Glucaric Acid → Adipic Acid

HRID 62568

Reaction equation

HRID 62568 reaction equation
[O:1]=[C:2]([OH:14])[C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([C:11]([OH:13])=[O:12])O)O)O)O.O=C(O)[C@@H]([C@H]([C@H]([C@@H](C(O)=O)O)O)O)O>[Re]>[C:11]([OH:13])(=[O:12])[CH2:9][CH2:7][CH2:5][CH2:3][C:2]([OH:14])=[O:1]

Participants

4

Reactant 2

HCID 33037Glucaric AcidHCID 3037582Galactaric acid

Product 1

HCID 196Adipic Acid

Reagents, catalysts & solvents 1

HCID 23947RheniumCatalyst

Procedure

Further, as described above, the starting material (glucaric acid or galactaric acid), rhenium catalyst, and acid catalyst are added to the reaction solvent, and reacted together at a proper temperature for a proper reaction time, then separated and purified with a conventional method (e.g., purification with silica column) to obtain glucaric acid ester or galactaric acid ester as an intermediate of adipic acid. In one embodiment, the reaction temperature ranges from 100 to 200° C., and the reaction time is 12 to 24 hours.

Workup

  1. additionare added to the reaction solvent
  2. customreacted together at a proper temperature for a proper reaction time
  3. customseparated
  4. custompurified with a conventional method (e.g., purification with silica column)

Sources & evidence

ORD record
ord-e4d92eb81e1047428d952ffc9a9ab295
Source dataset
uspto-grants-2016_09
Patent number
US09447012B2

Linked notes

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