Synthesis of pseudoionones by acid and base solid catalysts

被引:62
作者
Climent, MJ [1 ]
Corma, A [1 ]
Iborra, S [1 ]
Velty, A [1 ]
机构
[1] Univ Politecn Valencia, Inst Tecnol Quim, CSIC, Valencia 46022, Spain
关键词
solid base catalysts for pseudoionones; solid base catalysts for citral acetone condensation; solid base catalysts for adol condensation; hydrotalcites for condensation reactions;
D O I
10.1023/A:1015364526587
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The preparation of pseudoionones by aldol condensation reaction between citral and acetone have been carried out in the presence of acid (HY and beta zeolites), an acid-base (amorphous aluminophosphate) and basic catalysts such as an aluminophosphate oxynitride, MgO and different activated hydrotalcites. The results showed that acid or acid-base catalysts were not successful for performing in one pot the preparation of ionones. MgO and calcined hydrotalcites showed excellent activity and selectivity to pseudoionones, with calcined hydrotalcite more selective than MgO. Moreover, the rate of reaction can be improved by activating the hydrotalcite through rehydration. This activation can be successfully done by simply adding the optimum amount of water to the calcined hydrotalcite before reaction. The inhibiting effect of the concentration citral on the catalytic activity of rehydrated hydrotalcites that has been reported to occur at 273 K can be avoided by working at a reaction temperature of 333 K.
引用
收藏
页码:157 / 163
页数:7
相关论文
共 24 条
[1]  
[Anonymous], COMMON FRAGRANCES FL
[2]  
BAHRMANN H, 1995, Patent No. 646563
[3]   BASE CATALYSIS FOR FINE CHEMICALS PRODUCTION - CLAISEN-SCHMIDT CONDENSATION ON ZEOLITES AND HYDROTALCITES FOR THE PRODUCTION OF CHALCONES AND FLAVANONES OF PHARMACEUTICAL INTEREST [J].
CLIMENT, MJ ;
CORMA, A ;
IBORRA, S ;
PRIMO, J .
JOURNAL OF CATALYSIS, 1995, 151 (01) :60-66
[4]   Aluminophosphates oxynitrides as base catalysts: Nature of the base sites and their catalytic implications [J].
Climent, MJ ;
Corma, A ;
Fornes, V ;
Frau, A ;
GuilLopez, R ;
Iborra, S ;
Primo, J .
JOURNAL OF CATALYSIS, 1996, 163 (02) :392-398
[5]  
GABOR CGODWIN AD, 1996, Patent No. 19960117
[6]   3-METHYL-2H-1-BENZOPYRAN POTASSIUM CHANNEL ACTIVATORS [J].
GERICKE, R ;
HARTING, J ;
LUES, I ;
SCHITTENHELM, C .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (10) :3074-3085
[7]   Hydrotalcites as base catalysts. Kinetics of Claisen-Schmidt condensation, intramolecular condensation of acetonylacetone and synthesis of chalcone [J].
Guida, A ;
Lhouty, MH ;
Tichit, D ;
Figueras, F ;
Geneste, P .
APPLIED CATALYSIS A-GENERAL, 1997, 164 (1-2) :251-264
[8]  
HORNING EC, 1955, ORGANIC SYNTHESIS CO, V3, P750
[9]  
JANITSCHKE L, 1982, Patent No. 62291
[10]   Vasodilating and antiarrhythmic activity of heteryl lactones [J].
Leite, L ;
Jansone, D ;
Veveris, M ;
Cirule, H ;
Popelis, Y ;
Melikyan, G ;
Avetisyan, A ;
Lukevics, E .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1999, 34 (10) :859-865