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)
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).
Infobox references

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]

Related Research Articles

Ether Class of organic compounds

Ethers are a class of organic compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula R–O–R′, where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether" (CH3–CH2–O–CH2–CH3). Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

Ketene

A ketene is an organic compound of the form R′R″C=C=O, where R and R' are two arbitrary monovalent chemical groups. The name may also refer to the specific compound ethenone H2C=C=O, the simplest ketene.

Aldehyde Type of carbonyl coumpound

In chemistry, an alde is an organic compound containing a functional group with the structure −C(H)=O. The functional group itself is known as an aldehyde or formyl group. Aldehydes are common and play important roles in the technology and biological spheres.

Acetophenone Chemical compound

Acetophenone is the organic compound with the formula C6H5C(O)CH3 (also represented by the pseudoelement symbols PhAc or BzMe). It is the simplest aromatic ketone. This colorless, viscous liquid is a precursor to useful resins and fragrances.

Carbonyl group Functional group (C=O)

In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containing a carbonyl group is often referred to as a carbonyl compound.

The cumene process is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term stems from cumene, the intermediate material during the process. It was invented by R. Ūdris and P. Sergeyev in 1942 (USSR)., and independently by Heinrich Hock in 1944

Ethyl group Functional group in organic chemistry

In chemistry, an ethyl group is an alkyl substituent derived from ethane (C2H6). It has the formula –CH2CH3 and is very often abbreviated Et. Ethyl is used in the IUPAC nomenclature of organic chemistry for a saturated two-carbon moiety in a molecule, while the prefix "eth-" is used to indicate the presence of two carbon atoms in the molecule.

Epoxide

An epoxide is a cyclic ether with a three-atom ring. This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and nonpolar, and often volatile.

Propylene oxide Chemical compound

Propylene oxide is an acutely toxic and carcinogenic organic compound with the molecular formula CH3CHCH2O. This colorless volatile liquid with an odor similar to ether, is produced on a large scale industrially. Its major application is its use for the production of polyether polyols for use in making polyurethane plastics. It is a chiral epoxide, although it is commonly used as a racemic mixture.

Diethyl ether peroxide Chemical compound

Diethyl ether hydroperoxide is the organic compound with the formula C2H5OCH(OOH)CH3. It is a colorless, distillable liquid. Diethyl ether hydroperoxide and its condensation products are blamed for the explosive organic peroxides that slowly form upon exposure of diethyl ether to ambient air and temperature conditions.

Ethylbenzene Chemical compound

Ethylbenzene is an organic compound with the formula C6H5CH2CH3. It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as an intermediate in the production of styrene, the precursor to polystyrene, a common plastic material. In 2012, more than 99% of ethylbenzene produced was consumed in the production of styrene.

Organic peroxides Type of organic compounds

Organic peroxides are organic compounds containing the peroxide functional group (ROOR′). If the R′ is hydrogen, the compounds are called hydroperoxides, which are discussed in that article. Peresters are the peroxy analog of esters and have general structure RC(O)OOR. The O−O bond of peroxides easily breaks, producing free radicals of the form RO. Thus, organic peroxides are useful as initiators for some types of polymerisation, such as the epoxy resins used in glass-reinforced plastics. MEKP and benzoyl peroxide are commonly used for this purpose. However, the same property also means that organic peroxides can either intentionally or unintentionally initiate explosive polymerisation in materials with unsaturated chemical bonds, and this process has been used in explosives. Organic peroxides, like their inorganic counterparts, are powerful bleaching agents.

Autoxidation refers to oxidations brought about by reactions with oxygen at normal temperatures, without the intervention of flame or electric spark. The term is usually used to describe the degradation of organic compounds in air at ambient temperatures. Many common phenomena can be attributed to autoxidation, such as food going rancid, the 'drying' of varnishes and paints, and the perishing of rubber. It is also an important concept in both industrial chemistry and biology. Autoxidation is therefore a fairly broad term and can encompass examples of photooxygenation and catalytic oxidation.

Hydroperoxide Class of chemical compounds

Hydroperoxides or peroxols are compounds containing the hydroperoxide functional group (ROOH). If the R is organic, the compounds are called organic hydroperoxides. Such compounds are a subset of organic peroxides, which have the formula ROOR. Organic hydroperoxides can either intentionally or unintentionally initiate explosive polymerisation in materials with unsaturated chemical bonds.

2-Ethylanthraquinone Chemical compound

2-Ethylanthraquinone is an organic compound that is a derivative of anthraquinone. This pale yellow solid is used in the industrial production of hydrogen peroxide (H2O2).

<i>tert</i>-Butyl hydroperoxide Chemical compound

tert-Butyl hydroperoxide (tBuOOH) is the organic compound with the formula (CH3)3COOH. It is a hydroperoxide, in fact one of the most widely used in a variety of oxidation processes, for example 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, 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.

Cumene hydroperoxide Aromatic organic chemical compound

Cumene hydroperoxide is the organic compound with the formula C6H5CMe2OOH (Me = CH3). An oily liquid, it is classified as an organic hydroperoxide. Products of decomposition of cumene hydroperoxide are methylstyrene, acetophenone, and cumyl alcohol. Its formula is C6H5C(CH3)2OOH.

Catalytic oxidation are processes that oxidize compounds using catalysts. Common applications involve oxidation of organic compounds by the oxygen in air. Such processes are conducted on a large scale for the remediation of pollutants, production of valuable chemicals, and the production of energy. In petrochemistry, high-value intermediates such as carboxylic acids, aldehydes, ketones, epoxides, and alcohols are obtained by partial oxidation of alkanes and alkenes with dioxygen. These intermediates are essential to the production of consumer goods. Partial oxidation presents two challenges. The first is that the most favored reaction between oxygen and hydrocarbons is combustion. The second challenge is the considerable difficulty to activate dioxygen, viz. the splitting of the molecule into its constituent atoms, which has an energy barrier of 498 kJ/mol. The usual strategy to activate oxygen in a controlled manner is to use molecular hydrogen or carbon monoxide as sacrificial reductants in presence of a heterogeneous catalyst, such that the activation barrier is lowered to < 10 kJ/mol and hence milder reaction conditions are required.

In chemistry, the Halcon process refers to technology for the production of propylene oxide by oxidation of propylene with tert-butyl hydroperoxide. The reaction requires metal catalysts, which typically contain molybdenum:

Methyl hydroperoxide Chemical compound

Methyl hydroperoxide is the organic compound with the formula CH3OOH. It is a volaltile colorless liquid. In addition to being of theoretical interest as the simplest hydroperoxide, methyl hydroperoxide is an intermediate in the oxidation of methane in the atmosphere. It is rather explosive, unlike related tertiary hydroperoxides. Its laboratory preparation was first reported in 1929.

References

  1. Roger A. Sheldon (1983). Patai, Saul (ed.). Syntheses and Uses of Hydroperoxides and Dialkylperoxides. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. doi:10.1002/9780470771730.ch6.
  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.