Hydrochloric Acid → trans-Aconitic acid

HRID 904908

Reaction equation

HRID 904908 reaction equation
[OH-].[Ca+2].[OH-].Cl.[C:5]([OH:17])(=[O:16])[CH:6]([CH:8]([CH2:12][C:13]([OH:15])=[O:14])[C:9]([OH:11])=[O:10])O>O>[CH2:12]([C:13]([OH:15])=[O:14])/[C:8](/[C:9]([OH:11])=[O:10])=[CH:6]\[C:5]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1198Isocitric AcidHCID 6093208Calcium Hydroxide2×

Product 1

HCID 444212trans-Aconitic acidYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

Thirty one grams (0.1 mole) of product prepared as in Example I-B is mixed with 200 mls water. Thirty grams (0.4 mole) calcium hydroxide is added slowly while the pH of the reaction medium is maintained at 10-10.5 and the temperature is kept between 70° and 75° C. After the addition of calcium hydroxide is complete, the reaction mixture is stirred at 75° C. for an additional two hours and then cooled. 90 grams of a 20% by weight hydrochloric acid solution is added slowly to a pH of 1.3 and the resulting solution is then filtered. The filtrate is evaporated to dryness in vacuo and the residue extracted with acetone. The acetone extract is filtered and 19.5 grams of product consisting of 53.5% (60% yield) transaconitic acid and 5.8% of a mixture of lactones of isocitric acid and alloisocitric acid.

Workup

  1. temperatureis maintained at 10-10.5
  2. customis kept between 70° and 75° C
  3. temperaturecooled
  4. filtrationthe resulting solution is then filtered
  5. customThe filtrate is evaporated to dryness in vacuo
  6. extractionthe residue extracted with acetone
  7. extractionThe acetone extract
  8. filtrationis filtered

Sources & evidence

ORD record
ord-08434ff1ebe44b05a3d415375d40b38a
Source dataset
uspto-grants-1983_12
Patent number
US04420621

Linked notes

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