DE2635852C2 - Verfahren zur Herstellung von 4,4'- Diaminostilben-2,2'-disulfonsäure oder ihrer Na- oder K-Salze - Google Patents
Verfahren zur Herstellung von 4,4'- Diaminostilben-2,2'-disulfonsäure oder ihrer Na- oder K-SalzeInfo
- Publication number
- DE2635852C2 DE2635852C2 DE19762635852 DE2635852A DE2635852C2 DE 2635852 C2 DE2635852 C2 DE 2635852C2 DE 19762635852 DE19762635852 DE 19762635852 DE 2635852 A DE2635852 A DE 2635852A DE 2635852 C2 DE2635852 C2 DE 2635852C2
- Authority
- DE
- Germany
- Prior art keywords
- hydrogenation
- salt
- hydrogen
- salts
- dna
- 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 25
- 238000000034 method Methods 0.000 title claims description 12
- 229910052708 sodium Inorganic materials 0.000 title claims description 7
- REJHVSOVQBJEBF-OWOJBTEDSA-N 5-azaniumyl-2-[(e)-2-(4-azaniumyl-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-OWOJBTEDSA-N 0.000 title claims description 3
- REJHVSOVQBJEBF-UHFFFAOYSA-N DSD-acid Natural products OS(=O)(=O)C1=CC(N)=CC=C1C=CC1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-UHFFFAOYSA-N 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 18
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 18
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 13
- 239000007868 Raney catalyst Substances 0.000 claims description 8
- UETHPMGVZHBAFB-OWOJBTEDSA-N 4,4'-dinitro-trans-stilbene-2,2'-disulfonic acid Chemical compound OS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1\C=C\C1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O UETHPMGVZHBAFB-OWOJBTEDSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- UEUIKXVPXLWUDU-UHFFFAOYSA-N 4-diazoniobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C([N+]#N)C=C1 UEUIKXVPXLWUDU-UHFFFAOYSA-N 0.000 description 8
- 229910045601 alloy Inorganic materials 0.000 description 7
- 239000000956 alloy Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004811 liquid chromatography Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 229910000510 noble metal Inorganic materials 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- -1 DNS salt Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/46—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9752075A JPS5223053A (en) | 1975-08-13 | 1975-08-13 | Preparation of 4,4'-diaminostilbene- 2,2'-disulfonic acid and its salt s |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2635852A1 DE2635852A1 (de) | 1977-02-24 |
| DE2635852C2 true DE2635852C2 (de) | 1986-09-18 |
Family
ID=14194522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762635852 Expired DE2635852C2 (de) | 1975-08-13 | 1976-08-10 | Verfahren zur Herstellung von 4,4'- Diaminostilben-2,2'-disulfonsäure oder ihrer Na- oder K-Salze |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5223053A (OSRAM) |
| CH (1) | CH615416A5 (OSRAM) |
| DE (1) | DE2635852C2 (OSRAM) |
| FR (1) | FR2320941A1 (OSRAM) |
| GB (1) | GB1501070A (OSRAM) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2455394B2 (de) * | 1973-12-03 | 1977-06-02 | Sumitomo Chemical Co., Ltd., Osaka (Japan) | Verfahren zur herstellung von dinatrium-4,4'-diaminostilben-2,2'-disulfonat |
-
1975
- 1975-08-13 JP JP9752075A patent/JPS5223053A/ja active Granted
-
1976
- 1976-08-10 DE DE19762635852 patent/DE2635852C2/de not_active Expired
- 1976-08-11 GB GB3168576A patent/GB1501070A/en not_active Expired
- 1976-08-12 FR FR7624655A patent/FR2320941A1/fr active Granted
- 1976-08-12 CH CH1030876A patent/CH615416A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2320941A1 (fr) | 1977-03-11 |
| GB1501070A (en) | 1978-02-15 |
| DE2635852A1 (de) | 1977-02-24 |
| JPS5238031B2 (OSRAM) | 1977-09-27 |
| FR2320941B1 (OSRAM) | 1979-09-28 |
| CH615416A5 (en) | 1980-01-31 |
| JPS5223053A (en) | 1977-02-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: TUERK, D., DIPL.-CHEM. DR.RER.NAT. GILLE, C., DIPL |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |