{{Short description|Class of chemical compounds}} {{Chembox <!-- Images --> | ImageFile = Nonoxynol-9-V2.svg | ImageSize = 250px | ImageAlt = | ImageCaption = Nonoxynol-9{{efn|Image incorrectly shows a straight-chain nonyl group; should be branched.<ref>{{cite journal |title=Final Report on the Safety Assessment of Nonoxynols -2, -4, -8, -9, -10, -12, -14, -15, -30, -40, and -50 |journal=Journal of the American College of Toxicology |date=December 1983 |volume=2 |issue=7 |pages=35–60 |doi=10.3109/10915818309142001}}</ref>}} <!-- Names --> | IUPACName = | OtherNames = {{ubl|nonylphenol ethoxylates (NPE)|ethoxylated nonylphenol|nonaethylene glycols|polyethylene glycol nonyl phenyl ethers|(nonylphenoxy)polyethyleneoxide|Nonoxynol-''n''|PEG-''n'' nonyl phenyl ether|Arkopal N''n''0}} <!-- Sections --> | Section1 = {{Chembox Identifiers | CASNo = 9016-45-9 | UNNumber = | PubChem = Nonylphenol-ethoxylates | DTXSID = | EC_number = 500-024-6 }} | Section2 = {{Chembox Properties | Formula = {{chem2|C_{15+2''n''}H_{24+4''n''}O_{1+''n''}|}} | MolarMass = Variable | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} '''Nonoxynols''', also known as '''nonylphenol ethoxylates''' ('''NPEs'''), are a group of nonionic surfactants within the alkyl phenol ethoxylate superfamily. '''Alkyl phenol ethoxylates''' ('''APEs''', '''APEO''') have the chemical formula {{chem2|RC6H4(OC2H4)_{n}OH}} (1 < n < 20). Nonoxynols are the subfamily of APEs with R = ''iso''-{{chem2|C9H19}} (''iso''-nonyl). Like almost all APEs, nonoxynols are colorless (or nearly so) oils. Nonoxynols are used as detergents, emulsifiers, wetting agents or defoaming agents. The most commonly discussed compound nonoxynol-9 is a spermicide, formulated primarily as a component of vaginal foams and creams. Nonoxynol was found to metabolize into free nonylphenol when administered to lab animals.<ref>Sonnenschein, Carlos, and Ana M. Soto. "An Updated Review of Environmental Estrogen and Androgen Mimics and Antagonists." The Journal of Steroid Biochemistry and Molecular Biology 65.1-6 (1998): 143–50.</ref>
==Production== APEs are produced by ethoxylation of alkylphenols. Nonylphenol, the precursor to nonoxynols, is derived via alkylation of phenol with tripropylene, a mixture of branched nonenes.<ref>{{cite book|last=Fiege|first=H. |title=Phenol Derivatives |date=2000-06-15 |url=https://onlinelibrary.wiley.com/doi/10.1002/14356007.a19_313 |series=Ullmann's Encyclopedia of Industrial Chemistry |pages=a19_313 |publisher=Wiley-VCH Verlag GmbH & Co. KGaA|place=Weinheim, Germany|language=en|doi=10.1002/14356007.a19_313|isbn=978-3-527-30673-2|access-date=2022-06-08|oclc=46878292|last2=Voges|first2=H. W.|last3=Hamamoto|first3=T.|last4=Umemura|first4=S.|last5=Iwata|first5=T.|last6=Miki |first6=H.|last7=Fujita|first7=Y.|last8=Buysch|first8=H. J.|last9=Garbe|first9=D.}}</ref> Commercially available nonoxynols are mixtures that vary in the average number of repeating ethoxy (oxy-1,2-ethanediyl) groups, resulting in Nonoxynol-4, Nonoxynol-7, Nonoxynol-9, Nonoxynol-14, Nonoxynol-15, Nonoxynol-18, Nonoxynol-30, Nonoxynol-40, and Nonoxynol-50.
==Use== Nonoxynols have been used as detergents, emulsifiers and wetting agents in cosmetics, including hair products, and defoaming agents. Only nonoxynol-9 with 9 repeating ethoxy groups, has been used as a spermaticide, for vaginal foams and creams, and on condoms.<ref>[https://pubchem.ncbi.nlm.nih.gov/#tab/sidsrcname=ChemIDplus&query=26027-38-3&input_type=text Substance Name: Nonoxynols] Toxnet, U.S. National Library of Medicine, accessdate 14 March 2015</ref>
==Toxicity concerns== Concerns about the environmental impact of these compounds has increased since the 1990s. These surfactants have a mild to medium estrogenic function.<ref>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.</ref> Consequently, this class of detergents has been effectively restricted for commercial "down-the-drain" applications in Europe, and these compounds are no longer used by U.S. laundry manufacturers.<ref>[http://pubs.acs.org/cen/coverstory/85/8505cover.html "Going green"], cover story in ''Chemical and Engineering Letters'', vol. 85, No. 5, January 2007</ref> On January 14, 2016, the European Commission amended existing restriction on NPEs under the Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH) legislation, limiting NPE use in industrial and institutional cleaning, domestic cleaning, cosmetics and other applications including spermicides and in use as co-formulants in pesticides (except for pesticides where prior authorization was granted before July 17, 2003 in which effects of the restriction will not occur until date of their expiration) amounts equal to or exceeding 0.1% by weight, and limiting NPE residues on textile articles to 0.01% by weight, effective February 3, 2021.<ref name="EU REACH Restrictions Entry 46">{{cite web|title=EU REACH Annex XVII - Conditions of restriction Entry 46|url=https://www.echa.europa.eu/documents/10162/e5842a1e-e9f9-6096-2829-72f71c00eaab|publisher=European Chemicals Agency (ECHA)|accessdate=11 April 2024|date=13 January 2016}}</ref><ref name="EU REACH Restrictions Entry 46a">{{cite web|title=EU REACH Annex XVII - Conditions of restriction Entry 46a |url=https://echa.europa.eu/documents/10162/7dcd73a4-e80d-47c5-ba0a-a5f4361bf4b1|publisher=European Chemicals Agency (ECHA)|accessdate=11 April 2024|date=13 January 2016}}</ref> Previously, the use of NPE was forbidden within the EU, but there was no limit on the level of NPE residue on imported articles.
On 13 August 2008, the Swedish newspaper ''Göteborg Posten (sv)'' reported finding high levels of the NPE in Björn Borg underwear.<ref name="Ekstrand2009">{{cite news|last1=Ekstrand|first1=Lena|title=Skyhöga halter av miljögift. Det blev resultatet när GP Konsument lät analysera Björn Borg-kalsonger. Giftet är förbjudet inom EU, men tillåtet i importerade textilier|url=https://www.gp.se/livsstil/konsument/borg-kalsonger-08-1.1119077|accessdate=25 June 2017|work=Göteborg Posten|date=13 August 2008}}</ref> A 2011 investigation found residual levels of NPE in samples of clothing from 14 brands sold in the U.S., including Adidas, Uniqlo, Calvin Klein, H&M, Abercrombie & Fitch, Lacoste, Converse and Ralph Lauren.<ref>{{cite web |last=Heimbuch |first=Jaymi |url=http://www.treehugger.com/files/2011/08/big-brand-clothing-found-laced-with-toxic-chemicals.php |title=Big-Brand Clothing Found Laced with Toxic Chemicals |publisher=TreeHugger |date=2011-08-23 |accessdate=2013-02-09 |archive-date=2020-11-11 |archive-url=https://web.archive.org/web/20201111213024/http://www.treehugger.com/files/2011/08/big-brand-clothing-found-laced-with-toxic-chemicals.php |url-status=dead }}</ref><ref>{{cite web|url=https://www.greenpeace.org/africa/en/Press-Centre-Hub/Publications/Dirty-Laundry-2-Hung-Out-to-Dry/ |title=Dirty Laundry 2: Hung Out to Dry | Greenpeace Africa |publisher=Greenpeace.org |date=2011-08-23 |accessdate=2013-02-09}}</ref>
==Notes== {{notelist}}
==References== {{Reflist}}
==External links== * J.K.G. Dondt, G. Gomppner, D. Richter (Eds) Soft matter: complex materials on mesoscopic scales - Schriften des Forschungszentrum Jülich, Vol. 10, 2002.
Category:Non-ionic surfactants Category:Polyethers Category:Phenol ethers Category:Primary alcohols Category:Alkyl-substituted benzenes