FR2491923A1 - Procede pour produire du sulfochlorure de chlorobenzene - Google Patents
Procede pour produire du sulfochlorure de chlorobenzene Download PDFInfo
- Publication number
- FR2491923A1 FR2491923A1 FR8119353A FR8119353A FR2491923A1 FR 2491923 A1 FR2491923 A1 FR 2491923A1 FR 8119353 A FR8119353 A FR 8119353A FR 8119353 A FR8119353 A FR 8119353A FR 2491923 A1 FR2491923 A1 FR 2491923A1
- Authority
- FR
- France
- Prior art keywords
- chlorobenzene
- sulfochloride
- acid
- sulfuric acid
- layer
- 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.)
- Granted
Links
- JESCPVSKEGXYSC-UHFFFAOYSA-N chlorobenzene;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.ClC1=CC=CC=C1 JESCPVSKEGXYSC-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 238000000034 method Methods 0.000 title claims abstract description 40
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 210
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 111
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 72
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims abstract description 64
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 5
- 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 47
- 238000000926 separation method Methods 0.000 claims description 19
- 238000005406 washing Methods 0.000 claims description 19
- 239000002244 precipitate Substances 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000002351 wastewater Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 244000309466 calf Species 0.000 claims 1
- 229960004265 piperacetazine Drugs 0.000 claims 1
- 239000007788 liquid Substances 0.000 abstract description 7
- 238000002360 preparation method Methods 0.000 abstract description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- 239000007795 chemical reaction product Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 14
- 239000007791 liquid phase Substances 0.000 description 11
- -1 chloro- Chemical class 0.000 description 10
- URCLXLVQHAJFSJ-UHFFFAOYSA-N chlorosulfonyl hypochlorite Chemical compound ClOS(Cl)(=O)=O URCLXLVQHAJFSJ-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- MNURPFVONZPVLA-UHFFFAOYSA-N 2-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1Cl MNURPFVONZPVLA-UHFFFAOYSA-N 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- CELCMWUXMBTJRP-UHFFFAOYSA-N chlorobenzene;hydrochloride Chemical compound Cl.ClC1=CC=CC=C1 CELCMWUXMBTJRP-UHFFFAOYSA-N 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
- 239000012456 homogeneous solution Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-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
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 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
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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 (2)
| Publication Number | Publication Date |
|---|---|
| FR2491923A1 true FR2491923A1 (fr) | 1982-04-16 |
| FR2491923B1 FR2491923B1 (enExample) | 1985-03-15 |
Family
ID=27302799
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8119353A Granted FR2491923A1 (fr) | 1980-10-14 | 1981-10-14 | Procede pour produire du sulfochlorure de chlorobenzene |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE3140854A1 (enExample) |
| FR (1) | FR2491923A1 (enExample) |
| GB (1) | GB2087386B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3302647A1 (de) * | 1983-01-27 | 1984-08-02 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von 4-chlorphenylsulfonylverbindungen |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3108137A (en) * | 1959-08-31 | 1963-10-22 | Chemetron Corp | Production of organic sulfonyl chlorides |
| DE1468136A1 (de) * | 1962-02-19 | 1970-03-19 | Koninklijke Zwavelzuurfabrieken v/h Ketjen N.V., Amsterdam | Verfahren zur Herstellung von Benzol- und Toluolsulfosäurechloriden |
| DE1950395A1 (de) * | 1968-10-07 | 1970-04-16 | Chris Craft Ind Inc | Verfahren zur Herstellung von Arylsulfonylchloriden |
-
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
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3108137A (en) * | 1959-08-31 | 1963-10-22 | Chemetron Corp | Production of organic sulfonyl chlorides |
| DE1468136A1 (de) * | 1962-02-19 | 1970-03-19 | Koninklijke Zwavelzuurfabrieken v/h Ketjen N.V., Amsterdam | Verfahren zur Herstellung von Benzol- und Toluolsulfosäurechloriden |
| DE1950395A1 (de) * | 1968-10-07 | 1970-04-16 | Chris Craft Ind Inc | Verfahren zur Herstellung von Arylsulfonylchloriden |
Non-Patent Citations (1)
| Title |
|---|
| Chemical Abstracts vol. 84, no. 3, 19 janvier 1976Columbus, Ohio, USA page 429, colonne 1, abrégé no. 16958p & JP-A-75-100035 (Cat. D) * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3140854A1 (de) | 1982-05-27 |
| FR2491923B1 (enExample) | 1985-03-15 |
| GB2087386A (en) | 1982-05-26 |
| GB2087386B (en) | 1984-09-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |