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2,6-Di-tert-butylphenol

Dibutylphenol 2,6-Bis(tert-butyl)phenol 2,6-Di(1,1-dimethylethyl)phenol 2,6-DTBP Ethanox 701 Ethyl 701 Ethyl AN 701 Irganox L 140 Isonox 103 TK 12891

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. One such case is methyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate (CAS# 6386-38-5), which is formed by the Michael addition of methyl acrylate. This compound is used 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 (20 Dec 2004). This substance is designated by the U.S. Department of Transportation (DOT) as a marine pollutant.

References

References

  1. Peter P. Klemchuk. (2005). "Antioxidants".
  2. Helmut Fiege. (2002). "Phenol Derivatives".
  3. (June 1957). "The ortho-Alkylation of Phenols 1". The Journal of Organic Chemistry.
  4. (June 2004). "A new mechanism — key for an improved synthesis of 2,6-di-tert-butylphenol". Applied Catalysis A: General.
  5. (6 January 2020). "Natural Sources and Bioactivities of 2,4-Di-Tert-Butylphenol and Its Analogs.". Toxins.
  6. (2002). "Phenol Derivatives". Wiley-VCH.
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antioxidants alkylphenols fuel-antioxidants tert-butyl-compounds
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