Formaldehyde → HCID 69677328, compound

HRID 1836936Notes

Reaction equation

HRID 1836936 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[CH2:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:11]>C(O)=O>[CH2:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:11].[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 996Phenol3×HCID 7670N-Ethylaniline2×

Product 1

HCID 69677328HCID 69677328, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A one liter flask was charged with 376.4 g phenol (4.0 moles) and 95.4 g 50.3% formalin (1.6 moles). The reaction mixture was heated to 50° C. and then 96.8 g N-ethylaniline (0.8 mole) added over 35 minutes at 50-52° C. After 30 minutes at 50° C. the percent free phenol was 41.4% (vs. 66.2% if no phenol reacted). 95.4 g 50.3% formalin (0.6 mole) was then added. Then 96.8 g N-ethylaniline (0.8 mole) was added over ½ hour at 50° C. This temperature was maintained for 73 minutes, whereupon 7.0 g 90% formic acid was added. After 15 minutes the temperature was raised to 100° C. and maintained at 100° C. for 1 hour. Atmospheric distillate (163 g) phenol (149 g) and product (443. g) were recovered as described in Example 23 above. Product is characterized in Table 3B and Table 5.

Workup

  1. additionwas added
  2. temperatureAfter 15 minutes the temperature was raised to 100° C.
  3. temperaturemaintained at 100° C. for 1 hour
  4. distillationAtmospheric distillate (163 g) phenol (149 g) and product (443. g) were recovered

Sources & evidence

ORD record
ord-9b545a54064f4c59908b9109948e73b7
Source dataset
uspto-grants-2004_08
Patent number
US06780511B2

Reaction notes

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