This study reported the synthesis of perfluoropolyether intermediate (TP-COOCF3) having a CF3 functional group via electrophilic fluorine substituting direct fluorination from PFPE intermediate (TP-COOCH3) having a CH3 functional group, which was synthesized by the ring opening polymerization and methyl esterification of HFPO. The effects of reaction conditions such as the amount of solvent, fluorine partial pressure, reaction time, were investigated. The results showed that the yield of fluorination reaction became the highest when the reaction was carried out in a mild condition for a long reaction time, which also minimized side reactions. The sample was characterized by FTIR and NMR, which confirmed the synthesis of the final product, TP-COOCF3, via direct fluorination converting CH3 of TP-COOCH3 to CF3 of TP-COOCF3 with 95.4% yield.

본 연구에서는 hexafluoropropylene oxide(HFPO)의 개환중합 및 메틸에스테르화 반응을 통하여 CH3 말단 관능기를 가진 perfluoropolyether(PFPE) 중간체(TP-COOCH3)를 합성하고, 이를 친전자성 불소치환 직접플루 오르화법을 통하여 CF3 말단 관능기를 가진 PFPE 중간체(TP-COOCF3)를 합성하였다. 또한 반응조건인 용매의 양, 혼합가스 불소 부분압 및 반응시간이 TP-COOCF3 합성에 미치는 영향에 대하여 고찰하였다. 실험결과, 플루오르화 반응은 온화한 조건에서 장시간 진행하는 것이 부반응을 최소화하여 전환율을 향상시키는 것으로 나타났다. FTIR, NMR 결과로부터 TP-COOCH3의 말단 CH3 관능기가 친전자성 불소치환 직접플루오르화를 통하여 CF3 관능기로 치환되어 최종 생성물인 TP-COOCF3가 95.4%의 전환율로 합성된 것을 확인할 수 있었다.

Keywords: hexafluoropropylene oxide; perfluoropolyether; liquid-phase direct fluorination.