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Dithiocarboxylic acid pentafluorobenzyl ester, preparation method and application thereof

A technology of pentafluorobenzyl ester and dithiocarboxylic acid, applied in the direction of organic chemistry, bulk chemical production, etc., can solve the problems of difficult to effectively control high fluorine-containing monomers, unstable end groups of polymer products, etc., and achieve structural Excellent controllability, good compatibility or affinity, and good solubility

Active Publication Date: 2016-02-03
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] A technical problem to be solved by the present invention is to overcome the difficulty in effectively controlling the controllable free radical polymerization of high fluorine-containing monomers, especially high fluorine-containing (meth)acrylate monomers, and the unstable terminal of the polymerization products in existing RAFT reagents. to provide a kind of polymerization system with excellent solubility in supercritical carbon dioxide, which is suitable for supercritical carbon dioxide medium, can effectively control the free radical polymerization process of high fluorine-containing monomers, and can provide highly Fluorine-containing RAFT reagent pentafluorobenzyl dithiocarboxylate with stable terminal groups

Method used

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  • Dithiocarboxylic acid pentafluorobenzyl ester, preparation method and application thereof
  • Dithiocarboxylic acid pentafluorobenzyl ester, preparation method and application thereof
  • Dithiocarboxylic acid pentafluorobenzyl ester, preparation method and application thereof

Examples

Experimental program
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Embodiment 1

[0027] Synthesis of pentafluorobenzyl dithiopentafluorobenzoate with the following structural formula

[0028]

[0029] Dissolve 1.75mL (14mmol) of pentafluorobromobenzene in 30mL of tetrahydrofuran, and then, under anhydrous and oxygen-free conditions, add 0.36g (15mmol) of magnesium powder and iodine grains (2 to 3 grains) to a three-necked flask gradually. Add the tetrahydrofuran solution of pentafluorobromobenzene dropwise. After the purple (color of iodine) in the reaction mixture disappears, raise the temperature to 70° C. and add the remaining pentafluorobromobenzene dropwise to the three-necked flask under stirring. Tetrahydrofuran solution, control the addition rate to keep the system in a slightly boiling state, continue to react at 70°C for 2 hours after the dropwise addition, so that the reaction of the magnesium powder is completely or basically disappeared, and the Grignard reagent is prepared. Cool the prepared Grignard reagent to 40°C, add 1.14g (15mmol) car...

Embodiment 2

[0031] In embodiment 1, the consumption of carbon disulfide is increased to 1.52g (20mmol), and other steps are identical with embodiment 1, obtain dithiopentafluorobenzoic acid pentafluorobenzyl ester, and its yield is 76% (data after column chromatography separation) ). The appearance, melting point and spectral data of the product are the same as in Example 1.

Embodiment 3

[0033] In Example 1, 1.75mL (14mmol) of pentafluorobromobenzene was dissolved in 15mL of tetrahydrofuran, and then, under anhydrous and oxygen-free conditions at 40°C, 3.73g (28mmol) of ethylmagnesium bromide and 30mL Add tetrahydrofuran solution of pentafluorobromobenzene dropwise to a three-necked tetrahydrofuran flask. After the dropwise addition, raise the temperature to 50°C for 2 hours of reaction. During the reaction process, continuously distill off the produced bromoethane to prepare the Grignard reagent. The other steps were the same as in Example 1 to obtain pentafluorobenzyl dithiopentafluorobenzoate with a yield of 71% (data after separation by column chromatography). The appearance, melting point and spectral data of the product are the same as in Example 1.

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Abstract

The invention discloses a dithiocarboxylic acid pentafluorobenzyl ester, a preparation method and an application thereof. A structural formula of the dithiocarboxylic acid pentafluorobenzyl ester is shown in a specification, the preparation method comprises the following steps: taking pentafluoride bromo-carbons as a substrate, under iodine catalysis, reacting the substrate and magnesium powder or reacting the substrate and brominated ethyl magnesium for synthesizing a grignard reagent having a pentafiuorophenyl end group, reacting the reagent with carbon disulfide for synthesizing to obtain dithiocarboxylate, then performing an esterification reaction with alpha-bromine-2,3,4,5,6-pentafluorotoluene to prepare the dithiocarboxylic acid pentafluorobenzyl ester. According to the invention, the dithiocarboxylic acid pentafluorobenzyl ester can be taken as a high fluorine-containing RAFT reagent, can be used for a supercritical carbon dioxide system to realize RAFT polymerization of a (methyl) fluoroalkyl acrylate fluorine-containing monomer under mild condition, and the prepared fluorine-containing polymer having a highly stable pentafiuorophenyl end group. The polymer has good hydrophobicity, weatherability and soiling resistance, the high fluorine-containing end group can enhance heat stability and transmittance of the polymer, so that application requirement under special condition can be satisfied.

Description

technical field [0001] The invention belongs to the technical field of macromolecule chemistry and chemical engineering, and in particular relates to a fluorine-containing reversible addition-fragmentation chain transfer agent (RAFT reagent) pentafluorobenzyl dithiocarboxylate and a preparation method and application thereof. Background technique [0002] Living / controlled free radical polymerization combines the advantages of free radical polymerization and living polymerization methods. Reversible addition-fragmentation chain transfer polymerization (RAFT polymerization) is a typical living / controlled radical polymerization method. In recent years, RAFT polymerization has become an important method for the design and synthesis of polymer molecules due to its wide application range of monomers, mild polymerization conditions, and effective control of product structure. As well as the synthesis of polymers with complex topological structures such as stars, they have been wi...

Claims

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Application Information

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IPC IPC(8): C07C327/36C08F120/22C08F2/38
CPCY02P20/54
Inventor 陈建刚王明晞周改改冯娴石茹慧刘昭铁沈淑坤刘忠文
Owner SHAANXI NORMAL UNIV
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