Toluene → 1-(2-Methylpropyl)-1,1,3,3-tetramethyldisiloxane

HRID 1786658Notes

Reaction equation

HRID 1786658 reaction equation
[CH3:1][SiH2:2][O:3][Si:4]([CH3:7])([CH3:6])[CH3:5].[CH3:8][C:9](=C)[CH3:10].[C:12]1(C)C=CC=CC=1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[CH3:8][CH:9]([CH3:10])[CH2:5][Si:4]([CH3:7])([CH3:6])[O:3][SiH:2]([CH3:12])[CH3:1]

Participants

5

Reactant 3

HCID 1140TolueneHCID 8255IsobutyleneHCID 57376941Tetramethyl disiloxane2×

Product 1

HCID 1233947171-(2-Methylpropyl)-1,1,3,3-tetramethyldisiloxane

Reagents, catalysts & solvents 1

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)Catalyst

Conditions

Temperature
65 °C

Procedure

An 80 mL Fischer-Porter high pressure bottle was charged with tetramethyldisiloxane (10.0 g), toluene (10.0 g) and Wilkinson's catalyst ((PPh3)3RhCl, 40 ppm), stirred and brought to 60° C. The bottle was attached to a manifold and pressurized with isobutylene (25 psig) and maintained at 60-70° C. for 8 h. The pressure was vented, and the reaction was sampled for GC analysis; found residual tetramethyldisiloxane, M′MR product and MRMR byproduct (2:95:3). The resulting material was stripped under vacuum (approx. 150 mm Hg) at 40° C. to remove olefin and M′M′, then filtered with Celite to yield 21.3 g M′MR product/toluene solution, 94% GC purity. This product was found to have an Si—H content of 11 cc H2/g by gasiometric titration.

Workup

  1. custombrought to 60° C
  2. aliquotthe reaction was sampled for GC analysis
  3. customwas stripped under vacuum (approx. 150 mm Hg) at 40° C.
  4. customto remove olefin and M′M′,
  5. filtrationthen filtered with Celite
  6. customto yield 21.3 g M′MR product/toluene solution, 94% GC purity

Sources & evidence

ORD record
ord-bb51094371c24b66b89e385748086d88
Source dataset
uspto-grants-2009_03
Patent number
US07507775B2

Reaction notes

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