연결부에 아민기를 가지는 디에폭사이드 화합물의 효율적인 합성방법

박종목; 김호철; 이병민; 김동표; Jong Mok Park; Hocheol Kim; Byung Min Lee; Dong-Pyo Kim

Journal of the Korean Industrial and Engineering Chemistry, Vol.14, No.2, 249-252, April, 2003

Export Citation

연결부에 아민기를 가지는 디에폭사이드 화합물의 효율적인 합성방법

Efficient Synthetic Method of Diepoxide Compound Containing Amino Group in the Connecting Part

박종목 ^†, 김호철, 이병민, 김동표 ¹

한국화학연구원 유제화학연구센터, 대전 305-600
¹충남대학교 공과대학 정밀공업화학과, 대전 305-764

Jong Mok Park^†, Hocheol Kim, Byung Min Lee, and Dong-Pyo Kim¹

Surfactants & Lubricants Center, Korea Research Institute of Chemical Technology, Daejeon 305-600, Korea
¹Department of Fine Chemical Engineering & Chemistry, Chungnam National University, Daejeon 305-764, Korea

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초록

메틸아민과 에피클로로히드린을 반응시켜 N,N-diglycidyl methyl amine을 합성하였다. 이 반응의 진행과정을 GC분석을 통해 반응 중간체들을 관찰함으로써 연구하였다. 연결기로 아민을 사용하여 디에폭사이드 화합물을 합성하는 경우에 있어서는 연결기로 디올을 사용하는 경우에 잘 알려진 1단계 반응(반응초기에 염기를 투입, 분석수율: 36.2 %)에 비해서 2단계 반응(염기가 없는 상태에서 반응 후 염기를 투입, 분석수율: 91.5 %)이 훨씬 효율적이었다.

N,N-Diglycidyl methyl amine was prepared by reacting methyl amine with epichlorohydrin. The process of the reaction was studied by analyzing intermediates using GC. In the case of preparation of diepoxide compounds using amines as a connecting group, two-step reaction (base was added when the reaction in the absence of base was stopped, yield: 91.5 %) was much more efficient than one-step reaction (base was added at the beginning of the reaction, yield: 36.2 %) which has been well-known in the case of using diols as a connecting group.

Keywords:diepoxide compound;methyl amne;epichlorohydrin;N,N-Diglycidyl methyl amine

[References]

Maeda H, Kikui T, Nakatsuji Y, Okahara M, J. Org. Chem., 51, 81 (1986)
Yokota K, Hashimoto H, Kakuchi T, Kataka Y, Makromol. Chem. Rapid Commun., 5, 115 (1984)
Okahara M, Masuyama A, Sumida Y, Zhu YP, J. Jpn. Oil Chem Soc., 37, 746 (1988)
Zhu YP, Masuyama A, Okahara M, JAOCS, 67, 459 (1990)
Akopyan LA, Avetyan MG, Matsoyan SG, Izv. Akad. Nauk Arm. SSR, Khim. Nauki, 17, 703 (1964)
Blyakhman EM, Zh. Org. Khim., 3, 1423 (1967)
Gu XP, Ikeda I, Okahara M, Synthesis, 649 (1984)
Kang HC, Lee BM, Yoon J, Yoon M, JAOCS, 78, 423 (2000)

[Referenced By]

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[1] Maeda H, Kikui T, Nakatsuji Y, Okahara M, J. Org. Chem., 51, 81 (1986)

[2] Yokota K, Hashimoto H, Kakuchi T, Kataka Y, Makromol. Chem. Rapid Commun., 5, 115 (1984)

[3] Okahara M, Masuyama A, Sumida Y, Zhu YP, J. Jpn. Oil Chem Soc., 37, 746 (1988)

[4] Zhu YP, Masuyama A, Okahara M, JAOCS, 67, 459 (1990)

[5] Akopyan LA, Avetyan MG, Matsoyan SG, Izv. Akad. Nauk Arm. SSR, Khim. Nauki, 17, 703 (1964)

[6] Blyakhman EM, Zh. Org. Khim., 3, 1423 (1967)

[7] Gu XP, Ikeda I, Okahara M, Synthesis, 649 (1984)

[8] Kang HC, Lee BM, Yoon J, Yoon M, JAOCS, 78, 423 (2000)