A method for co-producing 3,3,3-trifluoropropylene carbonate and 3,3,3-trifluoro-1,2-propanediol

A technology of trifluoropropylene carbonate and propylene glycol, applied in hydrolysis preparation, chemical instruments and methods, preparation of hydroxyl compounds, etc., can solve the problems of complex reaction system, harsh reaction conditions, low reaction selectivity, etc., and achieve high reaction yield , mild reaction conditions, good atom economy

Active Publication Date: 2021-02-23
XIAN MODERN CHEM RES INST
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Problems solved by technology

Although the reaction steps are short, four catalysts and two reaction solvents are involved, the reaction system is complex and the reaction selectivity is low
[0008] Although some reports about TFPC or TFPG have been published, there are no public reports about the joint production of TFPC and TFPG. More importantly, there are various degrees of existence in these methods such as harsh reaction conditions, poor safety performance; reaction atom economy. Poor performance, low yield; many reaction steps, complex reaction system; involving highly toxic and harmful substances, unfriendly to the environment; metal residues, low product quality and other deficiencies, Cheng needs to develop a mild reaction condition, environmentally friendly, atomic economy Co-production method for preparing 3,3,3-trifluoropropylene carbonate and 3,3,3-trifluoro-1,2-propanediol with good performance and adjustable product distribution

Method used

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  • A method for co-producing 3,3,3-trifluoropropylene carbonate and 3,3,3-trifluoro-1,2-propanediol
  • A method for co-producing 3,3,3-trifluoropropylene carbonate and 3,3,3-trifluoro-1,2-propanediol

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 3,3,3-trifluoropropylene oxide (33.6g, 0.3mol) and 2-bromo-1,1,1-trifluoro-3- Propanol (1.5g, 7.5mmol), 2,3-dibromo-1,1,1,2,3,3-hexafluoropropane (4.6g, 15mmol), N-methylimidazole (1.2g, 15mmol) , after sealing with CO 2 Replace the reactor twice, start stirring and heat to 100°C, and continuously feed CO 2 Keep the reaction pressure at 0.5MPa, cool to room temperature after 4 hours of reaction, and slowly release excess CO 2 gas, then add 20% water of 3,3,3-trifluoropropylene oxide molar weight to the reaction solution, and stir the reaction for about 12 hours at 60°C to obtain 3,3,3-trifluoropropylene carbonate and The crude product of 3,3,3-trifluoro-1,2-propanediol was analyzed by gas chromatography, and the target product 3,3,3-trifluoropropene carbonate and 3,3, A total of 44.2 g of 3-trifluoro-1,2-propanediol was calculated and the yield was calculated. The reaction results are shown in Table 1.

[0029] Gas chromatography analysis conditions: Agilent 7820 ga...

Embodiment 2

[0031] In a 500mL stainless steel autoclave equipped with mechanical stirring, 3,3,3-trifluoropropylene oxide (336g, 3mol) and 2-bromo-1,1,1-trifluoro-3-propane were sequentially added with a moisture content of 3000ppm Alcohol (28.9g, 0.15mol), 2,3-dibromo-1,1,1,2,3,3-hexafluoropropane (92.94g, 0.3mol), pyridine (23.7g, 0.3mol), after sealing Using CO 2 Replace the reactor twice, start stirring, set the reaction temperature to 25°C, and continuously feed CO 2 Keep the reaction pressure at 5MPa, and slowly release excess CO after 48 hours of reaction 2 gas, then add 10% water of 3,3,3-trifluoropropylene oxide molar weight to the reaction solution, and stir the reaction for about 24 hours at 40°C to obtain 3,3,3-trifluoropropylene carbonate and The crude product of 3,3,3-trifluoro-1,2-propanediol was analyzed by gas chromatography for reaction product distribution, and the target product 3,3,3-trifluoropropene carbonate and 3,3,3 -A total of 425.7g of trifluoro-1,2-propanedi...

Embodiment 3

[0033] In a 500mL stainless steel autoclave equipped with mechanical stirring, 3,3,3-trifluoropropylene oxide (336g, 3mol) and 2-bromo-1,1,1-trifluoro-3-propane were sequentially added with a moisture content of 5000ppm Alcohol (5.8g, 0.03mol), 2,3-dibromo-1,1,1,2,3,3-hexafluoropropane (9.3g, 0.03mol), pyridine (2.4g, 0.03mol), after sealing Using CO 2 Replace the reactor twice, start stirring, set the reaction temperature to 150°C, and continuously feed CO 2 Keep the reaction pressure at 0.1MPa, cool to room temperature after 2 hours of reaction, and slowly release excess CO 2 gas, then add 30% water of 3,3,3-trifluoropropylene oxide molar weight to the reaction solution, and then stir the reaction at 30°C for about 48h to obtain 3,3,3-trifluoropropylene carbonate With 3,3,3-trifluoro-1,2-propanediol crude product, the reaction product distribution analysis is carried out by gas chromatography, and the target product 3,3,3-trifluoropropene carbonate and 3,3, A total of 415...

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Abstract

The invention discloses a preparation method for the joint production of 3,3,3-trifluoropropylene carbonate and 3,3,3-trifluoro-1,2-propanediol, which comprises the following steps: Trifluoropropylene oxide is used as a raw material, and reacts with carbon dioxide in the presence of small organic molecules. After a period of reaction, add a certain amount of water to the reaction solution, and then react at 30°C-60°C for 4h-48h, Obtain 3,3,3-trifluoropropylene carbonate and 3,3,3-trifluoro-1,2-propanediol crude product, and finally obtain the target product 3,3,3-trifluoropropylene carbonate through separation and refining process with 3,3,3‑trifluoro‑1,2‑propanediol. The invention has the characteristics of mild conditions, environmental friendliness, good atom economy, high reaction yield, and controllable product distribution, and is mainly used for the joint production of 3,3,3-trifluoropropylene carbonate and 3,3,3 ‑Trifluoro‑1,2‑propanediol.

Description

technical field [0001] The present invention relates to a preparation method of fluorine-containing alcohol and fluorine-containing five-membered cyclic carbonate, in particular to a method for the joint production of 3,3,3-trifluoropropylene carbonate (TFPC) and 3,3,3-trifluoropropylene carbonate (TFPC) Fluoro-1,2-propanediol (TFPG) method. Background technique [0002] The introduction of trifluoromethyl into organic compounds can significantly change the acidity, dipole moment, polarity, lipophilicity, and chemical and metabolic stability of the compound. Compounds containing trifluoromethyl are widely used in defense industry, high-tech industry and life increasingly important role in science. 3,3,3-Trifluoropropene carbonate (TFPC) is an important trifluoromethyl-containing compound, which can be used as an electrolyte co-solvent or additive in lithium-ion batteries, and can also be used as a polymer precursor and a reaction solvent Applied in the fields of pharmaceut...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/36C07C29/10C07C31/42
CPCC07C29/106C07D317/36C07C31/42
Inventor 吕剑马辉张伟王博曾纪珺赵波杨志强秦越白彦波李凤仙
Owner XIAN MODERN CHEM RES INST
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