Tripropylamine → 27801-58-7

HRID 1633835

Reaction equation

HRID 1633835 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=1[OH:19])([CH3:4])([CH3:3])[CH3:2].C(N(CCC)CCC)CC.C[O-].[Na+:32]>CO>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=1[O-:19])([CH3:4])([CH3:3])[CH3:2].[Na+:32]

Participants

5

Reactant 3

HCID 7616TripropylamineHCID 129022,4,6-Tri-tert-butylphenolHCID 10942334Sodium Methoxide

Product 1

HCID 2366214927801-58-7

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

66.9 g of 2,4,6-tri-t-butylphenol was dissolved or dispersed into 213.5 g of tri-n-propyl amin. To this solution was added 13.5 of sodium methoxide. The mixture was heated in flask until reflux occurred at about 150° C. When the reflux temperature dropped below 150° C., distillate was condensed and removed from the reaction mixture until the vapor temperature in the flask rose above 150° C. then the mixture was again refluxed. When the vapor temperature dropped below 150° C., distillate was condensed and removed from the reaction mixture until the vapor temperature rose above 150° C. This alternate process of reflux and condensation was repeated until 8.0 g of methyl alcohol, CH3OH had been distilled Away from the reaction mixture. Approximately 112 g of tri-n-propyl amine was stripped from the reaction mixture leaving about 71 g of sodium 2,4,6-tri-t-butyl phenolate in about 100 g of tri-n-propyl amine as a 40 weight percent slurry of the phenolate salt in the amine solvent.

Workup

  1. temperatureThe mixture was heated in flask
  2. temperatureuntil reflux
  3. customoccurred at about 150° C
  4. additionWhen the reflux temperature dropped below 150° C.
  5. customcondensed
  6. customremoved from the reaction mixture until the vapor temperature in the flask
  7. customrose above 150° C.
  8. temperaturethe mixture was again refluxed
  9. additionWhen the vapor temperature dropped below 150° C.
  10. customcondensed
  11. customremoved from the reaction mixture until the vapor temperature
  12. customrose above 150° C
  13. temperatureThis alternate process of reflux
  14. customcondensation
  15. distillationhad been distilled Away from the reaction mixture

Sources & evidence

ORD record
ord-0c029dc401a44020a8e149dbcc63d0a2
Source dataset
uspto-grants-2003_01
Patent number
US06504065B1

Linked notes

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