화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Clean Technology, Vol.17, No.4, 325-328, December, 2011
Export Citation
9, 9'-비스[4-(2'-하이드록시-3'-아크릴로일옥시프로폭시) 페닐]플루오렌의 원자효율적 합성
Atom-efficient Preparation of 9, 9'-Bis[4-(2'-hydroxy-3'-acryloyloxypropoxy)phenyl]fluorene
정혁진, 홍성재1, 서광범1, 심재진2, 나춘섭†
  • 영남대학교 이과대학 화학과, 712-749 경북 경산시 대동 214-1
  • 1주식회사 이그잭스 PR 사업부, 730-906 경북 구미시 공단동 310
  • 2영남대학교 화학공학부, 712-749 경북 경산시 대동 214-1
Hyeok Jin Jung, Seong-Jae Hong1, Kwang-Beom Seo1, Jae Jin Shim2, and Choon Sup Ra†
  • Department of Chemistry, Yeungnam University, 214-1 Dae-dong, Gyeongsan, Gyeongbuk 712-749, Korea
  • 1Photoresist Group, R & D Center, Exax Inc., 310 Gongdan-dong, Gumi, Gyeongbuk 730-906, Korea
  • 2School of Chemical Engineering, Yeungnam University, 214-1 Dae-dong, Gyeongsan, Gyeongbuk 712-749, Korea
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초록
플로렌 구조를 가진 다양한 아크릴계 에폭시 고분자화합물 합성의 전구물질인 9, 9'-비스[4-(2'-하이드록시-3'-아크릴로일옥시프로폭시)페닐]플루오렌 (3)에 대한 원자 효율적 (atom-efficient) 제조방법을 연구하였다. 사차 암모늄 또는 인산염을 촉매를 사용하여 9, 9'-비스[4-(글라이시딜옥시)페닐]플루오렌 (1)을 아크릴산과 개환 에스터화의 효율적 반응을 통하여 9, 9'-비스[4-(2'-하이드록시-3'-아크릴로일옥시프로폭시)페닐]플루오렌 (3)을 높은 수율로 얻을 수 있었다. 알킬 사차염의 종류와 반응조건이 반응에 미치는 영향에 대해 조사한 결과, 촉매의 종류가 반응에 큰 영향을 미치는 것으로 나타났다. 브롬화사부틸인 촉매(3 mol%) 존재 하에 플로레닐에폭사이드를 아크릴산과 110 ℃에서 반응시켰을 때 원하는 생성물을 90% 수율로 얻을 수 있었다. 이 반응은 반응물질 사용량과 화학적 폐기물의 생성량을 최소화한 청정반응이다.
Atom-efficient preparation of 9, 9'-bis[4-(2'-hydroxy-3'-acryloyloxypropoxy) phenyl]fluorene (3), the extensively used building block for fluorene-containing acrylic epoxy polymers has been described. The epoxide ring opening esterification of 9,9-bis[4-(glycidyloxy)phenyl]fluorene (1) with acrylic acid was catalyzed by some onium salts such as quaternary ammonium and phosphonium salts. While the coupling reactions depend greatly on the kind of the onium salts, the reaction of 9, 9-bis[4-(glycidyloxy)phenyl]fluorene (1) with acrylic acid proceed most efficiently in the presence of a catalytic amount of tetrabutylphosphonium bromide at 110 ℃ with 90% yield. This reaction is a cleaner reaction that minimizes the use of reactants and the production of chemical wastes.
Keywords:Atom-efficient reaction;Fluorene;9;9-bis[4-(glycidyloxy)phenyl]fluorene;Green Chemistry;Ring-opening esterification;Tetraalkyl onium salt
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