DE3140854A1 - Verfahren zur herstellung von chlorbenzolsulfochlorid - Google Patents
Verfahren zur herstellung von chlorbenzolsulfochloridInfo
- Publication number
- DE3140854A1 DE3140854A1 DE19813140854 DE3140854A DE3140854A1 DE 3140854 A1 DE3140854 A1 DE 3140854A1 DE 19813140854 DE19813140854 DE 19813140854 DE 3140854 A DE3140854 A DE 3140854A DE 3140854 A1 DE3140854 A1 DE 3140854A1
- Authority
- DE
- Germany
- Prior art keywords
- sulfuric acid
- chlorobenzene
- layer
- acid
- water
- 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.)
- Withdrawn
Links
- JESCPVSKEGXYSC-UHFFFAOYSA-N chlorobenzene;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.ClC1=CC=CC=C1 JESCPVSKEGXYSC-UHFFFAOYSA-N 0.000 title claims description 32
- 238000004519 manufacturing process Methods 0.000 title claims description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 208
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 109
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 68
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 62
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 46
- 238000000354 decomposition reaction Methods 0.000 claims description 27
- KMVZDSQHLDGKGV-UHFFFAOYSA-N 2-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=CC=C1S(Cl)(=O)=O KMVZDSQHLDGKGV-UHFFFAOYSA-N 0.000 claims description 25
- 238000005406 washing Methods 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 239000002244 precipitate Substances 0.000 claims description 15
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 10
- 239000002351 wastewater Substances 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 description 31
- MNURPFVONZPVLA-UHFFFAOYSA-N 2-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1Cl MNURPFVONZPVLA-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000007791 liquid phase Substances 0.000 description 11
- 238000005191 phase separation Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 239000007787 solid Substances 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical class CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- IEYRVMPISNTHDA-UHFFFAOYSA-N 6-chloro-7-thiabicyclo[4.1.0]hepta-2,4-diene Chemical compound C1=CC=CC2(Cl)C1S2 IEYRVMPISNTHDA-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- GLLIPPRGASTLQN-UHFFFAOYSA-N Cl.OS(Cl)(=O)=O Chemical compound Cl.OS(Cl)(=O)=O GLLIPPRGASTLQN-UHFFFAOYSA-N 0.000 description 1
- 241000727274 Crocidura voi Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- -1 chlorobenzene sulfide chloride Chemical compound 0.000 description 1
- HJKYPFCCEDZASB-UHFFFAOYSA-N chlorobenzene;sulfuric acid Chemical compound OS(O)(=O)=O.ClC1=CC=CC=C1 HJKYPFCCEDZASB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229940082150 encore Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000008096 xylene Substances 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
- C07C303/08—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 halogenosulfonic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55143425A JPS5834469B2 (ja) | 1980-10-14 | 1980-10-14 | クロルベンゼンスルホクロリドの製造方法 |
| JP16074380A JPS6034946B2 (ja) | 1980-11-17 | 1980-11-17 | クロルベンゼンスルホクロリドの製造方法 |
| JP7874381A JPS6035340B2 (ja) | 1981-05-26 | 1981-05-26 | クロルベンゼンスルホクロリドの製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3140854A1 true DE3140854A1 (de) | 1982-05-27 |
Family
ID=27302799
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813140854 Withdrawn DE3140854A1 (de) | 1980-10-14 | 1981-10-14 | Verfahren zur herstellung von chlorbenzolsulfochlorid |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE3140854A1 (enExample) |
| FR (1) | FR2491923A1 (enExample) |
| GB (1) | GB2087386B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0115328A1 (de) * | 1983-01-27 | 1984-08-08 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von 4-Chlorphenylsulfonylverbindungen |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3108137A (en) * | 1959-08-31 | 1963-10-22 | Chemetron Corp | Production of organic sulfonyl chlorides |
| GB1007655A (en) * | 1962-02-19 | 1965-10-13 | Konink Zwavelzuurfabrieken V H | Process for the manufacture of organic sulphonylchlorides |
| US3632642A (en) * | 1968-10-07 | 1972-01-04 | Chris Craft Ind Inc | Production of arylsulfonyl chlorides |
-
1981
- 1981-10-06 GB GB8130118A patent/GB2087386B/en not_active Expired
- 1981-10-14 DE DE19813140854 patent/DE3140854A1/de not_active Withdrawn
- 1981-10-14 FR FR8119353A patent/FR2491923A1/fr active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0115328A1 (de) * | 1983-01-27 | 1984-08-08 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von 4-Chlorphenylsulfonylverbindungen |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2491923B1 (enExample) | 1985-03-15 |
| GB2087386A (en) | 1982-05-26 |
| FR2491923A1 (fr) | 1982-04-16 |
| GB2087386B (en) | 1984-09-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |