The preparation method of 5-hydroxymethylfurfural

Background

5-Hydroxymethylfurfural is an organic substance with a molecular formula of C6H6O3 and a molecular weight of 126.11. It is a beige crystalline solid[1]. It is a chemical substance produced by dehydration of glucose or fructose. The molecule contains a furan ring, an aldehyde group and a hydroxymethyl group. The chemical properties are relatively lively. 5-Hydroxymethylfurfural can prepare various derivatives through oxidation, hydrogenation and condensation, and is an important fine chemical raw material.

Picture 1 5-Hydroxymethylfurfural powders

5-Hydroxymethylfurfural is a furfural compound with a furan ring structure produced by dehydration of monosaccharide compounds such as glucose under high temperature or weak acid conditions. It is an endogenous pollutant with potential safety hazards. 5-Hydroxymethylfurfural is an important chemical raw material. Its molecule contains an aldehyde group and a hydroxymethyl group, which can be used to synthesize many useful compounds and new polymer materials through hydrogenation, oxidative dehydrogenation, esterification, halogenation, polymerization, hydrolysis and other chemical reactions, including Medicine, resin-based plastics, diesel fuel additives, etc.

Application

5-hydroxymethylfurfural (5-hydroxymethylfurfural, 5-HMF for short), also known as 5-hydroxymethyl-2-furfural, 5-hydroxymethyl-2-furfural, etc., is a colorless needle-like crystal with Chamomile flower flavor, is a small molecule compound containing furan ring. It is one of the common ingredients in Chinese herbal medicines and Chinese medicine compounds, and is also widely found in raisins, dairy products, honey, cakes and other foods.

Preparation

5-Hydroxymethylfurfural (HMF) can be obtained by acid-catalyzed dehydration of carbohydrates such as fructose, glucose and cellulose. For example, Moreau et al. catalyzed the reaction of fructose at 90 °C for 45 min in the ionic liquid 3-methylimidazole chloride, The yield of HMF was as high as 92%. Takagaki et al. applied the combination of hydrotalcite HT and solid acid (Amberlyst-15) to the reaction of glucose to prepare HMF, and the glucose was isomerized and dehydrated successively to obtain HMF. Process optimization 5-Hydroxymethylfurfural (HMF) is one of the most important platform compounds, and its derivatives have great application prospects in the fields of fine chemicals, medicine, and degradable plastics, especially bio-based PEF polymers based on furandicarboxylic acid. Esters have demonstrated many properties over petroleum-based PET (polyethylene terephthalate). However, since the end of the 19th century, the low-cost and large-scale production of HMF has been an unresolved problem in the international chemical industry. With the support of Zhejiang Tangneng Technology Co., Ltd., Zhang Jian's team from Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, using fructose as raw material, successfully developed a high-efficiency heterogeneous catalysis process with independent intellectual property rights to prepare HMF, which is the first to produce HMF at the thousand-ton level. On a large scale, the catalyst and solvent have been recycled and applied, and the 10,000-ton-level demonstration of the fructose dehydration reaction section has been completed. The HMF single-pass molar yield is 82% to 87%.

Analysis standards by country

Regulations for 5-Hydroxymethylfurfural For Glucose Injection and Glucose Sodium Chloride Injection, ChP, BP and USP all use UV spectrophotometry to measure absorbance at 284nm to control the amount of 5-Hydroxymethylfurfural in the product, Different concentrations have different absorption limits; with the development of detection technology and the improvement of drug quality requirements, the use of high-performance liquid chromatography and other detection methods with better selectivity and higher sensitivity has become a future trend. Some foreign enterprise standards also carry out the limit control of 5-hydroxymethyl furfural for oral preparations using monosaccharides such as glucose, and the Chinese Pharmacopoeia also carries out the limit control of 5-hydroxymethyl furfural for honey and certain honey-containing preparations.

Safety

5-Hydroxymethylfurfural is irritating to eyes, mucous membranes and skin, and has neurotoxicity and genotoxicity; it can be metabolized into 5-sulfoxymethylfurfural (SMF) in vivo, which has strong carcinogenicity and Genotoxicity. Chemical properties Light yellow waxy, easily soluble in methanol and ethanol, derived from Cornus, with high content of d-glucose. Uses for content determination/identification/pharmacological experiments, etc.

Pharmacological efficacy

The compound can effectively prevent and treat neurodegenerative diseases, cognitive impairment and cardiovascular disease against myocardial ischemia, inhibit tumor and lower blood cholesterol. Uses 5-Hydroxymethylfurfural (5-HMF) is an important furan compound, which is widely used in medicine, chemistry, energy and other fields due to its excellent chemical properties. One of the important platform chemicals, its derivatives have great application prospects in the fields of fine chemicals, medicine, degradable plastics, etc. In particular, bio-based PEF polyester based on furandicarboxylic acid has shown better performance than petroleum-based PET (polyparaben). many properties of ethylene phthalate). 5-Hydroxymethylfurfural can be used to detect metabolites of glucose bolus infusion.

Reference

1 Wang Jun, Zhang Chunpeng, Ouyang Pingkai. Research progress on the preparation and application of 5-hydroxymethylfurfural. 2008