Benzoic Acid → HCID 21285052, compound

HRID 1772561Notes

Reaction equation

HRID 1772561 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C1C=CC=CC=1.[N:17]1[C:24]([NH2:25])=[N:23][C:21]([NH2:22])=[N:20][C:18]=1[NH2:19].C=O>>[N:17]1[C:24]([NH2:25])=[N:23][C:21]([NH2:22])=[N:20][C:18]=1[NH2:19].[CH2:1]=[O:7].[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 243Benzoic AcidHCID 712FormaldehydeHCID 996PhenolHCID 7955Melamine

Product 1

HCID 21285052HCID 21285052, compound

Conditions

Temperature
80 °C

Procedure

The process for Example 1 was initiated by charging 546.0 grams (g) phenol (5.80 moles), 1.1 g benzoic acid (0.2% of phenol), and 79.1 g melamine (0.63 moles) into a reaction vessel to form a reaction mixture. The reaction mixture was heated to 80° C., and 55.8 g of 50.4% aqueous formaldehyde (60% of total charge) was added over 40 minutes. The reaction mixture was atmospherically distilled while heating to 123° C., and then maintaining the 123° C. temperature for 2 hours, followed by reducing the reaction mixture temperature to 80° C. 37.2 g of 50.4% aqueous formaldehyde (40% of total charge) was added over 30 minutes to the reaction mixture and then atmospherically distilling the reaction mixture to 123° C., maintaining the temperature at 123° C. for 1.5 hours, and increasing the temperature over 45-50 minutes to 165° C. and continuing to distill atmospherically. Next, the reaction mixture was under a gradually increasing vacuum over 3 hours to a full vacuum of at least 27 inches while maintaining a temperature of 163°-165° C., then heating the reaction mixture to 175° C. over 1 hour under full vacuum, followed by maintaining the vacuum and temperature at 175° C. for 15 minutes, and then steaming the reaction mixture (or water sparge) at 175° C. for 60 minutes, and after 60 minutes, cooling the resin to 164°-167° C. in about 15 minutes. Further, the process was concluded by removing the vacuum distillate (426.6 g) and discharging the product (212.9 g) from the reaction vessel.

Workup

  1. customto form a reaction mixture
  2. distillationThe reaction mixture was atmospherically distilled
  3. temperaturewhile heating to 123° C.
  4. temperaturemaintaining the 123° C. temperature for 2 hours
  5. customto 80° C
  6. addition37.2 g of 50.4% aqueous formaldehyde (40% of total charge) was added over 30 minutes to the reaction mixture
  7. distillationatmospherically distilling the reaction mixture to 123° C.
  8. temperaturemaintaining the temperature at 123° C. for 1.5 hours
  9. temperatureincreasing the temperature over 45-50 minutes to 165° C.
  10. distillationto distill atmospherically
  11. temperaturea gradually increasing vacuum over 3 hours to a full vacuum of at least 27 inches
  12. temperaturewhile maintaining a temperature of 163°-165° C.
  13. temperatureheating the reaction mixture to 175° C. over 1 hour under full vacuum
  14. temperatureby maintaining the vacuum and temperature at 175° C. for 15 minutes
  15. customthe reaction mixture (or water sparge) at 175° C. for 60 minutes
  16. temperaturecooling the resin to 164°-167° C. in about 15 minutes
  17. customby removing the vacuum distillate (426.6 g)

Sources & evidence

ORD record
ord-4e0793ac026045c08c0856b0f36a3f22
Source dataset
uspto-grants-2016_02
Patent number
US09249251B2

Reaction notes

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