Efficient and Selective Hydrogenation of Carboxylic Acid Catalyzed by Ni or Pd on ZSM-5

Donghwan Lee; Sung Il Cho; Geon-Joong Kim; Honggon Kim; Ik-Mo Lee

Journal of Industrial and Engineering Chemistry, Vol.13, No.7, 1067-1075, December, 2007

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Efficient and Selective Hydrogenation of Carboxylic Acid Catalyzed by Ni or Pd on ZSM-5

Donghwan Lee, Sung Il Cho¹, Geon-Joong Kim¹, Honggon Kim², and Ik-Mo Lee^†

Department of Chemistry, Inha Univeristy, Incheon 402-751, Korea
¹Department of Chemical Engineering, Inha University, Incheon 402-751, Korea
²Reaction Media Research Center, Environment & Process Technology Division, Korea Institute of Science and Technology, Seoul 136-791, Korea

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Efficient and selective catalytic systems, where Ni or Pd is introduced on the silicate material (ZSM-5) having micropore and mesopore structures, have been developed for the reduction of carboxylic acids with H2 at room temperature. It is found that the catalytic activity depends on the hydrogen pressure, the agitation rate, the nature and the amount of active species. A plausible reaction mechanism for the hydrogenation of carboxylic acids to corresponding alcohols is proposed on the basis of electronic and steric effects in these reactions.

Keywords:Ni;Pd;carboxylic acid;alcohol;ZSM.5;hydrogenation;mechanism

[References]

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Cho SD, Park YD, Kim JJ, Falck JR, Yoon YJ, Bull. Korean Chem. Soc., 407-409 and references therein, 25 (2004)
Paquette LA, in Encyclopedia of Reagents for Organic Synthesis, vol 7, pp. 4522-4528 John Wiley & Sons Inc.: New York (1995)
Ohta T, Kamiya M, Nobutomo M, Kusui K, Furukawa KI, Bull. Chem. Soc. Jpn., 78, 1856 (2005)
Thomas JM, Angew. Chem.-Int. Edit., 38, 3588 (1999)
Feng M, Puddephatt RJ, Chem. Mater., 2696-2698 and references therein, 15 (2003)
Heck RM, Farrauto RJ, in Catalytic Air Pollution Control, Commercial Technology, pp. 71-112, Van Nostrand Reinhold: New York (1995)
Kim SW, Kim M, Lee WY, Hyeon T, J. Am. Chem. Soc., 124(26), 7642 (2002)
Moreno-Manas M, Pleixats M, Accounts Chem. Res., 36, 638 (2003)
Ying JY, AIChE J., 46(10), 1902 (2000)
Zhao DY, Feng JL, Huo QS, Melosh N, Fredrickson GH, Chmelka BF, Stucky GD, Science, 279(5350), 548 (1998)
Hue QS, Margolese DI, Ciesla U, Feng PY, Gier TE, Sieger P, Leon R, Petroff PM, Schuth F, Stucky GD, Nature, 368(6469), 317 (1994)
Schacht S, Huo Q, Voigtmartin IG, Stucky GD, Schuth F, Science, 273(5276), 768 (1996)
Kim SS, Pauly TR, Pinnaviaia TJ, Chem. Commun., 835 (2000)
Yang PD, Zhao DY, Margolese DI, Chmelka BF, Stucky GD, Nature, 396(6707), 152 (1998)
Antonelli DM, Ying JY, Angew. Chem.-Int. Ed. Engl., 35, 426 (1996)
Sun T, Ying JY, Nature, 389(6652), 704 (1997)
Corma A, Chem. Rev., 97(6), 2373 (1997)
Ying JY, Mehnert CP, Wong MS, Angew. Chem.-Int. Ed. Engl., 35, 426 (1996)
Liu Y, Zhang W, Pinnavaia TJ, Angew. Chem.-Int. Ed. Engl., 40, 1255 (2001)
Kloeststra KR, Zandbergen HW, Jansen JC, van Bekkum H, Microporous Mater., 6, 287 (1996)
Karlsson A, Stocker M, Schmidt R, Microporous Mesoporous Mater., 27, 181 (1999)
Karlsson, Stocker M, Schaefer K, Stud. Surf. Sci. Catal., 125, 61 (1999)
Kwon YK, Kim DH, Kim GJ, Han YS, Seong BS, Stud. Surf. Sci. Catal., 146, 355 (2003)
Kwon YK, Kim GJ, Lim JH, Kim DH, Choi BD, Stud. Surf. Sci. Catal., 146, 141 (2003)
Cho SI, Kwon YK, Park SE, Kim GJ, Stud. Surf. Sci. Catal., 146, 137 (2003)
Jacobsen CJH, Madsen C, Houzvicka J, Schmidt I, Carlsson A, J. Am. Chem. Soc., 122(29), 7116 (2000)
Cho SI, Choi SD, Kim JH, Kim GJ, Adv. Funct. Mater., 14(1), 49 (2004)
Johnson SA, Brigham ES, Oliver PJ, Mallouk TE, Chem. Mater., 9, 2448 (1997)
Lee JW, Yoon S, Hyeon T, Oh SM, Kim KB, Chem. Commun., 2177 (1999)
Clapham SE, Hadzovic A, Morris RH, Coord. Chem. Rev., 248, 2201 (2004)
Neyestanaki AK, Maki-Arvela P, Backman H, Karhu H, Salmi T, Vayrynen J, Murzin DY, J. Catal., 218(2), 267 (2003)
Vitulli G, Evangelisti C, Pertici P, Caporusso AM, Panziera N, Salvadori P, Faga MG, Manfredotti C, Martra G, Coluccia S, Balerna A, Colonna, and S. Mobilio S, J. Org. Chem., 681, 37 (2003)
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Park SY, Kang M, Yie JE, Kim JM, Lee IM, Tetrahedron Lett., 46, 2849 (2005)
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Hansch C, Leo A, Taft RW, Chem. Rev., 91, 165 (1991)
Crabtree RH, The Organometallic Chemistry of the Transition Metals, 4th ed., p76, John Wiley & Sons, Inc., New Jersey (2005)

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[2] Cho SD, Park YD, Kim JJ, Falck JR, Yoon YJ, Bull. Korean Chem. Soc., 407-409 and references therein, 25 (2004)

[3] Paquette LA, in Encyclopedia of Reagents for Organic Synthesis, vol 7, pp. 4522-4528 John Wiley & Sons Inc.: New York (1995)

[4] Ohta T, Kamiya M, Nobutomo M, Kusui K, Furukawa KI, Bull. Chem. Soc. Jpn., 78, 1856 (2005)

[5] Thomas JM, Angew. Chem.-Int. Edit., 38, 3588 (1999)

[6] Feng M, Puddephatt RJ, Chem. Mater., 2696-2698 and references therein, 15 (2003)

[7] Heck RM, Farrauto RJ, in Catalytic Air Pollution Control, Commercial Technology, pp. 71-112, Van Nostrand Reinhold: New York (1995)

[8] Kim SW, Kim M, Lee WY, Hyeon T, J. Am. Chem. Soc., 124(26), 7642 (2002)

[9] Moreno-Manas M, Pleixats M, Accounts Chem. Res., 36, 638 (2003)

[10] Ying JY, AIChE J., 46(10), 1902 (2000)

[11] Zhao DY, Feng JL, Huo QS, Melosh N, Fredrickson GH, Chmelka BF, Stucky GD, Science, 279(5350), 548 (1998)

[12] Hue QS, Margolese DI, Ciesla U, Feng PY, Gier TE, Sieger P, Leon R, Petroff PM, Schuth F, Stucky GD, Nature, 368(6469), 317 (1994)

[13] Schacht S, Huo Q, Voigtmartin IG, Stucky GD, Schuth F, Science, 273(5276), 768 (1996)

[14] Kim SS, Pauly TR, Pinnaviaia TJ, Chem. Commun., 835 (2000)

[15] Yang PD, Zhao DY, Margolese DI, Chmelka BF, Stucky GD, Nature, 396(6707), 152 (1998)

[16] Antonelli DM, Ying JY, Angew. Chem.-Int. Ed. Engl., 35, 426 (1996)

[17] Sun T, Ying JY, Nature, 389(6652), 704 (1997)

[18] Corma A, Chem. Rev., 97(6), 2373 (1997)

[19] Ying JY, Mehnert CP, Wong MS, Angew. Chem.-Int. Ed. Engl., 35, 426 (1996)

[20] Liu Y, Zhang W, Pinnavaia TJ, Angew. Chem.-Int. Ed. Engl., 40, 1255 (2001)

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[22] Karlsson A, Stocker M, Schmidt R, Microporous Mesoporous Mater., 27, 181 (1999)

[23] Karlsson, Stocker M, Schaefer K, Stud. Surf. Sci. Catal., 125, 61 (1999)

[24] Kwon YK, Kim DH, Kim GJ, Han YS, Seong BS, Stud. Surf. Sci. Catal., 146, 355 (2003)

[25] Kwon YK, Kim GJ, Lim JH, Kim DH, Choi BD, Stud. Surf. Sci. Catal., 146, 141 (2003)

[26] Cho SI, Kwon YK, Park SE, Kim GJ, Stud. Surf. Sci. Catal., 146, 137 (2003)

[27] Jacobsen CJH, Madsen C, Houzvicka J, Schmidt I, Carlsson A, J. Am. Chem. Soc., 122(29), 7116 (2000)

[28] Cho SI, Choi SD, Kim JH, Kim GJ, Adv. Funct. Mater., 14(1), 49 (2004)

[29] Johnson SA, Brigham ES, Oliver PJ, Mallouk TE, Chem. Mater., 9, 2448 (1997)

[30] Lee JW, Yoon S, Hyeon T, Oh SM, Kim KB, Chem. Commun., 2177 (1999)

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[40] Crabtree RH, The Organometallic Chemistry of the Transition Metals, 4th ed., p76, John Wiley & Sons, Inc., New Jersey (2005)