Glycerol → HCID 86639483, compound

HRID 74130Notes

Reaction equation

[CH:1](=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4].[OH:7][CH2:8][CH:9]([CH2:11][OH:12])[OH:10]>[Pd]>[CH:1](=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4].[OH:7][CH2:8][CH:9]([CH2:11][OH:12])[OH:10]

Participants

Conditions

Temperature: 200 °C

Procedure

iso-Valeraldehyde (8.61 g, 10.8 ml, 0.1 mol), glycerol (92.09 g, 73.7 ml, 1 mol), and 10% Pd/C (5 wt %, 0.43 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 4 hrs. GC analysis shows complete consumption of iso-valeraldehyde and formation of glycerol monoethers 3-iso-pentoxy-1,2-propanediol and 2-isopentoxy-1,2-propanediol (82.0%, ratio 8.5), glycerol diethers 1,3-di-isopentoxy-2-propanol and 2,3-di-isopentoxy-1-propanol (8.4%), iso-pentanol (6.3%).

Workup

custompurged with nitrogen three times
customconsumption of iso-valeraldehyde and formation of glycerol monoethers 3-iso-pentoxy-1,2-propanediol and 2-isopentoxy-1,2-propanediol (82.0%, ratio 8.5), glycerol diethers 1,3-di-isopentoxy-2-propanol and 2,3-di-isopentoxy-1-propanol (8.4%), iso-pentanol (6.3%)

Sources & evidence

ORD record: ord-4a914d81f54f4a7c9b221532cc63eb9b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829229B2

Reaction notes

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