1-Butanol → 2-Butoxyethanol

HRID 1980007Notes

Reaction equation

HRID 1980007 reaction equation
[CH2:1]([CH:4]1[O:8][CH2:7][CH2:6][O:5]1)[CH2:2][CH3:3].[C:9]1([CH:16]=[CH:15][C:13]([OH:14])=CC=1)O.P(=O)(O)(O)O.C(O)CCC>[Pd].C(O)CO>[CH2:4]([O:5][CH2:6][CH2:7][OH:8])[CH2:1][CH2:2][CH3:3].[CH2:4]([O:5][CH2:6][CH2:7][O:14][CH2:13][CH2:15][CH2:16][CH3:9])[CH2:1][CH2:2][CH3:3]

Participants

8

Reactant 4

HCID 2631-ButanolHCID 785HydroquinoneHCID 1004Phosphoric AcidHCID 1798322-Propyl-1,3-dioxolane2×

Product 2

HCID 81332-ButoxyethanolHCID 8188Ethylene glycol dibutyl ether

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 174Ethylene GlycolSolvent

Procedure

The mixture consisting of 50 g (0.431 moles) of 2-propyl-1,3-dioxolane and 250 g of ethylene glycol is hydrogenolyzed in a mechanically agitated autoclave of 1-liter capacity, in the presence of 9 mg of hydroquinone, 5 g of palladium catalyst deposited on carbon at a rate of 5% of palladium by weight and of 210 mg of concentrated phosphoric acid. After 3 hours at a temperature of 170° C. under a hydrogen pressure kept constant at 30 bars, the degree of conversion of the 2-propyl dioxolane reaches 98.2%; 46.1 g (0.390 moles) of 2-butoxy-1-ethanol are produced besides 2.35 g (0.0135 moles) of 1,2-dibutoxy ethane and 0.31 g (0.004 moles) of normal butanol.

Sources & evidence

ORD record
ord-06738800656b47bf80981ed508d1dc86
Source dataset
uspto-grants-1984_11
Patent number
US04484009

Reaction notes

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