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Carboxylic ester structure containing diene monomer and polyester thereof, and sulfur-containing polyester

A sulfur-containing polyester and carboxylate technology, which is applied in the field of carboxylate-containing diene monomers and their polyesters and sulfur-containing polyesters, can solve the problems of non-renewable, limited fossil resources, and environmental pollution of fossil resources. , to achieve the effect of easy production, simple synthesis process and reduced dependence

Inactive Publication Date: 2019-08-30
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthetic polyester raw materials are mostly derived from fossil resources such as coal, oil, and natural gas. The fossil resources on the earth are limited and non-renewable, and the development and utilization of fossil resources is accompanied by a series of environmental pollution problems.

Method used

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  • Carboxylic ester structure containing diene monomer and polyester thereof, and sulfur-containing polyester
  • Carboxylic ester structure containing diene monomer and polyester thereof, and sulfur-containing polyester
  • Carboxylic ester structure containing diene monomer and polyester thereof, and sulfur-containing polyester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] p-Hydroxybenzaldehyde allylation reaction, the reaction equation is as follows:

[0081]

[0082] Experimental steps:

[0083] Add p-Hydroxybenzaldehyde (100 mmol) to the flask and dissolve it in 50 ml of absolute ethanol, add anhydrous potassium carbonate (150 mmol) and stir at room temperature for 30 min, add bromopropene (120 mmol) dropwise under nitrogen atmosphere ), the molar ratio of p-hydroxybenzaldehyde, bromopropene and anhydrous potassium carbonate is 1:1.2:1.5, after the dropwise addition, gradually warming up to 80°C, condensing and refluxing, reacting for 72h, filtering, and removing the solvent under reduced pressure distillation , diluted with a small amount of water, extracted with ethyl acetate and saturated brine. Combine the organic phases, add anhydrous sodium sulfate, let stand overnight, collect by silica gel dry method, use the mixed solvent of petroleum ether / ethyl acetate (volume ratio 6:1) as the eluent for chromatographic column separatio...

Embodiment 2

[0085] Vanillin monomer allylation reaction, the reaction equation is as follows:

[0086]

[0087] Experimental steps:

[0088] Add vanillin (150 mmol) and dissolve in 80 milliliters of absolute ethanol in the flask, add anhydrous potassium carbonate (750 mmol) and stir at room temperature for 30 min, add bromopropene (180 mmol) dropwise under nitrogen atmosphere, The molar ratio of vanillin, bromopropene and anhydrous potassium carbonate is 1:1.2:1.5. After the dropwise addition, gradually heat up to 80°C, condense and reflux, react for 48 hours, filter, remove the solvent under reduced pressure distillation, and add a small amount of water Dilute and extract with ethyl acetate and saturated brine. Combine the organic phases, add anhydrous sodium sulfate, let stand overnight, collect by silica gel dry method, use the mixed solvent of petroleum ether / ethyl acetate (volume ratio 4:1) as the eluent for chromatography column separation, and vacuum at 50°C After drying, 26.8...

Embodiment 3

[0090] 3-methyl-4-hydroxybenzaldehyde monomer allylation reaction, the reaction equation is as follows:

[0091]

[0092] Experimental steps:

[0093]Add 3-methyl-4-hydroxybenzaldehyde (10 mmol) to the flask and dissolve it in 30 milliliters of absolute ethanol, add anhydrous potassium carbonate (15 mmol), stir at room temperature for 30 min, gradually Add bromopropene (12 mmoles) dropwise, the molar ratio of syringaldehyde to bromopropene to anhydrous potassium carbonate is 1:1.2:1.5, after the dropwise addition, gradually warm up to 80°C, condense and reflux, react for 48h, filter, and The solvent was distilled off under reduced pressure, diluted with a small amount of water, and extracted with ethyl acetate and saturated brine. Combine the organic phases, add anhydrous sodium sulfate, let stand overnight, collect by silica gel dry method, use the mixed solvent of petroleum ether / ethyl acetate (volume ratio 10:1) as the eluent for chromatography column separation, and va...

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Abstract

The invention discloses a carboxylic ester structure containing diene monomer and polyester thereof, and sulfur-containing polyester. The monomer is prepared through the following steps: 1) with one selected from the group consisting of vanillin, syringaldehyde, p-hydroxybenzaldehyde, 3-fluoro-4-hydroxybenzaldehyde, 3-bromo-4-hydroxybenzaldehyde and 3-methyl-4-hydroxybenzaldehyde as a raw material, dissolving the raw material into an organic solvent, then allowing an obtained solution to react with alkenyl halide under the action of a catalyst, and allowing a reaction product to be recrystallized or separated through a chromatography column so as to obtain an olefine aldehyde monomer; and 2) with the olefine aldehyde monomer as a raw material, allowing the olefine aldehyde monomer to reactunder the action of a catalyst and a promoter without a solvent or after the olefine aldehyde monomer is dissolved in an organic solvent, and allowing a reaction product to be recrystallized or separated through a chromatography column so as to obtain the carboxylic ester structure containing diene monomer. The polyester provided by the invention is prepared under the action of a Hoveyda-Grubbs catalyst and p-benzoquinone. The sulfur-containing polyester provided by the invention is prepared by a reaction of the polyester and a dimercaptan compound. The invention relates to a novel monomer and a polymer. The preparation processes for the monomer and the polymer provided by the invention have the characteristics of rich raw material sources, simple preparation process, no generation of flammable and explosive low-boiling-point volatile matters, greenness, environmental friendliness and universality.

Description

technical field [0001] The invention relates to a diene monomer and its polyester and sulfur-containing polyester, in particular to a carboxylate structure-containing diene monomer and its polyester and sulfur-containing polyester. Background technique [0002] In the rapidly growing global chemical market, olefins have always occupied a large proportion, such as low-carbon olefins such as ethylene, propylene, butadiene, long-chain olefins, cycloolefins, and aromatic olefins such as styrene. As an important class of organic chemical raw materials, olefins have great application value in the field of synthetic plastics, rubber, fibers and other polymer materials. Dienes have certain properties different from ordinary olefins because of their molecular structure containing two carbon-carbon double bonds and because of their reactivity. [0003] Polyester is a high polymer containing carboxylate group structure in the chain link. Conventional polyester is obtained by polyconde...

Claims

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Application Information

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IPC IPC(8): C07C69/92C07C67/39C07C323/12C07C319/18C07D303/24C07D301/14C07D317/38C08G61/12C08G75/045
CPCC07C69/92C07C323/12C07D303/24C07D317/38C08G61/12C08G75/045C08G2261/11C08G2261/1424C08G2261/344C08G2261/419
Inventor 谢海波陈沁任天华
Owner GUIZHOU UNIV
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