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Sulfuric Acid → Epoxysuccinic acid

HRID 436909
Notes
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Reaction equation

HRID 436909 reaction equation
C([O-])(=O)/C=C\C([O-])=O.[Ca+2].[O:10]1[CH:15]([C:16]([O-:18])=[O:17])[CH:11]1[C:12]([O-:14])=[O:13].[Ca+2].[Ca].S(=O)(=O)(O)O>CC(C)=O>[O:10]1[CH:15]([C:16]([OH:18])=[O:17])[CH:11]1[C:12]([OH:14])=[O:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1118Sulfuric Acid3×HCID 5460341CalciumHCID 6916005Maleic acid, calcium saltHCID 13538056Calcium epoxysuccinate2×

Product 1

HCID 86022Epoxysuccinic acidYield 97%

Reagents, catalysts & solvents 1

HCID 180
Acetone
Solvent
2×

Conditions

Temperature
50 °C

Procedure

The epoxidation of acid calcium maleate was effected in accordance with Example 1. 50 g. of the calcium epoxysuccinate attained in this manner (calcium content 11.9% by weight) were suspended, with stirring, in 400 g. of 50% aqueous acetone. 15 g. of concentrated sulphuric acid were then added and the suspension was kept for 2 hours at 20° C. If the suspension is made in acetone alone, a corresponding amount of dilute sulphuric acid may be added instead of concentrated sulphuric acid. The suspension was then heated to 50° C. and, after being kept for 2 hours at this temperature, the calcium sulphate was filtered off and washed with water. The acetone was removed by distillation from the mixture of acetone and water, and the remaining aqueous epoxysuccinic acid solution was subjected directly to hydrolysis. From two moles of acid calcium epoxysuccinate, 512 g. of free epoxysuccinic acid were obtained, corresponding to a yield of 97% of the theoretical.

Workup

  1. waitafter being kept for 2 hours at this temperature
  2. filtrationthe calcium sulphate was filtered off
  3. washwashed with water
  4. customThe acetone was removed by distillation from the mixture of acetone and water
  5. customthe remaining aqueous epoxysuccinic acid solution was subjected directly to hydrolysis

Sources & evidence

ORD record
ord-3ae237c421dd4d15b204a533982db57a
Source dataset
uspto-grants-1977_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04028407

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes