Allyl glycidyl ether → Glycidoxypropyltrimethoxysilane

HRID 1605383Notes

Reaction equation

HRID 1605383 reaction equation
[CH2:1]([O:5][CH2:6][CH:7]=[CH2:8])[CH:2]1[O:4][CH2:3]1.[CH3:9][O:10][SiH:11]([O:14][CH3:15])[O:12][CH3:13]>CC(C)=O>[CH2:1]([O:5][CH2:6][CH2:7][CH2:8][Si:11]([O:14][CH3:15])([O:12][CH3:13])[O:10][CH3:9])[CH:2]1[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 7838Allyl glycidyl ether2×HCID 17215Trimethoxysilane

Product 1

HCID 17317GlycidoxypropyltrimethoxysilaneYield 91.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a 10-liter flask provided with stirrer, reflux condenser, internal thermometer and 2 dropping funnels, one filled with 2.85 kg of allyl glycidyl ether and the other with 3.05 kg of trimethoxysilane, 500 ml of allyl glycidyl ether or gamm-glycidyloxypropyltrimethoxysilane was heated to 130°C. Then 1 ml of an 0.01 molar solution of the mesityl oxide-platinum dichloride complex in acetone was added and the reaction was allowed to take place with rapid stirring and the simultaneous feeding in of the two reactants, within about 20 minutes. The internal temperature was kept between 130°C and 140°C by slight external cooling and by regulating the feed. This was followed by vacuum distillation producing 5.4 kg of γ-glycidyloxypropyltrimethoxysilane boiling at BP0.05 81°C (nD20 : 1.4290, d420 : 1.073).

Workup

  1. customIn a 10-liter flask provided with stirrer
  2. temperaturereflux condenser
  3. customwas kept between 130°C and 140°C
  4. temperatureexternal cooling
  5. distillationThis was followed by vacuum distillation

Sources & evidence

ORD record
ord-13fdda43a00c449c8d7ea7e109ba64df
Source dataset
uspto-grants-1976_04
Patent number
US03950364

Reaction notes

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