Cellulose Recycling as Source of Raw Chirality

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

Foz do Iguaçu

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

IUPAC - Sociedade Brasileira de Química

Cellulose is the most widely spread biopolymer on earth. Its main source of production is from wood and it has been used since ancient times. 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 volumen, 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 celobiose 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, paper waste 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.Herein we wish to report that levoglucosenone is an extremely versatile starting material that has been used to develop:CHIRAL AUXILIARIES A family of chiral auxiliaries were synthesized and successfully used to induce chirality in Diels-Alder and 1,3-dipolar cycloadditions.CHIRAL CATALYSTSA new series of amino-alcohols catalysts were synthesized and proved their chirality activity in the addition reaction of Et2Zn to benzaldehydeSOLID-PHASE CHIRAL CATALYSTSAmino-alcohols catalysts were immobilized on Wang resin and used as supported catalysts in the Et2Zn addition to benzaldehyde.ORGANOCATALYSTSLevoglucosenone-derived chiral pyrrolidines showed organocatalytic activity for iminium ion-based asymmetric Diels-Alder reactions.ENANTIOSPECIFIC SYNTHESISLevoglucosenone was used as starting material for the enantiospecific synthesis of triacetyl D-allal, a rare sugar glycal.