Conversion of N-acetyl-d-glucosamine to nitrogen-containing chemicals in high-temperature water

Mitsumasa Osadaa Shinya Shojia Shin Suenagaa Makoto Ogatab (2019)

aDepartment of Chemistry and Materials, Faculty of Textile Science and Technology, Shinshu University, 3-15-1, Tokida, Ueda, Nagano 386-8567, Japan

bDepartment of Applied Chemistry and Biochemistry, National Institute of Technology, Fukushima College, Nagao 30, Iwaki, Fukushima 970-8034, Japan

Fuel Processing Technology Volume 195, 1 December 2019, 106154Received 31 May 2019, Revised 6 July 2019, Accepted 14 July 2019, Available online 19 July 2019.

Abstract: To demonstrate the conversion of renewable biomass to platform chemicals, we previously reported the noncatalytic conversion of N-acetyl-d-glucosamine (GlcNAc), which is obtained from chitin, to nitrogen-containing chemicals; however, various aspects of this process were not clarified. Herein, we reported updated and expanded results for the synthesis of nitrogen-containing chemicals from GlcNAc in high-temperature water at 180–280 °C and 25 MPa with a reaction time of 5–34 s. The main products were 2-acetamido-2,3-dideoxy-d-erythro-hex-2-enofuranose (Chromogen I) and 3-acetamido-5-(1′,2′-dihydroxyethyl)furan (Chromogen III) with the maximum yields of 37.0% and 34.5%, respectively. Although 3-acetamido-5-acetylfuran was expected to form by the dehydration of Chromogen III, a yield of only <1% was obtained, likely because the dehydration of Chromogen III is difficult in the absence of a catalyst. The evaluation of the effects of acid and base catalysts on the dehydration of GlcNAc revealed that the acid catalyst suppressed the transformation of GlcNAc to Chromogen I and promoted the transformation of Chromogen I to Chromogen III, whereas the base catalyst had the opposite effects on these processes. The synthesis of nitrogen-containing chemicals from GlcNAc in high-temperature water is an environmentally benign method for utilizing renewable chitin biomass.

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