Sodium laureth sulfate

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Sodium laureth sulfate
Sodium laureth sulfate structure.svg
Names
IUPAC name
α-Sulfo-ω-(dodecyloxy)-poly(oxyethane-1,2-diyl), sodium salt
Other names
Sodium lauryl ether sulfate
Sodium laureth sulphate
Sodium lauryl ether sulphate
Identifiers
AbbreviationsSLES
ChemSpider
  • sodium laureth-2 sulfate:none
ECHA InfoCard 100.036.281 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
  • 23665884  (sodium 2-dodecoxyethyl sulfate)
UNII
Properties
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.svgHealth 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 [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Sodium laureth sulfate (SLES), an accepted contraction of sodium lauryl ether sulfate (SLES), 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. [1] 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 [2] and reduces time the product takes to be rainfast, when enough of the herbicidal agent will be absorbed.

Contents

Its chemical formula is C H 3(CH2)11(OCH2CH2)nOSO3 Na . 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. [1] 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. [1]

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. [3]

Irritation

Like many other detergents, SLES is an irritant. [4] It has been shown that SLES causes eye or skin irritation in experiments conducted on animals and humans. [4] The related surfactant SLS is also a known irritant. [5] [6] [7] [8]

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, [9] and encourages manufacturers to remove 1,4-dioxane, though it is not required by federal law. [10]

See also

Related Research Articles

Sodium dodecyl sulfate (SDS) or sodium lauryl sulfate (SLS), sometimes written sodium laurilsulfate, is an organic compound with the formula CH3(CH2)11OSO3Na and structure H3C(CH2)11−O−S(=O)2−ONa+. It is an anionic surfactant used in many cleaning and hygiene products. This compound is the sodium salt of the 12-carbon organosulfate. Its hydrocarbon tail combined with a polar "headgroup" give the compound amphiphilic properties that make it useful as a detergent. SDS is also component of mixtures produced from inexpensive coconut and palm oils. SDS is a common component of many domestic cleaning, personal hygiene and cosmetic, pharmaceutical, and food products, as well as of industrial and commercial cleaning and product formulations.

<span class="mw-page-title-main">Surfactant</span> Substance that lowers the surface tension between a liquid and another material

Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word "surfactant" is a blend of surface-active agent, coined in 1950. As they consist of a water-repellent and a water-attracting part, they enable water and oil to mix; they can form foam and facilitate the detachment of dirt.

<span class="mw-page-title-main">Contact dermatitis</span> Inflammation from allergen or irritant exposure

Contact dermatitis is a type of acute or chronic inflammation of the skin caused by exposure to chemical or physical agents. Symptoms of contact dermatitis can include itchy or dry skin, a red rash, bumps, blisters, or swelling. These rashes are not contagious or life-threatening, but can be very uncomfortable.

Ammonium lauryl sulfate (ALS) is the common name for ammonium dodecyl sulfate (CH3(CH2)10CH2OSO3NH4). The anion consists of a nonpolar hydrocarbon chain and a polar sulfate end group. The combination of nonpolar and polar groups confers surfactant properties to the anion: it facilitates dissolution of both polar and non-polar materials. This salt is classified as a sulfate ester. It is made from coconut or palm kernel oil for use primarily in shampoos and body-wash as a foaming agent. Lauryl sulfates are very high-foam surfactants that disrupt the surface tension of water in part by forming micelles at the surface-air interface.

In organic chemistry, ethoxylation is a chemical reaction in which ethylene oxide adds to a substrate. It is the most widely practiced alkoxylation, which involves the addition of epoxides to substrates.

<span class="mw-page-title-main">1,4-Dioxane</span> Chemical compound

1,4-Dioxane is a heterocyclic organic compound, classified as an ether. It is a colorless liquid with a faint sweet odor similar to that of diethyl ether. The compound is often called simply dioxane because the other dioxane isomers are rarely encountered.

<span class="mw-page-title-main">Glass Plus</span>

Glass Plus is a glass and multi-surface cleaner.

Dodecanol, or lauryl alcohol, is an organic compound produced industrially from palm kernel oil or coconut oil. It is a fatty alcohol. Sulfate esters of lauryl alcohol, especially sodium lauryl sulfate, are very widely used as surfactants. Sodium lauryl sulfate and the related dodecanol derivatives ammonium lauryl sulfate and sodium laureth sulfate are all used in shampoos. Dodecanol is tasteless, colorless, and has a floral odor.

Sodium pareth sulfate, also known as sodium alkylpoly(oxyethylene) sulfate, is a surfactant found in some detergent products such as hand or body washes, but not as commonly as other chemicals such as sodium laureth sulfate (SLES). It is the sodium salt of a sulfated polyethylene glycol ether.

A foaming agent is a material such as a surfactant or a blowing agent that facilitates the formation of foam. A surfactant, when present in small amounts, reduces surface tension of a liquid or increases its colloidal stability by inhibiting coalescence of bubbles. A blowing agent is a gas that forms the gaseous part of the foam.

<span class="mw-page-title-main">Isethionic acid</span> Chemical compound

Isethionic acid is an organosulfur compound containing an alkylsulfonic acid located beta to a hydroxy group. Its discovery is generally attributed to Heinrich Gustav Magnus, who prepared it by the action of solid sulfur trioxide on ethanol in 1833. It is a white water-soluble solid used in the manufacture of certain surfactants and in the industrial production of taurine. It is most commonly available in the form of its sodium salt.

Sodium myreth sulfate is a mixture of organic compounds with both detergent and surfactant properties. It is found in many personal care products such as soaps, shampoos, and toothpaste. It is an inexpensive and effective foaming agent. Typical of many detergents, sodium myreth sulfate consists of several closely related compounds. Sometimes the number of ethylene glycol ether units (n) is specified in the name as myreth-n sulfate, for example myreth-2 sulfate.

Cocamidopropyl betaine (CAPB) is a mixture of closely related organic compounds derived from coconut oil and dimethylaminopropylamine. CAPB is available as a viscous pale yellow solution and it is used as a surfactant in personal care products and animal husbandry. The name reflects that the major part of the molecule, the lauric acid group, is derived from coconut oil. Cocamidopropyl betaine to a significant degree has replaced cocamide DEA.

<span class="mw-page-title-main">Benzethonium chloride</span> Chemical compound

Benzethonium chloride, also known as hyamine is a synthetic quaternary ammonium salt. This compound is an odorless white solid, soluble in water. It has surfactant, antiseptic, and anti-infective properties, and it is used as a topical antimicrobial agent in first aid antiseptics. It is also found in cosmetics and toiletries such as soap, mouthwashes, anti-itch ointments, and antibacterial moist towelettes. Benzethonium chloride is also used in the food industry as a hard surface disinfectant.

<span class="mw-page-title-main">Organosulfate</span> Organic compounds of the form R–O–SO₃ (charge –1)

In organosulfur chemistry, organosulfates are a class of organic compounds sharing a common functional group with the structure R−O−SO−3. The SO4 core is a sulfate group and the R group is any organic residue. All organosulfates are formally esters derived from alcohols and sulfuric acid although many are not prepared in this way. Many sulfate esters are used in detergents, and some are useful reagents. Alkyl sulfates consist of a hydrophobic hydrocarbon chain, a polar sulfate group and either a cation or amine to neutralize the sulfate group. Examples include: sodium lauryl sulfate and related potassium and ammonium salts.

Within chemical compound surfactants, pentaethylene glycol monododecyl ether (C12E5) is a nonionic surfactant. It is formed by the ethoxylation chemical reaction of dodecanol to give a material with 5 repeat units of ethylene glycol.

<span class="mw-page-title-main">Shampoo</span> Hair care product

Shampoo is a hair care product, typically in the form of a viscous liquid, that is used for cleaning hair. Less commonly, shampoo is available in solid bar format. Shampoo is used by applying it to wet hair, massaging the product into the scalp, and then rinsing it out. Some users may follow a shampooing with the use of hair conditioner.

A soap substitute is a natural or synthetic cleaning product used in place of soap or other detergents, typically to reduce environmental impact or health harms or provide other benefits.

Zendium is a brand of toothpaste marketed by Unilever in Austria, Belgium, Croatia, Czech Republic, France, Germany, Hungary, Italy, the Middle East, the Netherlands, Scandinavia, Slovakia and Switzerland.

Hair washing without commercial shampoo, sometimes called no poo, includes water-only hair washing or hair washing with non-commercial products, such as baking soda and vinegar. Advocates argue that commercial shampoo is an unnecessary expense and may contain harmful ingredients.

References

  1. 1 2 3 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. 1 2 "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