Glycerol → 2-Ethylhexanal Glycerol

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2-Ethylhexanal (12.8 g, 15.6 ml, 0.1 mol), glycerol (92.09 g, 73.7 ml, 1 mol), and 10% Pd/C (5 wt %, 0.64 g) are charged to a Parr reactor, purged with nitrogen three times, heated to 200° C. with stirring and run at 1000 psi of hydrogen for 7 hrs. The reaction mixture forms two phases upon cooling. GC analysis of each phase shows complete consumption of 2-ethylhexanal. Bottom phase (glycerol): glycerol monoethers 3-(2-ethyl)hexoxy-1,2-propanediol and 2-(2-ethyl)hexoxy-1,2-propanediol (55.4%, ratio 13.6), glycerol diethers 1,3-di(2-ethy)hexoxy-2-propanol and 2,3-di(2-ethyl)hexoxy-1-propanol (24.7%), 2-ethyhexanol (3.2%). Top phase (crude product): glycerol monoethers 3-di(2-ethyl)hexoxy-1,2-propanediol and 2-di(2-ethyl)hexoxy-1,2-propanediol (55%, ratio 12.8), glycerol diethers 1,3-di(2-ethy)hexoxy-2-propanol and 2,3-di(2-ethyl)hexoxy-1-propanol (24.8%), 2-ethylhexanol (3.5%).

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