Liquid-phase epoxidation of propylene with molecular oxygen by chloride manganese meso-tetraphenylporphyrins

doi:10.1016/j.cjche.2021.08.006

中国化学工程学报 ›› 2022, Vol. 48 ›› Issue (8): 61-65.DOI: 10.1016/j.cjche.2021.08.006

Liquid-phase epoxidation of propylene with molecular oxygen by chloride manganese meso-tetraphenylporphyrins

Xian-Tai Zhou¹, Ling-Ling Wang¹, Yang Li², Hong-Bing Ji^2,3

1. Fine Chemical Industry Research Institute, School of Chemical Engineering and Technology, Sun Yat-sen University, Zhuhai 519082, China;
2. Fine Chemical Industry Research Institute, School of Chemistry, Sun Yat-sen University, Guangzhou 510275, China;
3. School of Chemical Engineering, Guangdong University of Petrochemical Technology, Maoming 525000, China

收稿日期:2021-06-07 修回日期:2021-08-07 出版日期:2022-08-28 发布日期:2022-09-30
通讯作者: Hong-Bing Ji,E-mail:jihb@mail.sysu.edu.cn
基金资助:
This work was financially supported by the National Key Research and Development Program of China (2020YFA0210900), the National Natural Science Foundation of China (No. 21938001 and 21878344), Research and Innovation Team Construction Project of Guangdong University of Petrochemical Technology.

Liquid-phase epoxidation of propylene with molecular oxygen by chloride manganese meso-tetraphenylporphyrins

Xian-Tai Zhou¹, Ling-Ling Wang¹, Yang Li², Hong-Bing Ji^2,3

1. Fine Chemical Industry Research Institute, School of Chemical Engineering and Technology, Sun Yat-sen University, Zhuhai 519082, China;
2. Fine Chemical Industry Research Institute, School of Chemistry, Sun Yat-sen University, Guangzhou 510275, China;
3. School of Chemical Engineering, Guangdong University of Petrochemical Technology, Maoming 525000, China

Received:2021-06-07 Revised:2021-08-07 Online:2022-08-28 Published:2022-09-30
Contact: Hong-Bing Ji,E-mail:jihb@mail.sysu.edu.cn
Supported by:
This work was financially supported by the National Key Research and Development Program of China (2020YFA0210900), the National Natural Science Foundation of China (No. 21938001 and 21878344), Research and Innovation Team Construction Project of Guangdong University of Petrochemical Technology.

摘要/Abstract

摘要： Propylene molecule owns two active sites, the direct epoxidation of propylene by dioxygen is still a challenge due to the limitation of selectivity. In this work, the direct liquid-phase propylene aerobic epoxidation protocol by chloride manganese meso-tetraphenylporphyrin (MnTPPCl) was developed. The conversion of propylene was 12.7%, and the selectivity towards PO (propylene oxide) reached up to 80.5%. The formation of PO was attributed to the mechanism via high-valent Mn species, which was confirmed by means of in situ UV–vis spectrum.

关键词: Propylene, Epoxidation, Dioxygen, Manganese porphyrins, Liquid phase

Abstract: Propylene molecule owns two active sites, the direct epoxidation of propylene by dioxygen is still a challenge due to the limitation of selectivity. In this work, the direct liquid-phase propylene aerobic epoxidation protocol by chloride manganese meso-tetraphenylporphyrin (MnTPPCl) was developed. The conversion of propylene was 12.7%, and the selectivity towards PO (propylene oxide) reached up to 80.5%. The formation of PO was attributed to the mechanism via high-valent Mn species, which was confirmed by means of in situ UV–vis spectrum.

Key words: Propylene, Epoxidation, Dioxygen, Manganese porphyrins, Liquid phase

Xian-Tai Zhou, Ling-Ling Wang, Yang Li, Hong-Bing Ji. Liquid-phase epoxidation of propylene with molecular oxygen by chloride manganese meso-tetraphenylporphyrins[J]. 中国化学工程学报, 2022, 48(8): 61-65.

参考文献

[1] Marimuthu, J.W. Zhang, S. Linic, Tuning selectivity in propylene epoxidation by plasmon mediated photo-switching of Cu oxidation state, Science 339 (2013) 1590-1593
[2] G.I. Panov, E.V. Starokon, M.V. Parfenov, L.V. Pirutko, Single turnover epoxidation of propylene by α-Complexes (FeIII-O?)α on the surface of FeZSM-5 zeolite, ACS Catal. 6 (2016) 3875-3879
[3] X.F. Yang, S. Kattel, K. Xiong, K. Mudiyanselage, S. Rykov, S.D. Senanayake, J.A. Rodriguez, P. Liu, D.J. Stacchiola, J.G. Chen, Direct epoxidation of propylene over stabilized Cu+ surface sites on titanium-modified Cu2O, Angew Chem. Int. Ed. 54 (2015) 11946-11951
[4] Q.R. Zhu, C.L. Miao, Y.H. Yi, C.Y. Liu, Y.T. Guo, Z.C. Feng, H.C. Guo, Solvent-free gas-phase epoxidation of propylene in fluidized bed reactor. AIChE J. 67(2021) e17218
[5] D. Torres, N. Lopez, F. Illas, R.M. Lambert, Low-basicity oxygen atoms: A key in the search for propylene epoxidation catalysts, Angew Chem. Int. Ed. 46 (2007) 2055-2058
[6] Y.Y. Liu, K. Murata, M. Inaba, Direct epoxidation of propylene by molecular oxygen over a catalyst system containing palladium and a peroxo-heteropoly compound in methanol, Chem. Commun. (2004) 582-583
[7] J.P. Yin, X. Jin, H. Xu, Y.J. Guan, R.S. Peng, L.Chen, J.G. Jiang, P. Wu, Structured binder-free MWW-type titanosilicate with Si-rich shell for selective and durable propylene epoxidation. Chin. J. Catal. 42 (9) (2021) 1561-1575
[8] X.L. Ni, J. Liu, Y.Y. Liu, K. Leus, H. Depauw, A.J. Wang, P. Van Der Voort, J. Zhang, Y.K. Hu, Synthesis, characterization and catalytic performance of Mo based metal- organic frameworks in the epoxidation of propylene by cumene hydroperoxide, Chin. Chem. Lett. 28 (2017) 1057-1061
[9] I.D. Charisteidis, K.S. Triantafyllidis, Propylene epoxidation by molecular oxygen using supported silver catalysts: Effect of support type, preparation method and promotion with alkali chloride and/or steam. Catal. Today 355(2020) 654-664
[10] J. Garcia-Aguilar, I. Miguel-Garcia, J. Juan-Juan, I. Such-Basanez, E.S. Fabian, D. Cazorla-Amoros, A. Berenguer-Murcia, One step-synthesis of highly dispersed iron species into silica for propylene epoxidation with dioxygen, J. Catal. 338 (2016) 154-167
[11] J. Garcia-Aguilar, D. Cazorla-Amoros, A. Berenguer-Murcia, K- and Ca-promoted ferrosilicates for the gas-phase epoxidation of propylene with O2, Appl. Catal. A, 538 (2017) 139-147
[12] J. Terzan, M. Hus, B. Likozar, P. Djinovic, Propylene epoxidation using molecular oxygen over copper- and silver-based catalysts: A review. ACS Catal. 10(2020) 13415-13436
[13] Y. Lei, F. Mehmood, S. Lee, J. Greeley, B. Lee, S. Seifert, R.E. Winans, J.W. Elam, R.J. Meyer, P.C. Redfern, D. Teschner, R. Schlogl, M.J. Pellin, L.A. Curtiss, S. Vajda, Increased silver activity for direct propylene epoxidation via subnanometer size effects, Science 328 (2010) 224-228
[14] Q. Zhang, Y.L. Guo, W.C. Zhan, Y. Guo, L. Wang, Y.S. Wang, G.Z. Lu, Gas-phase epoxidation of propylene by molecular oxygen over Ag/BaCO3 catalysts: Effect of preparation conditions, Catal. Today 276 (2016) 2-10
[15] L. Cheng, C.R. Yin, F. Mehmood, B. Liu, J. Greeley, S. Lee, B. Lee, S. Seifert, R.E. Winans, D. Teschner, R. Schlogl, S. Vajda, L.A. Curtiss, Reaction mechanism for direct propylene epoxidation by alumina-supported silver aggregates: The role of the particle/support interface, ACS Catal. 4 (2014) 32-39
[16] W.S. Lee, R. Zhang, M.C. Akatay, C.D. Baertsch, E.A. Stach, F.H. Ribeiro, W.N. Delgass, Differences in catalytic sites for CO oxidation and propylene epoxidation on Au nanoparticles, ACS Catal. 1 (2011) 1327-1330
[17] S.N. Yao, L.H. Xu, J. Wang, X.L. Jing, T. Odoom-Wubah, D.H. Sun, J.L. Huang, Q.B. Li, Activity and stability of titanosilicate supported Au catalyst for propylene epoxidation with H-2 and O-2, Mol. Catal. 448 (2018) 144-152
[18] X.N. Lu, G.F. Zhao, Y. Lu, Propylene epoxidation with O2 and H2: a high-performance Au/TS-1 catalyst prepared via a deposition-precipitation method using urea, Catal. Sci. Technol. 3 (2013) 2906-2909
[19] W.M. Zhu, Q.H. Zhang, Y. Wang, Cu(I)-catalyzed epoxidation of propylene by molecular oxygen, J. Phys. Chem. C 112 (2008) 7731-7734
[20] A. Seubsai, M. Kahn, B. Zohour, D. Noon, M. Charoenpanich, S. Senkan, Copper-manganese mixed metal oxide catalysts for the direct epoxidation of propylene by molecular oxygen, Ind. Eng. Chem. Res. 54 (2015) 2638-2645
[21] H. Chu, L. Yang, Q.H. Zhang, Y. Wang, Copper-catalyzed propylene epoxidation by molecular oxygen: Superior catalytic performances of halogen-free K+-modified CuOx/SBA-15, J. Catal. 241 (2006) 225-228
[22] B. Horvath, M. Hronec, I. Vavra, M. Sustek, Z. Krizanova, J. Derer, E. Dobrocka, Direct gas-phase epoxidation of propylene over nanostructured molybdenum oxide film catalysts, Catal. Commun. 34 (2013) 16-21
[23] Y.X. Miao, G.Z. Lu, X.H. Liu, Y.L. Guo, Y.Q. Wang, Y. Guo, Effects of preparation procedure in sol-gel method on performance of MoO3/SiO2 catalyst for liquid phase epoxidation of propylene with cumene hydroperoxide, J. Mol. Catal. A 306 (2009) 17-22
[24] Y.J. Pang, X.H. Chen, C.Z. Xu, Y.J. Lei, K.M. Wei, High Catalytic Performance of MoO3-Bi2SiO5/SiO2 for the gas-phase epoxidation of propylene by molecular oxygen, ChemCatChem, 6 (2014) 876-884
[25] N. Yap, R.P. Andres, W.N. Delgass, Yap, N.; Andres, R. P.; Delgass, W. N., Reactivity and stability of Au in and on TS-1 for epoxidation of propylene with H2 and O2, J. Catal. 226 (2004) 156-170
[26] B. Chowdhitry, J.J. Bravo-Suarez, M. Date, S. Tsubota, M. Haruta, Trimethylamine as a gas-phase promoter: Highly efficient epoxidation of propylene over supported gold catalysts, Angew Chem. Int. Ed. 45 (2006) 412-415
[27] N.X. Li, B. Yang, M. Liu, Y. Chen, J.C. Zhou, Synergetic photo-epoxidation of propylene with molecular oxygen over bimetallic Au-Ag/TS-1 photocatalysts, Chin. J. Catal. 38 (2017) 831-844
[28] X.Q. Lu, H.H. Wu, J.G. Jiang, M.Y. He, P. Wu, Selective synthesis of propylene oxide through liquid-phase epoxidation of propylene with H2O2 over formed Ti-MWW catalyst, J. Catal. 342 (2016) 173-183
[29] D.H. Wells, W.N. Delgass, K.T. Thomson, Evidence of defect-promoted reactivity for epoxidation of propylene in titanosilicate (TS-1) catalysts: A DFT study, J. Am. Chem. Soc. 126 (2004) 2956-2962
[30] W.J. Yan, Y. H. Wu, X. Feng, C.H. Yang, X. Jin, J. Shen, Selective propylene epoxidation in liquid phase using highly dispersed Nb catalysts incorporated in mesoporous silicates. Chin. J. Chem. Eng. 26 (2018)1278-1284
[31] Z.W. Xi, N. Zhou, Y. Sun, K.L. Li, Reaction-controlled phase-transfer catalysis for propylene epoxidation tea propylene oxide, Science 292(2001) 1139-1141
[32] A. Prieto, M. Palomino, U. Diaz, A. Corma, Propylene epoxidation with in situ generated H2O2 in supercritical conditions. Catal. Today 227(2014) 87-95
[33] M. Lin, C.J. Xia, B. Zhu, H. Li, X.T. Shu, Green and efficient epoxidation of propylene with hydrogen peroxide (HPPO process) catalyzed by hollow TS-1 zeolite: A 1.0 kt/a pilot-scale study, Chem. Eng. J. 295 (2016) 370-375
[34] D. den Boer, M. Li, T. Habets, P. Iavicoli, A.E. Rowan, R.J.M. Nolte, S. Speller, D.B. Amabilino, S. De Feyter, J.A.A.W. Elemans, Detection of different oxidation states of individual manganese porphyrins during their reaction with oxygen at a solid/liquid interface, Nat. Chem. 5 (2013) 621-627
[35] K.P. Shing, B. Cao, Y.G. Liu, H.K. Lee, M.D. Li, D.L. Phillips, X.Y. Chang, C.M. Che, Arylruthenium(III) porphyrin-catalyzed C-H oxidation and epoxidation at room temperature and [Ruv(Por)(O)(Ph)] intermediate by spectroscopic analysis and density functional theory calculations, J. Am. Chem. Soc. 140 (2018) 7032-7042
[36] S.Y. Chen, X.T. Zhou, H.B. Ji, Insight into the cocatalyst effect of 4A molecular sieve on Sn(II) porphyrin-catalyzed B-V oxidation of cyclohexanone, Catal.Today 264 (2016) 191-197
[37] Y. Li, X.T. Zhou, S.Y. Chen, R.C. Luo, J. Jiang, Z.X. Liang, H.B. Ji, Direct aerobic liquid phase epoxidation of propylene catalyzed by Mn(III) porphyrin under mild conditions: evidence for the existence of both peroxide and Mn(IV)-oxo species from in situ characterizations, RSC Adv. 5 (2015) 30014-30020
[38] X. T. Zhou, H. Y. Yu, Y. Li, C. Xue, H.B. Ji, Cerium(IV) sulfate as a cocatalyst for promoting the direct epoxidation of propylene by ruthenium porphyrin with molecular oxygen. Ind. Eng. Chem. Res. 59(2020), 19982-19988
[39] X.T. Zhou, H.B. Ji, Biomimetic kinetics and mechanism of cyclohexene epoxidation catalyzed by metalloporphyrins, Chem. Eng. J. 156 (2010) 411-417
[40] X.H. Liu, H.Y. Yu, C. Xue, X.T. Zhou, H.B. Ji, Cyclohexene promoted efficient biomimetic oxidation of alcohols to carbonyl compounds catalyzed by manganese porphyrin under mild conditions. Chin. J. Chem. 38(2020) 458-464
[41] H.M. Shen, B. Qi, M.Y. Hu, L. Liu, H.L. Ye, Y.B. She, Selective solvent-free and additive-free oxidation of primary benzylic C-H bonds with O2 catalyzed by the combination of metalloporphyrin with N-hydroxyphthalimide. Catal. Lett. 150 (2020) 3096-3111
[42] P. Spannring, P.C.A. Bruijnincx, B.M. Weckhuysen, R.J.M.K. Gebbink, Transition metal-catalyzed oxidative double bond cleavage of simple and bio-derived alkenes and unsaturated fatty acids, Catal. Sci. Technol. 4(2014) 2182-2209
[43] X.T. Zhou, H.B. Ji, Highly efficient oxidative cleavage of carbon-carbon double bond over meso-tetraphenyl cobalt porphyrin catalyst in the presence of molecular oxygen, Chin. J. Chem. 30(2012) 2103-2108
[44] E. Hasegawa, Y. Ogawa, K. Kakinuma, H. Tsuchida, E. Tosaka, S.Takizawa, H. Muraoka, T. Saikawa, Tris(trimethylsilyl)silane promoted radical reaction and electron-transfer reaction in benzotrifluoride. Tetrahedron 64 (2008) 7724-7728
[45] L. Bui, R. Chakrabarti, A. Bhan, Mechanistic origins of unselective oxidation products in the conversion of propylene to acrolein on Bi2Mo3O12, ACS Catal. 6 (2016) 6567-6580
[46] X.Y. Huang, J.T. Groves, Oxygen activation and radical transformations in heme proteins and metalloporphyrins, Chem. Rev. 118 (2018) 2491-2553
[47] H.Y. Chen, M. Lv, X.T. Zhou, J.X. Wang, Q. Han, H.B. Ji, A novel system comprising metalloporphyrins and cyclohexene for the biomimetic aerobic oxidation of toluene, Catal. Commun. 109 (2018) 76-79

Liquid-phase epoxidation of propylene with molecular oxygen by chloride manganese meso-tetraphenylporphyrins

Liquid-phase epoxidation of propylene with molecular oxygen by chloride manganese meso-tetraphenylporphyrins

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