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

HRID 435182Notes

Reaction equation

HRID 435182 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]>[Cr].[Ni].[OH-].[Na+].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 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 3

HCID 14798Sodium HydroxideCatalystHCID 11320920Chromium 22, nickel 78 (atomic)CatalystHCID 7929M-XyleneSolvent

Procedure

15 g of 1,3,5-tricyanobenzene (MTN) was charged into a magnetically stirring type autoclave having a 300 ml capacity together with 15 g of Raney nickel-chromium catalyst (atomic ratio: Ni:Cr=49:1), 27 ml of methanol, 63 ml of m-xylene and 0.18 g of sodium hydroxide. Hydrogen was injected thereinto under an initial pressure of 100 kg/cm2G and reaction was effected at 100° C. to cause absorption of 0.59 mole of hydrogen for 35 minutes. The catalyst was filtered off and the solvent was distilled out. Then, distillation under reduced pressure was effected to obtain 12.8 g of colorless crystal of 1,3,5-tris(aminomethyl) benzene (MTA). The product had a melting point of 49° to 51° C. and a boiling point of 136° to 139° C./0.4 mmHg.

Workup

  1. customunder an initial pressure of 100 kg/cm2G and reaction
  2. customwas effected at 100° C.
  3. filtrationThe catalyst was filtered off
  4. distillationthe solvent was distilled out
  5. distillationThen, distillation under reduced pressure

Sources & evidence

ORD record
ord-014d674616124c7d96927af8ee7eaebc
Source dataset
uspto-grants-1983_08
Patent number
US04400525

Reaction notes

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