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

HRID 1462885Notes

Reaction equation

HRID 1462885 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.[OH-].[Na+].[H][H]>[Cr].[Ni].C1(C)C=CC=C(C)C=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

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 82587Benzene-1,3,5-tricarbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 109894691,3,5-Tris-(aminomethyl)-benzeneYield 81%

Reagents, catalysts & solvents 2

HCID 11320920Chromium 22, nickel 78 (atomic)CatalystHCID 7929M-XyleneSolvent

Procedure

1000 g of 1,3,5-tricyanobenzene (MTN) was charged in an autoclave having a 20 l capacity together with 400 g of Raney nickel-chromium catalyst (atomic ratio Ni:Cr=49:1), 1800 ml of methanol, 4.2 l of m-xylene and 32.6 g of sodium hydroxide. Hydrogen was injected thereinto under an initial pressure of 140 kg/cm2G and reaction was effected at 60°-102° C. to cause absorption of nearly theoretical amount of hydrogen for 31 minutes. The catalyst was filtered off and the solvent was distilled out. Then, distillation under reduced pressure was effected to obtain 874 g of colorless crystal of 1,3,5-tris(aminomethyl)benzene (MTA). The product had a melting point of 49°-51° C. and a boiling point of 136°-139° C./0.4 mmHg.

Workup

  1. customunder an initial pressure of 140 kg/cm2G and reaction
  2. customwas effected at 60°-102° C.
  3. customabsorption of nearly theoretical amount of hydrogen for 31 minutes
  4. filtrationThe catalyst was filtered off
  5. distillationthe solvent was distilled out
  6. distillationThen, distillation under reduced pressure

Sources & evidence

ORD record
ord-09e6397581c54340be9a6e012e99f8a1
Source dataset
uspto-grants-1984_07
Patent number
US04461878

Reaction notes

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