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Production of hydroxymethylfurfural

a technology of hydroxymethylfurfural and hydroxymethylfurfural, which is applied in the direction of hydrocarbon oil treatment, organic compound/hydride/coordination complex catalyst, liquid carbonaceous fuel, etc., can solve the problems of limited replacement of petroleum feedstock by biomass, significant environmental pollution, and rapid reduction of petrochemical reserves

Inactive Publication Date: 2009-12-24
AGENCY FOR SCI TECH & RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Benefits of technology

[0117]A particular embodiment of the invention provides a novel tetrahydrofuran (THF)-butyl-methyl imidazolium chloride (BMIMCl) biphasic system with tungsten salt catalyst for fructose conversion to HMF under mild reaction conditions. The novel tungsten salt catalyst enables HMF to be efficiently synthesized at ≦50° C. in the ionic liquid system. The biphasic system has been successfully applied to a continuous batch reaction process, and may be suitable for large-scale synthesis of HMF from fructose. This is the first organic solvent-ionic liquid biphasic system that enables the conversion of sugars to HMF at low temperatures (≦50° C.) using a novel tungsten salt catalyst. Compared to other systems, this approach is attractive for its mild reaction conditions. The new system may be applied in making biofuel and in the fine chemical industries.

Problems solved by technology

The present consumption of fossil fuels has led to significant levels of environmental pollution and rapidly diminishing petrochemical reserves.
However, the replacement of petroleum feedstock by biomass is limited by the lack of highly efficient methods to selectively convert carbohydrates to chemical compounds for the biofuel production.
However, the large-scale production of HMF is still impeded by the lack of cost-effective synthesis methods.
However, the strongly acidic conditions and the high reaction temperature result in significant material replacement costs and energy consumption.
However, the product extraction and system recovery processes still suffer from low efficiencies.
However, most of them promote side-reactions that form undesired by-products and further rehydration of HMF to form levulinic acid and formic acid.
They are also often limited to simple sugar feedstock, such as fructose.
However, such system has not be shown to convert glucose, which is a more stable and abundant sugar source.

Method used

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  • Production of hydroxymethylfurfural
  • Production of hydroxymethylfurfural
  • Production of hydroxymethylfurfural

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General Information

[0128]All solvents and chemicals were used as obtained from commercial suppliers, unless otherwise indicated. Centrifugation was performed on Eppendorf Centrifuge 5810R (4000 rpm, 10 min). 1H and 13C NMR spectra were recorded on Bruker AV-400 spectrometer (400 MHz). Fructose was quantified using SU-300 Sugar Analyzer (TOA-DKK Corp.).

Preparation of Ipr-WCl6 Catalysts

[0129]1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (467 mg, 1.1 mmol) was mixed with KOtBu (123 mg, 1.1 mmol) in 20 ml of anhydrous N,N-dimethylformamide (DMF). The reaction mixture was allowed to stir for 1 h at room temperature before WCl6 (397 mg, 1 mmol) was added to the mixture, which was then heated to 80° C. and stirred for another 6 h. The reaction mixture was cooled to room temperature and filtered. The green DMF solution was directly used as the catalyst stock solution. Alternatively, the catalyst solution was dried. The resulting green powder was washed with ether and THF, and dried und...

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Abstract

The invention provides a process for making hydroxymethylfurfural. A reaction mixture comprising a saccharide and a metal complex of an N-heterocyclic carbene is initially provided. The saccharide is then allowed to react at about 70° C. or below to form hydroxymethylfurfural. The saccharide may be a hexose or a mixture of hexoses, or a dimer, oligomer or polymer or copolymer of a hexose or a mixture thereof.

Description

TECHNICAL FIELD [0001]The present invention relates to a method of producing hydroxymethylfurfural.BACKGROUND OF THE INVENTION [0002]The present consumption of fossil fuels has led to significant levels of environmental pollution and rapidly diminishing petrochemical reserves. The diminishing fossil fuel reserves and the globe warming effects have become major concerns. The search for sustainable, alternative energy is of critical importance.[0003]Biofuels are highly attractive as the only sustainable source of liquid fuels currently. However, the replacement of petroleum feedstock by biomass is limited by the lack of highly efficient methods to selectively convert carbohydrates to chemical compounds for the biofuel production. A practical catalytic process that can transform the abundant biomass into versatile chemicals would also provide the chemical industry with renewable feedstocks. Biomass-derived carbohydrates represent a promising carbon-based alternative as an energy source...

Claims

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Application Information

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IPC IPC(8): C10L1/18C07D307/48
CPCB01J31/2269B01J31/2273B01J2231/70C10G2300/44C07D307/50C10G2300/1011C10G2300/1014B01J2531/62Y02P20/582Y02P30/20
Inventor ZHANG, YUGENCHAN, JIN Y.G.
Owner AGENCY FOR SCI TECH & RES