemical class 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 13
- 238000000926 separation method Methods 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 10
- 238000006277 sulfonation reaction Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- 239000012452 mother liquor Substances 0.000 description 8
- 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 description 8
- 238000001914 filtration Methods 0.000 description 7
- WZZLWPIYWZEJOX-UHFFFAOYSA-L disodium;naphthalene-2,6-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=CC2=CC(S(=O)(=O)[O-])=CC=C21 WZZLWPIYWZEJOX-UHFFFAOYSA-L 0.000 description 6
- GPUMPJNVOBTUFM-UHFFFAOYSA-N naphthalene-1,2,3-trisulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC2=C1 GPUMPJNVOBTUFM-UHFFFAOYSA-N 0.000 description 6
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- YZBGUDOBFPDWKS-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)anilino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=C(OC(F)(F)F)C=C1 YZBGUDOBFPDWKS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- HKGOFWIZZIYCOS-UHFFFAOYSA-N naphthalene-2-sulfonic acid;hydrate Chemical compound O.C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 HKGOFWIZZIYCOS-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical group 0.000 description 3
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- HYFMZOAPNQAXHU-UHFFFAOYSA-N naphthalene-1,7-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(S(=O)(=O)O)=CC=C21 HYFMZOAPNQAXHU-UHFFFAOYSA-N 0.000 description 3
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- MIAUJDCQDVWHEV-UHFFFAOYSA-N benzene-1,2-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1S(O)(=O)=O MIAUJDCQDVWHEV-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- KCXKCSAUAYYDLG-UHFFFAOYSA-L dipotassium;naphthalene-2,6-disulfonate Chemical compound [K+].[K+].C1=C(S([O-])(=O)=O)C=CC2=CC(S(=O)(=O)[O-])=CC=C21 KCXKCSAUAYYDLG-UHFFFAOYSA-L 0.000 description 1
- PTEWEFISOFMTTD-UHFFFAOYSA-L disodium;naphthalene-1,2-disulfonate Chemical compound [Na+].[Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(S(=O)(=O)[O-])=CC=C21 PTEWEFISOFMTTD-UHFFFAOYSA-L 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 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
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229920000642 polymer Polymers 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
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11559787A JPS63280055A (ja) | 1987-05-12 | 1987-05-12 | ２，６−ナフタレンジスルホン酸の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11559787A JPS63280055A (ja) | 1987-05-12 | 1987-05-12 | ２，６−ナフタレンジスルホン酸の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63280055A JPS63280055A (ja) | 1988-11-17 |
| JPH0354934B2 true JPH0354934B2 (enExample) | 1991-08-21 |
Family
ID=14666558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11559787A Granted JPS63280055A (ja) | 1987-05-12 | 1987-05-12 | ２，６−ナフタレンジスルホン酸の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63280055A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108707094B (zh) * | 2018-06-27 | 2021-02-26 | 浙江龙盛化工研究有限公司 | 一种2,6-萘二磺酸的合成及提纯精制的方法 |
-
1987
- 1987-05-12 JP JP11559787A patent/JPS63280055A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63280055A (ja) | 1988-11-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0524634B1 (en) | Process for the preparation of 1,2-naphtho-quinonediazido-5-sulfonyl chloride | |
| SK8997A3 (en) | Process for the preparation of 5-amino-2,4,6-triiodine-1,3- -benzenedicarboxylic acid | |
| JPS5822118B2 (ja) | イソシアヌル酸トリアリルの製造法 | |
| JPH0354934B2 (enExample) | ||
| US5312974A (en) | Process for the production of light-colored lower alkane-sulfonic acids, more particularly methanesulfonic acid | |
| US4435576A (en) | Process for the production of 2-amino-4-methyl-benzothiazole | |
| US4352759A (en) | Recovery of high purity N-acyl taurine in high yield | |
| US2400934A (en) | Amines and purification thereof | |
| RU2130449C1 (ru) | Способ получения 3,4-дигидрокси-5-нитробензальдегида | |
| KR100789557B1 (ko) | 디메틸 테레프탈레이트 제조공정의 부산물로부터메틸-4-포밀벤조에이트와 디메틸 테레프탈레이트의분리회수방법 | |
| JPS63225351A (ja) | ２，６−ナフタレンジスルホン酸の分離方法 | |
| JP2915515B2 (ja) | Ｏ―メチルイソ尿素硫酸塩の製造方法 | |
| JP3407336B2 (ja) | アミノエタンスルホン酸類の精製方法 | |
| JP2799373B2 (ja) | アジ化ナトリウムの製造法 | |
| JPH06306042A (ja) | スルホベタインの製造方法 | |
| JPS63225352A (ja) | ２，７−ナフタレンジスルホン酸の製造方法 | |
| US4091013A (en) | Process for preparing 1-amino-naphthalene-7-sulphonic acid | |
| JP4288439B2 (ja) | ３，３’−ジフルオロ−４，４’−ジメトキシ−ベンゾフェノンの製造方法 | |
| JPH0761957A (ja) | Ｎ−混合飽和脂肪酸アシル中性アミノ酸の製造法 | |
| JPS5932461B2 (ja) | ｐ−トルエンスルホン酸クロリドの精製方法 | |
| JPH01153654A (ja) | 含フッ素カルボン酸アンモニウム塩の製造方法 | |
| JP3316917B2 (ja) | 新規フェニルアラニン塩結晶とその製造法 | |
| US3355485A (en) | Preparation of sodium cyclohexyl sulfamate free of sulfate ions | |
| JPS6081144A (ja) | α−ハロゲノ−β−フエニルプロピオン酸の製造方法 | |
| JP2770512B2 (ja) | アミノエチルスルホン酸アルカリ金属塩類の精製方法 |