Oxalic Acid → Urea oxalate

HRID 426538Notes

Reaction equation

HRID 426538 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[OH2:7].O.C(O)(=O)C(O)=O.P(O)(O)(O)=O.[NH2:20][C:21]([NH2:23])=O.P(=O)(O)(O)O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2]>O>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[NH2:20][C:21]([NH2:23])=[O:7]

Participants

7

Reactant 5

HCID 971Oxalic AcidHCID 1004Phosphoric AcidHCID 20994Urea phosphoric acid2×HCID 61373Oxalic acid dihydrateHCID 10207414Fluorapatite (Ca5F(PO4)3)

Product 1

HCID 13685621Urea oxalateYield 0.03%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of oxalic acid consisting of 138.7 grams of oxalic acid dihydrate dissolved in 200 mL water was warmed to 60° C. and treated with 316 grams of urea phosphate made from wet-process phosphoric acid made from calcined North Carolina phosphate rock. The urea phosphate was added gradually over a 10-minute period with stirring while maintaining the temperature at 55°-60° C. Stirring and heating (at 60°-70° C.) was continued for 20 minutes. The hot mixture was filtered, and the clear, pale green filtrate was cooled to 5° C. and refiltered. The second filtrate weighed 377.2 grams, and it contained 32.1 percent P2O5, 1.82 percent N, 1.3 percent oxalic acid, 0.04 percent Al, 0.11 percent Fe, 0.08 percent Mg, and SO4. This corresponds to removal of 74 to 80 percent of the Al, Fe, Mg, F, and SO4 impurities originally present in the phosphoric acid used to make the urea phosphate. The urea oxalate filter cake from the first filtration was washed with about 200 mL of cold water and then dried, yielding 112.7 grams of urea oxalate containing 0.03 percent P2O5, 26.4 percent nitrogen, and 43.3 percent oxalic acid (theoretical composition of urea oxalate is 26.95 percent nitrogen and 42.86 percent oxalic acid). X-ray diffraction analysis showed that it was homogeneous as urea oxalate. The wash from the urea oxalate (first filter cake) weighed 220.0 grams, and it contained 5.6 percent P2O5, 1.17 percent N, and 2.3 percent oxalic acid. The second filtration yielded 66.0 grams of dried, unwashed crystals which contained 5.0 percent P2O5, 20.9 percent N, and 47.8 percent oxalic acid.

Workup

  1. temperaturewhile maintaining the temperature at 55°-60° C
  2. stirringStirring
  3. temperatureheating (at 60°-70° C.)
  4. filtrationThe hot mixture was filtered
  5. temperaturethe clear, pale green filtrate was cooled to 5° C.
  6. customThis corresponds to removal of 74 to 80 percent of the Al, Fe, Mg, F, and SO4 impurities originally present in the phosphoric acid
  7. filtrationThe urea oxalate filter cake
  8. filtrationfrom the first filtration
  9. washwas washed with about 200 mL of cold water
  10. customdried

Sources & evidence

ORD record
ord-d5c2003725544f8887e5e6e71f8b1d34
Source dataset
uspto-grants-1979_10
Patent number
US04169882

Reaction notes

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