Effect of solvents on propylene epoxidation over TS-1 catalyst

Abstract

Solvents have an important effect on the epoxidation of propylene catalyzed by TS-1. The experimental results show that, in different solvents, the catalytic activity of epoxidation is in the following order: methanol > 2-propanol > 2-butanol > acetonitrile > acetone > tetrahydrofuran. Based on the reaction mechanism, the effects of solvents on the epoxidation were studied from eight aspects, which included the electronic effect, the steric effect, the polarity of solvent, the effect of solvent on sorption and diffusion of reactant, the oxidation of alcohol, the etherification of PO, the deactivation of TS-1 and the solubility of propylene in the solvents. The electronic effect, steric effect and the polarity of solvent were considered to be the main aspects. This work may provide theoretical guidance for choosing solvents for these kinds of reactions and also may serve as basis for further industrialization.

References

1. Wu Yulong. Wang Chunyan. Zhang Xiangwen. Mi Zhentao. Studyprogress in integrated process of epoxidation of propylene catalyzedby TS-1 and production of H₂O₂Chemistry Online2000(13)00108(in Chinese)
2. Liu Xuewu. Wang Xiangsheng. Guo Xinwen. Li Gang. Effect of solventon the propylene epoxidation over TS-1 catalystCatalysis Today 2004 (93–95)505509
3. Su Quansheng. Wang Biao. Zhang Yumei. Wang Huaping. Effectsof the water in mixed solvent on the epoxidation reaction of propylenewith TS-1 Catalyst. Journal of Dong Hua University (Eng. Ed.) 2001 18(4)7073
4. Clerici M G Therole of the solvent in TS-1 chemistry: active or passive? An earlystudy revisited. Topics in Catalysis 2001 15(2–4)257263
5. Rafael van Grieken. David P Serrano, Juan Antonio Melero,Alicia Garcıa. Effect of the solvent in the liquid phase rearrangementof 1,2-epoxyoctane over Al-MCM-41 and Al-TS-1 catalysts. Journal of Molecular Catalysis A: Chemical 2004 222167174
6. Clerici M G Ingallina P1 Epoxidation of lower olefinswith hydrogen peroxide. titanium silicalite. J Catal 1993 140(1)7183
7. V. Arca,A. Boscolo Boscoletto, N. Fracasso, L. Medab, G. Ranghino.Epoxidationof propylene on Zn-treated TS-1 catalyst. Journal of Molecular Catalysis A: Chemical 2006 243264277
8. Jan C vander Waal, Herman van Bekkum. Zeolite titanium beta: A versatile epoxidationcatalyst Solvent effects. Journal of MolecularCatalysis A: Chemical 1997 124137146
9. Wang Jitao. Hu Qingmei. Zhang Baoshen. Organic Chemistry. Tianjin: Nankai University Press, 1993. 258
10. Wu P Komatsu T Yashima T Hydroxylation of aromatics with hydrogen peroxide overtitanosilicates with MOR and MFI structure: effect of ti peroxo specieson the diffusion and hydroxylation activityJ Phys Chem B 1998 10292979303
11. Christian Reichardt. Empiricalparameters of solvent polarity as linear free-energy relationships.Angew Chem lnt Ed Engl. 1979 1898110
12. Vasile Hulea. Patrice Moreau. The solvent effect in the sulfoxidationof thioethers by hydrogen peroxide using Ti-containing zeolites ascatalystsJournal of Molecular CatalysisA: Chemical 1996 113499505
13. Reichardt C Solventeffects in organic chemistryNew York: VerlagChemie Weinheim 1979 5–7
14. Gunther Langhendries. Dirk E De Vos. et al.Quantitative sorption experiments on Ti-Zeolitesand relation with α-olefin oxidation by H₂O₂J Catal 1999 187453463
15. Wu Yulong. Mi Zhentao. Chen Junxia. Su Xueli. Li Wei. Study on oxidation of alcohol solventsin epoxidation of propylene catalyzed by TS-1Chemical Reaction Engineering and Technology 2004 20(1)914(in Chinese)
16. Corma A Esteve P Martinez A Valencia S Oxidation ofolefins with hydrogen peroxide and tert-butyl hydroperoxide on Ti-betacatalystJournal of Catalysis 1995 1521824
17. Wu Yulong. Mi Zhentao. Chen Junxia. Li Wei. Study on ringopening of propylene oxide in epoxidation of propylene catalyzed byTS-1Journal of Fuel Chemistry and Technology 2003 131(12)161166(in Chinese)
18. Yan Haisheng. Wang Xiangsheng. Liu Jing. Guo X i n w e n Studyon the TS-1 deactivation during propylene epoxidation. Acta Petrol.Ei. Sinica. (Petroleum processing section) 2002 18(1)4651(in Chinese)
19. Wang Qingfa. Wang Li. Chen Junxia. Wu Yulong. Mi Zhentao. Deactivation and regenerationof titanium silicalite catalyst for epoxidation of propyleneJournal of Molecular Catalysis A: Chemical 2007 2737380
20. Wu Yulong. Mi Zhentao. Ren Yongli. et al.Solubility of propylene in alcohol solutionChemical Engineering (China) 2006, 34(1): 40–4354(in Chinese)