Tetrahydrofuran → Gamma-Butyrolactone

HRID 713829Notes

Reaction equation

HRID 713829 reaction equation
[H][H].[C:3](OC)(=[O:10])/[CH:4]=[CH:5]\[C:6]([O:8][CH3:9])=[O:7].O1CCCC1>O>[CH2:3]([OH:10])[CH2:4][CH2:5][CH2:6][OH:7].[C:6]1(=[O:7])[O:8][CH2:9][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 5271565Dimethyl maleateHCID 178418361HCID 178418361, compound2×

Product 2

HCID 7302Gamma-ButyrolactoneHCID 80641,4-Butanediol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The dialkyl maleate produced in the second esterification stage 13 is fed to a hydrogenation stage 17. For the hydrogenation, hydrogen 19 is also introduced into the hydrogenation stage 17. In the hydrogenation stage 17, the dimethyl maleate is reacted with the hydrogen to form tetrahydrofuran and optionally 1,4-butanediol and/or γ-butyrolactone with simultaneous formation of alkanol and water, as described, for example, in WO 88/00937, WO 91/01960, WO 03/006446 or WO 05/058855. The alkanol formed in the hydrogenation is the same alkanol as that which was introduced in the first esterification stage 9 and second esterification stage 13.

Sources & evidence

ORD record
ord-4bda3faa2a3f4f4fa952f63e78a6a6fc
Source dataset
uspto-grants-2015_11
Patent number
US09186599B2

Reaction notes

Loading…