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Method for preparing 5-hydroxymethyl furfural and 2,5-furandimethanol simultaneously

A technology of furandimethanol and hydroxymethylfuroic acid, which is applied in the direction of organic chemistry, can solve the problems of large safety hazards, expensive catalysts, and high technical requirements for production equipment, and achieve production process safety, low production equipment requirements, and high reaction efficiency. The effect of mild conditions

Active Publication Date: 2011-01-12
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method must use flammable and explosive high-pressure hydrogen as the reducing agent, which requires high technical requirements for production equipment, and it is also easy to produce deeply reduced products
[0009] In addition, the method reported above can only produce a single compound; additional oxidants or reductants, even high-pressure oxygen or high-pressure hydrogen, need to be provided in excess of the stoichiometric amount, and the production equipment has high technical requirements and great safety hazards; catalyst

Method used

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  • Method for preparing 5-hydroxymethyl furfural and 2,5-furandimethanol simultaneously
  • Method for preparing 5-hydroxymethyl furfural and 2,5-furandimethanol simultaneously
  • Method for preparing 5-hydroxymethyl furfural and 2,5-furandimethanol simultaneously

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] This example provides a method for preparing 5-HMFA and 2,5-FDM from 5-HMF. The base used is KOH. The specific operation is as follows: Weigh 5-HMF (0.5g, 4mmol) into a mortar, add powdered Potassium hydroxide (0.27 g, 4 mmol), triturated at room temperature for 15 min. After the reaction was completed, dilute hydrochloric acid aqueous solution (2ml, 3mol / L) was added to quench the reaction to obtain the product, which was sent to HPLC for detection after adding water to constant volume.

[0056] The specific detection conditions are as follows: liquid phase instrument: Hitachi L-2000 HPLC system, chromatographic column: Cosmosil5C 18 -PAQ column (250×4.6), mobile phase: CH with a volume ratio of 15:85:0.2 3 CN, H 2 A mixture of O and TFA (trifluoroacetic acid), flow rate: 1.0ml / min, column temperature: 30°C, detector: DAD, detection wavelength: 284nm (for detecting 5-HMF), 259nm (for detecting 5-HMF) -HMFA) and 224nm (for detection of 2,5-FDM).

[0057] The resulti...

Embodiment 2

[0059] This example provides a method for preparing 5-HMFA and 2,5-FDM from 5-HMF. The alkali used is NaOH. The specific operation is as follows: Weigh 5-HMF (0.5g, 4mmol) into a mortar, add 0.2ml Water was adjusted to slurry, powdered sodium hydroxide (0.25g, 6mmol) was added, and ground at room temperature for 15min. After the reaction was completed, dilute hydrochloric acid aqueous solution (2ml, 3mol / L) was added to quench the reaction to obtain the product, which was sent to HPLC for detection after adding water to constant volume.

[0060] The specific detection conditions are as follows: liquid phase instrument: Hitachi L-2000 HPLC system, chromatographic column: Cosmosil5C 18 -PAQ column (250×4.6), mobile phase: CH with a volume ratio of 15:85:0.2 3 CN, H 2 A mixture of O and TFA, flow rate: 1.0ml / min, column temperature: 30°C, detector: DAD, detection wavelength: 284nm (for detecting 5-HMF); 259nm (for detecting 5-HMFA) and 224nm (for detection of 2,5-FDM).

[006...

Embodiment 3-10

[0063] According to the same method and conditions as in Example 1, with potassium hydroxide as the base, only the reaction time (grinding time) is replaced according to the different grinding times described in Table 1, and the reaction is completed according to the method provided in Example 1 The system was detected by HPLC, and the conversion rate of 5-HMF, the yield of 5-HMFA and the yield of 2,5-FDM were all listed in Table 1.

[0064] Table 1, the impact of different reaction times on the reaction (alkali: KOH)

[0065]

[0066] As can be seen from Table 1, when potassium hydroxide is used as the base, and its molar amount is the same as that of 5-HMF, after 10 minutes of grinding reaction at room temperature, the conversion rate of raw materials exceeds 90%, and the reaction is basically completed after 30 minutes of grinding reaction.

[0067] The HPLC spectrogram and attached Figure 1-3 There is no substantive difference and will not be described here. From the...

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Abstract

The invention discloses a method for preparing 5-hydroxymethyl furfural and 2,5-furandimethanol simultaneously. According to the method, the 5-hydroxymethyl furfural and the 2,5-furandimethanol can be prepared simultaneously through performing Cannizzaro reaction to the 5-hydroxymethyl furfural (5-HMF). Compared with the previous methods, the method of the invention does not need extra oxidant, reducing agent and expensive metal catalyst, has the advantages of low production equipment requirement, safe production technology, moderate reaction condition, high reaction efficiency and economic atom, can obtain two products at the same time, and accords with the current green chemical technology and the requirement for product diversified production.

Description

technical field [0001] The invention relates to a method for simultaneously preparing and separating 5-hydroxymethylfuroic acid and 2,5-furandimethanol. Background technique [0002] With the depletion of fossil resources and the continuous deterioration of the human environment, it is imminent to seek alternative fuels and basic chemicals from petroleum sources. Biomass is the only renewable resource that can replace fossil resources in the production of chemicals. 5-Hydroxymethylfurfural (5-HMF), prepared from the most widely-occurring carbohydrate in biomass, is known as a bridge connecting petrochemical and biomass chemical industries due to its ability to form many basic chemicals and energy molecules. 5-Hydroxymethylfuroic acid (5-HMFA) and 2,5-furandimethanol (2,5-FDM) prepared from 5-HMF are not only pharmaceutical and pesticide intermediates, but also widely used in degradable polymers in the synthesis of materials. In addition, 5-HMFA has recently been confirmed...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/68C07D307/42
Inventor 傅尧邓晋
Owner UNIV OF SCI & TECH OF CHINA
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