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2,6-Di-tert-butylphenol

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
C14H22O
Molar mass 206.329 g·mol−1
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 GHS07: HarmfulGHS09: Environmental hazard
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.[1] 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.[2]

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-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate (CAS# 6386-38-5), 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 LD50 is 9200 mg/kg, indicating a low toxicity.[2]

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

References

  1. ^ Peter P. Klemchuk (2005). "Antioxidants". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_091.
  2. ^ a b Helmut Fiege, Heinz-Werner Voges, Toshikazu Hamamoto, Sumio Umemura, Tadao Iwata, Hisaya Miki, Yasuhiro Fujita, Hans-Josef Buysch, Dorothea Garbe, Wilfried Paulus (2002). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313.CS1 maint: multiple names: authors list (link)