Abstract
Furfural (FFR) is one of the most important biomass-derived chemicals. Its large-scale availability calls for the exploration of new transformation methods for further valorization. Herein, we demonstrate that Ru nanoparticles (Ru NPs)-supported on a sulfonated carbon layer coated SBA-15 can be employed as an efficient bi-functional catalyst for one step conversion of FFR into 1,4-pentanediol (1,4-PeDO). The optimum bi-functional catalyst can afford the full the conversion of FFR and 86% selectivity to 1,4-PeDO. The catalysts have been characterized thoroughly by using a complementary combination of powder X-ray diffraction, N2 adsorption–desorption, scanning/transmission electron microscopy, Fourier transform infrared spectroscopy, elemental analysis, and X-ray photoelectron spectroscopy. The characterization revealed that acidic groups (–SO3H) have been introduced on the surface of the carbon layer coated SBA-15 support after sulfonation with 98% H2SO4 and the surface acidity can be tuned facilely by the sulfonating time. Meantime, Ru(0) sites was highly dispersed via an impregnation and sequential reduction and directly adjacent to the surface –SO3H group. There existed an electronic interaction between Ru(0) sites and sulfonic groups, in which the electronic transfer from sulfonic sites to Ru(0) sites occurred. Brönsted acid sites (–SO3H) have a significant influence on the FFR conversion and the selectivity to 1,4-PeDO. The ordered mesoporous structure, the appropriate density of acid sites and the electron-rich Ru(0) sites accounted for the the excellent performance of the catalyst for an efficient production of 1,4-PeDO from FFR.
Graphic Abstract
Similar content being viewed by others
References
Sudarsanam P, Peeters E, Makshina EV, Parvulescu VI, Sels BF (2019) Chem Soc Rev 48:2366–2421
Zhou CH, Xia X, Lin CX, Tong DS, Beltramini J (2011) Chem Soc Rev 40:5588–5617
Li C, Zhao X, Wang A, Huber GW, Zhang T (2015) Chem Rev 115:11559–11624
Zhang Z, Song J, Han B (2017) Chem Rev 117:6834–6880
Schutyser W, Renders T, Van den Bosch S, Koelewijn SF, Beckham GT, Sels BF (2018) Chem Soc Rev 47:852–908
Alonso DM, Bond JQ, Dumesic JA (2010) Green Chem 12:1493–1513
Mariscal R, Maireles-Torres P, Ojeda M, Sádaba I, López Granados M (2016) Energy Environ Sci 9:1144–1189
Li X, Jia P, Wang T (2016) ACS Catal 6:7621–7640
Nakagawa Y, Tamura M, Tomishige K (2013) ACS Catal 3:2655–2668
Chatterjee M, Chatterjee A, Ishizaka T, Kawanami H (2018) RSC Adv 8:20190–20201
Liu S, Amada Y, Tamura M, Nakagawa Y, Tomishige K (2014) Catal Sci Technol 4:2535–2549
Musci JJ, Merlo AB, Casella ML (2017) Catal Today 296:43–50
Liu F, Liu Q, Xu J, Li L, Cui YT, Lang R, Li L, Su Y, Miao S, Sun H, Qiao B, Wang A, Jérôme F, Zhang T (2018) Green Chem 20:1770–1776
Mizugaki T, Yamakawa T, Nagatsu Y, Maeno Z, Mitsudome T, Jitsukawa K, Kaneda K (2014) ACS Sustain Chem Eng 2:2243–2247
Koso S, Furikado I, Shimao A, Miyazawa T, Kunimori K, Tomishige K (2009) Chem Commun, 2035–2037
Koso S, Ueda N, Shinmi Y, Okumura K, Kizuka T, Tomishige K (2009) J Catal 267:89–92
Chen KY, Koso S, Kubota T, Nakagawa Y, Tomishige K (2010) ChemCatChem 2:547–555
Koso S, Nakagawa Y, Tomishige K (2011) J Catal 280:221–229
Koso S, Watanabe H, Okumura K, Nakagawa Y, Tomishige K (2012) Appl Catal B 111–112:27–37
Xu W, Wang H, Liu X, Ren J, Wang Y, Lu G (2011) Chem Commun 47:3924–3926
Liu S, Amada Y, Tamura M, Nakagawa Y, Tomishige K (2014) Green Chem 16:617–626
Li M, Li G, Li N, Wang A, Dong W, Wang X, Cong Y (2014) Chem Commun 50:1414–1416
Misugaki T, Nagatsu Y, Togo K, Maeno Z, Mitsudome T, Jitsukawa K, Kaneda K (2015) Green Chem 17:5136–5139
Ren D, Wan X, Jin F, Song Z, Liu Y, Huo Z (2016) Green Chem 18:5999–6003
Lv J, Rong Z, Sun L, Liu C, Lu AH, Wang Y, Qu J (2018) Catal Sci Technol 8:975–979
Cui J, Tan J, Zhu Y, Cheng F (2018) Chemsuschem 11:1316–1320
Liu Q, Qiao B, Liu F, Zhang L, Su Y, Wang A, Zhang T (2020) Green Chem 22:3532–3538
Rodiansono R, Astuti MD, Hara T, Ichikuni N, Shimazu S (2019) Green Chem 21:2307–2315
Ye L, Han Y, Bai H, Lu X (2020) ACS Sustain Chem Eng 8:7403–7413
Tang K, Xie S, Cofield GR, Yang X, Tian E, Lin H (2018) Energy Technol 6:1826–1831
Yang G, Pidko EA, Hensen EJ (2012) J Catal 295:122–132
Lv W, Liao Y, Zhu Y, Liu J, Zhu C, Wang C, Xu Y, Zhang Q, Chen G, Ma L (2020) Cellulose 27:799–823
Li T, Lin H, Ouyang X, Qiu X, Wan Z, Ruan T (2020) Fuel 278:118324
Qian W, Lin L, Qiao Y, Zhao X, Xu Z, Gong H, Li D, Chen M, Huang R, Hou Z (2019) Appl Catal A 585:117–183
Chiang HL, Wu TN, Zeng LX (2019) Microporous Mesoporous Mater 279:286–292
Xiao Y, Hill JM (2020) Chemosphere 248:125981
Golub KW, Sulmonetti TP, Darunte LA, Shealy MS, Jones CW (2019) ACS Appl Nano Mater 2:6040–6056
Pisal DS, Yadav GD (2019) ACS Omega 4:1201–1214
Cai X, Wang Q, Liu Y, Xie J, Long Z, Zhou Y, Wang J (2016) ACS Sustain Chem Eng 4:4986–4996
Zhang Z, Ding L, Gu J, Li Y, Xue N, Peng L, Zhu Y, Ding W (2017) Catal Sci Technol 7:5953–5963
Tian H, Lin Z, Xu F, Zheng J, Zhuang X, Zhuang Y, Feng X (2016) Small 12:3155–3163
Wu D, Xu Q, Qian J, Li X, Sun Y (2019) Chem Eur J 25:3105–3111
Zheng F, Yang Y, Chen Q (2014) Nat Commun 5:5261–5270
Andrea CF, Denis MB (2013) Nat Nanotechnol 8:235–246
Zhu W, Yang H, Chen J, Chen C, Guo L, Gan H, Zhao X, Hou Z (2014) Green Chem 16:1534–1542
Liu F, Lee JY, Zhou WJ (2006) Small 2:121–128
Song Y, Yang J, Wang K, Haller S, Wang Y, Wang C, Xia Y (2016) Carbon 96:955–964
Wu ZS, Winter A, Chen L, Sun Y, Turchanin A, Feng X, Mullen K (2012) Adv Mater 24:5130–5135
Castro AA, Morales F, Romero M, Conde-Gallardo A, Escamilla R (2018) J Mater Sci 53:8067–8073
Pirmoradi M, Janulaitis N, Gulotty RJ Jr, Kastner JR (2020) ACS Omega 5:7836–7849
Choura M, Belgacem NM, Gandini A (1996) Macromolecules 29:3839–3850
Huang YB, Yang T, Lin YT, Zhu YZ, Li LC, Pan H (2018) Green Chem 20:1323–1334
Acknowledgements
The authors are grateful for support from the National Natural Science Foundation of China (21773061, 21978095), the innovation Program of Shanghai Municipal Education Commission (15ZZ031).
Author information
Authors and Affiliations
Corresponding authors
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Cui, K., Qian, W., Shao, Z. et al. Ru Nanoparticles on a Sulfonated Carbon Layer Coated SBA-15 for Catalytic Hydrogenation of Furfural into 1, 4-pentanediol. Catal Lett 151, 2513–2526 (2021). https://doi.org/10.1007/s10562-020-03520-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-020-03520-5