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http://dx.doi.org/10.14478/ace.2011.22.3.319

Study on the Synthesis of N,N'-Dicyclohexylcarbodiimide from N,N'-Dicyclohexylurea  

Kim, Jae Young (Department of Polymer Engineering, College of Engineering, Suwon University)
Chung, Dae-Won (Department of Polymer Engineering, College of Engineering, Suwon University)
Publication Information
Applied Chemistry for Engineering / v.22, no.3, 2011 , pp. 319-322 More about this Journal
Abstract
N,N'-Dicyclohexylcarbodiimide (DCC) known as powerful dehydrating reagent in amide or ester synthesis is converted into N,N'-dicyclohexylurea (DCU) during the reaction. In the paper, DCU was recovered from the reaction for the synthesis of the hydrophilic derivative of ${\beta}$-sitosterol, and the purification of the recovered DCU and the dehydration of DCU into DCC were investigated. In the presence of tosyl chloride, (TsCl) and triethylamine (TEA), DCU was converted into DCC, and the optimum molar ratio of [DCU] : [TsCl] : [TEA] was found to be 1.0 : 1.5 : 3.0. Pure DCC was obtained with a 46% yield by the sublimation after the purification process, and characterized by GC/MS, FT-IR and $^{13}C-NMR$.
Keywords
N,N'-dicyclohexylcarbodiimide; N,N'-dicyclohexylurea; tosyl chloride; dehydration;
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