Citation: | Wenguang Zhao, Hui Ding, Jie Zhu, Xianxiang Liu, Qiong Xu, Dulin Yin. Esterification of levulinic acid into n-butyl levulinate catalyzed by sulfonic acid-functionalized lignin-montmorillonite complex[J]. Journal of Bioresources and Bioproducts, 2020, 5(4): 291-299. doi: 10.1016/j.jobab.2020.10.008 |
Badgujar, K.C., Badgujar, V.C., Bhanage, B.M., 2020. A review on catalytic synthesis of energy rich fuel additive levulinate compounds from biomass derived levulinic acid. Fuel Process. Technol. 197, 106213. http://www.sciencedirect.com/science/article/pii/S0378382019309142
|
Bonacci, S., Nardi, M., Costanzo, P., de Nino, A., Gioia, M.L.D., Oliverio, M., Procopio, A., 2019. Montmorillonite K10-catalyzed solvent-free conversion of furfural into cyclopentenones. Catalysts 9, 301. http://www.wanfangdata.com.cn/details/detail.do?_type=perio&id=MDPI000000218319
|
Cao, J.J., Ma, M.W., Liu, J.C., Yang, Y.Q., Liu, H., Xu, X.L., Huang, J.H., Yue, H.J., Tian, G., Feng, S.H., 2019. Highly effective transformation of carbohydrates to 5-Hydroxymethylfurfural with Al-montmorillonite as catalyst. Appl. Catal. A:Gen. 571, 96-101. doi: 10.1016/j.apcata.2018.12.011
|
Christensen, E., Williams, A., Paul, S., Burton, S., McCormick, R.L., 2011. Properties and performance of levulinate esters as diesel blend components. Energy Fuels 25, 5422-5428. doi: 10.1021/ef201229j
|
Ciptonugroho, W., Al-Shaal, M.G., Mensah, J.B., Palkovits, R., 2016. One pot synthesis of WOx/mesoporous-ZrO2 catalysts for the production of levulinic-acid esters. J. Catal. 340, 17-29. doi: 10.1016/j.jcat.2016.05.001
|
Cirujano, F.G., Corma, A., Llabrés i Xamena, F.X., 2015. Conversion of levulinic acid into chemicals:synthesis of biomass derived levulinate esters over Zr-containing MOFs. Chem. Eng. Sci. 124, 52-60. doi: 10.1016/j.ces.2014.09.047
|
Das, J., Parida, K.M., 2007. Heteropoly acid intercalated Zn/Al HTlc as efficient catalyst for esterification of acetic acid using n-butanol. J. Mol. Catal. A:Chem. 264, 248-254. doi: 10.1016/j.molcata.2006.09.033
|
Demolis, A., Essayem, N., Rataboul, F., 2014. Synthesis and applications of alkyl levulinates. ACS Sustain. Chem. Eng. 2, 1338-1352. doi: 10.1021/sc500082n
|
Dharne, S., Bokade, V.V., 2011. Esterification of levulinic acid to n-butyl levulinate over heteropolyacid supported on acid-treated clay. J. Nat. Gas Chem. 20, 18-24. doi: 10.1016/S1003-9953(10)60147-8
|
Enumula, S.S., Gurram, V.R.B., Chada, R.R., Burri, D.R., Kamaraju, S.R.R., 2017. Clean synthesis of alkyl levulinates from levulinic acid over one pot synthesized WO3-SBA-16 catalyst. J. Mol. Catal. A:Chem. 426, 30-38. http://www.wanfangdata.com.cn/details/detail.do?_type=perio&id=20ab26420375266499b249ce87e8af7b
|
Gao, J., Kong, W.X., Zhou, L.Y., He, Y., Ma, L., Wang, Y., Yin, L.Y., Jiang, Y.J., 2017. Monodisperse core-shell magnetic organosilica nanoflowers with radial wrinkle for lipase immobilization. Chem. Eng. J. 309, 70-79. doi: 10.1016/j.cej.2016.10.021
|
Gao, Y., Yue, Q.Y., Gao, B.Y., Sun, Y.Y., Wang, W., Li, Q., Wang, Y., 2013. Preparation of high surface area-activated carbon from lignin of papermaking black liquor by KOH activation for Ni(II) adsorption. Chem. Eng. J. 217, 345-353. doi: 10.1016/j.cej.2012.09.038
|
Iborra, M., Tejero, J., Fité, C., Ramírez, E., Cunill, F., 2019. Liquid-phase synthesis of butyl levulinate with simultaneous water removal catalyzed by acid Ion exchange resins. J. Ind. Eng. Chem. 78, 222-231. doi: 10.1016/j.jiec.2019.06.011
|
Kalghatgi, S.G., Bhanage, B.M., 2019. Green syntheses of levulinate esters using ionic liquid 1-Methyl imidazolium hydrogen sulphate[MIM] [HSO4] in solvent free system. J. Mol. Liq. 281, 70-80. doi: 10.1016/j.molliq.2019.02.053
|
Kang, S.M., Fu, J.X., Zhang, G., 2018. From lignocellulosic biomass to levulinic acid:a review on acid-catalyzed hydrolysis. Renew. Sustain. Energy Rev. 94, 340-362. doi: 10.1016/j.rser.2018.06.016
|
Kolvari, E., Koukabi, N., Hosseini, M.M., 2015. Perlite:a cheap natural support for immobilization of sulfonic acid as a heterogeneous solid acid catalyst for the heterocyclic multicomponent reaction. J. Mol. Catal. A:Chem. 397, 68-75. doi: 10.1016/j.molcata.2014.10.026
|
Maheria, K.C., Kozinski, J., Dalai, A., 2013. Esterification of levulinic acid to n-butyl levulinate over various acidic zeolites. Catal. Lett. 143, 1220-1225. doi: 10.1007/s10562-013-1041-3
|
Manikandan, K., Cheralathan, K.K., 2017. Heteropoly acid supported on silicalite-1 possesing intracrystalline nanovoids prepared using biomass-an efficient and recyclable catalyst for esterification of levulinic acid. Appl. Catal. A:Gen. 547, 237-247. doi: 10.1016/j.apcata.2017.09.007
|
Marcel, R., Durillon, T., Djakovitch, L., Fache, F., Rataboul, F., 2019. First example of the use of biosourced alkyl levulinates as solvents for synthetic chemistry:application to the heterogeneously catalyzed heck coupling. ChemistrySelect 4, 3329-3333. doi: 10.1002/slct.201900153
|
Morawala, D., Dalai, A., Maheria, K., 2019. Rice husk mediated synthesis of meso-ZSM-5 and its application in the synthesis of n-butyl levulinate. J. Porous Mater. 26, 677-686. doi: 10.1007/s10934-018-0664-6
|
Morawala, D.H., Dalai, A.K., Maheria, K.C., 2020. Synthesis of n-butyl levulinate using mesoporous zeolite H-BEA catalysts with different catalytic characteristics. Catal. Lett. 150, 1049-1060. doi: 10.1007/s10562-019-03005-0
|
Mukherjee, A., Dumont, M.J., Raghavan, V., 2015. Review:sustainable production of hydroxymethylfurfural and levulinic acid:challenges and opportunities. Biomass Bioenergy 72, 143-183. doi: 10.1016/j.biombioe.2014.11.007
|
Najafi Chermahini, A., Nazeri, M., 2017. Esterification of the levulinic acid with n-butyl and isobutyl alcohols over aluminum-containing MCM-41. Fuel Process. Technol. 167, 442-450. doi: 10.1016/j.fuproc.2017.07.034
|
Nandiwale, K.Y., Bokade, V.V., 2015. Esterification of renewable levulinic acid to n-butyl levulinate over modified H-ZSM-5. Chem. Eng. Technol. 38, 246-252. doi: 10.1002/ceat.201400326
|
Pachamuthu, M.P., Srinivasan, V.V., Karvembu, R., Luque, R., 2019. Preparation of mesoporous stannosilicates SnTUD-1 and catalytic activity in levulinic acid esterification. Microporous Mesoporous Mater. 287, 159-166. doi: 10.1016/j.micromeso.2019.05.061
|
Pavlovic, J., Popova, M., Mihalyi, R.M., Mazaj, M., Mali, G., Kovač, J., Lazarova, H., Rajic, N., 2019. Catalytic activity of SnO2-and SO4/SnO2-containing clinoptilolite in the esterification of levulinic acid. Microporous Mesoporous Mater. 279, 10-18. doi: 10.1016/j.micromeso.2018.12.009
|
Pileidis, F.D., Titirici, M.M., 2016. Levulinic acid biorefineries:new challenges for efficient utilization of biomass. ChemSusChem 9, 562-582. doi: 10.1002/cssc.201501405
|
Shirini, F., Mamaghani, M., Atghia, S.V., 2011. Sulfonic acid-functionalized ordered nanoporous Na+-montmorillonite (SANM):a novel, efficient and recyclable catalyst for the chemoselective N-Boc protection of amines in solventless media. Catal. Commun. 12, 1088-1094. doi: 10.1016/j.catcom.2011.03.030
|
Su, F., Wu, Q.Y., Song, D.Y., Zhang, X.H., Wang, M., Guo, Y.H., 2013. Pore morphology-controlled preparation of ZrO2-based hybrid catalysts functionalized by both organosilica moieties and Keggin-type heteropoly acid for the synthesis of levulinate esters. J. Mater. Chem. 1, 13209-13221. doi: 10.1039/c3ta12412f
|
Sun, X.L., Zhao, X.H., Zu, Y.G., Li, W.G., Ge, Y.L., 2014. Preparing, characterizing, and evaluating ammoniated lignin diesel from papermaking black liquor. Energy Fuels 28, 3957-3963. doi: 10.1021/ef5008165
|
Tian, Y., Zhang, R.Q., Zhao, W.G., Wen, S., Xiang, Y.P., Liu, X.X., 2020. A new sulfonic acid-functionalized organic polymer catalyst for the synthesis of biomass-derived alkyl levulinates. Catal. Lett. 15, doi: 10.1007/s10562-020-03253-5.
|
Varadwaj, G.B.B., Parida, K., Nyamori, V.O., 2016. Transforming inorganic layered montmorillonite into inorganic-organic hybrid materials for various applications:a brief overview. Inorg. Chem. Front. 3, 1100-1111. http://pubs.rsc.org/en/content/articlepdf/2016/qi/c6qi00179c
|
Xu, X.L., Zhang, X.L., Zou, W.J., Yue, H.J., Tian, G., Feng, S.H., 2015. Conversion of carbohydrates to methyl levulinate catalyzed by sulfated montmorillonite. Catal. Commun. 62, 67-70. doi: 10.1016/j.catcom.2015.01.011
|
Yan, L., Yao, Q., Fu, Y., 2017. Conversion of levulinic acid and alkyl levulinates into biofuels and high-value chemicals. Green Chem. 19, 5527-5547. doi: 10.1039/C7GC02503C
|
Yang, F., Tang, J.J., 2019. Catalytic upgrading of renewable levulinic acid to levulinate esters using perchloric acid decorated nanoporous silica gels. ChemistrySelect 4, 1403-1409. doi: 10.1002/slct.201803608
|
Yang, J.F., Li, G.Y., Zhang, L.L., Zhang, S.F., 2018. Efficient production of N-butyl levulinate fuel additive from levulinic acid using amorphous carbon enriched with oxygenated groups. Catalysts 8, 14. http://www.wanfangdata.com.cn/details/detail.do?_type=perio&id=MDPI000000202942
|
Yi, X.L., He, W., Zhang, X.D., Yue, Y.Z., Yang, G.H., Wang, Z.Y., Zhou, M.J., Wang, L.Z., 2017. Graphene-like carbon sheet/Fe3O4 nanocomposites derived from soda papermaking black liquor for high performance lithium Ion batteries. Electrochimica Acta 232, 550-560. doi: 10.1016/j.electacta.2017.02.130
|
Zhang, H., Li, H., Hu, Y.L., Venkateswara Rao, K.T., Xu, C., Yang, S., 2019. Advances in production of bio-based ester fuels with heterogeneous bifunctional catalysts. Renew. Sustain. Energy Rev. 114, 109296. http://www.researchgate.net/publication/336184868_Advances_in_production_of_bio-based_ester_fuels_with_heterogeneous_bifunctional_catalysts
|
Zhang, J., Wu, S., Li, B., Zhang, H., 2012. Advances in the catalytic production of valuable levulinic acid derivatives. ChemCatChem 4, 1230-1237. doi: 10.1002/cctc.201200113
|
Zhou, L.Y., He, Y., Ma, L., Jiang, Y.J., Huang, Z.H., Yin, L.Y., Gao, J., 2018. Conversion of levulinic acid into alkyl levulinates:Using lipase immobilized on meso-molding three-dimensional macroporous organosilica as catalyst. Bioresour. Technol. 247, 568-575. doi: 10.1016/j.biortech.2017.08.134
|
Zhou, S.L., Liu, X.X., Lai, J.H., Zheng, M., Liu, W.Z., Xu, Q., Yin, D.L., 2019. Covalently linked organo-sulfonic acid modified titanate nanotube hybrid nanostructures for the catalytic esterification of levulinic acid with n-butyl alcohol. Chem. Eng. J. 361, 571-577. doi: 10.1016/j.cej.2018.12.111
|