Ethylbenzene hydroperoxide

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Ethylbenzene hydroperoxide
Ethylbenzene hydroperoxide.svg
Names
IUPAC name
1-hydroperoxyethylbenzene
Other names
α-methylbenzyl hydroperoxide, 1-phenylethyl hydroperoxid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.019.402 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 221-341-3
PubChem CID
UNII
  • InChI=1S/C8H10O2/c1-7(10-9)8-5-3-2-4-6-8/h2-7,9H,1H3
    Key: GQNOPVSQPBUJKQ-UHFFFAOYSA-N
  • CC(C1=CC=CC=C1)OO
Properties
Appearancecolorless liquid
Density 1.07500 g/cm3
Boiling point 45 °C (113 °F; 318 K) 0.05 torr
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ethylbenzene hydroperoxide is the organic compound with the formula C6H5CH(O2H)CH3. A colorless liquid, EBHP is a common hydroperoxide. It has been used as an O-atom donor in organic synthesis. It is chiral. Together with tert-butyl hydroperoxide and cumene hydroperoxide, ethylbenzene hydroperoxide is important commercially. [1]

The compound is produced by direct reaction of ethylbenzene with oxygen, an autoxidation. [2]

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tert-Butyl hydroperoxide (tBuOOH) is the organic compound with the formula (CH3)3COOH. It is one of the most widely used hydroperoxides in a variety of oxidation processes, like the Halcon process. It is normally supplied as a 69–70% aqueous solution. Compared to hydrogen peroxide and organic peracids, tert-butyl hydroperoxide is less reactive and more soluble in organic solvents. Overall, it is renowned for the convenient handling properties of its solutions. Its solutions in organic solvents are highly stable.

<span class="mw-page-title-main">Cumene hydroperoxide</span> Aromatic organic chemical compound

Cumene hydroperoxide is the organic compound with the formula C6H5C(CH3)2OOH. An oily liquid, it is classified as an organic hydroperoxide. Products of decomposition of cumene hydroperoxide are methylstyrene, acetophenone, and 2-phenyl-2-propanol.

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<span class="mw-page-title-main">Dicumyl peroxide</span> Chemical compound

Dicumyl peroxide is an organic compound with the formula (C6H5CMe2O)2 (Me = CH3). Classified as a dialky peroxide, it is produced on a large scale industrially for use in polymer chemistry. It serves as an initiator and crosslinking agent in the production of low density polyethylene.

References

  1. Roger A. Sheldon (1983). "Synthesis and uses of alkyl hydroperoxides and dialkyl peroxides". In Patai, Saul (ed.). Syntheses and Uses of Hydroperoxides and Dialkylperoxides. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. pp. 161–200. doi:10.1002/9780470771730.ch6. ISBN   978-0-471-10218-2.
  2. Hermans, Ive; Peeters, Jozef; Jacobs, Pierre A. (2007). "Autoxidation of Ethylbenzene: The Mechanism Elucidated". The Journal of Organic Chemistry. 72 (8): 3057–3064. doi:10.1021/jo070040m. PMID   17362045.