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{{cs1 config|name-list-style=vanc}}
{{Distinguish|Sodium lauryl sulfate}}
{{Distinguish|text=]. For the Loud Family song, see ]}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 448974536
| Watchedfields = changed
| Name = Sodium laureth sulfate
| verifiedrevid = 477002177
| ImageFile = Sodium laureth sulfate structure.png
| Name = Sodium laureth sulfate
| IUPACName =<!-- No systematic name, because not single molecule. -->
| OtherNames = Sodium lauryl ether sulfate; sodium laureth sulphate; sodium lauryl ether sulphate | ImageFile = Sodium laureth sulfate structure.svg
| ImageSize = 250px
| Section1 = {{Chembox Identifiers
| IUPACName = α-Sulfo-ω-(dodecyloxy)-poly(oxyethane-1,2-diyl), sodium salt
| Abbreviations = SLES
| OtherNames = Sodium lauryl ether sulfate<br />Sodium laureth sulphate<br />Sodium dodecyl polyoxyethylene sulfate<br />Sodium lauryl polyoxyethylene sulfate<br />Sodium lauryl dioxyethylene sulfate<br />Sodium lauryl trioxyethylene sulfate<br />Sodium laureth-2 sulfate<br />Sodium laureth-3 sulfate
| CASNo_Ref = {{cascite|correct|CAS}}
|Section1={{Chembox Identifiers
| CASNo = 9004-82-4
| index_label = sodium laureth-2 sulfate
| SMILES =
| index1_label = sodium laureth-3 sulfate
| ChemSpiderID = NA
| index2_label = sodium laureth-5 sulfate
}}
| Abbreviations = SLES
| Section2 = {{Chembox Properties
| CASNo_Ref = {{cascite|correct|CAS}}
| 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>12+2n</sub>H<sub>25+4n</sub>NaO<sub>4+n</sub>S
| CASNo = 3088-31-1
| MolarMass = around 420 g/mol<br>(288.38 + 44.05n) g mol<sup>−1</sup>
| CASNo1_Ref = {{cascite|correct|CAS}}
| Density =
| CASNo1 = 13150-00-0
| MeltingPt =
| CASNo2_Ref = {{cascite|correct|CAS}}
| BoilingPt =
| CASNo2 = 9004-82-4
}}

| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = ZZQ59TY3KG
| UNII1_Ref = {{fdacite|changed|FDA}}
| UNII1 = BPV390UAP0
| UNII2_Ref = {{fdacite|changed|FDA}}
| UNII2 = 410Q7WN1BX

| PubChem3 = 23665884
| PubChem3_Comment = (sodium 2-dodecoxyethyl sulfate)
| SMILES =
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = none
}}
|Section2={{Chembox Properties
| Formula = CH<sub>3</sub>(CH<sub>2</sub>)<sub>11</sub>(OCH<sub>2</sub>CH<sub>2</sub>)<sub>n</sub>OSO<sub>3</sub>Na
| MolarMass = Variable; typically around 421&nbsp;g/mol<br />(288.38 + 44.05n) g/mol
| Density =
| MeltingPt =
| BoilingPt =
}}
|Section3={{Chembox Hazards
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 0
}}
}} }}


'''Sodium laureth sulfate''', or '''sodium lauryl ether sulfate''' ('''SLES'''), is a ] and ] found in many personal care products (]s, ]s, ] etc.). SLES is an inexpensive and very effective ].<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, SLS and ALS are ]s that are used in many cosmetic products for their cleansing and emulsifying properties. They behave similarly to ]. '''Sodium laureth sulfate''' ('''SLES'''), an accepted contraction of '''sodium lauryl ] sulfate''', also called sodium alkylethersulfate, is an ]ic ] and ] found in many personal care products (]s, ]s, ], etc.) and for industrial uses. SLES is an inexpensive and very effective ].<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, ] (SLS), ] (ALS), and ] are ]s that are used in many cosmetic products for their cleaning and emulsifying properties. It is derived from ] or ]. In herbicides, it is used as a surfactant to improve absorption of the herbicidal chemicals<ref>{{cite web|title=Safety Data Sheet Bayer FINALE Herbicide|url=https://www.environmentalscience.bayer.co.uk/~/media/PRFUnitedKingdom/Product%20MSDS/Finale%20150.ashx|access-date=August 20, 2021|website=Bayer Environmental Sciences UK}}</ref> and reduces time the product takes to be rainfast, when enough of the herbicidal agent will be absorbed.


Its chemical formula is {{chem2|auto=1|CH3(CH2)11(OCH2CH2)_{''n''}OSO3Na}}. Sometimes the number represented by ''n'' is specified in the name, for example laureth-2 sulfate. The product is heterogeneous in the number of ], where ''n'' is the mean. Laureth-3 sulfate is the most common one in commercial products.
== Chemical structure ==
Its chemical formula is ]]<sub>3</sub>(CH<sub>2</sub>)<sub>10</sub>CH<sub>2</sub>(]CH<sub>2</sub>CH<sub>2</sub>)<sub>''n''</sub>O]O<sub>3</sub>]. 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 ] of ]. The resulting ethoxylate is converted to an ], which is ] by conversion to the ] ].<ref name=Ullmann/> The related surfactant ] (also known as sodium dodecyl sulfate or SLS) is produced similarly, but without the ethoxylation step. SLS and ] (ALS) are commonly used alternatives to SLES in consumer products.<ref name=Ullmann/>


== Toxicology == == Production ==
SLES is prepared by ] of ], which is produced industrially from ] or ]. The resulting ethoxylate is converted to a ], which is ] by conversion to the ] ].<ref name=Ullmann /> The related surfactant ] or SLS (also known as sodium dodecyl sulfate or SDS) is produced similarly, but without the ethoxylation step. SLS and ] (ALS) are commonly used alternatives to SLES in consumer products.<ref name=Ullmann/>
=== Irritation ===
Although SLES is considered safe at the concentrations used in cosmetic products, it is an ] similar to other ], 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 ],<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 === == Safety ==
Tests in the US indicate that it is safe for consumer use. The Australian government's ] and its ] (NICNAS) have determined that SLES does not react with DNA.<ref name="NICNAS">{{cite web |url=http://www.nicnas.gov.au/chemical-information/imap-assessments/imap-group-assessment-report?assessment_id=177 |title=NICNAS SLES animal test |access-date=3 November 2013 |archive-date=26 June 2018 |archive-url=https://web.archive.org/web/20180626030210/https://www.nicnas.gov.au/chemical-information/imap-assessments/imap-group-assessment-report?assessment_id=177 |url-status=dead }}</ref>
Toxicology research by the U.S. ], ], and ] supports the conclusions of the ] (CTFA) and the ] that SLES is not a carcinogen.{{Citation needed|date=December 2011}}

=== Irritation ===
Like many other ]s, SLES is an ].<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 | s2cid = 208502361 }}</ref> It has been shown that SLES causes eye or skin irritation in experiments conducted on animals and humans.<ref name="Final Report" /> The related surfactant SLS is also a 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 |doi=10.2340/0001555571296300 |pmid=1681644|s2cid=37806228 |doi-access=free }}</ref><ref name="A._Nassif_1994">{{cite journal|vauthors=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 |date=November 1994 |pmid=7979441 |doi=10.1001/archderm.130.11.1402}}</ref><ref name="Allergic_Contact_Dermatitis">{{cite journal|vauthors=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 |doi=10.2340/0001555553136140 |pmid=4120956|s2cid=9398646 |doi-access=free }}</ref><ref name="Shampoo_Dermatitis">{{cite journal|vauthors=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 |date=March 1983 |pmid=6851541 |doi=10.1111/j.1600-0536.1983.tb04348.x|s2cid=42092578 }}</ref>


=== 1,4-Dioxane contamination === === 1,4-Dioxane contamination ===
Some products containing SLES have been found to also contain low{{Vague|how low? ppm, ppb, ppt, ppq?|date=September 2011}} levels of ], with the recommendation from the ] 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 ] classifies 1,4-dioxane to be a probable human ] (not observed in epidemiological studies of workers using the compound, but resulting in more cancer cases in controlled animal studies), 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. </ref> Under ], 1,4-dioxane is classified in the U.S. state of California to cause cancer.<ref name="prop65">{{Cite web |title=1,4-Dioxane cancer 123-91-1 January 1988 |author= |url=http://www.oehha.org/prop65/prop65_list/files/P65single040210.pdf |format=PDF |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> 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. </ref> Products containing SLES can be contaminated with up to 300 ppm of ], a by-product of SLES production. 1,4-Dioxane is classified by the ] as a ]: ''possibly carcinogenic to humans''. The ] (FDA) recommends that these levels be monitored,<ref name="Occurrence_Dioxane">{{cite journal|vauthors=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 |doi=10.1093/jaoac/84.3.666 |pmid=11417628|doi-access=free }}</ref> and 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. </ref>


== See also == == See also ==
* ] * ]
* ]
* ] * ]
* ] * ]
* ]
* ]
* ], a common impurity of SLES


== References == == References ==
{{Reflist}} {{Reflist|30em}}


== External links == == External links ==
* {{CPID|id=8}}
* by Children's Health Environmental Coalition

* {{HPD|134}}
{{Use dmy dates|date=September 2010}} {{Use dmy dates|date=April 2020}}

{{Authority control}}


{{DEFAULTSORT:Sodium Laureth Sulfate}}
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Latest revision as of 10:46, 21 December 2024

Not to be confused with Sodium lauryl sulfate. For the Loud Family song, see Interbabe Concern.
Sodium laureth sulfate
Names
IUPAC name α-Sulfo-ω-(dodecyloxy)-poly(oxyethane-1,2-diyl), sodium salt
Other names Sodium lauryl ether sulfate
Sodium laureth sulphate
Sodium dodecyl polyoxyethylene sulfate
Sodium lauryl polyoxyethylene sulfate
Sodium lauryl dioxyethylene sulfate
Sodium lauryl trioxyethylene sulfate
Sodium laureth-2 sulfate
Sodium laureth-3 sulfate
Identifiers
CAS Number
Abbreviations SLES
ChemSpider
  • sodium laureth-2 sulfate: none
ECHA InfoCard 100.036.281 Edit this at Wikidata
PubChem CID
  • 23665884 (sodium 2-dodecoxyethyl sulfate)
UNII
CompTox Dashboard (EPA)
Properties
Chemical formula CH3(CH2)11(OCH2CH2)nOSO3Na
Molar mass Variable; typically around 421 g/mol
(288.38 + 44.05n) g/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Sodium laureth sulfate (SLES), an accepted contraction of sodium lauryl ether sulfate, also called sodium alkylethersulfate, is an anionic detergent and surfactant found in many personal care products (soaps, shampoos, toothpaste, etc.) and for industrial uses. SLES is an inexpensive and very effective foaming agent. SLES, sodium lauryl sulfate (SLS), ammonium lauryl sulfate (ALS), and sodium pareth sulfate are surfactants that are used in many cosmetic products for their cleaning and emulsifying properties. It is derived from palm kernel oil or coconut oil. In herbicides, it is used as a surfactant to improve absorption of the herbicidal chemicals and reduces time the product takes to be rainfast, when enough of the herbicidal agent will be absorbed.

Its chemical formula is CH3(CH2)11(OCH2CH2)nOSO3Na. Sometimes the number represented by n is specified in the name, for example laureth-2 sulfate. The product is heterogeneous in the number of ethoxyl groups, where n is the mean. Laureth-3 sulfate is the most common one in commercial products.

Production

SLES is prepared by ethoxylation of dodecyl alcohol, which is produced industrially from palm kernel oil or coconut oil. The resulting ethoxylate is converted to a half ester of sulfuric acid, which is neutralized by conversion to the sodium salt. The related surfactant sodium lauryl sulfate or SLS (also known as sodium dodecyl sulfate or SDS) is produced similarly, but without the ethoxylation step. SLS and ammonium lauryl sulfate (ALS) are commonly used alternatives to SLES in consumer products.

Safety

Tests in the US indicate that it is safe for consumer use. The Australian government's Department of Health and Ageing and its National Industrial Chemicals Notification and Assessment Scheme (NICNAS) have determined that SLES does not react with DNA.

Irritation

Like many other detergents, SLES is an irritant. It has been shown that SLES causes eye or skin irritation in experiments conducted on animals and humans. The related surfactant SLS is also a known irritant.

1,4-Dioxane contamination

Products containing SLES can be contaminated with up to 300 ppm of 1,4-dioxane, a by-product of SLES production. 1,4-Dioxane is classified by the International Agency for Research on Cancer as a Group 2B carcinogen: possibly carcinogenic to humans. The United States Food and Drug Administration (FDA) recommends that these levels be monitored, and encourages manufacturers to remove 1,4-dioxane, though it is not required by federal law.

See also

References

  1. ^ Kurt Kosswig,"Surfactants" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2005, Weinheim. doi:10.1002/14356007.a25_747
  2. "Safety Data Sheet Bayer FINALE Herbicide". Bayer Environmental Sciences UK. Retrieved 20 August 2021.
  3. "NICNAS SLES animal test". Archived from the original on 26 June 2018. Retrieved 3 November 2013.
  4. ^ "Final report on the safety assessment of sodium laureth sulfate and ammonium laureth sulfate". Journal of the American College of Toxicology. 2 (5): 1–34. 1983. doi:10.3109/10915818309140713. S2CID 208502361.
  5. Agner T (1991). "Susceptibility of atopic dermatitis patients to irritant dermatitis caused by sodium lauryl sulphate". Acta Dermato-Venereologica. 71 (4): 296–300. doi:10.2340/0001555571296300. PMID 1681644. S2CID 37806228.
  6. Nassif A, Chan SC, Storrs FJ, Hanifin JM (November 1994). "Abnormal skin irritancy in atopic dermatitis and in atopy without dermatitis". Archives of Dermatology. 130 (11): 1402–7. doi:10.1001/archderm.130.11.1402. PMID 7979441.
  7. Magnusson B, Gilje O (1973). "Allergic contact dermatitis from a dish-washing liquid containing lauryl ether sulphate". Acta Dermato-Venereologica. 53 (2): 136–40. doi:10.2340/0001555553136140. PMID 4120956. S2CID 9398646.
  8. Van Haute N, Dooms-Goossens A (March 1983). "Shampoo dermatitis due to cocobetaine and sodium lauryl ether sulphate". Contact Dermatitis. 9 (2): 169. doi:10.1111/j.1600-0536.1983.tb04348.x. PMID 6851541. S2CID 42092578.
  9. Black RE, Hurley FJ, Havery DC (2001). "Occurrence of 1,4-dioxane in cosmetic raw materials and finished cosmetic products". Journal of AOAC International. 84 (3): 666–70. doi:10.1093/jaoac/84.3.666. PMID 11417628.
  10. FDA/CFSAN--Cosmetics Handbook Part 3: Cosmetic Product-Related Regulatory Requirements and Health Hazard Issues. Prohibited Ingredients and other Hazardous Substances: 9. Dioxane

External links

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