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Current Organic Synthesis

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ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

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Letter Article

Direct Gas-Phase Oxidation of Propylene to Acetone in the Presence of H2 and O2 over Au/TS-1 Catalyst

Author(s): Jinsong Fu, Xiaoming Zhang*, Wuyang Liang, Qian Lei, Bing Sun, Wujun He and Guowei Deng*

Volume 17, Issue 8, 2020

Page: [685 - 690] Pages: 6

DOI: 10.2174/1570179417666200615154837

Price: $65

Abstract

A novel process for the preparation of acetone is reported by gas-phase oxidation of propylene in the presence of H2 and O2 with Au supported TS-1 catalyst (Au/TS-1). By elevating the reaction temperature to 280 oC, Au/TS-1 catalyzes 11.6% propylene generating acetone with 70.6% selectivity, and 8.2% acetone in onepass yield. Acetone is originated from propylene oxide isomerization, which is mainly attributed to the surface of the Lewis base and high reaction temperature. Furthermore, small Au nanoparticle size promotes the reaction.

Keywords: Au/TS-1, propylene oxidation, acetone, cumene process, high reaction temperature, isomerization.

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[1]
Howard, W.L. Acetone, 5th ed; Wiley: New York, 2004.
[2]
Xu, S.; Zhang, J.; Chen, B.; Lei, Z. Process intensification on the selective catalytic oxidation of cumene with ionic liquids. Chem. Eng. Process., 2018, 130, 88-92.
[http://dx.doi.org/10.1016/j.cep.2018.06.002]
[3]
Das, S. Gupta, A.; Singh, D.; and Mahajani, S. La/Zn bimetallic oxide catalyst for epoxidation of styrene by cumene hydroperoxide: Kinetics and reaction engineering aspects. Ind. Eng. Chem. Res., 2019, 58, 7748-7460.
[http://dx.doi.org/10.1021/acs.iecr.8b05538]
[4]
Selvin, R.; Rajarajeswari, G.R.; Roselin, L.S.; Sadasivam, V.; Sivasankar, B.; Rengaraj, K. Catalytic decomposition of cumene hydroperoxide into phenol and acetone. Appl. Catal. A., 2001, 219, 125-129.
[http://dx.doi.org/10.1016/S0926-860X(01)00674-3]
[5]
Niwa Si, S.; Eswaramoorthy, M.; Nair, J.; Raj, A.; Itoh, N.; Shoji, H.; Namba, T.; Mizukami, F. A one-step conversion of benzene to phenol with a palladium membrane. Science, 2002, 295(5552), 105-107.
[http://dx.doi.org/10.1126/science.1066527] [PMID: 11778042]
[6]
Bellussi, G.; Perego, C. Industrial catalytic aspects of the synthesis of monomers for nylon production. CATTech, 2000, 4, 4-16.
[http://dx.doi.org/10.1023/A:1011905009608]
[7]
Li, Z.; Ma, W.; Zhong, Q. Insight into deactivation reasons for nanogold catalysts used in gas phase epoxidation of propylene. Catal. Lett., 2020.
[http://dx.doi.org/10.1007/s10562-020-03100-7]
[8]
Hong, Y.; Ke, L.; Li, Z.; Huang, J.; Zhan, G.; Zhou, Y.; Sun, D.; Zhang, J. Seed induced zeolitic TS 1 immobilized with bioinspired Au nanoparticles for propylene epoxidation with O2 and H2. Catal. Lett., 2020.
[http://dx.doi.org/10.1007/s10562-019-03086-x ]
[9]
Li, Z.; Ma, W.; Zhong, Q. Effect of core−shell support on Au/S-1/TS 1 for direct propylene epoxidation and design of catalyst with higher activity. Ind. Eng. Chem. Res., 2019, 58, 4010-4016.
[http://dx.doi.org/10.1021/acs.iecr.8b04662]
[10]
Lu, Z.; Liu, X.; Zhang, B.; Gan, Z.; Tang, S.; Ma, L.; Wu, T.; Nelson, G.; Qin, Y.; Turner, C.; Lei, Y. Structure and reactivity of single site Ti catalysts for propylene epoxidation. J. Catal., 2019, 377, 419-428.
[http://dx.doi.org/10.1016/j.jcat.2019.07.051]
[11]
Ren, Y.; Huang, J.; Lv, Q.; Xie, Y.; Lu, A.; Haruta, M. Dual-component gas pretreatment for Au/TS-1: Enhanced propylene epoxidation with oxygen and hydrogen; Appl. Catal. A., 2019, p. 584117172.
[http://dx.doi.org/10.1016/j.apcata.2019.117172]
[12]
Wang, G.; Cao, Y.; Zhang, Z.; Xu, J.; Lu, M.; Qian, G.; Duan, X.; Yuan, W.; Zhou, X. Surface engineering and kinetics behaviors of Au/uncalcined TS 1 catalysts for propylene epoxidation with H2 and O2. Ind. Eng. Chem. Res., 2019, 58, 17300-17307.
[http://dx.doi.org/10.1021/acs.iecr.9b03708]
[13]
Yuan, T.; Zhu, Q.; Gao, L.; Gao, J.; Ma, W. The nitriding of titanium silicate-1 and its effect on gas-phase epoxidation of propylene. J. Mater. Sci., 2020, 55, 3803-3811.
[http://dx.doi.org/10.1007/s10853-019-04166-4]
[14]
Li, Z.; Wang, Y.; Zhang, J.; Wang, D.; Ma, W. Better performance for gas-phase epoxidation of propylene using H2 and O2 at lower temperature over Au/TS-1 catalyst. Catal. Commun., 2017, 90, 87-90.
[http://dx.doi.org/10.1016/j.catcom.2016.12.002]
[15]
Feng, X.; Chen, D.; Zhou, X.G. Thermal stability of TPA template and size-dependent selectivity of uncalcined TS-1 supported Au catalyst for propene epoxidation with H2 and O2. RSC. Adv., 2016, 6, 44050.
[http://dx.doi.org/10.1039/C6RA05772A]
[16]
Feng, X.; Sheng, N.; Bin, Y.; Chen, X.; Chen, D.; Yang, C.; Zhou, X. Simultaneously enhanced stability and selectivity for propene epoxidation with H2 and O2 on Au catalysts supported on nano-crystalline mesoporous TS-1. ACS Catal., 2017, 7, 2668-2675.
[http://dx.doi.org/10.1021/acscatal.6b03498]
[17]
Liu, Y.; Zhang, X.; Suo, J. Gold supported on nitrogen-incorporated TS-1 for gas-phase epoxidation of propylene. Chin. J. Catal., 2013, 34, 336-340.
[http://dx.doi.org/10.1016/S1872-2067(11)60474-9]
[18]
Lee, W.; Akatay, A.M.C.; Stach, E.; Ribeiro, F.H.; Delgass, W.N. Reproducible preparation of Au/TS-1 with high reaction rate for gas phase epoxidation of propylene. J. Catal., 2012, 287, 178-189.
[http://dx.doi.org/10.1016/j.jcat.2011.12.019]
[19]
Qi, C.; Huang, J.; Bao, S.; Su, H.; Akita, T.; Haruta, M. Switching of reactions between hydrogenation and epoxidation of propene over Au/Ti-based oxides in the presence of H2 and O2. J. Catal., 2011, 281, 12-20.
[http://dx.doi.org/10.1016/j.jcat.2011.03.028]
[20]
Huang, J.; Lima, E.; Akita, T.; Guzmán, A.; Qi, C.; Takei, T.; Haruta, M. Propene epoxidation with O2 and H2: identification of the most active gold clusters. J. Catal., 2011, 278, 8-15.
[http://dx.doi.org/10.1016/j.jcat.2010.11.012]
[21]
Hayashi, T.; Tanaka, K.; Haruta, M. Selective vapor-phase epoxidation of propylene over Au/TiO2 catalysts in the presence of oxygen and hydrogen. J. Catal., 1998, 178, 556-575.
[http://dx.doi.org/10.1006/jcat.1998.2157]
[22]
Khomane, R.B.; Kulkarni, B.D.; Paraskar, A.; Sainkar, S.R. Synthesis, characterization and catalytic performance of titanium silicalite-1 prepared in micellar media. Mater. Chem. Phys., 2002, 76, 99-103.
[http://dx.doi.org/10.1016/S0254-0584(01)00507-7]
[23]
Lee, W.; Akatay, M.; Stach, E.; Ribeiro, F.; Delgass, W.N. Enhanced reaction rate for gas-phase epoxidation of propylene using H2 and O2 by Cs promotion of Au/TS-1. J. Catal., 2013, 308, 98-113.
[http://dx.doi.org/10.1016/j.jcat.2013.05.023]
[24]
Lee, W.; Akatay, M.; Stach, E.; Ribeiro, F.; Delgass, W.N. Gas-phase epoxidation of propylene in the presence of H2 and O2 over small gold ensembles in uncalcined TS-1. J. Catal., 2014, 313, 104-112.
[http://dx.doi.org/10.1016/j.jcat.2014.02.013]
[25]
Hong, Y.; Huang, J.; Zhan, G.; Li, Q. Biomass modified Au/TS-1 as highly efficient and stable nanocatalysts for propene epoxidation with O2 and H2. Ind. Eng. Chem. Res., 2019, 58, 21953-21960.
[http://dx.doi.org/10.1021/acs.iecr.9b04107]
[26]
Li, Z.; Gao, L.; Ma, W.; Zhong, Q. Higher gold atom efficiency over Au-Pd/TS-1 alloy catalysts for the direct propylene epoxidation with H2 and O2. Appl. Surf. Sci., 2019, 497143749
[http://dx.doi.org/10.1016/j.apsusc.2019.143749]
[27]
Li, Z.; Gao, L.; Zhu, X.; Ma, W.; Feng, X.; Zhong, Q. Synergistic enhancement over Au-Pd/TS-1 bimetallic catalysts for propylene epoxidation with H2 and O2. ChemCatChem, 2019, 11, 5116-5123.
[http://dx.doi.org/10.1002/cctc.201900845]
[28]
Lian, T.; Zeng, W.; Liu, H.; Yu, J.; Huang, J.; Wang, H.; Sun, D. The influence of active biomolecules in plant extracts on the performance of Au/TS-1 catalysts in propylene epoxidation. Eur. J. Inorg. Chem., 2019, 2853-2859.
[http://dx.doi.org/10.1002/ejic.201900397]
[29]
Figueiredoa, N.M.; Carvalho, N.J.M.; Cavaleiro, A. An XPS study of Au alloyed Al–O sputtered coatings. Appl. Surf. Sci., 2011, 257, 5793-5798.
[http://dx.doi.org/10.1016/j.apsusc.2011.01.104]
[30]
Ma, S.; Zhao, X.; Rodriguez, J.A.; Hrbek, J. STM and XPS Study of Growth of Ce on Au(111). J. Phys. Chem. C, 2007, 111, 3685-3691.
[http://dx.doi.org/10.1021/jp064366v]
[31]
Klyushin, A.Y.; Rocha, T.C.; Hävecker, M.; Knop-Gericke, A.; Schlögl, R. A near ambient pressure XPS study of Au oxidation. Phys. Chem. Chem. Phys., 2014, 16(17), 7881-7886.
[http://dx.doi.org/10.1039/c4cp00308j] [PMID: 24643747]
[32]
Gaudet, J.; Bando, K.; Song, Z.; Fujitani, T.; Zhang, W.; Su, D.; Oyama, S. Effect of gold oxidation state on the epoxidation and hydrogenation of propylene on Au/TS-1. J. Catal., 2011, 280, 40-49.
[http://dx.doi.org/10.1016/j.jcat.2011.03.001]
[33]
Peter, K.; Vollhardt, C. Organic chemistry: Structure and function, 6nd; Freeman, W.H., Ed.; New York, 2005.
[34]
Sinha, A.K.; Seelan, S.; Tsubota, S.; Haruta, M. Catalysis by gold nanoparticles: Epoxidation of propene. Top. Catal., 2004, 29, 95-102.
[http://dx.doi.org/10.1023/B:TOCA.0000029791.69935.53]
[35]
Lu, J.; Zhang, X.; Bravo-Suárez, J.; Bando, K.; Fujitani, T.; Oyama, S. Direct propylene epoxidation over barium-promoted Au/Ti-TUD catalysts with H2 and O2:Effect of Au particle size. J. Catal., 2007, 250, 350-359.
[http://dx.doi.org/10.1016/j.jcat.2007.06.006]
[36]
Yap, N.; Andres, R.P.; Delgass, W.N. Reactivity and stability of Au in and on TS-1 for epoxidation of propylene with H2 and O2. J. Catal., 2004, 226, 156-170.
[http://dx.doi.org/10.1016/j.jcat.2004.05.016]
[37]
Taylor, B.; Lauterbach, J.; Delgass, W.N. Gas-phase epoxidation of propylene over small gold ensembles on TS-1. Appl. Catal. A., 2005, 291, 188-198.
[http://dx.doi.org/10.1016/j.apcata.2005.02.039]
[38]
Hashmi, A.S.K.; Hutchings, G.J. Gold catalysis. Angew. Chem. Int. Ed. Engl., 2006, 45(47), 7896-7936.
[http://dx.doi.org/10.1002/anie.200602454] [PMID: 17131371]
[39]
Wells, D.H.; Delgass, W.N.; Thomson, K.T. Formation of hydrogen peroxide from H2 and O2 over a neutral gold trimer: a DFT study. J. Catal., 2004, 225, 69-77.
[http://dx.doi.org/10.1016/j.jcat.2004.03.028]
[40]
Li, Z.; Zhang, J.; Wang, D.; Ma, W.; Zhong, Q. Confirmation of gold active sites on titanium-silicalite-1-supported nano-gold catalysts for gas-phase epoxidation of propylene. J. Phys. Chem. C, 2017, 121, 25215-25222.
[http://dx.doi.org/10.1021/acs.jpcc.7b08293]

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