Efficient conversion of N-acetyl-D-glucosamine into nitrogen-containing compound 3-acetamido-5-acetylfuran using amino acid ionic liquid as the recyclable catalyst

Jiao Wang; Hongjun Zang; Shuolei Jiao; Kang Wang; Zhen Shang; Huanxin Li; Jing Lou

doi:10.1016/j.scitotenv.2019.136293

Efficient conversion of N-acetyl-_D-glucosamine into nitrogen-containing compound 3-acetamido-5-acetylfuran using amino acid ionic liquid as the recyclable catalyst

Sci Total Environ. 2020 Mar 25:710:136293. doi: 10.1016/j.scitotenv.2019.136293. Epub 2019 Dec 26.

Authors

Jiao Wang¹, Hongjun Zang², Shuolei Jiao¹, Kang Wang¹, Zhen Shang¹, Huanxin Li¹, Jing Lou¹

Affiliations

¹ State Key Laboratory of Hollow Fiber Membrane Materials and Processes, School of Chemistry and Chemical Engineering, Tiangong University, Binshuixi Road, Tianjin 300387, China.
² State Key Laboratory of Hollow Fiber Membrane Materials and Processes, School of Chemistry and Chemical Engineering, Tiangong University, Binshuixi Road, Tianjin 300387, China. Electronic address: zanghongjun@tjpu.edu.cn.

PMID: 31926412
DOI: 10.1016/j.scitotenv.2019.136293

Abstract

Chitin is the most widely distributed oceanic biomass resources. Its monomer unit, N-acetyl-_D-glucosamine (NAG), contains precious atomic nitrogen and represents a potential feedstock for the manufacture of regenerative organic nitrogen chemicals. Herein, the conversion of NAG to the platform chemical, 3-acetamido-5-acetylfuran (3A5AF), catalyzed by amino acid ionic liquids, was investigated. The reaction, catalyzed by a very small amount of glycine chloride ionic liquid without any additives, could yield 43.22% 3A5AF in 10 min. By adding CaCl₂, a higher yield up to 52.61% was obtained. This work demonstrated the conversion of chitin biomass to 3A5AF in higher yield without using a boron-based catalyst for the first time. Moreover, the ionic liquid catalyst exhibited excellent recyclability, and afforded 43.22-36.59% yield over during eight cycles. This research provides new and green procedures to convert shellfish fishery waste into value-added platform chemicals.

Keywords: 3-Acetamido-5-acetylfuran; Amino acid ionic liquid; Conversion; Green process; N-acetyl-(D)-glucosamine.