화학공학소재연구정보센터
Journal of the Korean Industrial and Engineering Chemistry, Vol.12, No.2, 224-228, April, 2001
1,3,3-Trinitroazetidine(TNAZ)의 중간체 합성에 대한 연구
A Study on the Synthesis of a Key Intermediate for TNAZ
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초록
TNAZ는 azetidine 고리를 가지며 한 개의 니트로아민과 gem-dinitro 기를 포함하고 있어서 폭발력이 강한 물질이다. t-BuNH2과 epichlorohydrin의 반응으로 1-t-butyl-3-hydroxyazetidine·HCl를 얻었다. 톨루엔을 용매로 사용할 때 산 촉매가 반응시간을 단축시킨다. 이 반응의 중간체인 amino alcohol 1을 분리했으며 용매량, 온도, 반응시간을 변화시켜 amino alcohol 1의 형성반응을 연구했다. TNAZ 합성의 중요한 중간체인 1-t-butyl-3-nitroazetidine 대신 1-t-butyl-3-hydroxylmethyl-3-nitro-azetidine을 1-t-butyl-3-hydroxyazetidine·HCl로부터 합성하였다. 전체적인 수율은 기존 방법과 비슷한데 반응 후 처리가 용이했다.
TNAZ is a high explosive material that possesses a azetidine ring, which contains one nitramine and geminal dinitro groups. t-Butylamine was reacted with epichlorohydrin to give 1-t-butyl-3-hydroxyazetidine·HCl. When toluene was used as a solvent, and acid catalyst was necessary to reduce the reaction time. In addition, the reaction intermediate, amino alcohol 1, was isolated and the intermediate reaction was studied by varying the amount of solvent, temperature, and reaction time. Instead of 1-t-butyl-3-nitroazetidine, as the key intermediate for TNAZ, 1-t-butyl-3-hydroxymethyl-3-nitroazetidine was prepared from 1-t-butyl -3-hydroxyazetidine·HCl. The yield was comparable, but the work-up was easier than that of the known method.
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