Allyl glycidyl ether → 2,4,6,8-Tetramethyl-2,4,6,8-tetrakis(3-(oxiranylmethoxy)propyl)cyclotetrasiloxane

HRID 2073917Notes

Reaction equation

HRID 2073917 reaction equation
[CH2:1]([O:5][CH2:6][CH:7]=[CH2:8])[CH:2]1[O:4][CH2:3]1.[CH3:9][SiH:10]1[O:17][SiH:16]([CH3:18])[O:15][SiH:14]([CH3:19])[O:13][SiH:12]([CH3:20])[O:11]1>COCCOCCOC.[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>[O:4]1[CH2:3][CH:2]1[CH2:1][O:5][CH2:6][CH2:7][CH2:8][Si:16]1([CH3:18])[O:17][Si:10]([CH2:8][CH2:7][CH2:6][O:5][CH2:1][CH:2]2[O:4][CH2:3]2)([CH3:9])[O:11][Si:12]([CH2:8][CH2:7][CH2:6][O:5][CH2:1][CH:2]2[O:4][CH2:3]2)([CH3:20])[O:13][Si:14]([CH2:8][CH2:7][CH2:6][O:5][CH2:1][CH:2]2[O:4][CH2:3]2)([CH3:19])[O:15]1

Participants

5

Reactant 2

HCID 7838Allyl glycidyl ether2×HCID 754041,3,5,7-Tetramethylcyclotetrasiloxane3×

Product 1

HCID 1084902,4,6,8-Tetramethyl-2,4,6,8-tetrakis(3-(oxiranylmethoxy)propyl)cyclotetrasiloxane

Reagents, catalysts & solvents 2

HCID 61859Chloroplatinic acidCatalystHCID 8150DiglymeSolvent

Conditions

Temperature
100 °C

Procedure

Allyl glycidyl ether (57.1 g, 0.5 moles) was added to a 250 mL 3-neck flask, equipped with a stirrer, dropping funnel, internal thermometer and condenser, and heated to 100° C. After the addition of 1 mL of a 1 weight percent solution of hexachloroplatinic acid in diethylene glycol dimethyl ether, 24.0 g (0.1 moles) of 2,4,6,8-tetramethylcyclotetrasiloxane were added very rapidly with vigorous stirring, the internal temperature rising to 195° C. After the addition of 2,4,6,8-tetramethylcyclotetrasiloxane, stirring was continued until the temperature of the reaction product had dropped to 130° C. Unreacted portions of the allyl glycidyl ether and 2,4,6,8-tetramethylcyclotetrasiloxane were removed by stirring the reaction mixture at 60°-70° C. at a vacuum of 0.1 hPa, produced by an oil pump. The slightly yellowish crude product (77.8%), nD20 : 1.4633, was subjected to a fractional vacuum distillation using a packed column. The compound (21) distilled at about 335° C. and 1 hPa as a clear, viscous liquid, the greater portion polymerizing. nD20 : 1,4668.

Workup

  1. customequipped with a stirrer
  2. additionwere added very rapidly with vigorous stirring
  3. customrising to 195° C
  4. additionhad dropped to 130° C
  5. customwere removed
  6. stirringby stirring the reaction mixture at 60°-70° C. at a vacuum of 0.1 hPa
  7. customproduced by an oil pump
  8. distillationThe slightly yellowish crude product (77.8%), nD20 : 1.4633, was subjected to a fractional vacuum distillation
  9. distillationThe compound (21) distilled at about 335° C.
  10. custom1 hPa as a clear, viscous liquid, the greater portion polymerizing

Sources & evidence

ORD record
ord-f77591b27fc74304823c898611faa5a7
Source dataset
uspto-grants-1990_04
Patent number
US04920184

Reaction notes

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