Alkylphenols are a family of organic compounds obtained by the alkylation of . The term is usually reserved for commercially important propylphenol, butylphenol, amylphenol, heptylphenol, octylphenol, nonylphenol, dodecylphenol and related "long chain alkylphenols"
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Production and use
The long-chain alkylphenols are prepared by
alkylation of
phenol with
alkenes:
- C6H5OH + RR'C=CH2 → RR'CH−CH2−C6H4OH
In this way, about 500M kg/y are produced. Alkylphenols ethoxylates are common surfactants. Long-chain alkylphenols are used extensively as precursors to detergents. By condensation with formaldehyde, some alkylphenols are components in
.
[ These compounds are also used as building-block chemicals in making fragrances, thermoplastic elastomers, antioxidants, oil field chemicals, and fire retardant materials. As plastizers and antioxidants, alkylphenols are also found in tires, adhesives, coatings, carbonless copy paper and high performance rubber products.
]
Environmental controversy over nonylphenols
Alkylphenols are xenoestrogens. Long chain Alkylphenols have the most potent estrogenic activity. The European Union has implemented sales and use restrictions on certain applications in which are used because of their "toxicity, persistence, and the liability to bioaccumulate" but the United States EPA has taken a slower approach.[ European Bans on Surfactant Trigger Transatlantic Debate]