Carbon Dioxide → Adipic Acid

HRID 1084285Notes

Reaction equation

HRID 1084285 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3](O)=O.[C:8](=[O:10])=[O:9].[C:11]([OH:18])(=[O:17])[CH2:12][CH2:13][C:14]([OH:16])=[O:15].[C:19]1(=O)[O:24][C:22](=[O:23])[CH2:21][CH2:20]1>>[C:14]([OH:16])(=[O:15])[CH2:13][CH2:12][CH2:3][CH2:2][C:1]([OH:7])=[O:6].[C:22]([OH:24])(=[O:23])[CH2:21][CH2:20][CH2:19][C:8]([OH:10])=[O:9].[C:11]([OH:18])(=[O:17])[CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 867Malonic AcidHCID 1110Succinic AcidHCID 7922Succinic anhydride

Product 3

HCID 196Adipic AcidHCID 743Glutaric AcidHCID 1110Succinic Acid

Procedure

Elsewhere, that treatise notes that malonic acid loses carbon dioxide on heating above its melting point, and in aqueous solution, undergoes decarboxylation at 70° C. (vol. 14: 794-795); that succinic acid sublimes when heated below its 188° C. melting point, dehydrates at its melting point, and forms a cyclic anhydride, succinic anhydride having mp 119.6° C. (vol. 21: 848-849); and that adipic acid, unlike glutaric acid and succinic acid, does not readily form a cyclic anhydride, but decomposes to cyclopentanone above 225° C. (vol. 1: 510-513).

Workup

  1. temperatureon heating above its
  2. customat 70° C.

Sources & evidence

ORD record
ord-3ef6f013924b490c8b9ad7189b60e805
Source dataset
uspto-grants-1991_04
Patent number
US05004509

Reaction notes

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