Lauryldimethylamine oxide

Lauryldimethylamine oxide

Names
IUPAC name N,N-Dimethyldodecan-1-amine oxide
Other names Lauramine oxide; Dodecyldimethylamine oxide; Dimethyldodecylamine-N-oxide
Identifiers
CAS Number	1643-20-5
ChemSpider	14688
EC Number	216-700-6
Jmol 3D model	Interactive image
PubChem	15433
InChI InChI=1S/C14H31NO/c1-4-5-6-7-8-9-10-11-12-13-14-15(2,3)16/h4-14H2,1-3H3 Key: SYELZBGXAIXKHU-UHFFFAOYSA-N InChI=1/C14H31NO/c1-4-5-6-7-8-9-10-11-12-13-14-15(2,3)16/h4-14H2,1-3H3 Key: SYELZBGXAIXKHU-UHFFFAOYAJ
SMILES CCCCCCCCCCCC[N+](C)(C)[O-]
Properties
Chemical formula	C14H31NO
Molar mass	229.41 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Lauryldimethylamine oxide, also known as dodecyldimethylamine oxide or DDAO, (also N,N-Dimethyldodecylamine N-oxide), is an amine oxide surfactant. It is one of the most frequently-used surfactants of this type.^[1]

At high concentrations, DDAO forms liquid crystalline phases.^[2] Despite having only one polar atom that is able to interact with water - the oxygen atom (the quaternary nitrogen atom is hidden from intermolecular interactions), DDAO is a strongly hydrophilic surfactant: it forms normal micelles and normal liquid crystalline phases. High hydrophilicity of this surfactant can be explained by the fact that it forms very strong hydrogen bonds with water: the energy of DDAO - water hydrogen bond is about 50 kJ/mol.^[3]

References

1. Friedli, Floyd E (2001). Detergency of Specialty Surfactants. New York, NY: Dekker. ISBN 0-8247-0491-6.
2. Kocherbitov, V., Söderman, O. (2006). "Hydration of Dimethyldodecylamine-N-Oxide: Enthalpy and Entropy Driven Processes". J.Phys.Chem.B. 110 (27): 13649–13655. doi:10.1021/jp060934v. PMID 16821893.
3. Kocherbitov, V.; Veryazov, V.; Söderman, O. (2007). "Hydration of Trimethylamine-N-oxide and of Dimethyldodecylamine-N-oxide: An Ab Initio study". J. Molec. Struct.: Theochem. 808: 111–118. doi:10.1016/j.theochem.2006.12.043.