Glycerol → n-Heptanal Glycerol
Reaction equation
[CH:1](=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[OH:9][CH2:10][CH:11]([CH2:13][OH:14])[OH:12]>[Pd]>[CH:1](=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[OH:9][CH2:10][CH:11]([CH2:13][OH:14])[OH:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 200 °C
Procedure
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%).