Production of levulinic acid from glucosamine using zirconium oxychloride

Mi-Ra Park; Sung-Koo Kim; Gwi-Taek Jeong

Journal of Industrial and Engineering Chemistry, Vol.61, 119-123, May, 2018

DOI10.1016/j.jiec.2017.12.008 Export Citation

Production of levulinic acid from glucosamine using zirconium oxychloride

Mi-Ra Park, Sung-Koo Kim, and Gwi-Taek Jeong^†

Department of Biotechnology, Pukyong National University, Busan 48513, Republic of Korea

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In this study, we evaluated zirconium oxychloride (ZrOCl2), an eco-friendly Lewis acid as a catalyst for conversion of glucosamine (a monomer of chitosan obtained from shell-crustacean food waste) into levulinic acid (LA). In a ZrOCl2-catalyzed hydrothermal reaction, 21.29 mol% of LA was obtained using optimized conditions with 50 g/L glucosamine and 15 mol% ZrOCl2, at 200 °C for 20 min. Our results demonstrate the potential of glucosamine as a recyclable feedstock and ZrOCl2 as an eco-friendly catalyst for platform chemical synthesis.

Keywords:Glucosamine;Zirconium oxychloride;Platform chemicals;5-Hydroxymethylfurfural;Levulinic acid

[References]

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Wang F, Yuan Z, Liu B, Chen S, Zhang Z, J. Ind. Eng. Chem., 38, 181 (2016)
Lee SB, Jeong GT, Appl. Biochem. Biotechnol., 176(4), 1151 (2015)
Omari KW, Besaw JE, Kerton FM, Green Chem., 14, 1480 (2012)
Wang YX, Pedersen CM, Deng TS, Qiao Y, Hou XL, Bioresour. Technol., 143, 384 (2013)
Jeong GT, Ind. Crop. Prod., 62, 77 (2014)
Yu S, Zang H, Chen S, Jiang Y, Yan B, Cheng B, Polym. Degrad. Stabil., 134, 105 (2016)
Zang H, Yu S, Yu P, Ding H, Du Y, Yang Y, Zhang Y, Carbohydr. Res., 442, 1 (2017)
Kim DH, Lee SB, Kim SK, Park DH, Jeong GT, Bioenerg. Res., 9, 1155 (2016)
Jeong GT, Ra CH, Hong YK, Kim JK, Kong IS, Kim SK, Park DH, Bioprocess. Biosyst. Eng., 38, 207 (2015)
Szabolcs A, Molnar M, Dibo G, Mika LT, Green Chem., 15, 439 (2013)
Choi C, Nam JP, Nah JW, J. Ind. Eng. Chem., 33, 1 (2016)
Kim SK, Chitin, Chitosan, Oligosaccharides and Their Derivatives: Biological Activities and Applications, CRC, Press, New York, 2011.
Saha B, De S, Fan MH, Fuel, 111, 598 (2013)
Dutta S, De S, Alam MI, Abu-Omar MM, Saha B, J. Catal., 288, 8 (2012)
Cai CM, Nagane N, Kumar R, Wyman CE, Green Chem., 16, 3819 (2014)
Xu ZL, Wang XY, Shen MY, Du CH, Chem. Pap., 70(12), 1649 (2016)
Nikoofar K, Khademi Z, Res. Chem. Intermed., 42(5), 3929 (2016)
Lewis RJSR, 8th ed., Dangerous Properties of Industrial Materials, vol. 3, Van Nostrand Reinhold, New York, 1989.
Pedersen M, Meyer AS, New Biotechnol., 27(6), 739 (2010)
Kuster BFM, Starch, 42(8), 314 (1990)
Yu S, Brown HM, Huang XW, Zhou XD, Amonette JE, Zhang ZC, Appl. Catal. A: Gen., 361(1-2), 117 (2009)

[Referenced By]

[1] Hoekman SK, Renew. Energy, 34(1), 14 (2009)

[2] Hayes DJ, Fitzpatrick S, Hayes MHB, Ross JRH, ... Industrial Processes and Products, WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, pp. 139 (2006).

[3] Bozell JJ, Petersen GR, Green Chem., 12(4), 539 (2010)

[4] Kim D, Lee K, Park KY, J. Ind. Eng. Chem., 42, 95 (2016)

[5] Morone A, Apte M, Pandey RA, Renew. Sust. Energ. Rev., 51, 548 (2015)

[6] Mukherjee A, Dumont MJ, Raghauan V, Biomass Bioenerg., 72, 143 (2015)

[7] Wang F, Yuan Z, Liu B, Chen S, Zhang Z, J. Ind. Eng. Chem., 38, 181 (2016)

[8] Lee SB, Jeong GT, Appl. Biochem. Biotechnol., 176(4), 1151 (2015)

[9] Omari KW, Besaw JE, Kerton FM, Green Chem., 14, 1480 (2012)

[10] Wang YX, Pedersen CM, Deng TS, Qiao Y, Hou XL, Bioresour. Technol., 143, 384 (2013)

[11] Jeong GT, Ind. Crop. Prod., 62, 77 (2014)

[12] Yu S, Zang H, Chen S, Jiang Y, Yan B, Cheng B, Polym. Degrad. Stabil., 134, 105 (2016)

[13] Zang H, Yu S, Yu P, Ding H, Du Y, Yang Y, Zhang Y, Carbohydr. Res., 442, 1 (2017)

[14] Kim DH, Lee SB, Kim SK, Park DH, Jeong GT, Bioenerg. Res., 9, 1155 (2016)

[15] Jeong GT, Ra CH, Hong YK, Kim JK, Kong IS, Kim SK, Park DH, Bioprocess. Biosyst. Eng., 38, 207 (2015)

[16] Szabolcs A, Molnar M, Dibo G, Mika LT, Green Chem., 15, 439 (2013)

[17] Choi C, Nam JP, Nah JW, J. Ind. Eng. Chem., 33, 1 (2016)

[18] Kim SK, Chitin, Chitosan, Oligosaccharides and Their Derivatives: Biological Activities and Applications, CRC, Press, New York, 2011.

[19] Saha B, De S, Fan MH, Fuel, 111, 598 (2013)

[20] Dutta S, De S, Alam MI, Abu-Omar MM, Saha B, J. Catal., 288, 8 (2012)

[21] Cai CM, Nagane N, Kumar R, Wyman CE, Green Chem., 16, 3819 (2014)

[22] Xu ZL, Wang XY, Shen MY, Du CH, Chem. Pap., 70(12), 1649 (2016)

[23] Nikoofar K, Khademi Z, Res. Chem. Intermed., 42(5), 3929 (2016)

[24] Lewis RJSR, 8th ed., Dangerous Properties of Industrial Materials, vol. 3, Van Nostrand Reinhold, New York, 1989.

[25] Pedersen M, Meyer AS, New Biotechnol., 27(6), 739 (2010)

[26] Kuster BFM, Starch, 42(8), 314 (1990)

[27] Yu S, Brown HM, Huang XW, Zhou XD, Amonette JE, Zhang ZC, Appl. Catal. A: Gen., 361(1-2), 117 (2009)