수중에서 금속 촉매의 니트릴 수화 반응에 의한 환경친화적 아미드 합성

무하마드 아십 후세인; 김정원; Muhammad Asif Hussain; Jung Won Kim

Applied Chemistry for Engineering, Vol.26, No.2, 128-131, April, 2015

Export Citation

수중에서 금속 촉매의 니트릴 수화 반응에 의한 환경친화적 아미드 합성

Environmentally Friendly Synthesis of Amide by Metal-catalyzed Nitrile Hydration in Aqueous Medium

무하마드 아십 후세인, 김정원 ^†

강원대학교 화학공학과

Muhammad Asif Hussain, and Jung Won Kim^†

Department of Chemical Engineering, Kangwon National University, 346 Joongang-ro, Samcheok, Gangwon-do, 245-711, Korea

E-mail:

초록

친환경적 조건에서의 니트릴의 수화 반응은 아미드를 생산하기 위한 가장 경제적이고 매력적인 방법이다. 고체 금속 산화물과 지지체를 이용한 전이 금속 촉매 시스템은 이러한 니트릴 수화 반응을 보다 향상시키기 위한 의미 있는 연구로써 수행되어져 왔다. 이들 촉매들의 중요한 특징은 방향족, 지방족, 이종 원자형, 지방족 고리형 등의 니트릴들을 포함하는 넓은 범위의 다양한 기질들에 적용된다는 것이다. 또한 이들은 높은 촉매적 활성을 유지하면서 여러 번의 재사용성이 가능하고 반응 후 그 혼합물로부터 분리가 용이하다는 장점들을 갖는다. 이 리뷰를 통하여 니트릴 수화 반응을 통한 아미드 합성에 적용되는 금속 산화물과 지지체를 가진 금속 촉매들에 대해 알아본다.

Hydration of nitriles in the environmentally benign neutral conditions is the most economical and attractive way to produce amides. Substantial research works have been carried out to apply the solid metal oxides and transition metal supported catalytic systems to promote the hydration of nitriles. The most significant feature of these catalysts is the applicability to a wide range of substrates including aromatic, alicyclic, hetero-atomic, and aliphatic nitriles. These catalysts are also characterized by the easy isolation from the reaction mixture and the reusability while maintaining the high catalytic activity. This review accounts over the detailed survey of the metal oxide and solid supported metal catalysts for preparing amides from the hydration of nitriles.

Keywords:Hydration;nitrile;metal oxide;supported transition metal;catalyst

[References]

Johansson I, Othmer Encyclopedia of Chemical Technology, JohnWiley & Sons, New York, 442-463 (2004)
Greenberg A, Breneman CM, Liebman JF, The Amide Linkage: Structural Significance in Chemistry, Biochemistry, and Materials Science, John Wiley & Sons (2000)
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Dugger RW, Ragan JA, Ripin DHB, Org. Process Res. Dev., 9, 253 (2005)
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Valeur E, Bradley M, Chem. Soc. Rev., 38, 606 (2009)
Baig RBN, Nadagouda MN, Varma RS, Green Chem., 16, 21 (2014)
Cadierno V, Francos J, Gimeno J, Chemistry, 14, 6601 (2008)
Kumar S, Das P, New J. Chem., 37, 2987 (2013)
Mitsudome T, Mikami Y, Mori H, Arita S, Mizugaki T, Jitsukawa K, Kaneda K, Chem. Commun., 40, 3258 (2009)
Polshettiwar V, Varma RS, Chemistry, 15, 1582 (2009)
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Tamura M, Satsuma A, Shimizu K, Catal. Sci. & Tech., 3, 1386 (2013)
Tamura M, Wakasugi H, Shimizu K, Satsuma A, Chemistry, 17, 11428 (2011)
Tamura M, Tonomura T, Shimizu K, Satsuma A, Appl. Catal. A: Gen., 417, 6 (2012)
Roy SC, Dutta P, Nandy LN, Roy SK, Samuel P, Pillai SM, Kaushik VK, Ravindranathan M, Appl. Catal. A: Gen., 290(1-2), 175 (2005)
Van Dijk AJ, Duchateau R, Hensen EJ, Meuldijk J, Koning CE, Chem. Eur. J., 13, 7673 (2007)
Garcia-Alvarez R, Francos J, Tomas-Mendivil E, Crochet P, Cadierno V, J. Organomet. Chem., 771, 93 (2014)
Mori K, Yamaguchi K, Mizugaki T, Ebitani K, Kaneda K, Chem. Commun., 32, 461 (2001)
Yamaguchi K, Matsushita M, Mizuno N, Angew. Chemi., 116, 1602 (2004)
Prakash GKS, Munoz SB, Papp A, Masood K, Bychinskaya I, Mathew T, Olah GA, Asian J. Org. Chem., 1, 146 (2012)
Woo H, Lee K, Park S, Park KH, Molecules, 19, 699 (2014)
Shimizu K, Imaiida N, Sawabe K, Satsuma A, Appl. Catal. A: Gen., 421, 114 (2012)

[Referenced By]

[Related Articles]

[1] Johansson I, Othmer Encyclopedia of Chemical Technology, JohnWiley & Sons, New York, 442-463 (2004)

[2] Greenberg A, Breneman CM, Liebman JF, The Amide Linkage: Structural Significance in Chemistry, Biochemistry, and Materials Science, John Wiley & Sons (2000)

[3] Carey JS, Laffan D, Thomson C, Williams MT, Org. & Biomol. Chem., 4, 2337 (2006)

[4] Dugger RW, Ragan JA, Ripin DHB, Org. Process Res. Dev., 9, 253 (2005)

[5] Deopura BL, Gupta B, Joshi M, Alagirusami R, Polyesters and Polyamides, CRC Press, Boca Raton (2008)

[6] Garcia-Alvarez R, Crochet P, Cadierno V, Green Chem., 15, 46 (2013)

[7] Constable DJ, Jimenez-Gonzalez C, Henderson RK, Org. Process Res. Dev., 11, 133 (2007)

[8] Kerton FM, Marriott R, Alternative solvents for green chemistry, Royal Society of chemistry

[9] Valeur E, Bradley M, Chem. Soc. Rev., 38, 606 (2009)

[10] Baig RBN, Nadagouda MN, Varma RS, Green Chem., 16, 21 (2014)

[11] Cadierno V, Francos J, Gimeno J, Chemistry, 14, 6601 (2008)

[12] Kumar S, Das P, New J. Chem., 37, 2987 (2013)

[13] Mitsudome T, Mikami Y, Mori H, Arita S, Mizugaki T, Jitsukawa K, Kaneda K, Chem. Commun., 40, 3258 (2009)

[14] Polshettiwar V, Varma RS, Chemistry, 15, 1582 (2009)

[15] Shimizu K, Kubo T, Satsuma A, Kamachi T, Yoshizawa K, ACS Catal., 2, 2467 (2012)

[16] Tamura M, Satsuma A, Shimizu K, Catal. Sci. & Tech., 3, 1386 (2013)

[17] Tamura M, Wakasugi H, Shimizu K, Satsuma A, Chemistry, 17, 11428 (2011)

[18] Tamura M, Tonomura T, Shimizu K, Satsuma A, Appl. Catal. A: Gen., 417, 6 (2012)

[19] Roy SC, Dutta P, Nandy LN, Roy SK, Samuel P, Pillai SM, Kaushik VK, Ravindranathan M, Appl. Catal. A: Gen., 290(1-2), 175 (2005)

[20] Van Dijk AJ, Duchateau R, Hensen EJ, Meuldijk J, Koning CE, Chem. Eur. J., 13, 7673 (2007)

[21] Garcia-Alvarez R, Francos J, Tomas-Mendivil E, Crochet P, Cadierno V, J. Organomet. Chem., 771, 93 (2014)

[22] Mori K, Yamaguchi K, Mizugaki T, Ebitani K, Kaneda K, Chem. Commun., 32, 461 (2001)

[23] Yamaguchi K, Matsushita M, Mizuno N, Angew. Chemi., 116, 1602 (2004)

[24] Prakash GKS, Munoz SB, Papp A, Masood K, Bychinskaya I, Mathew T, Olah GA, Asian J. Org. Chem., 1, 146 (2012)

[25] Woo H, Lee K, Park S, Park KH, Molecules, 19, 699 (2014)

[26] Shimizu K, Imaiida N, Sawabe K, Satsuma A, Appl. Catal. A: Gen., 421, 114 (2012)