4,4'-Sulfonyldiphenol

Bezeichnung:4,4'-Sulfonyldiphenol

CAS-Nr80-09-1

Englisch Name:Bis(4-hydroxyphenyl) Sulfone

CBNumberCB4306294

SummenformelC12H10O4S

Molgewicht250.27

MOL-Datei80-09-1.mol

Synonyma

4,4'-Sulfonyldiphenol

4,4'-Sulfonyldiphenol physikalisch-chemischer Eigenschaften

Schmelzpunkt	245-250 °C (lit.)
Siedepunkt	363.4°C (rough estimate)
chüttdichte	500kg/m3
Dichte	1.366
Dampfdruck	<0.0001 Pa (20 °C)
Brechungsindex	1.5220 (estimate)
storage temp.	Store below +30°C.
Löslichkeit	1.1g/l
pka	7+-.0.15(Predicted)
Aggregatzustand	Crystalline Powder
Farbe	White to grayish-green
Geruch (Odor)	odorless
PH	6.6-7.0 (100g/l, H2O, 20℃)
Wasserlöslichkeit	1.1 g/L (20 ºC)
maximale Wellenlänge (λmax)	295nm(H2O)(lit.)
BRN	2052954
Henry's Law Constant	3.7×10⁹ mol/(m³Pa) at 25℃, HSDB (2015)
Stabilität	Stable. Incompatible with strong bases, acid chloride, acid anhydrides, strong oxidizing agents.
Major Application	cleaning products cosmetics food and beverages personal care
InChI	1S/C12H10O4S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8,13-14H
InChIKey	VPWNQTHUCYMVMZ-UHFFFAOYSA-N
SMILES	Oc1ccc(cc1)S(=O)(=O)c2ccc(O)cc2
LogP	1.2 at 23℃
CAS Datenbank	80-09-1(CAS DataBase Reference)
EPA chemische Informationen	Phenol, 4,4'-sulfonylbis- (80-09-1)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36-36/37/38
S-Sätze:	26-39-36-37
WGK Germany	2
RTECS-Nr.	SM8925000
Selbstentzündungstemperatur	>=400 °C
TSCA	TSCA listed
HS Code	29309070
Speicherklasse	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Repr. 1B
Giftige Stoffe Daten	80-09-1(Hazardous Substances Data)
Toxizität	LD50 orally in Rabbit: 2830 mg/kg

Gefahreninformationscode (GHS)

Bis(4-hydroxyphenyl) Sulfone Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36:Reizt die Augen.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S39:Schutzbrille/Gesichtsschutz tragen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
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].
Chemische Eigenschaften
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.
Verwenden
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.
Verwenden
4,4'-Sulfonyldiphenol is commonly used as a reactant in epoxy reactions and is also used as a latent thermal catalyst for epoxy resin.
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.
synthetische
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.
Allgemeine Beschreibung
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
Synthese

108-95-2

80-09-1

5397-34-2

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.
Einzelnachweise
[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 Upstream-Materialien And Downstream Produkte

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