Epoxidation of cyclopentene by a low cost and environmentally friendly bicarbonate/peroxide/manganese system

被引:7
作者
Hincapie, Beatriz [1 ]
Llano, Sandra M. [1 ]
Garces, Hector F. [2 ]
Espinal, Diego [1 ]
Suib, Steven L. [3 ]
Garces, Luis J. [1 ]
机构
[1] Univ Antioquia UdeA, Inst Quim, Fac Ciencias Exactas & Nat, Lab Catalisis Ind, Calle 70 52-21, Medellin, Colombia
[2] Brown Univ, Sch Engn, Providence, RI 02912 USA
[3] Univ Connecticut, Dept Chem U 3060, Storrs, CT USA
关键词
Homogeneous catalysis; epoxidation; liquid-phase oxidation; cyclopentene; cyclopentene oxide; manganese sulfate; hydrogen peroxide; HYDROGEN-PEROXIDE; CATALYZED EPOXIDATIONS; SELECTIVE OXIDATION; KINETICS; ALKENES; BICARBONATE; PERFORMANCE; COMPLEX; OXYGEN; AIR;
D O I
10.1177/0263617417701744
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The system hydrogen peroxide/sodium bicarbonate/manganese sulfate was used for the first time to epoxidize cyclopentene. Effects of parameters such as type and amount of solvent, ratio of hydrogen peroxide and manganese sulfate to cyclopentene, presence of additives, and reaction time and temperature on the selectivity to cyclopentene oxide were evaluated. Gas chromatography was used to quantify residual cyclopentene and produced cyclopentene oxide using the internal standard method. Type and amount of solvent, addition method, and temperature were important factors to increase the selectivity to cyclopentene oxide. Unlike previous reports on epoxidation of different substrates, additives like sodium acetate and salicylic acid did not improve the selectivity to cyclopentene oxide. One time, single-step addition of hydrogen peroxide/sodium bicarbonate to the solution of cyclopentene/solvent/manganese sulfate produced more cyclopentene oxide than stepwise addition. The maximum selectivity obtained was 56%, possibly due to the high reactivity of cyclopentene that causes the formation of oxidation products different to cyclopentene oxide, which were not detected in the analyzed phase.
引用
收藏
页码:9 / 22
页数:14
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