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

doi:10.1016/j.cjche.2018.07.019

中国化学工程学报 ›› 2019, Vol. 27 ›› Issue (5): 1067-1072.DOI: 10.1016/j.cjche.2018.07.019

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

Donglei Mao, Xingguang Zhang, Xiongfei Zhang, Mingmin Jia, Jianfeng Yao

College of Chemical Engineering, Jiangsu Key Lab for the Chemistry & Utilization of Agricultural and Forest Biomass, Nanjing Forestry University, Nanjing 210037, China

收稿日期:2018-06-06 修回日期:2018-07-12 出版日期:2019-05-28 发布日期:2019-06-27
通讯作者: Jianfeng Yao
基金资助:
Supported by the Natural Science Key Project of the Jiangsu Higher Education Institutions (15KJA220001), Jiangsu Province Six Talent Peaks Project (2016-XCL-043), the Young Natural Science Foundation of Jiangsu Province (BK20170918), and the National Natural Science Foundation of China (NNSFC 21706134).

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

Donglei Mao, Xingguang Zhang, Xiongfei Zhang, Mingmin Jia, Jianfeng Yao

College of Chemical Engineering, Jiangsu Key Lab for the Chemistry & Utilization of Agricultural and Forest Biomass, Nanjing Forestry University, Nanjing 210037, China

Received:2018-06-06 Revised:2018-07-12 Online:2019-05-28 Published:2019-06-27
Contact: Jianfeng Yao
Supported by:
Supported by the Natural Science Key Project of the Jiangsu Higher Education Institutions (15KJA220001), Jiangsu Province Six Talent Peaks Project (2016-XCL-043), the Young Natural Science Foundation of Jiangsu Province (BK20170918), and the National Natural Science Foundation of China (NNSFC 21706134).

摘要/Abstract

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

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

Donglei Mao, Xingguang Zhang, Xiongfei Zhang, Mingmin Jia, Jianfeng Yao. Glucose-derived solid acids and their stability enhancement for upgrading biodiesel via esterification[J]. 中国化学工程学报, 2019, 27(5): 1067-1072.

参考文献

[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.

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

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

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	Junyang Liu, Luming Wang, Yuhang Bian, Chunshan Li, Zengxi Li, Jie Li. Liquid-phase esterification of methacrylic acid with methanol catalyzed by cation-exchange resin in a fixed bed reactor: Experimental and kinetic studies[J]. 中国化学工程学报, 2023, 58(6): 1-10.
[2]	Zhiwei Wang, Yu Zhang, Zhi Zhang, Daowei Zhou, Zhikai Cao, Yong Sha. Investigation on catalytic distillation for ethyl acetate production with different catalytic packing structures[J]. 中国化学工程学报, 2023, 53(1): 63-72.
[3]	Monique Juna L. Leite, Ingrid Ramalho Marques, Mariane Carolina Proner, Pedro H.H. Araújo, Alan Ambrosi, Marco Di Luccio. Catalytically active membranes for esterification: A review[J]. 中国化学工程学报, 2023, 53(1): 142-154.
[4]	Tengjie Wang, Wenkai Li, Xuehui Ge, Ting Qiu, Xiaoda Wang. Kinetics measurement of ethylene-carbonate synthesis via a fast transesterification by microreactors[J]. 中国化学工程学报, 2023, 53(1): 243-250.
[5]	Xinhai Zhou, Dawei Zhou, Xinhui Bao, Yang Zhang, Jie Zhou, Fengxue Xin, Wenming Zhang, Xiujuan Qian, Weiliang Dong, Min Jiang, Katrin Ochsenreither. Production of palmitoleic acid by oleaginous yeast Scheffersomyces segobiensis DSM 27193 using systematic dissolved oxygen regulation strategy[J]. 中国化学工程学报, 2023, 53(1): 324-331.
[6]	Xiaojiang Liang, Fengjiao Wu, Qinglong Xie, Zhenyu Wu, Jinjin Cai, Congwen Zheng, Junhong Fu, Yong Nie. Insights into biobased epoxidized fatty acid isobutyl esters from biodiesel: Preparation and application as plasticizer[J]. 中国化学工程学报, 2022, 44(4): 41-50.
[7]	Qing Shu, Xinyuan Liu, Yanting Huo, Yuhui Tan, Caixia Zhang, Laixi Zou. Construction of a Brönsted-Lewis solid acid catalyst La-PW-SiO₂/SWCNTs based on electron withdrawing effect of La(III) on π bond of SWCNTs for biodiesel synthesis from esterification of oleic acid and methanol[J]. 中国化学工程学报, 2022, 44(4): 351-362.
[8]	Saboura Ashkevarian, Jalil Badraghi, Fatemeh Mamashli, Behdad Delavari, Ali Akbar Saboury. Covalent immobilization and characterization of Rhizopus oryzae lipase on core-shell cobalt ferrite nanoparticles for biodiesel production[J]. 中国化学工程学报, 2021, 37(9): 128-136.
[9]	Chunxiao Zhang, Yingjie Li, Zhiguo Bian, Wan Zhang, Zeyan Wang. Simultaneous CO₂ capture and thermochemical heat storage by modified carbide slag in coupled calcium looping and CaO/Ca(OH)₂ cycles[J]. 中国化学工程学报, 2021, 36(8): 76-85.
[10]	Xiaoda Wang, Wenkai Li, Shiwei Wang, Qinglian Wang, Ling Li, Hongxing Wang, Ting Qiu. Reaction kinetics for the heterogeneously resin-catalyzed and homogeneously self-catalyzed esterification of thioglycolic acid with 2-ethyl-1-hexanol[J]. 中国化学工程学报, 2021, 36(8): 111-119.
[11]	Yishan Zhou, Hao Qin, Hongye Cheng, Lifang Chen, Bingjian Zhang, Zhiwen Qi. Reactive extraction for synthesizing long chain ester butyl hexanoate intensified by deep eutectic solvent[J]. 中国化学工程学报, 2021, 36(8): 120-127.
[12]	Sunita Malik, Poonam Jangra Darolia, S. K. Garg, V. K. Sharma. Densities and excess molar volumes of mixtures containing diesel, biodiesel and alkanols at temperatures from 288.15 to 313.15 K[J]. 中国化学工程学报, 2021, 34(6): 198-207.
[13]	P. Vignesh, A.R. Pradeep Kumar, N. Shankar Ganesh, V. Jayaseelan, K. Sudhakar. A review of conventional and renewable biodiesel production[J]. 中国化学工程学报, 2021, 40(12): 1-17.
[14]	Subbaiyan Naveen, Kannappan Panchamoorthy Gopinath, Rajagopal Malolan, Ramesh Sai Jayaraman, Krishnan Aakriti, Jayaseelan Arun. A solar reactor for bio-diesel production from Pongamia oil: Studies on transesterfication process parameters and energy efficiency[J]. 中国化学工程学报, 2021, 40(12): 218-224.
[15]	Majid Masteri-Farahani, Samaneh Shahsavarifar. Chemical functionalization of chitosan biopolymer and chitosan-magnetite nanocomposite with sulfonic acid for acid-catalyzed reactions[J]. 中国化学工程学报, 2021, 39(11): 154-161.