Glycerol → n-Heptanal Glycerol

HRID 74132

Reaction equation

HRID 74132 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

HCID 753GlycerolHCID 8130Heptanal

Product 1

HCID 86639485n-Heptanal Glycerol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

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%).

Workup

  1. custompurged with nitrogen three times
  2. temperatureThe reaction mixture forms two phases upon cooling
  3. customconsumption of n-heptanal

Sources & evidence

ORD record
ord-b541ab114ec4433d8b3be050db067cb6
Source dataset
uspto-grants-2014_09
Patent number
US08829229B2

Linked notes

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