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| CAS No.: | 80-09-1 |
|---|---|
| Name: | 4,4'-Sulfonyldiphenol |
| Article Data: | 79 |
| Molecular Structure: | |
|
|
|
| Formula: | C12H10O4S |
| Molecular Weight: | 250.275 |
| Synonyms: | 4-(4-hydroxyphenyl)sulfonylphenol;4,4'-Sulfonyldiphenol; |
| EINECS: | 201-250-5 |
| Density: | 1.432 g/cm3 |
| Melting Point: | 245-250 °C(lit.) |
| Boiling Point: | 505.3 °C at 760 mmHg |
| Flash Point: | 259.4 °C |
| Solubility: | 1.1 g/L (20°C) in water |
| Appearance: | light yellow crystalline powder |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 26-39-36 |
| PSA: | 82.98000 |
| LogP: | 3.01140 |
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| Conditions | Yield |
|---|---|
| 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 |
| 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; | 83% |
| Conditions | Yield |
|---|---|
| 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% |
| 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; | 74% |
| Conditions | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| With sulfuric acid In chlorobenzene | 90% |
| 89.5% |
| Conditions | Yield |
|---|---|
| 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. |
| Conditions | Yield |
|---|---|
| With sodium hydroxide; sulfuric acid In water | 92.6% |
| Conditions | Yield |
|---|---|
| In water | A n/a B 91.3% |
| Conditions | Yield |
|---|---|
| Stage #1: chlorobenzene With sulfur trioxide; dimethyl sulfate at 30℃; for 2h; Stage #2: With sodium hydroxide In water at 220℃; for 4h; |
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Consensus Reports
Reported in EPA TSCA Inventory.
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: 
Xi
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.
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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.