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Method of preparing fluorine-containing alkenyl demoulding intermediate with industrial side product terpinene

A technology for by-producing terpinene and fluorine-containing alkenyl group is applied in the field of preparing fluorine-containing alkenyl-based mold release intermediates, and can solve the problems of difficult separation, difficult economic benefits and the like, and achieves improved processing efficiency, simple and easy reaction operation, The effect of sufficient source of raw materials

Inactive Publication Date: 2017-06-27
修建东
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

With the improvement of social and environmental requirements, traditional perfluorooctyl sulfonyl compounds and perfluorooctanoic acid compounds are restricted or banned due to their harm to the environment and organisms. Some foreign companies and research institutions have carried out research on fluorine release agents A large number of researches, domestic reports on this research and development are less, the existing high-efficiency fluorine release agents basically rely on imports, and use turpentine as raw material to synthesize terpineol, which will produce a large amount of by-product terpinene, by-product pine Oleene accounts for about 20% to 30% of terpineol production. my country is rich in turpentine resources and is one of the countries with the largest production of rosin and turpentine. The by-product terpinene produced by the synthesis of terpineol is huge every year. Oleene is a mixture of isomers with very similar properties, and separation is very difficult, so it can only be used as a low-grade solvent, and it is difficult to produce greater economic benefits

Method used

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  • Method of preparing fluorine-containing alkenyl demoulding intermediate with industrial side product terpinene
  • Method of preparing fluorine-containing alkenyl demoulding intermediate with industrial side product terpinene
  • Method of preparing fluorine-containing alkenyl demoulding intermediate with industrial side product terpinene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] In a four-neck flask equipped with a stirring device, a reflux condensing device and a thermometer, add 25 grams of terpinene and 1 gram of sulfuric acid, and keep it under reflux at 95°C to 105°C for 1 to 2 hours, after that, add 21 grams of maleic acid , 1.1 grams of phenylsulfonic acid and 0.6 grams of aluminum trichloride, continue to reflux reaction at 110°C to 130°C for 5 hours to generate terpinene maleate addition compound, then add 18 grams of hydrogen peroxide and 5 grams of ice Acetic acid, react at 75°C to 85°C for 4 hours, hydrolyze with 5 times the volume of hot water, then hydrolyze, let stand, take the oil layer, and generate dihydroxy compounds; the generated dihydroxy compounds, 110mL N,N-dihydroxy Methyl sulfoxide and 110 grams of hexafluoropropylene oxide oligomers were placed in a four-necked flask, and 0.8 grams of triethylamine was slowly added to perform a nucleophilic substitution reaction for 8 hours. The product was diluted with water, and 25% ...

Embodiment 2

[0028] In a four-neck flask equipped with a stirring device, a reflux condensing device and a thermometer, add 25 grams of terpinene and 1 gram of sulfuric acid, and keep it under reflux at 90 ° C to 100 ° C for 1 to 2 hours, after that, add 24 grams of maleic acid , 1.2 grams of phenylsulfonic acid, continue to reflux at 120°C to 150°C for 6 hours to generate a terpinene maleate addition compound, then add 21 grams of hydrogen peroxide and 4 grams of glacial acetic acid, and heat at 80°C to 90°C React at ℃ for 2 hours, hydrolyze with 5 times the volume of hot water, let it stand, take the oil layer, and generate bishydroxyl compounds; the generated bishydroxyl compounds, 150mL N,N-dimethylsulfoxide and 130g Slowly add 0.5 g of triethylamine to the propane oligomer in a four-necked flask, and carry out the nucleophilic substitution reaction for 6 hours, dilute the product with water, add 25% mass concentration of sodium hydroxide solution, adjust the pH to about 10, Filter, th...

Embodiment 3

[0030] In a four-neck flask equipped with a stirring device, a reflux condensing device and a thermometer, add 25 grams of terpinene and 1 gram of sulfuric acid, and keep it under reflux at 85°C to 95°C for 1 to 2 hours, and then add 27 grams of maleic acid , 1 gram of phenylsulfonic acid and 1 gram of aluminum trichloride, continue to reflux reaction at 130°C to 160°C for 4 hours to generate terpinene maleate addition compound, then add 24 grams of hydrogen peroxide and 6 grams of ice Acetic acid, react at 70°C to 80°C for 3 hours, hydrolyze with 5 times the volume of hot water, let it stand, take the oil layer, and generate bishydroxyl compounds; the generated bishydroxyl compounds, 130mL N,N-dimethylsulfoxide and 120 grams of hexafluoropropylene oxide oligomer in a four-necked bottle, slowly add 1 gram three Ethylamine, after nucleophilic substitution reaction for 7 hours, dilute the product with water, add 25% mass concentration of sodium hydroxide solution, adjust the pH ...

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Abstract

The invention discloses a method of preparing fluorine-containing alkenyl demoulding intermediate with an industrial side product, terpinene. The method uses the industrial side product, terpinene, to prepare the fluorine-containing alkenyl demoulding intermediate, so that the method has abundant raw material source and low cost. The synthesized product is a fluorine-containing dialkenyl dicarboxylate compound and belongs to the fluorine-containing alkenyl demoulding intermediate. The fluorine-containing alkenyl demoulding intermediate can be reacted with an acrylic compound further to synthesize a high-effective fluorine-containing demoulding agent, thus increasing processing efficiency of high-molecular polymers and satisfying market demand. The method has excellent economic and social benefits, has simple reactions and operations, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of release additive synthesis, in particular to a method for preparing a fluorine-containing alkenyl release intermediate by using terpinene, an industrial by-product. Background technique [0002] The release agent is a functional substance between the mold and the finished product. In the field of polymer processing, the use of release agents is essential. Release agents are widely used in metal die casting, polyurethane foam and elastomers, glass fiber reinforced plastics, injection molding thermoplastics, vacuum foamed sheets and In various molding operations such as extrusion profiles. Fluorine-containing compounds have very low surface energy and high thermal and chemical stability, and fluorine release agent is a mixture prepared by mixing the main fluorine-containing compounds and other auxiliary materials, and other types of release agents Compared with other agents, the advantages of fluorine rel...

Claims

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Application Information

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IPC IPC(8): C07C69/757C07C67/08
CPCC07C69/757C07C5/2531C07C5/31C07C51/353C07C51/367C07C67/08C07C67/14C07D301/12C07D303/38
Inventor 修建东
Owner 修建东
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