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  • 09월 06일 15시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

제112회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Continuous flow synthesis of triols in a tube-in-tube microreactor

2013년 9월 2일 12시 15분 50초
ORGN.P-873 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
10월 16일 (수요일) 16:00~19:00
저자 및
박찬이, 박찬필*, 임효진
충남대학교 분석과학기술대학원, Korea
Triols involving three hydroxy group (-OH) are very important building block in the synthesis of various materials, each hydroxy group can be further transformed into other functional groups including ketone, aldehyde, halide, amine, and so on. Photo-oxygenation conducted with only light and O2 gas is one of the most useful green chemical processes, which can be used in production of valuable fragrances, pharmaceuticals, and fine chemicals. However, the reaction integrated with another chemical process was ralery studied. In previous reports, microfluidic systems performing photooxygenation easily solved the problems related with short lifetime of singlet oxygen in organic solvents. Herein we report a continuous flow synthesis consisted of photooxygenation and TfOH catalyzed reaction. Singlet oxygen produced by O2 gas and photosensitizer (Methylene Blue) yields allyl hydroperoxide regioselectively in a mono-channel microreactor with segmented flow of O2 gas bubbles and liquid slugs, the hydroperoxide was efficiently converted to the triols in the following TfOH catalyzed reaction in batch or continuous flow manner. We newly designed and tested another microreactor with inner membrane tube (AF-2400) and outer transparent tube, the O2 gas injected in inner tube was continuously diffused into solution occupied in outer tube through gas permeable AF-2400 tube. The microreactor of tube-in-tube type enhanced the contact efficiency between light (LED lamp), oxygen gas, and liquid including reagent and photosensitizer. More importantly, the microreactor was excellent in terms of productivity that is one of the most important issues in microchemical society. We carried out the syntheses of rose oxide and ascaridole from alpha-terpinene and (-)-beta-citronellol. The photooxygenation of hexamethylbenzene was tested, the product ratio of mono- and dual-reaction was perfectly controlled under exact reaction time and temperature as another example.