Journal of the Korean Industrial and Engineering Chemistry, Vol.7, No.1, 171-176, February, 1996
N-alkyl-N-acyl glucamines의 합성에 관한 연구
Studies on the Synthesis of N-alkyl-N-acyl glucamines
초록
환경 친화성인 비이온 계면활성제 글루카마이드(N-알킬-N-아실 글루카민)는 크게 두 단계 반응으로 구분되는데, 첫 단계는 알킬 아민과 글루코스를 메탄올 용매하에 아민화 반응시킨 후, Ni 촉매하에 고압으로 환원시킨 결과 4종의 알킬 글루카민을 86∼93%의 수율로 얻었다. 2단계 반응에서는 4종의 알킬 글루카민과 4종의 지방산 메틸 에스테르를 알칼리 촉매하에 메탄올을 환류시키면서 합성한 결과 16종중 12종의 글루카마이드는 84∼95%수준의 높은 수율을 보였으나, 알킬기가 벤질일 경우에는 50∼70%의 낮은 수율을 나타내었다. 알킬 글루카민 4종과 글루카마이드 16종에 대한 분자구조 확인은 IR, MS, NMR로 확인하였다.
The easily biodegradable nonionic surfactant of glucamide(N-alkyl-N-acyl glucamine) was synthesized by the two-step reaction. The first step was the amination between alkylamine and glucose in methanol. Then, alkyl glucamines were obtained by reduction using Ni catalyst under the high pressure with 86∼93% of reaction yield. The second step was the synthesis of glucamide from alkyl glucamine and fatty acid methyl ester in methanol under the alkali catalytic condition while refluxing the solvent. The reaction yield of this step was 84∼95% except the benzyl glucamine, which the reaction yield was 50∼70%. The molecular structure of four kinds of alkyl glucamine and 16 kinds of glucamide with different alkyl and acyl groups was studied by IR, MS and NMR.
- Kao Corporation "Surfactants," 1st Edition P1 (1983)
- Yoon YK, Choi KS, "Studies on Physical Behaviors of Alkyl Polyglycosides," (1995)
- Flint RB, Salzberg PL, U.S. Patent, 2,016,962 (1935)
- Flint RB, Salzberg PL, Chem. Abstr., 29, 8007 (1935)
- Karrer P, Herkenrath E, Helv. Chim. Acta, 20, 83 (1937)
- Pfanz H, Handel K, Ger. Patent, 13,746 (1957)
- Pfanz H, Handel K, Chem. Abstr., 53, 11261 (1959)
- Dorn H, Wefle H, Liebig R, Chem. Ber., 99(3), 812 (1966)
- Yakovleva VY, Gorbunova AD, Vishnevskaya GI, Kirienko SS, Yavorskii DF, Yagupolskii LM, Khim. Farm. Zh., 1(3), 51 (1967)
- Yakovleva VY, Gorbunova AD, Vishnevskaya GI, Kirienko SS, Yavorskii DF, Yagupolskii LM, Eng. Trans. Pharm. Chem. J., 1, 164 (1968)
- Mitts E, Hixon RM, J. Am. Chem. Soc., 66, 483 (1944)
- AMadori M, Atti Accad. Nazl. Lincei, 2, 337 (1925)
- AMadori M, Chem. Abstr., 20, 902 (1926)
- AMadori M, Atti Accad. Nazl. Lincei, 9, 226 (1929)
- AMadori M, Chem. Abstr., 23, 3443 (1929)
- AMadori M, Chem. Abstr., 23, 3211 (1929)
- Pigman WW, "The Carbohydrates," p. 422, Academic Press, New York (1957)
- Kunz W, Krausch H, Chemiker-Ztg., 82, 867 (1958)
- Hodge JE, "Advances in Carbohydrate Chemistry," vol. 10, p. 180, Academic Press, New York (1955)
- Rosen L, Woods JW, Pigman WW, Chem. Ber., 90, 1038 (1957)
- Rosen L, Woods JW, Pigman WW, J. Am. Chem. Soc., 80, 4697 (1958)