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Preparation method of 3,3,3-trifluoropropylene carbonate

A technology of trifluoropropylene carbonate and trifluoropropylene oxide is applied in the field of synthesis of fluoropropylene carbonate, which can solve the problems of corrosive safety hazards, high price of trifluoropropylene oxide, easy deactivation, etc. The effect of low cost, low raw material cost and high route yield

Inactive Publication Date: 2019-02-22
陕西延长石油集团氟硅化工有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of phosgene in the production process is highly corrosive and has brought huge safety hazards to production.
[0006] Route 3: Synthesize 3,3,3-trifluoropropene carbonate with trifluoropropylene oxide as raw material and insoluble tungsten compound as catalyst, and the yield is significantly improved compared with route 1 and route 2, which is 90% , but trifluoropropylene oxide is expensive and easily deactivated as a raw material

Method used

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  • Preparation method of 3,3,3-trifluoropropylene carbonate
  • Preparation method of 3,3,3-trifluoropropylene carbonate
  • Preparation method of 3,3,3-trifluoropropylene carbonate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] 1. Synthesis of 2-bromo-3,3,3-trifluoro-1-propanol:

[0069] Use excess trifluoropropene to pass into the mixture of 8000mg 20% ​​oleum and 1600mg bromine, keep the temperature at 12-22°C, stop the aeration until the reddish brown of bromine in the flask disappears, add to the mixed solution 15ml of acetic acid was heated at 95°C for 1h. The product was extracted and washed to obtain propyl 2-bromo-3,3,3-trifluoroacetate. After analysis by chromatography-mass spectrometry, the yield was 76.14%, and the selectivity was 95%. Add 35.8 mg of concentrated sulfuric acid and 488 mg of methanol to 1790 mg of 2-bromo-3,3,3-trifluoroacetic acid propyl ester, and after reflux in an oil bath at 70°C for 4 hours, distill off excess methanol and Ethyl formate to give 2-bromo-3,3,3-trifluoro-1-propanol. After chromatographic mass spectrometry analysis, the productive rate is 92.58%, see image 3 .

[0070] 2. Synthesis of 1,1,1-trifluoro-2,3-epoxypropane:

[0071] Add 733.2mg of...

Embodiment 2

[0073] Synthesis of Metal Conjugated Microporous Polymer Complex Catalysts Co-CMP and Co-poly.

[0074] 1. Synthesis of Co-CMP:

[0075] 1.1, with 9.98mmol 3-tert-butyl-2-hydroxybenzaldehyde and 10.3mmol bromine as raw materials, after the reaction solution was stirred for 2 to 3 hours, purified to obtain 5-bromo-3-tert-butyl-2-hydroxybenzaldehyde, the 8.0mmol 5-bromo-3-tert-butyl-2-hydroxybenzaldehyde was dissolved in tetrahydrofuran to form a solution, and the solution was added dropwise to 4.0mmol (R,R)-1,2-diaminocyclohexane solution, Under the condition of 80°C, the reaction mixture was continuously stirred and refluxed for 4-5 hours to obtain the Salen-I ligand through purification.

[0076] 1.2. Add 0.675mmol of Salen-I ligand into the three-necked flask, then seal it, and treat it under anaerobic conditions. Under the protection of argon, add 10ml of anhydrous toluene, stir, and wait until the solid matter is completely dissolved , continue to stir, add 0.96 mmol of ...

Embodiment 3

[0088] Synthesis of 3,3,3-trifluoropropene carbonate:

[0089] 3.1. Polymer catalyst Co-CMP catalyzes the reaction of carbon dioxide with 1,1,1-trifluoro-2,3-propylene oxide: the polymer catalyst Co-CMP, tetrabutylammonium bromide (TBAB) and 1 , 1,1-trifluoro-2,3-epoxypropane is fed according to the mass ratio of 1:5.8:28-56, the carbon dioxide pressure is 0.1-3.0MPa, the temperature is 25-100°C and the reaction is stirred for 1-48h to obtain 3,3,3-Trifluoropropene carbonate. The results are shown in the table below:

[0090]

[0091] As can be seen from the table, when the reaction temperature is increased and the pressure is increased, the yield can reach 97%.

[0092] 3.2. The polymer catalyst Co-poly catalyzes the reaction of carbon dioxide and 1,1,1-trifluoro-2,3-propylene oxide: the polymer catalyst Co-poly and 1,1,1-trifluoro-2, 3-Propylene oxide is fed in a mass ratio of 1:28-56, the carbon dioxide pressure is 0.1-3.0MPa, and the temperature is 25-100°C, stirred an...

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Abstract

The invention discloses a preparation method of 3,3,3-trifluoropropylene carbonate. The preparation method comprises the steps: with trifluoropropylene as a raw material, carrying out several simple reaction steps to obtain trifluoroepoxy propane, introducing carbon dioxide into a high-pressure reaction kettle by taking a metal conjugated microporous polymer complex as a catalyst, and preparing 3,3,3-trifluoropropylene carbonate at the temperature of 25-100 DEG C and the pressure of 0.1Mpa-3Mpa. Compared with the prior art, the method has the advantages that trifluoropropylene is taken as theraw material, so that the raw material cost is substantially lowered; and meanwhile, the yield is relatively high, and the catalyst can be repeatedly used, so that the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of fine organic chemistry and relates to a synthesis method of fluoropropylene carbonate. Background technique [0002] Trifluoropropylene carbonate is the main electrolyte additive for lithium-ion batteries. It has good performance in forming SEI film and forms a compact structural layer without increasing impedance. It can prevent further decomposition of the electrolyte, improve the low-temperature performance of the electrolyte, and significantly improve the performance of the battery. Excellent specific capacity and cycle stability, and at the same time can play a role in flame retardancy, which improves the safety of lithium-ion batteries and prolongs their service life. [0003] At present, the synthetic methods of trifluoropropylene carbonate are as follows: [0004] Route 1: A method for synthesizing 3,3,3-trifluoropropene carbonate through the transesterification reaction of 3,3,3-1,2-propanediol and dimeth...

Claims

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Application Information

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IPC IPC(8): C07D317/36
CPCC07D317/36
Inventor 刘建国邓伟侨杨峰斌尹双良孙同睿孟庆宇张玲武海涛
Owner 陕西延长石油集团氟硅化工有限公司
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