View source for Sodium laureth sulfate

{{Distinguish|Sodium lauryl sulfate}}
{{chembox
| verifiedrevid = 303804168
|   Name = Sodium laureth sulfate
|   ImageFile = Sodium laureth sulfate structure.png
|   IUPACName =<!-- No systematic name, because not single molecule. -->
|   OtherNames = Sodium lauryl ether sulfate; sodium laureth sulphate; sodium lauryl ether sulphate
| Section1 = {{Chembox Identifiers
|   Abbreviations = SLES
|   CASNo_Ref = {{cascite}}
| CASNo = 9004-82-4
|   SMILES =
  }}
| Section2 = {{Chembox Properties
|   Formula = CH<sub>3</sub>(CH<sub>2</sub>)<sub>10</sub>CH<sub>2</sub>(OCH<sub>2</sub>CH<sub>2</sub>)<sub>n</sub>OSO<sub>3</sub>Na<br>C<sub>11+n</sub>H<sub>23+4n</sub>NaO<sub>4+n</sub>S
|   MolarMass = around 420 g/mol<br>(274.35 + 44.05n) g mol<sup>−1</sup>
|   Density =
|   MeltingPt =
|   BoilingPt =
  }}
}}

'''Sodium laureth sulfate''', or '''sodium lauryl ether sulfate''' ('''SLES'''), is a [[detergent]] and [[surfactant]] found in many personal care products ([[soap]]s, [[shampoo]]s, [[toothpaste]] etc.). SLES is an inexpensive and very effective [[foaming agent]].<ref name=Ullmann>Kurt Kosswig,"Surfactants" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2005, Weinheim. {{DOI|10.1002/14356007.a25_747}}</ref>

SLES has been shown to produce eye or skin irritation in experimental animals and in some human test subjects.<ref name="Final Report"/> Some products containing SLES have been found to contain low levels of the carcinogen [[1,4-dioxane]], with the recommendation from the [[U.S. Food and Drug Administration|FDA]] that these levels be monitored.<ref name="Occurrence_Dioxane"/>

== Chemical structure ==

Its chemical formula is [[carbon|C]][[hydrogen|H]]<sub>3</sub>(CH<sub>2</sub>)<sub>10</sub>CH<sub>2</sub>([[oxygen|O]]CH<sub>2</sub>CH<sub>2</sub>)<sub>''n''</sub>O[[sulfur|S]]O<sub>3</sub>[[sodium|Na]]. Sometimes the number represented by ''n'' is specified in the name, for example laureth-2 sulfate. The commercial product is heterogeneous in the number of ethoxyl groups, where ''n'' is the mean.  It is common for commercial products for ''n''= 3. SLES is prepared by [[ethoxylation]] of [[Dodecanol|dodecyl alcohol]].  The resulting ethoxylate is converted to an [[organosulfate|half ester of sulfuric acid]], which is [[Neutralization (chemistry)|neutralized]] by conversion to the [[sodium]] [[salt (chemistry)|salt]].<ref name=Ullmann/> The related surfactant [[sodium lauryl sulfate]] (also known as sodium dodecyl sulfate or SLS) is produced similarly, but without the ethoxylation step.  SLS and [[ammonium lauryl sulfate]] (ALS) are commonly used alternatives to SLES in consumer products.<ref name=Ullmann/>

== Application ==

SLES, SLS and ALS are [[surfactant]]s that are used in many cosmetic products for their cleansing and emulsifying properties.  They behave similarly to [[soap]].

== Toxicology ==
=== Irritation ===

Although SLES is considered safe at the concentrations used in cosmetic products, it is an [[irritant]] similar to other [[detergents]], with the irritation increasing with concentration.<ref name="Final Report">{{cite journal | title = Final report on the safety assessment of sodium laureth sulfate and ammonium laureth sulfate | journal = Journal of the American College of Toxicology | year = 1983 | volume = 2 | issue = 5 | pages = 1–34 | doi = 10.3109/10915818309140713 }}</ref> SLES has been shown to produce eye or skin irritation in experimental animals and in some human test subjects.<ref name="Final Report"/> The related surfactant SLS is a [[atopic dermatitis|known irritant]],<ref name="Agner_T">{{cite journal |author=Agner T |title=Susceptibility of atopic dermatitis patients to irritant dermatitis caused by sodium lauryl sulphate |journal=Acta Dermato-venereologica |volume=71 |issue=4 |pages=296–300 |year=1991 |pmid=1681644}}</ref><ref name="A._Nassif_1994">{{cite journal |author=Nassif A, Chan SC, Storrs FJ, Hanifin JM |title=Abnormal skin irritancy in atopic dermatitis and in atopy without dermatitis |journal=Archives of Dermatology |volume=130 |issue=11 |pages=1402–7 |year=1994 |month=November |pmid=7979441 |doi=10.1001/archderm.130.11.1402}}</ref> and research suggests that SLES can also cause irritation after extended exposure in some people.<ref name="Allergic_Contact_Dermatitis">{{cite journal |author=Magnusson B, Gilje O |title=Allergic contact dermatitis from a dish-washing liquid containing lauryl ether sulphate |journal=Acta Dermato-venereologica |volume=53 |issue=2 |pages=136–40 |year=1973 |pmid=4120956}}</ref><ref name="Shampoo_Dermatitis">{{cite journal |author=Van Haute N, Dooms-Goossens A |title=Shampoo dermatitis due to cocobetaine and sodium lauryl ether sulphate |journal=Contact Dermatitis |volume=9 |issue=2 |pages=169 |year=1983 |month=March |pmid=6851541 |doi=10.1111/j.1600-0536.1983.tb04348.x}}</ref>

=== Carcinogenicity ===

Toxicology research by the [[Occupational Safety and Health Administration|OSHA]], [[National Toxicology Program|NTP]], and [[International Agency for Research on Cancer|IARC]] supports the conclusions of the [[Cosmetic, Toiletry, and Fragrance Association]] (CTFA) and the [[American Cancer Society]] that SLES is not a carcinogen.<ref name="CTFA">Rumor: Sodium Lauryl Sulfate Causes Cancer. ''The Cosmetic, Toiletry, and Fragrance Association.'' 13, October 2000. [http://www.personalcarecouncil.org/Template.cfm?Section=Internet_Rumors&Template=/ContentManagement/ContentDisplay.cfm&ContentID=867 Consumer Information]</ref> The [[U.S. Environmental Protection Agency]] classifies 1,4-dioxane to be a probable human [[carcinogen]] (having observed an increased incidence of cancer in controlled animal studies, but not in epidemiological studies of workers using the compound), and a known irritant (with a no-observed-adverse-effects level of 400 milligrams per cubic meter) at concentrations significantly higher than those found in commercial products.<ref name="U.S.EPA_Dioxane">1,4-Dioxane (1,4-Diethyleneoxide). Hazard Summary. ''U.S. Environmental Protection Agency.'' Created in April 1992; Revised in January 2000. [http://www.epa.gov/ttn/atw/hlthef/dioxane.html Fact Sheet]</ref> Under [[Proposition 65]], 1,4-dioxane is classified in the U.S. state of California to cause cancer.<ref name="prop65">{{cite web |title=Proposition 65 List of Chemicals |author= |url=http://www.oehha.org/prop65/prop65_list/files/P65single040210.pdf |format=PDF |title=1,4-Dioxane cancer 123-91-1 January 1, 1988 |publisher=Office of Environmental Health Hazard Assessment}}</ref><ref>{{cite news |url=http://www.bloomberg.com/apps/news?pid=conewsstory&refer=conews&tkr=WFMI:US&sid=aDC5vdNMQCiM |format= |title=California Files Prop 65 Lawsuit Against Whole Foods, Avalon |author= |work=Bloomberg |publisher= |date= |accessdate=}}</ref>

=== 1,4-Dioxane contaminant ===

Some products containing SLES have been found to contain low levels of the known carcinogen [[1,4-dioxane]], with the recommendation from the [[U.S. Food and Drug Administration]] that these levels be monitored.<ref name="Occurrence_Dioxane">{{cite journal |author=Black RE, Hurley FJ, Havery DC |title=Occurrence of 1,4-dioxane in cosmetic raw materials and finished cosmetic products |journal=Journal of AOAC International |volume=84 |issue=3 |pages=666–70 |year=2001 |pmid=11417628}}</ref> The FDA encourages manufacturers to remove 1,4-dioxane, though it is not required by federal law.<ref name="FDA_Dioxane">FDA/CFSAN--Cosmetics Handbook Part 3: Cosmetic Product-Related Regulatory Requirements and Health Hazard Issues. [http://web.archive.org/web/20080115201046/www.cfsan.fda.gov/~dms/cos-hdb3.html Prohibited Ingredients and other Hazardous Substances: 9. Dioxane]</ref>

== See also ==
* [[Sodium lauryl sulfate]]
* [[Sodium myreth sulfate]]

== References ==
{{reflist}}

== External links ==
* [http://healthychild.org/issues/chemical-pop/sodium_laureth_sulfate/ Description and health effects of sodium laureth sulfate] by Children's Health Environmental Coalition
* {{HPD|134}}

[[Category:Cosmetics chemicals]]
[[Category:Ethers]]
[[Category:Household chemicals]]
[[Category:Organosulfates]]
[[Category:Sodium compounds]]
[[Category:Anionic surfactants]]

[[cs:Laurethsulfát sodný]]
[[de:Natriumdodecylpoly(oxyethylen)sulfat]]
[[fr:Laureth sulfate de sodium]]
[[nl:Natriumlaurylethersulfaat]]
[[ja:ラウレス硫酸ナトリウム]]
[[pt:Lauriléter sulfato de sódio]]
[[ur:Sodium laureth sulfate]]
[[zh:十二烷基聚氧乙醚硫酸钠]]
[[Category:2Fix]]