Methyl hydroperoxide

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Methyl hydroperoxide
Methyl hydroperoxide.svg
Names
IUPAC name
Methaneperoxol
Other names
Hydroperoxide, methyl
Methane hydroperoxide
Methyl hydrogen peroxide
Hydroperoxymethane
Identifiers
3D model (JSmol)
PubChem CID
  • InChI=1S/CH4O2/c1-3-2/h2H,1H3
    Key: MEUKEBNAABNAEX-UHFFFAOYSA-N
  • COO
Properties
CH4O2
Molar mass 48.041 g·mol−1
Appearancecolorless liquid
Density 0.9967 g/cm3 at 15°C
Melting point <25 °C
Boiling point 46 °C (115 °F; 319 K)
Miscible in water and diethyl ether
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
explosive
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 organic hydroperoxide, methyl hydroperoxide is an intermediate in the oxidation of methane in the atmosphere. [1] When condensed or in concentrated form methyl hydroperoxide is rather explosive, unlike tertiary hydroperoxides such as tert-butylhydroperoxide. [2] Its laboratory preparation was first reported in 1929. [3]

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In organic chemistry, ethers are a class of 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 or aryl 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". Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

<span class="mw-page-title-main">Ketene</span> Organic compound of the form >C=C=O

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In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula CH3. In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many organic compounds. It is a very stable group in most molecules. While the methyl group is usually part of a larger molecule, bounded to the rest of the molecule by a single covalent bond, it can be found on its own in any of three forms: methanide anion, methylium cation or methyl radical. The anion has eight valence electrons, the radical seven and the cation six. All three forms are highly reactive and rarely observed.

<span class="mw-page-title-main">Aldehyde</span> Organic compound containing the functional group R−CH=O

In organic chemistry, an aldehyde is an organic compound containing a functional group with the structure R−CH=O. The functional group itself can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are common and play important roles in the technology and biological spheres.

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<span class="mw-page-title-main">Thioester</span> Organosulfur compounds of the form R–SC(=O)–R’

In organic chemistry, thioesters are organosulfur compounds with the molecular structure R−C(=O)−S−R’. They are analogous to carboxylate esters with the sulfur in the thioester replacing oxygen in the carboxylate ester, as implied by the thio- prefix. They are the product of esterification of a carboxylic acid with a thiol. In biochemistry, the best-known thioesters are derivatives of coenzyme A, e.g., acetyl-CoA. The R and R' represent organyl groups, or H in the case of R.

<span class="mw-page-title-main">Aminal</span> Organic compound or group with two amines bound to the same carbon

In organic chemistry, an aminal or aminoacetal is a functional group or type of organic compound that has two amine groups attached to the same carbon atom: −C(NR2)(NR2)−.. A common aminal is bis(dimethylamino)methane, a colorless liquid that is prepared by the reaction of dimethylamine and formaldehyde:

<span class="mw-page-title-main">Sulfoxide</span> Organic compound containing a sulfinyl group (>SO)

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<span class="mw-page-title-main">Sulfonium</span> Cation of the form [SR3]+

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In organic chemistry, organic peroxides are organic compounds containing the peroxide functional group. If the R′ is hydrogen, the compounds are called hydroperoxides, which are discussed in that article. 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 polymerization, such as the acrylic, unsaturated polyester, and vinyl ester 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 explosively combust. Organic peroxides, like their inorganic counterparts, are often powerful bleaching agents.

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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.

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

Triphenylmethanol is an organic compound. It is a white crystalline solid that is insoluble in water and petroleum ether, but well soluble in ethanol, diethyl ether, and benzene. In strongly acidic solutions, it produces an intensely yellow color, due to the formation of a stable "trityl" carbocation. Many derivatives of triphenylmethanol are important dyes.

Di-<i>tert</i>-butyl peroxide DTBP: organic compound consisting of a peroxide group bonded to two tert-butyl groups

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<span class="mw-page-title-main">Ortho ester</span> Chemical group with the structure RC(OR)3

In organic chemistry, an ortho ester is a functional group containing three alkoxy groups attached to one carbon atom, i.e. with the general formula RC(OR′)3. Orthoesters may be considered as products of exhaustive alkylation of unstable orthocarboxylic acids and it is from these that the name 'ortho ester' is derived. An example is ethyl orthoacetate, CH3C(OCH2CH3)3, more correctly known as 1,1,1-triethoxyethane.

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

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, 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 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 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.

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:

<span class="mw-page-title-main">Ethylbenzene hydroperoxide</span> Chemical compound

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.

<span class="mw-page-title-main">Organic thiocyanates</span>

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References

  1. Logan, Jennifer A.; Prather, Michael J.; Wofsy, Steven C.; McElroy, Michael B. (1981). "Tropospheric chemistry: A global perspective". Journal of Geophysical Research. 86 (C8): 7210. Bibcode:1981JGR....86.7210L. doi:10.1029/JC086iC08p07210.
  2. 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.
  3. Rieche, Alfred; Hitz, Fritz (1929). "Über Monomethyl-hydroperoxyd)". Berichte der Deutschen Chemischen Gesellschaft. 62 (8): 2458–2474. doi:10.1002/cber.19290620888.