The Catalytic Conversion of Saccharides to 5-Hydroxymethyl-2- Furaldehyde (HMF) – A Petroleum Source: A Comprehensive Study into Understanding the Binding of Model Saccharides with Lanthanum and Yttrium Complexes

The Catalytic Conversion of Saccharides to 5-Hydroxymethyl-2- Furaldehyde (HMF) – A Petroleum Source: A Comprehensive Study into Understanding the Binding of Model Saccharides with Lanthanum and Yttrium Complexes

Miniaci Performing Arts Center

There is a burgeoning interest to find new sources of petroleum, as this can alleviate oil prices and fossil fuel shortage concerns. Innovation can be focused on possibly converting wood to fuels, or chemical and industrial products. Saccharides have acquired significance industrially as a promising, suitable, and versatile carbon source for substituting petroleum; particularly, the catalytic conversion of saccharides to 5- hydroxymethyl-2-furaldehyde (HMF). Lanthanide (III) ions, (strong Lewis acids), are active catalysts for converting saccharides to HMF:

Saccharides

Ln3+ Catalyst

-3H2O HOH2C O CHOHMF

Proficient lanthanide-catalysts that convert saccharides to HMF have potential impacts on energy and the environment. Consequently, the primary goal of this project is to understand the binding of model monosaccharide molecules, principally 2-deoxy D ribose and D-glyceraldehyde, to yttrium, europium, and lanthanum ions. By understanding saccharide-metal ion coordination, more important details can be elucidated, providing insights into the lanthanide-based catalysis of saccharides. Air and water stable yttrium, europium and lanthanide compounds were synthesized and reacted with saccharides to form new metal–saccharide complexes. Only a small number of lanthanide- saccharide complexes have previously been isolated. However, the complexes isolated in this experiment are new; these are Ln(hfac)3(saccharide) and Ln(acac) 3(saccharide). The starting materials 1,1,1,5,5,5-hexafluoroacetylacetone (Hhfac) and acetylacetone (Hacac) were used because they allow limited space for coordination of the saccharides to the metal ion. Preliminary results are shared, but further characterization of the new complexes will be performed using percent metal complexometric titration, elemental analysis and nuclear magnetic resonance (NMR) spectroscopy.

O CH

HCH H C OH H C OH

CH2OH

CHO H C OH

CH2OH

D-glyceraldehyde Model Saccharides

2-deoxy-D-ribose