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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.⁴ The company filed another patent on a method of synthesizing the same compound, albeit called s-dimethylethyleneurea, in 1944.⁵

Soon thereafter William Boon from the Imperial Chemical Industries published a different synthesis method of what he called 1:3-dimethyliminazolid-2-one.⁶ The compound was more closely studied in the 1960s,⁷⁸⁹ with its adoption as a solvent starting in the 1970s.¹⁰

Solvent

DMI has excellent solvating ability for both inorganic and organic compounds. In many applications, 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).¹²

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

DMI is toxic in contact with skin.¹³ [dubious – discuss]

References

1. Leahy, Ellen M. "1,3-Dimethyl-2-imidazolidinone" e-EROS Encyclopedia of Reagents for Organic Synthesis (2001),doi:10.1002/047084289X.rd342 /wiki/Doi_(identifier) ↩

2. 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. https://pubs.acs.org/doi/10.1021/je60069a034 ↩

3. 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. https://www.academia.edu/114612084/Ureas_as_Solvents_for_Chemical_Investigations ↩

4. U.S. patent 2,405,693 https://patents.google.com/patent/US2405693 ↩

5. U.S. patent 2,422,400 https://patents.google.com/patent/US2422400 ↩

6. 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. https://pubs.rsc.org/en/content/articlelanding/1947/jr/jr9470000307 ↩

7. 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. https://pubs.acs.org/doi/pdf/10.1021/ja01465a025 ↩

8. Lien, Eric J. (1966). Dipole Moment, Structure and Activity of Cyclic Ureas, Thioureas and Related Compounds. University of California, San Francisco. https://books.google.com/books?id=UTdolpPC8o8C&q=dimethylethyleneurea ↩

9. 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 2025-01-18 978-1-4684-8947-7 ↩

10. 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. https://www.academia.edu/114612084/Ureas_as_Solvents_for_Chemical_Investigations ↩

11. 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. /wiki/Doi_(identifier) ↩

12. 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. https://www.academia.edu/114612084/Ureas_as_Solvents_for_Chemical_Investigations ↩

13. DMI at TCI https://www.tcichemicals.com/eshop/en/us/commodity/D1477/ ↩