Formaldehyde → HCID 178442629, compound

HRID 2053068Notes

Reaction equation

HRID 2053068 reaction equation
[CH3:1][C:2]([C:9]1[CH:14]=[C:13]([C:15]2[C:23]3[N:22]=[N:21][NH:20][C:19]=3[CH:18]=[CH:17][CH:16]=2)[C:12](O)=[CH:11][CH:10]=1)([CH3:8])[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5].[CH2:25]=[O:26].C([NH:29][CH2:30][CH3:31])C.[CH3:32][O-:33].[Na+]>CO.C1(C)C(C)=CC=CC=1>[CH2:12]([C:13]1[CH:14]=[C:9]([C:2]([CH3:1])([CH3:8])[CH2:3][C:4]([CH3:7])([CH3:5])[CH3:6])[CH:10]=[C:11]([C:31]2[C:30]3[N:29]=[N:21][NH:20][C:19]=3[CH:18]=[CH:17][CH:16]=2)[C:32]=1[OH:33])[C:11]1[CH:10]=[C:9]([C:2]([CH3:8])([CH3:1])[CH2:3][C:4]([CH3:7])([CH3:5])[CH3:6])[CH:14]=[C:13]([C:15]2[C:23]3[N:22]=[N:21][NH:20][C:19]=3[CH:18]=[CH:17][CH:16]=2)[C:25]=1[OH:26]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 8021DiethylamineHCID 10942334Sodium MethoxideHCID 178442657HCID 178442657, compound

Product 1

HCID 178442629HCID 178442629, compoundYield 150.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
10 °C

Procedure

To a container with a stirrer, 63.4 kg of 4-(1,1,3,3-tetramethylbutyl)-6-benzotriazolyl phenol, 5.2 kg of paraformaldehyde, 11.0 kg of diethylamine and 60 L of xylene were charged, and reacted at a temperature of 95 to 100° C. for 24 hours. Then, 3.1 kg of 28% sodium methylate solution in methanol was added and reacted under nitrogen gas at temperature of 145 to 150° C. for 10 hours. The reaction solution was washed with water, and crystallized by cooling the xylene layer to 10° C. The resulting crystal was filtered to obtain 56.8 kg (yield 88%) of 2,2′-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-benzotriazolylphenol] as white solid in a shape of fine powder (causing dust). Powder X-ray diffraction analysis for the resulting crystal with Cu-Kα radiation indicated that it was type I having distinct diffraction peaks at diffraction angles (2θ±0.1°) of 7.1°, 8.6°, 14.3°, 16.1°, 18.1° and 23.0° as shown in FIG. 4. Further, DSC analysis indicated that the crystal was 100% type I as shown in FIG. 5.

Workup

  1. customreacted at a temperature of 95 to 100° C. for 24 hours
  2. customreacted under nitrogen gas at temperature of 145 to 150° C. for 10 hours
  3. washThe reaction solution was washed with water
  4. customcrystallized
  5. filtrationThe resulting crystal was filtered

Sources & evidence

ORD record
ord-989c4471d83e402f90897f4e832dd4b5
Source dataset
uspto-grants-2008_02
Patent number
US07326744B2

Reaction notes

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