Journal
GREEN CHEMISTRY
Volume 4, Issue 5, Pages 439-443Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b205319p
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The reactivity of industrially relevant silylalkylamines towards CO2 and dialkyl/arylcarbonates is discussed. The kinetics of uptake of carbon dioxide at various temperatures shows that at 295 K, silylalkylmonoamines react with carbon dioxide in a 2:1 molar ratio, affording classic intermolecular ammonium carbamates of formula RNHCOO-+NH3R, while at 273 K, dimeric carbammic acids, (RNHCOOH)(2), are formed. Conversely, silylalkyldiamines react at 297 K with carbon dioxide to afford zwitterionic intramolecular six-membered cyclic ammonium carbamates of formula RNH2+CH2CH2NHCOO-, a unique example of CO2 uptake by an amine with a 1:1 molar ratio. Such systems may have a potential application in CO2 separation. The catalytic role of carbon dioxide in the carbamation of the above mentioned amines by reaction with organic carbonates is described.
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