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4,4'-Sulfonyldiphenol
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Name

4,4'-Sulfonyldiphenol

 EINECS 201-250-5
CAS No. 80-09-1 Density 1.432 g/cm3
PSA 82.98000 LogP 3.01140
Solubility 1.1 g/L (20°C) in water Melting Point 245-250 °C(lit.)
Formula C12H10O4S Boiling Point 505.3 °C at 760 mmHg
Molecular Weight 250.275 Flash Point 259.4 °C
Transport Information N/A Appearance light yellow crystalline powder
Safety 26-39-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 80-09-1 (4,4'-Sulfonyldiphenol) Hazard Symbols IrritantXi
Synonyms

4-(4-hydroxyphenyl)sulfonylphenol;4,4'-Sulfonyldiphenol;

Article Data 79

4,4'-Sulfonyldiphenol Synthetic route

108-95-2

phenol

A

80-09-1

4,4'-sulfonediphenol

B

5397-34-2

2,4'-dihydroxydiphenyl sulfone

Conditions
ConditionsYield
Stage #1: phenol With sulfuric acid; benzene-1,3-disulfonic acid In 1,3,5-trimethyl-benzene at 145 - 165℃; for 5h; Heating / reflux;
Stage #2: at 170 - 185℃; under 525.053 Torr; for 2h; Product distribution / selectivity;		A 94%
B n/a
With sulfuric acid In 1,3,5-trimethyl-benzene at 145 - 165℃; for 5h; Product distribution / selectivity; Heating / reflux;A 89%
B n/a
Stage #1: phenol With sulfuric acid In 1,3,5-trimethyl-benzene at 145 - 165℃; for 5h; Heating / reflux;
Stage #2: at 170 - 185℃; under 525.053 Torr; for 2h; Product distribution / selectivity;		A 83%
B n/a
106-41-2

4-bromo-phenol

80-09-1

4,4'-sulfonediphenol

Conditions
ConditionsYield
With potassium pyrosulfite; palladium diacetate; N-ethyl-N,N-diisopropylamine; tri tert-butylphosphoniumtetrafluoroborate In N,N-dimethyl-formamide at 100℃; for 20h; Inert atmosphere;83%
2664-63-3

4,4'-Thiodiphenol

80-09-1

4,4'-sulfonediphenol

Conditions
ConditionsYield
With dihydrogen peroxide In water at 20℃; for 0.833333h; chemoselective reaction;94%
With dihydrogen peroxide In methanol at 40℃; for 0.666667h; chemoselective reaction;90%
With palladium; dihydrogen peroxide In methanol at 100℃; for 12h; Green chemistry; chemoselective reaction;87%
540-38-5

4-Iodophenol

80-09-1

4,4'-sulfonediphenol

Conditions
ConditionsYield
With potassium pyrosulfite; palladium diacetate; N-ethyl-N,N-diisopropylamine; tri tert-butylphosphoniumtetrafluoroborate In N,N-dimethyl-formamide at 100℃; for 20h; Inert atmosphere;74%
108-95-2

phenol

80-09-1

4,4'-sulfonediphenol

Conditions
ConditionsYield
With sulfuric acid In ISOPER G at 50 - 165℃; for 7h; Product distribution / selectivity; water separating duct;80%
With sulfuric acid at 100 - 110℃; Eintragen von Phenol in das Reaktionsgemisch bei 120-130grad/15-18 Torr;
With sulfuric acid
95-50-1

1,2-dichloro-benzene

108-95-2

phenol

80-09-1

4,4'-sulfonediphenol

Conditions
ConditionsYield
With sulfuric acid In chlorobenzene90%
89.5%
2664-63-3

4,4'-Thiodiphenol

A

80-09-1

4,4'-sulfonediphenol

B

1774-34-1

bis(4-hydroxyphenyl) sulfoxide

Conditions
ConditionsYield
With dihydrogen peroxide In water; acetonitrile at 30℃; for 5h;A 10%
B 60%
With dihydrogen peroxide In ethanol at 25℃; for 9.3h; Green chemistry;
With dihydrogen peroxide In methanol at 30℃; for 2h;A 6 %Chromat.
B 91 %Chromat.
7440-44-0

pyrographite

95-50-1

1,2-dichloro-benzene

108-95-2

phenol

80-09-1

4,4'-sulfonediphenol

Conditions
ConditionsYield
With sodium hydroxide; sulfuric acid In water92.6%
4-amino-5-chloro-1-phenylpyridazin-6-one (chloridazon)

4-amino-5-chloro-1-phenylpyridazin-6-one (chloridazon)

1698-53-9

4,5-dichloro-1-phenylpyridazin-6-one

A

80-09-1

4,4'-sulfonediphenol

B

1698-60-8

chloridazon

Conditions
ConditionsYield
In waterA n/a
B 91.3%
108-90-7

chlorobenzene

A

80-09-1

4,4'-sulfonediphenol

B

5397-34-2

2,4'-dihydroxydiphenyl sulfone

Conditions
ConditionsYield
Stage #1: chlorobenzene With sulfur trioxide; dimethyl sulfate at 30℃; for 2h;
Stage #2: With sodium hydroxide In water at 220℃; for 4h;

4,4'-Sulfonyldiphenol Consensus Reports

Reported in EPA TSCA Inventory.

4,4'-Sulfonyldiphenol Specification

1. Introduction of 4,4'-Sulfonyldiphenol
4,4'-Sulfonyldiphenol is commonly used as a reactant in epoxy reactions, and is used in curing fast-drying epoxy resin glues. The IUPAC Name of 4,4'-Sulfonyldiphenol is 4-(4-Hydroxyphenyl)sulfonylphenol.

2. Properties of 4,4'-Sulfonyldiphenol
H bond acceptors: 4
H bond donors: 2
Freely Rotating Bonds: 4
Polar Surface Area: 60.98 Å2
Index of Refraction: 1.645
Molar Refractivity: 63.33 cm3
Molar Volume: 174.6 cm3
Surface Tension: 60.7 dyne/cm
Density: 1.432 g/cm3
Flash Point: 259.4 °C
Enthalpy of Vaporization: 80.43 kJ/mol
Boiling Point: 505.3 °C at 760 mmHg
Vapour Pressure: 7.8E-11 mmHg at 25°C
Melting Point: 245-250 °C(lit.)
Water Solubility: 1.1 g/L (20°C)
Appearance: light yellow crystalline powder
Stability: Stable. Incompatible with strong bases, acid chloride, acid anhydrides, strong oxidizing agents. 
Product Categories of 4,4'-Sulfonyldiphenol (CAS NO.80-09-1): Aromatics;Sulphur Derivatives;API intermediates;Color Former & Related Compounds;Developer;Diphenyl Sulfones (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research

3. Structure Descriptors of 4,4'-Sulfonyldiphenol
4. Toxicity of 4,4'-Sulfonyldiphenol

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 skin > 1mg/kg (1mg/kg)   National Technical Information Service. Vol. OTS0534330,
mouse LD50 intraperitoneal 200mg/kg (200mg/kg)   National Technical Information Service. Vol. OTS0534330,
mouse LD50 oral 1600mg/kg (1600mg/kg)   National Technical Information Service. Vol. OTS0534330,
rabbit LD50 skin > 10250mg/kg (10250mg/kg)   BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 601-05501, Pg. 1974,
rabbit LDLo oral 4700mg/kg (4700mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION		 National Technical Information Service. Vol. OTS0555048,
rat LD50 intraperitoneal 400mg/kg (400mg/kg)   National Technical Information Service. Vol. OTS0534330,
rat LD50 oral 4556mg/kg (4556mg/kg)   BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 601-05501, Pg. 1974,

5. Safety Information of 4,4'-Sulfonyldiphenol

Hazard Codes: IrritantXi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-39-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing. 
S39: Wear eye / face protection.
WGK Germany: 2
RTECS: SM8925000
HS Code: 29309070
Mildly toxic by ingestion. A skin and eye irritant. When heated to decomposition it emits toxic fumes of SOx. 

6. Preparation of 4,4'-Sulfonyldiphenol
4,4'-Sulfonyldiphenol can produced by the reaction of two equivalents of phenol with one equivalent of sulfuric acid.


7. Use of  4,4'-Sulfonyldiphenol
 4,4'-Sulfonyldiphenol is mainly used as monomer for synthesizing polysulfone resin. It can be also directly applied in coatings, leather modifier, dye intermediates, metal electroplating light agent, etc.

8. Other details of 4,4'-Sulfonyldiphenol
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Dangerous fire hazard in the form of dust when exposed to heat or flame.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. 
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store in a cool, dry place. Store in a tightly closed container.

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