Sulfuric Acid → Urea 2-methylpentanal

HRID 27211Notes

Reaction equation

HRID 27211 reaction equation
[CH3:1][CH:2]([CH2:5][CH2:6][CH3:7])[CH:3]=[O:4].C1(C)C(C)=CC=CC=1.[NH2:16][C:17]([NH2:19])=[O:18].S(=O)(=O)(O)O>O>[NH2:16][C:17]([NH2:19])=[O:18].[CH3:1][CH:2]([CH2:5][CH2:6][CH3:7])[CH:3]=[O:4]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 1176UreaHCID 7237O-XyleneHCID 312452-Methylpentaldehyde

Product 1

HCID 86737184Urea 2-methylpentanal

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 800 parts of 2-methylpentanal, 800 parts of xylene and 120 parts of urea is heated to the boil in a stirred apparatus of the type described in Example 1, and 50 parts of 75% strength sulfuric acid are added dropwise. The mixture is then stirred at the boil and the water formed (84 parts) is removed via the water separator. The condensation is complete after about 3 hours. The reaction mixture is neutralized with 50% strength sodium hydroxide solution and stirred for a further hour at the boil, whilst removing water. 60 Parts of 30% strength sodium methylate solution in methanol are then added to the contents of the flask and the mixture is again stirred for 1 hour at the boil. It is then cooled to 60° C., neutralized to pH 7 with 75% strength sulfuric acid and washed with twice 1,000 parts of water. After removing the wash water, the xylene solution is evaporated under reduced pressure (20-25 mm Hg) until the temperature in the flask reaches 175° C.

Workup

  1. temperatureis heated to the boil in a stirred apparatus of the type
  2. additionare added dropwise
  3. customis removed via the water separator
  4. stirringstirred for a further hour at the boil
  5. customwhilst removing water
  6. addition60 Parts of 30% strength sodium methylate solution in methanol are then added to the contents of the flask
  7. stirringthe mixture is again stirred for 1 hour at the boil
  8. washwashed with twice 1,000 parts of water
  9. customAfter removing the wash water
  10. customthe xylene solution is evaporated under reduced pressure (20-25 mm Hg) until the temperature in the flask
  11. customreaches 175° C.

Sources & evidence

ORD record
ord-97edae3948714635ad3dc632483cbbf7
Source dataset
uspto-grants-1980_09
Patent number
US04220751

Reaction notes

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