Formaldehyde → HCID 69677329, compound

HRID 1836937Notes

Reaction equation

HRID 1836937 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:9].[CH3:17][NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C=O>C(O)=O>[CH2:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:9].[CH3:17][NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH2:1]=[O:7].[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 996Phenol4×HCID 7515N-MethylanilineHCID 7670N-Ethylaniline

Product 1

HCID 69677329HCID 69677329, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A one liter flask was charged with 376.4 g of phenol (4.0 moles), 96.8 g N-ethylaniline (0.8 mole), 85.6 g N-methylaniline (0.8 mole) and 7.0 g. 90% formic acid. The reaction mixture was heated to 70° C. and then 191.0 g. of 50% formalin (3.2 moles) was added over 60 minutes at 70-72° C. After 2 hours at 70° C. the percent free phenol determined gas chromatographically was 31.5% (vs. 57.3% for no reaction of phenol). The temperature was raised to 100° C. and maintained at 100° C. for one hour at which time the percent phenol was determined to be 30.6%. Reaction mixture was then atmospherically distilled to 160° C. to collect 165 g. distillate. Phenol (165 g.) was then recovered by vacuum distillation increasing temperature to 190° C. while increasing vacuum to 30″ inches of mercury. When phenol appeared to stop distilling over, vacuum was broken and 67 ml. of deionized water added over 50 minutes at about 190° C. Vacuum was then applied to remove water at 190° C. under 30 inches of mercury vacuum. Product yield was 406.3 g and was characterized by phenol, 0.65%; nitrogen, 5.53%; Mw/Mn, 1190/327; viscosity, 426 cps (175° C.) and in Table 5.

Workup

  1. temperatureThe temperature was raised to 100° C.
  2. customReaction mixture
  3. distillationwas then atmospherically distilled to 160° C.
  4. customto collect 165 g
  5. distillationPhenol (165 g.) was then recovered by vacuum distillation
  6. temperatureincreasing temperature to 190° C.
  7. temperaturewhile increasing vacuum to 30″ inches of mercury
  8. distillationto stop distilling over, vacuum
  9. additionof deionized water added over 50 minutes at about 190° C
  10. customto remove water at 190° C. under 30 inches of mercury vacuum
  11. customviscosity, 426 cps (175° C.)

Sources & evidence

ORD record
ord-7f4e39174b7443b89e268f2b9cf5ed99
Source dataset
uspto-grants-2004_08
Patent number
US06780511B2

Reaction notes

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