GB1572916A - Process for production of 4,4'-dichlorodiphenyl sulphone - Google Patents
Process for production of 4,4'-dichlorodiphenyl sulphone Download PDFInfo
- Publication number
- GB1572916A GB1572916A GB444377A GB444377A GB1572916A GB 1572916 A GB1572916 A GB 1572916A GB 444377 A GB444377 A GB 444377A GB 444377 A GB444377 A GB 444377A GB 1572916 A GB1572916 A GB 1572916A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulfone
- reaction
- monochlorobenzene
- per cent
- product
- 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 46
- 230000008569 process Effects 0.000 title claims description 43
- 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 claims description 19
- 238000004519 manufacturing process Methods 0.000 title description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 49
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 42
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000011541 reaction mixture Substances 0.000 claims description 22
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 18
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 18
- 150000003457 sulfones Chemical class 0.000 claims description 17
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 12
- 230000003197 catalytic effect Effects 0.000 claims description 9
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical class ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 claims description 9
- 238000010992 reflux Methods 0.000 claims description 7
- 238000011084 recovery Methods 0.000 claims description 6
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 238000004458 analytical method Methods 0.000 claims description 4
- 239000012452 mother liquor Substances 0.000 claims description 4
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- IBRQUKZZBXZOBA-UHFFFAOYSA-N 1-chloro-3-(3-chlorophenyl)sulfonylbenzene Chemical compound ClC1=CC=CC(S(=O)(=O)C=2C=C(Cl)C=CC=2)=C1 IBRQUKZZBXZOBA-UHFFFAOYSA-N 0.000 claims description 2
- 238000005259 measurement Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000007789 gas Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000007086 side reaction Methods 0.000 description 5
- 229910006124 SOCl2 Inorganic materials 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 2
- NNTJKSMVNWGFTB-UHFFFAOYSA-N disulfuryl chloride Chemical compound ClS(=O)(=O)OS(Cl)(=O)=O NNTJKSMVNWGFTB-UHFFFAOYSA-N 0.000 description 2
- -1 monochloro - Thionyl Sulfur benzene Chloride Chemical compound 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- BTJCWHLRIYOGHC-UHFFFAOYSA-N ClC1=CC=CC=C1.C1(=CC=CC=C1)S(=O)(=O)C1=CC=CC=C1 Chemical compound ClC1=CC=CC=C1.C1(=CC=CC=C1)S(=O)(=O)C1=CC=CC=C1 BTJCWHLRIYOGHC-UHFFFAOYSA-N 0.000 description 1
- 229910015400 FeC13 Inorganic materials 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material 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
- 230000009467 reduction Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000002002 slurry Substances 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 (1)
| Publication Number | Publication Date |
|---|---|
| GB1572916A true GB1572916A (en) | 1980-08-06 |
Family
ID=24636264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB444377A Expired GB1572916A (en) | 1976-02-11 | 1977-02-03 | Process for production of 4,4'-dichlorodiphenyl sulphone |
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) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4871876A (en) * | 1987-02-17 | 1989-10-03 | Dresser Industries, Inc. | Preparation of 4,4' dichlorodiphenyl sulfone |
| US4873372A (en) * | 1987-02-17 | 1989-10-10 | Basf Aktiengesellschaft | Isolation of 4,4'-dichlorodiphenyl sulfone |
| US4937387A (en) * | 1986-09-05 | 1990-06-26 | Amoco Corporation | Processes for preparing diaryl sulfones |
| US4983773A (en) * | 1988-10-19 | 1991-01-08 | Basf Aktiengesellschaft | Preparation of bis-(4-chlorophenyl) sulfone |
| EP3441393A1 (en) | 2017-08-07 | 2019-02-13 | Rhodia Operations | New cycloadduct precursors of dihalodiphenylsulfones and preparations thereof |
Families Citing this family (8)
| 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 | ||
| 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 |
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
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4937387A (en) * | 1986-09-05 | 1990-06-26 | Amoco Corporation | Processes for preparing diaryl sulfones |
| US4871876A (en) * | 1987-02-17 | 1989-10-03 | Dresser Industries, Inc. | Preparation of 4,4' dichlorodiphenyl sulfone |
| US4873372A (en) * | 1987-02-17 | 1989-10-10 | Basf Aktiengesellschaft | Isolation of 4,4'-dichlorodiphenyl sulfone |
| US4983773A (en) * | 1988-10-19 | 1991-01-08 | Basf Aktiengesellschaft | Preparation of bis-(4-chlorophenyl) sulfone |
| EP3441393A1 (en) | 2017-08-07 | 2019-02-13 | Rhodia Operations | New cycloadduct precursors of dihalodiphenylsulfones and preparations thereof |
| WO2019030184A1 (en) | 2017-08-07 | 2019-02-14 | Rhodia Operations | NOVEL CYCLOADDITION PRECURSORS OF DIHALOGENODIPHENYLSULFONES AND PREPARATIONS THEREOF |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2704972A1 (de) | 1977-08-18 |
| FR2340929A1 (fr) | 1977-09-09 |
| JPS565386B2 (enrdf_load_stackoverflow) | 1981-02-04 |
| FR2340929B1 (enrdf_load_stackoverflow) | 1983-01-14 |
| DE2704972C2 (de) | 1985-08-22 |
| JPS52113942A (en) | 1977-09-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19970202 |