Clean Technology (청정기술)

The Korean Society of Clean Technology (한국청정기술학회)
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Improved Procedure for the Preparation of 9,9'-bis[4-(glycidyloxy)phenyl]fluorene

9,9'-비스[4-(글라이시딜옥시)페닐]플루오렌의 효율적 제법

  • Received : 2012.07.16
  • Accepted : 2012.08.25
  • Published : 2012.09.30
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Abstract

The condensation reaction of 9,9'-bis(4-hydroxyphenyl)fluorene with epichlorohydrin to prepare 9,9'-bis[4(glycidyloxy) phenyl]fluorene (2), an important building block for fluorene-containing epoxy polymers, has been studied. The reaction is found to be quite sensitive to several experimental conditions such as reaction temperature and time, added amount of epichlorohydrin, the presence of catalysts and the use of co-solvent. Several conditions for obtaining the best yield in the reaction are: the reaction temperature is below 373 K and the reaction time is shorter than 1.5 h, and the ammonium salts act as a catalyst. Also, the use of ternary solvent (toluene, DMSO, water) has been proved to be crucial to maintain the reaction temperature and for an easy purification. Thus, the reaction proceeds in an environment-friendly manner where the use of reactants and the production of chemical wastes is minimized.

플로렌 구조를 가진 다양한 에폭시 수지의 합성 전구물질 9,9'-비스[4-(2'-하이드록시-3'-아크릴로일옥시프로폭시)페닐]플루오렌(2)을 에 대한 효율적 제법을 연구하였다. 화합물(2)는 비스(4-하이드록시페닐)플루오렌과 에피클로로하이드린의 축합 반응에서 얻어졌으며 반응 수율은 여러 가지 실험적 조건(반응 온도와 시간, 에피클로로하이드린의 사용량, 촉매와 용매의 사용 등)에 민감하게 변화하였다. 이들의 반응 수율에 미치는 효과에 대한 실험적 결과를 기술하고 논의하였다. 373 K이하의 반응온도에서 1.5시간 이하의 반응시간을 유지함으로써 부생성물의 생성을 최소화할 수 있었으며, 톨루엔/DMSO/물의 혼합용매를 사용하여 반응온도를 적절히 조절하고 생성물을 용이하게 정제할 수 있었다. 여러 사차 암모늄염을 이 반응의 촉매로 이용할 수 있었다. 본 연구를 통하여 적은 양의 반응물질을 사용하고, 화학적 폐기물의 생성은 최소화하는 용이한 정제방법을 확립했으며 반응 온도를 낮추어 에너지의 사용을 감소시킴으로써 9,9'-비스[4-(2'-하이드록시-3'-아크릴로일옥시프로폭시)페닐]플루오렌 제조 방법에 대한 환경친화성을 높일 수 있었다.

Keywords

References

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