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
SMILES O(c1ccc(cc1)CCCCCCCCC)CCOCCO
InChI InChI=1S/C19H32O3/c1-2-3-4-5-6-7-8-9-18-10-12-19(13-11-18)22-17-16-21-15-14-20/h10-13,20H,2-9,14-17H2,1H3 Y Key: BLXVTZPGEOGTGG-UHFFFAOYSA-N Y InChI=1/C19H32O3/c1-2-3-4-5-6-7-8-9-18-10-12-19(13-11-18)22-17-16-21-15-14-20/h10-13,20H,2-9,14-17H2,1H3 Key: BLXVTZPGEOGTGG-UHFFFAOYAL
Properties
Molecular formula	C19H32O3
Molar mass	308.45558
Hazards
LD50	4 g/kg
Y (verify) (what is: Y/N?) 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.

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

• Brief technical specification of ethoxylated nonylphenol (neonol)
• J.K.G. Dondt, G. Gomppner, D. Richter (Eds) Soft matter: complex materials on mesoscopic scales - Schriften des Forschungszentrum Jülich, Vol. 10, 2002.