Highly Selective Hydrogenation of Cinnamaldehyde to Hydrocinnamaldehyde by Using Few Layer Graphene as a Catalyst Support
Main Article Content
Abstract
Few layer graphene (FLG) materials have been applied in different areas for over last decade thanks to their novel properties. In this work, FLG was produced from pencil lead by mechanical exfoliation method, this material was used as catalyst support for palladium (Pd) nanoparticles. Pd/FLG catalyst was characterised by several techniques including nitrogen adsorption - desorption isotherms (BET), scanning electron microscopy (SEM), transmission electron microscopy (TEM) and Raman spectrometry. The catalyst was tested for the selective hydrogenation of cinnamaldehyde (CAL), and the result showed a high selectivity to the C=C bond, over 94% of hydrocinnamaldehyde (HCAL) obtained at 80% of CAL conversion. The high selectivity to HCAL in this work is related to two different aspects, the first is the high graphitization degrees of FLG (Iᴅ/Iɢ = 5.7), the second is due to the size of Pd nanoparticles.
Keywords
FLG, Pd/FLG, Raman, SEM, TEM, Cinnamaldehyde hydrogenation
Article Details
References
[1] Feng Jiang, Jian Cai, Bing Liu, Yuebing Xu and Xiaohao Liu, “Particle Size Effects in the Selective Hydrogenation of Cinnamaldehyde over Supported Palladium Catalysts”, RSC Advances, Vol.6, (2016) p.75541-75551.
[2] T. Szumelda, A. Drelinkiewicz, R. Kosydar, J. Grugel, “Hydrogenation of cinnamaldehyde in the presence of Pd/AC catalysts prepared by the reverse “water-in-oil” microemulsion method”, Applied Catalysis A: General 487, (2014) p.1-5.
[3] B. Bond, Catalysis of Metals, Academic Press, London, 1962.
[4] Marjolein L. Toebes, T. Alexander Nijhuis, Jan Hajek, Johannes H. Bitter, A. Jos van Dillen,Dmitry Y. Murzin, Krijn P. de Jong, “Support effects in hydrogenation of cinnamaldehyde over carbon nanofiber-supported platinum catalysts: Kinetic modeling”, Chemical Engineering Science, Vol.60, (2005) p.5682-5695.
[5] Arie J. Plomp, Heli Vuori, A. Outi I. Krause, Krijn P. de Jong, Johannes H. Bitter, “Particle size effects for carbon nanofiber supported Pd and Pt catalysts for the selective hydrogenation of cinnamaldehyde”, Applied Catalysis A: General 351, (2008) p.9-15.
[6] Marjolein L. Toebes, Frans F. Prinsloo, A. Jos van Dillen, Johannes H. Bitter, and Krijn P. de Jong, “Influence of oxygen-containing surface groups on the activity and selectivity of carbon nanofiber-supported platinum catalysts in the hydrogenation of cinnamaldehyde”, Journal of Catalysis, Vol.214, (2003) p.78-87.
[7] A. Hammoudeh, S. Mahmoud, “Selective hydrogenation of cinnamaldehyde over Pd/SiO2 catalysts: selectivity promotion by alloyed Sn”, Journal of Molecular Catalysis A: Chemical 203, (2003) p.231-239.
[8] P. Gallezot, D. Richard, “Selective Hydrogenation of α,β-Unsaturated Aldehydes”, Catal. Rev.-Sci. Eng., Vol.40, (1998) p.81-126.
[9] Jieshan Qiu, Hongzhe Zhang, Xiuma Wang, Hongmei Han, Chanping Liang and Cun Li, “Selective hydrogenation of cinnamaldehyde over carbon nanotube supported Pd-Ru catalysts”, React. Kinet. Catal. Lett., Vol. 88, No. 2, (2006) p.269-275.
[10] Qiang Han, Yunfei Liu, Dong Wang, Fulong Yuan, Xiaoyu Niu and Yujun Zhu, “Effect of carbon nanosheets with different graphitization degrees as a support of noble metals on selective hydrogenation of cinnamaldehyde”, RSC Advances, Vol.6, (2016) p.9836-98364.
[11] Bao-Hui Zhao, Jian-Gang Chen, Xuan Liu, Zhong-Wen Liu, Zhengping Hao, Jianling Xiao, and Zhao-Tie Liu, “Selective Hydrogenation of Cinnamaldehyde over Pt and Pd Supported on Multiwalled Carbon Nanotubes in a CO2-Expanded Alcoholic Medium”, Ind. Eng. Chem. Res., Vol.51(34), (2012) p.11112-11121.
[12] Yuanuki Zhang, Shijian Liao, Yun Xu, Daorong Yu, “Catalytic selective hydrogenation of cinnamaldehyde to hydrocinnamaldehyde”, Applied Catalysis A: General 192, (2000) p.247-251.
[13] Masayuki Shirai, Tomonari Tanaka, Masahiko Arai, “Selective hydrogenation of α, β-unsaturated aldehyde to unsaturated alcohol with supported platinum catalysts at high pressures of hydrogen”, Journal of Molecular Catalysis A: Chemical 168, (2001) p.99-103.
[14] Jian Ru Gong, “Graphene - Synthesis, characterization, properties and applications”, Janzec Trndje 9, 51000 Rijeka, Croatia, 2011.
[15] I. Janowska, F. Vigneron, D. Begin, O. Ersen, P. Bernhardt, T. Romero, M.J. Ledoux, C. Pham-Huu, “Mechanical thinning to make few-layer graphene from pencil lead”, Carbon, Vol.50, (2012) p.3902-3916.
[16] Mustafa Lotya, Yenny Hernandez, Paul J. King, Roan J. Smith, Valerie Nicolosi, Lisa S. Karlsson, Fiona M. Blighe, Sukanta De, Zhiming Wang, I. T. McGovern, Georg S. Duesberg and Jonathan N. Coleman, “Liquid phase production of graphene by exfoliation of graphite in surfactant/water solutions”, J. Am. Chem. Soc, Vol.131, (2009) p.3611-3620.
[17] H.S.S. Ramakrishna Matte, K.S. Subrahmanyam and C. N. R. Rao, “Synthetic Aspects and Selected Properties of Graphene”, Nanomater. Nanotechnol. Vol.1, (2011) p.13-18.
[18] Yongchao Si and Edward T. Samulski, “Exfoliated Graphene Separated by Platinum Nanoparticles”, Chem. Mater, Vol.20, (2008) p.6792-6797.
[19] Dong Wang, Yujun Zhu, Chunjun Tian, Lei Wang, Wei Zhou, Yongqi Dong, Haijing Yan, and Honggang Fu, “Synergistic Effect of Tungsten Trioxide and Palladium for the Selective Hydrogenation of Cinnamaldehyde at the C=C bond”, ChemCatChem, Vol.8, (2016) p.1718-1726.
[2] T. Szumelda, A. Drelinkiewicz, R. Kosydar, J. Grugel, “Hydrogenation of cinnamaldehyde in the presence of Pd/AC catalysts prepared by the reverse “water-in-oil” microemulsion method”, Applied Catalysis A: General 487, (2014) p.1-5.
[3] B. Bond, Catalysis of Metals, Academic Press, London, 1962.
[4] Marjolein L. Toebes, T. Alexander Nijhuis, Jan Hajek, Johannes H. Bitter, A. Jos van Dillen,Dmitry Y. Murzin, Krijn P. de Jong, “Support effects in hydrogenation of cinnamaldehyde over carbon nanofiber-supported platinum catalysts: Kinetic modeling”, Chemical Engineering Science, Vol.60, (2005) p.5682-5695.
[5] Arie J. Plomp, Heli Vuori, A. Outi I. Krause, Krijn P. de Jong, Johannes H. Bitter, “Particle size effects for carbon nanofiber supported Pd and Pt catalysts for the selective hydrogenation of cinnamaldehyde”, Applied Catalysis A: General 351, (2008) p.9-15.
[6] Marjolein L. Toebes, Frans F. Prinsloo, A. Jos van Dillen, Johannes H. Bitter, and Krijn P. de Jong, “Influence of oxygen-containing surface groups on the activity and selectivity of carbon nanofiber-supported platinum catalysts in the hydrogenation of cinnamaldehyde”, Journal of Catalysis, Vol.214, (2003) p.78-87.
[7] A. Hammoudeh, S. Mahmoud, “Selective hydrogenation of cinnamaldehyde over Pd/SiO2 catalysts: selectivity promotion by alloyed Sn”, Journal of Molecular Catalysis A: Chemical 203, (2003) p.231-239.
[8] P. Gallezot, D. Richard, “Selective Hydrogenation of α,β-Unsaturated Aldehydes”, Catal. Rev.-Sci. Eng., Vol.40, (1998) p.81-126.
[9] Jieshan Qiu, Hongzhe Zhang, Xiuma Wang, Hongmei Han, Chanping Liang and Cun Li, “Selective hydrogenation of cinnamaldehyde over carbon nanotube supported Pd-Ru catalysts”, React. Kinet. Catal. Lett., Vol. 88, No. 2, (2006) p.269-275.
[10] Qiang Han, Yunfei Liu, Dong Wang, Fulong Yuan, Xiaoyu Niu and Yujun Zhu, “Effect of carbon nanosheets with different graphitization degrees as a support of noble metals on selective hydrogenation of cinnamaldehyde”, RSC Advances, Vol.6, (2016) p.9836-98364.
[11] Bao-Hui Zhao, Jian-Gang Chen, Xuan Liu, Zhong-Wen Liu, Zhengping Hao, Jianling Xiao, and Zhao-Tie Liu, “Selective Hydrogenation of Cinnamaldehyde over Pt and Pd Supported on Multiwalled Carbon Nanotubes in a CO2-Expanded Alcoholic Medium”, Ind. Eng. Chem. Res., Vol.51(34), (2012) p.11112-11121.
[12] Yuanuki Zhang, Shijian Liao, Yun Xu, Daorong Yu, “Catalytic selective hydrogenation of cinnamaldehyde to hydrocinnamaldehyde”, Applied Catalysis A: General 192, (2000) p.247-251.
[13] Masayuki Shirai, Tomonari Tanaka, Masahiko Arai, “Selective hydrogenation of α, β-unsaturated aldehyde to unsaturated alcohol with supported platinum catalysts at high pressures of hydrogen”, Journal of Molecular Catalysis A: Chemical 168, (2001) p.99-103.
[14] Jian Ru Gong, “Graphene - Synthesis, characterization, properties and applications”, Janzec Trndje 9, 51000 Rijeka, Croatia, 2011.
[15] I. Janowska, F. Vigneron, D. Begin, O. Ersen, P. Bernhardt, T. Romero, M.J. Ledoux, C. Pham-Huu, “Mechanical thinning to make few-layer graphene from pencil lead”, Carbon, Vol.50, (2012) p.3902-3916.
[16] Mustafa Lotya, Yenny Hernandez, Paul J. King, Roan J. Smith, Valerie Nicolosi, Lisa S. Karlsson, Fiona M. Blighe, Sukanta De, Zhiming Wang, I. T. McGovern, Georg S. Duesberg and Jonathan N. Coleman, “Liquid phase production of graphene by exfoliation of graphite in surfactant/water solutions”, J. Am. Chem. Soc, Vol.131, (2009) p.3611-3620.
[17] H.S.S. Ramakrishna Matte, K.S. Subrahmanyam and C. N. R. Rao, “Synthetic Aspects and Selected Properties of Graphene”, Nanomater. Nanotechnol. Vol.1, (2011) p.13-18.
[18] Yongchao Si and Edward T. Samulski, “Exfoliated Graphene Separated by Platinum Nanoparticles”, Chem. Mater, Vol.20, (2008) p.6792-6797.
[19] Dong Wang, Yujun Zhu, Chunjun Tian, Lei Wang, Wei Zhou, Yongqi Dong, Haijing Yan, and Honggang Fu, “Synergistic Effect of Tungsten Trioxide and Palladium for the Selective Hydrogenation of Cinnamaldehyde at the C=C bond”, ChemCatChem, Vol.8, (2016) p.1718-1726.