Glucose-derived solid acids and their stability enhancement for upgrading biodiesel via esterification

doi:10.1016/j.cjche.2018.07.019

Abstract

Abstract: Utilization of biomass-derived materials or chemicals plays a significant role in reducing the dependence of unsustainable resources of petroleum and coal. A series of sulfonated glucose-derived solid acids (SGSAs) were developed in this study through a one-step method. These catalysts were characterized by XRD, FT-IR, SEM, and BET to determine their physiochemical properties, and their acid content was measured by acid-base titration. The catalytic performances of SGSA catalysts were evaluated in two esterification reactions:propionic acid or oleic acid with methanol (a typical reaction to upgrade biodiesel). Conversion of oleic acid and selectivity of methyl oleate can reach as high as 93.3% and 94.7% respectively over SGSA-6, which has the highest—SO₃H density. Moreover, regeneration of spent catalysts by sulfuric acid solution can significantly enhance their stability and reusability.

Key words: Solid acids, Glucose, Esterification, Oleic acid, Biodiesel

摘要： Utilization of biomass-derived materials or chemicals plays a significant role in reducing the dependence of unsustainable resources of petroleum and coal. A series of sulfonated glucose-derived solid acids (SGSAs) were developed in this study through a one-step method. These catalysts were characterized by XRD, FT-IR, SEM, and BET to determine their physiochemical properties, and their acid content was measured by acid-base titration. The catalytic performances of SGSA catalysts were evaluated in two esterification reactions:propionic acid or oleic acid with methanol (a typical reaction to upgrade biodiesel). Conversion of oleic acid and selectivity of methyl oleate can reach as high as 93.3% and 94.7% respectively over SGSA-6, which has the highest—SO₃H density. Moreover, regeneration of spent catalysts by sulfuric acid solution can significantly enhance their stability and reusability.

关键词: Solid acids, Glucose, Esterification, Oleic acid, Biodiesel

Donglei Mao, Xingguang Zhang, Xiongfei Zhang, Mingmin Jia, Jianfeng Yao. Glucose-derived solid acids and their stability enhancement for upgrading biodiesel via esterification[J]. Chinese Journal of Chemical Engineering, 2019, 27(5): 1067-1072.

References

[1] D. Chen, X. Zhang, A.F. Lee, Synthetic strategies to nanostructured photocatalysts for CO₂ reduction to solar fuels and chemicals, J. Mater. Chem. A 3(2015) 14487-14516.
[2] A.M. Beale, F. Gao, I. Lezcano-Gonzalez, C.H.F. Peden, J. Szanyi, Recent advances in automotive catalysis for NO_x emission control by small-pore microporous materials, Chem. Soc. Rev. 44(2015) 7371-7405.
[3] P.N.R. Vennestrom, C.M. Osmundsen, C.H. Christensen, E. Taarning, Beyond petrochemicals:The renewable chemicals industry, Angew. Chem. Int. Ed. 50(2011) 10502-10509.
[4] L.M. Gilbertson, J.B. Zimmerman, D.L. Plata, J.E. Hutchison, P.T. Anastas, Designing nanomaterials to maximize performance and minimize undesirable implications guided by the Principles of Green Chemistry, Chem. Soc. Rev. 44(2015) 5758-5777.
[5] Y. Shi, E. Xing, K. Wu, J. Wang, M. Yang, Y. Wu, Recent progress on upgrading of biooil to hydrocarbons over metal/zeolite bifunctional catalysts, Catal. Sci. Technol. 7(2017) 2385-2415.
[6] B. Liu, Z. Zhang, Catalytic conversion of biomass into chemicals and fuels over magnetic catalysts, ACS Catal. 6(2016) 326-338.
[7] B. Chang, Y. Guo, H. Yin, S. Zhang, B. Yang, Synthesis of sulfonated porous carbon nanospheres solid acid by a facile chemical activation route, J. Solid State Chem. 221(2015) 384-390.
[8] W.Y. Lou, M.H. Zong, Z.Q. Duan, Efficient production of biodiesel from high free fatty acid-containing waste oils using various carbohydrate-derived solid acid catalysts, Bioresour. Technol. 99(2008) 8752-8758.
[9] A.P.S. Chouhan, A.K. Sarma, Modern heterogeneous catalysts for biodiesel production:A comprehensive review, Renew. Sust. Energ. Rev. 15(2011) 4378-4399.
[10] Y. Liu, Y. Fang, X. Lu, Z. Wei, X. Li, Hydrogenation of nitrobenzene to p-aminophenol using Pt/C catalyst and carbon-based solid acid, Chem. Eng. J. 229(2013) 105-110.
[11] X. Zhang, L.J. Durndell, M.A. Isaacs, C.M.A. Parlett, A.F. Lee, K. Wilson, Platinumcatalyzed aqueous-phase hydrogenation of D-glucose to D-sorbitol, ACS Catal. 6(2016) 7409-7417.
[12] X. Zhang, X. Ke, Z. Zheng, H. Liu, H. Zhu, TiO₂ nanofibers of different crystal phases for transesterification of alcohols with dimethyl carbonate, Appl. Catal. B Environ. 150(2014) 330-337.
[13] H. Liu, J. Chen, L. Chen, Y. Xu, X. Guo, D. Fang, Carbon nanotube-based solid sulfonic acids as catalysts for production of fatty acid methyl ester via transesterification and esterification, ACS Sustain. Chem. Eng. 4(2016) 3140-3150.
[14] H. Guo, X. Qi, L. Li, R.L. Smith Jr., Hydrolysis of cellulose over functionalized glucosederived carbon catalyst in ionic liquid, Bioresour. Technol. 116(2012) 355-359.
[15] M. Liu, S. Jia, Y. Gong, C. Song, X. Guo, Effective hydrolysis of cellulose into glucose over sulfonated sugar-derived carbon in an ionic liquid, Ind. Eng. Chem. Res. 52(2013) 8167-8173.
[16] F. Guo, Z. Fang, T.-J. Zhou, Conversion of fructose and glucose into 5-hydroxymethylfurfural with lignin-derived carbonaceous catalyst under microwave irradiation in dimethyl sulfoxide-ionic liquid mixtures, Bioresour. Technol. 112(2012) 313-318.
[17] X. Zhang, K. Wilson, A.F. Lee, Heterogeneously catalyzed hydrothermal processing of C-5-C-6 sugars, Chem. Rev. 116(2016) 12328-12368.
[18] M. Sevilla, A.B. Fuertes, The production of carbon materials by hydrothermal carbonization of cellulose, Carbon 47(2009) 2281-2289.
[19] W.J. Liu, H. Jiang, H.Q. Yu, Development of biochar-based functional materials:toward a sustainable platform carbon material, Chem. Rev. 115(2015) 12251-12285.
[20] J.T. Yu, A.M. Dehkhoda, N. Ellis, Development of biochar-based catalyst for transesterification of canola oil, Energy Fuel 25(2011) 337-344.
[21] X. Mo, E. Lotero, C. Lu, Y. Liu, J.G. Goodwin, A novel sulfonated carbon composite solid acid catalyst for biodiesel synthesis, Catal. Lett. 123(2008) 1-6.
[22] L. Hu, G. Zhao, X. Tang, Z. Wu, J. Xu, L. Lin, S. Liu, Catalytic conversion of carbohydrates into 5-hydroxymethylfurfural over cellulose-derived carbonaceous catalyst in ionic liquid, Bioresour. Technol. 148(2013) 501-507.
[23] Z. Xu, W. Li, Z. Du, H. Wu, H. Jameel, H.M. Chang, L. Ma, Conversion of corn stalk into furfural using a novel heterogeneous strong acid catalyst in gamma-valerolactone, Bioresour. Technol. 198(2015) 764-771.
[24] J. Wang, W. Xu, J. Ren, X. Liu, G. Lu, Y. Wang, Efficient catalytic conversion of fructose into hydroxymethylfurfural by a novel carbon-based solid acid, Green Chem. 13(2011) 2678-2681.
[25] B. Zhang, J. Ren, X. Liu, Y. Guo, Y. Guo, G. Lu, Y. Wang, Novel sulfonated carbonaceous materials from p-toluenesulfonic acid/glucose as a high-performance solid-acid catalyst, Catal. Commun. 11(2010) 629-632.
[26] T. Liu, Z. Li, W. Li, C. Shi, Y. Wang, Preparation and characterization of biomass carbon-based solid acid catalyst for the esterification of oleic acid with methanol, Bioresour. Technol. 133(2013) 618-621.
[27] M. Hara, T. Yoshida, A. Takagaki, T. Takata, J.N. Kondo, S. Hayashi, K. Domen, A carbon material as a strong protonic acid, Angew. Chem. Int. Ed. 43(2004) 2955-2958.
[28] M. Okamura, A. Takagaki, M. Toda, J.N. Kondo, K. Domen, T. Tatsumi, M. Hara, S. Hayashi, Acid-catalyzed reactions on flexible polycyclic aromatic carbon in amorphous carbon, Chem. Mater. 18(2006) 3039-3045.
[29] H. Yan, Y. Yang, D. Tong, X. Xiang, C. Hu, Catalytic conversion of glucose to 5-hydroxymethylfurfural over SO₄^2-/ZrO₂ and SO₄^2-/ZrO₂-Al₂O₃ solid acid catalysts, Catal. Commun. 10(2009) 1558-1563.
[30] J. Zhao, C. Zhou, C. He, Y. Dai, X. Jia, Y. Yang, Efficient dehydration of fructose to 5-hydroxymethylfurfural over sulfonated carbon sphere solid acid catalysts, Catal. Today 264(2016) 123-130.
[31] Q. Shu, J. Gao, Z. Nawaz, Y. Liao, D. Wang, J. Wang, Synthesis of biodiesel from waste vegetable oil with large amounts of free fatty acids using a carbon-based solid acid catalyst, Appl. Energy 87(2010) 2589-2596.
[32] H. Yu, S. Niu, C. Lu, J. Li, Y. Yang, Sulfonated coal-based solid acid catalyst synthesis and esterification intensification under ultrasound irradiation, Fuel 208(2017) 101-110.
[33] L.M. Correia, N.d.S. Campelo, D.S. Novaes, C.L. Cavalcante Jr., J. Antonio Cecilia, E. Rodriguez-Castellon, R.S. Vieira, Characterization and application of dolomite as catalytic precursor for canola and sunflower oils for biodiesel production, Chem. Eng. J. 269(2015) 35-43.
[34] L.H. Chin, A.Z. Abdullah, B.H. Hameed, Sugar cane bagasse as solid catalyst for synthesis of methyl esters from palm fatty acid distillate, Chem. Eng. J. 183(2012) 104-107.
[35] L. Roldan, E. Pires, J.M. Fraile, E. Garcia-Bordeje, Impact of sulfonated hydrothermal carbon texture and surface chemistry on its catalytic performance in esterification reaction, Catal. Today 249(2015) 153-160.
[36] J.M. Fraile, E. Garcia-Bordeje, L. Roldan, Deactivation of sulfonated hydrothermal carbons in the presence of alcohols:evidences for sulfonic esters formation, J. Catal. 289(2012) 73-79.
[37] J. Zhang, J. Chen, Modified solid acids derived from biomass based cellulose for onestep conversion of carbohydrates into ethyl levulinate, J. Energy Chem. 25(2016) 747-753.
[38] K. Malins, J. Brinks, V. Kampars, I. Malina, Esterification of rapeseed oil fatty acids using a carbon-based heterogeneous acid catalyst derived from cellulose, Appl. Catal. A Gen. 519(2016) 99-106.