Nonoxynols

Nonoxynols
IUPAC name

2-[2-(4-nonylphenoxy)ethoxy]ethanol
Other names

ethoxylated nonylphenol; (nonylphenoxy)polyethyleneoxide
Identifiers
CAS number 9016-45-9 Y
PubChem 24773
ChemSpider 23159 Y
ChEMBL CHEMBL194034 Y
Jmol-3D images Image 1
Properties
Molecular formula C19H32O3
Molar mass 308.45558
Hazards
LD50 4 g/kg
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Nonoxynols or nonylphenol ethoxylates are mixtures of nonionic surfactants used as detergents, emulsifiers, wetting agents, defoaming agents, etc. nonoxynol-9, the compound with approximately 9 repeating ethoxy groups, is a spermatocide, formulated primarily as a component of vaginal foams and creams. Arkopal-N60, with on average 6 ethylene glycol units is a related used surfactant.

Contents

Production

These compounds are produced by ethoxylation of alkylphenols. The precursor nonylphenol is derived from phenol and a mixture of nonenes.

Toxicity concerns

Concerns about the environmental impact of these compounds has increased since the 1990s. These surfactants have a mild to medium estrogenic function.[1] Consequently, this class of detergents has been effectively restricted for commercial "down-the-drain" applications in Europe, and these compounds are not found in laundry detergents in the USA.[2]

A 2011 investigation found residual levels of nonylphenol ethoxylates in samples of clothing from 14 brands sold in the U.S. (where this product is banned), including Adidas, Uniqlo, Calvin Klein, H&M, Abercrombie & Fitch, Lacoste, Converse and Ralph Lauren. [3] [4]

References

  1. ^ Comparison of protein expression in plasma from nonylphenol and bisphenol A-exposed Atlantic cod (Gadus morhua) and turbot (Scophthalmus maximus) by use of SELDI-TOF. Larsen Bodil K; Bjornstad Anne; Sundt Rolf C; Taban Ingrid C; Pampanin Daniela M; Andersen Odd Ketil International Research Institute of Stavanger (IRIS) AS, Mekjarvik 12, N-4070 Randaberg, Norway Aquatic toxicology (Amsterdam, Netherlands) (2006), 78 Suppl 1 S25-33.
  2. ^ . [NOTE: this referenced article [1] does not state that these compounds are not found in US laundry detergents, only that certain companies have removed them from their products]"Going green", cover story in chemical and Engineering Letters, vol. 85, No. 5, January 2007
  3. ^ http://www.treehugger.com/files/2011/08/big-brand-clothing-found-laced-with-toxic-chemicals.php
  4. ^ http://www.greenpeace.org/africa/en/Press-Centre-Hub/Publications/Dirty-Laundry-2-Hung-Out-to-Dry/

External links