Ammonia → 1,4-Benzenedimethanamine

HRID 1389974Notes

Reaction equation

HRID 1389974 reaction equation
COCCOCCOC.N.[C:11](#[N:20])[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1.[H][H]>O>[C:12]1([CH2:11][NH2:20])[CH:19]=[CH:18][C:15]([CH2:16][NH2:17])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8150DiglymeHCID 121721,4-DicyanobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 683151,4-Benzenedimethanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

A stirred autoclave is charged with 900 ml. of diethylene glycol dimethyl ether (Diglyme), 100 ml. ammonia, 100 g. terephthalonitrile (TPN) and the desired amount of catalyst and 100 ml of water. The autoclave is heated to 125° C. Hydrogen is introduced rapidly until the selected pressure is reached. The absorption of hydrogen starts immediately and additional hydrogen is added to keep the pressure at the selected level. The course of the reaction is monitored by measuring the volume of hydrogen consumed and by periodic withdrawal of a small sample of the reaction mixture for analysis. When the analysis indicates that all of the terephthalonitrile is reacted, the agitation is stopped and the reactor is cooled rapidly and vented. The reaction mixture is filtered to recover the catalyst and then is flash evaporated to remove solvent. The residual oil is distilled at about 100° C. and 0.5 mm Hg. to give practically pure p-xylylene diamine. A small amount of high rolling residue remains in the distillation pot.

Workup

  1. additionA stirred autoclave is charged with 900 ml
  2. customThe absorption of hydrogen
  3. additionadditional hydrogen is added
  4. customconsumed and by periodic withdrawal of a small sample of the reaction mixture for analysis
  5. customis reacted
  6. temperaturethe reactor is cooled rapidly
  7. filtrationThe reaction mixture is filtered
  8. customto recover the catalyst
  9. customevaporated
  10. customto remove solvent
  11. distillationThe residual oil is distilled at about 100° C.

Sources & evidence

ORD record
ord-67dcf911b1d244699b2e06eada242423
Source dataset
uspto-grants-1981_01
Patent number
US04247478

Reaction notes

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