Bis(2-ethylhexyl) maleate → 2-Ethylhexanol

HRID 2199078Notes

Reaction equation

HRID 2199078 reaction equation
[C:1](OCC(CC)CCCC)(=[O:15])/[CH:2]=[CH:3]\[C:4]([O:6][CH2:7][CH:8]([CH2:13][CH3:14])[CH2:9][CH2:10][CH2:11][CH3:12])=[O:5].[H][H]>C(C(CCCC)CO)C>[CH2:1]([OH:15])[CH2:2][CH2:3][CH2:4][OH:5].[CH2:13]([CH:8]([CH2:9][CH2:10][CH2:11][CH3:12])[CH2:7][OH:6])[CH3:14]

Participants

5

Reactant 2

HCID 5365125Bis(2-ethylhexyl) maleateHCID 178418361HCID 178418361, compound

Product 2

HCID 77202-EthylhexanolHCID 80641,4-Butanediol

Reagents, catalysts & solvents 1

HCID 77202-EthylhexanolSolvent

Procedure

The resulting solution of di-(2-ethylhexyl) maleate in 2-ethylhexan-1-ol is treated with hydrogen, in a trickle procedure, over a Cu/Mg silicate catalyst, at 190° C. and under a pressure of 200 bar, and the ester is cleaved to give butane-1,4-diol and 2-ethylhexanol. The mean space-time yield in a 3,300 hour experiment is 40 g of butanediol per liter per hour.

Sources & evidence

ORD record
ord-6669d7cbc0fd4c8e975894f6374fb629
Source dataset
uspto-grants-1982_11
Patent number
US04361710

Reaction notes

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