2,2,6,6-Tetramethyl-4-piperidone → 1,6-Bis(2,2,6,6-tetramethyl-4-piperidylamino)hexane

HRID 1109796Notes

Reaction equation

HRID 1109796 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][C:6](=O)[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3]1.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH2:19].[H][H]>[Pt].CO>[CH3:1][C:2]1([CH3:11])[CH2:7][CH:6]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH:6]2[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3][C:2]([CH3:11])([CH3:1])[CH2:7]2)[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3]1

Participants

6

Reactant 3

HCID 132202,2,6,6-Tetramethyl-4-piperidoneHCID 16402HexamethylenediamineHCID 178418361HCID 178418361, compound

Product 1

HCID 934191,6-Bis(2,2,6,6-tetramethyl-4-piperidylamino)hexane

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

After 1,047 parts of 2,2,6,6-tetramethyl-4-piperidone, 373 parts of hexamethylenediamine, 2,260 parts of methanol and 5.5 parts of 5% platinum-on-carbon catalyst were charged into an autoclave, the temperature of the mixture was gradually elevated from 30° C. and the mixture was subjected to hydrogenation at a hydrogen pressure of 5 kg/cm2 while the temperature was kept at 60°-70° C. It took 8 hours to complete the hydrogenation. The resultant mixture was filtered at about 50°-60° C. to remove the catalyst therefrom, and then the resultant filtrate was subjected to distillation to remove the solvent and the water formed as by-product during the reaction, thereby obtaining 1,325 parts of crude N,N'-bis (2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine having a purity of 92.9%, a 2,2,6,6-tetramethyl-4-piperidone content of 0.8%, and an APHA value of 400.

Workup

  1. customwas gradually elevated from 30° C.
  2. customwas kept at 60°-70° C
  3. filtrationThe resultant mixture was filtered at about 50°-60° C.
  4. customto remove the catalyst
  5. distillationthe resultant filtrate was subjected to distillation
  6. customto remove the solvent
  7. customthe water formed as by-product during the reaction

Sources & evidence

ORD record
ord-e1b9934b226043e9ba0994052041dd5b
Source dataset
uspto-grants-1994_06
Patent number
US05322947

Reaction notes

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