Citation: ZENG Lihui, LI Yuefeng, YAN Haoxiang, ZENG Yongkang, ZHANG Zhixiang, LIU Zhongwen, LIU Zhaotie. Catalytic Hydrogenation Performance of p-tert-Butyl-α-Methyl Cinnamaldehydeover Precious Metal Catalysts[J]. Chinese Journal of Applied Chemistry, ;2020, 37(3): 322-331. doi: 10.11944/j.issn.1000-0518.2020.03.190192 shu

Catalytic Hydrogenation Performance of p-tert-Butyl-α-Methyl Cinnamaldehydeover Precious Metal Catalysts

a.
Key Laboratory of Applied Surface and Colloid Chemistry(Ministry of Education), School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China
b.
Kaili Catalyst & New Materials Co., Ltd. Xi'an 710201, China
c.
College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an 710021, China

Corresponding author: LIU Zhaotie, ztliu@snnu.edu.cn
Received Date: 9 July 2019
Revised Date: 10 January 2020
Accepted Date: 11 February 2020

Fund Project: the Key Industry Innovation Chain of Shaanxi Science and Technology Department(group) 2019ZDLGY06-04Supported by the Key Industry Innovation Chain of Shaanxi Science and Technology Department(group)(No.2019ZDLGY06-04)

Figures(10)

In this paper, Fourier transform infrared spectroscopy (FT-IR), N₂ adsorption-desorption, X-ray diffraction (XRD) andtransmission electron microscopy (TEM) were used to characterize the activated carbon treated via microwave with KOH. The results show that the oxygen-containing groups on the surface of activated carbon increase greatly, and the number of micropores decrease significantly. The selective catalytic hydrogenation performances of p-tert-butyl-α-methyl cinnamaldehyde over Pt, Pd, Ru and Rh supported on activated carbon were investigated. The Pt/C catalyst shows excellent selective hydrogenation for C═O, while the Pd/C catalyst has good selectivity for hydrogenation of C═C. The product distribution of selective hydrogenation of p-tert-butyl-α-methylcinnamaldehyde catalyzed by Pd-Pt bimetallic catalyst was also studied. The results show that the selective hydrogenation of C═O is gradually increased with an increase of Pt content, while the selectivity of hydrogenation of C═C decreases gradually over the Pd-Pt bimetallic catalyst. An optimal catalytic performance is obtained over Pd-Pt bimetallic catalyst when m(Pd):m(Pt)=4:1.
- microwave-assisted,
- activated carbon,
- noble metal supported catalyst,
- selective hydrogenation,
- p-tert-butyl-α-methylcinnamaldehyde
1. [1]
  Su J, Chen J S. Synthetic Porous Materials Applied in Hydrogenation Reactions[J]. Micropor Mesopor Mater, 2017,237:246-259. doi: 10.1016/j.micromeso.2016.09.039
2. [2]
  Long J, Shen K, Li Y W. Bifunctional N-Doped Co@C Catalysts for Base-Free Transfer Hydrogenations of Nitriles:Controllable Selectivity to Primary Amines vs Imines[J]. ACS Catal, 2016,7(1):275-284. doi: 10.1021/acscatal.6b02327
3. [3]
  Amir M, Kurtan U, Baykal A. Synthesis and Application of Magnetically Recyclable Nanocatalyst Fe₃O₄@Nico@Cu in the Reduction of Azo Dyes[J]. Chinese J Catal, 2015,36(8):1280-1286. doi: 10.1016/S1872-2067(15)60879-8
4. [4]
  Wang H, Rempel G L. Aqueous-Phase Catalytic Hydrogenation of Unsaturated Polymers[J]. Catal Today, 2015,247:117-123. doi: 10.1016/j.cattod.2014.04.027
5. [5]
  Pérez L N, Moreno-Marrodan C, Barbaro P. PdNP@Titanate Nanotubes as Effective Catalyst for Continuous-Flow Partial Hydrogenation Reactions[J]. ChemCatChem, 2016,8(S):1001-1011.
6. [6]
  Teddy J, Falqui A, Corrias A. Influence of Particles Alloying on the Performances of Pt-Ru/CNT Catalysts for Selective Hydrogenation[J]. J Catal, 2011,278(1):59-70.
7. [7]
  Wu J C S, Chen W C. A Novel BN Supported Bi-metal Catalyst for Selective Hydrogenation of Crotonaldehyde[J]. Appl Catal A, 2005,289(2):179-185.
8. [8]
  Leng F Q, Gerber I C, Axet M R. Selectivity Shifts in Hydrogenation of Cinnamaldehyde on Electro-deficient Ruthenium Nanoparticles[J]. C R Chim, 2018,21(3/4):346-353.
9. [9]
  FU Xiancai, SHEN Wenxia, YAO Tianyang. Physical Chemistry(The Fourth edition)(The First Volume)[M]. Beijing:Higher Education Press, 1989, 66(in Chinese).
10. [10]
  YI Shumei. Studies of Hydrogenation Reaction Kinetics of α, β-Unsaturated Aldehydes and Ketones over Amorphous Alloy NiB[D]. Dalian: Dalian University of Technology, 2007(in Chinese).
11. [11]
  Bai Y, Cherkasov N, Huband S. Highly Selective Continuous Flow Hydrogenation of Cinnamaldehyde to Cinnamyl Alcohol in a Pt/SiO₂ Coated Tube Reactor[J]. Catalysts, 2018,58(8):1-18.
12. [12]
  Hu D, Fan W Q, Liu Z. Three-Dimensionally Hierarchical Pt/C Nanocompsite with Ultra-High Dispersion of Pt Nanoparticles as a Highly Efficient Catalyst for Chemoselective Cinnamaldehyde Hydrogenation[J]. ChemCatChem, 2018,10(4):779-788. doi: 10.1002/cctc.201701301
13. [13]
  FAN Chengyou. Spices and Their Applications[M]. Beijing:Chemical Industry Press, 1990, 263(in Chinese).
14. [14]
  Bartok M, Molnar A. The Chemistry of Double-Bonded Functional Groups[M]. New York:Wiley, 1983:843-865.
15. [15]
  ZHANG Guoan, SHI Gailiang, XUE Xiangru. Synthesis of 4-tert-Butyl-β-chloro-α-methyl Cinnamaldehyde[J]. Chem World, 1991(1):12-13.
16. [16]
  SONG Shuzhong, TANG Yongshan, PAN Guizhi. Seletive Hydrogenation of Substituted α-Methyl Cinnamic Aldehyde[J]. Fine Chem, 1994,4(11):16-18.
17. [17]
  LIANG Yan, RONG Zemin, ZHENG Feiyue. Selective Hydrogenation of p-tert-Butyl-α-methyl Cinnamaldehyde to Lilial over Modified Pd/C[J]. Fine Chem, 2011,6(28):564-567.
18. [18]
  Joseph L, Paramus N J, Alvin F. Hydrogenation of CinnamicAldehydes and Derivatives Thereof: US, 3280192[P]. 1966-10-18.
19. [19]
  DENG Qinying, LIU Lan, DENG Huimin. Spectral Analysis Tutorial[M]. Beijing:Science Press, 2007:29-72(in Chinese).
20. [20]
  Laine J, Calafat A, Labady M. Preparation and Characterization of Activated Carbons from Coconut Shell Impregnated with Phosphoric Acid[J]. Carbon, 1989,27(2):191-195. doi: 10.1016/0008-6223(89)90123-1
21. [21]
  Shen W Z, Li Z J, Liu Y H. Surface Chemical Functional Groups Modification of Porous Carbon[J]. Recent Pat Chem Eng, 2008,1(1):27-40. doi: 10.2174/2211334710801010027
22. [22]
  CHEN Zhening, CHEN Zheng, FU Gang, et al. Mechanisms for the Selective Reduction of Cinnamaldehyde[C]//The 27th Annual Meeting of the Chinese Chemical Society, Summary of the 11th Session, 2010, 11-P-098(in Chinese).
23. [23]
  Giroir-Fendler A, Richard D, Gallezot P. Selectivity in Cinnamaldehyde Hydrogenation of Group-Ⅷ Metals Supported on Graphite and Carbon[J]. Stud Surf Sci Catal, 1988,41:171-178. doi: 10.1016/S0167-2991(09)60812-0
24. [24]
  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]. J Catal, 1995,152(2):217-236.
25. [25]
  Matsui T, Harada M, Bando K K. EXAFS Study on the Sulfidation Behavior of Pd, Pt and Pd-Pt Catalysts Supported on Amorphous Silica and High-silica USY Zeolite[J]. Appl Catal A, 2005,290(1/2):73-80.
26. [26]
  Niquille-Röthlisberger A, Prins R. Hydrodesulfurization of 4, 6-Dimethyldibenzothiophene and Dibenzothiopheneover Alumina-Supported Pt, Pd, and Pt-Pd Catalysts[J]. J Catal, 2006,242(1):207-216.
27. [27]
  Yasuda H, Yoshimura Y. Hydrogenation of Tetralinover Zeolite-supported Pd-Pt Catalysts in the Presence of Dibenzothiophene[J]. Catal Lett, 1997,46(1/2):43-48. doi: 10.1023/A:1019021224505
28. [28]
  Matsubayashi N, Yasuda H, Imaura M. EXAFS Study on Pd-Pt Catalyst Supported on USY Zeolite[J]. Catal Today, 1998,45(1/4):375-380.
29. [29]
  Yasuda H, Matsubayashi N, Sato T. Confirmation of Sulfur Tolerance of Bimetallic Pd-Pt Supported on Highly Acidic USY Zeolite by EXAFS[J]. Catal Lett, 1998,54(1/2):23-27. doi: 10.1023/A:1019079906043
30. [30]
  Guillon E, Lynch J, Uzio D. Characterisation of Bimetallic Platinum Systems:Application to the Reduction of Aromatics in Presence of Sulfur[J]. Catal Today, 2001,65(2/4):201-208.
31. [31]
  Lee J K, Rhee H K. Sulfur Tolerance of Zeolite Beta-Supported Pd-Pt Catalysts for the Isomerization of n-Hexane[J]. J Catal, 1998,177(2):208-216.
1. [1]
  Jianjun LI , Mingjie REN , Lili ZHANG , Lingling ZENG , Huiling WANG , Xiangwu MENG . UV-assisted degradation of tetracycline hydrochloride by MnFe₂O₄@activated carbon activated persulfate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1869-1880. doi: 10.11862/CJIC.20240187
2. [2]
  Qiqi Li , Su Zhang , Yuting Jiang , Linna Zhu , Nannan Guo , Jing Zhang , Yutong Li , Tong Wei , Zhuangjun Fan . 前驱体机械压实制备高密度活性炭及其致密电容储能性能. Acta Physico-Chimica Sinica, 2025, 41(3): 2406009-. doi: 10.3866/PKU.WHXB202406009
3. [3]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
4. [4]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
5. [5]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
6. [6]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
7. [7]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
8. [8]
  Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO₂ hydrogenation over a Mg-doped In₂O_3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421
9. [9]
  Hailian Tang , Siyuan Chen , Qiaoyun Liu , Guoyi Bai , Botao Qiao , Fei Liu . Stabilized Rh/hydroxyapatite Catalyst for Furfuryl Alcohol Hydrogenation: Application of Oxidative Strong Metal-Support Interactions in Reducing Conditions. Acta Physico-Chimica Sinica, 2025, 41(4): 100036-. doi: 10.3866/PKU.WHXB202408004
10. [10]
  Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO₂ reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
11. [11]
  Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
12. [12]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
13. [13]
  Shuang Yang , Qun Wang , Caiqin Miao , Ziqi Geng , Xinran Li , Yang Li , Xiaohong Wu . Ideological and Political Education Design for Research-Oriented Experimental Course of Highly Efficient Hydrogen Production from Water Electrolysis in Aerospace Perspective. University Chemistry, 2024, 39(11): 269-277. doi: 10.12461/PKU.DXHX202403044
14. [14]
  Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH₂ supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
15. [15]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
16. [16]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
17. [17]
  Hailang JIA , Hongcheng LI , Pengcheng JI , Yang TENG , Mingyun GUAN . Preparation and performance of N-doped carbon nanotubes composite Co₃O₄ as oxygen reduction reaction electrocatalysts. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 693-700. doi: 10.11862/CJIC.20230402
18. [18]
  Shengbiao Zheng , Liang Li , Nini Zhang , Ruimin Bao , Ruizhang Hu , Jing Tang . Metal-Organic Framework-Derived Materials Modified Electrode for Electrochemical Sensing of Tert-Butylhydroquinone: A Recommended Comprehensive Chemistry Experiment for Translating Research Results. University Chemistry, 2024, 39(7): 345-353. doi: 10.3866/PKU.DXHX202310096
19. [19]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
20. [20]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(2532)
HTML views(432)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142