Hydroxylamine → Hydroxylammonium oxalate (2:1)

HRID 247356Notes

Reaction equation

HRID 247356 reaction equation
[NH2:1][OH:2].OS(O)(=O)=O.[C:8]([OH:13])(=[O:12])[C:9]([OH:11])=[O:10]>CO>[C:8]([O-:13])(=[O:12])[C:9]([O-:11])=[O:10].[OH:2][NH3+:1].[OH:2][NH3+:1]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 971Oxalic AcidHCID 1118Sulfuric Acid

Product 1

HCID 6452062Hydroxylammonium oxalate (2:1)Yield 94.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of hydroxylamine in methanol (680 mL) as in Example 27 was used (pH 11.8). Conc. H2SO4 was slowly added to adjust the pH to 8.0 and the thin white precipitat formed was filtered off and the clear filtrate placed in a 1 liter Erlenmeyer flask. A magnetic stirring bar was introduced and the flask was placed in an ice-water bath. Oxalic acid (45 g; 0.5 mol) dissolved in methanol (100 mL) was slowly added with cooling and stirring. A thick white slurry was produced and this was filtered and the crude white solid (84.8 g) was collected. A portion (25 g) of this solid was recrystallized from hot water to produce white crystalline hydroxylammonium oxalate (M.P. 192° C. with decomposition). Yield 94.6%.

Workup

  1. customthe thin white precipitat
  2. customformed
  3. filtrationwas filtered off
  4. additionA magnetic stirring bar was introduced
  5. customthe flask was placed in an ice-water bath
  6. additionwas slowly added
  7. temperaturewith cooling
  8. customA thick white slurry was produced
  9. filtrationthis was filtered
  10. customthe crude white solid (84.8 g) was collected
  11. customA portion (25 g) of this solid was recrystallized from hot water

Sources & evidence

ORD record
ord-b89871412ad7479cbea14fd82912cf88
Source dataset
uspto-grants-1987_11
Patent number
US04707294

Reaction notes

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