Oxygen → 3-(Chloromethyl)oxolane-2,5-dione

HRID 1579570Notes

Reaction equation

HRID 1579570 reaction equation
[Cl-:1].[K+].O=O.[C:5]1(=[O:12])[O:11][C:9](=[O:10])[CH:8]=[C:6]1[CH3:7].CC1CC(=O)OC1=O>O>[Cl:1][CH2:7][CH:6]1[CH2:8][C:9](=[O:10])[O:11][C:5]1=[O:12]

Participants

6

Reactant 4

HCID 977OxygenHCID 4873Potassium ChlorideHCID 12012Citraconic AnhydridesHCID 20051Methylsuccinic anhydride

Product 1

HCID 135928303-(Chloromethyl)oxolane-2,5-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Next, the reacted gas was passed through a layer in a Pyrex tube (diameter: 2.5cm) packed with 20cc of an oxychlorinating catalyst comprising silica-alumina carrying 5% by weight of potassium chloride and 5% by weight of cupric chloride, at a temperature of 250°C while introducing oxygen in an amount of 1000cc/hour. The water generated was trapped in a vessel and the chlorine gas recovered was circulated, whereby the reaction was carried out for 2 hours. After completion of the reaction, the product was analyzed using gas chromatography, and it was confirmed that the product contained 7.4g of citraconic acid anhydride and 1.8g of methylsuccinic acid anhydride. In addition, a small amount of chloromethylsuccinic acid anhydride was formed.

Workup

  1. customNext, the reacted gas was passed through a layer in a Pyrex tube
  2. customthe chlorine gas recovered
  3. customAfter completion of the reaction

Sources & evidence

ORD record
ord-92d04c18692742eb8bad6d71f8b2af16
Source dataset
uspto-grants-1976_01
Patent number
US03931241

Reaction notes

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