2,6-Di-tert-butylphenol
chemical compound
2,6-Di-tert-butylphenol is an organic compound with the structural formula 2,6-((CH3)3C)2C6H3OH. 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. Illustrative of its usefulness, it prevents gumming in aviation fuels.
Production
2,6-Di-tert-butylphenol is prepared industrially via the Friedel–Crafts alkylation of phenol with isobutene catalyzed by aluminium phenoxide:
C6H5OH + 2 CH2=C(CH3)2 → ((CH3)3C)2C6H3OH
In this way, approximately 2.5M kg/y are produced. Alkylation of phenol usually favours the para-position, and a strong lewis acid such as the Al3+ ion is necessary to give selective ortho‑alkylation. If a conventional brønsted acid is used then 2,4-di-tert-butylphenol will be produced instead.
Natural occurrence
Two species of plants, Jastropa curcas and Metaplexis japonica, contain 2,6-DTBP in seeds.
Applications
Its dominant use is as an antioxidant.
2,6-Di-tert-butylphenol is used in the synthesis of 4,4′-biphenol. The process involves oxidative coupling of followed by removal of the tert-butyl groups.
2,6-di-tert-butylphenol is a precursor to antioxidants and light-protection agents for the stabilization for polymers.
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