CARBOHYDRATE-UREA-PHENOL-BASED ADHESIVES: TRANSIENT FORMATION OF MONO- AND DI-D-GLUCOSYLUREA

Article abstract of DOI:10.1016/0008-6215(89)84089-3

The chemistry of the acid stage of the synthesis of carbohydrate-based adhesives has been investigated.The sulfuric acid-catalyzed reactions of D-glucose with urea in a phenol-water solution provided both N-β-D-glucopyranosylurea and N,N'-di-β-D-glucopyranosylurea.These compounds have been isolated from the resin as perbenzoylated derivatives, and compared spectroscopically with authentic samples.The D-glucosylureas are transient products whose combined yields approach 35percent of the carbohydrate fraction during the initial stages of resin synthesis.Only traces of 5-(hydroxymethyl)-2-furaldehyde, levulinic acid, and formic acid were detected in the resin mixture, suggesting that the classical dehydration pathway is not a major route for the disappearance of D-glucose.