Acetoacetic Acid → Acetic Acid

HRID 1415442Notes

Reaction equation

HRID 1415442 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][C:7]([OH:9])=[O:8].C(OCCCCOC(=O)C)(=O)C.CC(CC(O)=O)=O.C(OC(OC(=O)C)CCC)(=O)C>O>[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]([OH:9])(=[O:8])[CH3:6]

Participants

7

Reactant 4

HCID 96Acetoacetic AcidHCID 69410Butylene glycol diacetateHCID 182019Butanediol, diacetateHCID 2287262-(Oxolan-2-yl)acetic acid

Product 2

HCID 176Acetic AcidYield 89%HCID 8028TetrahydrofuranYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The tube reactor is charged with 88.1 grams of Linde 13X zeolite (150 pellets, pretreated at 200° C. with a tetrahydrofuran-acetic acid vapor mixture) and maintained at 190°-230° C. while 50.0 grams of 1,4-butanediol diacetate and 60 ml. of water are copassed, as in Examples 1-3, over a 1 hour period. The effluent is recycled three times until the diacetate is essentially converted. Quantitative glpc analysis of the final effluent shows the presence of 0.4 grams of butanediol diacetate (1% recovery), 9.5 grams of tetrahydrofuran (47% yield) and 30.4 grams of acetic acid (89% yield). A considerable amount of low boiling material is produced using this method.

Sources & evidence

ORD record
ord-2dfa87c741ac498ba5b1cd06c1ec92e2
Source dataset
uspto-grants-1977_01
Patent number
US04005113

Reaction notes

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