Alkylphenol

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 phenolic resins. 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 nonylphenols are used because of their "toxicity, persistence, and the liability to bioaccumulate" but the United States EPA has taken a slower approach. In order to restrict chemicals in the United States, the Environmental Protection Agency (EPA)needs to prove that those chemicals are unreasonably harmful. This has yet to be the case with Alkylphenols, upon which there is still research being done to prove their harmful effects.

References

References

1. {{cite encyclopedia. (2002). Wiley-VCH
2. Kovarova, J., Blahova, J., Divisova, L., & Svobodova, Z. (2013). Alkylphenol ethoxylates and alkylphenols – update information on occurrence, fate and toxicity in aquatic environment. Polish Journal of Veterinary Sciences, 16(4), 762–771. https://doi.org/10.2478/pjvs-2013-0111
3. (May 2009). "Alkylphenol xenoestrogens with varying carbon chain lengths differentially and potently activate signaling and functional responses in GH3/B6/F10 somatomammotropes". Environmental Health Perspectives.
4. [http://pubs.acs.org/hotartcl/est/97/jul/euro.html European Bans on Surfactant Trigger Transatlantic Debate]
5. J. Kovarova, J. Blahova, L. Divisova, Z.Svobodova. "Alkylphenol ethoxylates and alkylphenols– update information on occurrence,fate and toxicity in aquatic environment".
6. Ogunbiyi, Olutobi Daniel. (2025). "Prioritization of Emerging Pollutants Used for Fingerprinting Specific Water Sources". UNESCO.
7. US EPA, OCSPP. (2014-08-04). "EPA's Review Process for New Chemicals".