Efficient synthesis of bio-monomer 2,5-furandicarboxylic acid from concentrated 5-hydroxymethylfurfural or fructose in DMSO/H2O mixed solvent

Huai Liu; Xuejuan Cao; Ting Wang; Junnan Wei; Xing Tang; Xianhai Zeng; Yong Sun; Tingzhou Lei; Shijie Liu; Lu Lin

Journal of Industrial and Engineering Chemistry, Vol.77, 209-214, September, 2019

DOI10.1016/j.jiec.2019.04.038 Export Citation

Efficient synthesis of bio-monomer 2,5-furandicarboxylic acid from concentrated 5-hydroxymethylfurfural or fructose in DMSO/H2O mixed solvent

Huai Liu¹, Xuejuan Cao¹, Ting Wang¹, Junnan Wei¹, Xing Tang^{1, 2, †}, Xianhai Zeng^{1, 2}, Yong Sun^{1, 2}, Tingzhou Lei³, Shijie Liu⁴, and Lu Lin^{1, 2, †}

¹Xiamen Key Laboratory of Clean and High-valued Applications of Biomass, College of Energy, Xiamen University, Xiang’an South Road, Xiamen 361102, China
²Fujian Engineering and Research Center of Clean and High-valued Technologies for Biomass, Xiamen University, Xiang’an South Road, Xiamen 361005, Fujian, China
³Henan Key Lab of Biomass Energy, Huayuan Road 29, Zhengzhou 450008, Henan, China
⁴302 Walters Hall, 1 Forestry Drive, Syracuse, NY 13210, United States, USA

E-mail:,

The conversion of concentrated 5-hydroxymethylfurfural (HMF) or fructose to 2,5-furandicarboxylic acid (FDCA), a renewable alternative to petroleum-derived terephthalate acid, is highly desirable but challenging for FDCA production in an industrial scale. In this contribution, DMSO/H2O mixture was demonstrated as an effective medium for the production of FDCA from high concentration of HMF or fructose. For example, FDCA yield up to 93% was achieved at 10 wt% HMF concentration in DMSO/H2O over commercially available Ru/C (2 equiv. NaHCO3, 130 °C, 4 MPa O2 and 12 h). Furthermore, an overall FDCA yield of 65% was achieved from concentrated fructose (19 wt%) through a facile two-step process. Notably, it is so far the highest HMF or fructose concentration employed for FDCA formation. As compared to pure water or DMSO, DMSO/H2O mixed system is able to stabilize HMF in an alkaline environment, which allows the efficient oxidation of HMF at high concentrations.

Keywords:5-hydroxymethylfurfural;2,5-furandicarboxylic acid;DMSO/H2O;Oxidation;Fructose

[References]

Wang F, Yuan Z, Liu B, Chen S, Zhang Z, J. Ind. Eng. Chem., 38, 181 (2016)
Mishra DK, Cho JK, Yi YJ, Lee HJ, Kim YJ, J. Ind. Eng. Chem., 70, 338 (2019)
Sarmah B, Srivastava R, Manjunathan P, Shanbhag GV, ACS Sustainable Chem. Eng., 3, 2933 (2015)
Liu B, Zhang Z, ChemSusChem, 9, 2015 (2016)
Zuo M, Le K, Feng Y, Xiong C, Li Z, Zeng X, Tang X, Sun Y, Lin L, Ind. Crop. Prod., 112, 18 (2018)
Sajid M, Zhao X, Liu D, Green Chem., 20, 5427 (2018)
Pal P, Saravanamurugan S, ChemSusChem, 12, 145 (2019)
Gao Z, Xie R, Fan G, Yang L, Li F, ACS Sustainable Chem. Eng., 5, 5852 (2017)
Mishra DK, Cho JK, Kim YJ, J. Ind. Eng. Chem., 60, 513 (2018)
Kang ES, Chae DW, Kim B, Kim YG, J. Ind. Eng. Chem., 18(1), 174 (2012)
Kucherov FA, Gordeev EG, Kashin AS, Ananikov VP, Angew. Chem.-Int. Edit., 56, 15931 (2017)
Zhang Z, Huber GW, Chem. Soc. Rev., 47, 1351 (2018)
Chen C, Li X, Wang L, Liang T, Wang L, Zhang Y, Zhang J, ACS Sustainable Chem. Eng., 5, 11300 (2017)
Liu XX, Xiao JF, Ding H, Zhong WZ, Xu Q, Su SP, Yin DL, Chem. Eng. J., 283, 1315 (2016)
Ren Y, Liu B, Zhang Z, Lin J, J. Ind. Eng. Chem., 21, 1127 (2015)
Papageorgiou GZ, Papageorgiou DG, Terzopoulou Z, Bikiaris DN, Eur. Polym. J., 83, 202 (2016)
Motagamwala AH, Won W, Sener C, Alonso DM, Maravelias CT, Dumesic JA, Sci. Adv., 4, eaap97 (2018)
Liu B, Ren Y, Zhang Z, Green Chem., 17, 1610 (2015)
Zhang LX, Xi GY, Chen Z, Qi ZY, Wang XC, Chem. Eng. J., 307, 877 (2017)
Ventura M, Lobefaro F, de Giglio E, Distaso M, Nocito F, Dibenedetto A, ChemSusChem, 11, 1305 (2018)
Buonerba A, Impemba S, Litta AD, Capacchione C, Milione S, Grassi A, ChemSusChem, 11, 3139 (2018)
Rao KTV, Rogers JL, Souzanchi S, Dessbesell L, Ray MB, Xu C, ChemSusChem, 11, 3323 (2018)
Xie J, Nie J, Liu H, Chin. J. Catal., 35, 937 (2014)
Yi G, Teong SP, Zhang Y, Green Chem., 18, 979 (2016)
Kim M, Su Y, Fukuoka A, Hensen E, Nakajima K, Angew. Chem.-Int. Edit., 130, 8367 (2018)
Han X, Li C, Liu X, Xia Q, Wang Y, Green Chem., 19, 996 (2017)
Davis SE, Ide MS, Davis RJ, Green Chem., 15, 17 (2013)
Shuai L, Luterbacher J, ChemSusChem, 9, 133 (2016)
Ghezali W, Vigier KDO, Kessas R, Jerome R, Green Chem., 17, 4459 (2015)
Yang L, Tsilomelekis G, Caratzoulas S, Vlachos DG, ChemSusChem, 8, 1289 (2015)
Mukherjee A, Dumont MJ, Raghavan V, Biomass Bioenergy, 72, 143 (2015)
Zhou X, Jin WB, Sun CF, Gao SH, Chen C, Wang Q, Han SF, Tu RJ, Latif MA, Wang QL, Chem. Eng. J., 343, 324 (2018)
Wong CYY, Choi AWT, Lui MY, Fridrich B, Horvath AK, Mika LT, Horvath IT, Struct. Chem., 28, 423 (2017)
Gao TY, Chen J, Fang WH, Cao QE, Su WP, Dumeignil F, J. Catal., 368, 53 (2018)
Tsilomelekis G, Josephson TR, Nikolakis V, Caratzoulas S, ChemSusChem, 7, 117 (2014)
Han X, Li C, Liu X, Xia Q, Wang Y, Green Chem., 19, 996 (2017)
Pichler CM, Al-Shaal MG, Gu D, Joshi H, Ciptonugroho W, Schuth F, ChemSusChem, 11, 2083 (2018)

[Referenced By]

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

[2] Mishra DK, Cho JK, Yi YJ, Lee HJ, Kim YJ, J. Ind. Eng. Chem., 70, 338 (2019)

[3] Sarmah B, Srivastava R, Manjunathan P, Shanbhag GV, ACS Sustainable Chem. Eng., 3, 2933 (2015)

[4] Liu B, Zhang Z, ChemSusChem, 9, 2015 (2016)

[5] Zuo M, Le K, Feng Y, Xiong C, Li Z, Zeng X, Tang X, Sun Y, Lin L, Ind. Crop. Prod., 112, 18 (2018)

[6] Sajid M, Zhao X, Liu D, Green Chem., 20, 5427 (2018)

[7] Pal P, Saravanamurugan S, ChemSusChem, 12, 145 (2019)

[8] Gao Z, Xie R, Fan G, Yang L, Li F, ACS Sustainable Chem. Eng., 5, 5852 (2017)

[9] Mishra DK, Cho JK, Kim YJ, J. Ind. Eng. Chem., 60, 513 (2018)

[10] Kang ES, Chae DW, Kim B, Kim YG, J. Ind. Eng. Chem., 18(1), 174 (2012)

[11] Kucherov FA, Gordeev EG, Kashin AS, Ananikov VP, Angew. Chem.-Int. Edit., 56, 15931 (2017)

[12] Zhang Z, Huber GW, Chem. Soc. Rev., 47, 1351 (2018)

[13] Chen C, Li X, Wang L, Liang T, Wang L, Zhang Y, Zhang J, ACS Sustainable Chem. Eng., 5, 11300 (2017)

[14] Liu XX, Xiao JF, Ding H, Zhong WZ, Xu Q, Su SP, Yin DL, Chem. Eng. J., 283, 1315 (2016)

[15] Ren Y, Liu B, Zhang Z, Lin J, J. Ind. Eng. Chem., 21, 1127 (2015)

[16] Papageorgiou GZ, Papageorgiou DG, Terzopoulou Z, Bikiaris DN, Eur. Polym. J., 83, 202 (2016)

[17] Motagamwala AH, Won W, Sener C, Alonso DM, Maravelias CT, Dumesic JA, Sci. Adv., 4, eaap97 (2018)

[18] Liu B, Ren Y, Zhang Z, Green Chem., 17, 1610 (2015)

[19] Zhang LX, Xi GY, Chen Z, Qi ZY, Wang XC, Chem. Eng. J., 307, 877 (2017)

[20] Ventura M, Lobefaro F, de Giglio E, Distaso M, Nocito F, Dibenedetto A, ChemSusChem, 11, 1305 (2018)

[21] Buonerba A, Impemba S, Litta AD, Capacchione C, Milione S, Grassi A, ChemSusChem, 11, 3139 (2018)

[22] Rao KTV, Rogers JL, Souzanchi S, Dessbesell L, Ray MB, Xu C, ChemSusChem, 11, 3323 (2018)

[23] Xie J, Nie J, Liu H, Chin. J. Catal., 35, 937 (2014)

[24] Yi G, Teong SP, Zhang Y, Green Chem., 18, 979 (2016)

[25] Kim M, Su Y, Fukuoka A, Hensen E, Nakajima K, Angew. Chem.-Int. Edit., 130, 8367 (2018)

[26] Han X, Li C, Liu X, Xia Q, Wang Y, Green Chem., 19, 996 (2017)

[27] Davis SE, Ide MS, Davis RJ, Green Chem., 15, 17 (2013)

[28] Shuai L, Luterbacher J, ChemSusChem, 9, 133 (2016)

[29] Ghezali W, Vigier KDO, Kessas R, Jerome R, Green Chem., 17, 4459 (2015)

[30] Yang L, Tsilomelekis G, Caratzoulas S, Vlachos DG, ChemSusChem, 8, 1289 (2015)

[31] Mukherjee A, Dumont MJ, Raghavan V, Biomass Bioenergy, 72, 143 (2015)

[32] Zhou X, Jin WB, Sun CF, Gao SH, Chen C, Wang Q, Han SF, Tu RJ, Latif MA, Wang QL, Chem. Eng. J., 343, 324 (2018)

[33] Wong CYY, Choi AWT, Lui MY, Fridrich B, Horvath AK, Mika LT, Horvath IT, Struct. Chem., 28, 423 (2017)

[34] Gao TY, Chen J, Fang WH, Cao QE, Su WP, Dumeignil F, J. Catal., 368, 53 (2018)

[35] Tsilomelekis G, Josephson TR, Nikolakis V, Caratzoulas S, ChemSusChem, 7, 117 (2014)

[36] Han X, Li C, Liu X, Xia Q, Wang Y, Green Chem., 19, 996 (2017)

[37] Pichler CM, Al-Shaal MG, Gu D, Joshi H, Ciptonugroho W, Schuth F, ChemSusChem, 11, 2083 (2018)