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Electrochemical Fixation of Carbon Dioxide by the Use of Fluidized Electrochemical Cell-Synthesis of Useful Organic Carboxylic Acids

使用流化电化学电池电化学固定二氧化碳-合成有用的有机羧酸

基本信息

批准号：
07555580
负责人：
TOKUDA Masao
金额：
$ 2.37万
依托单位：
HOKKAIDO UNIVERSITY
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (A)
财政年份：
1995
资助国家：
日本
起止时间：
1995 至 1997
项目状态：
已结题

项目摘要

The purpose of this research project is to develop an efficient preparation method of synthetically useful carboxylic acids by electrochemical fixation of carbon dioxide to organic substrates using fluidized electrochemical cell.1.Synthesis of Unsaturated Carboxylic Acids by Electrochemical Carboxylation Using a Reactive-metal Anode-Electrochemical carboxylation of allylic halides, propargylic halides, vinyl halides, vinyl triflates, and 1,4-dibromo-2-bromomethyl-2-butene in the presence of atmospheric carbon dioxide using a reactive-metal anode gave, respectively, alpha, beta-unsaturated acids, beta-keto carboxylic acids, and 3-methylene-4-pentenoic acid in high yields and in high regioselective manners.2.Efficient Synthesis of the Precursor of Anti-inflammatory Agents-Efficient synthesis of alpha, beta-unsaturated acids by electrochemical carboxylation of aryl-substituted vinyl bromides was successfully applied to a synthesis of the precursor of anti-inflammatory agents such as ibuprofen, naproxen, flurbiprofen, cicloprofen, and ketoprofen.3.Electrochemical Carboxylation Using Fluidized Electrochemical Cell-Fluidized electrochemical cell was newly made by us and used in the electrochemical carboxylation. Various reaction conditions such as flow rate of CO_2, temperature, electricity passed, and current density were examined in the electrochemical carboxylation of cinnamyl bromide. Electrochemical carboxylation of various organic halides under optimum conditions gave the corresponding carboxylic acids, including ibuprofen and its precursor, in good yields. Advantages in the use of the fluidized electrochemical cell are that the electrochemical carboxylations can be carried out in higher yields and selectivities, and at higher current densities than those of the usual one-compartment cell.

本研究的目的是开发一种利用流化电化学电池将二氧化碳电化学固定在有机基质上制备合成有用羧酸的高效方法。用反应金属阳极电化学羧化合成不饱和羧酸——在大气二氧化碳存在下，用反应金属阳极对烯丙基卤化物、丙炔卤化物、乙烯基卤化物、三氟乙烯和1,4-二溴-2-溴甲基-2-丁烯进行电化学羧化，分别以高产率和高区域选择性得到α、β -不饱和酸、β -酮羧酸和3-亚甲基-4-戊烯酸。抗炎药前体的高效合成——芳基取代的乙烯基溴的电化学羧基化高效合成α、β -不饱和酸已成功应用于布洛芬、萘普生、氟比洛芬、环洛芬和酮洛芬等抗炎药前体的合成。流态化电化学电池-流态化电化学电池是我们最新研制的用于电化学羧化的电化学电池。考察了肉桂酰溴电化学羧化反应的不同反应条件，如CO_2流速、反应温度、通过电流和电流密度等。各种有机卤化物在最佳条件下进行电化学羧化反应，得到相应的羧酸，包括布洛芬及其前体，收率较高。使用流态化电化学电池的优点是，与通常的单室电池相比，电化学羧化可以在更高的收率和选择性以及更高的电流密度下进行。