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.
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]
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]
References
- ^ DMI at Mitsui Chemicals
- ^ Leahy, Ellen M. "1,3-Dimethyl-2-imidazolidinone" e-EROS Encyclopedia of Reagents for Organic Synthesis (2001),doi:10.1002/047084289X.rd342
- ^ Rosenfarb, Joseph; Huffman, Hugh L. Jr.; Caruso, Joseph A. (1976). "Dielectric constants, viscosities, and related physical properties of several substituted liquid ureas at various temperatures". Journal of Chemical & Engineering Data. 21 (2): 150–153. doi:10.1021/je60069a034. ISSN 0021-9568.
- ^ a b c Barker, Barbara J.; Rosenfarb, Joseph; Caruso, Joseph A. (1979). "Ureas as Solvents for Chemical Investigations". Angewandte Chemie International Edition in English. 18 (7): 503–507. doi:10.1002/anie.197905031. ISSN 1521-3773.
- ^ U.S. patent 2,405,693
- ^ U.S. patent 2,422,400
- ^ Boon, W. R. (1947). "Respiratory stimulants. Part I. Fully-substituted ureas derived from αω-alkylenediamines". Journal of the Chemical Society (Resumed) (0): 307–318. doi:10.1039/JR9470000307. ISSN 0368-1769.
- ^ Zaugg, Harold E. (1960). "Specific Solvent Effects in the Alkylation of Enolate Anions. IV. Kinetic Order of Solvent Participation". ACS Publications. doi:10.1021/ja01465a025. Retrieved 2025-01-18.
- ^ Lien, Eric J. (1966). Dipole Moment, Structure and Activity of Cyclic Ureas, Thioureas and Related Compounds. University of California, San Francisco.
- ^ Ulrich, Henri (1968), Ulrich, Henri (ed.), "Cyclic Imidoyl Halides", The Chemistry of Imidoyl Halides, New York, NY: Springer US, pp. 193–210, doi:10.1007/978-1-4684-8947-7_8, ISBN 978-1-4684-8947-7, retrieved 2025-01-18
- ^ Lo, C.-C.; Chao, P.-M. (1990). "Replacement of carcinogenic solvent HMPA by DMI in insect sex pheromone synthesis". Journal of Chemical Ecology. 16 (12): 3245–3253. doi:10.1007/BF00982095. PMID 24263426. S2CID 9859086.
- ^ DMI at TCI