Trimethyl-1,4-Benzoquinone Synthesis Via 2,3,6-Trimethylphenol Catalytic Oxidation by Oxygen in the Presence of Non-Keggin-Type Mo-V-Phosphoric Heteropoly Acid Solutions
Journal of Chemistry and Chemical Engineering
Rodikova Yulia Anatolievna
Zhizhina Elena Georgievna
Department of Catalytic Processes of Fine Organic Synthesis, Boreskov Institute of Catalysis Siberian Branch of Russian Academy of Sciences, Novosibirsk 630090, Russia
In the present study, the modified (non-Keggin-type) aqueous solutions of Mo-V-phosphoric heteropoly acids HaPzMoyVx’Ob (HPA-x’) were applied as homogeneous catalysts for the two-stage oxidation of TMP (2,3,6-trimethylphenol) by oxygen into TMQ (2,3,5-trimethyl-1,4-benzoquinone), the latter being the key intermediate in the synthesis of vitamin E. The TMQ yield was analyzed regarding solvent type, reaction temperature, molar HPA-x’:TMP ratio, and the concentration of vanadium (V) in the HPA-x’ solution. The TMQ yield was found to depend strongly on the catalyst redox potential and the rate of electron transfer. The results obtained enabled to establish the optimal reaction conditions as well as to suggest the reaction mechanism. In the target reaction, which proceeds in the two-phase system, the TMQ yield is higher than 99%. After phase separation, the catalyst is rapidly regenerated by oxygen and reused.