Triethoxysilane → HCID 66611479, compound

HRID 2406912Notes

Reaction equation

HRID 2406912 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][CH:6]([CH:9]=[CH2:10])[CH2:5][CH:4]1[CH:11]=[CH2:12])=[CH2:2].[CH2:13]([O:15][SiH:16]([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])[CH3:14]>[Pt]>[CH2:13]([O:15][Si:16]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])[CH2:2][CH2:1][CH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][Si:16]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])[O:15][CH2:13][CH3:14])[CH2:5][CH:4]1[CH:11]=[CH2:12])[CH3:14]

Participants

4

Reactant 2

HCID 13830TriethoxysilaneHCID 96529Cyclohexane, 1,2,4-triethenyl-

Product 1

HCID 66611479HCID 66611479, compound

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Conditions

Temperature
110 °C

Procedure

Into a 5 liter round-bottom flask, equipped with an addition funnel, thermocouple, condenser and a magnetic stir were charged 1,2,4-trivinylcyclohexane (1390 g rams, 8.6 moles) and platinum catalyst (25 ppm of platinum (0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex in xylenes from Aldrich). The mixture was heated to 110° C. and triethoxysilane (1132 grams, 6.9 mole, from Momentive Performance Materials, Inc.) was added drop wise while sparging dry air through the flask. The reaction was exothermic during the addition. The reaction temperature was maintained at approximately 110° C. using a stream of cool air along the side of the flask. After the addition, the reaction was stirred an additional few hours at 110° C. The reaction was monitored using gas chromatography. The products were vacuum distilled at a pressure below 1 torr, to separate out dihydrosilation product, 1,4-bis-[2-(triethoxy-silanyl)-ethyl]-2-vinyl-cyclohexane and its stereoisomers from unreacted trivinylcyclohexane and monohydrosilation product.

Workup

  1. customInto a 5 liter round-bottom flask, equipped with an addition funnel
  2. customwhile sparging
  3. customdry air through the flask
  4. additionThe reaction was exothermic during the addition
  5. temperatureThe reaction temperature was maintained at approximately 110° C.
  6. additionAfter the addition
  7. stirringthe reaction was stirred an additional few hours at 110° C
  8. distillationdistilled at a pressure below 1 torr
  9. customto separate out dihydrosilation product, 1,4-bis-[2-(triethoxy-silanyl)-ethyl]-2-vinyl-cyclohexane and its stereoisomers from unreacted trivinylcyclohexane and monohydrosilation product

Sources & evidence

ORD record
ord-3418a94dd8044242a5a373b1eee2ddac
Source dataset
uspto-grants-2014_08
Patent number
US08809479B2

Reaction notes

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