Benzoic Acid → HCID 21285052, compound

HRID 1772567Notes

Reaction equation

HRID 1772567 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 8 was initiated by charging 593.5 g phenol (6.31 moles), 1.2 g of benzoic acid (0.2% of phenol) and 75.2 g melamine (0.60 moles) into a reaction vessel to form a reaction mixture. The reaction mixture was heated to 80° C. and 68.7 g of 50.1% aqueous formaldehyde (60% of total charge) was added in over 30 minutes. The reaction mixture was atmospherically distilled to 123° C., and then maintaining the 123° C. temperature for 2 hours before reducing the reaction mixture temperature to 80° C. 45.8 g of 50.1% aqueous formaldehyde (40% of total charge) was added over about 15 minutes to the reaction mixture, followed by atmospherically distilling the reaction mixture to 123° C., maintaining the temperature at 123° C. for 1.5 hours, and then increasing the temperature over 50 minutes to 165° C. and continuing to distill atmospherically. Next, the reaction mixture was under a gradually increasing vacuum over 2 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 is concluded by removing the vacuum distillate (395.0 g) and discharging the product (279.2 g) from the reaction vessel.

Workup

  1. customto form a reaction mixture
  2. distillationThe reaction mixture was atmospherically distilled to 123° C.
  3. temperaturemaintaining the 123° C. temperature for 2 hours
  4. customto 80° C
  5. addition45.8 g of 50.1% aqueous formaldehyde (40% of total charge) was added over about 15 minutes to the reaction mixture
  6. distillationby atmospherically distilling the reaction mixture to 123° C.
  7. temperaturemaintaining the temperature at 123° C. for 1.5 hours
  8. temperatureincreasing the temperature over 50 minutes to 165° C.
  9. distillationto distill atmospherically
  10. temperaturea gradually increasing vacuum over 2 hours to full vacuum of at least 27 inches
  11. temperaturewhile maintaining a temperature of 163°-165° C.
  12. temperaturebefore heating the reaction mixture to 175° C. under full vacuum
  13. customby removing the vacuum distillate (395.0 g)

Sources & evidence

ORD record
ord-5ce0e935c6ef4a94b0cb3c7444c299b3
Source dataset
uspto-grants-2016_02
Patent number
US09249251B2

Reaction notes

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