钯催化苯酚氧化羰基化合成碳酸二苯酯反应机理的研究进展

催化学报 , 2008, 29(5): 489-496.

钯催化苯酚氧化羰基化合成碳酸二苯酯反应机理的研究进展

刘敏 ^1, , 吴元欣 ^2, , 杜治平 ^3, , 袁华 ^4, , 戈军伟 ^5,

1.武汉工程大学化工与制药学院,湖北省新型反应器与绿色化学工艺重点实验室,湖北武汉,430073

2.武汉工程大学化工与制药学院,湖北省新型反应器与绿色化学工艺重点实验室,湖北武汉,430073

3.武汉工程大学化工与制药学院,湖北省新型反应器与绿色化学工艺重点实验室,湖北武汉,430073

4.武汉工程大学化工与制药学院,湖北省新型反应器与绿色化学工艺重点实验室,湖北武汉,430073

5.武汉工程大学化工与制药学院,湖北省新型反应器与绿色化学工艺重点实验室,湖北武汉,430073

基金项目: 国家自然科学基金(20476083)

关键词：苯酚 , 氧化羰基化 , 碳酸二苯酯 , 钯 , 催化剂 , 反应机理

Research Advances in Reaction Mechanism for Pd-Catalyzed Oxidative Carbonylation of Phenol to Diphenyl Carbonate

综述了Pd2+催化苯酚氧化羰基化合成碳酸二苯酯反应机理的最新研究进展,详细介绍了对催化机理的验证和如何实现Pd催化体系的高效循环. 苯酚氧化羰基化合成碳酸二苯酯催化机理的研究表明,碳酸二苯酯是通过CO对 Pd - O 键的插入和中间体Pd(COOPh)(OPh)的还原消除而生成的. 在Pd催化剂体系中引入配体和氧化还原助剂,能防止Pd0的聚集,提高Pd0再生为活性Pd2+的速率,加速催化循环. 分析总结了Pd催化剂体系目前存在的问题,并提出了催化剂体系的研究方向.

参考文献

[1]	王越,魏晓魏,梅花,王公应.聚碳酸酯及其中间体的清洁生产工艺[J].合成化学,2001(06):483-489.
[2]	Gong JL;Ma XB;Wang SP .Phosgene-free approaches to catalytic synthesis of diphenyl carbonate and its intermediates[J].Applied Catalysis, A. General: An International Journal Devoted to Catalytic Science and Its Applications,2007(1):1-21.
[3]	吴广文,吴元欣,马沛生,杨小俊,金放,宣爱国.Pd-Cu/La0.5Pb0.5MnO3催化合成碳酸二苯酯的宏观动力学研究[J].燃料化学学报,2007(04):509-512.
[4]	Yoshio O .[J].Catalysis Today,1997,35(1-2):15.
[5]	王庶,梅付名,李光兴,朱志刚,代庆伟.氧化羰化法直接合成双酚A型聚碳酸酯[J].合成化学,2004(01):73-76,88.
[6]	碳酸二苯酯清洁生产技术研究开发[J].中国科技成果,2006(16):60.
[7]	范国枝,李志强,黄娇,李涛,李光兴.PdCl2/O-MCM-41催化剂制备及其在苯酚氧化羰化反应中的应用[J].无机化学学报,2006(09):1701-1705.
[8]	范国枝,李涛,朱大建,李光兴.有机-无机杂化材料负载钯催化苯酚氧化羰化合成碳酸二苯酯[J].催化学报,2005(08):625-627.
[9]	梅付名,梅慧,李光兴.羰基化法合成氨基甲酸酯催化剂的研究进展[J].现代化工,2006(08):14-18.
[10]	Hallgren J E;Matthews R O .[J].Journal of Organometallic Chemistry,1979,175(01):135.
[11]	Hallgren J E;Lucas G M;Matthews R O .[J].Journal of Organometallic Chemistry,1981,204(01):135.
[12]	Hallgren J E;Lucas G M .[J].Journal of Organometallic Chemistry,1981,212(01):135.
[13]	Joyce R P;King J A Jr;Pressman E J .[P].US 5231210,1993.
[14]	Iwane H;Miyagi H;Imada S;Seo S,Yoneyama T .[P].US 5543547,1996.
[15]	Moiseev I I;Vargaftik M N;Chernysheva T V;Stromnova T A,Gekhman A E,Tsirkov G A,Makhlina A M .[J].Journal of Molecular Catalysis A:Chemical,1996,108(02):77.
[16]	Chalk A J;Magennis S A .[P].US 4070374,1978.
[17]	Buysch H;Hesse C;Jentsch J;Rechner J,Zirngiebl E .[P].US 6001768,1999.
[18]	Goyal M;Nagahata R;Sugiyama J-I;Asai M Ueda M Takeuchi K .[J].Journal of Molecular Catalysis A:Chemical,1999,137(1-3):147.
[19]	Vavasori A.;Toniolo L. .The promoting effect of chelating ligands in the oxidative carbonylation of phenol to diphenyl carbonate catalyzed by Pd-Co-benzoquinone system[J].Journal of molecular catalysis, A. Chemical,2000(1/2):37-45.
[20]	Ishii H;Ueda M;Takeuchi K;Asai M .[J].Catalysis Communications,2001,2(01):17.
[21]	Ishii H;Takeuchi K;Asai M;Ueda M .[J].Catalysis Communications,2001,2(3-4):145.
[22]	Ishii H;Ueda M;Takeuchi K;Asai M .[J].Journal of Molecular Catalysis A:Chemical,1999,138(2-3):311.
[23]	Ishii H;Ueda M;Takeuchi K;Asai M .[J].Journal of Molecular Catalysis A:Chemical,1999,144(02):369.
[24]	Ishii H;Goyal M;Ueda M;Takeuchi K Asai M .[J].Journal of Molecular Catalysis A:Chemical,1999,148(1-2):289.
[25]	Ishii H;Ueda M;Takeuchi K;Asai M .[J].Journal of Molecular Catalysis A:Chemical,1999,144(03):477.
[26]	Ishii H;Goyal M;Ueda M;Takeuchi K Asai M .[J].Applied Catalysis A:General,2000,201(01):101.
[27]	Yasuda H.;Choi JC.;Lee SC.;Sakakura T. .Reactivity of diaryloxy palladium complex with TMEDA (N,N,N ' N '-tetramethylethylenediamine) ligand toward carbon monoxide and carbon dioxide[J].Organometallics,2002(6):1216-1220.
[28]	Yasuda H.;Maki N.;Choi JC.;Sakakura T. .Synthesis and reactivity of phenoxycarbonyl palladium complex: relevant to the mechanism of oxidative carbonylation of phenol[J].Journal of Organometallic Chemistry,2003(1/2):66-72.
[29]	Cavinato G;Toniolo L .[J].Journal of Organometallic Chemistry,1993,444(1-2):C65.
[30]	Yasuda H;Watarai K;Choi J-C;Sakakura T .[J].Journal of Molecular Catalysis A:Chemical,2005,236(1-2):149.
[31]	Spivack J L;Cawse J N;Whisenhunt D W;Johnson B F Shalyaev K V Male J Pressman E J Ofori J Y Soloveichik G L Patel B P Chuck T L Smith D J Jordan T M Brennan M R Kilmer R J Williams E D .[J].Applied Catalysis A:General,2003,254(01):5.
[32]	Schilt A A;Smith G F .[J].Journal of Physical Chemistry,1956,60(11):1546.
[33]	Charton M .[J].Journal of Organic Chemistry,1966,31(11):3739.
[34]	Schilt A A;Dunbar W E .[J].Tetrahedron,1974,30(03):401.
[35]	Okuyama K;Sugiyama J;Nagahata R;Asai M Ueda M Takeuchi K .[J].Green Chemistry,2003,5(05):563.
[36]	Okuyama K;Sugiyama J;Nagahata R;Asai M Ueda M Takeuchi K .[J].Journal of Molecular Catalysis A:Chemical,2003,203(1-2):21.
[37]	张光旭 .非均相氧化羰基化法一步合成碳酸二苯酯的基础研究[D].天津大学,2003.
[38]	Toshima N;Takahashi T .[J].Bulletin of the Chemical Society of Japan,1992,65(02):400.
[39]	Goyal M.;Sugiyama J.;Asai M.;Ueda M.;Takeuchi K.;Nagahata R. .Effect of inorganic redox cocatalyst on Pd-catalyzed oxidative carbonylation of phenol for direct synthesis of diphenyl carbonate[J].Catalysis Letters,1998(1/2):29-31.
[40]	Vavasori A;Toniolo L .[J].Journal of Molecular Catalysis A:Chemical,1999,139(2-3):109.
[41]	Yin G Ch;Jia Ch G;Kitamura T;Yamaji T Fujiwara Y .[J].Catalysis Letters,2000,69(1-2):89.
[42]	Yin G Ch;Jia Ch G;Kitamura T;Yamaji T Fujiwara Y .[J].Journal of Organometallic Chemistry,2001,630(01):11.
[43]	Hatanaka I.;Mitsuyasu N.;Yin G.;Fujiwara Y.;Kitamura T.;Kusakabe K. Yamaji T. .The mechanic study of the Pd-catalyzed synthesis of diphenylcarbonate with heteropolyacid as a cocatalyst[J].Journal of Organometallic Chemistry,2003(1/2):96-100.
[44]	张光旭,吴元欣,马沛生,吴广文,李定或.非均相催化一步合成碳酸二苯酯的研究Ⅷ.Ce和Sn的添加量对Pd/La0.62Pb0.38MnO3催化剂性能的影响[J].天然气化工,2004(04):33-37.
[45]	吴广文,吴元欣,马沛生,金放,张光旭,李定或,王存文.掺杂钙钛矿载体制备及合成碳酸二苯酯活性评价[J].天津大学学报,2006(04):385-390.
[46]	Hallgren J E .[P].US 4201721,1980.
[47]	Chin-The C T .[P].EP 0350697,1990.
[48]	Kezuka H;Okuda F .[P].EP 0508340,1992.
[49]	Iwane H;Miyagi H;Imada S;Seo S,Yoneyama T .[P].EP 0614876,1994.

上一张下一张

计量

下载量()
访问量()

作者相关

文章评分

您的评分：
1

0%
2

0%
3

0%
4

0%
5

0%

材料期刊网