DE2704972C2 - Verfahren zur Herstellung von 4,4'-Dichlordiphenylsulfon - Google Patents
Verfahren zur Herstellung von 4,4'-DichlordiphenylsulfonInfo
- Publication number
- DE2704972C2 DE2704972C2 DE19772704972 DE2704972A DE2704972C2 DE 2704972 C2 DE2704972 C2 DE 2704972C2 DE 19772704972 DE19772704972 DE 19772704972 DE 2704972 A DE2704972 A DE 2704972A DE 2704972 C2 DE2704972 C2 DE 2704972C2
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- stage
- monochlorobenzene
- sulfone
- mol
- 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
- 238000000034 method Methods 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 5
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 title description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 49
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 26
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 24
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 16
- 150000003457 sulfones Chemical class 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 5
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 28
- 239000007789 gas Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- 101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 description 7
- 102100029645 UBX domain-containing protein 11 Human genes 0.000 description 7
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical class ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 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
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- -1 aromatic sulfonic acids Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 1
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000009666 routine test Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 238000005406 washing 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
- C07C303/22—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 from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65720976A | 1976-02-11 | 1976-02-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2704972A1 DE2704972A1 (de) | 1977-08-18 |
| DE2704972C2 true DE2704972C2 (de) | 1985-08-22 |
Family
ID=24636264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772704972 Expired DE2704972C2 (de) | 1976-02-11 | 1977-02-07 | Verfahren zur Herstellung von 4,4'-Dichlordiphenylsulfon |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS52113942A (enrdf_load_stackoverflow) |
| DE (1) | DE2704972C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2340929A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1572916A (enrdf_load_stackoverflow) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2967122D1 (en) * | 1979-06-15 | 1984-08-23 | Union Carbide Corp | Process for preparing 4-4'-dichlorodiphenyl sulphone |
| EP0062736B2 (en) * | 1979-06-15 | 1992-04-15 | Amoco Corporation | Process for preparing 4-4'-dichlorodiphenyl sulphone |
| JPS56131561A (en) * | 1980-03-03 | 1981-10-15 | Konishi Kagaku Kogyo Kk | Preparation of 4,4'-dichlorodiphenylsulfone |
| JPS6080683U (ja) * | 1983-11-10 | 1985-06-04 | 矢崎総業株式会社 | ヒユ−ズ付ダイオ−ドコネクタ |
| JPS62183379U (enrdf_load_stackoverflow) * | 1986-05-12 | 1987-11-20 | ||
| US4937387A (en) * | 1986-09-05 | 1990-06-26 | Amoco Corporation | Processes for preparing diaryl sulfones |
| DE3704931A1 (de) * | 1987-02-17 | 1988-08-25 | Basf Ag | Verfahren zur isolierung von 4,4'-dichlordiphenylsulfon |
| DE3704932A1 (de) * | 1987-02-17 | 1988-09-01 | Basf Ag | Verfahren zur herstellung von 4,4'-dichlordiphenylsulfon |
| DE3835562A1 (de) * | 1988-10-19 | 1990-05-03 | Basf Ag | Verfahren zur herstellung von bis-(4-chlorphenyl)-sulfon |
| US4990678A (en) * | 1989-12-08 | 1991-02-05 | Phillips Petroleum Company | Purification of halogenated aromatic sulfones or ketones |
| GB0921069D0 (en) | 2009-12-01 | 2010-01-13 | Bandodkar Hemant R | Process for the production of a sulfone polymer |
| US9212111B2 (en) * | 2011-12-15 | 2015-12-15 | Solvay Specialty Polymers Usa, Llc | Process for manufacturing haloaryl compounds from mixtures of isomers of dihalodiarylsulfone |
| EP3441393B1 (en) | 2017-08-07 | 2020-03-18 | Rhodia Operations | New cycloadduct precursors of dihalodiphenylsulfones and preparations thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2224964A (en) * | 1938-07-23 | 1940-12-17 | Gen Aniline & Film Corp | Manufacture of aromatic sulphones |
| US3334146A (en) * | 1964-08-19 | 1967-08-01 | Stauffer Chemical Co | Method for the purification of bis(4-chlorophenyl) sulfone |
| FR1523808A (fr) * | 1966-06-10 | 1968-05-03 | Union Carbide Corp | Procédé de préparation d'un mélange de sulfones et de chlorures de sulfonyle aromatiques, exempt des acides sulfoniques aromatiques et de leurs anhydrides correspondants |
| US3701806A (en) * | 1966-06-10 | 1972-10-31 | Union Carbide Corp | Process for preparing a mixture of aromatic sulfones and aromatic sulfonyl chlorides |
| US3673259A (en) * | 1968-10-07 | 1972-06-27 | Chris Craft Ind Inc | Production of aromatic sulfones |
| GB1393929A (en) * | 1972-10-16 | 1975-05-14 | Ici Ltd | Production of di-4-chlorophenyl sulphone |
| GB1351453A (en) * | 1970-02-06 | 1974-05-01 | Ici Ltd | Preparation of 4,4-dichlorodiphenyl sulphone |
| EP0062736B2 (en) * | 1979-06-15 | 1992-04-15 | Amoco Corporation | Process for preparing 4-4'-dichlorodiphenyl sulphone |
-
1977
- 1977-02-03 GB GB444377A patent/GB1572916A/en not_active Expired
- 1977-02-04 JP JP1083877A patent/JPS52113942A/ja active Granted
- 1977-02-07 DE DE19772704972 patent/DE2704972C2/de not_active Expired
- 1977-02-10 FR FR7703806A patent/FR2340929A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2704972A1 (de) | 1977-08-18 |
| FR2340929A1 (fr) | 1977-09-09 |
| GB1572916A (en) | 1980-08-06 |
| JPS565386B2 (enrdf_load_stackoverflow) | 1981-02-04 |
| FR2340929B1 (enrdf_load_stackoverflow) | 1983-01-14 |
| JPS52113942A (en) | 1977-09-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: UNION CARBIDE CORP., 06817 DANBURY, CONN., US |
|
| D2 | Grant after examination | ||
| 8363 | Opposition against the patent | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: AMOCO CORP., CHICAGO, ILL., US |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: DANNENBERG, G., DIPL.-ING., 6000 FRANKFURT WEINHOLD, P., DIPL.-CHEM. DR., 8000 MUENCHEN GUDEL, D., DR.PHIL. SCHUBERT, S., DIPL.-ING., 6000 FRANKFURT BARZ, P., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 8000 MUENCHEN |
|
| 8339 | Ceased/non-payment of the annual fee |