Utlenianie limonenu tlenem cząsteczkowym i nadtlenkiem wodoru

Szczepanik, A.; Sobkowiak, A.

Artykuł - szczegóły

Tytuł artykułu

Utlenianie limonenu tlenem cząsteczkowym i nadtlenkiem wodoru

Autorzy

Szczepanik A. , Sobkowiak A.

Wybrane pełne teksty z tego czasopisma

Identyfikatory

Warianty tytułu

Oxidation of limonene with dioxygen and hydrogen peroxide

Języki publikacji

Abstrakty

Limonene is one of the most abundant and readily available terpenes [5-7, 9-15]. It constitutes approximately 90% of orange and grapefruit peel oil [5] and hence it is potentially available in large amounts as a by-product of the citrus industry [21]. In contrast to relatively inexpensive limonene, products of its oxidation, such as: ?-terpineol, carveol, carvone, perillyl alcohol, menthol and limonene oxide, are compounds of a very high market value [16] and they are widely used (apart from the epoxide) in the flavor and fragrance industry [7]. Limonene oxide can be applied as a building block in the synthesis of drugs [18, 19] and biodegradable polymers [20]. Since an industrial method of limonene conversion into its ketone - carvone (used as a mint flavor for foods and oral hygiene products [7]) - involves several stages and the use of environmentally hazardous chemicals [21], it does not remain in accordance with 'green chemistry'. The latter problem concerns also the methods of limonene oxidation based on chromium(VI) compounds [25-28]. Hence a lot of attention is paid to limonene oxidation using environmentally benign oxidants, namely dioxygen and hydrogen peroxide. Literature studies revealed that a variety of approaches to limonene oxidation by oxygen and hydrogen peroxide had been published so far. The oxidation of limonene using dioxygen can be performed catalytically and photochemically [80-86]. Generally, a complex mixture of limonene oxidated derivatives is obtained using Wacker-like systems [44-51] as well as all sorts of cobalt catalysts [52-56]. Transition metal complexes can also activate dioxygen for the oxidation of limonene giving a mixture of products [78, 79]. Limonene epoxides are usually produced by Mukaiyama systems, where peracid is in-situ generated from oxygen, aldehyde and transition metal complex [59-77]. The oxidation of limonene by hydrogen peroxide usually leads to its epoxidation [90-98, 100, 101]; however, sometimes other limonene derivatives are formed [99, 134-136]. Limonene oxidation using hydrogen peroxide proceeds in the presence of catalysts which are transition metal complexes [90-105], heteropolyanions [109-120], aluminum oxide [121-125] as well as titanium-containing catalysts [126-131]. Furthermore, hydrogen peroxide reacts with nitriles forming peroxycarboximidic acid which can epoxidize limonene in Payne reaction [132, 133].

Słowa kluczowe

limonen utlenianie tlen cząsteczkowy nadtlenek wodoru

limonene oxidation dioxygen hydrogen peroxide

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

2009

Tom

[Z] 63, 7-8

Strony

601--634

Opis fizyczny

bibliogr. 138 poz., wykr.

Twórcy

autor

Szczepanik A.

autor

Sobkowiak A.

Grace Sp. z o.o., ul. Rubież 46, 61-612 Poznań, Anna.Szczepanik@grace.com

Bibliografia

[1] A. Kołodziejczyk, [w:] Naturalne związki organiczne, Wydawnictwo Naukowe PWN, Warszawa 2003.
[2] M. Eggersdorfer, [w:] Ullman's Encyclopedia of Industrial Chemistry, Sixth Edition, 2002 Electronic Release, Wiley-VCH, Weinheim, Germany.
[3] Polskie Towarzystwo Chemiczne, Nomenklatura związk organicznych, Państwowe Wydawnictwo Naukowe, Warszawa 1992.
[4] I. Fichan, C. Larroche, J.B. Gros, J. Chem. Eng. Data, 1999, 44, 56.
[5] K.P. Swoboda, R.I. Greenaway, Int. J. Aromather., 2003, 13, 23.
[6] F.B. Power, Ind. Eng. Chem., 1919, 11, 344.
[7] K. Bauer, D. Garbe, H. Surburg, [w:] Ullman's Encyclopedia of Industrial Chemistry, Sixth Edition, 2002 Electronic Release, Wiley-VCH, Weinheim, Germany.
[8] J. Wright, [w:] Food Flavorings, Third Edition, Aspen Publishers, Inc., Gaithersburg, Maryland 1999.
[9] M. Gscheidmeier, H. Fleig, [w:] Ullman's Encyclopedia of Industrial Chemistry, Sixth Edition, 2002 Electronic Release, Wiley-VCH, Weinheim, Germany.
[10] R. Bogoczek, E. Kociałek-Blawejder, [w:] Technologia chemiczna organiczna, Surowce i półprodukty, Wydawnictwo Akademii Ekonomicznej we Wrocławiu, Wrocław 1992.
[11] H. Pakdel, C. Roy, H. Aubin, G. Jean, S. Coulombe, Environ. Sci. Technol. 1991, 25, 1646.
[12] H. Pakdel, D.M. Pantea, C. Roy, J. Anal. Appl. Pyrolysis, 2001, 57, 91.
[13] A. Stolle, C. Brauns, M. Nüchter, B. Ondruschka, W. Bonrath, M. Findeisen, Eur. J. Org. Chem., 2006, 3317.
[14] C.M. López, F.J. Machado, K. Rodriguez, D. Arias, N. Méndez, M.Hasegawa, Catal. Lett., 1999, 62, 221.
[15] R. Laque, J.M. Campelo, T.D. Conesa, D. Luna, J.M. Marinas, A.A. Romero, Microporous Mesoporous Mater., 2007, 103, 333.
[16] W.A. Duetz, H. Bouwmeester, J.B. van Beilen, B. Witholt, Appl. Microbiol. Biotechnol. 2003, 61, 269.
[17] H. Fiege, [w:] Ullman's Encyclopedia of Industrial Chemistry, Sixth Edition, 2002 Electronic Release, Wiley-VCH, Weinheim, Germany.
[18] Y. Li, T. Zhang, Y.-L. Li, Tetrahedron Lett., 2007, 48, 1503.
[19] R. Rodriguez, C. Ollivier, M. Santelli, Tetrahedron Lett., 2004, 45, 2289.
[20] C.M. Byrne, S.D. Allen, E.B. Lobkovsky, G.W. Coates, J. Am. Chem. Soc., 2004, 126, 11404.
[21] C. Bordenca, R.K. Allison, P.H. Dirstine, Ind. Eng. Chem., 1951, 43, 1196.
[22] E.E. Royals, S.E. Jr. Horne, J. Am. Chem. Soc., 1951, 73, 5856.
[23] R.H. Reitsema, J. Org. Chem., 1958, 23, 2038.
[24] H.J. Bouwmeester, J.A.R. Davies, H. Toxopeus, J. Agric. Food Chem., 1995, 43, 3057.
[25] S.M. Linder, F. Greenspan, J. Org. Chem., 1956, 22, 949.
[26] W.G. Dauben, M. Lorben, D.S. Fullerton, J. Org. Chem., 1969, 34, 3587.
[27] C.W. Wilson, P.E. Shaw, J. Agric. Food Chem., 1975, 23, 636.
[28] L.H.B. Baptistella, I.M.O. Sousa, Y. Gushikem, A.M. Alexio, Tetrahedron Lett., 1999, 40, 2695.
[29] H.E. Eschinazi, E.D. Bergmann, J. Am. Chem. Soc., 1950, 72, 5651.
[30] R.C. Palmer, Ind. Eng. Chem., 1942, 34, 1028.
[31] P. Lesage, J.P. Candy, C. Hirigoyen, F. Humbolt, J.M. Basset, J. Mol. Catal. A: Chem., 1996, 112, 431.
[32] D. Buhl, D.M. Roberge, W.F. Hölderich, Appl. Catal., A, 1999, 188, 287.
[33] P.A. Weyrich, W.F. Hölderich, Appl. Catal., A, 1997, 158, 145.
[34] S.A. Mahood, Ind. Eng. Chem., 1920, 12, 1152.
[35] B.L. Davis, L.A. Goldblatt, S. Palkin, Ind. Eng. Chem., 1946, 38, 53.
[36] G. Collin, R. Mildenberg, M. Zander, M. Höke, W. McKillip, W. Freitag, W. Imöhol, [w:] Ullman's Encyclopedia of Industrial Chemistry, Sixth Edition, 2002 Electronic Release, Wiley-VCH, Weinheim, Germany.
[37] D. Stoye, [w:] Ullman's Encyclopedia of Industrial Chemistry, Sixth Edition, 2002 Electronic Release, Wiley-VCH, Weinheim, Germany.
[38] J. Durkee, Met. Finish., 2008, 106, 40.
[39] G.W. Bohnert, R.D. Carter, T.E. Hand, M.T. Powers, Pat. U.S.A. 5 514 294 (1996).
[40] D.M. Willard, G. Barraza, J.D. Zook, Pat. U.S.A. 6 884 763 (2005).
[41] S.F. van Vuuren, A.M. Viljoen, Flavour. Fragr. J., 2007, 22, 540.
[42] J.S. Jr.Wilkins, Pat. U.S.A. 5 951 992 (1999).
[43] L.U. Franklin, Pat. U.S.A. 5 977 186 (1999).
[44] A.D. Silva, M.L. Patitucci, H.R. Bizzo, E. D'Elia, O.A.C. Antunes, Catal. Commun., 2002, 3, 435.
[45] E. Gusevskaya, J.A. Gonsalves, J. Mol. Catal. A: Chem., 1997, 121, 131.
[46] L. El Firdoussi, A. Baqqa, S. Allaoud, B.A. Allal, A. Karim, Y. Castanet, A. Mortreux, J. Mol. Catal. A: Chem., 1998, 135, 11.
[47] J.A. Gonçalves, E.V. Gusevskaya, Appl. Catal., A 2004, 258, 93.
[48] J.A. Gonçalves, A.C. Bueno, E.V. Gusevskaya, J. Mol. Catal. A: Chem., 2006, 252, 5.
[49] B. Arizaga, A. de Leon, N. Burgueno, A. Lopez, D. Paz, N. Martinez, D. Lorenzo, E. Dellacasa, J. Bussi, J. Chem. Technol. Biotechnol., 2007, 82, 532.
[50] J. Bussi, A. Lopez, F. Pena, P. Timbal, D. Paz, D. Lorenzo, E. Dellacasa, Appl. Catal., A, 2003, 253, 177.
[51] P.A. Robles-Dutenhefner, D.L. Nunes, J.A. Gonçalves, E.V. Gusevskaya, E.M.B. Sousa, J. Non-Cryst. Solids, 2004, 348, 195.
[52] M.F.T. Gomes, O.A.C. Antunes, J. Mol. Catal. A: Chem., 1997, 121, 145.
[53] M.J. da Silva, P. Robles-Dutenhefner, L. Menini, E.V. Gusevskaya, J. Mol. Catal. A: Chem., 2003, 201, 71.
[54] P.A. Robles-Dutenhefner, M.J. da Silva, L.S. Sales, E.M.B. Sousa, E.V. Gusevskaya, J. Mol. Catal. A: Chem., 2004, 217, 139.
[55] L. Menini, M.C. Pereira, L.A. Parreira, J.D. Fabris, E.V. Gusevskaya, J. Catal., 2008, 254, 355.
[56] N.K. Kala Raj, V.G. Puranik, C. Gopinathan, A.V. Ramaswamy, Appl. Catal., A 2003, 256, 265.
[57] P. Mastrorilla, C.F. Nobile, G.P. Sutanna, L. Lopez, Tetrahedron, 1995, 51, 7943.
[58] Corain B., Tessari A., Zecca M., J. Mol. Catal. A: Chem., 1995, 96, L9.
[59] B.B. Wentzel, P.L. Alsters, M.C. Feiters, R.J.M. Nolte, J. Org. Chem., 2004, 69, 3454.
[60] N. Fil, A. Romane, S. Allaoud, A. Karim, Y. Castanet, A. Mortreux, J. Mol. Catal. A: Chem., 1996, 108, 15.
[61] B.B. Wentzel, S.M. Leinonen, S. Thomson, D.C. Sherrington, M.C. Feiters, R.J.M. Nolte, J. Chem. Soc., Perkin Trans., 2000, 1, 3428.
[62] M.M. Reddy, T. Punniyamurthy, J. Iqbal, Tetrahedron Lett., 1995, 36, 159.
[63] T. Punniyamurthy, B. Bahtia, M.M. Reddy, G.C. Maikap, J. Iqbal, Tetrahedron Lett., 1997, 53, 1997.
[64] A.K. Mandal, V. Khanna, J. Iqbal, Tetrahedron Lett., 1996, 37, 3769.
[65] A.K. Mandal, J. Iqbal, Tetrahedron Lett., 1997, 53, 7641.
[66] R. Raja, G. Sankar, J.M. Thomas, Chem. Commun., 1999, 829.
[67] K.S. Ravikumar, F. Barbier, J.P. Bégué, D. Bonet-Delpon, Tetrahedron, 1998, 54, 7457.
[68] P. Leduc, P. Battioni, J.F. Bartoli, D. Mansuy, Tetrahedron Lett., 1988, 29, 205.
[69] X.T. Zhou, H.B. Ji, J.C. Xu, L.X. Pei, L.F. Wang, X.D. Yao, Tetrahedron Lett., 2007, 48, 2691.
[70] L. Saikia, D. Srinivas, P. Ratnasamy, Appl. Catal., A, 2006, 309, 144.
[71] L. Saikia, D. Srinivas, P. Ratnasamy, Microporous Mesoporous Mater., 2007, 104, 225.
[72] D. Srinivas, P. Ratnasamy, Microporous Mesoporous Mater., 2007, 105, 170.
[73] S. Bhattacharjee, J A. Anderson, Catal. Lett., 2004, 95, 119.
[74] S. Bhattacharjee, T.J. Dines, J.A. Anderson, J. Catal., 2004, 225, 398.
[75] S. Bhattacharjee, J A. Anderson, Chem. Commun., 2004, 544.
[76] C. Heinrichs, W.F. Hölderich, Catal. Lett., 1999, 58, 75.
[77] C. Schuster, W.F. Hölderich, Catal. Today, 2000, 60, 193.
[78] D. Naróg, A. Szczepanik, A. Sobkowiak, Catal. Lett., 2008, 120, 320.
[79] A. Szczepanik, A. Sobkowiak, Catal. Lett., 2008, 126, 261.
[80] F. Chiron, J.C.Chalchat, R.P. Garry, J.F. Pilichowski, J. Lacoste, J. Photochem. Photobiol. A Chem., 1997, 111, 75.
[81] J. Shailaja, J. Sivaguru, R.J. Robbins, V. Ramamurthy, R.B. Sunoj, J. Chandrasekhar, Tetrahedron, 2000, 56, 6927.
[82] H. Tokuyama, E. Nakamura, J. Org. Chem., 1994, 59, 1135.
[83] A.G. Griesbeck, M. Cho, Org. Lett., 2007, 9, 611.
[84] M. Trytek, J. Fiedurek, K. Polska, S. Radzki, Catal. Lett., 2005, 105, 119.
[85] M. Trytek, J. Fiedurek, K. Polska, S. Radzki, Biotechnol. Prog., 2007, 23, 131.
[86] J. Fiedurek, M. Trytek, S. Radzki, Pat. PL 371 574 (2004).
[87] C.W. Jones, [w:] Applications of Hydrogen Peroxide and Derivatives, The Royal Society of Chemistry, Cambridge 1999.
[88] B.F. Sels, A.L. Villa, D. Hoegaerts, D.E. De Vos, P.A. Jacobs, Top. Catal., 2000, 13, 223.
[89] L.R. Guilherme, S.M. Drechsel, F. Tavares, C. J. da Cucha, S.T.Castaman, S. Nakagaki, I. Vencato, A.J. Bortoluzzi, J. Catal. Mol. A: Chem., 2007, 269, 22.
[90] M. Louloudi, C. Kolokytha, N. Hadjiliadis, J. Catal. Mol. A: Chem., 2002, 180, 19.
[91] D. Zois, C. Vartzouma, Y. Deligiannakis, N. Hadjiliadis, L. Casella, E. Mozani, M. Louloudi, J. Mol. Catal. A: Chem., 2007, 261, 306.
[92] C. Vartzouma, E. Evaggellou, Y. Sanakis, N. Hadjiliadis, M. Louloudi, J. Mol. Catal. A: Chem., 2007, 263, 77.
[93] A. Serafimidou, A. Satamatis, M. Louloudi, Catal. Commun., 2008, 9, 35.
[94] D. Gournis, M. Louloudi, M.A. Karakassides, C. Kolokytha, K. Mitopoulou, N. Hadjiliadis, Mat. Sci. Eng., C 2002, 22, 113.
[95] L.D. Pinto, J. Dupont, R.F. de Souza, K. Bernardo-Gusmao, Catal. Commun., 2008, 9, 135.
[96] P. Battioni, J.P. Renaud, J.F. Bartoli, M. Reina-Artiles, M. Fort, D. Mansuy, J. Am. Chem. Soc., 1988, 110, 8462.
[97] S. Borocci, F. Marotti, G. Mancini, D. Monti, A. Pastorini, Langmuir, 2001, 17, 7198.
[98] F.C. Skrobot, A.A. Valente, G. Neves, I. Rosa, J. Rocha, J.A.S. Cavaleiro, J. Mol. Catal. A: Chem., 2003, 201, 211.
[99] M. Caovilla, A. Caovilla, S.B.C. Perher, M.C. Esmelindro, C. Fernandes, C. Dariva, K. Bernardo-Gusmao, E.O. Oestreicher, O.A.C. Antunes, Catal. Today, 2008, 133-135, 695.
[100] D. Mandelli, K.B. Voitiski, U. Schuchardt, G.B. Shul'pin, Chem. Nat. Comp., 2002, 38, 243.
[101] K.B.Voitiski, Y.N. Kozlov, D. Mandelli, G.V. Nizova, U. Schuchardt, G.B. Shul'pin, J. Mol. Catal. A: Chem., 2004, 222, 103.
[102] T.R. Boehlow, C.D. Spilling, Tetrahedron Lett., 1996, 37, 2717.
[103] A.L. Villa, D.E. De Vos, C. Montes de C., P.A. Jacobs, Tetrahedron Lett., 1998, 39, 8521.
[104] R. Saladino, V. Neri, A.R. Pelliccia, E. Mincione, Tetrahedron, 2003, 59, 7403.
[105] R. Saladino, A. Andreoni, V. Neri, C. Crestini, Tetrahedron, 2005, 61, 1069.
[106] A.F. Wells, [w:] Strukturalna Chemia Nieorganiczna, Wydawnictwa Naukowo-Techniczne, Warszawa 1993.
[107] N. Mizuno, M. Makoto, Chem. Rev., 1998, 98, 199.
[108] I.V. Kozhevnikov, Chem. Rev., 1998, 98, 171.
[109] M. Bösing, A. Nöh, I. Loose, B. Krebs, J. Am. Chem. Soc., 1998, 120, 7252.
[110] S. Casuscelli, E. Herrero, M. Crivello, C. Pérez, M.G. Equsquiza, C.I. Cabello, I.L. Botto, Catal. Today, 2005, 107-108, 230.
[111] N. Mizuno, S. Hikichi, K. Yamaguchi, S. Uchida, Y. Nakagawa, K. Lehara, K. Kamata, Catal. Today, 2006, 117, 32.
[112] N. Mizuno, Y. Nakagawa, K. Yamaguchi, J. Mol. Catal. A: Chem., 2006, 251, 286.
[113] S.G. Casuscelli, M.E. Crivello, C.F. Perez, G. Ghione, E.R. Herrero, L.R. Pizzio, P.G. Vázques, C.V. Cáceres, M.N. Blanco, Appl. Catal., A, 2004, 274, 115.
[114] L. Salles, C. Aubry, R. Thouvenot, F. Robert, C. Dorémieux-Morin, G. Chottard, H. Ledon, Y. Jeannin, J.-M. Brégeault, Inorg. Chem., 1994, 33, 871.
[115] Y. Mahha, L. Salles, J.-Y. Piquemal, E. Briot, A. Atlamsani, J.-M. Brégeault, J. Catal., 2007, 249, 338.
[116] S. Sakaguchi, Y. Nishiyama, Y. Ishii, J. Org. Chem., 1996, 61, 5307.
[117] J.-Y. Piquemal, L. Salles, G. Chottard, P. Herson, C. Ahcine, J.-M. Brégeault, Eur. J. Inorg. Chem., 2006, 939.
[118] A.L. Villa de P., B.F. Sels, D.E. De Vos, P. Jacobs, J. Org. Chem., 1999, 64, 7267.
[119] A.L. Villa de P., F. Taborda, C. Montes de Correra, J. Mol. Catal. A: Chem., 2002, 185, 269.
[120] T. Kovalchuk, H. Sfihi, V. Zaitsev, J. Fraissard, J. Catal. 2007, 249, 1.
[121] D. Mandelli, M.C.A. van Vliet, R.A. Sheldon, U. Schuchardt, Appl. Catal., A, 2001, 219, 209.
[122] M.C.A. van Vliet, D. Mandelli, I.W.C.E. Arends, U. Schuchardt, R.A. Sheldon, Green Chem., 2001, 3, 243.
[123] R.C. Cesquini, J.M. de S. e Silva, C.B. Woitiski, D. Mandelli, R. Rinaldi, U. Schuchardt, Adv. Synth. Catal., 2002, 344, 911.
[124] J.M. de S. e Silva, F.S. Vinhado, D. Mandelli, U. Schuchardt, R. Rinaldi, J. Mol. Catal. A: Chem., 2006, 252, 186.
[125] M.A. Uguina, J.A. Delgado, A. Rodríguez, J. Carretero, D. Gómez-Díaz, J. Mol. Catal. A: Chem., 2006, 256, 208.
[126] F. Chiker, F. Launay, J.P. Nogier, J.L. Bonardet, Environ. Chem. Lett., 2003, 1, 117.
[127] F. Chiker, F. Launay, J.P. Nogier, J.L. Bonardet, Green Chem., 2003, 5, 318.
[128] J.C. Van der Waal, M.S. Rigutto, R. van Bekkum, Appl. Catal., A, 1998, 167, 331.
[129] M.V. Cagnoli, S.G. Casuscelli, A.M. Alvarez, J.F. Bengoa, N.G. Gallegos, N.M. Samaniego, M.E. Crivello, G.E. Ghione, C.F. Pérez, E.R. Herrero, S.G. Marchetti, Appl. Catal., A, 2005, 287, 227.
[130] D. Marino, N.G. Gallegos, J.F. Bengoa, A.M. Alvarez, M.V. Cagnoli, S.G. Casuscelli, E.R. Herrero, S.G. Marchetti, Catal. Today, 2008, 133-135, 632.
[131] M.V. Cagnoli, S.G. Casuscelli, A.M. Alvarez, J.F. Bengoa, N.G. Gallegos, M.E. Crivello, E.R. Herrero, S.G. Marchetti, Catal. Today, 2005, 107-108, 397.
[132] M.L.A. von Holleben, P.R. Livotto, C.M. Schuch, J. Braz. Chem. Soc., 2001, 12, 42.
[133] M.A. Aramendia, V. Borau, C. Jimenez, J.M. Luque, J.M. Marinas, J.R. Ruiz, F.J. Urbano, Appl. Catal., A 2001, 216, 257.
[134] C.W. Wilson, P.E. Shaw, J. Org. Chem., 1973, 23, 1684.
[135] P.H. Jensen, K.B. Sharpless, J. Org. Chem., 1975, 40, 264.
[136] A.M. Santa, J.C. Vergara, L.A. Palacio, A. Echavarria, Catal. Today, 2008, 135-135, 80.
[137] N. Venkatathri, R. Srivastava, Catal. Commun., 2005, 6, 177.
[138] G. Grigoropoulou, J.H. Clark, Tetrahedron Lett., 2006, 47, 4461.

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUS5-0017-0060