Adipic Acid → Beta-Isophorone

HRID 1415456Notes

Reaction equation

HRID 1415456 reaction equation
C(O)(=O)CCCCC(O)=O.[O:11]=[C:12]1[CH2:19][C:16]([CH3:18])([CH3:17])[CH2:15][C:14]([CH3:20])=[CH:13]1>>[CH3:20][C:14]1[CH2:13][C:12](=[O:11])[CH2:19][C:16]([CH3:18])([CH3:17])[CH:15]=1

Participants

3

Reactant 2

HCID 196Adipic AcidHCID 6544Isophorone

Product 1

HCID 10108Beta-Isophorone

Procedure

After the addition of 38 g. of adipic acid to 553 g. of isophorone, the mixture is heated to boiling at atmospheric pressure. The β-isophorone C formed is distilled off via a rectification attachment. The reflux is controlled such that 11 ml. of β-isophorone/isophorone mixture distill over per hour. The distillate collected after 50 hours (456 g.) consists of 91% β-isophorone and 9% isophorone. The β-isophorone is separated from the isophorone by repeated rectification at 68°-69° C/11 mm Hg. There are obtained 412 g. of pure β-isophorone and 42 g. of isophorone. The conversion of isophorone to β-isophorone comes to 428 g.

Workup

  1. additionAfter the addition of 38 g

Sources & evidence

ORD record
ord-a543d39b59894b69a742b627668d6751
Source dataset
uspto-grants-1977_01
Patent number
US04005145

Reaction notes

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