Method for preparing 5-hydroxymethyl-furfural

A technology of hydroxymethyl furfural and ionic liquid, applied in the production field of 5-hydroxymethyl furfural, can solve the problem of lack of efficient and low-cost reaction system, effective separation and purification of HMF, unfavorable industrial production of HMF, large amount of silica gel, etc. problems, to achieve the effect of less catalyst and solvent consumption, less requirements for corrosion resistance, and shortened reaction time

Inactive Publication Date: 2009-06-17
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the column chromatography method reported in this patent has realized the separation of HMF and ionic liquid and product purification, the column chromatography method involves the use of volatile organic solvents, the separation amount is small, the use of silica gel is large, and the separation cost is high, which is not conducive to HMF industrial production
[0007] In conclusion, although various methods of converting fructose or other biomass sugar sources to prepare HMF have been reported, there is still a lack of efficient, low-cost reaction systems and effective separation and purification of HMF.

Method used

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  • Method for preparing 5-hydroxymethyl-furfural
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  • Method for preparing 5-hydroxymethyl-furfural

Examples

Experimental program
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Effect test

Embodiment 1

[0040] Add 20 grams of ionic liquid [C4MIm]Cl into the reactor, heat to 100°C, add 10 grams of fructose, and then add 0.25 grams of concentrated sulfuric acid, and continue the reaction at 100°C for 20 minutes under normal pressure before stopping.

[0041] The reaction system was directly decompressed to 133Pa, and the 114-116°C fraction was collected by distillation to obtain 6.6 grams of a dark yellow liquid product. The nuclear magnetic resonance (NMR) analysis data of this product were: 1 H NMR (400MHz, CDCl 3 ): δ 9.49(s, 1H), 7.20(d, 1H), 6.48(d, 1H), 4.65(s, 2H); 13 CNMR (100MHz, CDCl 3 ): δ 178.2, 161.6, 152.5, 123.9, 110.4, 57.7. The measured data of the product is completely consistent with the NMR data obtained by using the HMF reagent provided by Sigma, and then analyzed by ultraviolet-visible spectroscopy, it is found that the absorption peak is 282nm, which is consistent with the literature report, confirming that the product is HMF, and the yield is 94%.

[...

Embodiment 2

[0044] 20 g of ionic liquid [C 4 MIm]Cl was added to the reactor, heated to 80°C, 10 grams of fructose was added, followed by 0.25 grams of concentrated sulfuric acid, and the reaction was stopped after 30 minutes at 100°C.

[0045] The reaction system was directly distilled under the operating pressure of 2.0KPa, and the low-boiling substances were distilled off at 80°C, and the pressure was continued to 3.0Pa, and the fraction at 110°C was collected to obtain 6.5 grams of dark yellow liquid product. The nuclear magnetic resonance spectrum (NMR) analysis data of the product The analysis data of ultraviolet-visible spectrum is the same as that of Example 1, and it is confirmed that the product is HMF, and the yield is 93%.

[0046] The vacuum distillation residue was returned to normal pressure and cooled to 80° C., 10 g of fructose and 0.25 g of concentrated sulfuric acid were added, and the reaction and product separation were carried out as described above to obtain 6.3 g o...

Embodiment 3

[0048] 20 g of ionic liquid [C 4 MIm]Cl was added to the reactor, heated to 100°C, 20 g of fructose was added, followed by 0.5 g of concentrated sulfuric acid, and the reaction was continued at 100°C for 30 minutes before stopping. The reaction system was decompressed to 2.0KPa, and low-boiling substances were distilled off at 80°C; the pressure was continued to 267Pa, and fractions at 141°C to 142°C were collected by distillation to obtain 12.5 grams of a dark yellow liquid product, which was analyzed by nuclear magnetic resonance (NMR) The analysis data of ultraviolet-visible spectrum is the same as that in Example 1, and it is confirmed that the product is HMF, and the yield is 89%.

[0049] The distillation residue was returned to normal pressure and cooled to 100° C., 20 g of fructose and 0.5 g of concentrated sulfuric acid were added, and reacted and separated as described above to obtain 11.8 g of a dark yellow liquid product with a HMF yield of 84%.

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Abstract

The invention relates to a method for preparing 5-hydroxymethylfurfural (HMF) by transforming a biomass saccharine source. The method comprises the following concrete steps: using an ionic liquid as a solvent, hexose or hexose source biomass as a raw material substrate, and acid as a catalyst, heating the mixture to react for 5 minutes to 20 hours at normal pressure, and then depressurizing and distilling the mixture under the condition that an operation temperature is not higher than 180 DEG C to obtain the HMF after the reaction is ended; and after the distilled remainder is cooled, directly adding the remainder into the biomass saccharine source, and repeating the processes of reaction and separation to obtain the HMF, so as to realize recycling of an ionic liquid catalyst system and semi-continuous preparation of the HMF. By using the method, once through yield of the HMF reaches as high as 94 percent. The method has the advantages of high selectivity, low acid consumption, mild condition, quick reaction, reusability of the ionic liquid, low cost, simple process, environmental protection, semi-continuous production and the like, and provides new technology for industrialized production of the HMF by transforming the biomass saccharine source, so as to develop a new path for preparing common chemicals in a large scale by using biomass resources and replacing fuels.

Description

technical field [0001] The present invention relates to the production of 5-hydroxymethylfurfural (HMF), specifically a kind of high-efficiency conversion biomass sugar source (six-carbon sugar or biomass rich in six-carbon sugar) in ionic liquid, through vacuum distillation Separation of HMF and direct recycling of ionic liquids in a semi-continuous HMF production process. Background technique [0002] Dwindling oil reserves and global warming require humans to find a sustainable, carbon-neutral fuel to reduce dependence on fossil fuels. Using biomass to replace petroleum to prepare chemicals, plastics and fuels is one of the feasible solutions to the world's energy crisis. The preparation of general-purpose chemicals from renewable biological resources has become a research hotspot in the field of resources and energy at home and abroad. Biomass can be converted under suitable conditions into valuable intermediate compounds such as polyols, furfural, HMF and levulinic aci...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/46B01J31/02
Inventor 赵宗保李昌志
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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