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ChemicalBook CAS DataBase List Irganox 3052
61167-58-6

Irganox 3052 synthesis

2synthesis methods
To a 2-liter four-necked flask equipped with a thermometer, stirring apparatus, condenser and dropping funnel were added 340.51 g (1.0 mol) of 2,2'-methylenebis(6-tert-butyl-4-methylphenol), 72.06 g (1.0 mol) of acrylic acid, 500 g of toluene and 209.47 g (2.07 mol) of triethylamine. After replacing the air in the container with nitrogen, 105.8 g (0.69 mol) of phosphorus oxychloride was added dropwise with stirring. After completion of the dropwise addition, the reaction solution was kept at 80 ℃. for 1 hour. After that, the organic layer was washed with water until it became neutral, and toluene was removed under reduced pressure. The residue was then recrystallized from n-hexane to obtain 374.8 g of a white crystalline 2,2'-methylenebis(6-tert-butyl-4-methylphenol) monoacrylate (Irganox 3052) having a melting point of 132 to 134 ℃. Yield, 95%.
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Yield:61167-58-6 95%

Reaction Conditions:

with triethylamine in nitrogen;toluene;

Steps:

C.1 COMPARATIVE EXAMPLE 1

To a 500-ml four-necked flask equipped with a thermometer, stirring apparatus, condenser and dropping funnel were added 82.0 g (0.241 mole) of 2,2'-methylenebis(6-tert-butyl-4-methylphenol), 200 g of toluene and 23.9 g (0.290 mole) of triethylamine. After replacing the air in the container with nitrogen, 25 g (0.276 mole) of acryloyl chloride was added dropwise with stirring. After completion of the dropwise addition, stirring was continued for 1 hour, excess triethylamine was neutralized with a dilute hydrochloric acid and the formed triethylamine hydrochloride was then removed by washing with water. Toluene was then removed by evaporation from the toluene layer after completion of the washing, and the residue obtained was recrystallized from 20 g of n-hexane to obtain 90.0 g of 2,2'-methylenebis(6-tert-butyl-4-methylphenol) monoacrylate as a white crystal. Melting point, 132°-134° C. Yield, 95%. The yield of the product based on acrylic acid was 37.1%.

References:

US4562281,1985,A

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