info

product name:

5-Hydroxymethylfurfural

cas No. :

67-47-0

MF :

C6H6O3

MW :

126.11

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Detail

Quick Details

Synonyms:

5-HMF;

5-Hydroxymethyl-2-furaldehyde;

5-Hydroxymethyl-2-furfuraldehyde;

5-(Hydroxymethyl)furan-2-carbaldehyde

Molecular structure:

Properties

Item

Specifications

Appearance

White powder

Assay

≥99.99%

 

Solubility

5-Hydroxymethylfurfural, referred to as 5-HMF. It is white powder at room temperature, easily soluble in water, methanol, acetone, ethyl acetate, MIBK, dimethylformamide, soluble in ether, benzene, chloroform, etc., slightly soluble in carbon tetrachloride, and hardly soluble in petroleum ether .

Stability

5-Hydroxymethylfurfural reacts with strong bases, strong acids, oxidants and strong reducing agents.

Flammability

5-Hydroxymethylfurfural emits dry and irritating fumes when heated, burning and releasing carbon monoxide and carbon dioxide.

Description

The molecule of 5-Hydroxymethylfurfural contains a furan ring, an aldehyde group and a hydroxymethyl group. Its chemical properties are relatively active. It can be used for hydrogenation, oxidative dehydrogenation, esterification, halogenation, polymerization, hydrolysis, and other chemical reactions. Synthesize many organic compounds and new polymer materials, including medicine, resin plastics, aviation and diesel fuel additives, etc. The preparation method of 5-Hydroxymethylfurfural is mainly the biomass hydrolysis method, which has rich raw material sources and low prices. With 5-Hydroxymethylfurfural as the raw material, it can synthesize a series of products with great market and high added value.

At present, most of the energy and organic chemical raw materials needed in the world come from petroleum, coal and natural gas. These fossil resources have made great contributions to social development and economic prosperity. However, with the gradual depletion of non-renewable fossil resources and the realization of human sustainable development, plant-based biomass resources will be the ideal choice for future energy. There are many types of products produced from biomass raw materials, but most of them are not large in output because of the complexity of the biomass composition and the difficulty of product separation. For example, carbohydrates contain many hydroxyl groups with the same chemical properties, and the reaction selectivity is very poor. One solution is to convert carbohydrates into compounds containing C-C and other functional groups as platform compounds. Then use these platform compounds as raw materials to synthesize or convert into other chemicals. 5-Hydroxymethylfurfural is such a platform compound. 5-Hydroxymethylfurfural is an important bridge substance between carbohydrate chemistry and petrochemistry. It is a platform compound among platform compounds and is hailed by the US Department of Energy as a "sleeping giant." Its potential commercial value is even comparable to terephthalic acid. In 1895, Kiermeyer et al. published the method for the synthesis of 5-Hydroxymethylfurfural for the first time. In 1944, the work of Haworth and Jones made a major breakthrough in the research of 5-Hydroxymethylfurfural. For the first time, the modern synthesis method of 5-Hydroxymethylfurfural and the corresponding synthesis mechanism were proposed. However, Dumesic's article on the synthesis of 5-Hydroxymethylfurfural published in Science in 2006 is the most noteworthy.

At present, industrial platform compounds are mainly obtained from petroleum resources. With the large consumption of petroleum and other non-renewable resources, the price of crude oil continues to rise, and the cost of the petroleum-based chemical industry will continue to increase. Biomass is a sustainable resource with huge quantity and low price, which can be biodegraded and can be continuously regenerated. The discovery of renewable biomass resources for the preparation of new platform compounds is an important solution to the current resource and energy crisis. The main components of renewable biomass resources are hemicellulose, cellulose and lignin, which are hydrolyzed under acidic conditions to produce six-carbon sugars (glucose and fructose), and the six-carbon sugars are dehydrated to form 5-Hydroxymethylfurfural. Because 5-Hydroxymethylfurfural has good reactivity, it can also be used as raw materials to synthesize Furan-2,5-dicarbaldehyde (FDC), 2,5-Furandicarboxylic acid (FDCA), Levulinic acid (LA) and other high value-added products. Therefore, the use of renewable biomass resources to prepare a new platform compound-5-Hydroxymethylfurfural has very broad prospects and far-reaching significance.

5-Hydroxymethylfurfural, as a chemical reaction intermediate with important application potential, has not yet achieved large-scale production from the conversion of biomass. This is due to the complex reaction of carbohydrate dehydration to 5-Hydroxymethylfurfural (such as dehydration reaction, isomerization reaction) , Hydration reaction, aldol condensation reaction, hydrogenation reaction, etc.), these factors will affect the selectivity and yield of 5-Hydroxymethylfurfural. Since the conversion of carbohydrates to 5-Hydroxymethylfurfural includes both series and parallel reactions, the reaction path is relatively complicated and there are many by-products. These constitute the main difficulties in the research of 5-Hydroxymethylfurfural preparation.

Applications

5-Hydroxymethylfurfural can be used in medicine, synthetic resin plastics, and can also be converted into aviation and diesel fuel additives. The 5-Hydroxymethylfurfural molecule contains an aldehyde group and a hydroxyl group. It has good reactivity and can be easily converted into other useful compounds. The derivatives of 5-Hydroxymethylfurfural mainly include Furan-2,5-dicarbaldehyde (FDC), 2,5-Furandicarboxylic acid (FDCA), Levulinic acid (LA) and polymer material monomers.

1. Fuel

5-Hydroxymethylfurfural and its di-substituted derivatives can replace petroleum fuels. Chhed and others used a two-phase system to convert polysaccharides (inulin, sucrose) to 5-Hydroxymethylfurfural, and then added various solid alkaline catalysts (AlMgOx, Pd/MgO-ZrO2, La/ZrO2, MgO/ZrO2, etc.) and certain reagents , Condensation and dehydration form a series of liquid alkanes. These products are excellent substitutes for petroleum fuels.

2. Polymer monomer

5-Hydroxymethylfurfural can be used as a monomer to synthesize optically active and biodegradable polymer materials, which are used in synthetic fiber, rubber and foundry industries. 5-Hydroxymethylfurfural can be oxidized to form 2,5-Furandicarboxylic acid (FDCA). 2,5-Furandicarboxylic acid (FDCA) is a furan derivative with stable properties, which can be used to prepare medicines, insecticides, pesticides, fungicides and perfumes. 2,5-Furandicarboxylic acid can also undergo halogenation, esterification, amidation and other reactions. One of the most important transformations is the formation of polyamide. Smay has synthesized a series of polyamides. The biggest characteristic of these polyamides is their high temperature resistance, which can be widely used in the textile industry. The furan-aromatic polyamide synthesized by Fang et al. has a regular structure and high molecular weight. The polymer solution has liquid crystal behavior and is soluble in concentrated sulfuric acid and NMP/LiCl. Kakinuma and others used fructose as the raw material to produce 5-Hydroxymethylfurfural under H2SO4 catalysis, and then they used KMnO4 to oxidize to produce 2,5-Furandicarboxylic acid (FDCA) with a conversion rate of up to 96.6%. 2,5-furan acrylate. 2,5-Furandicarboxylic acid (FDCA) can be further converted into diacid chloride and diester derivatives. 5-Hydroxymethylfurfural can also be selectively reduced to 2,5-dihydroxymethylfuran and then converted to 2,5-dichlorofuran. These reported furan monomers reflect the broad application prospects of furan polymers.

3. Furan resin

5-Hydroxymethylfurfural has a variety of functional groups and can be used to synthesize various properties of furan products (such as furan resin, furan compound aldehyde resin, furan asphalt cement, etc.). Fang et al. modified furanyl ester as the structural unit through copolymerization, grafting and other means, and obtained a photosensitive material with excellent optical activity through transesterification. Elsa et al. found that HMFAE obtained by the reaction of 5-Hydroxymethylfurfural with triethyl phosphate can undergo bulk transesterification with the polymer EHH to produce photosensitive polymer materials with excellent photoactivity. Lasseuguette et al. studied the polycondensation of furandiyl chloride and isosorbide, and the resulting polyester had biodegradable properties.

4. Fine chemicals

Fine chemicals such as drugs and levulinic acid and macrocyclic compounds with coordination ability can also be prepared by 5-Hydroxymethylfurfural. Dumesic et al. reported that they prepared 5-Hydroxymethylfurfural in a two-phase reaction system while using this system to prepare 2,5-dimethylfuran. The hydroxyl groups on 5-Hydroxymethylfurfural can react with anhydrides or acids to form the corresponding ester compounds. 5-Hydroxymethylfurfural can selectively oxidize aldehyde groups to carboxyl groups and gradually oxidize hydroxyl groups to obtain different compounds. These compounds are lead compounds for the synthesis of drugs and monomers for the synthesis of functional polymers. 5-Hydroxymethylfurfural itself is a compound with pharmaceutical activity, and many Chinese medicines contain this ingredient. 5-Hydroxymethylfurfural can be used as a raw material to synthesize a drug with a furan ring structure, such as the synthesis of the drug Ranitidine for treating ulcers. In addition, 5-Hydroxymethylfurfural also has an insecticidal effect. In an acidic medium, the furan ring can undergo ring-opening reaction to form levulinic acid. Levulinic acid can produce various products through esterification, halogenation, hydrogenation, oxidative dehydrogenation, condensation, and other chemical reactions. At the same time, the carbonyl group at the four position is a potential chiral group, which can be obtained by asymmetric reduction. . 5-Hydroxymethylfurfural can also be converted to 2,5-furandialdehyde, which in turn can synthesize macrocyclic compounds, such as oxygen-containing cyclorodecene. Nelson uses 2,5-furandialdehyde to coordinate with metal ions such as Cu2+ and Cu+ to form macrocyclic compounds. The product obtained by condensation of 2,5-furandialdehyde with amine compounds can coordinate with a series of metal ions.

Packaging

As your requirements

Storage

Avoid light and store with inert gas.