2,6-Di-tert-butylphenol


2,6-Di-tert-butylphenol is an organic compound with the structural formula 2,6-2C6H3OH. 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:
In this way, approximately 2.5M kg/y are produced.

Applications

Its dominant use is as an antioxidant.
2,6-di-tert-butylphenol is a precursor to more complex compounds used as antioxidants and light-protection agents for the stabilization for polymers. Of particular note is methyl-3--propionate, which is formed by the Michael addition of methyl methacrylate. This compound is used as a feedstock in the synthesis of more complex antioxidants such as Irganox 1098. 2,6-Di-tert-butylphenol is also used in the synthesis of CGP-7930, probucol, and nicanartine.

Safety and regulation

The is 9200 mg/kg, indicating a low toxicity.
2,6-Di-tert-butylphenol is covered by the U.S. Department of Transportation Code of Federal Regulations 49 CFR 172.101, Appendix B. This substance is designated by the U.S. Department of Transportation as a marine pollutant.