Citation: Qi Lianshan, Wang Tao, Wei Yongmei, Tian Hengshui. Study on the Effect of Co-reductant Aldehydes on Epoxidation of Propylene Catalyzed by Metalloporphyrins[J]. Chinese Journal of Organic Chemistry, ;2020, 40(5): 1305-1309. doi: 10.6023/cjoc201910028 shu

Study on the Effect of Co-reductant Aldehydes on Epoxidation of Propylene Catalyzed by Metalloporphyrins

School of Chemical Engineering, East China University of Science and Technology, Shanghai 200237

Corresponding author: Tian Hengshui, hengshuitian@126.com
Received Date: 23 October 2019
Revised Date: 23 December 2019
Available Online: 21 January 2020

Figures(7)

On the basis of density functional theory, theoretical calculation is conducted to obtain the free energy barriers of the reaction path, which may exist in the process of propylene epoxidation with co-reductant acrolein, propanal, crotonaldehyde, N-butyl aldehyde and isobutyl aldehyde respectively. And the optimal reaction path was determined to be free radical addition of peroxy acyl and propylene through analysis and comparison. In addition, the conclusion that auto-oxidation process of aldehydes and the decarboxylation in the reaction process have a certain influence on the epoxidation reaction can be conducted, and the results are in good consistent with the experimental data. It has a certain guiding effect on the choosing of co-reducing aldehydes.
- theoretical calculation,
- propylene epoxidation,
- co-reductant
1. [1]
  Nijhuis, T. A.; Makkee, M.; Moulijn, J. A.; Weckhuysen, B. M. Ind. Eng. Chem. Res. 2006, 45, 3447. doi: 10.1021/ie0513090
2. [2]
  Russo, V.; Tesser, R.; Santacesaria, E.; Di Serio, M. Ind. Eng. Chem. Res. 2013, 52, 1168. doi: 10.1021/ie3023862
3. [3]
  Chowdhury, B.; Bravo-Suárez, J. J.; Daté, M.; Tsubota, S.; Haruta, M. Angew. Chem., Int. Ed. 2006, 45, 412. doi: 10.1002/anie.200502382
4. [4]
  Du, M.; Huang, J.; Sun, D.; Li, Q. Appl. Surf. Sci. 2016, 366, 292. doi: 10.1016/j.apsusc.2016.01.086
5. [5]
  Hikazudani, S.; Mochida, T.; Yano, K.; Nagaoka, K.; Ishihara, T.; Takita, Y. Catal. Commun. 2011, 12, 1396. doi: 10.1016/j.catcom.2011.05.020
6. [6]
  Chen, J.; Halin, S. J. A.; Schouten, J. C.; Nijhuis, T. A. Faraday Discuss. 2011, 152, 321. doi: 10.1039/c1fd00014d
7. [7]
  Sun, C.; Hu, B.; Liu, Z. Chem. Eng. J. 2013, 232, 96. doi: 10.1016/j.cej.2013.07.067
8. [8]
  Zhou, X.; Ji, H. Chem. Eng. J. 2010, 156, 411. doi: 10.1016/j.cej.2009.10.066
9. [9]
  Li, Y.; Zhou, X.; Chen, S.; Luo, R.; Jiang, J.; Liang, Z.; Ji, H. RSC Adv. 2015, 5, 30014. doi: 10.1039/C4RA15601C
10. [10]
  Brown, J. W.; Nguyen, Q. T.; Otto, T.; Jarenwattananon, N. N.; Glöggler, S.; Bouchard, L. S. Catal. Commun. 2015, 59, 50. doi: 10.1016/j.catcom.2014.09.040
11. [11]
  Chen, L.; Yang, Y.; Guo, Z.; Jiang, D. Adv. Mater. 2011, 23, 3149 doi: 10.1002/adma.201100974
12. [12]
  Qi, L.; Wang, T.; Wei, Y.; Tian, H. Eur. J. Org. Chem. 2018, 2018, 6557. doi: 10.1002/ejoc.201801233
13. [13]
  Koerner, T.; Slebocka-Tilk, H.; Brown, R. S. J. Org. Chem. 1999, 64, 196. doi: 10.1021/jo981652x
14. [14]
  Bawn, C. E. H.; Williamson, J. B. Trans. Faraday Soc. 1951, 47, 735. doi: 10.1039/TF9514700735
15. [15]
  Bawn, C. E. H.; Hobin, T. P.; Raphael, L. Proc. R. Soc. A Math. Phys. Eng. Sci. 1956, 237, 313.
16. [16]
  Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A. Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision C.01, Gaussian, Inc., Wallingford CT, 2010.
17. [17]
  Sun, Z.; She, Y.; Zhong, R. Front. Chem. Eng. China 2009, 3, 457. doi: 10.1007/s11705-009-0169-6
18. [18]
  Becke, A. D. J. Chem. Phys. 1993, 98, 5648. doi: 10.1063/1.464913
19. [19]
  Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785. doi: 10.1103/PhysRevB.37.785
20. [20]
  Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735. doi: 10.1063/1.449486
21. [21]
  Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104. doi: 10.1063/1.3382344
22. [22]
  Weigend, F.; Ahlrichs, R.; Gmbh, F. K. Phys. Chem. Chem. Phys. 2005, 7, 3297. doi: 10.1039/b508541a
23. [23]
  Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378. doi: 10.1021/jp810292n
24. [24]
  Ho, J.; Klamt, A.; Coote, M. L. J. Phys. Chem. A 2010, 114, 13442. doi: 10.1021/jp107136j
25. [25]
  Merrick, J. P.; Moran, D.; Radom, L. J. Phys. Chem. A 2007, 111, 11683. doi: 10.1021/jp073974n
1. [1]
  Lubing Qin , Fang Sun , Meiyin Li , Hao Fan , Likai Wang , Qing Tang , Chundong Wang , Zhenghua Tang . 原子精确的(AgPd)₂₇团簇用于硝酸盐电还原制氨：一种配体诱导策略来调控金属核. Acta Physico-Chimica Sinica, 2025, 41(1): 2403008-. doi: 10.3866/PKU.WHXB202403008
2. [2]
  Zhenming Xu , Mingbo Zheng , Zhenhui Liu , Duo Chen , Qingsheng Liu . Experimental Design of Project-Driven Teaching in Computational Materials Science: First-Principles Calculations of the LiFePO₄ Cathode Material for Lithium-Ion Batteries. University Chemistry, 2024, 39(4): 140-148. doi: 10.3866/PKU.DXHX202307022
3. [3]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
4. [4]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-. doi: 10.3866/PKU.WHXB202408015
5. [5]
  Ji-Quan Liu , Huilin Guo , Ying Yang , Xiaohui Guo . Calculation and Discussion of Electrode Potentials in Redox Reactions of Water. University Chemistry, 2024, 39(8): 351-358. doi: 10.3866/PKU.DXHX202401031
6. [6]
  Jie ZHAO , Huili ZHANG , Xiaoqing LU , Zhaojie WANG . Theoretical calculations of CO₂ capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213
7. [7]
  Hua Hou , Baoshan Wang . Course Ideology and Politics Education in Theoretical and Computational Chemistry. University Chemistry, 2024, 39(2): 307-313. doi: 10.3866/PKU.DXHX202309045
8. [8]
  Kaifu Zhang , Shan Gao , Bin Yang . Application of Theoretical Calculation with Fun Practice in Raman Spectroscopy Experimental Teaching. University Chemistry, 2025, 40(3): 62-67. doi: 10.12461/PKU.DXHX202404045
9. [9]
  Qian Peng , Pengfei Yao , Zicong Wang , Xiufang Xu , Hongwei Sun . Promote the Training of Top Talents by Optimizing the Theoretical Computational Chemistry Curriculum System. University Chemistry, 2025, 40(5): 261-267. doi: 10.12461/PKU.DXHX202408012
10. [10]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
11. [11]
  Keweiyang Zhang , Zihan Fan , Liyuan Xiao , Haitao Long , Jing Jing . Unveiling Crystal Field Theory: Preparation, Characterization, and Performance Assessment of Nickel Macrocyclic Complexes. University Chemistry, 2024, 39(5): 163-171. doi: 10.3866/PKU.DXHX202310084
12. [12]
  Fei Xie , Chengcheng Yuan , Haiyan Tan , Alireza Z. Moshfegh , Bicheng Zhu , Jiaguo Yu . d带中心调控过渡金属单原子负载COF吸附O₂的理论计算研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2407013-. doi: 10.3866/PKU.WHXB202407013
13. [13]
  Hui Li , Jia Nie , Zhongyuan Lü , Hujun Qian , Youliang Zhu , Fuquan Bai , Zexing Qu , Ronglin Zhong . Developing a Lecture Mode for Theoretical and Computational Chemistry Curriculum under the “Modernization of Chinese Education” Initiative. University Chemistry, 2025, 40(3): 1-9. doi: 10.3866/PKU.DXHX202402007
14. [14]
  Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201
15. [15]
  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
16. [16]
  Junke LIU , Kungui ZHENG , Wenjing SUN , Gaoyang BAI , Guodong BAI , Zuwei YIN , Yao ZHOU , Juntao LI . Preparation of modified high-nickel layered cathode with LiAlO₂/cyclopolyacrylonitrile dual-functional coating. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1461-1473. doi: 10.11862/CJIC.20240189
17. [17]
  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
18. [18]
  Tao Wen , Tao Zhang , Changguo Sun , Jinyu Liu . Preparation of Dess-Martin Reagent and Its Application in Oxidizing Cyclohexanol. University Chemistry, 2024, 39(5): 20-26. doi: 10.3866/PKU.DXHX202309055
19. [19]
  Yiying Yang , Dongju Zhang . Elucidating the Concepts of Thermodynamic Control and Kinetic Control in Chemical Reactions through Theoretical Chemistry Calculations: A Computational Chemistry Experiment on the Diels-Alder Reaction. University Chemistry, 2024, 39(3): 327-335. doi: 10.3866/PKU.DXHX202309074
20. [20]
  Yunting Shang , Yue Dai , Jianxin Zhang , Nan Zhu , Yan Su . Something about RGO (Reduced Graphene Oxide). University Chemistry, 2024, 39(9): 273-278. doi: 10.3866/PKU.DXHX202306050

Get Citation

PDF

XML

Metrics

PDF Downloads(19)
Abstract views(1751)
HTML views(340)

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