Methanol → 1,3,5-Tris-(aminomethyl)-benzene

HRID 2166854Notes

Reaction equation

HRID 2166854 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([C:9]#[N:10])[CH:6]=[C:5]([C:11]#[N:12])[CH:4]=1)#[N:2].CO.[H][H]>[Ni].[Cr].[OH-].[Na+].C1(C)C(C)=CC=CC=1>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([CH2:11][NH2:12])[CH:6]=[C:7]([CH2:9][NH2:10])[CH:8]=1

Participants

8

Reactant 3

HCID 887MethanolHCID 82587Benzene-1,3,5-tricarbonitrileHCID 178418361HCID 178418361, compound2×

Product 1

HCID 109894691,3,5-Tris-(aminomethyl)-benzeneYield 79.1%

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 14798Sodium HydroxideCatalystHCID 23976ChromiumCatalystHCID 7237O-XyleneSolvent

Procedure

In a 300-ml capacity autoclave equipped with a magnetic stirrer was sealed 15 g of 1,3,5-tricyanobenzene (MTN), together with 15 g of Raney nickel.chromium catalyst (atomic ratio of Ni:Cr=49:1), 27 ml of methanol, 63 ml of xylene and 0.18 g of caustic soda. Hydrogen gas was fed into it at initial pressure of 100 kg/cm2G, and the reaction was carried out at 100° C., whereby 0.59 mole of hydrogen was absorbed for 35 minutes. The catalyst was filtered out, and the solvent was evaporated, followed by concentration under reduced pressure. By the above procedure, there was obtained 12.8 g of colorless crystals of 1,3,5-tris(aminomethyl)benzene (MTA). The substance showed melting point of 49° to 51° C. and boiling point of 136° to 139° C./0.4 mmHg.

Workup

  1. customIn a 300-ml capacity autoclave equipped with a magnetic stirrer
  2. customwas carried out at 100° C.
  3. filtrationThe catalyst was filtered out
  4. customthe solvent was evaporated
  5. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-60f9779b8ece432e8d95499f6596120e
Source dataset
uspto-grants-1983_06
Patent number
US04389519

Reaction notes

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