Home
Resources
Publications
Thermal Decomposition of 5-(hydroxymethyl)-2-furaldehyde (HMF) and Its Further Transformations in the Presence of Glycine

Thermal Decomposition of 5-(hydroxymethyl)-2-furaldehyde (HMF) and Its Further Transformations in the Presence of Glycine

Plamen Y Nikolov, Varoujan A Yaylayan

J Agric Food Chem. 2011 Sep 28;59(18):10104-13.

PMID: 21838257

Abstract:

Thermal decomposition of HMF has been so far studied indirectly through carbohydrate degradation reactions assuming HMF as the main product. Such studies, however, do not necessarily generate relevant information on HMF decomposition because many other products are generated simultaneously. Direct thermal decomposition using different concentrations of HMF in silica gel was studied using pyrolysis-GC-MS. Undiluted HMF generated four peaks corresponding to 5-methylfurfural, 2,5-furandicarboxaldehdye, HMF, and a major unknown peak at retention time of 20.73 min. The diluted HMF in silica gel (15-fold) generated only the first three peaks. The generation of the unknown peak was dependent on the concentration of HMF, indicating the possibility of a dimeric structure; furthermore, when HMF was generated from [U-13C6]glucose in the reaction mixture, the highest mass in the spectrum of the unknown peak showed the incorporation of 11 carbon atoms from the glucose. Thermal decomposition studies of HMF have also indicated that in the absence of amino acids it can mainly dimerize and the initially formed dimer can degrade to generate 5-methylfurfural and 2,5-furandicarboxaldehyde. On the other hand, thermal degradation of HMF in the presence of glycine generated Schiff base adducts of HMF, 5-methylfurfural, and 2,5-furandicarboxaldehdye in addition to 2-acetyl-5-methylfuran and a newly discovered adduct, 5-[(dimethylamino)methyl]-2-furanmethanol.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1193799	2-Acetyl-5-methylfuran		1193-79-9	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: