Methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate Chemical Properties

Melting point:

60-67°C

Boiling point:

125-130 °C(Press: 0.1 Torr)

Density 

1.006±0.06 g/cm3(Predicted)

refractive index 

1.5034

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

12.17±0.40(Predicted)

color 

White to Almost white

Water Solubility 

2.2mg/L at 20℃

InChI

InChI=1S/C18H28O3/c1-17(2,3)13-10-12(8-9-15(19)21-7)11-14(16(13)20)18(4,5)6/h10-11,20H,8-9H2,1-7H3

InChIKey

PXMJCECEFTYEKE-UHFFFAOYSA-N

SMILES

C1(CCC(OC)=O)=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1

LogP

4.866 (est)

CAS DataBase Reference

6386-38-5(CAS DataBase Reference)

EPA Substance Registry System

Methyl 3,5-bis(tert-butyl)-4-hydroxyhydrocinnamate (6386-38-5)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2918290090

Methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate Usage And Synthesis

Uses

Methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate is an antioxidant that is used in polyethylene.

Definition

ChEBI: Benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, methyl ester is an alkylbenzene.

Synthesis

(1) 2,6-di-tert-butylphenol (20.6 g), zinc carbonate (mass ratio 1.5) and tributyltin acetate (0.072 g) were added to a three-necked flask fitted with a mechanical stirrer, a nitrogen introduction tube and a dropping funnel under nitrogen atmosphere. The mixture was melted under nitrogen protection and heating conditions to form a reaction system. (2) When the temperature of the reaction system rose to 70°C, methyl acrylate (8.24 g) was slowly added through a dropping funnel. After the dropwise addition was completed, the reaction was continued with stirring for 0.5 hours. The reaction temperature was then raised to 90 °C and maintained for 1 hour. After completion of the reaction, it was cooled to 80 °C and the reaction solution was adjusted to neutral with dilute hydrochloric acid to induce crystallization of the product. After filtration, methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate was obtained in 99% yield and 99.5% purity without recrystallization.

References

[1] Patent: CN108358781, 2018, A. Location in patent: Paragraph 0046-0049
[2] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1989, vol. 38, # 8.2, p. 1677 - 1682
[3] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1989, # 8, p. 1829 - 1835
[4] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1989, vol. 38, # 8.2, p. 1677 - 1682
[5] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1989, # 8, p. 1829 - 1835

Methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate(6386-38-5)Related Product Information

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