Phosphoric Acid → 1H-Pyrrole-2,5-dione, 1-dodecyl-

HRID 868689

Reaction equation

HRID 868689 reaction equation
[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.[CH2:8]([NH2:20])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].P(=O)(O)(O)O.COC1C=CC(O)=CC=1>C1(C)C(C)=CC=CC=1.C([O-])(=O)C.[Zn+2].C([O-])(=O)C.O>[CH2:8]([N:20]1[C:4](=[O:5])[CH:3]=[CH:2][C:1]1=[O:7])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

8

Reactant 4

HCID 1004Phosphoric AcidHCID 7923Maleic AnhydrideHCID 90154-MethoxyphenolHCID 13583Dodecylamine

Product 1

HCID 871911H-Pyrrole-2,5-dione, 1-dodecyl-

Reagents, catalysts & solvents 3

HCID 11192Zinc AcetateCatalystHCID 962WaterSolventHCID 7237O-XyleneSolvent2×

Conditions

Temperature
150 °C

Procedure

A glass flask having an inner volume of 3 liters was fitted with a theremometer, a stirrer and a water separater. This reactor was charged with 240 g of a xylene solution containing 120 g of maleic anhydride. Then, a solution of 220 g of dodecylamine in 1880 g of xylene was added thereto gradually and piecemeal at 40° C. over a period of 120 minutes. After the addition was completed, the resultant mixture and 65.4 g of ortho-phosphoric acid (purity 89% by weight), 0.672 g of p-methoxyphenol, and 0.05 g of zinc acetate added thereto were heated at 150° C. for four hours to effect reaction. Thereafter, the resultant reaction mixture was cooled to 30° C., washed with 400 ml of water, and separated into a water layer and a xylene layer. The xylene layer was filtered to effect removal of insolubles. The xylene layer now free from insolubles was distilled to expel xylene. Consequently there was obtained 260 g of slightly impure N-dodecyl maleimide. It was found to have purity of 91.2% by weight, indicating the yield thereof to be 75.3 mol % based on dodecylamine.

Workup

  1. customA glass flask having
  2. customan inner volume of 3 liters was fitted with a theremometer, a stirrer
  3. additionAfter the addition
  4. customreaction
  5. customThereafter, the resultant reaction mixture
  6. temperaturewas cooled to 30° C.
  7. washwashed with 400 ml of water
  8. customseparated into a water layer
  9. filtrationThe xylene layer was filtered
  10. customremoval of insolubles
  11. distillationThe xylene layer now free from insolubles was distilled

Sources & evidence

ORD record
ord-845715f9f7284fbf9c7e7e7f06ca61af
Source dataset
uspto-grants-1988_10
Patent number
US04780546

Linked notes

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