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Aldehyde group protection method for biomass-based furan compound

A compound and biomass technology, applied in chemical instruments and methods, physical/chemical process catalysts, organic chemistry, etc., can solve the problems of column chromatography time-consuming, deprotection, solvents, etc., achieve low prices, avoid time-consuming and raw materials, The effect of reducing industrial costs

Pending Publication Date: 2021-10-19
CHINA UNIV OF PETROLEUM (BEIJING)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Column chromatography commonly used in traditional organic synthesis is time and solvent consuming
Also has significant limitations in separating highly polar biomass-based substrates
In addition, the silica gel used in the packed column is weakly acidic, leading to deprotection during purification, which affects the purity of the final product

Method used

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  • Aldehyde group protection method for biomass-based furan compound
  • Aldehyde group protection method for biomass-based furan compound
  • Aldehyde group protection method for biomass-based furan compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] The present embodiment has carried out the screening of catalyst to the aldehyde protection method of the present invention, and specific process comprises:

[0056] Take 1mmol of trifluoromethanesulfonic acid (TFA), sulfuric acid (SA), p-toluenesulfonic acid (PTSA), methanesulfonic acid (MSA), sulfamic acid (SFA), anhydrous sodium bisulfate (SHS), anhydrous Citric acid (CTA) and boric acid (BA) were placed in 10mL clean reaction tubes, respectively marked as serial numbers 1-8, and then 1mmol furfural, 1mmol 1,3-propanediol and 3mL solvent dichloromethane were added, and the The reaction was carried out in an oil bath for 3 h, and after the reaction was completed, 1 mmol of toluene was added as an internal standard, and samples were taken for detection by gas chromatography. The catalytic effect is shown in Table 1 and figure 1 shown.

[0057] Table 1 utilizes Bronsted acid catalyst to prepare the catalytic effect of furfural acetal compound

[0058]

[0059] Thi...

Embodiment 2

[0063] This embodiment optimizes reaction temperature and reaction time, and concrete process is as follows:

[0064] The amount of furfural used in this experiment was 1 mmol, 4 mmol 1,3-propanediol, 1 mmol catalyst, 3 mL solvent methylene chloride, and 1 mmol internal standard toluene; the reaction was carried out under the conditions in Table 2, and samples were taken at different time points for gas chromatography detection. The specific experimental conditions and results are shown in Table 2:

[0065] The catalytic effect of sulfamic acid under the different reaction conditions of table 2

[0066]

[0067]

[0068] According to the contents of Table 2, it can be seen that with the increase of reaction temperature and reaction time, the conversion rate and yield of furfural show a trend of first increasing and then decreasing, wherein the optimum reaction temperature of this reaction is 60 °C, and the optimum reaction time is 180min.

Embodiment 3

[0070] This embodiment investigates the different molar ratios of furfural and 1,3-propanediol, using sulfamic acid as a catalyst to prepare furfural acetal products, the reaction reagents used in this experiment, the amount of each reagent used in the experiment in Example 2 The experiment of No. 17 is the same, except that the ratio of the reaction raw materials is changed. The specific experimental conditions and results are shown in Table 3:

[0071] The catalytic effect of sulfamic acid under the different raw material ratios of table 3

[0072]

[0073] It can be seen from Table 3 that with the change of the molar ratio of furfural and 1,3-propanediol, the conversion rate of furfural and the selectivity of acetal showed a trend of first increasing and then decreasing, among which the best furfural and 1,3-propanediol The molar ratio of propylene glycol is 1:4.

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Abstract

The invention discloses an aldehyde group protection method for a biomass-based furan compound. The aldehyde group protection method comprises the following steps: subjecting the aldehyde group-containing biomass-based furan compound to reacting with an aldehyde group protection reagent under the action of an acidic catalyst to generate an acetal compound, and carrying out efficient separation and purification to obtain a pure acetal compound, wherein the acidic catalyst is selected from a Bronsted acid with a pKa value of -12 to 3; the aldehyde group protection reagent is selected from a monohydric alcohol compound, a binary alcohol compound and even a polyhydric alcohol compound; and the efficient separation and purification step is easy to operate, a traditional time-consuming and solvent-consuming column chromatography separation method is not involved, and preparation of the gram-level analytic-purity acetal product can be easily achieved. The catalyst used in the method is low in price, the purification method is simple and easy to implement, and the method can be used for efficiently preparing the biomass-based furan acetal compound on a large scale for later derivatization reaction.

Description

technical field [0001] The invention relates to the field of synthesis of biomass-based furan acetal compounds, in particular to a method for protecting aldehyde groups of biomass-based furan compounds. Background technique [0002] With the progress of the times, the contradiction between the reduction of non-renewable resource petroleum fuels and the increasing demand of human beings for petroleum fuels has become increasingly prominent. Seeking renewable resources to replace petroleum as fuel is of great significance to reduce the dependence of human production and life on petroleum fuels. [0003] As a renewable energy source, biomass energy is a promising alternative to petroleum resources. In recent years, researchers have paid great attention to how to convert biomass feedstocks into fuels and value-added chemicals. Among them, biomass-based furan aldehydes are important platform compounds derived from biomass. For example, furfural is currently the only industrial...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D407/04B01J27/24B01J37/02B01J37/08B01J37/18
CPCC07D407/04B01J27/24B01J37/0203B01J37/086B01J37/18
Inventor 李江
Owner CHINA UNIV OF PETROLEUM (BEIJING)
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