메뉴 건너뛰기




Volumn 119, Issue 4, 2015, Pages 1809-1817

Mechanism of 2-ethylhexenal hydrogenation on Pd(111): A density functional study

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION; DENSITY FUNCTIONAL THEORY; HYDROGENATION; ISOMERS; SURFACE REACTIONS;

EID: 84949117779     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp508644v     Document Type: Article
Times cited : (3)

References (51)
  • 1
    • 79951495646 scopus 로고    scopus 로고
    • Hydrogenation of 2-Ethylhexenal Using Thermoregulated Phase-Transfer Catalyst for Production of 2-Ethylhexanol
    • Liu, S.; Xie, C.; Yu, S.; Liu, F.; Song, Z. Hydrogenation of 2-Ethylhexenal Using Thermoregulated Phase-Transfer Catalyst for Production of 2-Ethylhexanol. Ind. Eng. Chem. Res. 2010, 50, 2478-2481.
    • (2010) Ind. Eng. Chem. Res. , vol.50 , pp. 2478-2481
    • Liu, S.1    Xie, C.2    Yu, S.3    Liu, F.4    Song, Z.5
  • 2
    • 0038179637 scopus 로고    scopus 로고
    • Esterification of Phthalic Anhydride with 1-Butanol and 2-Ethylhexanol Catalyzed by Heteropolyacids
    • Arabi, M.; Amini, M. M.; Abedini, M.; Nemati, A.; Alizadeh, M. Esterification of Phthalic Anhydride with 1-Butanol and 2-Ethylhexanol Catalyzed by Heteropolyacids. J. Mol. Catal. A: Chem. 2003, 200, 105-110.
    • (2003) J. Mol. Catal. A: Chem. , vol.200 , pp. 105-110
    • Arabi, M.1    Amini, M.M.2    Abedini, M.3    Nemati, A.4    Alizadeh, M.5
  • 3
    • 0032022421 scopus 로고    scopus 로고
    • Kinetics of the Esterification of Phthalic Anhydride with 2-Ethylhexanol: Part IV: Non-Catalytic Process. Final Kinetic Comparison of the Catalysts
    • Skrzypek, J.; Zbigniew Sadlowski, J.; Lachowska, M.; Nowak, P. Kinetics of the Esterification of Phthalic Anhydride with 2-Ethylhexanol: Part IV: Non-Catalytic Process. Final Kinetic Comparison of the Catalysts. Chem. Eng. Process 1998, 37, 163-167.
    • (1998) Chem. Eng. Process , vol.37 , pp. 163-167
    • Skrzypek, J.1    Zbigniew Sadlowski, J.2    Lachowska, M.3    Nowak, P.4
  • 4
    • 0037400425 scopus 로고    scopus 로고
    • Cetane Numbers of Branched and Straight-Chain Fatty Esters Determined in an Ignition Quality TesterWhite star
    • Knothe, G.; Matheaus, A. C.; Ryan Iii, T. W. Cetane Numbers of Branched and Straight-Chain Fatty Esters Determined in an Ignition Quality TesterWhite star. Fuel 2003, 82, 971-975.
    • (2003) Fuel , vol.82 , pp. 971-975
    • Knothe, G.1    Matheaus, A.C.2    Ryan, T.W.3
  • 5
    • 31544443553 scopus 로고    scopus 로고
    • Solid Acid Catalysts for Biodiesel Production - Towards Sustainable Energy
    • Kiss, A. A.; Dimian, A. C.; Rothenberg, G. Solid Acid Catalysts for Biodiesel Production - Towards Sustainable Energy. Adv. Synth. Catal. 2006, 348, 75-81.
    • (2006) Adv. Synth. Catal. , vol.348 , pp. 75-81
    • Kiss, A.A.1    Dimian, A.C.2    Rothenberg, G.3
  • 7
    • 0000632487 scopus 로고
    • Activity and Selectivity in the Reactions of Substituted α,β-Unsaturated Aldehydes
    • Marinelli, T. B. L. W.; Nabuurs, S.; Ponec, V. Activity and Selectivity in the Reactions of Substituted α,β-Unsaturated Aldehydes. J. Catal. 1995, 151, 431-438.
    • (1995) J. Catal. , vol.151 , pp. 431-438
    • Marinelli, T.B.L.W.1    Nabuurs, S.2    Ponec, V.3
  • 8
    • 0033524806 scopus 로고    scopus 로고
    • Double-bond Activation in Unsaturated Aldehydes: Conversion of Acrolein to Propene and Ketene on Pt(111) Surfaces
    • de Jesús, J. C.; Zaera, F. Double-bond Activation in Unsaturated Aldehydes: Conversion of Acrolein to Propene and Ketene on Pt(111) Surfaces. J. Mol. Catal. A: Chem. 1999, 138, 237-240.
    • (1999) J. Mol. Catal. A: Chem. , vol.138 , pp. 237-240
    • De Jesús, J.C.1    Zaera, F.2
  • 9
    • 77956943227 scopus 로고
    • The Effect of Carbonaceous Depositions on Activity and Selectivity in Hydrogenation of an Unsaturated Aldehyde
    • Bartholomew, C. H.; Butt, J. B. Elsevier: New York
    • Andersson, B.; Eek, M.; Wrammerfors, A˚. The Effect of Carbonaceous Depositions on Activity and Selectivity in Hydrogenation of an Unsaturated Aldehyde. Bartholomew, C. H.; Butt, J. B. Stud. Surf. Sci. Catal.; Elsevier: New York, 1991, Vol. 68, pp 161-168.
    • (1991) Stud. Surf. Sci. Catal. , vol.68 , pp. 161-168
    • Andersson, B.1    Eek, M.2    Wrammerfors, A˚.3
  • 10
    • 0002281837 scopus 로고
    • Alumina-Aluminum Phosphate as a Large-Pore Support and Its Application to Liquid Phase Hydrogenation
    • Marcelin, G.; Vogel, R. F.; Swift, H. E. Alumina-Aluminum Phosphate as a Large-Pore Support and Its Application to Liquid Phase Hydrogenation. J. Catal. 1983, 83, 42-49.
    • (1983) J. Catal. , vol.83 , pp. 42-49
    • Marcelin, G.1    Vogel, R.F.2    Swift, H.E.3
  • 11
    • 84873256499 scopus 로고    scopus 로고
    • Dynamic Modeling and Validation of 2-Ethyl-Hexenal Hydrogenation Process
    • Both, R.; Cormos, A. M.; Agachi, P. S.; Festila, C. Dynamic Modeling and Validation of 2-Ethyl-Hexenal Hydrogenation Process. Comput. Chem. Eng. 2013, 52, 100-111.
    • (2013) Comput. Chem. Eng. , vol.52 , pp. 100-111
    • Both, R.1    Cormos, A.M.2    Agachi, P.S.3    Festila, C.4
  • 12
    • 70449602614 scopus 로고    scopus 로고
    • Promotion Effects of Copper and Lanthanum Oxides on Nickel/Gamma-Alumina Catalyst in the Hydrotreating of Crude 2-Ethylhexanol
    • Yang, R.; Li, X.; Wu, J.; Zhang, X.; Zhang, Z. Promotion Effects of Copper and Lanthanum Oxides on Nickel/Gamma-Alumina Catalyst in the Hydrotreating of Crude 2-Ethylhexanol. J. Phys. Chem. C 2009, 113, 17787-17794.
    • (2009) J. Phys. Chem. C , vol.113 , pp. 17787-17794
    • Yang, R.1    Li, X.2    Wu, J.3    Zhang, X.4    Zhang, Z.5
  • 13
    • 0021389120 scopus 로고
    • Liquid-Phase Hydrogenation with Nickel Supported on Modified Alumina-Aluminum Phosphate
    • Marcelin, G.; Vogel, R. F.; Swift, H. E. Liquid-Phase Hydrogenation with Nickel Supported on Modified Alumina-Aluminum Phosphate. Ind. Eng. Chem. Prod. Res. Dev. 1984, 23, 41-44.
    • (1984) Ind. Eng. Chem. Prod. Res. Dev. , vol.23 , pp. 41-44
    • Marcelin, G.1    Vogel, R.F.2    Swift, H.E.3
  • 19
    • 0024107916 scopus 로고
    • Kinetics of Hydrogenation of 2-Ethylhexenal and Hydrogen/Deuterium Exchange on a Palladium/SilicaCatalyst in a Continuously Stirred Tank Reactor
    • Niklasson, C. Kinetics of Hydrogenation of 2-Ethylhexenal and Hydrogen/Deuterium Exchange on a Palladium/SilicaCatalyst in a Continuously Stirred Tank Reactor. Ind. Eng. Chem. Res. 1988, 27, 1990-1995.
    • (1988) Ind. Eng. Chem. Res. , vol.27 , pp. 1990-1995
    • Niklasson, C.1
  • 20
    • 0343441373 scopus 로고
    • Concentration Dependence of Ketone Hydrogenation Catalyzed by Ru, Pd, and Pt. Evidence for Weak Ketone Adsorption on Pd Surface
    • Sungbom, C.; Tanaka, K. Concentration Dependence of Ketone Hydrogenation Catalyzed by Ru, Pd, and Pt. Evidence for Weak Ketone Adsorption on Pd Surface. Bull. Chem. Soc. Jpn. 1982, 55, 2275-2276.
    • (1982) Bull. Chem. Soc. Jpn. , vol.55 , pp. 2275-2276
    • Sungbom, C.1    Tanaka, K.2
  • 21
    • 0036026685 scopus 로고    scopus 로고
    • A Density Functional Study of Adsorption Structures of Unsaturated Aldehydes on Pt(111): A Key Factor for Hydrogenation Selectivity
    • Delbecq, F.; Sautet, P. A Density Functional Study of Adsorption Structures of Unsaturated Aldehydes on Pt(111): A Key Factor for Hydrogenation Selectivity. J. Catal. 2002, 211, 398-406.
    • (2002) J. Catal. , vol.211 , pp. 398-406
    • Delbecq, F.1    Sautet, P.2
  • 22
    • 3142736571 scopus 로고    scopus 로고
    • Coverage Dependent Adsorption of Acrolein on Pt(111) from a Combination of First Principle Theory and HREELS Study
    • Loffreda, D.; Jugnet, Y.; Delbecq, F.; Bertolini, J. C.; Sautet, P. Coverage Dependent Adsorption of Acrolein on Pt(111) from a Combination of First Principle Theory and HREELS Study. J. Phys. Chem. B 2004, 108, 9085-9093.
    • (2004) J. Phys. Chem. B , vol.108 , pp. 9085-9093
    • Loffreda, D.1    Jugnet, Y.2    Delbecq, F.3    Bertolini, J.C.4    Sautet, P.5
  • 23
    • 84869487957 scopus 로고    scopus 로고
    • The Adsorption of Acrolein on a Pt(111): A Study of Chemical Bonding and Electronic Structure
    • Pirillo, S.; López-Corral, I.; Germán, E.; Juan, A. The Adsorption of Acrolein on a Pt(111): A Study of Chemical Bonding and Electronic Structure. Appl. Surf. Sci. 2012, 263, 79-85.
    • (2012) Appl. Surf. Sci. , vol.263 , pp. 79-85
    • Pirillo, S.1    López-Corral, I.2    Germán, E.3    Juan, A.4
  • 24
    • 84880881942 scopus 로고    scopus 로고
    • Density Functional Study of Acrolein Adsorption on Pt(111)
    • Pirillo, S.; López-Corral, I.; Germán, E.; Juan, A. Density Functional Study of Acrolein Adsorption on Pt(111). Vacuum 2014, 99, 259-264.
    • (2014) Vacuum , vol.99 , pp. 259-264
    • Pirillo, S.1    López-Corral, I.2    Germán, E.3    Juan, A.4
  • 25
    • 77956318410 scopus 로고    scopus 로고
    • Coverage Dependence of the Structure of Acrolein Adsorbed on Ag(111)
    • Ferullo, R.; Branda, M. M.; Illas, F. Coverage Dependence of the Structure of Acrolein Adsorbed on Ag(111). J. Phys. Chem. Lett. 2010, 1, 2546-2549.
    • (2010) J. Phys. Chem. Lett. , vol.1 , pp. 2546-2549
    • Ferullo, R.1    Branda, M.M.2    Illas, F.3
  • 26
    • 84883797059 scopus 로고    scopus 로고
    • Structure and Stability of Acrolein and Allyl Alcohol Networks on Ag(111) from Density Functional Theory Based Calculations with Dispersion Corrections
    • Ferullo, R. M.; Branda, M. M.; Illas, F. Structure and Stability of Acrolein and Allyl Alcohol Networks on Ag(111) from Density Functional Theory Based Calculations with Dispersion Corrections. Surf. Sci. 2013, 617, 175-182.
    • (2013) Surf. Sci. , vol.617 , pp. 175-182
    • Ferullo, R.M.1    Branda, M.M.2    Illas, F.3
  • 27
    • 72249111744 scopus 로고    scopus 로고
    • Chemoselective Catalytic Hydrogenation of Acrolein on Ag(111): Effect of Molecular Orientation on Reaction Selectivity
    • Brandt, K.; Chiu, M. E.; Watson, D. J.; Tikhov, M. S.; Lambert, R. M. Chemoselective Catalytic Hydrogenation of Acrolein on Ag(111): Effect of Molecular Orientation on Reaction Selectivity. J. Am. Chem. Soc. 2009, 131, 17286-17290.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 17286-17290
    • Brandt, K.1    Chiu, M.E.2    Watson, D.J.3    Tikhov, M.S.4    Lambert, R.M.5
  • 28
    • 56249126311 scopus 로고    scopus 로고
    • Hydrogenation of Conjugated C=C and C=O bonds: Quantum Chemical Preview before Metal Catalysis
    • Li, Z.; Chen, Z.-X.; Kang, G.; He, X. Hydrogenation of Conjugated C=C and C=O bonds: Quantum Chemical Preview before Metal Catalysis. J. Mol. Struct.: THEOCHEM 2008, 870, 61-64.
    • (2008) J. Mol. Struct.: THEOCHEM , vol.870 , pp. 61-64
    • Li, Z.1    Chen, Z.-X.2    Kang, G.3    He, X.4
  • 29
    • 67349112376 scopus 로고    scopus 로고
    • Theoretical Elucidation of the Selectivity Changes for the Hydrogenation of Unsaturated Aldehydes on Pt(111)
    • Laref, S.; Delbecq, F.; Loffreda, D. Theoretical Elucidation of the Selectivity Changes for the Hydrogenation of Unsaturated Aldehydes on Pt(111). J. Catal. 2009, 265, 35-42.
    • (2009) J. Catal. , vol.265 , pp. 35-42
    • Laref, S.1    Delbecq, F.2    Loffreda, D.3
  • 30
    • 0000735247 scopus 로고    scopus 로고
    • Molecular and Solid-State Tests of Density Functional Approximations: LSD, GGAs, and Meta-GGAs
    • Kurth, S.; Perdew, J. P.; Blaha, P. Molecular and Solid-State Tests of Density Functional Approximations: LSD, GGAs, and Meta-GGAs. Int. J. Quantum Chem. 1999, 75, 889-909.
    • (1999) Int. J. Quantum Chem. , vol.75 , pp. 889-909
    • Kurth, S.1    Perdew, J.P.2    Blaha, P.3
  • 31
    • 4243943295 scopus 로고    scopus 로고
    • Generalized Gradient Approximation Made Simple
    • Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple. Phys. Rev. Lett. 1996, 77, 3865-3868.
    • (1996) Phys. Rev. Lett. , vol.77 , pp. 3865-3868
    • Perdew, J.P.1    Burke, K.2    Ernzerhof, M.3
  • 32
    • 33750559983 scopus 로고    scopus 로고
    • Semiempirical GGA-Type Density Functional Constructed with a Long-Range Dispersion Correction
    • Grimme, S. Semiempirical GGA-Type Density Functional Constructed with a Long-Range Dispersion Correction. J. Comput. Chem. 2006, 27, 1787-1799.
    • (2006) J. Comput. Chem. , vol.27 , pp. 1787-1799
    • Grimme, S.1
  • 33
    • 34447260582 scopus 로고
    • An all-Electron Numerical Method for Solving the Local Density Functional for Polyatomic Molecules
    • Delley, B. An all-Electron Numerical Method for Solving the Local Density Functional for Polyatomic Molecules. J. Chem. Phys. 1990, 92, 508-517.
    • (1990) J. Chem. Phys. , vol.92 , pp. 508-517
    • Delley, B.1
  • 34
    • 0034319689 scopus 로고    scopus 로고
    • 3Approach
    • 3Approach. J. Chem. Phys. 2000, 113, 7756-7764.
    • (2000) J. Chem. Phys. , vol.113 , pp. 7756-7764
    • Delley, B.1
  • 35
    • 0030121735 scopus 로고    scopus 로고
    • Fast Calculation of Electrostatics in Crystals and Large Molecules
    • Delley, B. Fast Calculation of Electrostatics in Crystals and Large Molecules. J. Phys. Chem. 1996, 100, 6107-6110.
    • (1996) J. Phys. Chem. , vol.100 , pp. 6107-6110
    • Delley, B.1
  • 36
    • 85022583881 scopus 로고
    • The Isomers of Silacyclopropane
    • Gordon, M. S. The Isomers of Silacyclopropane. Chem. Phys. Lett. 1980, 76, 163-168.
    • (1980) Chem. Phys. Lett. , vol.76 , pp. 163-168
    • Gordon, M.S.1
  • 37
    • 77956055866 scopus 로고    scopus 로고
    • DFT Studies of the pH Dependence of the Reactivity of Methanol on a Pd(111) Surface
    • Qi, X. Q.; Wei, Z. D.; Li, L. L.; Li, L.; Ji, M. B.; Zhang, Y.; Xia, M. R.; Ma, X. L. DFT Studies of the pH Dependence of the Reactivity of Methanol on a Pd(111) Surface. J. Mol. Struct. 2010, 980, 208-213.
    • (2010) J. Mol. Struct. , vol.980 , pp. 208-213
    • Qi, X.Q.1    Wei, Z.D.2    Li, L.L.3    Li, L.4    Ji, M.B.5    Zhang, Y.6    Xia, M.R.7    Ma, X.L.8
  • 38
    • 0037110056 scopus 로고    scopus 로고
    • Hardness Conserving Semilocal Pseudopotentials
    • Delley, B. Hardness Conserving Semilocal Pseudopotentials. Phys. Rev. B 2002, 66, 155125.
    • (2002) Phys. Rev. B , vol.66 , pp. 155125
    • Delley, B.1
  • 39
    • 0001149392 scopus 로고
    • The Synchronous-Transit Method for Determining Reaction Pathways and Locating Molecular Transition States
    • Halgren, T. A.; Lipscomb, W. N. The Synchronous-Transit Method for Determining Reaction Pathways and Locating Molecular Transition States. Chem. Phys. Lett. 1977, 49, 225-232.
    • (1977) Chem. Phys. Lett. , vol.49 , pp. 225-232
    • Halgren, T.A.1    Lipscomb, W.N.2
  • 40
    • 30244442116 scopus 로고
    • Competitive C=C and C=O Adsorption of α-β-Unsaturated Aldehydes on Pt and Pd Surfaces in Relation with the Selectivity of Hydrogenation Reactions: A Theoretical Approach
    • Delbecq, F.; Sautet, P. Competitive C=C and C=O Adsorption of α-β-Unsaturated Aldehydes on Pt and Pd Surfaces in Relation with the Selectivity of Hydrogenation Reactions: A Theoretical Approach. J. Catal. 1995, 152, 217-236.
    • (1995) J. Catal. , vol.152 , pp. 217-236
    • Delbecq, F.1    Sautet, P.2
  • 42
    • 0038505336 scopus 로고    scopus 로고
    • Adsorption of Unsaturated Aldehydes on the (111) Surface of a Pt-Fe Alloy Catalyst from First Principles
    • Hirschl, R.; Delbecq, F.; Sautet, P.; Hafner, J. Adsorption of Unsaturated Aldehydes on the (111) Surface of a Pt-Fe Alloy Catalyst from First Principles. J. Catal. 2003, 217, 354-366.
    • (2003) J. Catal. , vol.217 , pp. 354-366
    • Hirschl, R.1    Delbecq, F.2    Sautet, P.3    Hafner, J.4
  • 44
    • 0037421978 scopus 로고    scopus 로고
    • A First-Principles Analysis of Acetylene Hydrogenation over Pd(111)
    • Sheth, P. A.; Neurock, M.; Smith, C. M. A First-Principles Analysis of Acetylene Hydrogenation over Pd(111). J. Phys. Chem. B 2003, 107, 2009-2017.
    • (2003) J. Phys. Chem. B , vol.107 , pp. 2009-2017
    • Sheth, P.A.1    Neurock, M.2    Smith, C.M.3
  • 47
    • 0016026119 scopus 로고
    • Adsorption of Hydrogen on Palladium Single Crystal Surfaces
    • Conrad, H.; Ertl, G.; Latta, E. E. Adsorption of Hydrogen on Palladium Single Crystal Surfaces. Surf. Sci. 1974, 41, 435-446.
    • (1974) Surf. Sci. , vol.41 , pp. 435-446
    • Conrad, H.1    Ertl, G.2    Latta, E.E.3
  • 48
    • 0000712328 scopus 로고    scopus 로고
    • 2Dissociative Adsorption on Pd(111)
    • 2Dissociative Adsorption on Pd(111). Phys. Rev. B 1997, 56, 15396-15403.
    • (1997) Phys. Rev. B , vol.56 , pp. 15396-15403
    • Dong, W.1    Hafner, J.2
  • 49
    • 84861794510 scopus 로고    scopus 로고
    • Origin of the Increase of Activity and Selectivity of Nickel Doped by Au, Ag, and Cu for Acetylene Hydrogenation
    • Yang, B.; Burch, R.; Hardacre, C.; Headdock, G.; Hu, P. Origin of the Increase of Activity and Selectivity of Nickel Doped by Au, Ag, and Cu for Acetylene Hydrogenation. ACS Catal. 2012, 2, 1027-1032.
    • (2012) ACS Catal. , vol.2 , pp. 1027-1032
    • Yang, B.1    Burch, R.2    Hardacre, C.3    Headdock, G.4    Hu, P.5
  • 50
    • 84879495799 scopus 로고    scopus 로고
    • Influence of Surface Structures, Subsurface Carbon and Hydrogen, and Surface Alloying on the Activity and Selectivity of Acetylene Hydrogenation on Pd Surfaces: A Density Functional Theory Study
    • Yang, B.; Burch, R.; Hardacre, C.; Headdock, G.; Hu, P. Influence of Surface Structures, Subsurface Carbon and Hydrogen, and Surface Alloying on the Activity and Selectivity of Acetylene Hydrogenation on Pd Surfaces: A Density Functional Theory Study. J. Catal. 2013, 305, 264-276.
    • (2013) J. Catal. , vol.305 , pp. 264-276
    • Yang, B.1    Burch, R.2    Hardacre, C.3    Headdock, G.4    Hu, P.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.