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Method for asymmetric synthesis of styrene cyclic carbonate with optical activity

A cyclic carbonate, optically active technology, applied in the direction of electrolytic organic production, electrolytic components, air quality improvement, etc., can solve the problems of large amount of catalyst, complex preparation process, high production cost and equipment requirements, and achieves low cost, high technology and low cost. Simple, easy-to-use effects

Inactive Publication Date: 2014-05-14
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the catalytic reaction needs to be carried out under high temperature and high pressure, the amount of catalyst is large, the preparation process is complicated, and the production cost and equipment requirements are relatively high.

Method used

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  • Method for asymmetric synthesis of styrene cyclic carbonate with optical activity

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Experimental program
Comparison scheme
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Embodiment 1

[0020] a. Preparation of electrolyte

[0021] 0.0015mol tetraethylammonium iodide 0.3857g and 0.284 mol acetonitrile 15 mL are mixed into electrolytic solution, then put into the one-chamber electrolytic cell with stainless steel as cathode and magnesium rod as anode; Described tetraethylammonium iodide and Acetonitrile is analytically pure, of which: tetraethylammonium iodide is the supporting electrolyte, and acetonitrile is the solvent after drying with 4? grade molecular sieves.

[0022] b. Electrocarboxylation reaction

[0023] Under normal pressure, carbon dioxide is passed into the electrolytic cell to saturation, and then at 2.88mA / cm 2 The electrocarboxylation reaction is carried out at a constant current density, the current flow is 125C, and the electrolysis temperature is 25°C.

[0024] c. Asymmetric synthesis

[0025] Mix 0.001 mol of racemic styrene oxide with 0.114 mL and 0.00002 mol of Co II -(R,R)(salen) catalyst 0.012g was added to the above-mentioned li...

Embodiment 2

[0030] a. Preparation of electrolyte

[0031] 0.0015mol tetraethylammonium iodide 0.3857g and 0.284 mol acetonitrile 15 mL are mixed into electrolytic solution, then put into the one-chamber electrolytic cell with stainless steel as cathode and magnesium rod as anode; Described tetraethylammonium iodide and Acetonitrile is analytically pure, of which: tetraethylammonium iodide is the supporting electrolyte, and acetonitrile is the solvent after drying with 4? grade molecular sieves.

[0032] b. Electrocarboxylation reaction

[0033] Under normal pressure, carbon dioxide is passed into the electrolytic cell to saturation, and then at 2.88mA / cm 2 The electrocarboxylation reaction is carried out at a constant current density, the current flow is 125C, and the electrolysis temperature is 25°C.

[0034] c. Asymmetric synthesis

[0035] Mix 0.001 mol of racemic styrene oxide with 0.114 mL and 0.00002 mol of Co II -(R,R)(salen) 0.012g catalyst was added to the above-mentioned li...

Embodiment 3

[0040] a. Preparation of electrolyte

[0041] 0.0015mol tetraethylammonium iodide 0.3857g and 0.284 mol acetonitrile 15 mL are mixed into electrolytic solution, then put into the one-chamber electrolytic cell with stainless steel as cathode and magnesium rod as anode; Described tetraethylammonium iodide and Acetonitrile is analytically pure, of which: tetraethylammonium iodide is the supporting electrolyte, and acetonitrile is the solvent after drying with 4? grade molecular sieves.

[0042] b. Electrocarboxylation reaction

[0043] Under normal pressure, carbon dioxide is passed into the electrolytic cell to saturation, and then at 2.88mA / cm 2 The electrocarboxylation reaction is carried out at a constant current density, the current flow is 125C, and the electrolysis temperature is 25°C.

[0044] c. Asymmetric synthesis

[0045] Mix 0.001 mol of racemic styrene oxide with 0.114 mL and 0.00002 mol of Co II -(R,R)(salen) Catalyst 0.012g was added to the above-mentioned liq...

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Abstract

The invention discloses a method for asymmetric synthesis of styrene cyclic carbonate with optical activity. The method is characterized by comprising the steps of mixing tetraethyl ammonium iodide with acetonitrile or N,N-dimethylformamide so as to prepare an electrolyte, saturating carbon dioxide at normal pressure, then, carrying out electric carboxylation reaction with constant current, electrolyzing, then, mixing liquid with racemic styrene oxide, carrying out carbonate synthesis reaction in the presence of a Co<II>-(R,R)(salen) catalyst, and enabling a reaction solution to be subjected to rotary evaporation, extraction and purification, thereby obtaining a product, namely the styrene cyclic carbonate with optical activity. Compared with the prior art, the method has the advantages that the reaction conditions are mild, the process is simple, the operation is convenient, greenhouse effect gas, namely carbon dioxide, can be effectively utilized, the atmospheric pollution is reduced greatly, meanwhile, the transformation of racemic epoxy compounds is realized, the raw materials are cheap and are easily obtained, and the cost is low; the styrene cyclic carbonate serves as an important chiral drug intermediate, so that the method is a process route with an industrial synthesis value, and a new way for researching the asymmetric synthesis of chiral substances, such as cyclic carbonate and the like, is developed.

Description

Technical field [0001] The present invention involves the field of organic chemical synthesis technology. Specifically, it is a method that uses electrochemical asymmetric synthesis with optical activity. Background technique [0002] Since the "response stop" incident in the 1960s, the research in the field of asymmetric synthesis has been the focus of widespread attention in the scientific community and society, and it has also become the direction of methodology in the field.Go forward.The rise of the asymmetry of the chemistry chemistry is relatively late, and the development is relatively slow. The results have not been achieved so far. However, because this method has its own uniqueness and superiority, it has been favored by scientific researchers. [0003] Electrochemical fixed CO 2 The asymmetric synthetic synthetic ring carbonate is a very valuable direction that uses this method. Benjamin R. Buckley and others have reported in CHEM. Commmn., 2011, 47, 1188-11890 and di...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/00
CPCY02A50/20
Inventor 陆嘉星肖艳诸鸿未吕婷王惠梅孙奇龙王欢
Owner EAST CHINA NORMAL UNIV