Glycerol → iso-Butyraldehyde Glycerol

HRID 74129Notes

Reaction equation

[CH:1](=[O:5])[CH:2]([CH3:4])[CH3:3].[OH:6][CH2:7][CH:8]([CH2:10][OH:11])[OH:9]>[Pd]>[CH:1](=[O:5])[CH:2]([CH3:4])[CH3:3].[OH:6][CH2:7][CH:8]([CH2:10][OH:11])[OH:9]

Participants

Conditions

Temperature: 200 °C

Procedure

iso-Butyraldehyde (7.21 g, 9.13 ml, 0.1 mol), glycerol (92.09 g, 73.7 ml, 1 mol), and 10% Pd/C (5 wt %, 0.36 g) are charged to the Parr reactor, purged with nitrogen three times, heated to 200° C. with stirring and run at 1000 psi of hydrogen for 8 hrs. GC analysis shows complete consumption of iso-butyraldehyde and formation of glycerol monoethers 3-iso-butyloxy-1,2-propanediol and 2-iso-butoxy-1,2-propanediol (80.1%, ratio 8.2), glycerol diethers 1,3-di-iso-butoxy-2-propanol and 2,3-di-iso-butoxy-1-propanol (7.1%), iso-butanol (2.7%).

Workup

custompurged with nitrogen three times
customconsumption of iso-butyraldehyde and formation of glycerol monoethers 3-iso-butyloxy-1,2-propanediol and 2-iso-butoxy-1,2-propanediol (80.1%, ratio 8.2), glycerol diethers 1,3-di-iso-butoxy-2-propanol and 2,3-di-iso-butoxy-1-propanol (7.1%), iso-butanol (2.7%)

Sources & evidence

ORD record: ord-6c35d028dd4944418d40a0d14069be9f
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829229B2

Reaction notes

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