Citation: LUO Wei, XUE Ji-long, MENG Yue, QIAN Meng-dan, FANG Lei, XIA Sheng-jie, NI Zhe-ming. Adsorption and selective hydrogenation mechanism of cinnamaldehyde on Pt(111) surface and Pt₁₄ cluster[J]. Journal of Fuel Chemistry and Technology, ;2018, 46(7): 818-825. shu

Adsorption and selective hydrogenation mechanism of cinnamaldehyde on Pt(111) surface and Pt₁₄ cluster

LUO Wei ¹ ,
XUE Ji-long ¹ ,
MENG Yue ² ,
QIAN Meng-dan ¹ ,
FANG Lei ¹ ,
XIA Sheng-jie ^1,, ,
NI Zhe-ming ^1,,

1.
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China
2.
School of Life Sciences, Huzhou University, Huzhou 313000, China

Corresponding author: XIA Sheng-jie, jchx@zjut.edu.cn NI Zhe-ming, xiasj@zjut.edu.cn
Received Date: 12 March 2018
Revised Date: 24 May 2018

Fund Project: the National Natural Science Foundation of China 21503188the Zhejiang Provincial Natural Science Foundation of China LQ15B030002The project was supported by the National Natural Science Foundation of China (21503188) and the Zhejiang Provincial Natural Science Foundation of China (LQ15B030002)

Figures(6)

The adsorption and the mechanism for selective hydrogenation of cinnamaldehyde (CAL) on Pt (111) surface and Pt₁₄ cluster were investigated by using density functional theory (DFT). The results illustrate that the synergistic adsorption of CAL molecule on Pt (111) surface with C=O and C=C bonds is most stable at the Hcp position, whereas most stable adsorption of CAL appears on the Pt₁₄ cluster with C=C bond; the adsorption of CAL on the Pt₁₄ cluster is stronger than that on Pt(111) surface. The reaction barriers for each elementary reaction were determined from the transition state search and the results suggest that CAL was preferentially hydrogenated at C=O on the Pt(111) surface and Pt₁₄ cluster, forming cinnamyl alcohol (COL); the hydrogenation of O atom takes the priority. Both Pt plate and cluster have good selectivity for hydrogenation of CAL to COL. The reaction barrier of CAL hydrogenation on Pt(111) surface is lower than that on Pt₁₄ cluster, indicating that the catalytic activity and selectivity of CAL hydrogenation are closely related to the structure of Pt catalysts; Pt(111) surface is more favorable for catalyzing the hydrogenation of CAL to COL.
- cinnamaldehyde,
- adsorption,
- hydrogenation,
- platinum,
- catalytic,
- density functional theory
1. [1]
  GAO Shuang, CHEN Xiao-lu, WANG Jian-jiang, DU Guo-feng, LI Zhen, WANG Zhen-lü. Selective hydrogenation of cinnamaldehyde to cinnamyl alcohol on Ru-based catalysts[J]. Petrochem Technol, 2017,46(7):862-868.
2. [2]
  CLAUS P, BRULCKNER A, MOHR C, HOFMEISTER H. Supported gold nanoparticles from quantum dot to mesoscopic size scale:Effect of electronic and structural properties on catalytic hydrogenation of conjugated functional groups[J]. J Am Chem Soc, 2000,122(46):11430-11439. doi: 10.1021/ja0012974
3. [3]
  BUS E, PRINS R, BOKHOVEN J A V. Origin of the cluster-size effect in the hydrogenation of cinnamaldehyde over supported Au catalysts[J]. Catal Commun, 2007,8(9):1397-1402. doi: 10.1016/j.catcom.2006.11.040
4. [4]
  HISCHL 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]. J Catal, 2003,217(2):354-366. doi: 10.1016/S0021-9517(03)00057-5
5. [5]
  LI Hui, MA Chun-jing, LI He-xing. Study on cinnamaldehyde hydrogenation to 3-phenylpropyl aldehyde at atmospheric pressure over Ni-Co-B amorphous alloys[J]. Acta Chim Sin, 2006,64(19):1947-1953. doi: 10.3321/j.issn:0567-7351.2006.19.002
6. [6]
  Ni X J, ZHANG B S, LI C, PANG M, SU D S, WILLIAMS C T, LIANG C H. Microwave-assisted green synthesis of uniform Ru nanoparticles supported on non-functional carbon nanotubes for cinnamaldehyde hydrogenation[J]. Catal Commun, 2012,24(24):65-69.
7. [7]
  MARCHI A J, GORDO D A, TRASARTI A F, APESTEGUIA C R. Liquid phase hydrogenation of cinnamaldehyde on Cu-based catalysts[J]. Appl Catal A:Gen, 2003,249(1):53-67. doi: 10.1016/S0926-860X(03)00199-6
8. [8]
  JOSEPH ANTONY RAJ A, PRAKASH M G, ELANGOVAN T, VISWANATHAN B. Selective hydrogenation of cinnamaldehyde over cobalt supported on alumina, silica and titania[J]. Catal Lett, 2012,142(1):87-94. doi: 10.1007/s10562-011-0693-0
9. [9]
  LUO Q Q, WANG T, BELLER R, JIAO H J. Acrolein hydrogenation on Ni(111)[J]. J Phys Chem C, 2013,117(24):12715-12724. doi: 10.1021/jp403972b
10. [10]
  QIAN Meng-dan, XUE Ji-long, XIA Sheng-jie, NI Zhe-ming, JIANG Jun-hui, CAO Yong-yong. Decarbonylation and hydrogenation reaction of furfural on Pd/Cu(111) surface[J]. J Fuel Chem Technol, 2017,45(1):34-42.
11. [11]
  YUAN E, WANG L, ZHANG X W, FENG R, WU C, LI G Z. Density functional theory analysis of anthraquinone derivative hydrogenation over palladium catalyst[J]. Chem Phys Chem, 2016,17(23):3974-3984. doi: 10.1002/cphc.201600874
12. [12]
  ROJAS H, DIAZ G, MARTINE J J, CASTANEDA C, GOMEZ-CORTES A, ARENAS-ALATORRE J. Hydrogenation of α, β-unsaturated carbonyl compounds over Au and Ir supported on SiO₂[J]. J Mol Catal A:Chem, 2012,363(364):122-128.
13. [13]
  IDE M S, HAO B, NEUROCK M, DAVIS R J. Mechanistic insights on the hydrogenation of α, β-unsaturated ketones and aldehydes to unsaturated alcohols over metal catalysts[J]. ACS Catal, 2012,2(4):671-683. doi: 10.1021/cs200567z
14. [14]
  ZANELLA R, LOUIS C, GIORGIO S, TOUROUDE R. Crotonaldehyde hydrogenation by gold supported on TiO₂:Structure sensitivity and mechanism[J]. J Catal, 2004,223(2):328-339. doi: 10.1016/j.jcat.2004.01.033
15. [15]
  LOFFREDA D, DELLECQ F, VIGNE F, SAUTET P. Catalytic hydrogenation of unsaturated aldehydes on Pt(111):Understanding the selectivity from first-principles calculations[J]. Angew Chem Int Ed, 2005,44(33):5279-5282. doi: 10.1002/(ISSN)1521-3773
16. [16]
  HAN Q, LIU Y F, WANG D, YUAN F L, NIU X Y, ZHU Y J. Effect of carbon nanosheets with different graphitization degree as support of noble metal on selective hydrogenation of cinnamaldehyde[J]. Rsc Adv, 2016,6(100):98356-98364. doi: 10.1039/C6RA17979G
17. [17]
  ABID M, PAUL-BONCOR V, TOUROUDE R. Pt/CeO₂ catalysts in crotonaldehyde hydrogenation:Selectivity, metal particle size and SMSI states[J]. Appl Catal A:Gen, 2006,297(1):48-59. doi: 10.1016/j.apcata.2005.08.048
18. [18]
  MAHATA N, GONCALVE F, PEREIRA M F R, FIGUEIREDO J L. Selective hydrogenation of cinnamaldehyde to cinnamyl alcohol over mesoporous carbon supported Fe and Zn promoted Pt catalyst[J]. Appl Catal A:Gen, 2008,339(2):159-168. doi: 10.1016/j.apcata.2008.01.023
19. [19]
  TEDDY J, FALQUI A, CORRIAS A, CARTA D, LECANTE P, GERBER I, SERP P. Influence of particles alloying on the performances of Pt-Ru/CNT catalysts for selective hydrogenation[J]. J Catal, 2011,278(1):59-70. doi: 10.1016/j.jcat.2010.11.016
20. [20]
  JOB N, PIRARD R, MARIEN J, PIRARD J P. Porous carbon xerogels with texture tailored by pH control during sol-gel process[J]. Carbon, 2004,42(3):619-628. doi: 10.1016/j.carbon.2003.12.072
21. [21]
  DURNDELL L J, PARLETT C M, HONDOW N S, ISAACS M A, WILSON K, LEE A F. Selectivity control in Pt-catalyzed cinnamaldehyde hydrogenation[J]. Sci Rep, 2015,59425. doi: 10.1038/srep09425
22. [22]
  TUOKKO S, PIHKO P M, HONKALA K. First principles calculations for hydrogenation of acrolein on Pd and Pt:Chemoselectivity depends on steric effects on the surface[J]. Angew Chem Int Ed, 2016,55(5):1670-1674. doi: 10.1002/anie.201507631
23. [23]
  CAO X M, BURCH R, HARDCRE C, HU P. Reaction mechanisms of crotonaldehyde hydrogenation on Pt(111):Density functional theory and microkinetic modeling[J]. J Phys Chem C, 2011,115(40):19819-19827. doi: 10.1021/jp206520w
24. [24]
  YANG X, WANG A, WANG X, ZHANG T, HAN K, LI J. Combined experimental and theoretical investigation on the selectivities of Ag, Au, and Pt catalysts for hydrogenation of crotonaldehyde[J]. J Phys Chem C, 2009,113(49):97-102.
25. [25]
  LI L C, WANG W, WANG X L, ZHSNG L. Investigating the mechanism of the selective hydrogenation reaction of cinnamaldehyde catalyzed by Pt_n clusters[J]. J Mol Model, 2016,22(8):1-11.
26. [26]
  JIANG Z, QIN P, FANG T. Theoretical study of NH₃ decomposition on Pd-Cu(111) and Cu-Pd (111) surfaces:A comparison with clean Pd(111) and Cu(111)[J]. Appl Surf Sci, 2016,371:337-342. doi: 10.1016/j.apsusc.2016.02.231
27. [27]
  GOVIND N, PETERSEN M, FITZGERAID G, KING-SMITH D, ANDZELM J. A generalized synchronous transit method for transition state location[J]. Comput Mater Sci, 2003,28(2):250-258.
28. [28]
  XIAO Xue-chun, SHI Wi, NI Zhe-ming. Selective hydrogenation mechanism of cinnamaldehyde on Au(111) surface[J]. Acta Phys-Chim Sin, 2014,30(8):1456-1464. doi: 10.3866/PKU.WHXB201406091
29. [29]
  JIANG Jun-hui, QIAN Meng-dan, XUE Ji-long, XIA Sheng-jie, NI Zhe-ming, SHAO Meng-meng. Comparison of properties of In-Au(111) and Ir-Au(111) alloy surfaces, and their adsorption to crotonaldehyde[J]. Acta Phys-Chim Sin, 2016,32(12):2932-2940. doi: 10.3866/PKU.WHXB201609302
30. [30]
  YANG X F, WANG A Q, WANG X D, ZHANG T, HAN K L, LI J. Combined experimental and theoretical investigation on the selectivities of Ag, Au, and Pt catalysts for hydrogenation of crotonaldehyde[J]. J Phys Chem C, 2009,113(49):20918-20926. doi: 10.1021/jp905687g
31. [31]
  PIRILLO S, LOPEZ-CORRAL I, GERMAN E, JUAN A. Density functional study of acrolein adsorption on Pt (111)[J]. Vacuum, 2014,99(1):259-264.
32. [32]
  LIU R Q. Adsorption and dissociation of H₂O on Au(111) surface:A DFT study[J]. Comput Theor Chem, 2013,1019(1):141-145.
33. [33]
  WEI S P, ZHAO Y T, FAN G L, YANG L, LI F. Structure-dependent selective hydrogenation of cinnamaldehyde over high-surface-area CeO₂-ZrO₂ composites supported Pt nanoparticles[J]. Chem Eng J, 2017,322(15):234-245.
34. [34]
  LIU H, MEI Q, LI S, YANG Y, WANG Y, LIU H, ZHENG L, AN P, ZHANG J, HAN B. Selective hydrogenation of unsaturated aldehydes over Pt nanoparticles promoted by the cooperation of steric and electronic effects[J]. Chem Commun, 2018,54(8):908-911. doi: 10.1039/C7CC08942B
35. [35]
  YANG B, CHERKASOV N, HUBAND S, WALKER D, WALTON R I, REBROV E. Highly selective continuous flow hydrogenation of cinnamaldehyde to cinnamyl alcohol in a Pt/SiO₂ coated tube reactor[J]. Catalysts, 2018,8(2)58. doi: 10.3390/catal8020058
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沈阳化工大学材料科学与工程学院沈阳 110142

Adsorption and selective hydrogenation mechanism of cinnamaldehyde on Pt(111) surface and Pt14 cluster

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通讯作者: 陈斌, bchen63@163.com

Adsorption and selective hydrogenation mechanism of cinnamaldehyde on Pt(111) surface and Pt₁₄ cluster