Chemical Properties
White powder. Odorless. Soluble in benzene, acetone, chloroform, slightly soluble in ethanol, insoluble in water.
Uses
Pentaerythritol Tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate) is an antioxidant used in food packaging to prevent the spoilage and increase the shelf life of food products. It can be found mainly in food packages made of LDPE, HDPE, PP, PVC and PET.
General Description
Pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate) (PT) is a sterically hindered phenolic antioxidant and a heat stabilizer mainly used to enhance the oxidative resistance and protection against the toxicity of solvents. It has a glass transition temperature of 50℃ and can be annealed at room temperature.
PT can be used as an additive to protect biaxially-oriented propylene (BOPP) capacitor film from thermal oxidation on UV exposure. It can also be used as a standard material to study the gas-cluster ion sputtering (GCIS) using X-ray photoelectron microscopy (XPS) and Atomic force microscopy (AFM).
Health effects
No ADME data are available for this compound. The acute oral LD50 of pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate) in rats and mice is >5000 mg/kg bw. No clinical signs were reported. For acute dermal toxicity the LD50 in rats is >3160 mg/kg bw. Slight erythema and desquamation were noted. The LC50 for inhalation toxicity in rats is >1951 mg/m3 . Ruffled fur and exophthalmus were reported until day 5 after exposure. No human data on acute toxicity are available. Based on tests with rabbits pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate) is not considered to be a skin or eye irritant. No human data are available. No sensitization potential is found in the guinea-pig in a Maurer optimisation test.
Flammability and Explosibility
Notclassified
Synthesis
Under mechanical stirring, 584 g of methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 68 g of pentaerythritol, 0.58 g of sodium montmorillonite, and 50 mL of methanol were added to a 1000 mL four-neck flask. A thermometer sleeve was installed and stirring was started. The reaction was heated to 130-140 °C via a heating jacket while nitrogen was charged and the pressure of the reaction system was controlled at 3-4 MPa. After the reaction lasted for 7 h, the reaction was cooled down to 25 °C, filtered and dried to obtain pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]. The results were analyzed by liquid chromatography as follows: the absorption peak with a retention time of 2.643 min corresponded to methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate with 0.43%; the absorption peak with a retention time of 3.29 min corresponded to pentaerythritol tris[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] with 0.69%; the absorption peak with a retention time of The absorption peak at 3.84 min corresponded to dealkylated pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] with 0.55%; the absorption peak with retention time of 4.747 min corresponded to pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] with 96.45%. The purity of pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] synthesized by this method meets the industrial standard of not less than 94%, and the yield of the product is 98%.
References
[1] Patent: CN106278894, 2017, A. Location in patent: Paragraph 0017; 0018; 0019
[2] Patent: CN106748790, 2017, A. Location in patent: Paragraph 0031; 0032; 0033; 0034; 0035; 0036; 0037-0050
[3] Russian Chemical Bulletin, 2012, vol. 61, # 9, p. 1689 - 1693
[4] Izv. Akad. Nauk, Ser. Khim., 2012, # 9, p. 1673 - 1677,5
[5] Patent: WO2005/42463, 2005, A1. Location in patent: Page/Page column 10
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