Abstract
The conversion of biomass to biofuels or fuel additives is an important process in the industrial and petrochemical processes. In this investigation, butyl levulinate as a fuel additive was synthesized using a sulfonated CMK-3 catalyst and glucose as a reactant. The effect of two catalysts, which were prepared with two different sulfone reactants, was studied. The influence of other parameters including reaction temperature, reaction time, catalyst amount, and initial glucose amount was evaluated by the Taguchi method. Among the four selected factors, the initial glucose amount was the most effective on the dehydration of glucose to butyl levulinate. Under optimum conditions, using the reaction obtained from experimental design, 70.4% yield and > 99% conversion were calculated for butyl levulinate and glucose, respectively. Also, the conversion of different carbohydrates such as maltose, sucrose, and fructose to butyl levulinate was investigated. Finally, the catalyst reusability was surveyed, and it was observed that the spent catalyst demonstrated high activity in five cycles.
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Stucky GD, Xie Z, Guo C, Zheng N, Wu B (2008) Nonaqueous production of nanostructured anatase with high-energy facets. J Am Chem Soc 130:17563–17567
Liu R, Chen J, Huang X, Chen L, Li X (2013) Conversion of fructose into 5-hydroxymethylfurfural and alkyl levulinates catalyzed by sulfonic acid-functionalized carbon materials. Green Chem 15:2895–2903
Sudarsanam P, Peeters E, Makshina EV, Parvulescu VI, Sels BF (2019) Advances in porous and nanoscale catalysts for viable biomass conversion. Chem Soc Rev 48:2366–2421
Mulik N, Niphadkar P, Bokade V (2019) Synergetic combination of H2Zr1PW12O40 and Sn-beta as potential solid acid catalyst for direct one-step transformation of glucose to ethyl levulinate , a biofuel additive. Environ Prog Sustain 38:13173
Sudarsanam P, Zhong R, Van den Bosch S, Coman SM, Parvulescu VI, Sels BF (2018) Functionalised heterogeneous catalysts for sustainable biomass valorisation. Chem Soc Rev 47:8349–8402
An R, Xu G, Chang C, Bai J, Fang S (2017) Efficient one-pot synthesis of n-butyl levulinate from carbohydrates catalyzed by Fe2(SO4)3. J Energy Chem 26:556–563
Appaturi JN, Johan MR, Ramalingam RJ, Al-Lohedan HA, Vijaya JJ (2017) Efficient synthesis of butyl levulinate from furfuryl alcohol over ordered mesoporous Ti-KIT-6 catalysts for green chemistry applications. RSC Adv 7:55206–55214
Vassilev SV, Vassileva CG (2019) Water-soluble fractions of biomass and biomass ash and their significance for biofuel application. Energy Fuel 33:2763–2777
Proskurina S, Junginger M, Heinimö J, Tekinel B, Vakkilainen E (2019) Global biomass trade for energy—Part 2: Production and trade streams of wood pellets, liquid biofuels, charcoal, industrial roundwood and emerging energy biomass. Biofuels Bioprod Biorefin 13:371–387
Antonetti C, Licursi D, Raspolli Galletti AM (2020) New intensification strategies for the direct conversion of real biomass into platform and fine chemicals: what are the main improvable key aspects? Catalysts 10:961–976
Nandiwale KY, Bokade VV (2015) Esterification of renewable levulinic acid to n-butyl levulinate over modified H-ZSM-5. Chem Eng Technol 38:246–252
Hao R, He J, Zhao L, Zhang Y (2017) HPAs and POM-based ILs catalyzed effective conversion of furfuryl alcohol to alkyl levulinate. ChemistrySelect 2:7918–7924
Liang C, Wang Y, Hu Y, Wu L, Zhang W (2019) Study of a new process for the preparation of butyl levulinate from cellulose. ACS Omega 4:9828–9834
Demma Carà P, Ciriminna R, Shiju NR, Rothenberg G, Pagliaro M (2014) Enhanced heterogeneous catalytic conversion of furfuryl alcohol into butyl levulinate. ChemSusChem 7:835–840
Deng L, Chang C, An R, Qi X, Xu G (2017) Metal sulfates-catalyzed butanolysis of cellulose: butyl levulinate production and optimization. Cellulose 24:5403–5415
Bringué R, Ramírez E, Iborra M, Tejero J, Cunill F (2019) Esterification of furfuryl alcohol to butyl levulinate over ion-exchange resins. Fuel 257:116010
Zhang Z, Dong K, Zhao Z (2011) Efficient conversion of furfuryl alcohol into alkyl levulinates catalyzed by an organic–inorganic hybrid solid acid catalyst. ChemSusChem 4:112–118
Latos P, Szelwicka A, Boncel S, Jurczyk S, Swadźba-Kwaśny M, Chrobok A (2019) Highly efficient synthesis of alkyl levulinates from α-angelica lactone, catalyzed with lewis acidic trifloaluminate ionic liquids supported on carbon nanotubes. ACS Sustain Chem Eng 7:5184–5191
Onkarappa SB, Javoor M, Mal SS, Dutta S (2019) Efficient and scalable production of alkyl levulinates from cellulose-derived levulinic acid using heteropolyacid catalysts. ChemistrySelect 4:2501–2504
Antonetti C, Gori S, Licursi D, Pasini G, Frigo S, López M, Parajó JC, Raspolli Galletti AM (2020) One-pot alcoholysis of the lignocellulosic eucalyptus nitens biomass to n-butyl levulinate, a valuable additive for diesel motor fuel. Catalysts 10:509–530
Hishikawa Y, Yamaguchi M, Kubo S, Yamada T (2013) Direct preparation of butyl levulinate by a single solvolysis process of cellulose. J Wood Sci 59:179–182
Zhou S, Jiang D, Liu X, Chen Y, Yin D (2018) Titanate nanotubes-bonded organosulfonic acid as solid acid catalyst for synthesis of butyl levulinate. RSC Adv 8:3657–3662
Morawala DH, Dalai AK, Maheria KC (2019) Synthesis of n-butyl levulinate using mesoporous zeolite H-BEA catalysts with different catalytic characteristics. Catal Lett 150:1049–1060
Robichaux L, Kendell S (2020) Mechanistic insights into furfuryl alcohol based biofuel production over phosphotungstate catalysts. React Kinet Mech Catal 129:29–40
Wang C, Yuan F, Liu L, Niu X, Zhu Y (2015) Transesterification of tributyrin and dehydration of fructose over a carbon-based solid acid prepared by carbonization and sulfonation of glucose. ChemPlusChem 80:1657–1665
Di Fidio N, Raspolli Galletti AM, Fulignati S, Licursi D, Liuzzi F, De Bari I, Antonetti C (2020) Multi-step exploitation of raw Arundo donax L. for the selective synthesis of second-generation sugars by chemical and biological route. Catalysts 10:79–102
Di Fidio N, Fulignati S, Antonetti C, Raspolli Galletti AM (2019) Microwave-assisted hydrolysis of giant reed hemicellulose in the presence of Amberlyst-70 as heterogeneous catalyst. 27th European Biomass Conference and Exhibition Proceedings (EUBCE) 2019, pp 1329-1336
Melero JA, Morales G, Iglesias J, Paniagua M, Hernández B, Penedo S (2013) Efficient conversion of levulinic acid into alkyl levulinates catalyzed by sulfonic mesostructured silicas. Appl Catal A Gen 466:116–122
Su F, Ma L, Song D, Zhang X, Guo Y (2013) Design of a highly ordered mesoporous H3PW12O40/ZrO2–Si (Ph) Si hybrid catalyst for methyl levulinate synthesis. Green Chem 15:885–890
Chappaz A, Lai J, De Oliveira Vigier K, Morvan D, Wischert R, Corbet M, Doumert B, Trivelli X, Liebens A, Jérôme F (2018) Selective conversion of concentrated feeds of furfuryl alcohol to alkyl levulinates catalyzed by metal triflates. ACS Sustain Chem Eng 6:4405–4411
Saravanamurugan S, Riisager A (2013) Zeolite catalyzed transformation of carbohydrates to alkyl levulinates. ChemCatChem 5:1754–1757
Morales G, Osatiashtiani A, Hernández B, Iglesias J, Melero JA, Paniagua M, Brown DR, Granollers M, Lee AF, Wilson K (2014) Conformal sulfated zirconia monolayer catalysts for the one-pot synthesis of ethyl levulinate from glucose. Chem Commun 50:11742–11745
Jiang L, Zhou L, Chao J, Zhao H, Lu T, Su Y, Yang X, Xu J (2018) Direct catalytic conversion of carbohydrates to methyl levulinate: synergy of solid Brønsted acid and Lewis acid. Appl Catal B Environ 220:589–596
Wang X, Liu R, Waje MM, Chen Z, Yan Y, Bozhilov KN, Feng P (2007) Sulfonated ordered mesoporous carbon as a stable and highly active protonic acid catalyst. Chem Mater 19:2395–2397
Jun S, Joo SH, Ryoo R, Kruk M, Jaroniec M, Liu Z, Ohsuna T, Terasaki O (2000) Synthesis of new, nanoporous carbon with hexagonally ordered mesostructure. J Am Chem Soc 122:10712–10713
Solovyov LA, Shmakov AN, Zaikovskii VI, Joo SH, Ryoo R (2002) Detailed structure of the hexagonally packed mesostructured carbon material CMK-3. Carbon 40:2477–2481
Boehm HP (2002) Surface oxides on carbon and their analysis : a critical assessment. Carbon 40:145–149
Biniak S, Szymański G, Siedlewski J, Świątkowski A (1997) The characterization of activated carbons with oxygen and nitrogen surface groups. Carbon 35:1799–1810
Chang B, Li Y, Guo Y, Yin H, Zhang S, Yang B (2015) SO3H-functionalized hollow mesoporous carbon sphere prepared by simultaneously achieving sulfonation and hollow structure. J Porous Mater 22:629–634
Qiao H, Xia Z, Liu Y, Cui R, Fei Y, Cai Y, Wei Q, Yao Q, Qiao Q (2017) Sonochemical synthesis and high lithium storage properties of ordered Co/CMK-3 nanocomposites. Appl Surf Sci 400:492–497
Babaei Z, Chermahini AN, Dinari M (2018) Alumina-coated mesoporous silica SBA-15 as a solid catalyst for catalytic conversion of fructose into liquid biofuel candidate ethyl levulinate. Chem Eng J 352:45–52
Ahmad E, Alam MI, Pant KK, Haider MA (2016) Catalytic and mechanistic insights into the production of ethyl levulinate from biorenewable feedstocks. Green Chem 18:4804–4823
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We want to thank the Isfahan University of Technology (IRAN) for financial support (Research Council Grant).
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Babaei, Z., Yazdanpanah Esmaeilabad, R., Orash, N. et al. Sulfonated CMK-3: an effective catalyst for the glucose conversion to butyl levulinate as the fuel additive. Biomass Conv. Bioref. 13, 61–71 (2023). https://doi.org/10.1007/s13399-020-01072-7
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DOI: https://doi.org/10.1007/s13399-020-01072-7