CH634044A5 - Process for preparing naphthalene-1,3,6-trisulphonic acid - Google Patents
Process for preparing naphthalene-1,3,6-trisulphonic acid Download PDFInfo
- Publication number
- CH634044A5 CH634044A5 CH425978A CH425978A CH634044A5 CH 634044 A5 CH634044 A5 CH 634044A5 CH 425978 A CH425978 A CH 425978A CH 425978 A CH425978 A CH 425978A CH 634044 A5 CH634044 A5 CH 634044A5
- Authority
- CH
- Switzerland
- Prior art keywords
- naphthalene
- acid
- oleum
- sulfuric acid
- weight
- Prior art date
Links
- 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 title claims description 31
- 238000004519 manufacturing process Methods 0.000 title description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 92
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 39
- 239000011541 reaction mixture Substances 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 description 20
- 238000006277 sulfonation reaction Methods 0.000 description 18
- 239000000203 mixture Substances 0.000 description 13
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 13
- 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 10
- 150000007513 acids Chemical class 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- FEWNRIKJXAQRJJ-UHFFFAOYSA-N naphthalene-1,3,7-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(S(=O)(=O)O)=CC=C21 FEWNRIKJXAQRJJ-UHFFFAOYSA-N 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 4
- SITVNOOPPBSYNB-UHFFFAOYSA-N naphthalene-1,3,5,7-tetrasulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(S(=O)(=O)O)=CC(S(O)(=O)=O)=C21 SITVNOOPPBSYNB-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- GPUMPJNVOBTUFM-UHFFFAOYSA-N naphthalene-1,2,3-trisulfonic acid Chemical class 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 3
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical class C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 3
- INMHJULHWVWVFN-UHFFFAOYSA-N naphthalene-1,3,5-trisulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(S(=O)(=O)O)=CC(S(O)(=O)=O)=C21 INMHJULHWVWVFN-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 2
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- -1 naphthalene-1 Chemical compound 0.000 description 1
- 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 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2718207A DE2718207C3 (de) | 1977-04-23 | 1977-04-23 | Verfahren zur Herstellung von Naphthalin-1,3,6-trisulfonsäure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH634044A5 true CH634044A5 (en) | 1983-01-14 |
Family
ID=6007133
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH425978A CH634044A5 (en) | 1977-04-23 | 1978-04-20 | Process for preparing naphthalene-1,3,6-trisulphonic acid |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS53132548A (it) |
| BE (1) | BE866223A (it) |
| BR (1) | BR7802456A (it) |
| CH (1) | CH634044A5 (it) |
| DE (1) | DE2718207C3 (it) |
| FR (1) | FR2387947A1 (it) |
| GB (1) | GB1596897A (it) |
| IT (1) | IT1104816B (it) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2853337A1 (de) * | 1978-12-09 | 1980-06-26 | Bayer Ag | Neue sulfierungsprodukte des naphthalins, verfahren zu ihrer herstellung und verwendung |
| DE2901178A1 (de) * | 1979-01-13 | 1980-07-24 | Bayer Ag | Verfahren zur herstellung von naphthalin-1,3,5-trisulfonsaeure |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5649908B2 (it) * | 1973-12-28 | 1981-11-25 |
-
1977
- 1977-04-23 DE DE2718207A patent/DE2718207C3/de not_active Expired
-
1978
- 1978-04-18 GB GB15194/78A patent/GB1596897A/en not_active Expired
- 1978-04-20 CH CH425978A patent/CH634044A5/de not_active IP Right Cessation
- 1978-04-20 BR BR7802456A patent/BR7802456A/pt unknown
- 1978-04-21 IT IT49013/78A patent/IT1104816B/it active
- 1978-04-21 BE BE2056897A patent/BE866223A/xx not_active IP Right Cessation
- 1978-04-21 FR FR7811944A patent/FR2387947A1/fr not_active Withdrawn
- 1978-04-21 JP JP4674078A patent/JPS53132548A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS53132548A (en) | 1978-11-18 |
| IT1104816B (it) | 1985-10-28 |
| JPS5645909B2 (it) | 1981-10-29 |
| DE2718207C3 (de) | 1981-11-05 |
| DE2718207A1 (de) | 1978-11-02 |
| BR7802456A (pt) | 1979-04-03 |
| DE2718207B2 (de) | 1980-09-11 |
| GB1596897A (en) | 1981-09-03 |
| BE866223A (fr) | 1978-10-23 |
| IT7849013A0 (it) | 1978-04-21 |
| FR2387947A1 (fr) | 1978-11-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |