Abstract
Alkyl levulinates are important biobased chemicals with great fuel-blending properties and good reactivity. In this work, a new functionalized nitrogen-containing organic polymer bearing sulfonic acid groups (PDVTA-SO3H) was successfully prepared and studied for the esterification of levulinic acid with alcohols to produce alkyl levulinates. The results showed that this sulfonic acid-functionalized organic polymer possessed high catalytic activity, and the yield of n-butyl levulinate reached 97.4% under the mild conditions. PDVTA-SO3H exhibited strong acidic sites and high stability, and would be well expected to be a potential candidate better than some commercial sulfonic solid catalysts for alkyl levulinates production. The catalyst had been reused without any treatment for five times and the results proved its potential for industrial applications.
Graphic Abstract
A new sulfonic acid-functionalized organic polymer showed high activity in the conversion of biomass derived levulinic acid into alkyl levulinates.
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References
Liu XX, Xu Q, Liu JY, Yin DL, Su SP, Ding H (2016) Fuel 164:46–50
Li H, Riisager A, Saravanamurugan S, Pandey A, Sangwan RS, Yang S, Luque R (2018) ACS Catal 8:148–187
Jiang L, Guo HW, Li CZ, Zhou P, Zhang ZH (2019) Chem Sci 10:4458–4468
Song S, Zhang JG, Gozaydin G, Yan N (2019) Angew Chem Int Edit 58:4934–4937
Pinheiro PF, Chaves DM, da Silva MJ (2019) Cellulose 26:7953–7969
Farid MAA, Hassan MA, Taufiq-Yap YH, Ibrahim ML, Othman MR, Ali AAM, Shirai Y (2017) Renew Energ 114:638–643
Zhou SL, Jiang DB, Liu XX, Chen YP, Yin DL (2018) RSC Adv 8:3657–3662
Pasha N, Lingaiah N, Shiva R (2019) Catal Lett 149:2500–2507
Li XY, Xu R, Yang JX, Nie SX, Liu D, Liu Y, Si CL (2019) Ind Crop Prod 130:184–197
Luo WH, Bruijnincx PCA, Weckhuysen BM (2014) J Catal 320:33–41
Lv JK, Rong ZM, Sun LM, Liu CY, Lu AH, Wang Y, Qu JP (2018) Catal Sci Technol 8:975–979
Hegner J, Pereira KC, DeBoef B, Lucht BL (2010) Tetrahedron Lett 51:2356–2358
Fernandes DR, Rocha AS, Mai EF, Mota CJA (2012) Teixeira da Silva V. Appl Catal A-Gen 425–426:199–204
Kong XJ, Wu SX, Li XL, Liu JH (2016) Energ Fuels 30:6500–6504
Tejero MA, Ramírez E, Fité C, Tejero J, Cunill F (2016) Appl Catal A-Gen 517:56–66
Patil CR, Niphadkar PS, Bokade VV, Joshi PN (2014) Catal Commun 43:188–191
Fernandes DR, Rocha AS, Mai EF, Mota CJA (2011) J Energ Chem 20:18–24
Su DS, Perathoner S, Centi G (2013) Chem Rev 113:5782–5816
Pasquale G, Vázquez P, Romanelli G, Baronetti G (2012) Catal Commun 18:115–120
Zhou SL, Liu XX, Lai JH, Zheng M, Liu WZ, Xu Q, Yin DL (2019) Chem Eng J 361:571–577
Sádaba I, López Granados M, Riisager A, Taarning E (2015) Green Chem 17:4133–4145
Gomes R, Bhanja P, Bhaumik A (2016) J Mol Catal A-Chem 411:110–116
Gomes R, Bhaumik A (2015) J Solid State Chem 222:7–11
Mo XH, López DE, Suwannakarn K, Liu Y, Lotero E Jr, GoodwinLu JGCQ (2008) J Catal 254:332–338
Li N, Wang Q, Ullah S, Zheng XC, Peng ZK, Zheng GP (2019) Catal Commun 129:105755
Kuwahara Y, Fujitani T, Yamashita H (2014) Catal Today 237:18–28
Ramli NAS, Zaharudin NH, Amin NAS (2016) J Teknol 79:137–142
Melero JA, Morales G, Iglesias J, Paniagua M, Hernández B, Penedo S (2013) Appl Catal A-Gen 466:116–122
Acknowledgements
The authors gratefully acknowledge the financial support of the National Natural Science Foundation of China (21606082), Hunan Provincial Natural Science Foundation of China (2018JJ3334), and China Postdoctoral Science Foundation (2019M662787).
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Yi Tian and Ruoqi Zhang have contributed equally to this work.
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Tian, Y., Zhang, R., Zhao, W. et al. A New Sulfonic Acid-Functionalized Organic Polymer Catalyst for the Synthesis of Biomass-Derived Alkyl Levulinates. Catal Lett 150, 3553–3560 (2020). https://doi.org/10.1007/s10562-020-03253-5
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DOI: https://doi.org/10.1007/s10562-020-03253-5