Maleic Anhydride → 1,4-Butanediol

HRID 2297088Notes

Reaction equation

HRID 2297088 reaction equation
[OH-].[Na+].[C:3]1(=O)[O:8][C:6](=[O:7])[CH:5]=[CH:4]1>[Ni].[Re](O)(=O)(=O)=O.O1CCCC1>[C:6]1(=[O:7])[O:8][CH2:3][CH2:4][CH2:5]1.[CH2:3]([OH:8])[CH2:4][CH2:5][CH2:6][OH:7]

Participants

7

Reactant 2

HCID 7923Maleic AnhydrideHCID 14798Sodium Hydroxide

Product 2

HCID 7302Gamma-ButyrolactoneYield 25.9%HCID 80641,4-ButanediolYield 26.9%

Reagents, catalysts & solvents 3

HCID 935NickelCatalyst2×HCID 83718Perrhenic acidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A free-flowing, pelletable catalyst mixture is prepared by the procedure described in EP 0 648 534 A1 for a catalyst consisting of 1000 g of 50%Ni and 50%Al alloy powder, 7.5 g of pure nickel powder (99%Ni, and d50=21 μm), and 50 g of ethylene bis-stearoylamide. Tablets with the diameter of 4 mm and a thickness of 4 mm are compressed from this mixture. The shaped items are calcined for 2 h at 700° C. The tablets are activated in 20% strength caustic soda solution for 2 hours at 80° C. after calcination. This catalyst is doped to the level of 6.0% Re by exposing the catalyst for 240 h to a stirred perrhenic acid solution that is adjusted to a pH of 10.5 before adding the catalyst. Maleic anhydride is hydrogenated in the presence of the catalyst as described in Application Example 1 (infra) yielding 25.9% gamma-butyrolactone, 3.71% tetrahydrofuran, and 26.9% 1,4-butanediol after a reaction time of 5 hours.

Workup

  1. customA free-flowing, pelletable catalyst mixture is prepared by the procedure
  2. customfor 240 h
  3. additionbefore adding the catalyst

Sources & evidence

ORD record
ord-37a9b85440ed478dbbf37575cf32907f
Source dataset
uspto-grants-2002_12
Patent number
US06489521B2

Reaction notes

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