Open AccessThis article is
- freely available
Efficient One-Pot Synthesis of 5-Chloromethylfurfural (CMF) from Carbohydrates in Mild Biphasic Systems
Departments of Chemistry and Forest Biomaterials, North Carolina State University, Raleigh, NC 27695-8005, USA
State Key Laboratory Pulp and Paper Engineering, South China University of Technology, Guangzhou 510460, China
Department of Chemistry, Jinan University, Guangzhou 510632, China
Center of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia
* Author to whom correspondence should be addressed.
Received: 22 May 2013; in revised form: 24 June 2013 / Accepted: 25 June 2013 / Published: 2 July 2013
Abstract: 5-Halomethylfurfurals can be considered as platform chemicals of high reactivity making them useful for the preparation of a variety of important compounds. In this study, a one-pot route for the conversion of carbohydrates into 5-chloromethylfurfural (CMF) in a simple and efficient (HCl-H3PO4/CHCl3) biphasic system has been investigated. Monosaccharides such as D-fructose, D-glucose and sorbose, disaccharides such as sucrose and cellobiose and polysaccharides such as cellulose were successfully converted into CMF in satisfactory yields under mild conditions. Our data shows that when using D-fructose the optimum yield of CMF was about 47%. This understanding allowed us to extent our work to biomaterials, such as wood powder and wood pulps with yields of CMF obtained being comparable to those seen with some of the enumerated mono and disaccharides. Overall, the proposed (HCl-H3PO4/CHCl3) optimized biphasic system provides a simple, mild, and cost-effective means to prepare CMF from renewable resources.
Keywords: 5-chloromethylfurfural; carbohydrates; biphasic system
Citations to this Article
Cite This Article
MDPI and ACS Style
Gao, W.; Li, Y.; Xiang, Z.; Chen, K.; Yang, R.; Argyropoulos, D.S. Efficient One-Pot Synthesis of 5-Chloromethylfurfural (CMF) from Carbohydrates in Mild Biphasic Systems. Molecules 2013, 18, 7675-7685.
Gao W, Li Y, Xiang Z, Chen K, Yang R, Argyropoulos DS. Efficient One-Pot Synthesis of 5-Chloromethylfurfural (CMF) from Carbohydrates in Mild Biphasic Systems. Molecules. 2013; 18(7):7675-7685.
Gao, Wenhua; Li, Yiqun; Xiang, Zhouyang; Chen, Kefu; Yang, Rendang; Argyropoulos, Dimitris S. 2013. "Efficient One-Pot Synthesis of 5-Chloromethylfurfural (CMF) from Carbohydrates in Mild Biphasic Systems." Molecules 18, no. 7: 7675-7685.