Formaldehyde → HCID 21285052, compound

HRID 1772566Notes

Reaction equation

HRID 1772566 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:8]1[C:15]([NH2:16])=[N:14][C:12]([NH2:13])=[N:11][C:9]=1[NH2:10].C=O>C(N(CC)CC)C>[N:8]1[C:15]([NH2:16])=[N:14][C:12]([NH2:13])=[N:11][C:9]=1[NH2:10].[CH2:1]=[O:7].[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 712Formaldehyde2×HCID 996PhenolHCID 7955Melamine

Product 1

HCID 21285052HCID 21285052, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
75 °C

Procedure

The process for Example 7 was initiated by charging 593.4 g phenol (6.31 moles) and 0.86 g of triethylamine into a reaction vessel to form a reaction mixture. The reaction mixture was heated to 75° C., and 75.6 g melamine (0.60 moles) was added and mixed for 15 minutes. 53.81 g of 50.17% aqueous formaldehyde (50% of total charge) was added over 30 minutes. 53.61 g of 50.17% aqueous formaldehyde (50% of total charge) was added over 32 minutes. The reaction mixture was maintained at 75° C. for 2 hours and then heated to 85° C. before maintaining the temperature for 30 minutes. The reaction mixture was atmospherically distilled to 110° C. and the temperature was maintained at 110° C. for 3 hours, before reducing the reaction mixture temperature to 100° C. under reflux mode. 4.21 g of benzoic acid slowly over 10 minutes was added and mixed for over 5 minutes. The reaction mixture was then atmospherically distilled to 110° C. and the temperature maintained at 110° C. for 2 hours. The reaction mixture was then atmospherically distilled to 150° C. and the temperature maintained at 150° C. for 2 hours before increasing the temperature to 165° C. while continuing to distill atmospherically. Next, the reaction mixture was under a gradually increasing vacuum over 1.5 hours to full vacuum of at least 27 inches while maintaining a temperature of 163°-165° C. before heating the reaction mixture to 175° C. under full vacuum. Further, the process was concluded by discharging the product (293.6 g) and the vacuum distillate (383.4 g) from the reaction vessel.

Workup

  1. customto form a reaction mixture
  2. additionmixed for 15 minutes
  3. temperatureThe reaction mixture was maintained at 75° C. for 2 hours
  4. temperatureheated to 85° C.
  5. temperaturebefore maintaining the temperature for 30 minutes
  6. distillationThe reaction mixture was atmospherically distilled to 110° C.
  7. temperaturethe temperature was maintained at 110° C. for 3 hours
  8. customto 100° C.
  9. temperatureunder reflux mode
  10. addition4.21 g of benzoic acid slowly over 10 minutes was added
  11. additionmixed for over 5 minutes
  12. distillationThe reaction mixture was then atmospherically distilled to 110° C.
  13. temperaturethe temperature maintained at 110° C. for 2 hours
  14. distillationThe reaction mixture was then atmospherically distilled to 150° C.
  15. temperaturethe temperature maintained at 150° C. for 2 hours
  16. temperaturebefore increasing the temperature to 165° C.
  17. distillationto distill atmospherically
  18. temperaturea gradually increasing vacuum over 1.5 hours to full vacuum of at least 27 inches
  19. temperaturewhile maintaining a temperature of 163°-165° C.
  20. temperaturebefore heating the reaction mixture to 175° C. under full vacuum

Sources & evidence

ORD record
ord-7b22cc6456c441e98fe8dd3cb83bef6d
Source dataset
uspto-grants-2016_02
Patent number
US09249251B2

Reaction notes

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