DE2019527A1 - Herstellung aromatischer Sulfonate - Google Patents
Herstellung aromatischer SulfonateInfo
- Publication number
- DE2019527A1 DE2019527A1 DE19702019527 DE2019527A DE2019527A1 DE 2019527 A1 DE2019527 A1 DE 2019527A1 DE 19702019527 DE19702019527 DE 19702019527 DE 2019527 A DE2019527 A DE 2019527A DE 2019527 A1 DE2019527 A1 DE 2019527A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- product
- sulfur trioxide
- toluene
- amino
- 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.)
- Pending
Links
- -1 aromatic sulfonates Chemical class 0.000 title claims description 31
- 238000004519 manufacturing process Methods 0.000 title description 3
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 58
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 50
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 239000007788 liquid Substances 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 235000011007 phosphoric acid Nutrition 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- 239000000047 product Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 150000003457 sulfones Chemical class 0.000 description 14
- 239000007795 chemical reaction product Substances 0.000 description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 7
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 3
- 235000011130 ammonium sulphate Nutrition 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000006277 sulfonation reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005696 Diammonium phosphate Substances 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- QZXSMBBFBXPQHI-UHFFFAOYSA-N N-(dodecanoyl)ethanolamine Chemical compound CCCCCCCCCCCC(=O)NCCO QZXSMBBFBXPQHI-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000005228 aryl sulfonate group Chemical group 0.000 description 2
- IHRIVUSMZMVANI-UHFFFAOYSA-N azane;2-methylbenzenesulfonic acid Chemical compound [NH4+].CC1=CC=CC=C1S([O-])(=O)=O IHRIVUSMZMVANI-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 2
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 2
- 235000019838 diammonium phosphate Nutrition 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000003752 hydrotrope Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- DOBIZWYVJFIYOV-UHFFFAOYSA-N 7-hydroxynaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(O)=CC=C21 DOBIZWYVJFIYOV-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000003275 alpha amino acid group Chemical group 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- BZSRURRHUIUVTL-UHFFFAOYSA-N azane;sulfuric acid;toluene Chemical compound N.N.OS(O)(=O)=O.CC1=CC=CC=C1 BZSRURRHUIUVTL-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- UNXNGGMLCSMSLH-UHFFFAOYSA-N dihydrogen phosphate;triethylazanium Chemical compound OP(O)(O)=O.CCN(CC)CC UNXNGGMLCSMSLH-UHFFFAOYSA-N 0.000 description 1
- OXVXWUDYARFPLN-UHFFFAOYSA-N ethylazanium;hydron;sulfate Chemical compound CC[NH3+].OS([O-])(=O)=O OXVXWUDYARFPLN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2133069 | 1969-04-25 | ||
| GB5258169 | 1969-10-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2019527A1 true DE2019527A1 (de) | 1970-11-12 |
Family
ID=26255274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702019527 Pending DE2019527A1 (de) | 1969-04-25 | 1970-04-22 | Herstellung aromatischer Sulfonate |
Country Status (5)
| Country | Link |
|---|---|
| AU (1) | AU1415670A (enrdf_load_stackoverflow) |
| BE (1) | BE749505A (enrdf_load_stackoverflow) |
| DE (1) | DE2019527A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2046504A5 (enrdf_load_stackoverflow) |
| NL (1) | NL7005559A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2353918A1 (de) * | 1972-10-30 | 1974-05-02 | Adolf Dr Phil Koebner | Verfahren zur herstellung von aromatischen sulfonsaeuren |
-
1970
- 1970-04-17 NL NL7005559A patent/NL7005559A/xx not_active Application Discontinuation
- 1970-04-22 DE DE19702019527 patent/DE2019527A1/de active Pending
- 1970-04-22 AU AU14156/70A patent/AU1415670A/en not_active Expired
- 1970-04-24 FR FR7015126A patent/FR2046504A5/fr not_active Expired
- 1970-04-24 BE BE749505D patent/BE749505A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2353918A1 (de) * | 1972-10-30 | 1974-05-02 | Adolf Dr Phil Koebner | Verfahren zur herstellung von aromatischen sulfonsaeuren |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2046504A5 (en) | 1971-03-05 |
| AU1415670A (en) | 1971-10-28 |
| BE749505A (fr) | 1970-10-01 |
| NL7005559A (enrdf_load_stackoverflow) | 1970-10-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0053220B1 (de) | Verfahren zur Herstellung elektrolytarmer sulfonsäuregruppenhaltiger Verbindungen | |
| DE2736408A1 (de) | Verfahren zur herstellung von sulfobetainen | |
| DE1014989B (de) | Verfahren zur Herstellung von aromatischen Dithiophosphinsaeuren bzw. deren Salzen | |
| EP0163318B1 (de) | Neue 2-substituierte 3-Sulfopropyl-ammoniumbetaine und Verfahren zu ihrer Herstellung | |
| DE2019527A1 (de) | Herstellung aromatischer Sulfonate | |
| EP0018541B2 (de) | Verfahren zur Herstellung von 4-Nitrotoluol-2-sulfonsäure | |
| DE1964619A1 (de) | Adiabatisches Verfahren zur Herstellung von 2,4-Dichlor-6-amino-s-triazinen | |
| DE767071C (de) | Verfahren zur Herstellung von Kondensationserzeugnissen | |
| EP0041631B1 (de) | Verfahren zur Herstellung von Nitronaphthalin-sulfonsäuren | |
| DE69707008T2 (de) | Synthese von jodpropargylcarbamat in wässriger lösung | |
| EP0179223A1 (de) | Verfahren zur Herstellung stabilisierter substituierter Diperoxybernsteinsäuren | |
| DE2305517C3 (de) | 2-Imino-13-dithiacyclobutane, Verfahren zu ihrer Herstellung und sie enthaltende Warmblüterschutzmittel gegen Schildzecken | |
| DE3128007C2 (de) | Verfahren zur selektiven Seitenkettenchlorierung von mono- und polyalkylaromatischen Kohlenwasserstoffen | |
| EP0575852B1 (de) | Verfahren zur Herstellung von Dinitro-polyalkylenbenzolen | |
| DE69929453T2 (de) | Zur sulfonierung von perhalogenierten sulfanilid verwendbare verfahren und reagenz zur sulfonierung | |
| DE944623C (de) | Zusatzmittel fuer technische OEle und Fette auf Minerlaoelbasis | |
| EP0156769B1 (de) | Verfahren zur Herstellung von Nitrodiphenyldisulfiden | |
| DE1171907B (de) | Verfahren zur Herstellung aliphatischer bzw. cycloaliphatischer Sulfonamide | |
| DE1251304B (de) | Verfahren zur Herstellung von a [0 0 Dialkyl-mono- bzw -ditniophosphoryl] - carbonsäureamiden | |
| DE2019250A1 (de) | Herstellung aromatischer Sulfonate | |
| DE2124057A1 (de) | Verfahren zur Herstellung von Arensulfonsäureanhydriden | |
| EP0300275A2 (de) | Verfahren zur Herstellung von Aminoaryl-sulfonsäuren | |
| CH620424A5 (enrdf_load_stackoverflow) | ||
| DE2601146C3 (de) | Verfahren zur Herstellung von Hydrochinon | |
| DE584142C (de) | Verfahren zur Herstellung von Carbonsaeureamiden |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHW | Rejection |