1,1,1-Tris(4-hydroxyphenyl)ethane Chemical Properties

Melting point:

246-248 °C (lit.)

Boiling point:

531.8±45.0 °C(Predicted)

Density 

1.252±0.06 g/cm3(Predicted)

vapor pressure 

0Pa at 25℃

storage temp. 

Sealed in dry,Room Temperature

solubility 

241 in mg/100g standard fat at 20 ℃

form 

powder to crystal

pka

10.02±0.10(Predicted)

color 

White to Almost white

Water Solubility 

25.1mg/L at 20℃

InChI

InChI=1S/C20H18O3/c1-20(14-2-8-17(21)9-3-14,15-4-10-18(22)11-5-15)16-6-12-19(23)13-7-16/h2-13,21-23H,1H3

InChIKey

BRPSWMCDEYMRPE-UHFFFAOYSA-N

SMILES

C(C1=CC=C(O)C=C1)(C1=CC=C(O)C=C1)(C1=CC=C(O)C=C1)C

LogP

3.88 at 20℃

CAS DataBase Reference

27955-94-8(CAS DataBase Reference)

EPA Substance Registry System

Phenol, 4,4',4''-ethylidynetris- (27955-94-8)

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

36/37/38-51/53

Safety Statements 

26-37/39-61

RIDADR 

UN 3077 9/PG 3

WGK Germany 

2

RTECS 

SL4375275

HazardClass 

9

PackingGroup 

III

HS Code 

2907290030

MSDS

• Language:English Provider:SigmaAldrich

1,1,1-Tris(4-hydroxyphenyl)ethane Usage And Synthesis

Application

In polycarbonate synthesis, 1,1,1-Tris(4-hydroxyphenyl)ethane functions as a highly effective branching agent that can be incorporated into reaction mixtures containing dihydroxyaromatic compounds such as bisphenol A and carbonate sources including phosgene or diphenyl carbonate. This application has proven particularly valuable in the production of high-performance engineering polymers where enhanced mechanical strength and thermal resistance are critical requirements.

Hazard

Low toxicity by ingestion and skin contact. A mild eye irritant.

Flammability and Explosibility

Non flammable

Synthesis

Synthesis: Phenol (54.0 mol) and zinc chloride (100 g) were added to the reactor and stirred until well mixed. Subsequently, p-hydroxyacetophenone (6.5 mol) was slowly added over 40 minutes, warmed to 60°C and maintained at this temperature for 60 minutes. Concentrated hydrochloric acid (100 mL) was added and the reaction was continued with stirring for 8 hours. After completion of the reaction, the temperature was lowered to 20 °C, dichloroethane was added and filtered with thorough stirring. The filter cake was dried under vacuum at 55 °C for 6 h. The crude product 1,1,1-tris(4-hydroxyphenyl)ethane (THPE) was obtained as 1811 g. The purity of the crude product was 95.0% and the yield was 91.1%. Purification method: the crude product (1000 g) prepared above was added into methanol (2000 mL), heated until completely dissolved and then cooled, slowly added into water (1600 mL), stirred at room temperature for 50 minutes, a light yellow product was obtained. Filtered and dried. The dried product was dissolved in methanol (1200 mL), heated to complete dissolution and added activated carbon to decolorize, filtered and evaporated the solvent to obtain a solid. The obtained solid was dissolved in methanol (1000 mL), and a mixed solution of sodium borohydride (5 g) and sodium sulfite (35 g) was slowly added, and the light yellow powder gradually precipitated. The solid obtained was filtered and dried under vacuum at 25 °C for 10 h. The purified product was obtained as 913 g in 91.3% yield and 99.5% purity by HPLC analysis.

References

[1] Patent: CN105541561, 2016, A. Location in patent: Paragraph 0021; 0022; 0023; 0024; 0025
[2] Asian Journal of Chemistry, 2014, vol. 26, # 22, p. 7846 - 7852
[3] Patent: US2006/4214, 2006, A1. Location in patent: Page/Page column 4-5

1,1,1-Tris(4-hydroxyphenyl)ethane(27955-94-8)Related Product Information

• ETHYLENE OXIDE
• Triphenylmethyl Chloride
• Ethanol
• Triphenyltin acetate
• Tricine
• Triphenylphosphine
• 1,2-Dichloroethane
• Lactulose
• BUFFER SOLUTION PH = 6,00 (20 °C) (POTASSIUM DIHYDROGEN PHOSPHATE/SODIUM HYDROXIDE)
• BIS-Tris
• Dichloroethane
• CHLOROETHANE
• 2,3,5-Triphenyltetrazolium chloride
• Tris(hydroxymethyl)aminomethane
• Propiophenone
• Phenylacetone
• 1,1,1-TRIS(4-TRIFLUOROVINYLOXYPHENYL)ETHANE
• 3A-AMINO-3A-DEOXY-(2AS,3AS)-BETA-CYCLODEXTRIN