Application
One important application of 3-(3, 5-tert-butyl-4-hydroxyphenyl) propionic acid is in the synthesis of antioxidant. Most widespread stabilizers of phenolic structure are derivatives of a methyl ester 3-(3’,5’-di-tert.buyil-4’-hylroxyphenyl)-propionic acid, productions which are based on ester exchanges polyatomic alcohols. To the most significant is pentaeritril-tetrakis-3-(3’,5’-di-tert.buyil-4’- hylroxyphenyl)-propionate.
From the beginning of works on synthesis of derivatives of a methyl ester 3-(3’,5’-di-tert.buyil-4’-hylroxyphenyl)- propionic acid on the present are executed a series of basic researches on catalysis and technology.
And in the present work 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-propionic acid can be used as antioxidant group to modify esters. This kind of esters is useful in many fields, such as lubricating oil and cutting compound, because of two important functions (antioxidant and lubricant) in the same compound.
Safely
The toxicity of 3-(3,5-di-tert-butyl-4- hydroxyphenyl)propanoic acid, esters with C13-C15 branched and linear alcohols has been tested by EFSA. And this scientific opinion of EFSA deals with the risk assessment of the additive, 3-(3,5-di-tert-butyl-4- hydroxyphenyl)propanoic acid, esters with C13-C15 branched and linear alcohols, CAS No. 171090- 93-0, REF. No. 47060 for which the CEF Panel concluded that there is no safety concern for the consumer if the substance is used only in polyolefins in contact with foods other than fatty/highalcoholic and dairy products and its migration does not exceed 0.05 mg/kg food.
Uses
It is employed as an active pharmaceutical intermediate.
Synthesis
Under nitrogen protection, 117 g (0.4 mol) of methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate and 126.6 g of anhydrous methanol were added to the reactor and heated to reflux. Subsequently, 120 mL of 30% aqueous NaOH solution was added slowly dropwise and the reaction was kept for 2 hours. Upon completion of the reaction, 80 ml of 10 wt% HCl solution was added for neutralization, stirred and cooled to room temperature. The reaction mixture was filtered and the filter cake was washed with deionized water to neutral. Finally, the filter cake was dried at 110 °C for 4 h to give 115 g of the white solid product 3,5-di-tert-butyl-4-hydroxybenzenepropanoic acid (A1).
References
[1] Patent: US4713475, 1987, A
[2] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1982, vol. 31, # 7, p. 1417 - 1420
[3] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1982, # 7, p. 1594 - 1597
[4] Patent: CN104211616, 2016, B. Location in patent: Paragraph 0064-0066
