80-07-9

Basic information

• Product Name: 4,4'-Dichlorodiphenyl sulfone
• Synonyms: 1,1’-sulfonylbis[4-chloro-benzene];1-Chloro-4-[(4-chlorophenyl)sulfonyl]benzene;4,4'-Dichlorophenyl sulfone;Benzene, 1,1'-sulfonylbis*4-chloro-;Benzene, 1,1'-sulfonylbis[4-chloro-;di-p-chlorophenylsulfone;p,p’-dichlorodiphenylsulfone;p,p'-Dichlorodiphenyl sulfone
• CAS NO: 80-07-9
• Molecular Formula: C₁₂H₈Cl₂O₂S
• Molecular Weight: 287.16
• EINECS: 201-247-9
• Product Categories: Sulphur Derivatives;Organics;Diphenyl Sulfones (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;Imidazoles
• Mol File: 80-07-9.mol
• Article Data: 71

Chemical Properties

• Melting Point: 143-146 °C(lit.)
• Boiling Point: 250 °C10 mm Hg(lit.)
• Flash Point: 233 °C
• Appearance: White/Fine Powder
• Density: 1.54g/cm3
• Vapor Pressure: 7.18E-07mmHg at 25°C
• Refractive Index: 1.61
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility: <0.1 g/100 mL at 20℃
• Sensitive: Moisture Sensitive
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• BRN: 2052955
• CAS DataBase Reference: 4,4'-Dichlorodiphenyl sulfone(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Dichlorodiphenyl sulfone(80-07-9)
• EPA Substance Registry System: 4,4'-Dichlorodiphenyl sulfone(80-07-9)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26
• WGK Germany: 2
• RTECS: WR3450000
• TSCA: Yes
• Hazardous Substances Data: 80-07-9(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 80-07-9 differently. You can refer to the following data:
1. 4,4’Dichlorodiphenyl Sulfone is an impurity of Dapson (D193250), an antibacterial used in the treatment of dermatitis herpetiformis.
2. Bis(4-chlorophenyl) sulfone is used as a precursor to prepare 4,4'-diamino-diphenyl sulfone and polysulfone plastics. It is also used to prepare rigid and temperature resistant polymers such as PES or Udel through polymerization with bisphenol-A and bisphenol-S. Further, the udel polymer finds applications in plumbing pipes, printer cartridges and automobile fuses.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

4,4'-Dichlorodiphenyl sulfone is incompatible with strong oxidizers.

Fire Hazard

Flash point data for 4,4'-Dichlorodiphenyl sulfone are not available; however, 4,4'-Dichlorodiphenyl sulfone is probably combustible.

Flammability and Explosibility

Nonflammable

Safety Profile

Mildly toxic by ingestion. When heated to decomposition it emitsvery toxic fumes of Cl- and SOx.

InChI:InChI=1/C12H8Cl2O2S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8H

Synthetic route

chlorobenzene (108-90-7) → 4,4'-dichlorodiphenyl sulphone (80-07-9)

Conditions	Yield
With sulfuric acid; trifluoroacetic acid; trifluoroacetic anhydride; Η-β Zeochem at 10 - 53℃; for 4h; Product distribution / selectivity;	100%
With sulfuric acid at 20℃; for 4h;	95.02%
Stage #1: chlorobenzene With aluminum (III) chloride; thionyl chloride In water at 50 - 90℃; for 3h; Stage #2: With sulfuric acid; dihydrogen peroxide; acetic acid In water at 80℃; for 3h;	93.8%

bis(4-chlorophenyl)sulfoxide (3085-42-5) → 4,4'-dichlorodiphenyl sulphone (80-07-9)

Conditions	Yield
With dihydrogen peroxide; acetic acid at 80℃; for 2h;	99.3%
With tetrabutyl-ammonium chloride; dihydrogen peroxide In water at 95℃; for 5h; Temperature; Reagent/catalyst;	97.8%
With N-(n-butyl)tridemorph phosphotungstate; dihydrogen peroxide In benzene at 90℃; for 2h; Catalytic behavior; Temperature;	96.2%

4-chlorobenzenesulfonyl chloride (98-60-2) + chlorobenzene (108-90-7) → 4,4'-dichlorodiphenyl sulphone (80-07-9)

Conditions	Yield
iron(III) chloride at 144℃; for 0.333333h; microwave irradiation;	95%
With iron(III) chloride at 100 - 120℃;
With aluminium trichloride
With iron(III) chloride at 100 - 120℃;

sodium p-chlorobenzenesulphinate (14752-66-0) → 4,4'-dichlorodiphenyl sulphone (80-07-9)

Conditions	Yield
With copper diacetate In acetonitrile at 60℃; for 3h;	94%

para-dichlorobenzene (106-46-7) → 4,4'-dichlorodiphenyl sulphone (80-07-9)

Conditions	Yield
With aluminum (III) chloride; thionyl chloride at 20℃; for 3h; Temperature;	94%

bis(4-chlorophenyl)sulfide (5181-10-2) → 4,4'-dichlorodiphenyl sulphone (80-07-9)

Conditions	Yield
With sodium bromate In water at 80℃; for 0.5h; Ionic liquid;	92%
With palladium; dihydrogen peroxide In methanol at 100℃; for 6h; Green chemistry; chemoselective reaction;	90%
With dihydrogen peroxide In methanol at 40℃; for 1.58333h; chemoselective reaction;	89%

p-chlorobenzenesulfonyl azide (4547-68-6) + chlorobenzene (108-90-7) → 4,4'-dichlorodiphenyl sulphone (80-07-9)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at 25℃; for 3h; regiospecific reaction;	81%

bis(4-chlorophenyl)sulfoxide (3085-42-5) → bis(4-chlorophenyl)sulfide (5181-10-2) + 4,4'-dichlorodiphenyl sulphone (80-07-9)

Conditions	Yield
With [ReOCl3(PPh3)2] In ethanol for 18h; Reflux;	A 33% B 65%
With phenyltrifluorodiazoethane; oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane; acetonitrile at 20℃; for 0.5h; Irradiation;

sodium p-chlorobenzenesulphinate (14752-66-0) + bis(4-chlorophenyl)iodonium bromide (26018-88-2) → 4,4'-dichlorodiphenyl sulphone (80-07-9)

Conditions	Yield
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 40℃;	62%

sodium p-chlorobenzenesulphinate (14752-66-0) + bis(4-chlorophenyl)iodonium tetrafluoroborate → 4,4'-dichlorodiphenyl sulphone (80-07-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 50℃; for 4h;	55%

chlorobenzene (108-90-7) → 4,4'-dichlorodiphenyl sulphone (80-07-9) + 1-chloro-2-(4-chlorophenylsulfonyl)benzene (38980-51-7)

Conditions	Yield
With cadmium(II) sulfate crystallohydrate; phosphorus pentoxide at 20℃; for 5h; Milling; Sealed tube; Green chemistry;	A 53% B 14%
With sulfur trioxide; dimethyl sulfate at 50℃; for 1.33333h; exclusion of air humidity;

bromochlorobenzene (106-39-8) → 4,4'-dichlorodiphenyl sulphone (80-07-9)

Conditions	Yield
With potassium pyrosulfite; palladium diacetate; N-ethyl-N,N-diisopropylamine; tri tert-butylphosphoniumtetrafluoroborate In N,N-dimethyl-formamide at 100℃; for 20h; Inert atmosphere;	19%

4-chloro-benzenesulfonic acid (98-66-8) + chlorobenzene (108-90-7) → 4,4'-dichlorodiphenyl sulphone (80-07-9)

Conditions	Yield
With sulfur trioxide; trifluoroacetic acid at 40 - 100℃; for 8.5h; Product distribution / selectivity; Inert atmosphere;	11%
With acetic anhydride at 100 - 120℃; for 3h; Product distribution / selectivity;	2%
unter kontinuierlicher Entfernung des gebildeten Wassers;

methyl p-chlorobenzenesulphonate (15481-45-5) → 4,4'-dichlorodiphenyl sulphone (80-07-9)

Conditions	Yield
With sulfur trioxide anschliessendes Erwaermen mit Chlorbenzol;

chlorobenzene (108-90-7) → 4,4'-dichlorodiphenyl sulphone (80-07-9) + 4-chlorobenzenesulfonyl chloride (98-60-2)

Conditions	Yield
With chlorosulfonic acid
With chlorosulfonic acid at 25℃;
With chlorosulfonic acid; sulfuric acid Edukt 4:SO3;

bis(4-chlorophenyl)sulfide (5181-10-2) → bis(4-chlorophenyl)sulfoxide (3085-42-5) + 4,4'-dichlorodiphenyl sulphone (80-07-9)

Conditions	Yield
With 1-oxo-10-tert-butyl-3,3,7,7-tetrakis(trifluoromethyl)-4,6-benzo-1-ioda-2,8-dioxabicyclo<3.3.0>octane at 130℃; for 24h; other substrates;

chlorobenzene (108-90-7) → 4,4'-dichlorodiphenyl sulphone (80-07-9) + bis(2-chlorophenyl) sulfone (5097-15-4) + 1-chloro-2-(4-chlorophenylsulfonyl)benzene (38980-51-7)

Conditions	Yield
With antimony pentafluoride; fluorosulphonic acid at 50℃; for 1h; Yield given. Yields of byproduct given;

chlorobenzene (108-90-7) → 4,4'-dichlorodiphenyl sulphone (80-07-9) + p-chlorobenzenesulfonic anhydride (14248-65-8)

Conditions	Yield
With sulfur trioxide	A 6 % Chromat. B n/a

aluminium trichloride (7446-70-0) + 4-chlorobenzenesulfonyl chloride (98-60-2) + chlorobenzene (108-90-7) → 4,4'-dichlorodiphenyl sulphone (80-07-9)

chlorosulfonic acid (7790-94-5) + chlorobenzene (108-90-7) → 4,4'-dichlorodiphenyl sulphone (80-07-9) + 4-chloro-benzenesulfonic acid (98-66-8) + 4-chlorobenzenesulfonyl chloride (98-60-2)

Conditions	Yield
at -5℃; auch bei Zusatz von wasserfreier Schwefelsaeure;

<4-chloro-phenyl>-<4-amino-phenyl>-sulfone acetate → 4,4'-dichlorodiphenyl sulphone (80-07-9)

Conditions	Yield
With sulfuric acid; acetic acid; sodium nitrite Behandeln der erhaltenen Diazoniumsalz-Loesung mit einer Loesung von CuCl in konz. wss. HCl;

chlorobenzene (108-90-7) + p-chloro-benzenesulfonic acid chloride → 4,4'-dichlorodiphenyl sulphone (80-07-9)

Conditions	Yield
With aluminium trichloride

disulfuric acid (7783-05-3) + chlorobenzene (108-90-7) → 4,4'-dichlorodiphenyl sulphone (80-07-9) + 4-chloro-benzenesulfonic acid (98-66-8)

Conditions	Yield
With sulfuric acid

4-chlorobenzenesulfonyl chloride (98-60-2) + chlorobenzene (108-90-7) → 4,4'-dichlorodiphenyl sulphone (80-07-9) + 1-chloro-2-(4-chlorophenylsulfonyl)benzene (38980-51-7)

Conditions	Yield
iron(III) chloride at 144℃; for 0.333333h; Product distribution / selectivity; Irradiation;

5-p-(p-chlorophenylsulphonyl)phenyl-3-mercapto-1,2,4-triazole (141212-57-9) → 4-Chlorophenyl phenyl sulfone (80-00-2) + phenyl p-chlorophenyl sulfide (13343-26-5) + 4,4'-dichlorodiphenyl sulphone (80-07-9) + 1-(4-chlorophenylsulfonyl)-4-cyanobenzene (80988-11-0)

Conditions	Yield
at 475℃; under 2 Torr; Pyrolysis; Inert atmosphere;	A 12.1 %Chromat. B 6 %Chromat. C 3.9 %Chromat. D 60.6 %Chromat.

5-p-(p-chlorophenylsulphonyl)phenyl-3-mercapto-1,2,4-triazole (141212-57-9) → 4-Chlorophenyl phenyl sulfone (80-00-2) + 4,4'-dichlorodiphenyl sulphone (80-07-9) + 4-((4- chlorophenyl) thio) benzo nitrile (96461-81-3) + 1-(4-chlorophenylsulfonyl)-4-cyanobenzene (80988-11-0)

Conditions	Yield
at 750℃; under 2 Torr; Pyrolysis; Inert atmosphere;	A 16 %Chromat. B 4 %Chromat. C 5 %Chromat. D 40.2 %Chromat.

5-p-(p-chlorophenylsulphonyl)phenyl-3-mercapto-1,2,4-triazole (141212-57-9) → 4-Chlorophenyl phenyl sulfone (80-00-2) + 4,4'-dichlorodiphenyl sulphone (80-07-9) + 1-(4-chlorophenylsulfonyl)-4-cyanobenzene (80988-11-0)

Conditions	Yield
at 550℃; under 2 Torr; Pyrolysis; Inert atmosphere;	A 10.4 %Chromat. B 3.8 %Chromat. C 56 %Chromat.

4,4'-sulfonediphenol (80-09-1) → 4,4'-dichlorodiphenyl sulphone (80-07-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water / 2 h / Reflux 1.2: 50 °C / pH 10.85 2.1: sulfuric acid / water / pH 5 View Scheme

Monosodium salt of 4,4'-dihydroxydiphenylsulfone → 4,4'-dichlorodiphenyl sulphone (80-07-9)

Conditions	Yield
With sulfuric acid In water pH=5;

chlorine-terminated poly(ethylene oxide) + 4,4'-Dihydroxybiphenyl (92-88-6) + 4,4'-dichlorodiphenyl sulphone (80-07-9) → polysulfone-block-poly(ethylene oxide), Mn = 56000 (GPC), Mw = 67000 (GPC), polydispersity = 1.9 (GPC); monomer(s): chlorine-terminated poly(ethylene oxide); 4,4'-dichlorodiphenyl sulfone; 4,4'-dihydroxybiphenyl

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide; toluene at 160℃; for 20h;	100%

4,4'-dichlorodiphenyl sulphone (80-07-9) → bis(4-chloro-3-nitrophenyl)sulfone (1759-05-3)

Conditions	Yield
With sulfuric acid; nitric acid In 1,2-dichloro-ethane	99%
With sodium nitrate; sulfuric acid at 80℃;	95%
With sulfuric acid; nitric acid In water at 20℃; for 6h;	92%

4,4'-dichlorodiphenyl sulphone (80-07-9) + 2-hydroxyethanethiol (60-24-2) → 2,2’-((sulfonylbis(4,1-phenylene))bis(sulfanediyl))bis(ethan-1-ol) (53680-66-3)

Conditions	Yield
With potassium carbonate In ISOPROPYLAMIDE at 150℃; for 5h;	98%
With sodium hydride In 1-methyl-pyrrolidin-2-one at 10 - 50℃; for 2h;	90%

4,4'-dichlorodiphenyl sulphone (80-07-9) + trimethyltin(IV)chloride (1066-45-1) → 4,4'-sulfonylbis(4,1-phenylene)bis(trimethylstannane)

Conditions	Yield
Stage #1: 4,4'-dichlorodiphenyl sulphone With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃;	97%

4,4'-dichlorodiphenyl sulphone (80-07-9) + phenylboronic acid (98-80-6) → 4,4''-sulfonyldi-1,1'-biphenyl (19942-80-4)

Conditions	Yield
With palladium diacetate; 1,3-bis-(diphenylphosphino)propane; cesium fluoride In various solvent(s) at 100℃; for 10h;	95%

4,4'-dichlorodiphenyl sulphone (80-07-9) + (p-hydroxyphenyl)boronic acid (71597-85-8) → 4,4'-bis(4-hydroxyphenyl)diphenyl sulfone (170275-06-6)

Conditions	Yield
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; for 20h;	95%

2,6-di-tert-butylphenol (128-39-2) + 4,4'-dichlorodiphenyl sulphone (80-07-9) → 4'-<(4-Chlorophenyl)sulfonyl>-3,5-di-tert-butyl-<1,1'-biphenyl>-4-ol (139225-66-4)

Conditions	Yield
With 2,3-diethynylquinoxaline; potassium tert-butylate; ammonia at -40℃; electrolysis, current density 1.5 A*dm-2;	90%
With 2,3-diethynylquinoxaline; potassium tert-butylate In ammonia at -38℃; electrosynthesis: cathode - platinum grid, 10 cm2, 1024 mesh/cm2; anode - magnesium rod, h = 8 cm, Φ = 1 cm; constant current density 0,5 A dm2, KBr as supporting electrolyte;	90%

4,4'-dichlorodiphenyl sulphone (80-07-9) + sodium thiophenolate (930-69-8) → C24H18O2S3 (93103-32-3)

Conditions	Yield
1-(2'-ethylhexyl)-4-dimethylaminopyridinium chloride In 1,2-dichloro-benzene at 150℃; for 2h;	90%

4,4'-dichlorodiphenyl sulphone (80-07-9) → 4,4'-dihydrazinodiphenyl sulfone (14052-65-4)

Conditions	Yield
With hydrazine hydrate; triethylamine for 20h; Heating;	90%
With hydrazine hydrate; triethylamine for 24h; Reflux;	90%

4,4'-dichlorodiphenyl sulphone (80-07-9) + 2-Mercaptobenzothiazole (149-30-4) → 4,4'-di(2-benzothiazolylthio)diphenyl sulfone (1334840-69-5)

Conditions	Yield
With sodium hydride In 1-methyl-pyrrolidin-2-one at 10 - 150℃; for 13h;	90%

3,5-dimethoxyphenol (500-99-2) + 4,4'-dichlorodiphenyl sulphone (80-07-9) → 4,4'-bis(3,5-dimethoxyphenoxy)diphenyl sulfone

Conditions	Yield
Stage #1: 3,5-dimethoxyphenol; 4,4'-dichlorodiphenyl sulphone With potassium carbonate In N,N-dimethyl acetamide; toluene at 140℃; for 4h; Dean-Stark; Inert atmosphere; Stage #2: In N,N-dimethyl-formamide at 150℃; for 1h; Dean-Stark; Inert atmosphere;	90%
With N,N-dimethyl acetamide; potassium carbonate In toluene at 150℃; for 15h; Temperature; Inert atmosphere; Reflux;

4,4'-dichlorodiphenyl sulphone (80-07-9) + ortho-cresol (95-48-7) → 4,4'-bis(2-methylphenyloxy)diphenylsulfone (53895-55-9)

Conditions	Yield
	92%

4,4'-dichlorodiphenyl sulphone (80-07-9) → dapsone (80-08-0)

Conditions	Yield
With ammonium chloride In ethanol for 5h; Reflux;	91.9%
With ammonia; water; copper; copper(I) bromide at 200℃;
With ammonia; copper(II) sulfate; ethylene glycol at 245℃;

4,4'-dichlorodiphenyl sulphone (80-07-9) + 4-tert-butylphenylboronic acid (123324-71-0) → bis(4'-t-butylbiphenyl-4-yl)sulfone

Conditions	Yield
With sodium phosphate In water; isopropyl alcohol at 85℃; for 2h; Suzuki-Miyaura Coupling;	90%

4,4'-dichlorodiphenyl sulphone (80-07-9) + sodium phenoxide (139-02-6) → 4,4'-sulfonylbis(phenoxybenzene) (1623-91-2)

Conditions	Yield
N-2-ethylhexyl chloride of 4(4-methylpiperidinyl)pyridine In 1,2-dichloro-benzene at 180℃; for 2h;	87%

(9,9’-(5-(4,4,5,5-tetramethyl-1,2,3-dioxaborolan-2-yl)-1,3-phenylene)bis(9H-carbazole)) (1082549-89-0) + 4,4'-dichlorodiphenyl sulphone (80-07-9) → 9,9' ,9'' ,9''' -(sulfonylbis([1,1' -biphenyl]-4',3,5-triyl))tetrakis(9H-carbazole)

Conditions	Yield
Stage #1: (9,9’-(5-(4,4,5,5-tetramethyl-1,2,3-dioxaborolan-2-yl)-1,3-phenylene)bis(9H-carbazole)); 4,4'-dichlorodiphenyl sulphone With Aliquat 336; potassium carbonate In water; toluene for 0.25h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In water; toluene at 130℃; for 12h; Inert atmosphere;	86%

4,4'-dichlorodiphenyl sulphone (80-07-9) + 2,5-Dimercapto-1,3,4-thiadiazole (1072-71-5) → C16H10N4O2S7

Conditions	Yield
With potassium carbonate at 180℃; for 18h; Temperature; Reagent/catalyst; Inert atmosphere;	85.1%

4,4'-dichlorodiphenyl sulphone (80-07-9) + N1,N1,N3,N3-tetraphenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,3-diamine → 4' ,4"' -sulfonylbis(N3,N3,N5,N5-tetraphenyl-[1,1' -biphenyl]-3,5-diamine)

Conditions	Yield
Stage #1: 4,4'-dichlorodiphenyl sulphone; N1,N1,N3,N3-tetraphenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,3-diamine With Aliquat 336; potassium carbonate In water; toluene for 0.25h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In water; toluene at 130℃; for 12h; Inert atmosphere;	85%
Stage #1: 4,4'-dichlorodiphenyl sulphone; N1,N1,N3,N3-tetraphenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,3-diamine With Aliquat 336; potassium carbonate In water; toluene for 0.25h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In water; toluene at 130℃; for 12h; Inert atmosphere;	85%

4,4'-dichlorodiphenyl sulphone (80-07-9) → disodium 4,4'-dichlorodiphenylsulfone-3,3'-disulfonate

Conditions	Yield
With sulfuric acid; sulfur trioxide at 75 - 160℃; for 4.5h; Large scale;	83%
Stage #1: 4,4'-dichlorodiphenyl sulphone With fuming sulphuric acid at 110℃; for 6h; Stage #2: With sodium chloride In water
Stage #1: 4,4'-dichlorodiphenyl sulphone With sulfuric acid; sulfur trioxide Stage #2: With sodium chloride

4,4'-dichlorodiphenyl sulphone (80-07-9) + 1-phenyl-2-bromoethane (103-63-9) → 4,4'-sulfonylbis(1-phenylethyl)benzene

Conditions	Yield
With 2.9-dimethyl-1,10-phenanthroline; nickel(II) perchlorate hexahydrate; tetrabutylammomium bromide In N,N-dimethyl acetamide at 20℃; for 10h; Glovebox; Sealed tube; Electrochemical reaction; Inert atmosphere; regioselective reaction;	83%

1,2,2,6,6-pentamethyl-piperidin-4-ol (2403-89-6) + 4,4'-dichlorodiphenyl sulphone (80-07-9) → 4,4’-((sulfonylbis(4,1-phenylene))bis(oxy))bis(1,2,2,6,6-pentamethylpiperidine)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran for 72h; Reflux; Inert atmosphere;	81.8%

4,4'-dichlorodiphenyl sulphone (80-07-9) + (S)-[1,1']-binaphthalenyl-2,2'-diol (18531-99-2) → C44H28Cl2O6S2

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 9h;	80%

Upstream product

• 5181-10-2 bis(4-chlorophenyl)sulfide 
• 3085-42-5 bis(4-chlorophenyl)sulfoxide 
• 7446-70-0 aluminium trichloride 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 108-90-7 chlorobenzene 
• 7790-94-5 chlorosulfonic acid 
• 7783-05-3 disulfuric acid 
• 14752-66-0 sodium p-chlorobenzenesulphinate 
• 26018-88-2 bis(4-chlorophenyl)iodonium bromide 
• 80-09-1 4,4'-sulfonediphenol 
• 10506-59-9 dimethyl disulfate 
• 98-66-8 4-chloro-benzenesulfonic acid 
• 4547-68-6 p-chlorobenzenesulfonyl azide 
• 106-39-8 bromochlorobenzene 

Downstream Products

• 7324-96-1 4,4'-di(methylamino)diphenyl sulfone 
• 139225-66-4 4'-<(4-Chlorophenyl)sulfonyl>-3,5-di-tert-butyl-<1,1'-biphenyl>-4-ol 
• 87014-31-1 4-(2,2,2-Trifluoroethoxy)phenyl 4-chlorophenyl sulfone 
• 87014-32-2 Bis sulfone 
• 1623-91-2 4,4'-sulfonylbis(phenoxybenzene) 
• 93103-32-3 C₂₄H₁₈O₂S₃ 
• 14052-65-4 4,4'-dihydrazinodiphenyl sulfone 
• 7402-67-7 4-(4-chloro-benzenesulfonyl)-phenol 
• 80-09-1 4,4'-sulfonediphenol 
• 50637-26-8 methyl 3-(benzyloxy)-5-methoxybenzoate 
• 197242-32-3 bis[p-[3-(benzyloxy)-5-carbomethoxyphenoxy]phenyl] sulfone 
• 98-66-8 4-chloro-benzenesulfonic acid 
• 106-46-7 para-dichlorobenzene 
• 80-00-2 4-Chlorophenyl phenyl sulfone 

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A practical and mild method for the switchable synthesis of sulfoxides or sulfonesviaselective oxidation of sulfides using cheapN-fluorobenzenesulfonimide (NFSI) as the oxidant has been developed. These highly chemoselective transformations were simply achieved by varying the NFSI loading with H2O as the green solvent and oxygen source without any additives. The good functional group tolerance makes the strategy valuable.

PROCESS FOR PRODUCING 4,4'-DICHLORODIPHENYL SULFONE

The invention relates to a process for producing 4,4'-dichlorodiphenyl sulfone comprising reacting a solution comprising 4,4'-dichlorodiphenyl sulfoxide and at least one linear C6-C10 carboxylic acid as solvent with an oxidizing agent to obtain a crude reaction product comprising 4,4'- dichlorodiphenyl sulfone, wherein the concentration of water in the reaction mixture is kept below 5 wt%, the process comprising: (a) adding 0.9 to 1.05 mol oxidizing agent per mol 4,4'-dichlorodiphenyl sulfoxide uniformly distributed to the solution at a temperature in the range from 80 to 105 °C over a period from 1.5 to 5 h in a first step to obtain the reaction mixture; (b) agitating the reaction mixture after completion of the first step at the temperature of the first step for 5 to 30 min without adding oxidizing agent; (c) adding 0.05 to 0.2 mol oxidizing agent per mol 4,4'-dichlorodiphenyl sulfoxide to the reaction mixture at a temperature in the range from 80 to 105 °C over a period of less than 40 min in a second step; (d) agitating the reaction mixture after completion of the second step at the temperature of the second step for 10 to 30 min without adding oxidizing agent, (e) heating the reaction mixture to a temperature in the range from 95 to 110°C and hold this temperature for 10 to 90 min to obtain a crude reaction product comprising 4,4'- dichlorodiphenyl sulfone.

(C)CRYSTAL COMPOSITION (CC) COMPRISING 4,4'-DICHLORODIPHENYLSULFONE CRYSTALS (C)

The invention relates to crystals (C) consisting of at least 98 % by weight of 4,4'- dichlorodiphenylsulfone, 0 to 2 % by weight of impurities and 0 to 2 % by weight of at least one solvent (c). Moreover, the present invention relates to a crystal composition (CC) comprising crystals (C) and a process for the production of the crystal composition (CC) and the crystals (C).