Cellulose recycling as a source of raw chirality

CORNE, V.; BOTTA, M. C.; GIORDANO, E.D.; GIRI, G. F.; LLOMPART, D.F.; BIAVA, H.D.; SAROTTI, A.M.; MATA, E.G.; SUÁREZ, A.G.; SPANEVELLO, R.A.

Foz de Iguazú

Conferencia; 4th International IUPAC Conference on Green Chemistry; 2012

IUPAC

Cellulose is the most widely spread biopolymer on Earth. Nowadays, paper manufacturing is its major industrial demand. The annual paper production in weight is equivalent to three times the car industry production measured in the same way. Due to this production volume, it is easy to foresee the great amount of waste paper that is accumulated as result of human activity. Paper can be recycled, but only for a limited number of turns over, and for this reason it is important to find other uses to any cellulosic material. On the other hand, cellulose is a polymer based on cellobiose as monomer and this disaccharide is formed by two enantiomerically pure units of glucose which in terms could be a great source of chirality if appropriately treated. Starting from cellulose microcrystalline, waste paper or cellulose mud (a waste from paper industry), we have optimized the conventional pyrolysis conditions and developed new microwave-assisted pyrolysis1 to degrade the cellulose polymeric chain into a useful building block named levoglucosenone (1). This compound has been used as chiral synthon in the synthesis of a wide variety of products. For this reason, we have been concerned with the synthetic application of 1 as a versatile starting material in the development of new tools for asymmetric synthesis.