Triethoxysilane → HCID 86600359, compound

HRID 915549Notes

Reaction equation

HRID 915549 reaction equation
[CH2:1]([O:4][CH2:5][C:6]([CH2:15][O:16][CH2:17][CH:18]=[CH2:19])([CH2:13][CH3:14])[CH2:7][O:8][Si:9]([CH3:12])([CH3:11])[CH3:10])[CH:2]=[CH2:3].[CH2:20]([O:22][SiH:23]([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])[CH3:21]>>[CH2:20]([O:22][Si:23]([O:27][CH2:28][CH3:29])([O:24][CH2:25][CH3:26])[CH2:3][CH2:2][CH2:1][O:4][CH2:5][C:6]([CH2:15][O:16][CH2:17][CH2:18][CH2:19][Si:23]([O:27][CH2:28][CH3:29])([O:24][CH2:25][CH3:26])[O:22][CH2:20][CH3:21])([CH2:13][CH3:14])[CH2:7][O:8][Si:9]([CH3:12])([CH3:11])[CH3:10])[CH3:21]

Participants

3

Reactant 2

HCID 13830Triethoxysilane3×HCID 86204655HCID 86204655, compound

Product 1

HCID 86600359HCID 86600359, compound

Conditions

Temperature
80 °C

Procedure

A 1-liter, 3-neck flask equipped with magnetic stirrer, pot thermometer, addition funnel and condenser was charged with 143.2 g of 2,2-Bis(allyloxymethyl)-1-trimethylsiloxybutane. After heating to ˜80° C., 35 g of triethoxysilane was added followed by 1 ml of Karstedt catalyst containing 2% Pt. Once initiation was observed, the balance of triethoxysilane (133.4 g) was added at a rate to maintain temperature at 80-110° C. When the addition was complete, an additional 0.5 ml of Karstedt catalyst was added and temperature of 90° C. was maintained for 2 hours. A GC indicated the reaction was not complete. Two additional portions 43 g of triethoxysilane and 0.5 g of Karstedt were added, maintaining the temperature at 95-105° C. The product was purified by means of a wiped-film evaporator, removing volatiles on a first pass and then distilling crude product on a second pass. A short-path distillation produced purified product: b.p.: 200-205° C. at 0.8 mm; density: 0.980; 1HNMR(C6D6): 0.13(s, 9H), 0.77(m, 4H), 1.00(m, 3H), 1.14(t, 18H), 1.18(m, 2H), 1.85(m, 4H) 3.38(dd, 8H), 3.76(s, 2H), 3.81(q, 12H). The FTIR showed a strong absorption at 1105.1 cm−1, which is characteristic of Si—O.

Workup

  1. customA 1-liter, 3-neck flask equipped with magnetic stirrer
  2. additionpot thermometer, addition funnel and condenser
  3. temperatureto maintain temperature at 80-110° C
  4. additionWhen the addition
  5. temperaturetemperature of 90° C. was maintained for 2 hours
  6. temperaturemaintaining the temperature at 95-105° C
  7. customThe product was purified by means of a wiped-film evaporator
  8. customremoving volatiles on a first pass
  9. distillationdistilling crude product on a second pass
  10. distillationA short-path distillation
  11. customproduced
  12. custompurified product
  13. customa strong absorption at 1105.1 cm−1, which

Sources & evidence

ORD record
ord-f2b59a61e05541468357a025a5934877
Source dataset
uspto-grants-2007_09
Patent number
US07265236B2

Reaction notes

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