4-''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 formula (CH₃)₃CC₆H₄OH. It is one of three isomeric ''tert''-butyl

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 ...

s. It is a white solid with a distinct phenolic odor. It dissolves in basic water.

Manufacture

It can be prepared by acid-catalyzed

alkylation Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecti ...

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. Producti ...

, 2-''tert''-butylphenol being the major side product. It can be produced by diverse

transalkylation In organic chemistry, transalkylation is a chemical reaction involving the transfer of an alkyl group from one organic compound to another. The reaction is used for the transfer of methyl and ethyl groups between benzene rings. This is of particul ...

reactions.

Uses

It major uses are in the production of epoxy resins and curing agents and also in polycarbonate resins. It has also found use in the production of

phenolic resin Phenol formaldehyde resins (PF) or phenolic resins (also infrequently called phenoplasts) are synthetic polymers obtained by the reaction of phenol or substituted phenol with formaldehyde. Used as the basis for Bakelite, PFs were the first commerc ...

s. Another use is in the production of

para tertiary butylphenol formaldehyde resin 300px, Illustration of allergic contact dermatitis Para tertiary butylphenol formaldehyde resin also known as p-tert-butylphenol-formaldehyde resin (PTBP-FR) or 4-(1,1-dimethylethyl) phenol (PTBP Formaldehyde) is a phenol-formaldehyde resin found i ...

. It has also found use as a

plasticizer A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture. Plasticiz ...

. Bisphenol A is difunctional and used to produce epoxy resin and polycarbonate. 4-''tert''-Butylphenol is monofunctional and so in polymer science terms, bisphenol A is a polymer chain extender but 4-''tert''-butylphenol is a chain stopper or sometimes called endcapper. It is thus use to control molecular weight by limiting chain growth. 4-''tert''-Butylphenol has an OH group and so it may be reacted with epichlorohydrin and

caustic soda Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...

to produce the glycidyl ether which is used in epoxy resin chemistry. This molecule has the CAS Registry number of 3101-60-8.

Laboratory reactions

Hydrogenation gives ''trans''-4-''tert''-butylcyclohexanol. Controlled condensation with formaldehyde gives

calixarene A calixarene is a macrocycle or cyclic oligomer based on a methylene-linked phenols. With hydrophobic cavities that can hold smaller molecules or ions, calixarenes belong to the class of cavitands known in host–guest chemistry. Nomenclature Cal ...

Safety

OSHA records show it as an irritant and has developed suggested test methods for its detection. A

European Union The European Union (EU) is a supranational political and economic union of member states that are located primarily in Europe. The union has a total area of and an estimated total population of about 447million. The EU has often been de ...

risk assessment report into the molecule dated May 2006 suggested it had potential depigmenting properties and was a potential endocrine disruptor. This was done under its EINECS number of 202-679-0. Other papers have been published showing similar findings.

References

{{DEFAULTSORT:Butylphenol, 4-tert- Alkylphenols