Cetyl Alcohol → (C16H33O)3Si-C3H6-SH

HRID 30510

Reaction equation

HRID 30510 reaction equation
[SH:1][CH2:2][CH2:3][CH2:4][Si:5]([O:12][CH2:13][CH3:14])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8].C(O)C[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CCCCO.CCCCO.CCCCO.CCCCO.[Ti].C(O)C>[Si:5]([CH2:4][CH2:3][CH2:2][SH:1])([O:12][CH2:13][CH2:14][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])([O:6][CH2:7][CH2:8][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])[O:9][CH2:10][CH2:11][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17]

Participants

5

Reactant 2

HCID 2682Cetyl AlcoholHCID 846581-Propanethiol, 3-(triethoxysilyl)-

Product 1

HCID 22227203(C16H33O)3Si-C3H6-SH

Reagents, catalysts & solvents 2

HCID 521701TetrabutoxytitaniumCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
105 °C

Procedure

2002.6 g of 3-mercaptopropyl(triethoxy)silane are mixed with 6108.5 g of hexadecanol as well as with 2 g of tetrabutyl orthotitanate and heated at 95-115° C. for 360 minutes in a 10 liter flask in a distillation apparatus. Ethanol formed in the transesterification is distilled off in vacuo at 15-600 mbar. After cooling, 7022 g of a colourless, solid product are obtained. As can be shown by 1H-NMR and 29Si-NMR, 92% of the EtO—Si groups are replaced by R—O—Si. In the transesterification more than 80 mole % of the ethanol-free compound [(C16H33O)3Si—C3H6—SH is formed, as can be shown for example by 1H-NMR and 29Si-NMR.

Workup

  1. distillationis distilled off in vacuo at 15-600 mbar
  2. temperatureAfter cooling
  3. custom7022 g of a colourless, solid product are obtained

Sources & evidence

ORD record
ord-3994d8fbc2414735b1726cfcc0b8241d
Source dataset
uspto-grants-2008_09
Patent number
US07423165B2

Linked notes

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