Trimethoxysilane → Butanedioic acid, bis[3-(trimethoxysilyl)propyl] ester

HRID 1279157

Reaction equation

HRID 1279157 reaction equation
[CH2:1]([O:4][C:5](=[O:14])[CH2:6][CH2:7][C:8]([O:10][CH2:11][CH:12]=[CH2:13])=[O:9])[CH:2]=[CH2:3].[CH3:15][O:16][SiH:17]([O:20][CH3:21])[O:18][CH3:19]>[Pt]>[CH3:15][O:16][Si:17]([CH2:3][CH2:2][CH2:1][O:4][C:5](=[O:14])[CH2:6][CH2:7][C:8]([O:10][CH2:11][CH2:12][CH2:13][Si:17]([O:20][CH3:21])([O:18][CH3:19])[O:16][CH3:15])=[O:9])([O:20][CH3:21])[O:18][CH3:19]

Participants

4

Reactant 2

HCID 17215Trimethoxysilane2×HCID 70215Butanedioic acid, 1,4-di-2-propen-1-yl ester

Product 1

HCID 54336550Butanedioic acid, bis[3-(trimethoxysilyl)propyl] esterYield 84%

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

A 250 milliliter round-bottom flask was equipped with a reflux condenser, a stir bar, a nitrogen inlet, and charged with 100 grams diallylsuccinate (0.504 moles) and 30 parts per million Platinum (64.1 microliters (μl) of a 5% Karstedt's solution). The mixture was heated and stirred at 70° C. for 5 minutes after which time trimethoxysilane was slowly added (145 milliliters; 135 grams; 1.11 mol). The mixture was allowed to react for 24 hours after which time the excess trimethoxysilane was stripped in vacuo. A yield of 184 grams of bis(trimethoxysilylpropyl)succinate (84% yield) was obtained. The purity and identity of the product were determined by proton nuclear magnetic resonance spectroscopy (4.1 ppm 4H triplet, 3.5 ppm 18H singlet, 2.6 ppm 4H singlet, 1.8 ppm 4H multiplet, 0.6 ppm 4H triplet).

Workup

  1. customA 250 milliliter round-bottom flask was equipped with a reflux condenser, a stir bar, a nitrogen inlet
  2. temperatureThe mixture was heated
  3. additionwas slowly added (145 milliliters; 135 grams; 1.11 mol)

Sources & evidence

ORD record
ord-b85305fde12f487ea608cd9132122044
Source dataset
uspto-grants-2002_09
Patent number
US06447922B1

Linked notes

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