Ethylenediamine → (Anilinomethyl)triethoxysilane

HRID 1879429Notes

Reaction equation

HRID 1879429 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:9][Si:10]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13].C(N)CN>>[C:2]1([NH:1][CH2:9][Si:10]([O:11][CH2:12][CH3:13])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 6115AnilineHCID 84858Silane, (chloromethyl)triethoxy-

Product 1

HCID 11219420(Anilinomethyl)triethoxysilaneYield 79%

Conditions

Temperature
70 °C

Procedure

In a 1000 ml four-necked flask having a reflux condenser, KPG stirrer and thermometer, 602 g of dry aniline (pKb 9.4) were heated to 120° C. and 200 g of (chloromethyl)triethoxysilane were added in the course of 180 min with stirring and stirring was effected for a further 60 min. Thereafter, the temperature was reduced to 105° C. and 109 g of ethylenediamine (pKb 4.07) were added to the mixture in the course of 10 min with stirring, phase separation occurring. At constant temperature, stirring was effected for a further 30 min, cooling to 70° C. being effected and the heavier ethylenediamine hydrochloride phase then being separated off. 27 g of anhydrous Lupasol G20 (BASF AG) are then added to the upper phase and distilled as described in Example 4. 200 g of N-phenylaminomethyltriethoxysilane (73.2% yield) having a purity of 94.9% are obtained. The chloride value was 8 ppm.

Workup

  1. customIn a 1000 ml four-necked flask having
  2. stirringstirring
  3. customwas reduced to 105° C.
  4. stirringwith stirring
  5. customphase separation
  6. stirringAt constant temperature, stirring
  7. waitwas effected for a further 30 min
  8. customthe heavier ethylenediamine hydrochloride phase then being separated off
  9. addition27 g of anhydrous Lupasol G20 (BASF AG) are then added to the upper phase
  10. distillationdistilled

Sources & evidence

ORD record
ord-055f47dff3e149df916ca77a5a74848c
Source dataset
uspto-grants-2012_11
Patent number
US08314263B2

Reaction notes

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