ARS | Publication request: Preparation and characterization of aminobenzyl cellulose by two step synthesis from native cellulose

Submitted to: Fibers and Polymers
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: September 1, 2010
Publication Date: December 1, 2010
Citation: Chang, S., Condon, B.D., Edwards, J.V. 2010. Preparation and characterization of aminobenzyl cellulose by two step synthesis from native cellulose. Fibers and Polymers. 11(8):1101-1105.

Interpretive Summary: In our project to develop new uses from value added products and processes from native cellulosic materials, we designed and develop chemically modified celluloses that are water repellent and flame retardant properties reactive with functional group of atoms (nitrogen, carbon oxygen ) such as epoxides and isocyantes (-N=C=O). Chemically modified celluloses have been made in two steps via homogeneous necleophilic displacement reaction and heterogeneous reduction by indium metal. All of the characteristic information obtained about the nature of the reaction products of cellulose and possible flame retardant properties of modified celluloses. Carbon 13 solid state nuclear magnetic resonance spectroscopy was used to detect change in intensity patterns of the native and modified celluloses due to the presence of a carbon 13 enriched on cellulose derivatives. Furthermore, different stretching frequencies between nitro and amino group in cellulose derivatives detected by infrared spectroscopy, fourier transform infrared (FTIR) spectroscopy. This success of work will benefit scientists involved in generation new uses for cellulosic product as well as manufacturers of woven and nonwoven cotton product in new worldwide market.

Technical Abstract: Synthesis and structural characterizations of nitro- and amino-benzyl cellulose were carried out. Cellulose derivatives were synthesized by etherification. Nitrobenzylation produced 80% yield by treating a mixture of microcrystalline cellulose, 4-dimethyl aminopyridine and 4-nitrobenzyl chloride at 80 ºC for 10 h. Nitro-benzyl cellulose was then reduced to amino-benzyl cellulose with 93% yield using indium metal in ethanol and saturated aqueous ammonium chloride. In addition to their structural characterizations by FT-IR and 13C CP/MAS NMR, TGA will also be described. These reactions serve as models for future cotton fiber finishing technology with applications in water repellency and flame resistance.