Formaldehyde → Formaldehyde--4-(2,4,4-trimethylpentan-2-yl)phenol (1/1)

HRID 435144Notes

Reaction equation

HRID 435144 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:3])[CH3:2].C=O.O.O.C(O)(=O)[C:21](O)=[O:22].C1(O)C=CC=CC=1>>[C:1]([C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:2])[CH3:3].[CH2:21]=[O:22]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 996PhenolHCID 88144-Tert-octylphenolHCID 61373Oxalic acid dihydrate

Product 1

HCID 168587Formaldehyde--4-(2,4,4-trimethylpentan-2-yl)phenol (1/1)

Conditions

Temperature
100 °C

Procedure

In a glass reaction vessel, 206 g (1 mole) of p-tert-octylphenol, 59.0 g (1.57 moles) of 80% paraformaldehyde and 4.5 g of oxalic acid dihydrate were reacted for 12 hours under water reflux (100° C.) to form a reaction intermediate. After performing the reaction for 12 hours, 87% of the formaldehyde used was consumed. The mole ratio of formaldehyde to p-tert-octylphenol (Fa/POP) was 1.37:1. Phenol (70.5 g; 0.75 mole) was added to the reaction intermediate and reacted at 100° C. for 2 hours. The reaction mixture was dehydrated at atmospheric pressure and then at reduced pressure by heating it to a temperature of 165° C. to give a pale yellow transparent p-tert-octylphenol/formaldehyde co-condensate (softening point 98° C.).

Workup

  1. customwere reacted for 12 hours under water
  2. customto form a reaction intermediate
  3. customthe reaction for 12 hours
  4. custom87% of the formaldehyde used was consumed
  5. customreacted at 100° C. for 2 hours
  6. temperatureat reduced pressure by heating it to a temperature of 165° C.

Sources & evidence

ORD record
ord-31e01792f1e34b6ea7b74b71d1ab33d8
Source dataset
uspto-grants-1983_08
Patent number
US04400492

Reaction notes

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