Preparation of 3-aceta mido-5-acetylfuran from N-acetylglucosamine and chitin using biobased deep eutectic solvents as catalysts

Chaoqiang Wu; Chengyong Wang; Alei Zhang; Kequan Chen; Fei Cao; Pingkai Ouyang

doi:10.1039/d2re00118g

Preparation of 3-aceta mido-5-acetylfuran from N-acetylglucosamine and chitin using biobased deep eutectic solvents as catalysts

Chaoqiang Wu, Chengyong Wang, Alei Zhang, Kequan Chen, Fei Cao, Pingkai Ouyang

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

Research output: Contribution to journal › Article › peer-review

20 Scopus citations

Abstract

3-Acetamido-5-acetylfuran (3A5AF) is an important platform compound, possessing very promising application prospects. Herein, we propose a new approach to convert N-acetylglucosamine (NAG) and chitin to 3A5AF using biobased deep eutectic solvents (DESs) containing choline chloride and various organic acids or polyols. A comparison of catalytic capacity showed that a DES made with choline chloride/citric acid (CCCA) possesses the optimum catalytic properties, which lead to a maximum yield for 3A5AF of 47.1 mol% and 5.0 mol% from NAG and chitin, respectively, at 210 °C in N,N-dimethylacetamide solvent with CaCl₂·2H₂O as an additive. Moreover, CCCA showed excellent recyclability and retained over 63.6% of its original activity after five cycles of use. In addition, the 3A5AF product was obtained with 99.0% purity by simple extraction and crystallization. This research provided a new avenue for 3A5AF production from renewable chitin resources.

Original language	English
Pages (from-to)	1742-1749
Number of pages	8
Journal	Reaction Chemistry and Engineering
Volume	7
Issue number	8
DOIs	https://doi.org/10.1039/d2re00118g
State	Published - 23 Apr 2022

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title = "Preparation of 3-aceta mido-5-acetylfuran from N-acetylglucosamine and chitin using biobased deep eutectic solvents as catalysts",

abstract = "3-Acetamido-5-acetylfuran (3A5AF) is an important platform compound, possessing very promising application prospects. Herein, we propose a new approach to convert N-acetylglucosamine (NAG) and chitin to 3A5AF using biobased deep eutectic solvents (DESs) containing choline chloride and various organic acids or polyols. A comparison of catalytic capacity showed that a DES made with choline chloride/citric acid (CCCA) possesses the optimum catalytic properties, which lead to a maximum yield for 3A5AF of 47.1 mol% and 5.0 mol% from NAG and chitin, respectively, at 210 °C in N,N-dimethylacetamide solvent with CaCl2·2H2O as an additive. Moreover, CCCA showed excellent recyclability and retained over 63.6% of its original activity after five cycles of use. In addition, the 3A5AF product was obtained with 99.0% purity by simple extraction and crystallization. This research provided a new avenue for 3A5AF production from renewable chitin resources.",

author = "Chaoqiang Wu and Chengyong Wang and Alei Zhang and Kequan Chen and Fei Cao and Pingkai Ouyang",

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T1 - Preparation of 3-aceta mido-5-acetylfuran from N-acetylglucosamine and chitin using biobased deep eutectic solvents as catalysts

AU - Wu, Chaoqiang

AU - Wang, Chengyong

AU - Zhang, Alei

AU - Chen, Kequan

AU - Cao, Fei

AU - Ouyang, Pingkai

PY - 2022/4/23

Y1 - 2022/4/23

N2 - 3-Acetamido-5-acetylfuran (3A5AF) is an important platform compound, possessing very promising application prospects. Herein, we propose a new approach to convert N-acetylglucosamine (NAG) and chitin to 3A5AF using biobased deep eutectic solvents (DESs) containing choline chloride and various organic acids or polyols. A comparison of catalytic capacity showed that a DES made with choline chloride/citric acid (CCCA) possesses the optimum catalytic properties, which lead to a maximum yield for 3A5AF of 47.1 mol% and 5.0 mol% from NAG and chitin, respectively, at 210 °C in N,N-dimethylacetamide solvent with CaCl2·2H2O as an additive. Moreover, CCCA showed excellent recyclability and retained over 63.6% of its original activity after five cycles of use. In addition, the 3A5AF product was obtained with 99.0% purity by simple extraction and crystallization. This research provided a new avenue for 3A5AF production from renewable chitin resources.

AB - 3-Acetamido-5-acetylfuran (3A5AF) is an important platform compound, possessing very promising application prospects. Herein, we propose a new approach to convert N-acetylglucosamine (NAG) and chitin to 3A5AF using biobased deep eutectic solvents (DESs) containing choline chloride and various organic acids or polyols. A comparison of catalytic capacity showed that a DES made with choline chloride/citric acid (CCCA) possesses the optimum catalytic properties, which lead to a maximum yield for 3A5AF of 47.1 mol% and 5.0 mol% from NAG and chitin, respectively, at 210 °C in N,N-dimethylacetamide solvent with CaCl2·2H2O as an additive. Moreover, CCCA showed excellent recyclability and retained over 63.6% of its original activity after five cycles of use. In addition, the 3A5AF product was obtained with 99.0% purity by simple extraction and crystallization. This research provided a new avenue for 3A5AF production from renewable chitin resources.

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JO - Reaction Chemistry and Engineering

JF - Reaction Chemistry and Engineering

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ER -

Preparation of 3-aceta mido-5-acetylfuran from N-acetylglucosamine and chitin using biobased deep eutectic solvents as catalysts

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