Carbon Dioxide → trans-Aconitic acid

HRID 893895

Reaction equation

HRID 893895 reaction equation
[CH:1](C([O-])=O)([C:10]([O-:12])=[O:11])[CH:2]([C:7]([O-:9])=[O:8])[CH2:3][C:4]([O-:6])=[O:5].[Na+].[Na+].[Na+].[Na+].Cl.C(=O)=O>O>[CH2:3]([C:4]([OH:6])=[O:5])/[C:2](/[C:7]([OH:9])=[O:8])=[CH:1]\[C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 20562404Tetrasodium propane-1,1,2,3-tetracarboxylate

Product 1

HCID 444212trans-Aconitic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Nine grams of the product as prepared in Example 19, i.e. tetrasodium propane-1,1,2,3-tetracarboxylate, is dissolved in 100 mls water and acidified with dilute HCl (10%). Liberation of CO2 is instantaneous. The residue, after evaporation of water, is extracted with acetone. The acetone is evaporated to leave a residue consisting of a 1:1 by weight mixture of cis:trans aconitric acid. The structure of the product is confirmed by NMR analysis (D2O):

Workup

  1. customThe residue, after evaporation of water
  2. extractionis extracted with acetone
  3. customThe acetone is evaporated
  4. customto leave a residue
  5. additionconsisting of a 1:1 by weight mixture of cis

Sources & evidence

ORD record
ord-a3c67fedd8c949fcacffbd4aff51b9bf
Source dataset
uspto-grants-1981_08
Patent number
US04282156

Linked notes

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