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1,3-Dimethyl-2-imidazolidinone

Chemical compound From Wikipedia, the free encyclopedia

1,3-Dimethyl-2-imidazolidinone
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1,3-Dimethyl-2-imidazolidinone (DMI) is a cyclic urea used as a high-boiling polar aprotic solvent.[2] This colourless, highly polar solvent has high thermal and chemical stability. Together with homologous solvent DMPU, since the 1970s it serves as an analog of tetramethylurea.[3][4] It can be prepared from 1,2-dimethylethylenediamine by reaction with phosgene.

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History

In 1940 Du Pont applied for a patent on acetylene storage in many polar organic solvents, one of which was 1,3-dimethyl-2-imid azolidone.[5] The company filed another patent on a method of synthesizing the same compound, albeit called s-dimethylethyleneurea, in 1944.[6]

Soon thereafter William Boon from the Imperial Chemical Industries published a different synthesis method of what he called 1:3-dimethyliminazolid-2-one.[7] The compound was more closely studied in the 1960s,[8][9][10] with its adoption as a solvent starting in the 1970s.[4]

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Solvent

DMI has excellent solvating ability for both inorganic and organic compounds. In many applications,[citation needed] DMI (as well as DMPU) can be used as a substitute or replacement for the carcinogenic solvent HMPA.[11] Compared to the 6-atom ring analog, it has an advantage of lower viscosity (1.9 vs. 2.9 cP at 25°C).[4]

DMI is used in a variety of applications including detergents, dyestuffs, electronic materials and in the manufacture of polymers.[citation needed]

DMI is toxic in contact with skin.[12] [dubious discuss]

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References

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