Hydrogen peroxide - urea

Hydrogen peroxide - urea
Names
Other names
Urea peroxide, percarbamide, UHP
Identifiers
124-43-6 YesY
ChEBI CHEBI:75178
ChemSpider 29034 YesY
Jmol interactive 3D Image
PubChem 31294
UNII 31PZ2VAU81 YesY
Properties
CH6N2O3
Molar mass 94.07 g·mol−1
Appearance White solid
Melting point 75 to 91.5 °C (167.0 to 196.7 °F; 348.1 to 364.6 K) (decomposes)
Pharmacology
ATC code D02AE01
Hazards
Safety data sheet External MSDS
Explosive, C
Flash point 60 °C (140 °F; 333 K)
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

Hydrogen peroxide - urea is a solid composed of equal amounts of hydrogen peroxide and urea. This compound is a white crystalline solid, which dissolves in water to give free hydrogen peroxide. Often called carbamide peroxide in the dental applications, it is used as a source of hydrogen peroxide for bleaching, disinfection, and oxidation.

Structure, properties, production

Akin to water of crystallization, hydrogen peroxide cocrystallizes with urea with the stoichiometry of 1:1. The compound is simply produced (on a scale of several hundred tonnes a year) by the dissolution of urea in excess concentrated hydrogen peroxide solution, followed by crystallization.[1] The laboratory synthesis is analogous.[2] Upon dissolving in various solvents, this 1:1 complex dissociates back to urea and hydrogen peroxide. So just like hydrogen peroxide, the adduct is an oxidizer. The solubility of commercial samples varies from 0.05 g/mL[3] to more than 0.6 g/mL.[4] The solid state structure of this adduct at the right has been determined by neutron diffraction.[5]

Applications

Disinfectant and bleaching agent

Hydrogen peroxide - urea is mainly used as a disinfecting and bleaching agent in cosmetics and pharmaceuticals.[1] As a drug, this compound is used in some preparations for the whitening of teeth.[1][6][7] It is also used to relieve minor inflammation of gums, oral mucosal surfaces and lips including canker sores and dental irritation,[8]and to emulsify and disperse ear wax.[9]

A pharmaceutical company, Elorac, has performed clinical trials for the use of carbamide peroxide for the treatment of acne vulgaris.[10]

Reagent in organic synthesis

In the laboratory, it is used as a more easily handled replacement for hydrogen peroxide.[2][11][12]

Safety

As an oxidizer, this compound is a skin, eye and respiratory irritant. At higher concentrations, it is corrosive and may cause burns if not used properly. If too much gel is used and left in contact with skin or gums, there is a risk of white chemical burns called blanching.

See also

References

  1. 1 2 3 Harald Jakob, Stefan Leininger, Thomas Lehmann, Sylvia Jacobi, Sven Gutewort (2005), "Peroxo Compounds, Inorganic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a19_177.pub2
  2. 1 2 Yu, Lei; Meng, Bo; Huang, Xian (2008). "Urea-Hydrogen Peroxide Complex: A Selective Oxidant in the Synthesis of 2-Phenylselenyl-1,3-butadienes". Synthetic Communications 38 (18): 3142. doi:10.1080/00397910802109224.
  3. ↑ Sigma-Aldrich specification sheet
  4. ↑ Chemicalland data sheet
  5. ↑ C.J. Fritchie, Jr.; R.K. McMullan; McMullan, R. K. (1981). "Neutron diffraction study of the 1:1 urea:hydrogen peroxide complex at 81 K". Acta Crystallogr., Sect. B 37 (5): 1086. doi:10.1107/S0567740881005116.
  6. ↑ Mokhlis, GR; Matis, BA; Cochran, MA; Eckert, GJ (2000). "A Clinical Evaluation of Carbamide Peroxide and Hydrogen Peroxide Whitening Agents during Daytime Use". Journal of the American Dental Association (1939) 131 (9): 1269–77. doi:10.14219/jada.archive.2000.0380. PMID 10986827.
  7. ↑ Toothwhitening from the UMD of New Jersey website
  8. ↑ Center for Integrative Medicine: Carbamide Peroxide from the University of Maryland Medical Center website Archived October 18, 2007 at the Wayback Machine
  9. ↑ "Carbamide peroxide (Into the ear)". Umm.edu. University of Maryland Medical Center. Retrieved July 29, 2015.
  10. ↑ Elorac Announces Clinical Results of Carbamide Peroxide Studies for the Treatment of Acne website
  11. ↑ Varma, Rajender S.; Naicker, Kannan P. (1999). "The Urea−Hydrogen Peroxide Complex: Solid-State Oxidative Protocols for Hydroxylated Aldehydes and Ketones (Dakin Reaction), Nitriles, Sulfides, and Nitrogen Heterocycles". Organic Letters 1 (2): 189. doi:10.1021/ol990522n.
  12. ↑ Harry Heaney, Francesca Cardona, Andrea Goti, "Hydrogen Peroxide–Urea" Encyclopedia of Reagents for Organic Synthesis 2008. doi:10.1002/047084289X.rh047.pub2

External links

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