Bis(4-hydroxyphenyl) Sulfone Chemical Properties

Melting point:

245-250 °C (lit.)

Boiling point:

363.4°C (rough estimate)

Density 

1.366

bulk density

500kg/m3

vapor pressure 

<0.0001 Pa (20 °C)

refractive index 

1.5220 (estimate)

storage temp. 

Store below +30°C.

solubility 

1.1g/l

form 

Crystalline Powder

pka

7?+-.0.15(Predicted)

color 

White to grayish-green

PH

6.6-7.0 (100g/l, H2O, 20℃)

Odor

odorless

Water Solubility 

1.1 g/L (20 ºC)

λmax

295nm(H2O)(lit.)

BRN 

2052954

Stability:

Stable. Incompatible with strong bases, acid chloride, acid anhydrides, strong oxidizing agents.

InChIKey

VPWNQTHUCYMVMZ-UHFFFAOYSA-N

LogP

1.2 at 23℃

CAS DataBase Reference

80-09-1(CAS DataBase Reference)

EPA Substance Registry System

Phenol, 4,4'-sulfonylbis- (80-09-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36-36/37/38

Safety Statements 

26-39-36-37

WGK Germany 

2

RTECS 

SM8925000

Autoignition Temperature

>=400 °C

TSCA 

Yes

HS Code 

29309070

Hazardous Substances Data

80-09-1(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 2830 mg/kg

MSDS

• Language:English Provider:4,4'-Dihydroxydiphenylsulfone
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Bis(4-hydroxyphenyl) Sulfone Usage And Synthesis

Description

Bisphenol S, also known as 4,4'-Sulfonyldiphenol, abbreviated as BPS, is a synthetic bisphenol (BP) compound. It was originally used as a safe alternative to bisphenol A and is present in many household products, including food packaging, beverage containers, lotions, toys, plastic PVC floors and water pipes^[1]. However, current studies have found that BPS does not seem to be very safe and may damage the function of melanocytes^[2]. Higher BPS exposure is also associated with increased serum uric acid concentrations, and this association is more obvious in boys, which poses certain health hazards^[3].

Chemical Properties

White needle-like crystals. Freely soluble in aliphatic hydrocarbons, soluble in alcohols and ethers, slightly soluble in aromatics, insoluble in water. Bisphenol S molecule contains two hydroxyl groups and a strong electron-absorbing sulfone group, so the acidity is stronger than other phenols.

Uses

4,4'-Sulfonyldiphenol is commonly used as a reactant in epoxy reactions and is also used as a latent thermal catalyst for epoxy resin.

Uses

Bis(4-hydroxyphenyl) Sulfone is commonly used as a reactant in epoxy reactions and is also used as a latent thermal catalyst for epoxy resin.

Preparation

A process for the preparation of bis(4-hydroxyphenyl)sulfone by reacting phenol with sulfuric acid in the presence of a solvent at from 130° to 220° C and in the presence or absence of a sulfonating assistant. 

Definition

ChEBI: 4,4'-sulfonyldiphenol is a sulfone that is diphenyl sulfone in which both of the para hydrogens have been replaced by hydroxy groups. It has a role as a metabolite and an endocrine disruptor. It is a sulfone and a bisphenol. It is functionally related to a diphenyl sulfone.

General Description

Bisphenol S (BPS), belonging to the class of bisphenols, is a structural analog of bisphenol A (BPA), used in a variety of industrial applications and products marketed as BPA-free. It is commonly identified in food and beverages, environmental samples, biological matrices, etc. It is also reported to be used in the production of epoxy resins. BPS is also found to be stable compared to BPA at elevated temperature and sunlight conditions.

Health Hazard

Although there is no direct link established between bis(4-hydroxyphenyl) sulfone(BPS) and cardiac disease, it is thought that bis(4-hydroxyphenyl) sulfone may operate by a similar mechanism to BPA and could cause cardiac toxicity.

Flammability and Explosibility

Non flammable

Synthesis

Under stirring conditions, 100 g (1.0 mol) of sulfuric acid at a concentration of 98% was slowly added dropwise to a mixed system containing 144 g of homotrimethylbenzene, 189 g (2.0 mol) of phenol and 11.9 g (0.05 mol) of benzene-1,3-disulfonic acid. The reaction mixture was heated in an oil bath at 200°C. As the temperature approached 145°C, the reaction mixture began to boil. The distillate was condensed by means of a condenser and separated into two phases by means of a trap. The upper organic phase is continuously returned to the reaction system. The distillation process continued for 5 hours before the temperature of the reaction mixture reached 165°C, at which time the volume of the lower aqueous phase separated by the trap stabilized at 38 mL. Crystal precipitation was observed in the reaction system, forming a slurry. A small amount of the reaction slurry was analyzed by high performance liquid chromatography (HPLC), which showed a weight ratio of 4,4'-bisphenol S (4,4'-BS), 2,4'-dihydroxydiphenylsulfone (2,4'-BS), and trihydroxytriphenyldisulfone of 96.0:3.0:1.0. Subsequently, post-processing was carried out in accordance with the method of Example 1 , resulting in 237 g of crystal product. The composition (weight ratio) of this crystal product was 4,4'-BS:2,4'-BS:trihydroxytriphenyl disulfone = 99.5:0.5:0. The yield of 4,4'-BS was 94% based on starting sulfuric acid. No sulfonic acids were detected in the crystal product, which consisted mainly of benzene-1,3-disulfonic acid and phenol sulfonic acid.

References

[1] J. APAU  Eric A  Akwasi Acheampong. Exposure to bisphenol A, bisphenol F, and bisphenol S can result in obesity in human body[J]. Cogent Chemistry, 2018. DOI:10.1080/23312009.2018.1506601.
[2] GOENKA S. Disruption of functions of primary human neonatal melanocytes cultured in the presence of bisphenol A and its analogs bisphenol F and bisphenol S[J]. Journal of hazardous materials letters, 2024, 5: Article 100110. DOI:10.1016/j.hazl.2024.100110.
[3] Y. LEE. Relationship between bisphenol A, bisphenol S, and bisphenol F and serum uric acid concentrations among school-aged children[J]. PLoS ONE, 2022. DOI:10.1371/journal.pone.0268503.

Bis(4-hydroxyphenyl) Sulfone(80-09-1)Related Product Information

• Triclosan
• 4-Cyanophenol
• 9,9-Bis(4-hydroxyphenyl)fluorene
• Bisphenol A
• Tetradifon
• 4,4'-Dichlorodiphenyl sulfone
• Diphenyl sulfone
• 4,4'-Diaminodiphenylsulfone
• Tetrabromobisphenol A
• 4,4'-Sulphonylbis(2,6-dibromophenol)
• tert-Butyl acrylate
• 4,4'-DIHYDROXYDIPHENYLMETHANE
• 3,5-Dihydroxybenzoic acid
• Phenyl sulfoxide
• 4,4'-(4,4'-ISOPROPYLIDENEDIPHENOXY)BIS(PHTHALIC ANHYDRIDE)
• 2,2'-Diamino-4,4'-sulfonyldiphenol
• Bis[4-(4-aminophenoxy)phenyl]sulfone
• BIS(4-HYDROXY-3,5-DIMETHYLPHENYL) SULFONE