Ammonia → Monoguanidine phosphate

HRID 1680377Notes

Reaction equation

HRID 1680377 reaction equation
C([NH:3][C:4]([NH2:6])=[NH:5])#N.[P:7](=[O:11])([OH:10])([OH:9])[OH:8].P(O)(O)(O)=O.C(NC(N)=N)(=O)N.C(O)C(O)C.C(=O)=O.N>>[P:7]([OH:11])([OH:10])([OH:9])=[O:8].[NH2:5][C:4]([NH2:6])=[NH:3]

Participants

7

Reactant 6

HCID 222AmmoniaHCID 280Carbon DioxideHCID 1004Phosphoric AcidHCID 1030Propylene GlycolHCID 178418324HCID 178418324, compoundHCID 178513043HCID 178513043, compound

Product 1

HCID 160593Monoguanidine phosphate

Conditions

Temperature
25 °C

Procedure

Cyanoguanidine 336 parts (4.00 moles) is mixed with 603.2 parts (4.00 moles) of 65.0% phosphoric acid in a stainless steel beaker having a volume about four times that of the reaction mixture. The mixture is stirred with a spatula while maintaining the temperature at 25° C. The resulting smooth fluid slurry is heated in an oil bath from 25° to 90° C. in 0.35 hour when the slurry clears to a solution and boils vigorously. Within 2 minutes the boiling ceases and the liquid solidifies. To the solid carbamoylguanidine phosphate is added 1.9 parts (0.2%) of the polyoxyethylated propylene glycol block copolymer of molecular weight 1,045 identified in Example 1 as a viscosity reducer and foam controller. The heating is continued and at about 180° C. the solid begins to soften and at 190°-195° C. the cake begins to breakup with stirring. At about 200° C., the melt begins to foam (CO2 and NH3 evolution) and by 225° C. has become a uniform melt free of lumps with reduced foaming. The time required to heat from 90° to 225° C. is 1.3 hours. After 0.7 hour at 225° C. foaming has largely subsided. Heating at 225° C. is continued for an additional one hour. The beaker is then removed from the bath and cooled to room temperature. The product, a faint tan opaque glass has a pH of 6.5 (1% aqueous slurry), an amorphous solids content of 3.9% and a guanidine content of 47.9%. The conversion yield of cyanoguanidine to guanidine is 119.2% based on the stoichiometry, 1 cyanoguanidine→1 guanidine. The weight loss at 220° C. for 1 hour is 0.4%. The product is ground to a coarse powder in a Wiley Mill using a 6-mm screen.

Workup

  1. temperatureThe resulting smooth fluid slurry is heated in an oil bath from 25° to 90° C. in 0.35 hour when the slurry
  2. customis continued and at about 180° C.
  3. customto soften and at 190°-195° C.
  4. stirringwith stirring
  5. customAt about 200° C.
  6. temperatureto heat from 90° to 225° C.
  7. waitis 1.3 hours
  8. waitAfter 0.7 hour at 225° C. foaming has largely subsided
  9. temperatureHeating at 225° C.
  10. waitis continued for an additional one hour
  11. customThe beaker is then removed from the bath
  12. temperaturecooled to room temperature
  13. waitThe weight loss at 220° C. for 1 hour is

Sources & evidence

ORD record
ord-16dba26af20e419896a1e0e6fc14c0f1
Source dataset
uspto-grants-1981_06
Patent number
US04273687

Reaction notes

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