Acetone → N,N'-1,3-Phenylenedimaleimide

HRID 262417

Reaktionsgleichung

Reaktionsgleichung von HRID 262417
[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.[C:8]1([NH2:15])[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1.O.O.O.O.O.O.[Cl-].[Mg+2].[Cl-].C(O[C:29](=[O:31])[CH3:30])(=O)C.[CH3:32][C:33](C)=[O:34]>C(N(CC)CC)C>[C:8]1([N:15]2[C:1](=[O:7])[CH:2]=[CH:3][C:4]2=[O:5])[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[C:29](=[O:31])[CH:30]=[CH:32][C:33]2=[O:34])[CH:9]=1

Komponenten

7

Edukt 5

HCID 180Acetone2×HCID 7918Acetic AnhydrideHCID 7923Maleic AnhydrideHCID 7935M-PhenylenediamineHCID 24644Magnesium chloride hexahydrate

Produkt 1

HCID 18156N,N'-1,3-PhenylenedimaleimideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A flask was equipped as in Example 1. To a solution of maleic anhydride (1.92 parts) in 4.8 parts acetone was added a solution of 1 part m-phenylenediamine, 0.32 part triethylamine and 1.6 parts acetone over a 15-minute period. A precipitate formed during that time. The heterogeneous reaction mixture was maintained at 40° C. for 30 minutes. Magnesium chloride hexahydrate (0.08 part) and 2.44 parts acetic anhydride were added all at once. The temperature was raised to 50° C. and maintained for 3 hours. After 30 minutes, the reaction mixture became homogeneous and amber in color. Five minutes later, the product began to precipitate. At the end of the reaction time, the mixture was cooled and 12 parts water added. The precipitated product was collected by vacuum filtration, washed with water, and dried for 24 hours at 60° C. in a vacuum oven. A 92% yield of N,N'-m-phenylenedimaleimide, m.p. 204°-205° C., was obtained.

Aufarbeitung

  1. customA flask was equipped as in Example 1
  2. customA precipitate formed during that time
  3. temperatureThe temperature was raised to 50° C.
  4. temperaturemaintained for 3 hours
  5. customFive minutes
  6. customto precipitate
  7. temperatureAt the end of the reaction time, the mixture was cooled
  8. addition12 parts water added
  9. filtrationThe precipitated product was collected by vacuum filtration
  10. washwashed with water
  11. customdried for 24 hours at 60° C. in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-dab1331b97f54aa09ed037a702a64e79
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04154737

Verknüpfte Notizen

Wird geladen…