2,6-Di-tert-butylphenol is an organic compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

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

Phenol

Phenol, also known as carbolic acid, phenic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl , bonded to a hydroxyl group. It is produced on a large scale as a precursor to many materials and useful compounds...

 and its derivatives are used industrially as UV stabilizer and an antioxidant

Antioxidant

An antioxidant is a molecule capable of inhibiting the oxidation of other molecules. Oxidation is a chemical reaction that transfers electrons or hydrogen from a substance to an oxidizing agent. Oxidation reactions can produce free radicals. In turn, these radicals can start chain reactions. When...

 for hydrocarbon

Hydrocarbon

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons from which one hydrogen atom has been removed are functional groups, called hydrocarbyls....

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

Aviation fuel

Aviation fuel is a specialized type of petroleum-based fuel used to power aircraft. It is generally of a higher quality than fuels used in less critical applications, such as heating or road transport, and often contains additives to reduce the risk of icing or explosion due to high temperatures,...

s.

Production

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

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

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

Applications

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

Acrylic acid

Acrylic acid is an organic compound with the formula CH2=CHCO2H. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols,...

.

Safety

The LD₅₀ is 9200, indicating a low toxicity.

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

• 2,4-Dimethyl-6-tert-butylphenol
  2,4-Dimethyl-6-tert-butylphenol
  2,4-Dimethyl-6-tert-butylphenol is an alkylated phenol used industrially as an antioxidant, e.g. to prevent gumming in fuels, and as an ultraviolet stabilizer. It is used in jet fuels, gasolines, and avgas. It is a clear liquid with melting point 21-23 °C and boiling point 248-249 °C. It is also...
  
  
• butylated hydroxytoluene
  Butylated hydroxytoluene
  Butylated hydroxytoluene , also known as butylhydroxytoluene, is a lipophilic organic compound that is primarily used as an antioxidant food additive as well as an antioxidant additive in cosmetics, pharmaceuticals, jet fuels, rubber, petroleum products, electrical transformer oil, and embalming...