研究了双膦配体对铑催化的乙酸乙烯酯氢甲酰化反应的促进作用,结果表明,在优化反应条件下,以双膦化合物2,2'-二(二苯膦甲基)-1,1'-联苯(BISBI)为配体时,铑催化乙酸乙烯酯氢甲酰化反应的TOF(转化频率)值达到4000 h-1,生成2-乙酰氧基丙醛的选择性>99%.当在较温和的条件下Rh/BISBI催化乙酸乙烯酯氢甲酰化反应较长时间时TON(转化数)值达到9200,成醛率超过90%,2-乙酰氧基丙醛选择性仍保持>99%.
Rhodium-catalyzed hydroformylation of vinyl acetate with the use of diphosphine ligands was studied.A high regioseleetivity (branched:linear of 99:1) and activity (TOF:4000 h-1) under optimum conditions were achieved by using a 2,2'-bis(diphenylphosphino methyl)-l,1 '-biphenyl ligand.The high turnover number (9200) obtained under mild conditions and stability of the catalyst indicates that it would be useful for industrial vinyl acetate hydroformylation.
参考文献
[1] | Van Leeuwen P W N M;Claver C.Rhodium Catalyzed Hydroformylation[M].Amsterdam:Kluwer Academic Publishers,2000:2. |
[2] | Saidi O;Liu S F;Xiao J L .[J].Journal of Molecular Catalysis A:Chemical,2009,305:130. |
[3] | Yu S C;Chie Y M;Zhang X M .[J].Advanced Synthesis and Catalysis,2009,351:537. |
[4] | Noonan G M;Newton D;Cobley C J;Suarez A Pizzano A Clarke M L .[J].Advanced Synthesis and Catalysis,2010,352:1047. |
[5] | Panda A G;Tambade P J;Patil Y P;Bhanage B M .[J].Reac Kinet Mech Catal,2010,99:143. |
[6] | Reynhardt, JPK;Yang, Y;Sayari, A;Alper, H .Periodic mesoporous silica-supported recyclable rhodium-complexed dendrimer catalysts[J].Chemistry of Materials,2004(21):4095-4102. |
[7] | Borole Y L;Chaudhari R V .[J].Industrial and Engineering Chemistry Research,2005,44:9601. |
[8] | Sudheesh N;Chaturvedi A K;Shukla R S .[J].Applied Catalysis A:General,2011,409-410:99. |
[9] | Abatjoglou A G;Bryant D R;D'Esposito L C .[J].Journal of Molecular Catalysis,1983,18:381. |
[10] | Williams D B G;Ajam M;Ranwell A .[J].Organometallics,2007,26:4692. |
[11] | Panda A G;Patil Y P;Tambade P J;Bhanage B M .[J].Industrial and Engineering Chemistry Research,2010,49:8360. |
[12] | Dabbawala AA;Jasra R V;Bajaj H C .[J].Catalysis Communications,2010,11:616. |
[13] | 刘雯静,袁茂林,付海燕,李瑞祥,陈华.铑/双膦配体催化均相内烯烃氢甲酰化反应的研究进展[J].催化学报,2009(06):577-586. |
[14] | 张林,李春,付海燕,袁茂林,李瑞祥,陈华.新型双膦配体的合成及其在2-丁烯氢甲酰化反应中的应用[J].催化学报,2011(02):299-302. |
[15] | Breeden S;Cole-Hamilton D J;Foster D F;Schwarz G J,Wills M .[J].Angewandte Chemie International Edition,2000,39:4106. |
[16] | Clark T P;Landis C R;Freed S L;Klosin J Abboud K A .[J].Journal of the American Chemical Society,2005,127:5040. |
[17] | Axtell A T;Cobley C J;Klosin J;Whiteker G T,Zanotti-Gerosa A,Abboud K A .[J].Angewandte Chemie International Edition,2005,44:5834. |
[18] | Tomas P J;Axtell A T;Klosin J;Peng W Rand C L Clark T P Landis C R Abboud K A .[J].Organic Letters,2007,9:2665. |
[19] | Chen H;Li Y Z;Li R X;Cheng P M,Li X J .[J].Journal of Molecular Catalysis A:Chemical,2003,198:1. |
[20] | Wang X;Fu H Y;Li X J;Chen H .[J].Catalysis Communications,2004,5:739. |
[21] | Lin Q;Jiang WD;Fu HY;Chen H;Li XJ .Hydroformylation of higher olefin in halogen-free ionic liquids catalyzed by water-soluble rhodium-phosphine complexes[J].Applied Catalysis, A. General: An International Journal Devoted to Catalytic Science and Its Applications,2007(1):83-87. |
[22] | Devon T J;Phillips G W;Puckette T A;Stavinoha J L Vanderbilt J J .[P].US 4 694 109,1987. |
[23] | Bonati F;Wilkinson G .[J].Journal of the Chemical Society,1964,86:3156. |
[24] | Deshpande R M;Chaudhari R V .[J].Journal of Molecular Catalysis,1989,57:177. |
[25] | Piras I;Jennerjahn R;Jackstell R;Spannenberg A Franke R Beller M .[J].Angewandte Chemie,2011,123:294. |
[26] | Casey C P;Whiteker G T;Melville M G;Petrovich L M Gavney J J A Powell D R .[J].Journal of the American Chemical Society,1992,114:5535. |
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