Ethylenediamine → Ethylenediamine

HRID 2420279Notes

Reaction equation

HRID 2420279 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[Cl:5][C:6]([Cl:12])([Cl:11])[CH2:7][CH:8]1[O:10][CH2:9]1.C1OC1C>C(O)(C)C.C(O)C>[CH2:1]([NH2:4])[CH2:2][NH2:3].[Cl:5][C:6]([Cl:12])([Cl:11])[CH2:7][CH:8]([OH:10])[CH3:9]

Participants

7

Reactant 3

HCID 3301EthylenediamineHCID 6378Propylene Oxide2×HCID 183221,1,1-Trichloro-3,4-epoxybutane

Product 2

HCID 3301EthylenediamineHCID 20554767HCID 20554767, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 10.0g (0.17 mole) ethylenediamine in 100 ml isopropanol and 50 ml ethanol heated at 60° C. under nitrogen was added, dropwise, a mixture of 58.5g (0.33 mole) 4,4,4-trichloro-1,2-epoxybutane and 58.5g (1.0 mole) propylene oxide over a period of one hour. The reaction mixture was refluxed at 70° C. for one hour and an additional 17.2g (0.30 mole) of propylene oxide was then added dropwise. Refluxing with agitation was continued for an additional five hours and the mixture allowed to stand overnight. Evaporation of the solvent via vacuum afforded 74g of an addition product between ethylenediamine, 2-hydroxypropane, and 4,4,4-trichloro-2-hydroxybutane; hydroxyl number = 518. Analysis: (Calculated) %Cl, 29.52; %N, 6.47. (Found) %Cl, 29.22; %N, 6.31. On the basis of the analytical data one mole of ethylenediamine reacted with 1.2 moles 4,4,4-trichloro-1,2-epoxybutane and 2.8 moles propylene oxide.

Workup

  1. additionwas added
  2. temperatureRefluxing with agitation
  3. waitto stand overnight
  4. customEvaporation of the solvent via vacuum

Sources & evidence

ORD record
ord-a09e867a7e20434a96cd24479c7bc750
Source dataset
uspto-grants-1978_08
Patent number
US04110379

Reaction notes

Loading…