1-Amino-2-propanol → Tricarbonylbenzene

HRID 1050432

반응식

HRID 1050432 반응식
[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.C[CH:32]([OH:35])CN>CN1C(=O)CCC1.O>[C:13](=[C:1]1[CH2:2][CH:3]=[CH:4][C:5](=[C:7]=[O:8])[C:6]1=[C:32]=[O:35])=[O:14]

참가 물질

7

반응물 4

HCID 41-Amino-2-propanolHCID 6115AnilineHCID 7935M-PhenylenediamineHCID 78138Trimesoyl chloride

생성물 1

HCID 21448804Tricarbonylbenzene

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매4회

반응 조건

온도
70 °C

실험 절차

In a nitrogen atmosphere, a 300 mL four-neck flask was charged with 30 g (0.113 mol) of 1,3,5-benzenetricarbonyl trichloride (Tokyo Chemical Industry) and 133.3 g of N-methyl-2-pyrrolidone (abbreviated below as “NMP”; Junsei Chemical Co., Ltd.), following which a solution of 9.16 g (84.8 mmol) of 1,3-phenylenediamine (DuPont K.K.) and 7.89 g (84.8 mmol) of aniline (Junsei Chemical Co., Ltd.) dissolved in 133.3 g of NMP (Junsei Chemical Co., Ltd.) was added dropwise over a period of 30 minutes at an internal temperature of 0 to 5° C. Following the completion of dropwise addition, the flask contents were stirred for 30 minutes at a temperature of 10° C. or below. A solution of 12.73 g (169.5 mmol) of DL-1-amino-2-propanol (Tokyo Chemical Industry) dissolved in 90 g of NMP (Junsei Chemical Co., Ltd.) was added dropwise to this at an internal temperature of from −3 to −1° C. over a period of 30 minutes, following which the temperature was raised to 70° C. and stirring was carried out for 2 hours. The reaction mixture was added to 3,000 g of pure water to effect re-precipitation and the resulting precipitate was collected by filtration, then dried at 150° C. for 3 hours in a vacuum desiccator. The resulting moist product was again dissolved in 180 g of N,N-dimethylacetamide (abbreviated below as “DMAc”) and stirred at 55° C. for 1 hour. Next, the DMAc solution was allowed to cool to 30° C., then added to 600 g of pure water heated to 50° C. and re-precipitated, followed by stirring at 50° C. for 1 hour. After allowing the contents to cool to 30° C., filtration was carried out and the filtrate was dried in a vacuum desiccator at 150° C. for 10 hours, giving 35.85 g of the target tricarbonylbenzene-based hyperbranched polymer (abbreviated below as “HPmDAP”). FIG. 1 shows the 1H-NMR spectrum obtained for HPmDAP.

후처리

  1. additionwas added dropwise over a period of 30 minutes at an internal temperature of 0 to 5° C
  2. additionthe completion of dropwise addition
  3. additionwas added dropwise to this at an internal temperature of from −3 to −1° C. over a period of 30 minutes
  4. stirringstirring
  5. waitwas carried out for 2 hours
  6. customre-precipitation
  7. filtrationthe resulting precipitate was collected by filtration
  8. customdried at 150° C. for 3 hours in a vacuum desiccator
  9. dissolutionThe resulting moist product was again dissolved in 180 g of N,N-dimethylacetamide (
  10. stirringstirred at 55° C. for 1 hour
  11. temperatureto cool to 30° C.
  12. additionadded to 600 g of pure water
  13. temperatureheated to 50° C.
  14. customre-precipitated
  15. stirringby stirring at 50° C. for 1 hour
  16. temperatureto cool to 30° C.
  17. filtrationfiltration
  18. customthe filtrate was dried in a vacuum desiccator at 150° C. for 10 hours

출처 및 근거

ORD 기록
ord-56f18a236ba44cec86871fd2a8b19c0a
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382381B2

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