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Biomass derivative methyl furan-2,5-dimethyl carbamate and preparation method thereof

A technology of methyl dimethyl carbamate and derivatives, which is applied in the field of biomass derivatives - methyl furan 2,5-dimethyl carbamate and its preparation, which can solve the problem of polluted environment, severe corrosion of equipment, and industrial applications Limitation and other issues, to achieve the effect of mild reaction conditions, high yield, and easy control of the process

Pending Publication Date: 2021-07-16
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these synthesis methods using highly toxic phosgene or isocyanate substances as raw materials are greatly restricted in industrial applications due to their shortcomings such as severe corrosion of equipment, pollution of the environment, and threats to the safety of workers.

Method used

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  • Biomass derivative methyl furan-2,5-dimethyl carbamate and preparation method thereof
  • Biomass derivative methyl furan-2,5-dimethyl carbamate and preparation method thereof
  • Biomass derivative methyl furan-2,5-dimethyl carbamate and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Under a nitrogen atmosphere, 1.56 g (ie 0.012 mol) of 2,5-bis(aminomethyl)furan, 30 ml (ie 0.35 mol) of dimethyl carbonate and 0.25 g of sodium methoxide were added to a Schlenk tube. Then, the mixture was heated to 85° C. and refluxed for 4 hours under stirring, and then the heating was stopped. After the temperature dropped to room temperature, 17wt% hydrochloric acid solution was added dropwise to the reaction solution to pickle to pH=1-2, then filtered, and at the same time washed with distilled water until neutral, and finally recrystallized by absolute ethanol to obtain white crystals. According to high-performance liquid chromatography analysis, the conversion rate of 2,5-bis(aminomethyl)furan was 100%, the yield of methyl furan-2,5-dimethylcarbamate was 99%, and the purity was 99.99%.

[0027] The structural formula of the new compound furan-2,5-dimethylcarbamate methyl ester provided in this example is as follows:

[0028]

[0029] The above-mentioned compo...

Embodiment 2

[0041] Under a nitrogen atmosphere, 1.56 g (ie 0.012 mol) of 2,5-bis(aminomethyl)furan, 30 ml (ie 0.35 mol) of dimethyl carbonate and 1.10 g of sodium methoxide were added to a Schlenk tube. Then, the mixture was heated to 65° C. and refluxed for 6 hours under stirring, and then the heating was stopped. After the temperature dropped to room temperature, 17wt% hydrochloric acid solution was added dropwise to the reaction solution to pickle to pH=1-2, then filtered, and at the same time washed with distilled water until neutral, and finally recrystallized by absolute ethanol to obtain white crystals. According to high-performance liquid chromatography analysis, the conversion rate of 2,5-bis(aminomethyl)furan was 100%, the yield of methyl furan-2,5-dimethylcarbamate was 98%, and the purity was 99.99%.

Embodiment 3

[0043]1.56g (that is, 0.012 moles) of 2,5-bis(aminomethyl)furan, 30ml (that is, 0.35 moles) of dimethyl carbonate and 0.25g of zinc acetate were added to the autoclave, purged with nitrogen, and then stirred Under the conditions, heat up to 160° C. and react for 7 hours, then stop heating. When the temperature dropped to room temperature, non-condensable gas was released, heated to dissolve the precipitated solid, and then vacuum filtered to remove the solid catalyst while it was hot. Then, the solid obtained after the filtrate was distilled under reduced pressure was recrystallized with absolute ethanol to obtain white crystals. According to high-performance liquid chromatography analysis, the conversion rate of 2,5-bis(aminomethyl)furan was 100%, the yield of methyl furan-2,5-dimethylcarbamate was 95%, and the purity was 99.99%.

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Abstract

The invention relates to a biomass derivative methyl furan-2,5-dimethyl carbamate and a preparation method thereof. The structural formula of the compound is shown in the specification. The preparation method comprises the following steps: adding 2,5-bis (aminomethyl) furan, dimethyl carbonate and a catalyst into an atmospheric-pressure or high-pressure reactor in an inert atmosphere, and reacting for 1-7 hours to obtain a product methyl furan-2,5-dimethyl carbamate; the catalyst is sodium methoxide or zinc acetate. The obtained substance can be used as an intermediate for modification and organic synthesis of pesticides, medicines and synthetic resin; the preparation method is green and safe and has a good application prospect.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a biomass derivative - methyl furan 2,5-dimethylcarbamate and a preparation method thereof. Background technique [0002] Carbamate compounds are a class of nitrogen-containing compounds with important biological and pharmaceutical activities, and are widely used in agriculture, medical treatment, health and other fields. Urethane is also the basic skeleton of many natural products and an important synthetic intermediate and chemical raw material. As an organic synthetic intermediate, it can be used to synthesize isocyanate, heterocyclic compounds, non-toxic polyurethane, diphenyl aminomethylphosphonate, and melamine. Derivatives, dialkyl carbonate and polyvinylamine, etc. Urethane can react with olefins, aldehydes, ketones, polyols and aromatic rings to generate derivatives for various purposes, which has important application value. [0003] In view of the wide ra...

Claims

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Application Information

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IPC IPC(8): C07D307/52
CPCC07D307/52
Inventor 王延吉白韵菡宋宇淙丁晓墅李芳赵新强
Owner HEBEI UNIV OF TECH
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