Formaldehyde → 2,4'-Dihydroxydiphenylmethane

HRID 2298524

Reaction equation

HRID 2298524 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]=[O:9]>O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.P.[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W]>[CH:1]1[CH:2]=[C:3]([CH2:4][C:4]2[CH:5]=[CH:6][C:1]([OH:7])=[CH:2][CH:3]=2)[C:8]([OH:9])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 712Formaldehyde2×HCID 996Phenol2×

Product 1

HCID 755762,4'-DihydroxydiphenylmethaneYield 38.4%

Reagents, catalysts & solvents 1

HCID 45231312-Wolframophosphoric acidCatalyst

Procedure

Several methods are known in the art for the production of dihydroxydiphenylmethanes. Japanese Patent Jpn. Kokai Tokkyo Koho JP 0687775 (CA 121:57131) discloses a method for the condensation of phenol with aqueous formaldehyde using phosphotungstic acid which consists of 10:43:47 ratio of 2,2′-, 2,4′- and 4,4′-dihydroxydiphenylmethane isomers. EP 331, 172: CA 112:7160 discloses a method for reacting phenol with formaldehyde in the presence of an activated clay at 80° C. for 2 hours to give 38.8% of 4,4′-, 15.8% of 2,2′-, and 38.4% of 2,4′-dihydroxydiphenylmethane and 7.0% oligomer JP 63, 238, 632: CA 116: 75045 discloses a method for reacting phenol with formaldehyde in the presence of activated clay catalyst to give 2,2′-, 2,4′-, and 4,4′dihydroxydiphenylmethane in the ratio of 17.1: 41.4:44.5.

Workup

  1. customat 80° C.
  2. customfor 2 hours

Sources & evidence

ORD record
ord-84b29e42e9534bfa8ab81dd929ea9101
Source dataset
uspto-grants-2002_12
Patent number
US06492566B1

Linked notes

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