M-Cresol → Tar acids, methylphenol fraction

HRID 2306527Notes

Reaction equation

HRID 2306527 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8].[CH:9]1[C:14]([OH:15])=[CH:13][CH:12]=[C:11]([CH3:16])[CH:10]=1.O.O.C(O)(=O)C(O)=O.C=O>C(C(C)=O)C(C)C.C(OC(C)COC)(=O)C.CCCCCCC.C(O)(=O)C>[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8].[CH:13]1[C:14]([OH:15])=[CH:9][CH:10]=[C:11]([CH3:16])[CH:12]=1

Participants

9

Reactant 4

HCID 342M-CresolHCID 712FormaldehydeHCID 2879P-CresolHCID 61373Oxalic acid dihydrate

Product 1

HCID 21829806Tar acids, methylphenol fraction

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 7909Methyl Isobutyl KetoneSolvent3×HCID 7946Propylene glycol methyl ether acetateSolventHCID 8900HeptaneSolvent

Conditions

Temperature
80 °C

Procedure

Into a 1 L four-necked flask equipped with a reflux tube, stirring apparatus and thermometer were charged 87.3 g of m-cresol, 131.0 g of p-cresol, 6.1 g of oxalic acid dihydrate, 59.3 g of 90% acetic acid and 203 g of methyl isobutyl ketone and the mixture was heated up to 80° C. Into this was dropped 94.2 g of a 37% formaldehyde aqueous solution over 1 hour. Thereafter, the mixture was heated up to reflux temperature and kept at the same temperature for 12 hours. The resulted reaction solution was diluted with methyl isobutyl ketone, and washed with water and dehydrated, to obtain a 38.0% methyl isobutyl ketone solution of a novolak resin. 384 g of this resin solution was charged into a 5 L bottom-discharging type flask, diluted with 574 g of methyl isobutyl ketone, and 764 g of n-heptane was charged and the mixture was stirred at 60° C. and allowed to stand still, then, separated to obtain a novolak resin solution in the lower layer. This novolak resin solution was diluted with propylene glycol methyl ether acetate and then concentrated, to obtain a propylene glycol methyl ether acetate solution of a novolak resin. This resin is called resin A6.

Workup

  1. customInto a 1 L four-necked flask equipped with a reflux tube
  2. temperatureThereafter, the mixture was heated up
  3. temperatureto reflux temperature
  4. customThe resulted reaction solution
  5. washwashed with water
  6. customto obtain a 38.0% methyl isobutyl ketone solution of a novolak resin
  7. additionwas charged
  8. stirringthe mixture was stirred at 60° C.
  9. customseparated
  10. customto obtain a novolak resin solution in the lower layer
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-720a446acbf64bfda60c9983225380eb
Source dataset
uspto-grants-2004_12
Patent number
US06828079B2

Reaction notes

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