Ammonia → 1,4-Benzenedimethanamine

HRID 27671

Reaction equation

HRID 27671 reaction equation
O1CCCC1.N.[C:7](#[N:16])[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[H][H]>[Co].O>[C:8]1([CH2:7][NH2:16])[CH:15]=[CH:14][C:11]([CH2:12][NH2:13])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 121721,4-DicyanobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 683151,4-Benzenedimethanamine

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A stirred autoclave was charged with 400 ml. tetrahydrofuran (THF), 100 ml. ammonia, 50 g. terephthalonitrile (TPN) and 6.0 g. cobalt supported catalyst and various amounts of water. The autoclave was heated to 120° C. Hydrogen was introduced rapidly until the selected pressure was reached. The absorption of hydrogen started immediately and additional hydrogen was added to keep the pressure at the selected level. The course of the reaction was 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 indicated that all of the terephthalonitrile had reacted, the agitation was stopped and the reactor was cooled rapidly and vented. The reaction mixture was filtered to recover the catalyst and then was flash evaporated to remove solvent. The residual oil was flash distilled at about 100° C. and 0.5 mm Hg. to give practically pure p-xylylene diamine. A small amount of high boiling residue remained in the distillation pot. Results of experiments conducted with various amounts of water and at 1500 and 2500 psig are listed in Table I.

Workup

  1. additionA stirred autoclave was charged with 400 ml
  2. customThe absorption of hydrogen
  3. additionadditional hydrogen was added
  4. customconsumed and by periodic withdrawal of a small sample of the reaction mixture for analysis
  5. customhad reacted
  6. temperaturethe reactor was cooled rapidly
  7. filtrationThe reaction mixture was filtered
  8. customto recover the catalyst
  9. customevaporated
  10. customto remove solvent
  11. distillationdistilled at about 100° C.

Sources & evidence

ORD record
ord-7e6cd9f6c5f9464fbaee0cb1ba972c3b
Source dataset
uspto-grants-1980_09
Patent number
US04222961

Linked notes

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