(3-Chloropropyl)triethoxysilane → Octanethioic acid, S-(3-(triethoxysilyl)propyl) ester

HRID 1678545Notes

Reaction equation

HRID 1678545 reaction equation
[C:1]([O-:10])(=[S:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Na+].Cl[CH2:13][CH2:14][CH2:15][Si:16]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19]>[Cl-].C[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC>[C:1]([S:9][CH2:13][CH2:14][CH2:15][Si:16]([O:17][CH2:18][CH3:19])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 78771(3-Chloropropyl)triethoxysilaneHCID 24940094Sodium thiooctanoate

Product 1

HCID 12135713Octanethioic acid, S-(3-(triethoxysilyl)propyl) ester

Reagents, catalysts & solvents 1

HCID 21218Trioctylmethylammonium chlorideCatalyst

Conditions

Temperature
50 °C

Procedure

The aqueous solution of sodium thiooctanoate was heated to 50° C. and stirred with a mechanical stirrer throughout this procedure. To this solution was added 3-chloro-1-propyltriethoxysilane (444 grams, 1.84 moles) all at once. Immediately thereafter was added 0.15 grams of a concentrated aqueous solution of methyltrioctylammonium chloride. A temperature of 50° C. was maintained for 9 hours, with continued stirring, whereupon the temperature was raised to and subsequently maintained at 74° C. for an additional 15 hours, with continuous stirring. At this point, the solution was allowed to cool to ambient temperature, the stirring was stopped, and the organic phase separated from the aqueous phase by decantation in a separatory funnel. Gas chromatography and mass spectrometry (GC and GCMS) revealed a product containing 80% 3-octanoylthio-1-propyltriethoxysilane and 15.5% residual 3-chloro-1-propyltriethoxysilane (reported purities are based on area percent GC responses). The product was vacuum stripped at 110° C. at 0.1 torr to remove volatiles, primarily 3-chloro-1-propyltriethoxysilane, to yield a product of 94% purity. Product identity using this process confirmed by nuclear magnetic resonance spectroscopy (NMR).

Workup

  1. temperaturewas raised to and
  2. temperaturesubsequently maintained at 74° C. for an additional 15 hours, with continuous stirring
  3. temperatureto cool to ambient temperature
  4. customthe organic phase separated from the aqueous phase by decantation in a separatory funnel
  5. additioncontaining 80% 3-octanoylthio-1-propyltriethoxysilane and 15.5% residual 3-chloro-1-propyltriethoxysilane (reported purities are based on area percent GC responses)
  6. customstripped at 110° C. at 0.1 torr
  7. customto remove volatiles, primarily 3-chloro-1-propyltriethoxysilane
  8. customto yield a product of 94% purity

Sources & evidence

ORD record
ord-fe5ea9ae261d49358805bb42ab20ca46
Source dataset
uspto-grants-2011_08
Patent number
US08008524B2

Reaction notes

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