2,6-Di-tert-butylphenol

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2,6-Di-tert-butylphenol
2,6-di-tert-butylphenol.png
Identifiers
CAS number 128-39-2 YesY
ChemSpider 29135 YesY
ChEMBL CHEMBL281071 YesY
Jmol-3D images Image 1
Properties
Appearance Low-melting colourless solid
Melting point 34-36 °C
Boiling point 253 °C
Hazards
R-phrases R22 R36 R37 R38
S-phrases S22 S36
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

2,6-Di-tert-butylphenol is an organic compound with the structural formula 2,6-((CH3)3C)2C6H3OH. This colourless solid alkylated phenol and its derivatives are used industrially as UV stabilizer and an antioxidant for hydrocarbon-based products ranging from petrochemicals to plastics. Illustrative of its usefulness, it prevents gumming in aviation fuels.

Production[edit]

2,6-Di-tert-butylphenol is prepared by the reaction of phenol with isobutene catalysed by aluminium phenoxide: [1]

C6H5OH + 2 CH2=C(CH3)2 → ((CH3)3C)2C6H3OH

In this way, approximately 2.5M kg/y are produced.

Applications[edit]

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[edit]

The LD50 is 9200, indicating a low toxicity.[1]

Miscellaneous Regulations

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. Listed Name(s): 2,6-Di-tert-butylphenol.

See also[edit]

References[edit]

  1. ^ a b Helmut Fiege, Heinz-Werner Voges, Toshikazu Hamamoto, Sumio Umemura, Tadao Iwata, Hisaya Miki, Yasuhiro Fujita, Hans-Josef Buysch, Dorothea Garbe, Wilfried Paulus "Phenol Derivatives" Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a19_313 Article Online Posting Date: June 15, 2000.