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Method for producing 5- hydroxymethyl-2- furfural or alkyl ether derivatives thereof using an ion exchange resin in the presence of an organic solvent

一种交换树脂、有机溶剂的技术，应用在生产基于呋喃的化合物领域，能够解决增加生产和回收过程成本、不理想等问题，达到有利于分离和纯化、转化率高的效果

Active Publication Date: 2014-06-04
KOREA INST OF IND TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, the concentration of hexose compounds as substrates is as low as about 1% (wt / V) under the reaction conditions, which undesirably increases the cost of the production and recovery process

Method used

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  • Method for producing 5- hydroxymethyl-2- furfural or alkyl ether derivatives thereof using an ion exchange resin in the presence of an organic solvent
  • Method for producing 5- hydroxymethyl-2- furfural or alkyl ether derivatives thereof using an ion exchange resin in the presence of an organic solvent
  • Method for producing 5- hydroxymethyl-2- furfural or alkyl ether derivatives thereof using an ion exchange resin in the presence of an organic solvent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-51

[0094] Examples 1-51 (Step 1)

[0095] In each tubular reactor, put 100mg of glucose and 50-300mg of sodium bicarbonate (NaHCO 3 ) or sodium aluminate (NaAlO 4 ) anion exchange resin (Amberlite IRA-400, Amberlite IRA-900, Amberlite IRA-743, Amberlyst A-26) washed with saturated solution (weight ratio of anion exchange resin / glucose (AER / Glu)=0.5-3).

[0096] In each reactor, 3 ml of an organic solvent (DMSO, DMF, ethanol, dioxane, isopropanol) was placed, and the resulting mixture was stirred at 80-100° C. for a predetermined period of time. After the reaction was terminated, each reactor was cooled to room temperature, diluted with HPLC (high performance liquid chromatography) grade distilled water, and analyzed by HPLC to determine the conversion yield of fructose. The samples were separated by HPLC (Agilent 1200 series) with an ion exclusion column (Bio-Rad Aminex HPX-87H300×7.8 mm), and measured by RID detector to determine the conversion yield.

[0097] The anion excha...

experiment Embodiment 1

[0103] Experimental Example 1: Comparison of Fructose Productivity with Changes in Anion Exchange Resin Washing Solution

[0104] In Examples 1-8, after the reaction was terminated, each reactor was cooled to room temperature, diluted with HPLC grade distilled water, and analyzed by HPLC to determine the yield. The sample was separated by HPLC (Agilent 1200 series) with an ion exclusion column (Bio-Rad Aminex HPX-87H300×7.8mm), and was determined using a RID detector to determine the yield.

[0105] In embodiment 1-8, fructose productive rate is compared with the change situation comparison result of anion exchange resin washing solution as follows figure 1 shown.

[0106] Such as figure 1 It was shown that anion exchange resin (regardless of its type) washed with sodium bicarbonate can produce fructose in 20%-30% yield. On the other hand, in Example 2 using gel-type Amberlite A-26 washed with sodium aluminate, the yield of fructose was as high as 38%, but in Example 2 usin...

experiment Embodiment 2

[0107] Experimental Example 2: Comparison of Fructose Yield with the Weight Ratio of Anion Exchange Resin / Glucose (AER / Glu)

[0108] Reactions in Examples 9-12 (10 minute reaction, Amberlite A-26), Examples 13-16 (30 minute reaction, Amberlite A-26) and Examples 33-36 (10 minute reaction, Amberlite IRA-743) A sample was then taken, diluted with HPLC grade distilled water, and analyzed by HPLC to determine the yield.

[0109] As a result of the analysis, when the weight ratio of anion exchange resin to glucose was 2 (AER / Glu=2), fructose in Example 11 (25%), Example 15 (34%) and Example 35 (18%) Yields are very high.

[0110] In Examples 9-16, the fructose yield varies with the weight ratio of anion exchange resin / glucose as figure 2 shown. Such as figure 2 As shown, the maximum conversion was at the above weight ratio of 2, and the reaction was continued for 30 minutes.

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Abstract

The present invention relates to a method for producing a furan-based compound using an ion exchange resin in the presence of an organic solvent. In the method for producing a furan-based compound according to the present invention, a furan-based compound is made from an aldose-type hexose compound in the presence of an organic solvent by using an anion exchange resin and a cation exchange resin. Thus, the aldose-type hexose compound obtained from biomass by simultaneously or consecutively using the anion / cation exchange resins as catalysts can be made into 5- hydroxymethyl-2- furfural (HMF) or alkyl ether derivatives thereof such as 5- alkoxymethyl-2- furfural (AMF) without using an expensive reagent. Also, since the selection of an organic solvent is not limitative and a heterogeneous catalyst can be used, separation and purification is easy and chemically stable AMF can be directly obtained. Further, the conversion efficiency of the aldose-type hexose compound is excellent, and the hexose compound can be used at a high concentration.

Description

technical field [0001] The present invention relates to a process for the production of furan-based compounds using ion exchange resins in the presence of organic solvents; more particularly, the present invention relates to the production of aldoses derived from biomass by the simultaneous or sequential use of anion exchange resins and cation exchange resins. A method for producing 5-hydroxymethyl-2-furaldehyde (HMF) or its ether derivative 5-alkoxymethyl-2-furaldehyde (AMF) from a hexose compound. Background technique [0002] With the continuous reduction of limited oil resources and the rapid increase of oil demand in emerging developing countries, the imbalance between supply and demand in the market has resulted in high oil prices. In addition, the indiscriminate use of oil generates irreversible greenhouse gases, thereby incurring serious environmental problems such as global warming. [0003] Countries around the world have made many efforts to replace petroleum res...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/50C07D307/48C07H1/00
CPCC07D307/46C07D307/50C07D307/48C07D307/44C07H1/00
Inventor 赵镇玖金相龙曺在勋金保拉保罗·朱
Owner KOREA INST OF IND TECH
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