Hydrogen Peroxide → cis-Epoxysuccinate

HRID 2225354

Reaction equation

HRID 2225354 reaction equation
[OH-:1].[Na+].[C:3]([OH:10])(=[O:9])/[CH:4]=[CH:5]\[C:6]([OH:8])=[O:7].OO>O.O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[C@@H:4]1([C:3]([OH:10])=[O:9])[O:1][C@@H:5]1[C:6]([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium Hydroxide2×HCID 444266Maleic Acid

Product 1

HCID 2734802cis-Epoxysuccinate

Reagents, catalysts & solvents 2

HCID 150191Sodium Tungstate DihydrateCatalystHCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

A solution was prepared by dissolving 67 grams of sodium hydroxide in 400 ml of water. To this solution were added 130 g of maleic acid while maintaining the solution at a temperature below 98° C. An aqueous solution of hydrogen peroxide (30%) was then added, followed by the addition of a solution containing 2.0 g of sodium tungstate dihydrate in 8.0 ml of water. The solution was heated in a 90° C. oil bath for 30 minutes and then cooled to ≤60° C. A solution containing 44 g of aqueous NaOH (50% by weight) was then added to bring the pH to 7.0. The product was analyzed by NMR, giving 14.7% by weight of cis-epoxysuccinic acid and 3.9% by weight of D,L-tartaric acid.

Workup

  1. customA solution was prepared
  2. temperaturewhile maintaining the solution at a temperature below 98° C
  3. additionfollowed by the addition of a solution
  4. temperaturecooled to ≤60° C
  5. additionwas then added

Sources & evidence

ORD record
ord-74c2f7d5e0604e748ae81c019376cb48
Source dataset
uspto-grants-1994_09
Patent number
US05344590

Linked notes

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