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4-tert-Butylphenol is an organic compound with the formula (CH 3) 3 CC 6 H 4 OH. It is one of three isomeric tert -butyl phenols . It is a white solid with a distinct phenolic odor.
The industrial synthesis of 4,4′-biphenol was developed by Allan Hay in the 1960s. [2] [3] As the direct oxidative coupling of phenol gives a mixture of isomers, [4] [5] 4,4′-biphenol is instead prepared from 2,6-di-tert-butylphenol, where para-coupling is the only possibility. [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.
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.
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 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 ...
2,4-Di-tert-butylphenol (2,4-DTBP) is a white solid with a phenolic odour. It is primarily used as a raw material for the production of several commercially important antioxidants and phenolic benzotriazole -type UV absorbers .
2,6-Di-tert-butylphenol is an organic compound with the structural formula 2,6-((CH 3) 3 C) 2 C 6 H 3 OH. This colorless solid alkylated phenol and its derivatives are used industrially as UV stabilizers and antioxidants for hydrocarbon -based products ranging from petrochemicals to plastics. [ 1 ]