Synthesis of Pd(C4H2O4)(C4H8N2)0.5 Complex and the Catalytic Activity for Oxidative Carbonylation of Phenol

›› 2008, Vol. 16 ›› Issue (3): 354-356.

• SPECIAL ISSUE OF THE FIRST INTERNATIONAL SYMPOSIUM ON SUSTAINABLE CHEMICAL PRODUCT AND PROCESS ENGINEERING • Previous Articles Next Articles

Synthesis of Pd(C₄H₂O₄)(C₄H₈N₂)_0.5 Complex and the Catalytic Activity for Oxidative Carbonylation of Phenol

CHENG Qingyan¹, LIANG Yanank¹, GAO Ling², WANG Yanji¹

1. Key Laboratory of Green Chemical Technology & High Efficient Energy Saving of Hebei Province, Hebei University of Technology, Tianjin 300130, China;
2. Tianjin Honest Industry Co. Ltd., Tianjin 300382, China

Received:2007-09-20 Revised:2008-03-30 Online:2008-06-28 Published:2008-06-28
Supported by:
Supported by the National Natural Science Foundation of China(20636030);Tianjin Natural Science Foundation(07JCZDJC00100)

Synthesis of Pd(C₄H₂O₄)(C₄H₈N₂)_0.5 Complex and the Catalytic Activity for Oxidative Carbonylation of Phenol

程庆彦¹, 梁亚男¹, 高玲², 王延吉¹

1. Key Laboratory of Green Chemical Technology & High Efficient Energy Saving of Hebei Province, Hebei University of Technology, Tianjin 300130, China;
2. Tianjin Honest Industry Co. Ltd., Tianjin 300382, China

通讯作者: CHENG Qingyan,E-mail:chengqingyan@hebut.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(20636030);Tianjin Natural Science Foundation(07JCZDJC00100)

Abstract

Abstract: A novel complex Pd(C₄H₂O₄)(C₄H₈N₂)_0.5 has been synthesized by solvent thermal synthesis and used as a heterogeneous catalyst for direct synthesis of diphenyl carbonate (DPC) by oxidative carbonylation of phenol. In the reaction system of Pd(C₄H₂O₄)(C₄H₈N₂)_0.5/Cu(OAc)₂/tetrabutylammonium bromide/hydroquinone/4A molecular sieves, the effect of reaction temperature, time and CO pressure on catalytic activity were investigated, and the results revealed that the catalyst could catalyze oxidative carbonylation of phenol effectively. Under suitable reaction conditions of T=90℃, t=4 h, p(O₂)=0.3 MPa, p(CO)=3.9 MPa and CH₂Cl₂ as solvent, the turnover number (TON) of diphenyl carbonate can reach about 13.50 (mol-DPC/mol-Pd), which is higher than the TON for pure PdCl₂ under the same reaction conditions.

Key words: diphenyl carbonate, synthesis, heterogeneous catalyst, palladium complex, oxidative carbonylation

摘要： A novel complex Pd(C₄H₂O₄)(C₄H₈N₂)_0.5 has been synthesized by solvent thermal synthesis and used as a heterogeneous catalyst for direct synthesis of diphenyl carbonate (DPC) by oxidative carbonylation of phenol. In the reaction system of Pd(C₄H₂O₄)(C₄H₈N₂)_0.5/Cu(OAc)₂/tetrabutylammonium bromide/hydroquinone/4A molecular sieves, the effect of reaction temperature, time and CO pressure on catalytic activity were investigated, and the results revealed that the catalyst could catalyze oxidative carbonylation of phenol effectively. Under suitable reaction conditions of T=90℃, t=4 h, p(O₂)=0.3 MPa, p(CO)=3.9 MPa and CH₂Cl₂ as solvent, the turnover number (TON) of diphenyl carbonate can reach about 13.50 (mol-DPC/mol-Pd), which is higher than the TON for pure PdCl₂ under the same reaction conditions.

关键词: diphenyl carbonate, synthesis, heterogeneous catalyst, palladium complex, oxidative carbonylation

CHENG Qingyan, LIANG Yanank, GAO Ling, WANG Yanji. Synthesis of Pd(C₄H₂O₄)(C₄H₈N₂)_0.5 Complex and the Catalytic Activity for Oxidative Carbonylation of Phenol[J]. , 2008, 16(3): 354-356.

程庆彦, 梁亚男, 高玲, 王延吉. Synthesis of Pd(C₄H₂O₄)(C₄H₈N₂)_0.5 Complex and the Catalytic Activity for Oxidative Carbonylation of Phenol[J]. , 2008, 16(3): 354-356.

References

1 Xue,W.,Zhang,J.C.,Wang,Y.J.,"Oxidative carbonylation of phenol to diphenyl carbonate catalyzed by ultrafine embedded catalyst Pd-Cu-O/SiO₂",Catal.Commun,6,431-436(2005).
2 Chalk,A.J.,"Fungicidal and herbicidal alpha-haloacetanilides",U.S.Pat.,4096167(1978).
3 Goyal,M.,Nagahata,R.,"Direct synthesis of diphenyl carbonate by oxidative carbonylation of phenol using Pd-Cu based redox catalyst system",J.Mol.Catal.A Chem.,137,147-154(1999).
4 Ishii,H.,Goyal,M.,"Oxidative carbonylation of phenol to diphenyl carbonate catalyzed by Pd complex with diimine ligands",Catal.Lett.,65,57-60(2000).
5 Ishii,H.,Goyal,M.,"Oxidative carbonylation of phenol to diphenyl carbonate catalyzed by Pd complex with 2,2'-bipyridyl ligands",Appl.Catal.A Gen.,201,101-105(2000).
6 Ishii,H.,Ueda,M.,"Oxidative carbonylation of phenol to diphenyl carbonate catalyzed by bis(benzonitrile) dichloropalladium in the presence of polyvinypyrrolidone",Catal.Commun.,2,17-21(2001).
7 Yasuda,H.,Watarai,K.,"Effects of bulky ligands and water in Pd-catalyzed oxidative carbonylation of phenol",J.Mol.Catal.A Chem.,236,149-155(2005).
8 Song,H.Y.,Park,E.D.,Lee,J.S.,"Oxidative carbonylation of phenol to diphenyl carbonate over supported palladium catalysts",J.Mol.Catal.A Chem.,154,243-250(2000).
9 Zhang,G.X.,Wu,Y.X.,Wu,Y.X.,Ma,P.S.,Tian,Q.F.,Wu,G.W.,Li,D.H.,Wang,C.W.,"Study on direct synthesis of diphenyl carbonate with heterogeneous catalytic reaction(V) Screening catalysts and optimizing synthesis conditions",Chin.J.Chem.Eng.,11(5),526-530(2003).
10 Fan,G.Z.,Li,T.,Zhu,D.J.,"PdCl₂/organic-inorganic hybrid catalyst for oxidative carbonylation of phenol to diphenyl carbonate",Chinese J.Catal,26(8),625-627(2005).
11 Gao,L.,Cheng,Q.Y.,Liang,Y.N.,"Synthesis of PdOP coordination polymer and catalytic properties for oxidative carbonylation of phenol",In:25th CCS Congress Abstracts,China,01-P-039(2006).
12 Liu,H.W.,"Study on the synthesis of diphenyl carbonate by oxidative carbonylation of phenol",M.S.Thesis,Hebei University of Technology,Tianjin,China(2002).(in Chinese)
13 Liu,G.,Ma,X.M.,"Study on the synthesis of diphenyl carbonate and the catalytic system",Natural Gas and Oil,19(4),18-20(2001).(in Chinese)

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Synthesis of Pd(C₄H₂O₄)(C₄H₈N₂)_0.5 Complex and the Catalytic Activity for Oxidative Carbonylation of Phenol

Synthesis of Pd(C₄H₂O₄)(C₄H₈N₂)_0.5 Complex and the Catalytic Activity for Oxidative Carbonylation of Phenol

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