Glycerol → n-Heptanal Glycerol

Participants

Reaction Conditions

Reaction Steps

n-Heptanal (11.4 g, 14.0 ml, 0.1 mol), glycerol (92.09 g, 73.7 ml, 1 mol), and 10% Pd/C (5 wt %, 0.57 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 8 hrs. The reaction mixture forms two phases upon cooling. GC analysis of each phase shows complete consumption of n-heptanal. Bottom phase (glycerol): glycerol monoethers 3-heptoxy-1,2-propanediol and 2-heptoxy-1,2-propanediol (78.7%, ratio 7.7), glycerol diethers 1,3-diheptoxy-2-propanol and 2,3-diheptoxy-1-propanol (11.8%), n-heptanol (4.2%). Top phase (crude product): glycerol monoethers 3-heptoxy-1,2-propanediol and 2-heptoxy-1,2-propanediol (72.6%, ratio 7.9), glycerol diethers 1,3-diheptoxy-2-propanol and 2,3-diheptoxy-1-propanol (17.1%), n-heptanol (4.3%).

Provenance & Evidence