| Preferred IUPAC name
| Other names
Ethyl AN 701
Irganox L 140
|3D model (Jmol)||Interactive image|
|Appearance||Low-melting colourless solid|
|Melting point||34 to 37 °C (93 to 99 °F; 307 to 310 K)|
|Boiling point||253 °C (487 °F; 526 K)|
|R-phrases||R22 R36 R37 R38|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|(what is ?)|
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.
2,6-Di-tert-butylphenol is prepared by the reaction 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.
2,6-Di-tert-butylphenol is a precursor to more complex compounds used as antioxidants and light-protection agents. Representative derivatives include 3,5-di-tert-butyl-4-hydroxybenzyl chloride (CAS# 955-01-1), 3,5-di-tert-butyl-4-hydroxybenzyl alcohol (CAS# 88-26-6), and methyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)- propionate (CAS# 6386-38-5). Such derivatives are prepared from 2,6-di-tert-butylphenol by chloromethylation and hydroxymethylation using formaldehye and alkylation with acrylic acid.
Safety and regulation
The LD50 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.
- Helmut Fiege, Heinz-Werner Voges, Toshikazu Hamamoto, Sumio Umemura, Tadao Iwata, Hisaya Miki, Yasuhiro Fujita, Hans-Josef Buysch, Dorothea Garbe, Wilfried Paulus "Phenol Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a19_313 Article Online Posting Date: June 15, 2000.