Oxalic Acid → Acrylic anhydride

HRID 1906706Notes

Reaction equation

HRID 1906706 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].C(O[C:10]([CH3:12])=[CH2:11])(C)=C.C(O)(=O)C(O)=[O:15]>C(Cl)Cl>[C:1]([O:5][C:12](=[O:15])[CH:10]=[CH2:11])(=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 6581Acrylic AcidHCID 13483800Bisisopropenyl ether

Product 1

HCID 74919Acrylic anhydride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acrylic acid (1.47 g, 0.02 mole), diisopropenyl ether (0.99 g, 0.01 mole) and oxalic acid (0.008 g, 8.9×10-5 moles) were mixed in a nitrogen-filled 10-ml volumetric flask. A 30-μl aliquot of this mixture was transferred to a nuclear magnetic resonance tube, mixed with CDCl3 (0.5 ml), methylene chloride (10 μ) and tetramethylsilane. After 24.5 hours, the sample in the nuclear magnetic resonance tube showed that the reaction was almost complete as the acid was nearly consumed. The amount of acrylic anhydride produced was 1.5:1 to that of the 2,2-propane diacrylate. Conversely the mixture in the original volumetric flask had a much lower conversion of reactants to products and almost no anhydride. After 14 days, the amount of acrylic anhydride in the nuclear magnetic resonance tube increased while that in the volumetric flask did not. The ratio of acrylic anhydride to 2,2-propane diacrylate was 3.3:1.

Workup

  1. additionfilled 10-ml volumetric flask
  2. customA 30-μl aliquot of this mixture was transferred to a nuclear magnetic resonance tube
  3. customwas nearly consumed

Sources & evidence

ORD record
ord-3368044ebe81404793d63d2bc170c085
Source dataset
uspto-grants-1987_03
Patent number
US04654174

Reaction notes

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