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Firstly, 2,4-dimethyl-6-tert-butylphenol is reacted with formaldehyde and HCl (Blanc reaction) to generate a chloromethyl group in the less hindered meta position. This intermediate then reacts with cyanuric acid to give the desired product.
Tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate is a chemical compound used as a polymer stabilizer in plastics. Like other hindered phenols it acts as a primary antioxidant. More than 1000 tonnes per year are used in the EU.
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Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate is significantly less volatile than simpler phenolic antioxidants such as butylhydroxytoluene (BHT). This makes it more suitable to stabilising plastics, as it is not driven out by the high temperatures experienced during plastic extrusion and moulding, [2] when they are heated to 150-320 °C (300–600 °F). [3]
The effect of the tert-butyl group on the progress of a chemical reaction is called the Thorpe–Ingold effect illustrated in the Diels-Alder reaction below. Compared to a hydrogen substituent, the tert-butyl substituent accelerates the reaction rate by a factor of 240. [2] tert-Butyl effect. The tert-butyl effect is an example of steric hindrance.
705 mg mL −1: Melting point: −122 to −120 °C; −188 to −184 °F; 151 to 153 K Boiling point: ... 3-Methylheptane is a branched alkane isomeric to octane.
The chemical synthesis of BHT in industry has involved the reaction of p-cresol (4-methylphenol) with isobutylene (2-methylpropene), catalyzed by sulfuric acid: [11] CH 3 (C 6 H 4)OH + 2 CH 2 =C(CH 3) 2 → ((CH 3) 3 C) 2 CH 3 C 6 H 2 OH. Alternatively, BHT has been prepared from 2,6-di-tert-butylphenol by hydroxymethylation or aminomethylation ...
Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate - an inexpensive and commonly used polymer stabiliser; Tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate - a polymer stabiliser commonly used to protect against long term heat aging; Irganox 1098 - a polymer stabiliser with metal chelation properties