Reaction #502053

Reaction equation

water

trifluoroacetic acid

hexamethylene tetramine

4,4′-methylene bis(2,5-dimethyl-6-hydroxymethylphenol)

→

yellow powder

Yield 96.7%

4,4′-methylene bis(2,5-dimethyl-6-formylphenol)

Yield 96.7%

Solvents

toluene

methyl isobutyl ketone

Conditions

Workup

1. 1
   Otherreaction
2. 2
   workup.ADDITIONAfter the entire amount of the material had been added
3. 3
   Otherobtained from the reaction
4. 4
   Otherhydrolysis reaction for 1 hour at a temperature of 70° C. (crystal
5. 5
   Otherprecipitated during this reaction)
6. 6
   workup.ADDITION245.7 g of 16% aqueous sodium hydroxide solution was added
7. 7
   workup.WAITwas then kept at a temperature of 80° C. for 1 hour
8. 8
   TemperatureThereafter, the mixture was cooled
9. 9
   Otherprecipitated crystal
10. 10
    Filtrationwas filtered out
11. 11
    Otherto obtain 72.3 g of coarse crystal
12. 12
    OtherNext, the obtained coarse crystal
13. 13
    workup.WAITthe mixture was kept at a temperature of 80° C. for 1 hour
14. 14
    Temperaturewas cooled
15. 15
    Otherprecipitated crystal
16. 16
    Filtrationwas filtered out
17. 17
    Otherdried

Procedure

171.0 g (1.5 mol) of trifluoroacetic acid was put in a four-way flask with a capacity of 1 liter and the reaction container was substituted by nitrogen, after which 47.3 g (0.34 mol) of hexamethylene tetramine was added at a temperature of approx. 25° C., and then 47.4 g (0.15 mol) of 4,4′-methylene bis(2,5-dimethyl-6-hydroxymethylphenol) was added under agitation over 2.5 hours at a temperature of 50° C. to cause reaction. After the entire amount of the material had been added, the temperature was raised to 80° C., and then the mixture was further agitated for 20 hours as a post-reaction. Next, 150.0 g of water was added to the mixture liquid obtained from the reaction to implement hydrolysis reaction for 1 hour at a temperature of 70° C. (crystal precipitated during this reaction). 245.7 g of 16% aqueous sodium hydroxide solution was added to neutralize the obtained mixture liquid, which was then kept at a temperature of 80° C. for 1 hour. Thereafter, the mixture was cooled and precipitated crystal was filtered out to obtain 72.3 g of coarse crystal. Next, the obtained coarse crystal was put in a four-way flask with a capacity of 1 liter, and then 70.0 g of methyl isobutyl ketone and 50.0 g of toluene were added and the mixture was kept at a temperature of 80° C. for 1 hour (the solution was in a slurry state), after which the mixture was cooled and precipitated crystal was filtered out and dried to obtain 45.3 g of yellow powder having a purity of 94.6% based on HPLC.

Source