Ethylenediamine → (Anilinomethyl)triethoxysilane

HRID 1879428Notes

Reaction equation

HRID 1879428 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>>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[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

5

Reactant 3

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

Product 2

HCID 6115AnilineHCID 11219420(Anilinomethyl)triethoxysilaneYield 62.9%

Conditions

Temperature
70 °C

Procedure

In a 500 ml four-necked flask having a reflux condenser, KPG stirrer and thermometer, 65.7 g of dry aniline (pKb 9.4) were heated to 120° C. and 60 g of chloromethyltriethoxysilane 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 42.4 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 during this procedure and the heavier ethylenediamine hydrochloride phase then being separated off. The upper phase was subjected to fractional distillation without a distillation column. 18.3 g of aniline having a purity of 84.8%, 14.4 g of aniline having a purity of 97.8% (45% recovery) and 47.8 g (yield 62.9%) of N-phenylaminomethyltriethoxysilane were obtained, the purity of which was determined as 88.9%. The chloride value of the product was 88 ppm.

Workup

  1. customIn a 500 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. distillationThe upper phase was subjected to fractional distillation without a distillation column

Sources & evidence

ORD record
ord-bd3ba0a8430c4919b59039924e6bc373
Source dataset
uspto-grants-2012_11
Patent number
US08314263B2

Reaction notes

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