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Received July 1, 2013
Accepted August 4, 2013
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N-사이크로헥실말레아민산 이소부틸 에스테르의 제조 공정 개발
Development of a Synthetic Process for N-Cyclohexylmaleiamic Acid Isobutyl Ester
부경대학교 화학공학과, 608-739 부산시 남구 용당동 산 100
Department of Chemical Engineering, Pukyoung National University, San 100 Yongdang-dong, Nam-gu, Busan 608-739, Korea
csju@pknu.ac.kr
Korean Chemical Engineering Research, October 2013, 51(5), 545-549(5), 10.9713/kcer.2013.51.5.545 Epub 1 October 2013
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Abstract
높은 수율로 CHMI를 제조하는 공정을 개발하기 위한 연구의 일환으로, 공정 중간체 CHMAIE를 합성하는 실험적 연구를 수행하였다. CHMAIE 제조 공정의 중간체인 CHMA 생성반응은 무수 말레인산 용액에 사이크로헥실아민을 점적 투입한 후 반응액을 2시간 동안 숙성시키는 방법으로 완료하였으며, 생성된 CHMA를 10 ℃ 이하에서 2.5시간 동안 석출시키면 98.2%의 수율을 얻을 수 있었다. CHMA로부터 CHMAIE를 제조하는 에스테르화 반응의 최적 온도는 68 ℃ 이었으며, 이 최적 온도에서의 평형 전화율은 98.5%였다. 에스테르화 반응이 평형에 도달하는 시간은 온도에 따라 감소하며, 최적 온도에서의 평형도달 시간은 약 3시간 정도였다. 최종 생성물 중의 톨루엔은 진공 증류를 통하여 회수할 수 있었다. 톨루엔의 회수율은 증류 온도가 증가함에 따라 증가하였고, 증류 온도 55 ℃에서의 톨루엔 회수율은 98%였다.
For the purpose of development of effective synthetic process of CHMI, a series of experiments were preformed on the preparation of CHMAIE, the intermediate of CHMI. For the first step, CHMA was synthesized by dropwise mixing of cyclohexylamine with maleic anhydride in toluene and 98.2% of theoretical CHMA was obtained by precipitation at 10 ℃ for 2 hours. The optimum reaction temperature of the esterfication, preparation reaction of CHAMIE from CHMA, was 68 ℃, and equilibrium conversion at optimum temperature was 98.5%. Equilibrium reaction time decreased with reaction temperature, and 4 hours was taken to reach equilibrium at optimum reaction temperature. Toluene in the final reaction product could be recovered by vacuum distillation. The recovery of toluene was increased with distillation temperature and 98% of toluene could be recovered at 55 ℃.
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References
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