Abstract
CuNiAl hydrotalcites supported BiOCl were prepared by one-step synthesis for the selective oxidation of glycerol to glyceraldehyde with H2O2 as oxidant. The prepared catalysts were found to be efficient due to the synergetic catalysis of surface oxygen vacancies, active Cu2+ ions in the HT-lattice and abundant surface –OH groups of catalysts. The optimal glycerol conversion could reach 75.4% with 82.4% of the selectivity to glyceraldehyde. Moreover, the catalyst could be reused at least 6 times, and a possible reaction mechanism was also proposed.
Graphical Abstract
Inexpensive and environmentally friendly BiOCl/CuNiAl-HTs were synthesized by one-step for the highly selective oxidation of glycerol to glyceraldehyde. The glycerol conversion could reach 75.4% with 82.4% selectivity to GLAD. Such a highly efficient catalytic performance could be attributed to the synergistic effect of oxygen vacancies and the coordination of glycerol on Bi3+ in the supported BiOCl catalyst.
Similar content being viewed by others
References
Zhou CHC, Beltramini JN, Fan YX, Lu GQM (2008) Chemoselective catalytic conversion of glycerol as a biorenewable source to valuable commodity chemicals. Chem Soc Rev 37:527–549
Behr A, Eilting J, Irawadi K, Leschinski J, Lindner F (2008) Improved utilisation of renewable resources: new important derivatives of glycerol. Green Chem 10:13–30
Sun D, Yamada Y, Sato S, Uedab W (2017) Glycerol as a potential renewable raw material for acrylic acid production. Green Chem 19:3186–3213
Davis SE, Ide MS, Davis RJ (2013) Selective oxidation of alcohols and aldehydes over supported metal nanoparticles. Green Chem 15:17–45
Cespi D, Passarini F, Mastragostino G, Vassura I, Larocca S, Iaconi A, Chieregato A, Duboise JL, Cavani F (2015) Glycerol as feedstock in the synthesis of chemicals: a life cycle analysis for acrolein production. Green Chem 17:343–355
Pagliaro M, Ciriminna R, Kimura H, Rossi M, Pina CD (2007) From glycerol to value-added products. Angew Chem Int Ed 46:4434–4440
Ren Y, Chen Z, Cai Y, Lin J (2011) Electrosynthesis of glyceraldehyde by cyclic nano-MnO2/Mn2+ in bipolar membrane-equipped electrolytic cell. Electrochem Commun 13:1317–1319
Pembere AM, Luo Z (2017) Jones oxidation of glycerol catalysed by small gold clusters. Phys Chem Chem Phys 19:6620–6625
Bianchi CL, Canton P, Dimitratos N, Porta F, Prati L (2005) Selective oxidation of glycerol with oxygen using mono and bimetallic catalysts based on Au, Pd and Pt metals. Catal Today 102:203–212
Fordham P, Besson M, Gallezot P (1995) Selective catalytic oxidation of glyceric acid to tartronic and hydroxypyruvic acids. Appl Catal 133:L179–L184
Kwon Y, Schouten KJP, Koper MTM (2011) Mechanism of the catalytic oxidation of glycerol on polycrystalline gold and platinum electrodes. ChemCatChem 3:1176–1185
Zalineeva A, Serov A, Padilla M, Martinez U, Artyushkova K, Baranton S, Coutanceau C, Atanassov PB (2014) Self-supported PdxBi catalysts for the electrooxidation of glycerol in alkaline media. J Am Chem Soc 136:3937–3945
Garcia AC, Birdja YY, Tremiliosi-Filho G, Koper MTM (2017) Glycerol electro-oxidation on bismuth-modified platinum single crystals. J Catal 346:117–124
Chornaja S, Sproge E, Dubencovs K, Kulikova L, Serga V, Cvetkovs A, Kampars V (2014) Kampars. Selective oxidation of glycerol to glyceraldehydes over novel monometallic platinum catalysts. Key Eng Mat 604:139–141
Dai X, Cui X, Yuan H, Deng Y, Shi F (2015) Cooperative transformation of nitroarenes and biomass-based alcohols catalyzed by CuNiAlOx. RSC Adv 5:7970–7975
Scholz D, Aellig C, Mondelli C, Ramrez J (2015) Continuous transfer hydrogenation of sugars to alditols with bioderived donors over Cu–Ni–Al catalysts. ChemCatChem 7:1551–1558
Zhao L, Li X, Zhao J (2013) Correlation of structural and chemical characteristics with catalytic performance of hydrotalcite-based CuNiAl mixed oxides for SO2 abatement. Chem Eng J 223:164–171
Wu GD, Wang XL, Huang YA, Liu XF, Zhang F, Ding KQ, Yang XL (2013) Selective oxidation of glycerol with O2 catalyzed by low-cost CuNiAl hydrotalcites. J Mol Catal A 379:185–191
Wang XL, Wu GD, Liu XF, Zhang CF, Lin QB (2016) Selective oxidation of glycerol with O2 catalyzed by LDH hosted transition metal complexes. Catal Lett 146:620–628
Zhou S, Qian ZhY, Sun T, Xu JG, Xia ChH (2011) Catalytic wet peroxide oxidation of phenol over Cu–Ni–Al hydrotalcite. Appl Clay Sci 53:627–633
Dubey A, Rives V, Kannan S (2002) Catalytic hydroxylation of phenol over ternary hydrotalcites containing Cu, Ni and Al. J Mol Catal A 181:151–161
Li H, Qin F, Yang Z, Cui X, Wang J, Zhang L (2017) New reaction pathway induced by plasmon for selective benzyl alcohol oxidation on BiOCl possessing oxygen vacancies. J Am Chem Soc 139:3513–3521
Kwon Y, Birdja Y, Spanos I, Rodriguez P, Koper MTM (2012) Highly selective electro-oxidation of glycerol to dihydroxyacetone on platinum in the presence of bismuth. ACS Catal 2:759–764
Ning X, Li Y, Yu H, Peng F, Wang H, Yang Y (2016) Promoting role of bismuth and antimony on Pt catalysts for the selective oxidation of glycerol to dihydroxyacetone. J Catal 335:95–104
Li ZJ, Qu Y, Hu K, Humayun M, Chen SY, Jing LQ (2017) Improved photoelectrocatalytic activities of BiOCl with high stability for water oxidation and MO degradation by coupling RGO and modifying phosphate groups to prolong carrier lifetime. Appl catal B 203:355–362
Cavani F, Trifiro F, Vaccari A (1991) Hydrotalcite-type anionic clays: preparation, properties and applications. Catal Today 11:173–301
Labajos FM, Rives V, Ulibarri MA (1992) Effect of hydrothermal and thermal treatments on the physicochemical properties of Mg-Al hydrotalcite-like materials. J Mater Sci 27:1546–1552
Huang D, Ma J, Yu L, Wu D, Wang K, Yang M, Papoulis D, Komarneni S (2015) AgCl and BiOCl composited with NiFe-LDH for enhanced photo-degradation of Rhodamine B. Sep Purif Technol 156:789–794
Guo N, Liang Y, Lan S, Liu L, Ji G, Gan S, Zou H, Xu X (2014) Uniform TiO2–SiO2 hollow nanospheres: synthesis, characterization and enhanced adsorption–photodegradation of azo dyes and phenol. Appl Surf Sci 305:562–574
Zhao K, Zhang LZ, Wang JJ, Li QX, He WW, Yin JJ (2013) Surface structure-dependent molecular oxygen activation of BiOCl single-crystalline nanosheets. J Am Chem Soc 135:15750–15753
Sá J, Aguera CA, Gross S (2009) Photocatalytic nitrate reduction over metal modified TiO2. Appl Catal B 85:192–200
Wang H, Xiang X, Li F, Evans DG, Duan X (2009) Investigation of the structure and surface characteristics of Cu–Ni–M(III) mixed oxides (M = Al, Cr and In) prepared from layered double hydroxide precursors. Appl Surf Sci 255:6945–6952
Liang SJ, Wen LR, Lin S, Bi JH, Feng PY, Fu XZ, Wu L (2014) Monolayer HNb3O8 for selective photocatalytic oxidation of benzylic alcohols with visible light response. Angew Chem Int Ed 53:2951–2955
Acknowledgements
The authors acknowledge the financial supports from National Natural Science Foundation of China 21203093, Natural Science Foundation of Jiangsu Province BK20141388 and BK20161481, Research Joint Research Project of Jiangsu Province BY2016008-03, Key Research and Development Program of Jiangsu Province BE2018718, and College Students Practice Innovation Training Program of Nanjing Institute of Technology TP20161201 and TZ20170023.
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest
All authors declare no conflicts of interest.
Additional information
Publisher’s Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Wang, X., Wu, G., Zhang, X. et al. Selective Oxidation of Glycerol to Glyceraldehyde with H2O2 Catalyzed by CuNiAl Hydrotalcites Supported BiOCl in Neutral Media. Catal Lett 149, 1046–1056 (2019). https://doi.org/10.1007/s10562-019-02689-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-019-02689-8