Benzoic Acid → HCID 21285052, compound

HRID 1772565Notes

Reaction equation

HRID 1772565 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 6 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 64.1 g of 50.3% aqueous formaldehyde (60% of total charge) was added over 26 minutes. The reaction mixture was atmospherically distilled to 123° C., maintained at 123° C. for 2 hours, and then reduced to 80° C. 42.5 g of 50.3% aqueous formaldehyde (40% of total charge) was added over about 17 minutes to the reaction mixture, and then atmospherically distilled to 123° C., and then maintaining the temperature at 123° C. for 1.4 hours followed by 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., followed by heating the reaction mixture to 175° C. under full vacuum. Further, the process is concluded by removing the vacuum distillate (413.7 g) and discharging the product (261.2 g) from the reaction vessel.

Workup

  1. customto form a reaction mixture
  2. distillationThe reaction mixture was atmospherically distilled to 123° C.
  3. temperaturemaintained at 123° C. for 2 hours
  4. customreduced to 80° C
  5. addition42.5 g of 50.3% aqueous formaldehyde (40% of total charge) was added over about 17 minutes to the reaction mixture
  6. distillationatmospherically distilled to 123° C.
  7. temperaturemaintaining the temperature at 123° C. for 1.4 hours
  8. temperatureby increasing 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. temperatureby heating the reaction mixture to 175° C. under full vacuum
  13. customby removing the vacuum distillate (413.7 g)

Sources & evidence

ORD record
ord-02b05f771a30490090a94400c444fb50
Source dataset
uspto-grants-2016_02
Patent number
US09249251B2

Reaction notes

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