Ethylenediamine → (Trimethoxysilylpropyl)ethylenediamine

HRID 1757609Notes

Reaction equation

HRID 1757609 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].Cl[CH2:6][CH2:7][CH2:8][Si:9]([O:14][CH3:15])([O:12][CH3:13])[O:10][CH3:11].C(N)CN.ClCCC[Si](OC)(OC)OC>>[NH2:3][CH2:2][CH2:1][NH:4][CH2:6][CH2:7][CH2:8][Si:9]([O:14][CH3:15])([O:12][CH3:13])[O:10][CH3:11]

Participants

4

Reactant 3

HCID 3301Ethylenediamine2×HCID 624493-(Trimethoxysilyl)propyl chlorideHCID 86748947HCID 86748947, compound

Product 1

HCID 15659(Trimethoxysilylpropyl)ethylenediamineYield 81.7%

Procedure

A 300-ml, four necked glass flask equipped with a stirrer, reflux condenser, and thermometer was charged with 180.0 g (3.0 mol) of ethylene diamine and heated at 80° to 90° C. From a dropping funnel, 74.4 g (0.37 mol) of 3-chloropropyltrimethoxysilane was added dropwise to the flask over 1.25 hours (the molar ratio of ethylene diamine/3-chloropropyltrimethoxysilane=8.11). After one hour ripening, thereaction solution was heated until boiling whereupon 82.3 g (1.37 mol) of ethylene diamine was distilled out of the system through a reflux outlet port. The concentrated reaction solution was transferred to a separatory funnel and cooled for allowing the solution to separate into two layers. The lower layer of ethylene diamine hydrochloride was separated off. The upper layer containing 3-[N-(2-aminoethyl)]aminopropyltrimethoxysilane wastaken out and purified by simple distillation, obtaining 67.2 g of 3-[N-(2-aminoethyl)]aminopropyltrimethoxysilane. The yield was 81.7%.

Workup

  1. customA 300-ml, four necked glass flask equipped with a stirrer
  2. temperaturereflux condenser
  3. temperatureheated at 80° to 90° C
  4. temperaturesolution was heated
  5. distillationwas distilled out of the system through a reflux outlet port
  6. customThe concentrated reaction solution
  7. customwas transferred to a separatory funnel
  8. temperaturecooled
  9. customto separate into two layers
  10. customThe lower layer of ethylene diamine hydrochloride was separated off
  11. additionThe upper layer containing 3-[N-(2-aminoethyl)]aminopropyltrimethoxysilane
  12. distillationpurified by simple distillation

Sources & evidence

ORD record
ord-b686b8d1e8de4920a19c718987d7ee88
Source dataset
uspto-grants-1995_08
Patent number
US05446181

Reaction notes

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