Kinetic Study of the Hydrogenation of 2-(6-Methoxy-2-naphthyl)propenoic Acid to (S)-Naproxen with Ruthenium BINAP Catalyst in Methanol
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- 作者：Gary Combes ; Emma Coen ; Fariba Dehghani ; and Neil Foster
- 刊名：Industrial & Engineering Chemistry Research
- 出版年：2006
- 出版时间：February 15, 2006
- 年：2006
- 卷：45
- 期：4
- 页码：1281 - 1290
- 全文大小：146K
- 年卷期：v.45,no.4(February 15, 2006)
- ISSN：1520-5045
文摘
The understanding of efficient chiral syntheses is important in the development of the pharmaceutical industry.The discovery and subsequent investigations of the RuBINAP catalyst for the simple synthesis of thenonsteroidal antiinflammatory drug (NSAID) naproxen is an example of a practical application of chiralsynthesis, although there is little published information on the reaction kinetics. The aim of this study was toprovide kinetic and enantioselectivity data and the Arrhenius parameters for kinetics over a range oftemperatures and H2 pressures under H2 mass-transfer-free conditions. An additional aim was to investigatethe effect of TEA on the reaction rate, which has not been investigated previously for this substrate. Thestudy is innovative in that it uses in situ UV-vis spectroscopy to investigate the reaction kinetics, providingsome significant advantages over intrusive sampling techniques. The study confirmed available literaturevalues and demonstrated that, under a substrate/TEA ratio of 1, the maximum H2 pressure required at 25 
Cwas only 30 bar to achieve a maximum reaction rate and enantioselectivity. TEA was shown to significantlyretard the reaction rate, indicating that there is an optimum TEA/H2 ratio in rate and enantioselectivity.
Cwas only 30 bar to achieve a maximum reaction rate and enantioselectivity. TEA was shown to significantlyretard the reaction rate, indicating that there is an optimum TEA/H2 ratio in rate and enantioselectivity.