Catechol → o-Benzoquinone trimethyl-hexamethylene-diamine

HRID 1451991Notes

Reaction equation

HRID 1451991 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH3:11])[CH3:10].[C:12]1([C:14](=[CH:16][CH:17]=[CH:18][CH:19]=1)[OH:15])[OH:13].O=O>CO.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[C:14]1(=[O:15])[CH:16]=[CH:17][CH:18]=[CH:19][C:12]1=[O:13].[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 289CatecholHCID 977Oxygen2×HCID 15043600N~1~,N~1~,N~6~-Trimethylhexane-1,6-diamine

Product 1

HCID 67706079o-Benzoquinone trimethyl-hexamethylene-diamine

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 887MethanolSolvent

Procedure

About 37.93 g (0.24 mol) trimethyl-hexamethylene-diamine and about 0.6 g (0.0024 mol) copper sulfate pentahydrate were dissolved in about 400 mL of methanol. About 26.4 g (0.24 mol) of catechol (chemical name 1,2-dihydroxybenzene) acting as both the quinone precursor and catalyst was added to the reactant mixture. A gentle stream of oxygen at a flow rate of about 50 cc/min was then passed through the reaction mixture for about three hours, while maintaining the reaction temperature around 20°-25 ° C. At the end of three hours the oxygen supply was cut off and the reaction mixture was concentrated under vacuum using a rotary evaporator. The o-benzoquinone-trimethyl-hexamethylene-diamine polymer was precipitated in excess water, washed extensively and dried under vacuum for about 6 hours at a temperature of about 30° C.

Workup

  1. additionwas added to the reactant mixture
  2. temperaturewhile maintaining the reaction temperature around 20°-25 ° C
  3. customAt the end of three hours
  4. concentrationthe reaction mixture was concentrated under vacuum
  5. customa rotary evaporator
  6. customThe o-benzoquinone-trimethyl-hexamethylene-diamine polymer was precipitated in excess water
  7. washwashed extensively
  8. customdried under vacuum for about 6 hours at a temperature of about 30° C.

Sources & evidence

ORD record
ord-88c5fb0b3da74495b955b38760dc32c3
Source dataset
uspto-grants-1997_02
Patent number
US05606010

Reaction notes

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