阅读说明：本技术 一种三元共聚催化剂以及三元共聚的制备方法 (Ternary polymerization catalyst and preparation method of ternary polymerization ) 是由 魏艳伟 于 2021-07-22 设计创作，主要内容包括：本发明公开了一种三元共聚催化剂以及三元共聚的制备方法,该催化剂是降冰片烯类、马来酸酐和八氟环戊烯三元共聚的催化剂,具体由下述方法制备得到的：在惰性气体氛围的干燥的单口玻璃瓶中,将三氯化硅、乙酸钠和配体化合物溶解于第一溶剂中,瓶口用乳胶管密封,使用该三元共聚催化剂级进行三元共聚的制备方法包括如下步骤：按照摩尔比1∶1∶1取降冰片烯类、马来酸酐和八氟环戊烯单体加入到高压釜中。本发明提供的催化剂是一种新型纳-硅三元共聚络合物催化剂,催化剂原料廉价易得,能催化降冰片烯类、马来酸酐和八氟环戊烯三元共聚,催化效率高,且产物很容易洗涤分离,共聚物收率高,大大改善了材料的粘结性、可溶性和韧性。(The invention discloses a ternary polymerization catalyst and a preparation method of ternary polymerization, wherein the catalyst is a catalyst for ternary polymerization of norbornenes, maleic anhydride and octafluorocyclopentene, and is prepared by the following method: in a dry single-mouth glass bottle in an inert gas atmosphere, silicon trichloride, sodium acetate and a ligand compound are dissolved in a first solvent, the bottle mouth is sealed by a latex tube, and the preparation method for ternary polymerization by using the ternary polymerization catalyst grade comprises the following steps: norbornene, maleic anhydride and octafluorocyclopentene monomers are taken and added into an autoclave according to the molar ratio of 1: 1. The catalyst provided by the invention is a novel nano-silicon ternary polymerization complex catalyst, the raw materials of the catalyst are cheap and easy to obtain, the catalyst can catalyze the ternary polymerization of norbornenes, maleic anhydride and octafluorocyclopentene, the catalytic efficiency is high, the product is easy to wash and separate, the yield of the copolymer is high, and the cohesiveness, solubility and toughness of the material are greatly improved.)

1. A ternary polymerization catalyst is characterized in that the catalyst is a catalyst for ternary polymerization of norbornenes, maleic anhydride and octafluorocyclopentene, and is prepared by the following method:

dissolving silicon trichloride, sodium acetate and a ligand compound in a first solvent in a dry single-mouth glass bottle in an inert gas atmosphere, sealing the bottle mouth by using a latex tube, and keeping the temperature at 50-65 ℃ for 15-20 minutes to obtain a nano-silicon ternary polymerization complex catalyst;

the molar ratio of the sodium acetate to the ligand compound is 1: 5-5: 1, and the molar ratio of the silicon trichloride to the sodium acetate is 1: 8-8: 1;

the ligand compound is selected from 8-hydroxyquinoline, alpha' -bipyridine, phenanthroline, isoquinoline, quinoline, porphyrin, amines, acetylacetone or benzoyl acetone;

the first solvent is selected from tetrahydrofuran, benzene, toluene, anisole, 1, 4-dioxane or cyclohexanone, and the proportion of the dosage of the first solvent to the sum of silicon trichloride, ligand and sodium acetate is 30 ml: 0.008 to 0.059 mol.

2. The catalyst according to claim 1, wherein the ligand and the first solvent are dried before use; the solid substance in the ligand is firstly purified by recrystallization and then dried by vacuum pumping, and the liquid substance in the ligand is dried by calcium hydride or metallic sodium.

3. The method for producing a ternary copolymer using the norbornene-type, maleic anhydride and octafluorocyclopentene ternary copolymer catalyst according to claim 1, comprising the steps of:

adding norbornene, maleic anhydride and octafluorocyclopentene monomers into an autoclave according to the molar ratio of 1: 1, filling nitrogen, and adding a second solvent for dissolving; then adding the nano-silicon ternary polymerization complex catalyst;

drying the first solvent by using potassium chloride or potassium cyanide, then adding the nano-silicon ternary polymerization complex catalyst, and reacting for 5-8 h at the temperature of 70-180 ℃ and under the pressure of 0.5-9 MPa;

pouring the reaction product into an ethanol solution containing 0.1-5% of hydrochloric acid, washing the obtained precipitate with ethanol to be neutral, and performing vacuum drying to obtain the norbornene, maleic anhydride and octafluorocyclopentene terpolymer;

the second solvent is selected from tetrahydrofuran, benzene, toluene, anisole, 1, 4-dioxane or cyclohexanone, and the proportion of the dosage of the first solvent to the sum of silicon trichloride, ligand and sodium acetate is 20 ml: 0.05 mol.

4. The method of claim 3, wherein the norbornene is selected from the group consisting of bicyclo [2, 2, 1] hept-2-ene, 1-methylbicyclo [2, 2, 1] hept-2-ene, 5-methylbicyclo [2, 2, 1] hept-2-ene, 7-methylbicyclo [2, 2, 1] hept-2-ene, 1-ethylbicyclo [2, 2, 1] hept-2-ene, 5-dimethylbicyclo [2, 2, 1] hept-2-ene, 1-phenylbicyclo [2, 2, 1] hept-2-ene, 5-phenylbicyclo [2, 2, 1] hept-2-ene, and mixtures thereof, 5-Vinylbicyclo [2, 2, 1] hept-2-ene, bicyclo [2, 2, 1] hept-2-ene-5-carboxylic acid methyl ester or bicyclo [2, 2, 1] hept-2-ene-5-carboxylic acid tert-butyl ester.

5. The method of claim 3, wherein the amount of the nano-silicon ternary polymerization complex catalyst is 1 to 4.5% by weight based on the total weight of the norbornene-type compound, the maleic anhydride and the octafluorocyclopentene based on the amount of the silicon trichloride.

Technical Field

The invention relates to the technical field of high polymers, in particular to a ternary polymerization catalyst and a ternary polymerization preparation method.

Background

Polynorbornene is a special polymer, has excellent mechanical property, heat resistance, solubility in organic solvent and transparency, and can be used for 193nm ultraviolet lithography. The main disadvantages of this material are brittleness, poor adhesion and low molecular weight, etc., and as the microelectronics industry develops to require smaller sized components, 157nm f2 lithography can be selected for exposure techniques suitable for line widths of 1.3 μm and below, which relate to various aspects of the lithography process. This puts higher demands on the photolithographic materials, the preparation of photolithographic materials, coating techniques, novel resists, new materials for masks and their protective films, and the like.

The existing methods for synthesizing norbornene copolymers mainly comprise methods such as free radicals, active free radicals, metal catalysts and the like. At present, the synthesis methods have the defects of long reaction time, low yield of the obtained copolymer, small molecular weight of the copolymer, low alternating degree of the copolymer and the like.

Disclosure of Invention

The invention aims to solve the defects in the prior art and provides a ternary polymerization catalyst and a ternary polymerization preparation method.

In order to achieve the purpose, the invention adopts the following technical scheme:

a ternary polymerization catalyst is a catalyst for ternary polymerization of norbornenes, maleic anhydride and octafluorocyclopentene, and is prepared by the following method:

dissolving silicon trichloride, sodium acetate and a ligand compound in a first solvent in a dry single-mouth glass bottle in an inert gas atmosphere, sealing the bottle mouth by using a latex tube, and keeping the temperature at 50-65 ℃ for 15-20 minutes to obtain a nano-silicon ternary polymerization complex catalyst;

the molar ratio of the sodium acetate to the ligand compound is 1: 5-5: 1, and the molar ratio of the silicon trichloride to the sodium acetate is 1: 8-8: 1;

the ligand compound is selected from 8-hydroxyquinoline, alpha' -bipyridine, phenanthroline, isoquinoline, quinoline, porphyrin, amines, acetylacetone or benzoyl acetone;

the first solvent is selected from tetrahydrofuran, benzene, toluene, anisole, 1, 4-dioxane or cyclohexanone, and the proportion of the amount of the first solvent to the sum of silicon trichloride, ligand and sodium acetate is 30 ml: 0.008 to 0.059 mol.

Preferably, the ligand and first solvent are dried prior to use; the solid substance in the ligand is firstly purified by recrystallization and then dried by vacuum pumping, and the liquid substance in the ligand is dried by calcium hydride or metallic sodium.

The preparation method for ternary polymerization by using the norbornene, maleic anhydride and octafluorocyclopentene ternary polymerization catalyst comprises the following steps:

adding norbornene, maleic anhydride and octafluorocyclopentene monomers into an autoclave according to the molar ratio of 1: 1, filling nitrogen, and adding a second solvent for dissolving; then adding the nano-silicon ternary polymerization complex catalyst;

drying the first solvent by using potassium chloride or potassium cyanide, then adding the nano-silicon ternary polymerization complex catalyst, and reacting for 5-8 h at the temperature of 70-180 ℃ and under the pressure of 0.5-9 MPa;

pouring the reaction product into an ethanol solution containing 0.1-5% of hydrochloric acid, washing the obtained precipitate with ethanol to be neutral, and performing vacuum drying to obtain the norbornene, maleic anhydride and octafluorocyclopentene terpolymer;

the second solvent is selected from tetrahydrofuran, benzene, toluene, anisole, 1, 4-dioxane or cyclohexanone, and the proportion of the dosage of the first solvent to the sum of silicon trichloride, ligand and sodium acetate is 20 ml: 0.05 mol.

Preferably, the norbornene is selected from the group consisting of bicyclo [2, 2, 1] hept-2-ene, 1-methylbicyclo [2, 2, 1] hept-2-ene, 5-methylbicyclo [2, 2, 1] hept-2-ene, 7-methylbicyclo [2, 2, 1] hept-2-ene, 1-ethylbicyclo [2, 2, 1] hept-2-ene, 5-dimethylbicyclo [2, 2, 1] hept-2-ene, 1-phenylbicyclo [2, 2, 1] hept-2-ene, 5-vinylbicyclo [2, 2, 1] hept-2-ene, 1-hept-2-ene, Bicyclo [2, 2, 1] hept-2-ene-5-carboxylic acid methyl ester or bicyclo [2, 2, 1] hept-2-ene-5-carboxylic acid tert-butyl ester.

Preferably, the amount of the nano-silicon ternary polymerization complex catalyst is 1 to 4.5 percent of the total weight of the norbornenes, the maleic anhydride and the octafluorocyclopentene based on the amount of silicon trichloride.

The invention has the beneficial effects that:

1. the catalyst provided by the invention is a novel nano-silicon ternary polymerization complex catalyst, the raw materials of the catalyst are cheap and easy to obtain, the catalyst can catalyze the ternary polymerization of norbornenes, maleic anhydride and octafluorocyclopentene, the catalytic efficiency is high, the product is easy to wash and separate, the yield of the copolymer is high, and the cohesiveness, solubility and toughness of the material are greatly improved.

Detailed Description

The present invention will be described in further detail with reference to examples.

In the following examples, the catalyst preparation process, unless otherwise specified, was carried out by drying the ligand and the solvent. Specifically, the method comprises the following steps: the drying of the solid ligand in the ligand is to purify by a recrystallization method and then dry in vacuum; the drying of the liquid ligand in the ligand is drying with calcium hydride or drying with metallic sodium. The solvent is dried with calcium chloride or calcium hydride

Example 1.

In a dry single-mouth glass bottle in an inert gas atmosphere, 0.001 mol of silicon trichloride, 0.001 mol of sodium acetate, 0.001 mol of 8-hydroxyquinoline and 30ml of cyclohexanone are dissolved, the mixture is put into the single-mouth glass bottle which is vacuumized and baked and dried by filling nitrogen for many times, the mouth of the bottle is sealed by a latex tube, and the bottle is put into a constant temperature water tank for 15 minutes at 50 ℃, thus obtaining the nano-silicon ternary polymerization complex catalyst.

0.015 mol of bicyclo [2, 2, 1] hept-2-ene, 0.015 mol of maleic anhydride and 0.015 mol of octafluorocyclopentene are added into a high-pressure autoclave which is vacuumized and filled with nitrogen for a plurality of times, and 30ml of cyclohexanone is added for dissolution. The nano-silicon ternary polymerization complex catalyst is taken according to the amount of the silicon trichloride accounting for 1 percent of the total weight of the norbornenes, the maleic anhydride and the octafluorocyclopentene, and is injected into the mixture by an injector. Reacting at constant temperature of 70 ℃ under the pressure of 0.5MPa for 5 hours. And (3) pouring the product into an ethanol solution containing 5 wt% of hydrochloric acid to precipitate the copolymer, washing the precipitate with ethanol to be neutral, and drying in vacuum to obtain the bicyclo [2, 2, 1] hept-2-ene, maleic anhydride and octafluorocyclopentene terpolymer. The calculated reaction yield was 48.6%.

The reaction yield was calculated as weight of terpolymer/total weight of comonomer x 100%. The yield calculation method in each example described below was the same.

Example 2

In a dry single-mouth glass bottle in an inert gas atmosphere, 0.001 mol of silicon trichloride, 0.02 mol of sodium acetate, 0.001 mol of alpha, alpha' -bipyridine and 30ml of benzene are dissolved, the mixture is put into the single-mouth glass bottle which is vacuumized and baked and dried by filling nitrogen for many times, the mouth of the single-mouth glass bottle is sealed by a latex tube, and the single-mouth glass bottle is put into a constant temperature water tank for 20 minutes at 50 ℃ to obtain the nano-silicon ternary polymerization complex catalyst.

0.015 mol of 1-ethylbicyclo [2, 2, 1] hept-2-ene, 0.015 mol of maleic anhydride and 0.015 mol of octafluorocyclopentene are added into a high-pressure autoclave which is vacuumized and filled with nitrogen for a plurality of times, and 30ml of benzene is added for dissolution. The nano-silicon ternary polymerization complex catalyst is taken according to the amount of silicon trichloride accounting for 2 percent of the total weight of the norbornenes, the maleic anhydride and the octafluorocyclopentene, and is injected into the mixture by an injector. Reacting at constant temperature of 100 ℃ under the pressure of 2MPa for 5 hours. And (3) pouring the product into an ethanol solution containing 5 wt% of hydrochloric acid to precipitate the copolymer, washing the precipitate with ethanol to be neutral, and drying in vacuum to obtain the terpolymer of 1-ethylbicyclo [2, 2, 1] hept-2-ene, maleic anhydride and octafluorocyclopentene. The calculated reaction yield was 59.8%.

Example 3

Dissolving 0.001 mol of silicon trichloride, 0.02 mol of sodium acetate, 0.001 mol of phenanthroline and 30ml of benzene in a dry single-mouth glass bottle in an inert gas atmosphere, putting the single-mouth glass bottle into the single-mouth glass bottle which is subjected to multiple times of vacuumizing and nitrogen filling baking drying, sealing the bottle mouth by using a latex tube, and putting the bottle mouth into a constant temperature water tank for 15 minutes at 60 ℃ to obtain the nano-silicon ternary polymerization complex catalyst.

0.015 mol of 5-dimethylbicyclo [2, 2, 1] hept-2-ene, 0.015 mol of maleic anhydride and 0.015 mol of octafluorocyclopentene are added into a high-pressure autoclave which is vacuumized and filled with nitrogen for a plurality of times, and 30ml of benzene is added for dissolution. The nano-silicon ternary polymerization complex catalyst is taken according to the amount of the silicon trichloride accounting for 1 percent of the total weight of the norbornenes, the maleic anhydride and the octafluorocyclopentene, and is injected into the mixture by an injector. Reacting at constant temperature of 120 ℃ under the pressure of 4MPa for 6 hours. And (3) pouring the product into an ethanol solution containing 5 wt% of hydrochloric acid to precipitate the copolymer, washing the precipitate with ethanol to be neutral, and drying in vacuum to obtain the terpolymer of 5-dimethylbicyclo [2, 2, 1] hept-2-ene, maleic anhydride and octafluorocyclopentene. The calculated reaction yield was 68.5%.

Example 4

Dissolving 0.001 mol of silicon trichloride, 0.02 mol of sodium acetate, 0.001 mol of isoquinoline and 30ml of benzene in a dry single-mouth glass bottle in an inert gas atmosphere, putting the single-mouth glass bottle into the single-mouth glass bottle which is vacuumized and baked and dried by filling nitrogen for many times, sealing the bottle mouth by using an emulsion tube, and putting the bottle mouth into a constant temperature water tank for 20 minutes at 60 ℃ to obtain the nano-silicon ternary polymerization complex catalyst.

0.015 mol of 1-phenyl bicyclo [2, 2, 1] hept-2-ene, 0.015 mol of maleic anhydride and 0.015 mol of octafluorocyclopentene are added into a high-pressure autoclave which is vacuumized and filled with nitrogen for a plurality of times, and 30ml of benzene is added for dissolution. The nano-silicon ternary polymerization complex catalyst is taken according to the amount of the silicon trichloride accounting for 1 percent of the total weight of the norbornenes, the maleic anhydride and the octafluorocyclopentene, and is injected into the mixture by an injector. Reacting at constant temperature of 150 ℃ under the pressure of 4MPa for 6 hours. And (3) pouring the product into an ethanol solution containing 5 wt% of hydrochloric acid to precipitate the copolymer, washing the precipitate with ethanol to be neutral, and drying in vacuum to obtain the terpolymer of 1-phenyl bicyclo [2, 2, 1] hept-2-ene, maleic anhydride and octafluoro cyclopentene. The calculated reaction yield was 56.7%.

Example 5

Dissolving 0.005 mol of silicon trichloride, 0.02 mol of sodium acetate, 0.001 mol of quinoline and 30ml of benzene in a dry single-mouth glass bottle in an inert gas atmosphere, putting the single-mouth glass bottle into the single-mouth glass bottle which is vacuumized and baked and dried by filling nitrogen for many times, sealing the bottle mouth by using a latex tube, and putting the bottle mouth into a constant temperature water tank for 20 minutes at 50 ℃ to obtain the nano-silicon ternary polymerization complex catalyst.

0.015 mol of 5, 5-dimethylbicyclo [2, 2, 1] hept-2-ene, 0.015 mol of maleic anhydride and 0.015 mol of octafluorocyclopentene are added into a high-pressure autoclave which is vacuumized and filled with nitrogen for a plurality of times, and 30ml of benzene is added for dissolution. The nano-silicon ternary polymerization complex catalyst is taken according to the amount of the silicon trichloride accounting for 1 percent of the total weight of the norbornenes, the maleic anhydride and the octafluorocyclopentene, and is injected into the mixture by an injector. Reacting at constant temperature of 160 ℃ under the pressure of 6MPa for 6 hours. And (3) pouring the product into an ethanol solution containing 5 wt% of hydrochloric acid to precipitate the copolymer, washing the precipitate with ethanol to be neutral, and drying in vacuum to obtain the terpolymer of 5, 5-dimethylbicyclo [2, 2, 1] hept-2-ene, maleic anhydride and octafluorocyclopentene. The calculated reaction yield was 70.6%.

Example 6

In a dry single-mouth glass bottle in an inert gas atmosphere, 0.001 mol of silicon trichloride, 0.05 mol of sodium acetate, 0.001 mol of amine and 30ml of 1, 4-dioxane are dissolved, the mixture is put into the single-mouth glass bottle which is vacuumized and baked and dried by filling nitrogen for many times, the mouth of the bottle is sealed by a latex tube, and the bottle is put into a constant temperature water tank for 15 minutes at 65 ℃, thus obtaining the nano-silicon ternary polymerization complex catalyst.

0.015 mol of 5-vinyl bicyclo [2, 2, 1] hept-2-ene, 0.015 mol of maleic anhydride and 0.015 mol of octafluorocyclopentene are added into a multi-vacuumizing and nitrogen-charging autoclave, and 30ml of 1, 4-dioxane is added for dissolution. The nano-silicon ternary polymerization complex catalyst is taken according to the amount of silicon trichloride accounting for 3 percent of the total weight of the norbornenes, the maleic anhydride and the octafluorocyclopentene, and is injected into the mixture by an injector. Reacting at constant temperature of 160 ℃ under the pressure of 7MPa for 6 hours. And (3) pouring the product into an ethanol solution containing 5 wt% of hydrochloric acid to precipitate the copolymer, washing the precipitate with ethanol to be neutral, and drying in vacuum to obtain the terpolymer of 5-vinyl bicyclo [2, 2, 1] hept-2-ene, maleic anhydride and octafluoro cyclopentene. The calculated reaction yield was 65.7%.

Example 7

In a dry single-mouth glass bottle in an inert gas atmosphere, 0.001 mol of silicon trichloride, 0.05 mol of sodium acetate, 0.001 mol of porphyrin and 30ml of 1, 4-dioxane are dissolved, the mixture is put into the single-mouth glass bottle which is vacuumized and baked and dried by filling nitrogen for many times, the mouth of the bottle is sealed by a latex tube, and the bottle is put into a constant temperature water tank for 15 minutes at 60 ℃, thus obtaining the nano-silicon ternary polymerization complex catalyst.

0.015 mol of 7-methyl bicyclo [2, 2, 1] hept-2-ene, 0.015 mol of maleic anhydride and 0.015 mol of octafluorocyclopentene are added into a multi-vacuumizing and nitrogen-charging autoclave, and 30ml of 1, 4-dioxane is added for dissolution. The nano-silicon ternary polymerization complex catalyst is taken according to the amount of silicon trichloride accounting for 4 percent of the total weight of the norbornenes, the maleic anhydride and the octafluorocyclopentene, and is injected into the mixture by an injector. Reacting at constant temperature of 160 ℃ under the pressure of 8MPa for 6 hours. And (3) pouring the product into an ethanol solution containing 5 wt% of hydrochloric acid to precipitate the copolymer, washing the precipitate with ethanol to be neutral, and drying in vacuum to obtain the 7-methyl bicyclo [2, 2, 1] hept-2-ene, maleic anhydride and octafluorocyclopentene terpolymer. The calculated reaction yield was 79.8%.

Example 8

Dissolving 0.001 mol of silicon trichloride, 0.05 mol of sodium acetate, 0.005 mol of acetylacetone and 30ml of methylbenzene in a dry single-mouth glass bottle in an inert gas atmosphere, putting the single-mouth glass bottle which is vacuumized and baked and dried by filling nitrogen for many times, sealing the mouth of the single-mouth glass bottle by using a latex tube, and putting the single-mouth glass bottle into a constant temperature water tank for 20 minutes at 65 ℃ to obtain the nano-silicon ternary polymerization complex catalyst.

0.015 mol of 5-phenyl bicyclo [2, 2, 1] hept-2-ene, 0.015 mol of maleic anhydride and 0.015 mol of octafluorocyclopentene are added into a high-pressure autoclave which is vacuumized and filled with nitrogen for a plurality of times, and 30ml of toluene is added for dissolution. The nano-silicon ternary polymerization complex catalyst is taken according to the amount of silicon trichloride accounting for 4 percent of the total weight of the norbornenes, the maleic anhydride and the octafluorocyclopentene, and is injected into the mixture by an injector. Reacting at the constant temperature of 170 ℃ under the pressure of 9MPa for 6 hours. And (3) pouring the product into an ethanol solution containing 5 wt% of hydrochloric acid to precipitate the copolymer, washing the precipitate with ethanol to be neutral, and drying in vacuum to obtain the terpolymer of 5-phenylbicyclo [2, 2, 1] hept-2-ene, maleic anhydride and octafluorocyclopentene. The calculated reaction yield was 82.6%.

Example 9

Dissolving 0.002 mol of silicon trichloride, 0.05 mol of sodium acetate, 0.005 mol of benzoyl acetone and 30ml of methylbenzene in a dry single-mouth glass bottle in an inert gas atmosphere, putting the single-mouth glass bottle which is subjected to multiple times of vacuumizing and nitrogen-filling baking drying, sealing the mouth of the single-mouth glass bottle by using a latex tube, and putting the single-mouth glass bottle into a constant temperature water tank for 20 minutes at 65 ℃ to obtain the nano-silicon ternary polymerization complex catalyst.

0.015 mol of 5-phenyl bicyclo [2, 2, 1] hept-2-ene, 0.015 mol of maleic anhydride and 0.015 mol of octafluorocyclopentene are added into a high-pressure autoclave which is vacuumized and filled with nitrogen for a plurality of times, and 30ml of toluene is added for dissolution. The nano-silicon ternary polymerization complex catalyst was injected into the above mixture by using a syringe in an amount of 4.5% by weight based on the total weight of norbornene, maleic anhydride and octafluorocyclopentene in terms of the amount of silicon trichloride used in the catalyst. Reacting at 180 ℃ under the pressure of 9MPa for 6 hours. And (3) pouring the product into an ethanol solution containing 5 wt% of hydrochloric acid to precipitate the copolymer, washing the precipitate with ethanol to be neutral, and drying in vacuum to obtain the terpolymer of 5-phenylbicyclo [2, 2, 1] hept-2-ene, maleic anhydride and octafluorocyclopentene. The calculated reaction yield was 85.6%.

The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.