Water → Tricarbonylbenzene

HRID 1050433

Reaktionsgleichung

Reaktionsgleichung von HRID 1050433
[C:1]1([C:13](Cl)=[O:14])[CH:6]=[C:5]([C:7](Cl)=[O:8])[CH:4]=[C:3](C(Cl)=O)[CH:2]=1.C1(N)C=CC=C(N)C=1.NC1C=CC=CC=1.O.CN1[C:37](=[O:38])CCC1>>[C:13](=[C:1]1[CH2:2][CH:3]=[CH:4][C:5](=[C:7]=[O:8])[C:6]1=[C:37]=[O:38])=[O:14]

Komponenten

6

Edukt 5

HCID 962Water2×HCID 6115AnilineHCID 7935M-PhenylenediamineHCID 13387N-methyl-2-pyrrolidone2×HCID 78138Trimesoyl chloride

Produkt 1

HCID 21448804Tricarbonylbenzene

Versuchsvorschrift

In a nitrogen atmosphere, a 50 mL four-neck flask was charged with 3 g (11.3 mmol) of 1,3,5-benzenetricarbonyl trichloride (Tokyo Chemical Industry) and 13.3 g of NMP (Junsei Chemical Co., Ltd.), following which a solution of 0.92 g (8.48 mmol) of 1,3-phenylenediamine (DuPont K.K.) and 0.79 g (8.48 mmol) of aniline (Junsei Chemical Co., Ltd.) in 13.3 g of NMP (Junsei Chemical Co., Ltd.) was added dropwise over a period of 30 minutes at an internal temperature of 12° C. and polymerization was carried out. Following the completion of dropwise addition, the flask contents were stirred for 30 minutes at room temperature, pure water (3 g) was added dropwise, followed by another 30 minutes of stirring, after which the reaction mixture was added to 450 g of pure water, thereby effecting re-precipitation. The resulting precipitate was collected by filtration, then again dissolved in a mixed solvent of 24 g of THF (Kanto Chemical Co., Ltd.) and 1.8 g of pure water, after which the solution was added to 450 g of pure water, thereby effecting re-precipitation. The resulting precipitate was collected by filtration and dried at 150° C. for 2 hours in a vacuum desiccator, thereby giving 3.3 g of the target tricarbonylbenzene-based hyperbranched polymer (abbreviated below as “TmPDA-An”). FIG. 2 shows the 1H-NMR spectrum obtained for TmPDA-An.

Aufarbeitung

  1. additionwas added dropwise over a period of 30 minutes at an internal temperature of 12° C. and polymerization
  2. additionthe completion of dropwise addition
  3. waitfollowed by another 30 minutes
  4. stirringof stirring
  5. customre-precipitation
  6. filtrationThe resulting precipitate was collected by filtration
  7. dissolutionagain dissolved in a mixed solvent of 24 g of THF (Kanto Chemical Co., Ltd.) and 1.8 g of pure water
  8. additionafter which the solution was added to 450 g of pure water
  9. customre-precipitation
  10. filtrationThe resulting precipitate was collected by filtration
  11. customdried at 150° C. for 2 hours in a vacuum desiccator

Quellen und Nachweise

ORD-Eintrag
ord-88a9313ca4784c4493051e402f1385ab
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382381B2

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