Innovative transformation of cellulosic materials into useful chemicals

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

Otro; ACS Summer School on Green Chemistry and Sustainable Energy 2012; 2012

American Chemical Society

Biomass is a widely available raw material which has been recognized as an important source of fuels and chemical products. By far, carbohydrates are the major annually renewable biofeedstocks from which to develop viable organic chemicals that can compete or eventually replace those derived from fossil sources. Cellulose, is the most common organic compound on earth. For this reason, the generation of useful chemicals from cellulose or cellulosic waste materials is of great interest. Levoglucosenone (1) is a versatile and readily available member of the carbohydrate derived chiral pool, which has been used as chiral synthon in the synthesis of a wide variety of compounds.1 As part of our program on the pyrolytic conversion of cellulose waste into high value chemicals, we have been concerned with the synthetic application of levoglucosenone as a chiral building block in the development of new asymmetric inductors.2 Conventional pyrolysis of cellulose or cellulose-containing materials such as waste paper is typically used to generate 1,2 but microwave irradiation of microcrystalline cellulose was recently found to be also effective.31- a) Levoglucosenone and Levoglucosans: Chemistry and Applications;Witczak, Z. J., Ed.; ATL: Mount Prospect, IL, 1994. b) Sarotti, A. M.; Zanardi, M.M.; Spanevello, R. A; Suárez, A. G. Current Organic ynthesis. 2012. In press.2- a) Sarotti, A. M.; Spanevello, R. A; Suárez, A. G. Tetrahedron, 2009, 65, 3502.b) Sarotti, A. M.; Spanevello, R. A.; Duhayon, C.; Tuchagues, J. P.; Suárez, A.G. Tetrahedron, 2007, 63, 241. c) Zanardi, M. M.; Suárez, A. G. TetrahedronLetters, 2009, 50, 999.3- Sarotti, A. M.; Spanevello, R. A.; Suárez, A. G. Green Chem. 2007, 9, 1137.