Butyraldehyde, cyclic acetal with glycerol → 3-Butoxy-1,2-propanediol

HRID 1050892Notes

Reaction equation

HRID 1050892 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][O:6][C@@H:5]([CH2:8][CH2:9][CH3:10])[O:4]1.OC1COC(CCC)OC1>[Pd].OCC(CO)O>[CH2:5]([O:6][CH2:7][CH:3]([OH:4])[CH2:2][OH:1])[CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 347826Butyraldehyde, cyclic acetal with glycerolHCID 12627409[(2R,4R)-2-Propyl-1,3-dioxolan-4-yl]methanol

Product 1

HCID 2630273-Butoxy-1,2-propanediol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 753GlycerolSolvent

Conditions

Temperature
200 °C

Procedure

16.6 g of an equimolar mixture of cis/trans-4-hydroxymethyl-2-propyl-1,3-dioxolane and 5-hydroxy-2-propyl-1,3-dioxane were combined with 100 g of glycerin (glycerol) in a 300 mL stainless steel autoclave. 2.0 g of 5% Pd/C catalyst were added and the autoclave was sealed. The reactor was heated to 200° C. The reactor was then brought to an operating pressure of 6.89 MPa and stirring commenced at 750 rpm. Pressure was maintained through the duration of the experiment. After 2 h, the autoclave was cooled and remaining gas vented. The autoclave was opened, its contents filtered, and the filtrate analyzed by gas chromatography (GC). 76% conversion of the acetal mixture was observed. Upon analysis of the results, the mixture was found to demonstrate 26.1% selectivity to 2-butoxy-1,3-propanediol, 71.7% 3-butoxy-1,2-propanediol, and the balance n-butanol.

Workup

  1. customthe autoclave was sealed
  2. temperaturePressure was maintained through the duration of the experiment
  3. temperaturethe autoclave was cooled
  4. filtrationits contents filtered

Sources & evidence

ORD record
ord-2b61818519914cdeb27fa7406b072f44
Source dataset
uspto-grants-2016_07
Patent number
US09388105B2

Reaction notes

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