Reaction #992675

ord-5e992babb9514177bb334f7e36a2c9ad

Reaction equation

O=C(O)C(=O)O
Oxalic acid
N=C(N)NN.O=C(O)O
Aminoguanidine bicarbonate
N=C(N)N.O=C(O)O
guanidine carbonate
→
NC(N)=[NH2+].NC(N)=[NH2+].O=C([O-])C(=O)[O-]
Guanidinium Oxalate

Reactants

O=C(O)C(=O)O
Oxalic acid
N=C(N)NN.O=C(O)O
Aminoguanidine bicarbonate
N=C(N)N.O=C(O)O
guanidine carbonate

Reagents

None

Solvents

O
water

Conditions

Temperature
90°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherto avoid bubbling over the sides of the beaker due to the evolution of carbon dioxide during the reaction
  2. 2
    workup.STIRRINGThe reaction was stirred at room temperature overnight (approximately 24 hours)
  3. 3
    OtherThe water was removed from the reaction mixture in vacuo
  4. 4
    OtherThe product was recovered as a crystalline white solid

Procedure

Oxalic acid (200.0 g, 2.22 mol) was weighed into a 2-liter beaker with a magnetic stir bar and dissolved in 1500 ml of distilled water. Aminoguanidine bicarbonate (362.8 g, 2.67 mol) and guanidine carbonate (160.1 g, 0.89 mol) were added in portions with stirring as to avoid bubbling over the sides of the beaker due to the evolution of carbon dioxide during the reaction. The reaction was stirred at room temperature overnight (approximately 24 hours). The water was removed from the reaction mixture in vacuo with heating to approximately 90° C. for 4 hours. The product was recovered as a crystalline white solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08012277B2uspto-grants-2011_09