Syntheses and characterizations of allyl cellulose and glycidyl cellulose

Allyl cellulose was synthesized by reacting cellulose with allyl bromide in homogeneous LiCl/DMAc solution containing NaOH powder. The degree of substitution (DS) per anhydroglucose (AHG) unit was determined by titrating the allyl cellulose with bromine in chloroform solution, and an allyl DS of 2.80 was found. Glycidyl cellulose was then prepared by reacting this allyl cellulose with peracetic acid in methylene chloride at ambient temperature for 6 days. The measured reaction rate constant was 1.33 × 10−3 min−1. The glycidyl cellulose thus obtained with a glycidyl DS of 2.58 was determined by titrating the product with perchloric acid in conjunction with tetrabutylammonium iodide. The 2.58 of glycidyl DS was also confirmed by 1H‐NMR integration. Both allyl cellulose and glycidyl cellulose were analyzed and characterized with FTIR, 1H‐NMR, 13C‐NMR, TGA, and GPC. During epoxidation of allyl cellulose, possible side reaction leading to ester formation was evidenced from the continuous increase of vCO at 1735 cm−1 in FTIR analyses. In addition, a bimodal distribution and a decreased molecular weight for glycidyl cellulose were found from GPC data, which might suggest a possible chain scission at the cellulosic ether linkage.