COMPARISON OF C-13 NUCLEAR-MAGNETIC-RESONANCE METHODS FOR THE ANALYSIS OF MULTIPLE PARTIALLY DEUTERIATED PRODUCTS FROM CATALYTIC REACTIONS - HEPTAN-1-OL AND 2-METHYLPROPANOL

Products from the hydrocarbonylation of hex-1-ene or prop-2-en-1-ol using H-2-CO or D-2-CO in EtOH or EtOD have been analysed using C-13 NMR techniques. Where there are up to four isotopomers in the products, analysis of beta-shifted resonances in the C-13-{H-1} NMR spectrum can give enough information for quantification of all isotopomers. Using prop-2-en-1-ol, D-2-CO and EtOH, the 2-methylpropanol produced is a mixture of 16 different isotopomers. These can be individually quantified by analysis of the C-13-(H-1, D-2) NMR spectrum. In particular, the resonance from the methyl C atom shows beta and gamma shifts, the latter being different for different types of gamma-D atom. These analytical methods are shown to be superior to other possibilities including H-1 NMR and mass spectrometry.