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Preparation of multi-chiral catalyst, preparation and application of cyclic carbonates with optical activity

A cyclocarbonate and optically active technology, which is applied in the field of preparation of highly optically active cyclocarbonate, can solve the problems of exaggerated catalyst performance and achieve the effect of easy acquisition, simple process and low price

Inactive Publication Date: 2008-09-24
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

From attached figure 1 It can be seen that the ee value is 73% when the temperature is -20°C, but the ee value is 30% when the temperature is 25°C! From the difference in these data, it can be seen that the effectiveness of the catalyst is suspected to be exaggerated

Method used

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  • Preparation of multi-chiral catalyst, preparation and application of cyclic carbonates with optical activity
  • Preparation of multi-chiral catalyst, preparation and application of cyclic carbonates with optical activity
  • Preparation of multi-chiral catalyst, preparation and application of cyclic carbonates with optical activity

Examples

Experimental program
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Effect test

Embodiment 1

[0043] In this embodiment, the catalyst 1aCo(OAc) is taken as an example. 1aCo(OAc) refers to the catalyst in the a structure described in formula 3, R=H, M=Co, X=OAc, referred to as 1a. The following 1b refers to the catalyst prepared with R=Cs in the structure of formula 3a, 1c refers to the catalyst prepared with R=Mg in the structure of formula 3a, ..., 2h refers to the catalyst prepared with R=Ph in the b structure of formula 3 Catalysts, 3 and 4 respectively refer to the catalysts prepared with the c structure and d structure in formula 4.

[0044] 1) (+)-(R)-3-formyl-2,2'-dihydroxy-1,1'-binaphthyl (0.314g, 1mmol), dissolved in 4ml ethanol by heating, cooled to room temperature, ( -)-(1R,2R)-Tartrate (0.5mmol) of cyclohexanediamine was dissolved in 0.5ml of water, and 0.5ml of ethanol was added. At this time, a solid appeared, and the supernatant was added to (+)- In (R)-3-formyl-2,2'-dihydroxy-1,1'-binaphthyl, a pink solid appeared, stirred at room temperature for 24 ...

Embodiment 2

[0051] In a stainless steel autoclave with an effective volume of 100ml, add successively: 0.1mmol 1dCo (OAc), 0.1mmol phenyltrimethylammonium tribromide (PTAT), 29 grams (500mmol) propylene oxide (in this embodiment, use Represent racemic propylene oxide, hereinafter the same), then pass into 0.8Mpa carbon dioxide gas. Control the temperature at 25°C, react under magnetic stirring for 24 hours, slowly let off the unreacted carbon dioxide in the autoclave, distill 11 grams of propylene carbonate under reduced pressure, the yield is 21.6%, and modify β by γ-butyl - Cyclodextrin gas chromatography column (30m x 0.25mm x 0.25mm) measured on a Varian CP-3800 chromatogram with an e.e. value of 60.0%. In the reaction, the ratio of co-catalyst to main catalyst is 5-1:; the ratio of main catalyst to alkylene oxide is 0.05%-1%; the pressure of carbon dioxide is 0.1-2Mpa.

Embodiment 3

[0053] In the same equipment used in Example 1, under the same conditions, just using 1fCo(OAc) as a catalyst, after reacting at 25°C for 48 hours, 15 grams of propylene carbonate were obtained, with an e.e. value of 55.3%, yield was 29.4%.

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Abstract

The present invention discloses a preparation method of carbonate with high optical activity, a main catalyst that is used in the method, and a preparation method of the main catalyst. In the method, racemic epoxy alkane and carbon dioxide have catalytic cycloaddition reaction under chiral double-component catalysts to prepare the optically active cyclic carbonate. The main catalyst is the metal complex of double-chiral Schiff base with coordinated four teeth; the auxiliary catalyst is four substituted tribromide or quaternary ammonium salt.

Description

technical field [0001] The invention relates to a preparation method of highly optically active cyclocarbonate, a main catalyst used in the method, and a preparation method of the catalyst. The method of the invention is to prepare optically active cyclic carbonate by using racemic alkylene oxide and carbon dioxide through chiral two-component catalyst to catalyze cycloaddition reaction. Background technique [0002] Cyclic carbonates are high-boiling-point and high-polarity organic solvents with excellent properties, and are widely used in organic synthesis, cosmetics, gas separation, battery dielectrics, and metal extraction. Optically active cyclic carbonates, as chiral starting materials, can be used to synthesize optically active diols and the like. Preparation of optically active cyclic carbonates in the prior art mainly contains the following methods: (1) obtain corresponding chiral cyclic carbonates by cycloaddition reaction of chiral alkylene oxide and carbon dioxi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/36C07B53/00B01J31/22B01J31/26
Inventor 景欢旺靳丽丽
Owner LANZHOU UNIVERSITY
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