4-Aminophenol → Benzenamine, 4-[3-(trimethoxysilyl)propoxy]-

Temperatur

85 °C

A glass reactor was charged with 60 g (0.55 mole) p-aminophenol, 43.28 g of a 50% aqueous solution of sodium hydroxide (0.54 mole NaOH), 112 cc dimethylsulfoxide and 120 cc toluene. The resultant mixture was heated to the boiling point for six hours under a nitrogen atmosphere to remove all of the water present by azeotropic distillation. The reaction mixture was then allowed to cool to about 75° C., at which time 109 g (0.55 mole) of 3-chloropropyl trimethoxysilane was added dropwise while the reaction mixture was stirred. The temperature of the reaction mixture increased spontaneously to 85° C. during this addition. The temperature of the reaction mixture was maintained at from 75° to 85° C. by heating and control of the addition rate. Following completion of the addition, the reaction mixture was heated at 115° C. for 16 hours, following which the mixture was allowed to cool and was filtered to remove any solid material. The solvents were then removed under a pressure of about 15 mm of mercury at a temperature of about 60° C. The pressure was then reduced to from 3 to 4 mm of mercury and the material boiling from 170° to 180° C. was recovered. This fraction, which weighed 70 g, was distilled using a fractionating column and a 50 g portion boiling from 175° to 177° C. under a pressure of 3 mm of mercury, was collected. The colorless liquid was found to contain 10.19% silicon and 5.20% nitrogen. The calculated values for 3(p-aminophenoxy)propyl trimethoxy silane are 10.33% silicon and 5.17% nitrogen. The infrared and nuclear magnetic resonance spectra of the product were in agreement with the proposed structure.

1. customto remove all of the water present
2. distillationby azeotropic distillation
3. additionwas added dropwise while the reaction mixture
4. temperatureThe temperature of the reaction mixture was maintained at from 75° to 85° C.
5. temperatureby heating
6. additioncompletion of the addition
7. temperaturethe reaction mixture was heated at 115° C. for 16 hours
8. temperatureto cool
9. filtrationwas filtered
10. customto remove any solid material
11. customThe solvents were then removed under a pressure of about 15 mm of mercury at a temperature of about 60° C
12. customboiling from 170° to 180° C.
13. customwas recovered
14. distillationwas distilled
15. customboiling from 175° to 177° C. under a pressure of 3 mm of mercury
16. customwas collected

ORD-Eintrag

ord-4edddc1683ee4cfbaab3c791cd79be9e

Quelldatensatz

uspto-grants-1987_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04645844