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

HRID 1074467Notes

Reaction equation

HRID 1074467 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]>[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

6

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 2

HCID 14798Sodium HydroxideCatalystHCID 7929M-XyleneSolvent

Procedure

In a 300 ml capacity, magnetic-stirring autoclave 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 m-xylene and 0.18 g of caustic soda. Hydrogen was charged under pressure 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 distilled off, followed by distilling under reduced pressure, thereby yielding 12.8 g of colorless crystals of 1,3,5-tris(aminomethyl)-benzene (MTA). The substance exhibited melting point of 49° to 51° C. and boiling point of 136° to 139° C./0.4 mmHg.

Workup

  1. customwas carried out at 100° C.
  2. filtrationThe catalyst was filtered out
  3. distillationthe solvent was distilled off
  4. distillationby distilling under reduced pressure

Sources & evidence

ORD record
ord-523bd32ae00a4636bc5c90aa2e685d9f
Source dataset
uspto-grants-1983_07
Patent number
US04391958

Reaction notes

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