Abstract
The Cu/ZnO/Al2O3 catalysts prepared by co-precipitation method were used for the hydrogenation of methyl benzoate to benzyl alcohol. These catalysts were characterized at various stages of preparation by nitrogen adsorption–desorption, X-ray diffraction (XRD), hydrogen temperature-programmed reduction (H2-TPR), and X-ray photoelectron spectroscopy (XPS). The experimental results show that the addition of ZnO to the catalyst greatly improves the selectivity of benzyl alcohol. When the Cu/Zn/Al molar ratio is 2:2:1 and the calcination temperature of the catalyst is 650 °C, the catalyst exhibits very highly catalytic performance. In addition, the effects of reaction temperature, pressure and time were also investigated during the hydrogenation of methyl benzoate to benzyl alcohol. When the methyl benzoate was hydrogenated over this catalyst at 160 °C and 7 MPa of H2 for 10 h, the conversion of methyl benzoate can reach 93.89% and the selectivity of benzyl alcohol is 88%. This effectively catalytic performance can be attributed to the presence of highly dispersed and stable metallic copper nanoparticles, and the weak acidity of the catalyst surface. Besides, the reaction pressure and temperature play a crucial role in the conversion of methyl benzoate and the selectivity of benzyl alcohol.
Graphical Abstract
Application of Cu/ZnO/Al2O3 catalyst in hydrogenation of methyl benzoate to benzyl alcohol.
Similar content being viewed by others
References
Jayesh TB, Itika K, Ramesh Babu GV, Rama Rao KS, .Keri RS, Jadhav AH, Nagaraja BM (2018) Catal Commun 106:73–77
Dub PA, Ikariya T (2012) ACS Catal 2:1718–1741
Adkins HI, Pavlic AA (1947) J Am Chem Soc 69(12):3039–3041
Mozingo R, Folkers K (1948) J Am Chem Soc 70(1):229–231
Seyden-Penne J, Nguyen C, Burdett J (1997) J Organomet Chem 426(1):C22–C23
Santiago MAN, Sánchez-Castillo MA, Cortright RD, Dumesic JA (2000) J Catal 193(1):16–28
Twigg M, Spencer M (2001) Appl Catal A 212:161–174
He L, Cheng H, Liang G, Yu Y, Zhao F (2013) Appl Catal A 452:88–93
Sun Z, Chen X, Wang J, Zhao W, Shao Y, Guo Z, Zhang X, Zhou Z, Sun T, Wang L, Meng H, Zhang H, Chen W (2018) J Catal 357:223–237
Zhu Y, Kong X, Zhu S, Dong F, Zheng H, Zhu Y, Li Y (2015) Appl Catal B 166–167:551–559
Hu Q, Fan G, Zhang S, Yang L, Li F (2015) J Mol Catal A Chem 397:134–141
Zhu Y, Kong X, Cao D, Cui J, Zhu Y, Li Y (2014) ACS Catal 4(4):3675–3681
Yang X, Meng Q, Ding G, Wang Y, Zhu Y, Li Y (2018) Appl Catal A 561(5):78–86
Brands DS, Poels EK, Bliek A (1999) Appl Catal A 184(2):279–289
Scheur FTVD, Linden BVD, Mittelmeijer-Hazeleger MC, Nazloomian JG, Staat LH (1994) Appl Catal A 111(1):63–77
Claus P, Lucas M, Lücke B, Berndt T, Birke P (1991) Appl Catal A 79(1):1–18
Frost J (1988) Nature 334(6183):577–580
Gao C, Xiao X, Mao D, Lu G (2013) Catal Sci Technol 3(4):1056–1062
Twigg MV, Spencer MS (2001) Appl Catal A 212:161–174
Avgouropoulos G, Ioannides T, Matralis H (2005) Appl Catal B 56(1–2):87–93
Guo XM, Mao DS, Lu GZ, Wang S, Wu GS (2010) J Catal 271(2):178–185
Melian-Cabrera I, Granados ML, Fierro JLG (2002) J Catal 210(2):273–284
Bahmani M, Farahani BV, Sahebdelfar S (2016) Appl Catal A 520:178–187
Schumann J, Eichelbaum M, Lunkenbein T, Thomas N, Galván MCÁ, Schlögl R, Behrens M (2015) ACS Catal 5(6):3260–3270
Li Z, Zheng HY, Xie KC (2008) Chin J Catal 29(5):431
Li W, Fan G, Yang L, Li F (2016) Catal Sci Technol 6(7):2337–2348
Perret N, Cárdenas-Lizana F, Keane MA (2011) Catal Commun 16(1):159–164
Zhu Y, Zhu Y, Ding G, Zhu S, Zheng H, Li Y (2013) Appl Catal A 468(12):296–304
Kusunoki Y, Miyazawa T, Kunimori K, Tomishige K (2005) Catal Commun 6(10):645–649
Nakagawa Y, Ning X, Amada Y, Tomishige K (2012) Appl Catal A 433–434(16):128–134
Shi Z (2016) Catal Sci Technol 6(10):3457–3467
Li T, Fu C, Qi J, Pan J, Chen S, Lin J (2013) React Kinet Mech Cat 109(1):117–131
Busca G (2014) Catal Today 226(1):2–13
Gao J, Jia C, Li J, Zhang M, Gu F, Xu G, Zhong Z, Su F (2013) J Energy Chem 22(6):919–927
Yang X, Xiang X, Chen H, Zheng H, Li Y-W, Zhu Y (2017) ChemCatChem 9:3023–3030
Yang X, Chen H, Meng Q, Zheng H, Zhu Y, Li Y (2017) Catal Sci Technol 7:5625–5634
Zhang B, Chen Y, Li J, Pippel E, Yang H, Gao Z, Qin Y (2015) ACS Catal 5:5567–5573
Zhang B, Zhu Y, Ding G, Zheng H, Li Y (2012) Appl Catal A 443:191–201
Asao N, Nogami T, Takahashi K, Yamamoto Y (2002) J Am Chem Soc 124(5):764–765
Acknowledgements
This work was supported by the technology institute of Shanghai Huayi (Group) Company, Jilin Province Science and Technology research plan (key scientific research project) (No. 20150204020GX).
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher’s Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Jiang, Y., Bao, Q., Gui, W. et al. A Highly Effective Cu/ZnO/Al2O3 Catalyst for Hydrogenation of Methyl Benzoate to Benzyl Alcohol in Methanol Solution. Catal Lett 149, 1359–1367 (2019). https://doi.org/10.1007/s10562-019-02721-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-019-02721-x