Sodium dodecyl sulfate 

Sodium dodecyl sulfate
IUPAC name Sodium dodecyl sulfate
Other names Sodium monododecyl sulfate; Sodium lauryl sulfate; Sodium monolauryl sulfate; Sodium dodecanesulfate; dodecyl alcohol, hydrogen sulfate, sodium salt; n-dodecyl sulfate sodium; Sulfuric acid monododecyl ester sodium salt;
Identifiers
CAS number 151-21-3
SMILES
 
Properties
Molecular formula NaC12H25SO4
Molar mass 288.38 g mol−1
Density 1.01 g/cm³
Melting point

206 °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox references

Sodium lauryl sulfate (SLS) or sodium dodecyl sulfate (SDS or NaDS) (C12H25SO4Na) is an anionic surfactant that is used in industrial products including engine degreasers, floor cleaners, and car wash soaps; as well as in household products such as toothpastes, shampoos, shaving foams, some dissolvable aspirins, fiber therapy caplets, and bubble baths for its thickening effect and its ability to create a lather. The molecule has a tail of 12 carbon atoms, attached to a sulfate group, giving the molecule the amphiphilic properties required of a detergent.

Contents

Preparation

Sodium lauryl sulfate is prepared by esterification of sulfuric acid with dodecanol (lauryl alcohol, C12H25OH), followed by neutralization with sodium carbonate.1 It is used in both industrially produced and home-made cosmetics.

Applications

Sodium lauryl sulfate is probably the most researched anionic surfactant compound. Like all detergent surfactants (including soaps), sodium lauryl sulfate removes oils from the skin, and can cause skin and eye irritation. The critical micelle concentration (CMC) in pure water at 25°C is 0.0082 M2, and the aggregation number at this concentration is usually considered to be about 623. The micelle ionization fraction (α) is around 0.3 (or 30%).4

It has recently found application as a surfactant in gas hydrate or methane hydrate formation reactions, increasing the rate of formation as much as 700 times.5

SDS-PAGE

Main article: SDS-PAGE

Sodium lauryl sulfate is commonly used in preparing proteins for electrophoresis in the SDS-PAGE technique.6 This compound works by disrupting non-covalent bonds in the proteins, denaturing them, and causing the molecules to lose their native shape (conformation). Also, anions of SLS bind to the main peptide chain at a ratio of one SLS anion for every two amino acid residues. This effectively imparts a negative charge on the protein that is proportional to the mass of that protein (about 1.4 g SLS/g protein).

This new negative charge is significantly greater than the original charge of that protein. The electrostatic repulsion that is created by binding of SLS causes proteins to unfold into a rod-like shape thereby eliminating differences in shape as a factor for separation in the gel.

Reactions

SLS can be converted by ethoxylation to sodium laureth sulfate (sodium lauryl ether sulfate; SLES), which is less harsh on the skin, probably because it is not as much of a protein denaturant as is the unethoxylated substance.citation needed

Safety

When handling SLS in its solid form use extreme caution; the compound easily particalizes into the air. If inhaled, it can cause a serious choking hazard.

A number of health concerns about SLS have been raised in published reports.789 These studies indicate that:

See also

References

  1. ^ "Sodium Lauryl Sulfate". Chemicalland21.
  2. ^ P. Mukerjee and K. J. Mysels, "Critical Micelle Concentration of Aqueous Surfactant Systems", NSRDS-NBS 36, US. Government Printing Office, Washington,.D.C., 197 1.
  3. ^ N.J. Turro. A. Yekta, J. Am. Chem. Soc., 1978, 100, 5951
  4. ^ Barney L. Bales, Luis Messina, Arwen Vidal, Miroslav Peric, and Otaciro Rangel Nascimento (1998). "Precision Relative Aggregation Number Determinations of SDS Micelles Using a Spin Probe. A Model of Micelle Surface Hydration". J. Phys. Chem. B 102 (50): 10347–10358. doi:10.1021/jp983364a. 
  5. ^ Kazuyoshi Watanabe, Shuntaro Imai and Yasuhiko H. Mori. Surfactant effects on hydrate formation in an unstirred gas/liquid system: An experimental study using HFC-32 and sodium dodecyl sulfate. Department of Mechanical Engineering, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522. Japan.Chemical Engineering Science. Volume 60, Issue 17, September 2005, Pages 4846-4857. Abstract
  6. ^ The acronym expands to "sodium dodecyl sulfate-polyacrylamide gel electrophoresis.
  7. ^ Agner T. Susceptibility of atopic dermatitis patients to irritant dermatitis caused by sodium lauryl sulphate. Acta Derm Venereol. 1991;71(4):296-300. PMID 1681644
  8. ^ A. Nassif, S. C. Chan, F. J. Storrs and J. M. Hanifin. Abstract: Abnormal skin irritancy in atopic dermatitis and in atopy without dermatitis. Arch Dermatol. November 1994;130(11):1402. Abstract
  9. ^ a b Marrakchi S, Maibach HI. Sodium lauryl sulfate-induced irritation in the human face: regional and age-related differences. Skin Pharmacol Physiol. 2006;19(3):177-80. Epub 2006 May 4. PMID 16679819
  10. ^ CIR publication. Final Report on the Safety Assessment of Sodium Lauryl Sulfate and Ammonium Lauryl Sulfate. Journal of the American College of Toxicology. 1983 Vol. 2 (No. 7) pages 127-181.
  11. ^ Loffler H, Effendy I. Skin susceptibility of atopic individuals. Department of Dermatology, University of Marburg, Germany. Contact Dermatitis. 1999 May;40(5):239-42. PMID 10344477
  12. ^ Herlofson B, Barkvoll P (1994). "Sodium lauryl sulfate and recurrent aphthous ulcers. A preliminary study." (PDF). Acta Odontol Scand 52 (5): 257–9. doi:10.3109/00016359409029036. PMID 7825393, http://www.healthychoices.ukhq.co.uk/Articles/SLS-Ulcers.pdf. 
  13. ^ Chahine L, Sempson N, Wagoner C. The effect of sodium lauryl sulfate on recurrent aphthous ulcers: a clinical study. Compend Contin Educ Dent. 1997 Dec;18(12):1238-40. PMID 9656847
  14. ^ Herlofson BB, Barkvoll P. The effect of two toothpaste detergents on the frequency of recurrent aphthous ulcers. Acta Odontol Scand. 1996 Jun;54(3):150-3. PMID 8811135
  15. ^ Healy C, Paterson M, Joyston-Bechal S, Williams D, Thornhill M (1999). "The effect of a sodium lauryl sulfate-free dentifrice on patients with recurrent oral ulceration.". Oral Dis 5 (1): 39–43. doi:10.1111/j.1365-2133.2005.06490.x. PMID 10218040. 

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