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| Nonylphenol | |
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| IUPAC name | 4-Nonylphenol |
| Other names | p-Nonylphenol |
| Identifiers | |
| CAS number | 104-40-5 |
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| Properties | |
| Molecular formula | C15H24O |
| Molar mass | 220.35 g/mol |
| Appearance | White crystals |
| Density | 0.94 |
| Melting point |
43-45 °C |
| Boiling point |
180-181 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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Nonylphenol is an organic compound of the wider family of alkylphenols. It is a product of industrial synthesis formed during the alkylation process of phenols, particularly in the synthesis of polyethoxylate detergents. Because of their man-made origins, nonylphenols are classified as xenobiotics. In nonylphenols, a hydrocarbon chain of nine carbon atoms is attached to the phenol ring in either the ortho (2), meta (3), or para (4) position, with the most common ring isomers being ortho or para (e.g. figure 1 para-nonylphenol). Moreover, the alkyl chains can exist as either linear n-alkyl chains, or complex branched chains. Nonylphenol is commonly obtained as a mixture of isomers, and is thus usually found as a pale yellow liquid at room temperature with a freezing point of -10°C and a boiling point of 295-320°C. However, pure isomers of nonylphenol crystallize readily at room temperatures and for example, para-n-nonylphenol, forms white crystals at room temperature.
Ethoxylated alkylphenols, alkylphenol ethoxylates (APE), are used as industrial surfactants in manufacture of wool and metal, as emulsifiers for emulsion polymerization, in laboratory detergents, and pesticides. APEs are a component of some household detergents outside of Europe; within Europe, due to environmental concerns, they are replaced by more expensive but safer alcohol ethoxylates.
Nonoxynol-9, one of the APEs, is used as a surfactant in cleaning and cosmetic products, and as a spermicide in contraceptives.
In 1984, the formation of 4-nonylphenols from nonylphenol ethoxylates in wastewater treatment plants was first discovered.1
Nonylphenol, and a related compound tert-octylphenol, were first detected as an air pollutant in New York City and New Jersey, probably due to its evaporation from the Hudson river and other smaller rivers in the region that routinely receive municipal wastewaters. It is possible that the atmosphere is a destructive sink for nonylphenol as it is probably reactive with atmospheric radicals and/or is photoactive.
Nonylphenol and nonyphenol ethoxylates have been banned in the European Union as a hazard to human and environmental safety.2
Biochemically, p-nonylphenol and many of its derivatives act as a xenoestrogen.
References
- ^ W. Giger, P. H. Brunner, C. Schaffner: 4-Nonylphenol in sewage sludge: accumulation of toxic metabolites from nonionic surfactants. Science, 225(4662), 1984, 623–625, doi:10.1126/science.6740328
- ^ Official Journal of the European Union: DIRECTIVE 2003/53/EC OF THE EUROPEAN PARLIAMENT AND OF THE COUNCIL of 18 June 2003 amending for the 26th time Council Directive 76/769/EEC relating to restrictions on the marketing and use of certain dangerous substances and preparations (nonylphenol, nonylphenol ethoxylate and cement), July 17, 2003
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