청정기술 (Clean Technology)

  • 제16권4호
  • /
  • Pages.239-244
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  • 2010
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  • 1598-9712(pISSN)
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  • 2288-0690(eISSN)
한국청정기술학회 (The Korean Society of Clean Technology)
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초임계이산화탄소를 이용한 플로레닐계 에폭사이드로부터 카보네이트 화합물의 합성

Synthesis of a Fluorene Carbonate from Fluorenyl Epoxide Using Supercritical Carbon Dioxde

  • 심윤수 (영남대학교 이과대학 화학과) ;
  • 심재진 (영남대학교 이과대학 디스플레이화학공학부) ;
  • 나춘섭 (영남대학교 이과대학 화학과)
  • Sim, Yun-Soo (Department of Chemistry Chemical Engineering, Yeungnam University) ;
  • Shim, Jae-Jin (School of Display and Chemical Engineering, Yeungnam University) ;
  • Ra, Choon-Sup (Department of Chemistry Chemical Engineering, Yeungnam University)
  • 투고 : 2010.10.14
  • 심사 : 2010.11.04
  • 발행 : 2010.12.31
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초록

스파이로 구조의 플로렌 에폭사이드, 9,9'-Bis(4-oxiranylmethoxyphenyl) fluorine (2)를 4차 암모니늄 또는 인산염을 촉매를 사용하여 이산화탄소와 반응시켜 5각고리의 플로렌 카보네이트 화합물로 전환시켰다. 이 과정은 주요 온실가스의 하나인 초임계 조건의 이산화탄소를 C-1 재료로 쓰고 동시에 반응용매로 이용하는 청정반응의 한 예로 볼 수 있다. 4차염의 종류와 반응조건이 반응에 미치는 영향에 대해 조사한 결과, 촉매의 음이온의 종류, 알킬 치환기, 반응온도가 반응에 큰 영향을 미치는 것으로 나타났다. 브롬화 사부틸 암모늄 촉매 (2 mol%)를 쓰고 플로레닐 에폭사이드를 75.9 bar 압력의 이산화탄소를 393 K에서 반응시켰을 때 플로레닐 카보네이트를 92% 수율로 얻을 수 있었다.

The carboxylation of the fluorenyl epoxide with a spiro framework, 9,9'-Bis(4-oxiranylmethoxyphenyl) fluorine (2) was catalyzed by some onium salts such as quaternary ammonium and phosphonium salts to produce the corresponding five-membered cyclic carbonate (3) in an efficient and environmentally benign fashion. The coupling reactions depend greatly on the kind of the halide anions and alkyl chain length of the onium salts. While the reaction was sensitive to the reaction temperature, the reaction trends suggest that the catalytic efficiency of the quaternary ammonium halides may correlate strongly with the melting points of the halides. The reactions using a catalytic amount (2 mol %) of quaternary ammonium bromide with an n-butyl chain at 75.9 bar of $CO_2$ and 393 K give the highest yield of the cyclic carbonate (92%).

키워드

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