Difluoroalkyl itaconate and its preparation method

A technology for bisfluoroalkyl itaconate and itaconic acid is applied in the field of bisfluoroalkyl itaconate and its preparation, which can solve problems such as prohibition and cumulative toxicity, and achieve mild preparation process conditions and low equipment requirements. , the effect of high yield

Inactive Publication Date: 2013-01-30
SUZHOU UNIV
View PDF6 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a difluoroalkyl itaconate and its preparation method to solve the cumulative toxicity of existing perfluorooctyl products and the problem of being banned globally

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Difluoroalkyl itaconate and its preparation method
  • Difluoroalkyl itaconate and its preparation method
  • Difluoroalkyl itaconate and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of bis(1,1,5-trihydrooctafluoropentyl) itaconate

[0038] In a reactor equipped with stirring, reflux condenser, water separator, and thermometer, add 150 g of cyclohexane, 26.0 g of itaconic acid, 92.8 g of 1,1,5-trihydrooctafluoropentanol, and hydroquinone 1.9 g and p-toluenesulfonic acid 3.0 g. Stir and heat to 81°C under the protection of nitrogen, react for 6 hours until no more water is formed, and about 6.5 g of water is separated to stop the reaction.

[0039] After the reaction mixture is cooled, filter to obtain a clear filtrate, wash with water until neutral, add 10 g of desiccant to dry for 6 hours, filter to remove the desiccant after drying, and distill off the solvent under reduced pressure from the filtrate at 50°C and a vacuum of 1333.0Pa to obtain a light yellow transparent The oily product is bis(1,1,5-trihydrooctafluoropentyl) itaconate, and the reaction yield is 85.6%. The product structural formula is as follows:

[0040]

[0041]...

Embodiment 2

[0045] Preparation of bis(1,1,2,2-tetrahydrotridecafluorooctyl) itaconate

[0046] In a reactor equipped with stirring, reflux condenser, water separator, and thermometer, add 200 g of toluene, 26.0 g of itaconic acid, 145.6 g of 1,1,2,2-tetrahydrotridecafluorooctyl alcohol, and 1.9 g of phenol and 3.0 g of p-toluenesulfonic acid. Stir and heat to 112°C, react for 8 hours until no more water is formed, and about 7.2 g of water is separated to stop the reaction.

[0047] After the reaction mixture is cooled, filter to obtain a clear filtrate, wash with water until neutral, add 15g of desiccant anhydrous sodium sulfate to dry for 8 hours, filter to remove the desiccant after drying, and distill the filtrate to remove the solvent under reduced pressure at 60°C and vacuum degree of 666.5Pa Bis(1,1,2,2-tetrahydrotridecafluorooctyl) itaconate was obtained as a light yellow transparent oil product, and the reaction yield was 73.2%. The product structural formula is as follows:

[...

Embodiment 3

[0053] Preparation of bis(1,1,3-trihydrotetrafluoropropyl) itaconate

[0054] In a reactor equipped with stirring, reflux condenser, water separator, and thermometer, add 100 g of benzene, 26.0 g of itaconic acid, 52.8 g of 1,1,3-trihydrotetrafluoropropanol, and 2.5 g of hydroquinone and 3.0 g of p-toluenesulfonic acid. Stir and heat to 80°C under the protection of nitrogen, react for 5 hours until no more water is formed, separate about 6.0 g of water, and stop the reaction.

[0055] After the reaction mixture is cooled, filter to obtain a clear filtrate, wash with water until neutral, add 5g of desiccant to dry for 5 hours, filter to remove the desiccant after drying, and distill the filtrate under reduced pressure at 50°C and a vacuum of 1333.0Pa to obtain a light yellow transparent The oily product is bis(1,1,3-trihydrotetrafluoropropyl) itaconate, and the reaction yield is 88.6%. The product structural formula is as follows:

[0056]

[0057] Product structure chara...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses a difluoroalkyl itaconate and its preparation method. An unsaturated dicarboxylic acid reacts with a fluorine-containing alcohol to synthesize a difluoroalkyl unsaturated ester, and the difluoroalkyl itaconate is prepared through an esterification reaction of raw materials comprising the fluorine-containing alcohol and itaconic acid in the presence of a catalyst which is a protonic acid. The molecules of the difluoroalkyl itaconate prepared in the invention contain unsaturated double-bonds, so the difluoroalkyl itaconate can be used as a free radical polymerization raw material to prepare carbon chain polymers, two fluoroalkyl groups are in an intensive stacking state, and the length of the fluorocarbon chain of the fluorocarbon chain is shorter than that of a perfluorooctyl group, so the difluoroalkyl itaconate has no extreme inertia or accumulated toxicity, and does not belong to the forbidding range of fluorine-containing chemicals. The difluoroalkyl itaconate is synthesized through the routine esterification reaction of the raw materials comprising the fluorine-containing alcohol and the itaconic acid, so the synthetic technology has the advantages of mild condition, low equipment requirement, high yield and extremely easy realization of the industrialized production.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a bisfluoroalkyl itaconate and a preparation method thereof. Background technique [0002] In the application process of fluorine-containing long-chain alkyl-substituted polymers, there are a series of problems such as bioaccumulation and environmental hazards in perfluoro-long-carbon chains. Hydrolysis, photolysis or biodegradation will not occur in most environmental condition tests. It is known that among the 171 studied perfluorinated substances predicted by the toxicity assessment, more than 99% of them will become extremely persistent perfluorinated acids due to biodegradation, including perfluorooctanesulfonic acid (PFOS). It is precisely because of the persistence and accumulation of waste brought about by the extreme inertness of such materials that the pollution of these substances to organisms and the environment has attracted more and more attention. The U.S. Envir...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/65C07C67/08
Inventor 李战雄叶皓华陈国强蔡露
Owner SUZHOU UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap