Effect of Doping Cerium in the Support of Catalyst Pd-Co/Cu-Co-Mn Mixed Oxides on the Oxidative Carbonylation of Phenol

Abstract

Abstract: Effect of doping cerium in the support on the catalytic activity and side product of the reaction in the oxidative carbonylation of phenol to diphenyl carbonate (DPC) over the catalyst Pd-Co/Cu-Co-Mn mixed oxides was studied. The specific surface areas, crystal phase, valency, and content of the element on the surface of the catalysts were determined, and the products were detected by gas chromatograph/mass spectrometry (GC-MS). It is found that the catalyst without Ce shows higher activity than that with Ce, and the yields of DPC for the two catalysts can reach 30% and 23%, respectively. However, doping cerium can prevent the formation of 2-hydroxyphenyl benzoate and p-bromophenyl phenyl carbonate.

Key words: diphenyl carbonate, oxidative carbonylation, doping cerium, sol-gel method

摘要： Effect of doping cerium in the support on the catalytic activity and side product of the reaction in the oxidative carbonylation of phenol to diphenyl carbonate (DPC) over the catalyst Pd-Co/Cu-Co-Mn mixed oxides was studied. The specific surface areas, crystal phase, valency, and content of the element on the surface of the catalysts were determined, and the products were detected by gas chromatograph/mass spectrometry (GC-MS). It is found that the catalyst without Ce shows higher activity than that with Ce, and the yields of DPC for the two catalysts can reach 30% and 23%, respectively. However, doping cerium can prevent the formation of 2-hydroxyphenyl benzoate and p-bromophenyl phenyl carbonate.

关键词: diphenyl carbonate, oxidative carbonylation, doping cerium, sol-gel method

LIANG Yinghua, GUO Hongxia, CHEN Hongping, LÜJingde, ZHANG Bobo. Effect of Doping Cerium in the Support of Catalyst Pd-Co/Cu-Co-Mn Mixed Oxides on the Oxidative Carbonylation of Phenol[J]. , 2009, 17(3): 401-406.

梁英华, 郭红霞, 陈红萍, 吕敬德, 张波波. Effect of Doping Cerium in the Support of Catalyst Pd-Co/Cu-Co-Mn Mixed Oxides on the Oxidative Carbonylation of Phenol[J]. , 2009, 17(3): 401-406.

References

1 Meenakshi, G., Ritsuko, N., Mitsuru, U., “Direct synthesis of diphenyl carbonate by oxidative carbonylation of phenol using Pd-Cu based redox catalyst”, J. Mol. Cat. A:Chem., 137, 147-154(1999).
2 Meenakshi, G., Ritsuko, N., Sugiyama, J., “Effect of inorganic redox cocatalyst on Pd-catalyzed for direct synthesis of diphenyl carbonate”, Cat. Lett., 54, 29-31(1998).
3 Hirotoshi, I., Mistsuru, U., Kazuhiko, T., “Oxidative carbonylation of phenol carbonate catalyzed by Pd-Sn complexes with redox catalyst”, J. Mol. Cat. A:Chem., 138, 311-313(1999).
4 Hirotoshi, I., Mistsuru, U., Kazuhiko, T., “Oxidative carbonylation of phenol carbonate catalyzed by Pd-Sn heterotrinuclear complexes along with Mn redox catalyst without any addition of ammonium halide”, J. Mol. Cat. A:Chem., 144, 369-372(1999).
5 Liu, H.W., Zhao, Q., Zhao, X.Q., “Oxidative carbonylation of phenol to diphenyl carbonate over palladium complexes catalysts”, J. Sichuan Univ. 34(1), 47-49(2002).(in Chinese)
6 Okuyama, K., Sugiyama, J., Nagahata, R., “Oxidative carbonylation of phenol to diphenyl carbonate catalyzed by palladium-carbene complexes”, J. Mol. Cat. A Chem., 203, 21-27(2003).
7 Buysch, H.J., Hess, C., Jentsch, J.D., “Supported platinum-group metal preparation of diaryl carbonates”, EP 736325(1996).
8 Buysch, H.J., Jentsch, J.D., Rechner. J., “Supported platinum catalysts and process for preparation of diary carbonates”, EP 736324(1996).
9 Hesse, C., Nothesis, U., Rechner. J., “Supported platinum-group metal for producing diaryl carbonates form carbon monoxide”, WO 9908786(1999).
10 Takagi, W., “Preparation of aromatic carbonates as materials for polycarbonates”, JP 09278716(1997).
11 Xue, W., Wang, Y.J., Zhao, X.Q., “Oxidative carbonylation of phenol to diphenyl carbonate over supported embedded catalyst Pd-Cu-O/SiO₂ prepared through W/O microemulsion method”, In:The proceedings of the 13th International Conference on Catalysis, Paris, 7, 1-321(2004).
12 Xue, W., Zhao,X.Q., Wang,Y.J., “Effect of promoter copper on the oxidative carbonylation of phenol over the ultrafine embedded catalyst Pd-Cu-O/SiO₂ ”, J. Mol. Cat. A:Chem., 232, 77-81(2005).
13 Zhang, G.X., Wu, Y.X., Ma, P.S., Wu, G.W., Li, D.H., “Study on direct synthesis of diphenyl carbonate with heterogeneous catalyzing reaction(I) Effect of method of preparing Pd catalyst carriers on catalyst activity”, Chin. J. Catal., 23(2), 130-132(2002).(in Chinese)
14 Zhang, G.X., Ma, P.S., Wu, Y.X.,Wu, G.W., Li, D.H., “Study on direct synthesis of diphenyl carbonate with heterogeneous catalyzing reaction(II) Effect of calcination temperature on catalytic activity of catalyst”, Chin. J. Fuel Chem. Tech., 30(4), 362-367(2002).(in Chinese)
15 Zhang, G.X., Wu, Y.X., Ma, P.S., Wu, G.W., Li, D.H., “Study on direct synthesis of diphenyl carbonate with heterogeneous catalyzing reaction(III) Effect of lanthanum content on catalytic activity of catalyst”, Chin. J. Mol. Catal.,16(4), 292-297(2002).(in Chinese)
16 Zhang, G.X., Wu, Y.X., Ma, P.S., Wu, G.W., Li, D.H., “Study on direct synthesis of diphenyl carbonate with heterogeneous catalyzing reaction(IV) Effect of active components and the supporting methods on catalytic activity of catalyst”, Chin. J. Mol. Catal., 23(5), 410-416(2002).(in Chinese)
17 Iwane, H., Miyagi, H., Imada, S., “Method of producing aromatic carbonate”, EP 0614876(1993).
18 Takagi, M., Miyagi, H., Yoneyama, T., “Palladium-lead catalyzed oxidative of phenol”, J. Mol. Cat. A:Chem., 129, 1-3(1998).
19 Song, H.Y., Yark, D., Lee, J.S., “Oxidative carbonylation of phenol to diphenyl carbonate over supported palladium catalysts”, J. Mo1. Cat. A:Chem., 154, 243-250(2000).
20 Zhang, G.X., Wu, Y.X., Ma, P.S., Tian, Q.F., Wu, G.W., Li, D.H., “Study on direct synthesis of diphenyl carbonate with heterogeneous catalytic reaction(VI) Effect of Sn loading method and content on activity of Sn-Pd supported catalyst”, Chin. J. Chem. Eng., 12(2), 191-195(2004).
21 Goyal, M., Nagahata, R., Sugiyama, J., “Effect of inorganic redox cocatalysts on Pd catalyzed oxidative carbonylation of phenol for direct synthesis of diphenyl carbonate”, Catal. Lett., 54(3), 29-36(1998).
22 Guo, H.X., Chen, H.P., Liang, Y.H., Rui, Y.L., Lü, J.D., Fu, Z.D., “Direct synthesis of diphenyl carbonate with heterogeneous catalyst and optimal synthesis conditions of the support prepared by sol-gel method”, Chin. J. Chem. Eng., 16(2), 223-227(2008).
23 Wu, G. W., Wu, Y.X., Ma, P.S., Jin, F., Zhang, G.X., Li, D.H., Wang, C.W., “Preparation of substitution-structure perovskite carriers and activity evaluation for synthesis of diphenyl carbonate”, J. Tianjin Univ., 39(4), 385-400(2006).
24 Bi, Y.S., Lü, G.X., “Influence of transition metal additives on CO oxidation over NaZSM-5 supported Pd”, J. Ind. Eng. Chem., 62(20), 1981-1987(2004).

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