Carbon Dioxide → Adipic Acid

HRID 1720840Notes

Reaction equation

HRID 1720840 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-d5c45e0b1ef44f42917d5386d7968207
Source dataset
uspto-grants-1996_04
Patent number
US05507882

Reaction notes

Loading…