Levulinic Acid → Pentane-1,4-diol

HRID 1418723

Reaction equation

HRID 1418723 reaction equation
C1NC2NC(N)=NC(=[O:14])C=2N2C1CN(C1C=CC(C(N[C@H:25]([C:31]([OH:33])=[O:32])[CH2:26][CH2:27][C:28](O)=O)=O)=CC=1)C2.[C:34](O)(=[O:40])[CH2:35][CH2:36][C:37]([CH3:39])=[O:38]>[O-2].[Cr+3].[Cu+2]>[C:31]1(=[O:33])[O:32][CH:27]([CH3:28])[CH2:26][CH2:25]1.[CH2:34]([OH:40])[CH2:35][CH2:36][CH:37]([OH:38])[CH3:39].[OH2:14]

Participants

6

Reactant 2

HCID 11579Levulinic AcidHCID 178508906HCID 178508906, compound

Product 3

HCID 962WaterYield 22%HCID 7921Gamma-ValerolactoneYield 11%HCID 79083Pentane-1,4-diolYield 44%

Reagents, catalysts & solvents 1

HCID 131711404Copper-chromium oxideCatalyst

Procedure

Direct production of MTHF from levulinic acid is not reported in the literature except as a minor byproduct [4]. Copper-chromium oxide was used to catalyze the hydrogenation in a two stage manner at 245° C. and 300° C. and required about 80 minutes. The reaction yielded 11% gamma-valerolactone and 44% 1,4-pentanediol with a 22% yield of a water byproduct with the "odor of a alpha-methyl tetrahydrofuran", but no quantitative analysis of the water byproduct was reported, (estimated 4.5 mol % yield of MTHF in the water byproduct).

Workup

  1. customat 245° C.
  2. custom300° C.
  3. customabout 80 minutes

Sources & evidence

ORD record
ord-e52f987c1f4744d49e0e5b7dd11a6c1a
Source dataset
uspto-grants-1999_03
Patent number
US05883266

Linked notes

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