Hydrogen peroxide - urea

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Hydrogen peroxide - urea
Names
IUPAC name
Hydrogen peroxide — urea (1/1)
Systematic IUPAC name
Peroxol — carbonyl diamide (1/1)
Other names
Urea peroxide, percarbamide, UHP
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
ECHA InfoCard
 100.004.275 Edit this at Wikidata
UNII
  • InChI=1S/CH4N2O.H2O2/c2-1(3)4;1-2/h(H4,2,3,4);1-2H checkY
    Key: AQLJVWUFPCUVLO-UHFFFAOYSA-N checkY
  • O=C(N)N.OO
Properties
CH6N2O3
Molar mass 94.070 g·mol−1
Appearance White solid
Density 1.50 g/cm3
Melting point 75 to 91.5 °C (167.0 to 196.7 °F; 348.1 to 364.6 K) (decomposes)
Pharmacology
D02AE01 (WHO)
Hazards
GHS labelling:[1]
GHS03: OxidizingGHS05: Corrosive
Danger
H272, H315, H318
P210, P220, P264, P280, P302+P352, P305+P351+P338
Flash point 60 °C (140 °F; 333 K)
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Hydrogen peroxide - urea (also called Hyperol, artizone, urea hydrogen peroxide, and UHP) is a white

oxidation
.

Production

For the preparation of the complex, urea is dissolved in 30% hydrogen peroxide (molar ratio 2:3) at temperatures below 60 °C. upon cooling this solution, hydrogen peroxide - urea precipitates in the form of small platelets.[2]

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.[3] The laboratory synthesis is analogous.[4]

Structure and properties

The solid state structure of this adduct has been determined by neutron diffraction.[5]

Hydrogen peroxide - urea is a readily water-soluble, odorless, crystalline solid, which is available as white powder or colorless needles or platelets.

oxidizer but the release at room temperature in the presence of catalysts proceeds in a controlled manner. Thus the compound is suitable as a safe substitute for the unstable aqueous solution of hydrogen peroxide. Because of the tendency for thermal decomposition, which accelerates at temperatures above 82 °C,[6]
it should not be heated above 60 °C, particularly in pure form.

The solubility of commercial samples varies from 0.05 g/mL[7] to more than 0.6 g/mL.[8]

Applications

Disinfectant and bleaching agent

Hydrogen peroxide - urea is mainly used as a disinfecting and bleaching agent in cosmetics and pharmaceuticals.

canker sores and dental irritation,[11] and to emulsify and disperse earwax.[12]

Carbamide peroxide is also suitable as a disinfectant, e.g. for germ reduction on contact lens surfaces or as an antiseptic for mouthwashes, ear drops or for superficial wounds and ulcers.

Reagent in organic synthesis

In the laboratory, it is used as a more easily handled replacement for

cis-butenedioic anhydride[15] or inorganic catalysts such as sodium tungstate.[16]

Reaktionen mit Carbamidperoxid
Reaktionen mit Carbamidperoxid

[verification needed]

It converts thiols selectively to disulfides,[15] secondary alcohols to ketones,[16] sulfides to sulfoxides and sulfones,[17] nitriles to amides,[17][18] and N-heterocycles to amine oxides.[17][19]

Reaktionen von Methoxyphenolen mit UHP
Reaktionen von Methoxyphenolen mit UHP

Hydroxybenzaldehydes are converted to

Dakin reaction)[17][20] and give, under suitable conditions, the corresponding benzoic acids.[20]

Baeyer-Villiger-Oxidation mit UHP
Baeyer-Villiger-Oxidation mit UHP

It oxidizes ketones to esters, in particular cyclic ketones, such as substituted cyclohexanones[21] or cyclobutanones[22] to give lactones (Baeyer–Villiger oxidation).

The epoxidation of various alkenes in the presence of benzonitrile yields oxiranes in yields of 79 to 96%.[23]

Epoxidierung von Cyclohexen mit UHP
Epoxidierung von Cyclohexen mit UHP

The oxygen atom transferred to the alkene originates from the peroxoimide acid formed intermediately from benzonitrile. The resulting imidic acid tautomerizes to the benzamide.

Safety

The compound acts as a strong oxidizing agent and can cause skin irritation and severe eye damage.

high explosive, capable of detonation by strong impulse under heavy confinement.[25][26]

See also

References

  1. ^ GHS: Sigma-Aldrich 289132
  2. ^
    doi:10.1021/ja01851a007
  3. ^
    ISBN 978-3527306732
    .
  4. ^
    S2CID 98323467
    .
  5. doi:10.1107/S0567740881005116
    .
  6. ISBN 978-0471936237. {{cite book}}: |periodical= ignored (help
    )
  7. ^ Sigma-Aldrich specification sheet
  8. ^ Chemicalland data sheet
  9. PMID 10986827. Archived from the original
    on 2013-02-23.
  10. ^ Toothwhitening Archived 2008-03-17 at the Wayback Machine from the UMD of New Jersey website
  11. ^ Center for Integrative Medicine: Carbamide Peroxide from the University of Maryland Medical Center website Archived October 18, 2007, at the Wayback Machine
  12. ^ "Ear Drops GENERIC NAME(S): CARBAMIDE PEROXIDE". WebMD. Retrieved July 3, 2021.
  13. doi:10.1021/ol990522n
    .
  14. doi:10.1002/047084289X.rh047.pub2
  15. ^
    PMID 18007530
  16. ^ a b M. Lukasiewicz; D. Bogdal; J. Pielichowski. "Microwave-assisted oxidation of alcohols using urea hydrogen peroxide". 8th International Electronic Conference on Synthetic Organic Chemistry. ECSOC-8. Retrieved 2016-05-10.
  17. ^
    doi:10.1021/ol990522n
  18. ^ WO patent 2012069948, V. Mascitti, K.F. McClure, M.J. Munchhof, R.P. Robinson, Jr., "4-(5-Cyano-pyrazol-1-yl)-piperidine derivatives as GPR 119 modulators", issued 2012-5-31, assigned to Pfizer Inc. 
  19. doi:10.1016/j.tetlet.2008.09.124
  20. ^
    doi:10.1016/S0040-4039(01)01332-6
  21. doi:10.1039/B618175A
  22. doi:10.1016/S0040-4039(02)00831-6
  23. S2CID 93770740
  24. ^ "Hydrogen peroxide urea SDS". merckmillipore.com. 16 May 2023.
  25. S2CID 244899815
    .
  26. S2CID 257196173
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Hydrogen_peroxide_-_urea&oldid=1192582121"