Butanal → n-Butyraldehyde Tetraethylene Glycol

HRID 74120Notes

Reaction equation

HRID 74120 reaction equation
[CH:1](=[O:5])[CH2:2][CH2:3][CH3:4].[CH2:6]([OH:18])[CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][OH:17].C(O)COCCOCCOCCOCCCC>[Pd].C(O)CCC>[CH:1](=[O:5])[CH2:2][CH2:3][CH3:4].[CH2:16]([OH:17])[CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][OH:18]

Participants

6

Reactant 3

HCID 261ButanalHCID 8200Tetraethylene GlycolHCID 737913,6,9,12-Tetraoxahexadecan-1-ol

Product 1

HCID 87349964n-Butyraldehyde Tetraethylene Glycol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 2631-ButanolSolvent

Conditions

Temperature
180 °C

Procedure

n-Butyraldehyde (1.8 g, 2.25 ml; 0.025 mol), tetraethylene glycol (97.1 g, 86.3 ml; 0.5 mol), and 0.09 g of 10% Pd/C are charged to a 150 ml Parr reactor. The system is purged with nitrogen three times. Then 500 psi of hydrogen is charged, the reactor is heated to 180° C., and set 1000 psi of hydrogen. After 4 hrs at 180° C. and 1000 psi n-butyraldehyde reacts completely, and GC analysis shows formation of 3,6,9,12-tetraoxahexadecanol (91.2%), n-butanol (4.8%) and 5,8,11,14,17-pentaoxauneicosane (1.1%).

Workup

  1. customThe system is purged with nitrogen three times
  2. additionThen 500 psi of hydrogen is charged
  3. custom1000 psi n-butyraldehyde reacts completely

Sources & evidence

ORD record
ord-515c6d0121644038890d235028bf555f
Source dataset
uspto-grants-2014_09
Patent number
US08829229B2

Reaction notes

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