ABSTRACT
The nitric acid oxidation of D-glucose was reinvestigated in an effort to better understand and improve the oxidation and subsequent work up steps. The oxidation was carried out using a computer controlled reactor employing a closed reaction flask under an atmosphere of oxygen which allowed for a catalytic oxidation process with oxygen as the terminal oxidant. Removal of nitric acid from product included the use of both diffusion dialysis and nanofiltration methodologies. Product analysis protocols were developed using ion chromatography.
Subject(s)
Glucose/chemistry , Nitric Acid/chemistry , Chromatography, High Pressure Liquid , Diffusion , Filtration , Glucaric Acid/chemistry , Nanotechnology , Nitric Acid/isolation & purification , Oxidation-ReductionABSTRACT
Aqueous solutions of D-glucaric acid and model polyols xylitol, methyl alpha-D-glucopyranoside or beta-cyclodextrin were freeze dried, then heated, and the product mixtures analyzed by instrumental methods that included GC-MS, electrospray ionization-mass spectrometry (ESIMS), and NMR. The thermal process and analyses were carried out with these polyols in order to determine to what extent multiple acylations of the alcohol functions occurred with D-glucaric acid lactones serving as acylating agents, the extent to which acylations occurred at the 1 degrees alcohol sites, and the relative tendency for acylations to occur at the C1 or C6 end of the glucaryl unit. The results of these studies showed an overwhelming preference for 1 degrees alcohol acylation and preferred acylation occurring at the C1 end of the glucaryl unit.
