Diethyl ether peroxide

Diethyl ether peroxide: Diethyl ether hydroperoxide

Identifiers

CAS number 18321-53-4

ChemSpider 19985446^Y

Jmol-3D images Image 1
Image 2

SMILES

CCOC(OO)C
CC(OCC)OO

InChI

InChI=1S/C4H10O3/c1-3-6-4(2)7-5/h4-5H,3H2,1-2H3^Y
Key: CXWWPQGYBJCHJL-UHFFFAOYSA-N^Y
InChI=1/C4H10O3/c1-3-6-4(2)7-5/h4-5H,3H2,1-2H3
Key: CXWWPQGYBJCHJL-UHFFFAOYAS

Properties

Molecular formula C₄H₁₀O₃

Molar mass 106.12 g/mol

Density 1.005 g/cm³

Boiling point
62 - 64 °C at 18.7 hPa (reduced pressure)

Hazards

Main hazards Explosive

NFPA 704

4

2

4

Y ether peroxide (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Diethyl ether peroxides are a class of organic peroxides that slowly form in diethyl ether upon storage under air, light, or in the presence of metal by autoxidation.

Contents

1 Diethyl ether hydroperoxide

2 Diethyl ether peroxide

3 Tests

4 Degradation

5 References

Diethyl ether hydroperoxide

Diethyl ether hydroperoxide (CH₃-CH₂-O-CH(OOH)-CH₃) is a colorless liquid of low viscosity with a pleasant smell. Upon heating it weakly deflagrates, resulting in a fog of acetic acid and water. Diethyl ether hydroperoxide decomposes in the presence of sodium hydroxide and Fe²⁺-containing salts.

Diethyl ether peroxide

Diethyl ether peroxide, also known as ethylidene peroxide, (-CH(CH₃)OO-)_n is a polymerization product of diethyl ether hydroperoxide. It is a colorless oily liquid that is an extremely brisant and friction sensitive explosive material. Amounts of less than 5 milligrams can damage chemical apparatuses.^[who?] The dangerous properties of ether peroxides are the reason that diethyl ether and other peroxide forming ethers like tetrahydrofuran (THF) or ethylene glycol dimethyl ether (1,2-dimethoxyethane) are avoided in industrial processes.

Tests

Diethyl ether peroxides can be detected with potassium iodide (KI) solution or potassium iodide / starch paper. A positive test results in the formation of iodine (I₂) that causes a pink color of the ether phase or a dark bluish spot on the paper strip.

Degradation

Ether peroxides can be destroyed by disproportionation to acetaldehyde with Fe²⁺ or Mn²⁺ ions or with triphenylphosphine (PPh₃). The resulting aldehyde has to be removed to prevent a rapid back-formation of peroxides.

References

A. Rieche, R. Meister, Modellversuche zur Autoxidation der Äther, Angewandte Chemie 49(5):106 (1936) (German)

Categories:
Organic peroxides

Diethyl ether hydroperoxide

Identifiers
CAS number	18321-53-4
ChemSpider	19985446^Y
Jmol-3D images	Image 1 Image 2
SMILES CCOC(OO)C CC(OCC)OO
InChI InChI=1S/C4H10O3/c1-3-6-4(2)7-5/h4-5H,3H2,1-2H3^Y Key: CXWWPQGYBJCHJL-UHFFFAOYSA-N^Y InChI=1/C4H10O3/c1-3-6-4(2)7-5/h4-5H,3H2,1-2H3 Key: CXWWPQGYBJCHJL-UHFFFAOYAS
Properties
Molecular formula	C₄H₁₀O₃
Molar mass	106.12 g/mol
Density	1.005 g/cm³
Boiling point	62 - 64 °C at 18.7 hPa (reduced pressure)
Hazards
Main hazards	Explosive
NFPA 704	4 2 4
Y ether peroxide (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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Academic Dictionaries and Encyclopedias

Diethyl ether peroxide

Contents

Diethyl ether hydroperoxide

Diethyl ether peroxide

Tests

Degradation

References

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Wikipedia

Diethyl ether peroxide

Contents

Diethyl ether hydroperoxide

Diethyl ether peroxide

Tests

Degradation

References

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