Reaction-controlled phase-transfer catalysis for propylene epoxidation to propylene oxide

Science

Volumn 292, Issue 5519, 2001, Pages 1139-1141

  Zuwei, Xi ^a   Ning, Zhou ^a   Yu, Sun ^a   Kunlan, Li ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; OXIDATION; PHASE TRANSITIONS; PRECIPITATION (CHEMICAL); REDOX REACTIONS; TUNGSTEN;

HOMOGENEOUS CATALYSTS;

PROPYLENE;

ALKENE; ANTHRAQUINONE DERIVATIVE; HYDROGEN PEROXIDE; PROPYLENE; PROPYLENE OXIDE; TUNGSTEN;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; EPOXIDATION; OXIDATION REDUCTION REACTION; PRECIPITATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0035843980     PISSN: 00368075     EISSN: None     Source Type: Journal    
DOI: 10.1126/science.292.5519.1139     Document Type: Article

References (18)

1. M. F. Portela et al., Catal. Today 1, 101 (1987).
2. G. Z. Lu, X. B. Zuo, Catal. Lett. 58, 67 (1999).
3. M. G. Clerici, G. Bellussi, U. Romano, J. Catal. 129, 159 (1991).
4. P. Ingallina, M. G. Clerici, L. Rossi, Stud. Surf. Sci. Catal. 92, 31 (1995).
5. The diameter of the pore of TS-1 zeolite is about 0.6 nm. Linear molecules and mononuclear aromatic compounds can diffuse to TS-1 active sites and be oxidized. In order to avoid these reactions, 2-methylnaphtalene and diisobutylcarbinol, whose molecules have a cross-section diameter greater than 0.6 nm, are used as the medium. Methanol is necessary for the epoxidation of propytene catalyzed by TS-1 zeolite.
6. 2, after several cycles of the EAQ/EAHQ redox system, the degree of hydrogenation can be 75 to 80%, and the concentration of hydroquinone is 0.4 to 0.45 mol/liter. However, in (4), when the degree of hydrogenation is 100%, the concentration of hydroquinone is only about 0.13 mol/liter.
7. J. Haber, T. Mlodnicka, J. Mol. Catal. 54, 451 (1989).
8. I. Yamanaka, K. Nakagaki, K. Otsuka, J. Chem. Soc. Chem. Commun. 1995, 1185 (1995).
9. J. P. Renaud, P. Battioni, J. F. Bartoli, D. Mansuy, J. Chem. Soc. Chem. Commun. 1985, 888 (1985).
10. C. Venturello, R. D'Aloisio, J. Org. Chem. 53, 1553 (1988).
11. Y. Ishii et al., J. Org. Chem. 53, 3587 (1988).
12. C. Venturello, E. Alneri, M. Ricci, J. Org. Chem. 48, 3831 (1983).
13. 2 and 0.05 mmol of catalyst I were then added. The reaction was conducted at 35°C and was terminated after the catalyst precipitated.
14. 6: EAHQ = 2.7: 1 (molar ratio)] was fed into the autoclave. The reaction was maintained at 65°C for 6 hours. After the reaction, the autoclave was cooled to 23°C. The gas in it was discharged, and the propylene and propylene oxide in the gas were analyzed by gas chromatography (GC) with the external standard method. The propylene and propylene oxide in the liquid were analyzed by GC with the internal standard method.
15. C. Venturello, R. D'Aloisio, J. C. J. Bart, M. Ricci, J. Mol. Catal. 32, 107 (1985).
16. 4}: O (active) = 3.20%.
17. C. Rocchiccioli-Deltcheff, M. Fournier, R. Franck, R. Thouvenot, Inorg. Chem. 22, 207(1983).
18. We are grateful to C. Zhang and X. Huang for their support of this research and to L. Lin for his valuable discussions. This work was financially supported by the National Nature Science Foundation of China (grant no. 29673042).