Applied Chemistry for Engineering, Vol.27, No.2, 195-198, April, 2016
재사용이 가능한 MFB로부터 4,4’-Bis(2-benzoxazolyl)stilbene의 합성 공정 개발
Process Development of 4,4’-Bis(2-benzoxazolyl)stilbene from Recyclable Source MFB
DMT 생산과정의 부산물로서 폐기 처리되어 왔던 MFB를 출발 물질로 하여 고급 형광증백제 중의 하나인 4,4’-bis(2-benzoxazolyl)stilbene (BBS) 합성을 4단계를 거쳐 총 수율 73%의 경쟁력 있는 공정개발을 수행하였다. 제시된 합성법은 MFB와 ethyl 4-((diethoxyphosphoryl)methyl)benzoate (1)과 반응시킨 후, coupling 생성물 4,4’-stilbenedicarboxylate (2)를 얻고 이를 4,4’-stilbenedicarbonyl chloride (3)으로 변환 후 BBS 합성의 핵심 단계인 benzoxazole 형성 단계에서 상용화가 가능한 용매와 촉매를 탐구하여 용매로는 1,2,4-trichlorbenzene 촉매로는 boric acid의 사용이 가능한 것을 확인하였다.
A total four-step synthetic process of high quality optical brightening agent 4,4’-bis(2-benzoxazolyl)stilbene (BBS) from methyl 4-formylbenzoate (MFB) was developed with 73% total yield. MFB is one of the main by-products in dimethyl terephthalate (DMT) production process. Our process involves the formation of 4,4’-stilbenedicarboxylate (2) obtained from the reaction of an aldehyde in MFB with ethyl 4-((diethoxyphosphoryl)methyl)benzoate (1) and the subsequent transformation to 4,4’-stilbenedicarbonyl chloride (3). In order to prepare benzoxazole ring in BBS, various solvents and catalysts were studied. The best solvent and catalyst were found to be 1,2,4-trichlorobenzene and boric acid, respectively suitable for mass production of BBS.
Keywords:methyl 4-formylbenzoate;recyclable source;DMT;optical brightening agent;4,4’-bis(2-benzoxazolyl)stilbene
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