2,6-Di-''tert''-butylphenol is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
with the structural formula 2,6-((CH
3)
3C)
2C
6H
3OH. This colorless solid
alkylated
phenol
Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it ...
and its derivatives are used industrially as
UV stabilizers and
antioxidants for
hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ...
-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
Aluminium phenolate is the metalloorganic compound with the formula l(OC6H5)3sub>n. It is a white solid. 27Al NMR studies suggest that aluminium phenolate exists in benzene solution as a mixture of dimer and trimer. The compound is can be pr ...
:
:C
6H
5OH + 2 CH
2=C(CH
3)
2 → ((CH
3)
3C)
2C
6H
3OH
In this way, approximately 2.5M kg/y are produced.
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
In organic chemistry, the Michael reaction or Michael addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a carbon ...
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
CGP-7930 is a compound used in scientific research which acts as a positive allosteric modulator at the GABAB receptor. It has anxiolytic effects in animal studies, and has a synergistic effect with GABAB agonists such as baclofen and GHB, as w ...
,
probucol
Probucol, sold under the trade name Lorelco among others, is an anti- hyperlipidemic drug initially developed for the treatment of coronary artery disease. Clinical development was discontinued after it was found that the drug may have the undesi ...
, 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.
]
See also
* Butylated hydroxytoluene
* 2,4-Dimethyl-6-''tert''-butylphenol
* Para tertiary butyl phenol
4-''tert''-Butylphenol is an organic compound with the formula (CH3)3CC6H4OH. It is one of three isomeric ''tert''-butyl phenols. It is a white solid with a distinct phenolic odor. It dissolves in basic water.
Manufacture
It can be prepared ...
References
{{DEFAULTSORT:Di-tert-butylphenol, 2,6-
Antioxidants
Alkylphenols
Fuel antioxidants
Tert-butyl compounds