2,6-Di-tert-butylphenol

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2,6-Di-tert-butylphenol
Structural formula of 2,6-di-tert-butylphenol
Ball-and-stick model of the 2,6-di-tert-butylphenol molecule
Names
Preferred IUPAC name
2,6-Di-tert-butylphenol
Other names
2,6-Bis(1,1-dimethylethyl)phenol
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
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.441
EC Number 204-884-0
RTECS number SK8265000
UNII
UN number 2430, 3077
Properties
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)
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The environment pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word Warning
H315, H319, H400, H410
P264, P273, P280, P302+352, P305+351+338, P321, P332+313, P337+313, P362, P391, P501
Flash point 118°C
Except where otherwise noted, 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 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[edit]

2,6-Di-tert-butylphenol is prepared industrially via the Friedel–Crafts alkylation of phenol with isobutene catalyzed 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 for the stabilization for polymers. Of particular note is methyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate (CAS# 6386-38-5), which is formed by the Michael addition of methyl methacrylate. This is used as a feedstock in the synthesis of more complex antioxidants such as Irganox 1098.

Safety and regulation[edit]

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

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.

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" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a19_313 Article Online Posting Date: June 15, 2000.