Efficient One-Pot Synthesis of 5-Chloromethylfurfural (CMF) from Carbohydrates in Mild Biphasic Systems

Molecules

Wenhua Gao¹  Yiqun Li²  Zhouyang Xiang¹  Kefu Chen³  Rendang Yang³ 

[1] Departments of Chemistry and Forest Biomaterials, North Carolina State University, Raleigh, NC 27695-8005, USA;Department of Chemistry, Jinan University, Guangzhou 510632, China;State Key Laboratory Pulp and Paper Engineering, South China University of Technology, Guangzhou 510460, China

关键词: 5-chloromethylfurfural;    carbohydrates;    biphasic system;   

DOI  :  10.3390/molecules18077675

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2013 by the authors; licensee MDPI, Basel, Switzerland.