Formaldehyde → Dimethylol octylphenol

HRID 614704Notes

Reaction equation

HRID 614704 reaction equation
[OH-].[Li+].[CH2:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C=O.CC1C=C[C:24]([OH:27])=C(CCCCCCCC)C=1C.N1CC[O:40][CH2:39]C1>C1(C)C=CC=CC=1.C1C=CC=CC=1>[CH2:39]([CH:10]([CH2:24][OH:27])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17])[OH:40]

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 3939Lithium HydroxideHCID 8083MorpholineHCID 13700n-OctylphenolHCID 542146193,4-Dimethyl-2-octylphenol

Product 1

HCID 70608275Dimethylol octylphenol

Reagents, catalysts & solvents 1

HCID 160055Benzene, mixed with toluene, dealkylation productSolvent

Procedure

Dimethylol octylphenol was prepared by the base (lithium hydroxide 93% and TEA 4%) catalyzed condensation of octylphenol (1 mole) with 50% aqueous formaldehyde (2 moles). The dimethyloctylphenol product was dissolved in toluene/benzene at 65% solids. Morpholine was added in one charge, and the reaction mass was refluxed to completion and vacumn dehydrated to the desired softening point and methylol content of less than 1%. This value for methylol content includes methylol groups and benzylic ether bridges.

Workup

  1. additioncharge
  2. temperaturethe reaction mass was refluxed to completion and vacumn

Sources & evidence

ORD record
ord-17f20d858f4e4d2b8d29f67b7cb376ed
Source dataset
uspto-grants-1979_03
Patent number
US04146512

Reaction notes

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