Ethylenediamine → N,N'-Bis(3-(trimethoxysilyl)propyl)ethane-1,2-diamine
Reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH2:7][Si:8]([O:13][CH3:14])([O:11][CH3:12])[O:9][CH3:10].Cl[CH2:16][CH2:17][CH2:18][Si:19]([O:24][CH3:25])([O:22][CH3:23])[O:20][CH3:21].C(N)CN>>[Si:8]([CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2][NH:1][CH2:16][CH2:17][CH2:18][Si:19]([O:24][CH3:25])([O:22][CH3:23])[O:20][CH3:21])([O:13][CH3:14])([O:9][CH3:10])[O:11][CH3:12]Participants
Conditions
- Temperature
- 140 °C
Procedure
A 2 liter, 3-necked reaction flask equipped with a magnetic stirrer, electric heating mantle, dropping funnel and water condenser, containing 22.0 grams of NH2CH2CH2NH(CH2)3Si(OCH3)3 was heated to 140° C. whereupon the addition thereto of 198.0 grams of 3-chloropropyltrimethoxy silane (Cl(CH2)3Si(OCH3)3) was commenced. Cl(CH2)3Si(OCH3)3 was introduced dropwise to the reaction flask over a period of 1 hour while maintaining a temperature of 145° C. to 150° C. by the occasional application of a water bath. The resultant mixture was cooled to 75° C., and 90 grams of anhydrous ethylenediamine was added to the cooled mixture. Thereafter, the mixture was allowed to separate into layers with the upper product containing layer being separated therefrom and stripped by vacuum distillation of low boiling volatiles to yield 370 grams of (CH3O)3SiC3H6NHC2H4NHC3H6Si(OCH3)3. Amine titration and 13C NMR and 29Si NMR analysis verified the assigned structure of the resultant product.
Workup
- customA 2 liter, 3-necked reaction flask equipped with a magnetic stirrer
- temperaturewhile maintaining a temperature of 145° C. to 150° C. by the occasional application of a water bath
- customto separate into layers with the upper product
- additioncontaining layer
- custombeing separated
- distillationstripped by vacuum distillation of low boiling volatiles
Sources & evidence
- ORD record
- ord-2d10055733b14274873c0cf9a679f71b
- Source dataset
- uspto-grants-1991_05
- Patent number
- US05019340
Reaction notes
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