Abstract
Biomass, as the most abundant and renewable organic carbon source, can be upgraded into various value-added platform molecules. To implement more sustainable and economic catalytic biomass valorization, reusable heterogeneous catalysts would be one of the preferable choices. In this work, a series of phosphotungstic acid-based solid hybrids were produced by assembly of phosphotungstic acid with different pyridines using a facile solvothermal method. The obtained 3- phenylpyridine-phosphotungstate hybrid displayed superior catalytic performance in the upgrade of fructose to methyl levulinate with 71.2% yield and 83.2% fructose conversion at 140 ºC for 8 h in methanol, a bio-based and environmentally friendly solvent, which was probably due to its relatively large pore size and high hydrophobicity. This low-cost and eco-friendly catalytic process could be simply operated in a single pot without cumbersome separation steps. In addition, the 3- phenylpyridine-phosphotungstate catalyst was able to be reused for four times with little deactivation.
Keywords: Biomass conversion, biofuel, alkyl levulinate, inorganic-organic hybrid, heterogeneous catalysis, green chemistry.
Graphical Abstract
[1]
Li, H.; Riisager, A.; Saravanamurugan, S.; Pandey, A.; Sangwan, R.S.; Yang, S.; Luque, R. Carbon-increasing catalytic strategies for upgrading biomass into energy-intensive fuels and chemicals. ACS Catal., 2017, 8, 148-187.
[2]
Wangchuk, T.; He, C.; Knibbs, L.D.; Mazaheri, M.; Morawska, L. A pilot study of traditional indoor biomass cooking and heating in rural Bhutan: Gas and particle concentrations and emission rates. Indoor Air, 2017, 27, 160-168.
[3]
Filiciotto, L.; Luque, R. Biomass promises: A bumpy road to a renewable economy. Curr. Green Chem., 2018, 5(1), 47-59.
[4]
Kimming, M.; Sundberg, C.; Nordberg, A.; Baky, A.; Bernesson, S.; Hansson, P.A. Replacing fossil energy for organic milk production-potential biomass sources and greenhouse gas emission reductions. J. Clean. Prod., 2015, 106, 400-407.
[5]
Li, H.; Zhao, W.; Saravanamurugan, S.; Dai, W.; He, J.; Meier, S.; Yang, S.; Riisager, A. Control of selectivity in hydrosilane-promoted heterogeneous palladium-catalysed reduction of furfural and aromatic carboxides. Commun. Chem., 2018, 1, 32.
[6]
Zhang, D.H.; Wang, J.Q.; Lin, Y.G.; Si, Y.L.; Huang, C.; Yang, J.; Huang, B.; Li, W. Present situation and future prospect of renewable energy in China. Renew. Sustain. Energy Rev., 2017, 76, 865-871.
[7]
Alcantara, A.R.; de Maria, P.D. Recent advances on the use of 2-methyltetrahydrofuran (2-MeTHF) in biotransformations. Curr. Green Chem., 2018, 5(2), 86-103.
[8]
Oreggioni, G.D.; Singh, B.; Cherubini, F.; Guest, G.; Lausselet, C.; Luberti, M.; Strømman, A.H. Environmental assessment of biomass gasification combined heat and power plants with absorptive and adsorptive carbon capture units in Norway. Int. J. Greenh. Gas Control, 2017, 57, 162-172.
[9]
Shikinaka, K.; Sotome, H.; Kubota, Y.; Tominaga, Y.; Nakamura, M.; Navarro, R.R.; Otsuka, Y. A small amount of nanoparticulated plant biomass, lignin, enhances the heat tolerance of poly (ethylene carbonate). J. Mater. Chem. A, 2018, 6(3), 837-839.
[10]
Xu, S.C.; Lamm, M.E.; Rahman, M.A.; Zhang, X.Z.; Zhu, T.Y.; Zhao, Z.D.; Tang, C.B. Renewable atom-efficient polyesters and thermosetting resins derived from high oleic soybean oil. Green Chem., 2018, 20(5), 1106-1113.
[11]
Jia, R.; Lei, H.Y.; Hino, T.; Arulrajah, A. Environmental changes in Ariake Sea of Japan and their relationships with Isahaya Bay reclamation. Mar. Pollut. Bull., 2018, 135, 832-844.
[12]
Li, H.; Zhao, W.F.; Riisager, A.; Saravanamurugan, S.; Wang, Z.W.; Fang, Z.; Yang, S.A. Pd-Catalyzed in situ domino process for mild and quantitative production of 2,5-dimethylfuran directly from carbohydrates. Green Chem., 2017, 19(9), 2101-2106.
[13]
Liu, Z.L.; Tian, D.; Hu, J.G.; Shen, F.; Long, L.L.; Zhang, Y.Z.; Yang, G.; Zeng, Y.M.; Zhang, J.; He, J.S.; Deng, S.H.; Hu, Y.D. Functionalizing bottom ash from biomass power plant for removing methylene blue from aqueous solution. Sci. Total Environ., 2018, 634, 760-768.
[14]
Luque, R. Catalytic biomass processing: prospects in future biorefineries. Curr. Green Chem., 2015, 2(1), 90-95.
[15]
Malladi, K.T.; Sowlati, T. Biomass logistics: A review of important features, optimization modeling and the new trends. Renew. Sustain. Energy Rev., 2018, 94, 587-599.
[16]
Zhang, S.H.; Yang, M.F.; Shao, J.G.; Yang, H.P.; Zeng, K.; Chen, Y.Q.; Luo, J.; Agblevor, F.A.; Chen, H.P. The conversion of biomass to light olefins on Fe-modified ZSM-5 catalyst: Effect of pyrolysis parameters. Sci. Total Environ., 2018, 628, 350-357.
[17]
Hu, H.W.; Liang, W.X.; Zhang, Y.Y.; Wu, S.Y.; Yang, Q.N.; Wang, Y.B.; Zhang, M.; Liu, Q.J. Multipurpose use of a corncob biomass for the production of polysaccharides and the fabrication of a biosorbent. ACS Sustain. Chem.& Eng., 2018, 6(3), 3830-3839.
[18]
Hu, L.; Xu, J.X.; Zhou, S.Y.; He, A.Y.; Tang, X.; Lin, L.; Xu, J.M.; Zhao, Y.J. Catalytic advances in the production and application of biomass-derived 2, 5-dihydroxymethylfuran. ACS Catal., 2018, 8(4), 2959-2980.
[19]
Tang, X.; Zuo, M.; Li, Z.; Liu, H.; Xiong, C.X.; Zeng, X.H.; Sun, Y.; Hu, L.; Liu, S.J.; Lei, T.Z.; Lin, L. Green processing of lignocellulosic biomass and its derivatives in deep eutectic solvents. ChemSusChem, 2017, 10(13), 2696-2706.
[20]
Zuo, M.; Le, K.; Li, Z.; Jiang, Y.T.; Zeng, X.H.; Tang, X.; Sun, Y.; Lin, L. Green process for production of 5-hydroxymethylfurfural from carbohydrates with high purity in deep eutectic solvents. Ind. Crops Prod., 2017, 99, 1-6.
[21]
Tang, X.; Wei, J.N.; Ding, N.; Sun, Y.; Zeng, X.H.; Hu, L.; Liu, S.J.; Lei, T.Z.; Lin, L. Chemoselective hydrogenation of biomass derived 5-hydroxymethylfurfural to diols: key intermediates for sustainable chemicals, materials and fuels. Renew. Sustain. Energy Rev., 2017, 77, 287-296.
[22]
Wang, J.M.; Zhang, Z.H.; Jin, S.W.; Shen, X.Z. Efficient conversion of carbohydrates into 5-hydroxylmethylfurfan and 5-ethoxymethylfurfural over sufonic acid-functionalized mesoporous carbon catalyst. Fuel, 2017, 192, 102-107.
[23]
Zhang, Z.H.; Huber, G.W. Catalytic oxidation of carbohydrates into organic acids and furan chemicals. Chem. Soc. Rev., 2018, 47(4), 1351-1390.
[24]
Yuan, Z.L.; Liu, B.; Zhou, P.; Zhang, Z.H.; Chi, Q. Aerobic oxidation of biomass-derived 5-hydroxymethylfurfural to 2,5-diformylfuran with cesium-doped manganese dioxide. Catal. Sci. Technol., 2018.
[http://dx.doi.org/10.1039/c8cy01246f]
[http://dx.doi.org/10.1039/c8cy01246f]
[25]
Darji, D.; Alias, Y.; Abd Razak, N.H. Effect of recycled imidazolium-based ionic liquids on biomass from rubber wood. Curr. Green Chem., 2017, 4(2), 74-81.
[26]
Zhang, L.X.; Xi, G.Y.; Yu, K.; Yu, H.; Wang, X.C. Furfural production from biomass-derived carbohydrates and lignocellulosic residues via heterogeneous acid catalysts. Ind. Crops Prod., 2017, 98, 68-75.
[27]
Zhang, L.X.; Xi, G.Y.; Zhang, J.X.; Yu, H.B.; Wang, X.C. Efficient catalytic system for the direct transformation of lignocellulosic biomass to furfural and 5-hydroxymethylfurfural. Bioresour. Technol., 2017, 224, 656-661.
[28]
Guo, T.Y.; Li, X.C.; Liu, X.H.; Guo, Y.; Wang, Y.Q. Catalytic transformation of lignocellulosic biomass into arenes, 5-hydroxymethylfurfural, and furfural. ChemSusChem, 2018, 11, 1-9.
[29]
Huang, X.M.; Ouyang, X.H.; Hendriks, B.M.S.; Gonzalez, O.M.M.; Zhu, J.D.; Korányi, T.I.; Boot, M.D.; Hensen, E.J.M. Selective production of mono-aromatics from lignocellulose over Pd/C catalyst: the influence of acid co-catalysts. Faraday Discuss., 2017, 202, 141-156.
[30]
Qi, B.K.; Vu, A.; Wickramasinghe, S.R.; Qian, X.H. Glucose production from lignocellulosic biomass using a membrane-based polymeric solid acid catalyst. Biomass Bioenergy, 2017, 117, 137-145.
[31]
Bhaumik, P.; Dhepe, P.L. From lignocellulosic biomass to furfural: insight into the active species of a silica-supported tungsten oxide catalyst. ChemCatChem, 2017, 9(14), 2709-2716.
[32]
Xiao, Z.Q.; Zhang, Q.; Chen, T.T.; Wang, X.N.; Fan, Y.; Ge, Q.; Zhai, R.; Sun, R.; Ji, J.B.; Mao, J.W. Heterobimetallic catalysis for lignocellulose to ethylene glycol on nickel-tungsten catalysts: Influenced by hydroxy groups. Fuel, 2018, 230, 332-343.
[33]
Kim, S.; Han, J. Enhancement of energy efficiency and economics of process designs for catalytic co-production of bioenergy and bio-based products from lignocellulosic biomass. Int. J. Energy Res., 2017, 41(11), 1553-1562.
[34]
Feng, J.F.; Jiang, J.C.; Hse, C.Y.; Yang, Z.Z.; Wang, K.; Ye, J.; Xu, J.M. Selective catalytic conversion of waste lignocellulosic biomass for renewable value-added chemicals via directional microwave-assisted liquefaction. Sustain. Energ. Fuels, 2018, 2(5), 1035-1047.
[35]
Grewal, J.; Khare, S.K. One-pot bioprocess for lactic acid production from lignocellulosic agro-wastes by using ionic liquid stable Lactobacillus brevis. Bioresour. Technol., 2018, 251, 268-273.
[36]
Liu, Q.Y.; Zhang, T.; Liao, Y.H.; Cai, C.L.; Tan, J.; Wang, T.J.; Qiu, S.B.; He, M.H.; Ma, L.L. Production of C5/C6 sugar alcohols by hydrolytic hydrogenation of raw lignocellulosic biomass over Zr based solid acids combined with Ru/C. ACS Sustain. Chem.& Eng., 2017, 5, 5940-5950.
[37]
Mika, L.T.; Cséfalvay, E.; Németh, A. Catalytic conversion of carbohydrates to initial platform chemicals: chemistry and sustainability. Chem. Rev., 2017, 118, 505-613.
[38]
Jin, X.L.; Chen, X.L.; Shi, C.H.; Li, M.; Guan, Y.J.; Yu, C.Y.; Yamada, T.; Sacks, E.J.; Peng, J.H. Determination of hemicellulose, cellulose and lignin content using visible and near infrared spectroscopy in Miscanthus sinensis. Bioresour. Technol., 2017, 241, 603-609.
[39]
Wu, Z.Q.; Yang, W.C.; Chen, L.; Meng, H.Y.; Zhao, J.; Wang, S.Z. Morphology and microstructure of co-pyrolysis char from bituminous coal blended with lignocellulosic biomass: effects of cellulose, hemicellulose and lignin. Appl. Therm. Eng., 2017, 116, 24-32.
[40]
Chen, H.Y.; Liu, J.B.; Chang, X.; Chen, D.M.; Xue, Y.; Liu, P.; Lin, H.L.; Han, S. A review on the pretreatment of lignocellulose for high-value chemicals. Fuel Process. Technol., 2017, 160, 196-206.
[41]
Huang, K.F.; Won, W.Y.; Barnett, K.J.; Brentzel, Z.J.; Alonso, D.M.; Huber, G.W.; Dumesic, J.A.; Maravelias, C.T. Improving economics of lignocellulosic biofuels: An integrated strategy for coproducing 1, 5-pentanediol and ethanol. Appl. Energy, 2018, 213, 585-594.
[42]
Luo, Y.P.; Li, Z.; Li, X.L.; Liu, X.F.; Fan, J.J.; Clark, J.H.; Hu, C.W. The production of furfural directly from hemicellulose in lignocellulosic biomass: A review. Catal. Today, 2019, 319, 14-24.
[43]
Jiang, L.Y.; Zhou, L.P.; Chao, J.Y.; Zhao, H.T.; Lu, T.L.; Su, Y.L.; Yang, X.M.; Xu, J. Direct catalytic conversion of carbohydrates to methyl levulinate: Synergy of solid Brønsted acid and Lewis acid. Appl. Catal. B: Environ, 2018, 220, 589-596.
[44]
Li, H.; Zhang, Q.Y.; Bhadury, P.S.; Yang, S. Furan-type compounds from carbohydrates via heterogeneous catalysis. Curr. Org. Chem., 2014, 18, 547-597.
[45]
Dai, J.; Peng, L.C.; Li, H. Intensified ethyl levulinate production from cellulose using a combination of low loading H2SO4 and Al(OTf)3. Catal. Commun., 2018, 103, 116-119.
[46]
Emel’yanenko, V.N.; Altuntepe, E.; Held, C.; Pimerzin, A.A.; Verevkin, S.P. Renewable platform chemicals: Thermochemical study of levulinic acid esters. Thermochim. Acta, 2018, 659, 213-221.
[47]
Liu, Y.; Liu, C.L.; Wu, H.Z.; Dong, W.S. An efficient catalyst for the conversion of fructose into methyl levulinate. Catal. Lett., 2013, 143, 1346-1353.
[48]
Jiang, L.Y.; Zhou, L.P.; Chao, J.Y.; Zhao, H.T.; Lu, T.L.; Su, Y.L.; Yang, X.M.; Xu, J. Direct catalytic conversion of carbohydrates to methyl levulinate: synergy of solid Brønsted acid and Lewis acid. Appl. Catal. B: Environ, 2018, 220, 589-596.
[49]
Babaei, Z.; Chermahini, A.N.; Dinari, M. Alumina-coated mesoporous silica SBA-15 as a solid catalyst for catalytic conversion of fructose into liquid biofuel candidate ethyl levulinate. Chem. Eng. J., 2018, 352, 45-52.
[50]
Li, H.; Fang, Z.; Luo, J.; Yang, S. Direct conversion of biomass components to the biofuel methyl levulinate catalyzed by acid-base bifunctional zirconia-zeolites. Appl. Catal. B: Environ, 2017, 200, 182-191.
[51]
Mohammadbagheri, Z.; Chermahini, A.N. KCC-1/Pr-SO3H as an efficient heterogeneous catalyst for production of n-butyl levulinate from furfuryl alcohol. J. Ind. Eng. Chem., 2018, 62, 401-408.
[52]
Zhang, J.; Wu, S.B.; Li, B.; Zhang, H.D. Advances in the catalytic production of valuable levulinic acid derivatives. ChemCatChem, 2012, 4, 1230-1237.
[53]
Huang, Y.B.; Yang, T.; Lin, Y.T.; Zhu, Y.Z.; Pan, H. Facile and high-yield synthesis of methyl levulinate from cellulose. Green Chem., 2018, 20, 1323-1334.
[54]
vom Stein, T.; Meuresch, M.; Limper, D.; Schmitz, M.; Hölscher, M.; Coetzee, J.; Cole-Hamilton, D.J.; Klankermayer, J.; Leitner, W. Highly versatile catalytic hydrogenation of carboxylic and carbonic acid derivatives using a Ru-triphos complex: molecular control over selectivity and substrate scope. J. Am. Chem. Soc., 2014, 136, 13217-13225.
[55]
He, J.; Wang, Z.W.; Zhao, W.F.; Yang, T.T.; Liu, Y.X.; Yang, S. Catalytic upgrading of biomass-derivedγ-valerolactone to biofuels and valuable chemicals. Curr. Catal., 2017, 6, 31-41.
[56]
Li, H.; Fang, Z.; Smith, R.L.; Yang, S. Efficient valorization of biomass to biofuels with bifunctional solid catalytic materials. Pror. Energy Combust. Sci., 2016, 55, 98-194.
[57]
Yang, T.T.; Li, H.; He, J.; Liu, Y.X.; Zhao, W.F.; Wang, Z.W.; Ji, X.X.; Yang, S. Porous Ti/Zr microspheres for efficient transfer hydrogenation of biobased ethyl levulinate to γ-valerolactone. ACS Omega, 2017, 2, 1047-1054.
[58]
Capello, C.; Fischer, U.; Hungerbühler, K. What is a green solvent? A comprehensive framework for the environmental assessment of solvents. Green Chem., 2007, 9(9), 927-934.
[60]
Feng, J.F.; Jiang, J.C.; Xu, J.M.; Yang, Z.Z.; Wang, K.; Guan, Q.; Chen, S.G. Preparation of methyl levulinate from fractionation of direct liquefied bamboo biomass. Appl. Energy, 2015, 154, 520-527.
[61]
Peng, L.C.; Li, H.; Lin, L.; Chen, K.L. Effect of metal salts existence during the acid-catalyzed conversion of glucose in methanol medium. Catal. Commun., 2015, 59, 10-13.
[62]
Pang, J.F.; Zheng, M.Y.; Li, X.S.; Song, L.; Sun, R.Y.; Sebastian, J.; Wang, A.Q.; Wang, J.H.; Wang, X.D.; Zhang, T. Catalytic conversion of carbohydrates to methyl lactate using isolated tin sites in SBA-15. ChemistrySelect, 2017, 2(1), 309-314.
[63]
Liu, R.L.; Chen, J.Z.; Huang, X.; Chen, L.M.; Ma, L.L.; Li, X.J. Conversion of fructose into 5-hydroxymethylfurfural and alkyl levulinates catalyzed by sulfonic acid-functionalized carbon materials. Green Chem., 2013, 15(10), 2895-2903.
[64]
Pan, H.; Liu, X.F.; Zhang, H.; Yang, K.L.; Huang, S.; Yang, S. Multi-SO3H functionalized mesoporous polymeric acid catalyst for biodiesel production and fructose-to-biodiesel additive conversion. Renew. Energy, 2017, 107, 245-252.
[65]
Song, D.Y.; Sun, Y.N.; Zhang, Q.Q.; Zhang, P.P.; Guo, Y.H.; Leng, J.Y. Fabrication of propylsulfonic acid functionalized SiO2 core/PMO shell structured PrSO3H-SiO2@Si(R)Si nanospheres for the effective conversion of D-fructose into ethyl levulinate. Appl. Catal. A Gen., 2017, 546, 36-46.
[66]
Yu, F.; Zhong, R.Y.; Chong, H.; Smet, M.; Dehaen, W.; Sels, B.F. Fast catalytic conversion of recalcitrant cellulose into alkyl levulinates and levulinic acid in the presence of soluble and recoverable sulfonated hyperbranched poly(arylene oxindole)s. Green Chem., 2017, 19(1), 153-163.
[67]
Wang, Z.W.; Li, H.; Fang, C.J.; Zhao, W.F.; Yang, T.T.; Yang, S. Simply assembled acidic nanospheres for efficient production of 5-ethoxymethylfurfural from 5- hydromethylfurfural and fructose. Energy Technol., 2017, 5(11), 2046-2054.
[68]
An, R.; Xu, G.Z.; Chang, C.; Bai, J.; Fang, S.Q. Efficient one-pot synthesis of n-butyl levulinate from carbohydrates catalyzed by Fe2(SO4)3. J. Energy Chem., 2017, 26(3), 556-563.
[69]
Thapa, I.; Mullen, B.; Saleem, A.; Leibig, C.; Baker, R.T.; Giorgi, J.B. Efficient green catalysis for the conversion of fructose to levulinic acid. Appl. Catal. A Gen., 2017, 539, 70-79.
[70]
Prat, D.; Pardigon, O.; Flemming, H.W.; Letestu, S.; Ducandas, V.; Isnard, P.; Guntrum, E.; Senac, T.; Ruisseau, S.; Cruciani, P.; Hosek, P. Sanofi’s solvent selection guide: a step toward more sustainable processes. Org. Process Res. Dev., 2013, 17(12), 1517-1525.
Call for Papers in Thematic Issues
10 September, 2024
Green concepts' for modern organic synthesis
The 'green revolution', which is literally happening before our eyes and affects every aspect of life, also poses increasingly difficult challenges in the field of chemical synthesis. New solutions and ideas aimed at environmental protection while taking into account the principles of sustainable development are still desired. In this context, ...read more
17 June, 2024
Green Thermochemical Processes for Hydrogen Production: Circular Economy Approach
The Special Issue ?Green Thermochemical Processes for Hydrogen Production: Circular Economy Approach? welcomes research, review and mini-review papers focusing on the study and development of thermochemical processes for the valorization of byproducts, wastes, wastewaters and biomass to Hydrogen in a green and sustainable way. Processes driven by the supply from ...read more
Related Books
Ionic Liquids: Eco-friendly Substitutes for Surface and Interface Applications
Graphene-based Carbocatalysts: Synthesis, Properties and Applications (Volume 2)
Graphene-based Carbocatalysts: Synthesis, Properties and Applications
Electrochemical Biosensors in Practice: Materials and Methods
Photophysics of Supramolecular Architectures
Advanced Physical Chemistry Practical Guide
Article Metrics
59
2