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. The ...

with the structural formula 2,6-((CH₃)₃C)₂C₆H₃OH. This colorless solid

alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloalk ...

ated

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 req ...

and its derivatives are used industrially as UV stabilizers and

antioxidant Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals. This can lead to polymerization and other chain reactions. They are frequently added to industrial products, such as fuels and lubricant ...

s 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 ex ...

-based products ranging from petrochemicals to plastics. Illustrative of its usefulness, it prevents gumming in

aviation fuel Aviation fuels are petroleum-based fuels, or petroleum and synthetic fuel blends, used to power aircraft. They have more stringent requirements than fuels used for ground use, such as heating and road transport, and contain additives to enhanc ...

Production

2,6-Di-''tert''-butylphenol is prepared industrially via the Friedel–Crafts alkylation of phenol with

isobutene Isobutylene (or 2-methylpropene) is a hydrocarbon with the chemical formula . It is a four-carbon branched alkene (olefin), one of the four isomers of butylene. It is a colorless flammable gas, and is of considerable industrial value. Productio ...

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 ...

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

methyl methacrylate Methyl methacrylate (MMA) is an organic compound with the formula CH2=C(CH3)COOCH3. This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA ...

. This compound is used as a feedstock in the synthesis of more complex antioxidants such as

Irganox 1098 Irganox 1098 is the trade name for ''N'',''N''′-(hexane-1,6-diyl)bis -(3,5-di-''tert''-butyl-4-hydroxyphenyl)propanamide'', a primary antioxidant manufactured by BASF primarily used for stabilizing polymers, especially polyamide A polyamide is ...

. 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.

References

{{DEFAULTSORT:Di-tert-butylphenol, 2,6- Antioxidants Alkylphenols Fuel antioxidants Tert-butyl compounds

Production

Applications

Safety and regulation

See also

References