|
|
Pd/TiN nanocomposite catalysts for selective hydrogenation of phenol and its derivatives |
Hai-Feng Lia, Qin-Sheng Zhanga, Zeng-Bo Panga,b, Mi Tiana,b, Ping Gaoc, Lai-Lai Wanga |
a State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China;
b Graduate University of Chinese Academy of Sciences, Bejing 100039, China;
c State Key Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China |
|
|
Abstract Pd/TiN nanocomposite catalysts were fabricated for one-step selective hydrogenation of phenol to cyclohexanone successfully. High conversion of phenol (99%) and selectivity of cyclohexanone (98%) were obtained at 30℃ and 0.2 MPa H2 for 12 h in the mixed solvents of H2O and CH2Cl2. The Pd nanoparticles were stable in the reaction, and no aggregation was detected after four successive runs. The catalytic activity and selectivity depended on slightly the Pd particle sizes. The generality of the catalysts for this reaction was demonstrated by the selective hydrogenation of phenol derivatives, which showed that the catalyst was selective for the formation of cyclohexanone.
|
Received: 03 February 2016
Published: 01 April 2016
|
Fund:We are grateful to the financial supports granted by the National Natural Science Foundation of China ([9TD$DIF]No. 21174155). |
|
|
|
[1] |
S. Kuklin, A. Maximov, A. Zolotukhina, E. Karakhanov, New approach for highly selective hydrogenation of phenol to cyclohexanone:combination of rhodium nanoparticles and cyclodextrins, Catal. Commun. 73(2016) 63-68.
|
[2] |
H. Jiang, Z.Y. Qu, Y. Li, et al., One-step semi-continuous cyclohexanone production via hydrogenation of phenol in a submerged ceramic membrane reactor, Chem. Eng. J. 284(2016) 724-732.
|
[3] |
J.Z. Chen, W. Zhang, L.M. Chen, et al., Direct selective hydrogenation of phenol and derivatives over polyaniline-functionalized carbon-nanotube-supported palladium, Chempluschem 78(2013) 142-148.
|
[4] |
S.G. Shore, E. Ding, C. Park, M.A. Keane, The application of {(DMF)(10)Yb-2[TM(CN)(4)](3)}(infinity) (TM=Ni Pd) supported on silica to promote gas phase phenol hydrogenation, J. Mol. Catal. A:Chem. 212(2004) 291-300.
|
[5] |
Y. Wang, J.S. Zhang, X.C. Wang, M. Antonietti, H.R. Li, Boron- and fluorinecontaining mesoporous carbon nitride polymers:metal-free catalysts for cyclohexane oxidation, Angew. Chem. Int. Ed. 49(2010) 3356-3359.
|
[6] |
N.C. Nelson, J.S. Manzano, A.D. Sadow, S.H. Overbury, I.I. Sowing, Selective hydrogenation of phenol catalyzed by palladium on high-surface-area ceria at room temperature and ambient pressure, ACS Catal. 5(2015) 2051-2061.
|
[7] |
V.Z. Fridman, A.A. Davydov, Dehydrogenation of cyclohexanol on copper-containing catalysts I. The influence of the oxidation state of copper on the activity of copper sites, J. Catal. 195(2000) 20-30.
|
[8] |
F.W. Zhang, S. Chen, H. Li, X.M. Zhang, H.Q. Yang, Pd nanoparticles embedded in the outershell of a mesoporous core-shell catalyst for phenol hydrogenation in pure water, RSC Adv. 5(2015) 102811-102817.
|
[9] |
M. Chatterjee, H. Kawanami, M. Sato, et al., Hydrogenation of phenol in supercritical carbon dioxide catalyzed by palladium supported on Al-MCM-41:a facile route for one-pot cyclohexanone formation, Adv. Synth. Catal. 351(2009) 1912-1924.
|
[10] |
I.E. Ertas, M. Gulcan, A. Bulut, M. Yurderi, M. Zahmakiran, Rhodium nanoparticles stabilized by sulfonic acid functionalized metal-organic framework for the selective hydrogenation of phenol to cyclohexanone, J. Mol. Catal. A:Chem. 410(2015) 209-220.
|
[11] |
S.G. Shore, E.R. Ding, C. Park, M.A. Keane, Vapor phase hydrogenation of phenol over silica supported Pd and Pd-Yb catalysts, Catal. Commun. 3(2002) 77-84.
|
[12] |
Y.Z. Xiang, L.N. Kong, C.S. Lu, L. Ma, X.N. Li, Lanthanum-promoted Pd/Al2O3 catalysts for liquid phase in situ hydrogenation of phenol to cyclohexanone, React. Kinet. Mech. Cat. 100(2010) 227-235.
|
[13] |
S. Scire, S. Minico, C. Crisafulli, Selective hydrogenation of phenol to cyclohexanone over supported Pd and Pd-Ca catalysts:an investigation on the influence of different supports and Pd precursors, Appl. Catal. A:Gen. 235(2002) 21-31.
|
[14] |
Y.Z. Chen, C.W. Liaw, L.I. Lee, Selective hydrogenation of phenol to cyclohexanone over palladium supported on calcined Mg/Al hydrotalcite, Appl. Catal. A:Gen. 177(1999) 1-8.
|
[15] |
G. Neri, A.M. Visco, A. Donato, et al., Hydrogenation of phenol to cyclohexanone over palladium and alkali-doped palladium catalysts, Appl. Catal. A:Gen. 110(1994) 49-59.
|
[16] |
Y. Wang, J. Yao, H.R. Li, D.S. Su, M. Antonietti, Highly selective hydrogenation of phenol and derivatives over a Pd@carbon nitride catalyst in aqueous media, J. Am. Chem. Soc. 133(2011) 2362-2365.
|
[17] |
H.Z. Liu, T. Jiang, B.X. Han, S.G. Liang, Y.X. Zhou, Selective phenol hydrogenation to cyclohexanone over a dual supported Pd-lewis acid catalyst, Science 326(2009) 1250-1252.
|
[18] |
C.V. Rode, U.D. Joshi, O. Sato, M. Shirai, Catalytic ring hydrogenation of phenol under supercritical carbon dioxide, Chem. Commun. (2003) 1960-1961.
|
[19] |
H. Liu, T. Jiang, B. Han, S. Liang, Y. Zhou, Selective phenol hydrogenation to cyclohexanone over a dual supported Pd-Lewis acid catalyst, Science 326(2009) 1250-1252.
|
[20] |
Y. Wang, J. Yao, H. Li, D. Su, M. Antonietti, Highly selective hydrogenation of phenol and derivatives over a Pd@carbon nitride catalyst in aqueous media, J. Am. Chem. Soc. 133(2011) 2362-2365.
|
[21] |
D.V. Esposito, S.T. Hunt, Y.C. Kimmel, J.G.G. Chen, A new class of electrocatalysts for hydrogen production from water electrolysis:metal monolayers supported on low-cost transition metal carbides, J. Am. Chem. Soc. 134(2012) 3025-3033.
|
[22] |
X.H. Li, M. Antonietti, Metal nanoparticles at mesoporous N-doped carbons and carbon nitrides:functional Mott-Schottky heterojunctions for catalysis, Chem. Soc. Rev. 42(2013) 6593-6604.
|
[23] |
H. Hammerle, K. Kobuch, K. Kohler, et al., Biostability of micro-photodiode arrays for subretinal implantation, Biomaterials 23(2002) 797-804.
|
[24] |
M. Marlo, V. Milman, Density-functional study of bulk and surface properties of titanium nitride using different exchange-correlation functionals, Phys. Rev. B 62(2000) 2899-2907.
|
[25] |
V. Molinari, C. Giordano, M. Antonietti, D. Esposito, Titanium nitride-nickel nanocomposite as heterogeneous catalyst for the hydrogenolysis of aryl ethers, J. Am. Chem. Soc. 136(2014) 1758-1761.
|
[26] |
J.F. Zhu, G.H. Tao, H.Y. Liu, et al., Aqueous-phase selective hydrogenation of phenol to cyclohexanone over soluble Pd nanoparticles, Green Chem. 16(2014) 2664-2669.
|
[27] |
D. Shuai, D.C. McCalman, J.K. Choe, et al., Structure sensitivity study of waterborne contaminant hydrogenation using shape- and size-controlled Pd nanoparticles, ACS Catal. 3(2013) 453-463.
|
[28] |
M. Crespo-Quesada, A. Yarulin, M. Jin, Y. Xia, L. Kiwi-Minsker, Structure sensitivity of alkynol hydrogenation on shape- and size-controlled palladium nanocrystals:which sites are most active and selective? J. Am. Chem. Soc. 133(2011) 12787-12794.
|
[29] |
A. Chen, G. Zhao, J. Chen, L. Chen, Y. Yu, Selective hydrogenation of phenol and derivatives over an ionic liquid-like copolymer stabilized palladium catalyst in aqueous media, RSC Adv. 3(2013) 4171-4175.
|
|
|
|