Butylene glycol diacetate → Acetic Acid

HRID 596150Notes

Reaction equation

HRID 596150 reaction equation
[C:1]([O:4]CC[CH2:7][CH2:8][O:9][C:10](=O)[CH3:11])(=[O:3])[CH3:2].C(OC(OC(=O)C)CCC)(=O)C>>[O:9]1[CH2:8][CH2:7][CH2:11][CH2:10]1.[C:1]([OH:4])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 69410Butylene glycol diacetateHCID 182019Butanediol, diacetate

Product 2

HCID 176Acetic AcidYield 93%HCID 8028TetrahydrofuranYield 90%

Procedure

The tube reactor, charged with 110 grams of alumina catalyst (1/8 inch pellets, Harshaw Al-0104T), is maintained at 250° C while 25.0 grams of 1,4-butanediol diacetate and 50 ml. of water are admitted to the evaporator simultaneously from different addition funnels over a 20 minute period. The aqueous effluent collected contains tetrahydrofuran, acetic acid, and about 10% of the original diacetate. The mixture is again taken through the tube. The effluent from this second pass contains, as found by quantitative glpc analysis, 0.3 grams of residual butanediol diacetate (1% unconverted), 9.2 grams of tetrahydrofuran (90% yield), and 15.9 grams of acetic acid (93% yield).

Workup

  1. additionThe tube reactor, charged with 110 grams of alumina catalyst (1/8 inch pellets, Harshaw Al-0104T)
  2. customof water are admitted to the evaporator simultaneously from different addition funnels over a 20 minute period
  3. customThe aqueous effluent collected

Sources & evidence

ORD record
ord-1734b51cfb9440c7b29b8f0c499a476c
Source dataset
uspto-grants-1977_03
Patent number
US04010171

Reaction notes

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