The cooperation effect of Ni and Pt in the hydrogenation of acetic acid

Abstract

The catalytic hydrogenation of carboxylic acid to alcohols is one of the important strategies for the conversion of biomass. Herein, a series of Ni-doped PtSn catalysts were prepared, characterized and studied in the hydrogenation of acetic acid. The Ni dopant has a strong interaction with Pt, which promotes the hydrogen adsorption, providing an activated hydrogen-rich environment for the hydrogenation. Meanwhile, the presence of Ni also improves the Pt dispersion, giving more accessible active sites for hydrogen activation. The cooperation of Pt and Ni significantly promotes the catalytic activity of the hydrogenation of acetic acid to ethanol. As a result, the catalyst with 0.1% Ni exhibits the best reaction activity, and its space time yield is twice as that of the PtSn/SiO₂ catalyst. It provides a meaningful instruction on the catalyst design for the carboxylic acid hydrogenation.

Graphical abstract

Keywords

acetic acid / ethanol / hydrogenation / Pt / Ni / cooperation effect

References

[1] Goldemberg J. Ethanol for a sustainable energy future. Science, 2007, 315(5813): 808–810

[2] Pestman R, Koster R M, Boellaard E, van der Kraan A M, Ponec V. Identification of the active sites in the selective hydrogenation of acetic acid to acetaldehyde on iron oxide catalysts. Journal of Catalysis, 1998, 174(2): 142–152

[3] Manyar H G, Paun C, Pilus R, Rooney D W, Thompson J M, Hardacre C. Highly selective and efficient hydrogenation of carboxylic acids to alcohols using titania supported Pt catalysts. Chemical Communications, 2010, 46(34): 6279–6281

[4] Li X H, Antonietti M. Metal nanoparticles at mesoporous N-doped carbons and carbon nitrides: functional Mott-Schottky heterojunctions for catalysis. Chemical Society Reviews, 2013, 42(16): 6593–6604

[5] Dhakshinamoorthy A, Garcia H. Catalysis by metal nanoparticles embedded on metal-organic frameworks. Chemical Society Reviews, 2012, 41(15): 5262–5284

[6] Yan H, Cheng H, Yi H, Lin Y, Yao T, Wang C, Li J, Wei S, Lu J. Single-atom Pd₁/graphene catalyst achieved by atomic layer deposition: remarkable performance in selective hydrogenation of 1,3-butadiene. Journal of the American Chemical Society, 2015, 137(33): 10484–10487

[7] Vile G, Albani D, Nachtegaal M, Chen Z, Dontsova D, Antonietti M, Lopez N, Perez-Ramirez J. A stable single-site palladium catalyst for hydrogenations. Angewandte Chemie International Edition, 2015, 54(38): 11265–11269

[8] Lin J, Qiao B, Li N, Li L, Sun X, Liu J, Wang X, Zhang T. Little do more: a highly effective Pt₁/FeO_x single-atom catalyst for the reduction of NO by H₂. Chemical Communications, 2015, 51(37): 7911–7914

[9] Li W, Ye L, Chen J, Duan X, Lin H, Yuan Y. FeSBA-15-supported ruthenium catalyst for the selective hydrogenolysis of carboxylic acids to alcoholic chemicals. Catalysis Today, 2015, 251: 53–59

[10] Pallassana V, Neurock M. Reaction paths in the hydrogenolysis of acetic acid to ethanol over Pd(111), Re(0001), and PdRe alloys. Journal of Catalysis, 2002, 209(2): 289–305

[11] Rachmady W, Vannice M A. Acetic acid reduction by H₂ on bimetallic Pt-Fe catalysts. Journal of Catalysis, 2002, 209(1): 87–98

[12] Zhang S, Duan X, Ye L, Lin H, Xie Z, Yuan Y. Production of ethanol by gas phase hydrogenation of acetic acid over carbon nanotube-supported Pt-Sn nanoparticles. Catalysis Today, 2013, 215: 260–266

[13] Zhang K, Zhang H T, Ma H F, Ying W Y, Fang D Y. Effect of Sn addition in gas phase hydrogenation of acetic acid on alumina supported PtSn catalysts. Catalysis Letters, 2014, 144(4): 691–701

[14] Xu G, Zhang J, Wang S, Zhao Y, Ma X. A well fabricated PtSn/SiO₂ catalyst with enhanced synergy between Pt and Sn for acetic acid hydrogenation to ethanol. RSC Advances, 2016, 6(56): 51005–51013

[15] Zhou J H, Zhao Y J, Zhang J, Wang Y, Gutierrez O Y, Wang S N, Li Z X, Jin P, Wang S P, Ma X B, . A nitrogen-doped PtSn nanocatalyst supported on hollow silica spheres for acetic acid hydrogenation. Chemical Communications, 2018, 54(64): 8818–8821

[16] Xu G, Zhang J, Wang S, Zhao Y, Ma X. Effect of thermal pretreatment on the surface structure of PtSn/SiO₂ catalyst and its performance in acetic acid hydrogenation. Frontiers of Chemical Science and Engineering, 2016, 10(3): 417–424

[17] Rachmady W, Vannice M A. Acetic acid reduction to acetaldehyde over iron catalysts I. Kinetic behavior. Journal of Catalysis, 2002, 208(1): 158–169

[18] Zhou M, Zhang H, Ma H, Ying W. The catalytic properties of K modified PtSn/Al₂O₃ catalyst for acetic acid hydrogenation to ethanol. Fuel Processing Technology, 2016, 144: 115–123

[19] Siri G J, Bertolini G R, Casella M L, Ferretti O A. PtSn/γ-Al₂O₃ isobutane dehydrogenation catalysts: the effect of alkaline metals addition. Materials Letters, 2005, 59(18): 2319–2324

[20] Wang Z, Li G, Liu X, Huang Y, Wang A, Chu W, Wang X, Li N. Aqueous phase hydrogenation of acetic acid to ethanol over Ir-MoO_x/SiO₂ catalyst. Catalysis Communications, 2014, 43: 38–41

[21] Kim S M, Abdala P M, Margossian T, Hosseini D, Foppa L, Armutlulu A, van Beek W, Comas-Vives A, Coperet C, Mueller C. Cooperativity and dynamics increase the performance of NiFe dry reforming catalysts. Journal of the American Chemical Society, 2017, 139(5): 1937–1949

[22] Han Q, Rehman M U, Wang J, Rykov A, Gutierrez O Y, Zhao Y, Wang S, Ma X, Lercher J A. The synergistic effect between Ni sites and Ni-Fe alloy sites on hydrodeoxygenation of lignin-derived phenols. Applied Catalysis B: Environmental, 2019, 253: 348–358

[23] Ruan Y, Zhao Y, Lu Y, Guo D, Zhao Y, Wang S, Ma X. Mesoporous LaAl_0.25Ni_0.75O₃ perovskite catalyst using SBA-15 as templating agent for methane dry reforming. Microporous and Mesoporous Materials, 2020, 303: 1–9

[24] Lu Y, Guo D, Ruan Y, Zhao Y, Wang S, Ma X. Facile one-pot synthesis of Ni@HSS as a novel yolk-shell structure catalyst for dry reforming of methane. Journal of CO2 Utilization, 2018, 24: 190–199

[25] Xiang M, Zou J, Li D, Li W, Sun Y, She X. Nickel and potassium co-modified β-Mo₂C catalyst for CO conversion. Journal of Natural Gas Chemistry, 2009, 18(2): 183–186

[26] Xiang M, Li D, Li W, Zhong B, Sun Y. Potassium and nickel doped β-Mo₂C catalysts for mixed alcohols synthesis via syngas. Catalysis Communications, 2007, 8(3): 513–518

[27] Han S, Liu Y, Li J, Li R, Yuan F, Zhu Y. Improvement effect of Ni to Pd-Ni/SBA-15 catalyst for selective hydrogenation of cinnamaldehyde to hydrocinnamaldehyde. Catalysts, 2018, 8(5): 200

[28] Zhang J, Kong L, Chen Y, Huang H, Zhang H, Yao Y, Xu Y, Xu Y, Wang S, Ma X, Zhao Y. Enhanced synergy between Cu⁰ and Cu⁺ on nickel doped copper catalyst for gaseous acetic acid hydrogenation. Frontiers of Chemical Science and Engineering, 2021, 15(3): 666–678

[29] Wang Q Q, Qu J, Liu Y, Gui C X, Hao S M, Yu Y, Yu Z Z. Growth of nickel silicate nanoplates on reduced graphene oxide as layered nanocomposites for highly reversible lithium storage. Nanoscale, 2015, 7(40): 16805–16811

[30] Schreier M, Regalbuto J R. A fundamental study of Pt tetraammine impregnation of silica 1. The electrostatic nature of platinum adsorption. Journal of Catalysis, 2004, 225(1): 190–202

[31] Miller J T, Schreier M, Kropf A J, Regalbuto J R. A fundamental study of platinum tetraammine impregnation of silica 2. The effect of method of preparation, loading, and calcination temperature on (reduced) particle size. Journal of Catalysis, 2004, 225(1): 203–212

[32] Boonpai S, Wannakao S, Suriye K, Marquez V, Panpranot J, Jongsomjit B, Praserthdam P, Bell A T. Influence of surface Sn species and hydrogen interactions on the OH group formation over spherical silica-supported tin oxide catalysts. Reaction Chemistry & Engineering, 2020, 5(9): 1814–1823

[33] Kamiuchi N, Taguchi K, Matsui T, Kikuchi R, Eguchi K. Sintering and redispersion of platinum catalysts supported on tin oxide. Applied Catalysis B: Environmental, 2009, 89(1–2): 65–72

[34] Rynkowski J, Rajski D, Szyszka I, Grzechowiak J R. Effect of platinum on the hydrogenation activity of nickel catalysts. Catalysis Today, 2004, 90(1–2): 159–166

[35] Zhang C, Lv W, Yang Q, Liu Y. Graphene supported nano particles of Pt-Ni for CO oxidation. Applied Surface Science, 2012, 258(20): 7795–7800

[36] Mahoney E G, Pusel J M, Stagg-Williams S M, Faraji S. The effects of Pt addition to supported Ni catalysts on dry (CO₂) reforming of methane to syngas. Journal of CO₂ Utilization, 2014, 6: 40–44

[37] Taniya K, Jinno H, Kishida M, Ichihashi Y, Nishiyama S. Preparation of Sn-modified silica-coated Pt catalysts: a new Pt-Sn bimetallic model catalyst for selective hydrogenation of crotonaldehyde. Journal of Catalysis, 2012, 288: 84–91

[38] Alcala R, Mavrikakis M, Dumesic J A. DFT studies for cleavage of C–C and C–O bonds in surface species derived from ethanol on Pt(111). Journal of Catalysis, 2003, 218(1): 178–190

[39] Takeda Y, Nakagawa Y, Tomishige K. Selective hydrogenation of higher saturated carboxylic acids to alcohols using a ReO_x-Pd/SiO₂ catalyst. Catalysis Science & Technology, 2012, 2(11): 2221–2223

[40] Zhao X, Wu K, Liao W, Wang Y, Hou X, Jin M, Suo Z, Ge H. Improvement of low temperature activity and stability of Ni catalysts with addition of Pt for hydrogen production via steam reforming of ethylene glycol. Green Energy & Environment, 2019, 4(3): 300–310

[41] Pudukudy M, Yaakob Z, Jia Q, Takriff M S. Catalytic decomposition of undiluted methane into hydrogen and carbon nanotubes over Pt promoted Ni/CeO₂ catalysts. New Journal of Chemistry, 2018, 42(18): 14843–14856

[42] Abbas S A, Kim S H, Iqbal M I, Muhammad S, Yoon W S, Jung K D. Synergistic effect of nano-Pt and Ni spine for HER in alkaline solution: hydrogen spillover from nano-Pt to Ni spine. Scientific Reports, 2018, 8(1): 8

[43] Tellez-Romero J G, Cuevas-Garcia R, Ramirez J, Castillo-Villalon P, Contreras-Barbara R, Salcedo-Luna M C, Puente-Lee R I. Simultaneous naphthalene and thiophene hydrogenation over Ni(X)-Pt/HMOR catalysts. Catalysis Today, 2015, 250: 12–20

[44] Wang X F, Liang X H, Geng P, Li Q B. Recent advances in selective hydrogenation of cinnamaldehyde over supported metal-based catalysts. ACS Catalysis, 2020, 10(4): 2395–2412

[45] Yang X F, Wang A Q, Qiao B T, Li J, Liu J Y, Zhang T. Single-atom catalysts: a new frontier in heterogeneous catalysis. Accounts of Chemical Research, 2013, 46(8): 1740–1748

[46] Zhang J, Zheng C, Zhang M, Qiu Y, Xu Q, Cheong W C, Chen W, Zheng L, Gu L, Hu Z, . Controlling N-doping type in carbon to boost single-atom site Cu catalyzed transfer hydrogenation of quinoline. Nano Research, 2020, 13(11): 3082–3087

[47] Zhang Z D, Zhou M, Chen Y J, Liu S J, Wang H F, Zhang J, Ji S F, Wang D S, Li Y D. Pd single-atom monolithic catalyst: functional 3D structure and unique chemical selectivity in hydrogenation reaction. Science China Materials, 2021, 64, 1919–1929

[48] Ren Z, Younis M N, Li C, Li Z, Yang X, Wang G. Highly active Ce, Y, La-modified Cu/SiO₂ catalysts for hydrogenation of methyl acetate to ethanol. RSC Advances, 2020, 10(10): 5590–5603

[49] Dong X, Lei J, Chen Y, Jiang H, Zhang M. Selective hydrogenation of acetic acid to ethanol on Cu-In catalyst supported by SBA-15. Applied Catalysis B: Environmental, 2019, 244: 448–458

[50] Beerthuis R, de Rijk J W, Deeley J M S, Sunley G J, de Jong K P, de Jongh P E. Particle size effects in copper-catalyzed hydrogenation of ethyl acetate. Journal of Catalysis, 2020, 388: 30–37

RIGHTS & PERMISSIONS

Higher Education Press