Hexane → 2,3-Dibutyl-4-methylphenol

HRID 1287821Notes

Reaction equation

HRID 1287821 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H][H].CCC[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O-:18])=O.[CH3:19][CH2:20][CH2:21][CH2:22]CCCC([O-])=O.[Ni+2].C1CCCCC=1.C([Al](CC)CC)C>[Ni]>[CH2:3]([C:2]1[C:13]([CH3:12])=[CH:14][CH:15]=[C:16]([OH:18])[C:1]=1[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 8058HexaneHCID 131710492Nickel octoate cyclohexene triethyl aluminumHCID 178418361HCID 178418361, compound

Product 1

HCID 137835422,3-Dibutyl-4-methylphenol

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Conditions

Temperature
130 fahrenheit

Procedure

Five gallons of the block copolymer cement product from Example VI containing about 2500 gms. of polymer is charged to a hydrogenation reactor together with an additional 40 lbs. of dry hexane. The reactor is flushed 6 times by pressuring to 50 psig with hydrogen and then releasing the pressure to about 5 psig. Then the hydrogenation catalyst is added which comprises 25 millimoles of Ni in nickel octoate-cyclohexene-triethyl aluminum in proportions of 1/1/3 respectively. The temperature is raised to 130°F and hydrogen introduced to a pressure of 150 psig. Periodically the system is repressured to 150 psig and samples are removed three times at several hours intervals. The temperature is maintained at 130°-160°F over a period of about 7 hours after which the reaction mixture is cooled to 120°F and vented several times. The product is dropped into a 55 gallon drum containing methanol and a small amount of antioxidant (dibutyl-p-cresol) to provide about 0.5 gm. of A.O. per 100 gms. of polymer. The product is filtered and rinsed several times with hexane. The copolymer is found to be about 100% hydrogenated and to have a glass transition temperature of -59°C and a melting point of 97°C. This product shows excellent impact strength and is used in the tests of Example VIII.

Workup

  1. additionof polymer is charged to a hydrogenation reactor together with an additional 40 lbs
  2. customThe reactor is flushed 6 times
  3. additionThen the hydrogenation catalyst is added which
  4. customare removed three times at several hours intervals
  5. temperatureThe temperature is maintained at 130°-160°F over a period of about 7 hours after which the reaction mixture
  6. temperatureis cooled to 120°F
  7. additionThe product is dropped into a 55 gallon drum
  8. additioncontaining methanol

Sources & evidence

ORD record
ord-e75a29b8a95e4e6e8f642dc0ec5d11cb
Source dataset
uspto-grants-1976_10
Patent number
US03985826

Reaction notes

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