Eco-friendly Synthesis of Cyclododecanone from Cyclododecatriene

Qi Feng, De-Kai Yuan, Dao-Quan Wang, Xiao-Mei Liang, Jian-Jun Zhang, Jin-Ping Wu, Fu-Heng Chen

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DOI: 10.4236/gsc.2011.13011                

Abstract

An eco-friendly synthesis of cyclododecanone (CDON) from cyclododecatriene (CDT) is described. Selec- tive epoxidation of CDT with hydrogen peroxide using hexadecyl trimethyl ammonium heteropolyphospha- totungstate [(n-C16H33NMe3)3PW4O16, HAHPT] as catalyst and water as solvent followed by the hydrogena- tion on Raney nickel catalyst gave cyclododecanol (CDOL). The latter was oxidized with hydrogen peroxide using HAHPT as catalyst and a mixture of water and t-butanol as solvent to afford CDON. The total yield was 53.4% under the optimum reaction conditions.

Keywords

Eco-Friendly Synthesis, Cyclododecanone, Cyclododecatriene, Hexadecyl Trimethyl Ammonium Heteropolyphosphatotungstate

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	S. S. Mahajan, M. M. Sharma and T. Sridhar, “Uncata-lyzed Oxidation of 1,5,9-Cyclododecatriene with Mole-cular Oxygen,” Industrial and Engineering Chemistry Research, Vol. 46, No. 10, 2007, pp. 3057-3062. doi:10.1021/ie061072n
[2]	H. Rademacher and H.-W. Voges, “Method for Preparing Lactams Having 8 to 15 Carbon Atoms from the Corres-ponding Oximes,” US Patent No. 4689412, 1987.
[3]	Z.-F. Xie and K. Sakai, “Construction of Medium- and Large-Sized Cyclic .Beta.-Keto Esters (or Nitriles) via One-Pot Three-Carbon Ring Expansion of Carbocyc- lic .Beta.-Keto Esters and Its Application to the Synthesis of (-)-Muscone,” The Journal of Organic Chemistry, Vol. 55, No. 3, 1990, pp. 820-826. doi:10.1021/jo00290a009
[4]	P. Dowd and S.-C. Choi, “Free Radical Ring Expansion and Rearrangement of Large Carbocyclic Rings,” Tetra-hedron Letters, Vol. 32, No. 5, 1991, pp. 565-568. doi:10.1016/S0040-4039(00)74828-3
[5]	D. S. Wang, D. Q. Wang and C. H. Zhou, “Title of This Paper,” Acta Chimica Sinica, Vol. 53, No. *, 1995, pp. 909-915.
[6]	S. Stanchev, B. Milenkov and M. Hesse, “A Short Syn-thesis of 15-Pentadecanolide,” Tetrahedron Letters, Vol. 34, No. 38, 1993, pp. 6107-6108. doi:10.1016/S0040-4039(00)61741-0
[7]	Y. H. Dong, X. M. Liang, H. Z. Yuan, et al., “Potential Green Fungicide: 16-Oxo-1-Oxa-4-Azoniacyclohexade- can-4-Ium Tetrafluoroborate,” Green Chemistry, Vol. 10, No. 9, 2008, pp. 990-994. doi:10.1039/b805797d
[8]	J. X. Huang, X. M. Liang, J. J. Zhang, et al., “Fungicidal Activity of 12-Propoxyimino-1, 15-Pentadecanlactam on Selected Crops,” Crop Protection, Vol. 28, No. 11, 2009, pp. 947-951. doi:10.1016/j.cropro.2009.07.017
[9]	H. H. Wasserman, G. C. Rodgers and D. D. Keith, “Me- tacycloprodigiosin, a Tripyrrole Pigment from Strepto-myces Longisporus Rubber,” Journal of the American Chemical Society, Vol. 91, No. 5, 1969, pp. 1263-1264. doi:10.1021/ja01033a065
[10]	H. H. Wasserman, D. D. Keith and J. Nadelson, “Synthe-sis of Metacycloprodigiosin,” Journal of the American Chemical Society, Vol. 91, No. 5, 1969, pp. 1264-1265. doi:10.1021/ja01033a066
[11]	L. Ruzicka, M. Stoll and H. Schinz, “Zur Kenntnis des Kohlenstoffringes II. Synthese der carbocyclischen Ketone vom Zehnerbis zum Achtzehnerring,” Helvetica Chemical Acta, Vol. 9, No. 1, 1926, pp. 249-264. doi:10.1002/hlca.19260090130
[12]	V. Prelog, L. Frenkiel, M. Kobelt, et al., “Zur Kenntnis des Kohlenstoffringes. Ein Herstellungsverfahren für Vielgliedrige Cyclanone,” Helvetica Chemical Acta, Vol. 30, No. 6, 1947, pp. 1741-1749. doi:10.1002/hlca.19470300637
[13]	G. Wilke and H. Muller, “Title of This Patent,” DE No. 1043329, 1958.
[14]	H. Weber, W. Ring, U. Hochmuth, et al., “Zur Bildung- sweise von cis,trans,trans-Cyclododecatrien-(1,5,9) Mit-tels Titanhaltiger Ziegler-Katalysatoren,” Justus Liebigs Annalen der Chemie, Vol. 681, No. 1, 1965, pp. 10-20. doi:10.1002/jlac.19656810103
[15]	X. J. Yan, Q. Feng, S. H. Jin, et al., “Title of This Paper,” Fine Chemical Intermediates, Vol. 38, No. 2, 2008, pp. 1-8.
[16]	J. Lebbe, “Quantitative Analysis,” In: J. Tranchani, Ed., Practical Manual of Gas Chromatography, Elsevier, New York, 1969, pp. 257-286.
[17]	S. J. Zhang, S. Gao, Z. W. Xi, et al., “Solvent-Free Oxi-dation of Alcohols Catalyzed by an Efficient and Reusable Heteropolyphosphatotungstate,” Catalysis Communi-cations, Vol. 8, No. 3, 2007, pp. 531-534. doi:10.1016/j.catcom.2006.02.020
[18]	X. G. Yang, S. J. Zhang, M. Li, et al., “Synthesis of MgAPO-11 Molecular Sieves and the Catalytic Perfor-mance of Pt/MgAPO-11 for n-Dodecane Hydroisomeri-zation,” Chinese Journal of Catalysis, Vol. 27, No. 1, 2006, pp. 50-54. doi:10.1016/S1872-2067(06)60055-7
[19]	N. Kuroda, T. Matsuzaki and M.Yamanaka, “Method of Reducing Epoxidized Organic Compound with Hydro-gen,” WO/2000026165, 2000.
[20]	B. S. Lane and K. Burgess, “Metal-Catalyzed Epoxida-tions of Alkenes with Hydrogen Peroxide,” Chemical Re-views, Vol. 103, No. 7, 2003, pp. 2457-2473. doi:10.1021/cr020471z
[21]	N. Mizuno, K. Yamaguchi and K. Kamata, “Epoxidation of Olefins with Hydrogen Peroxide Catalyzed by Po-lyoxometalates,” Coordination Chemical Reviews, Vol. 249, No. 17-18, 2005, pp. 1944-1956. doi:10.1016/j.ccr.2004.11.019
[22]	Z. W. Xi, N. Zhou, Y. Sun, et al., “Reaction-Controlled Phase-Transfer Catalysis for Propylene Epoxidation to Propylene Oxide,” Science, Vol. 292, No. 5591, 2001, pp. 1139-1141. doi:10.1126/science.292.5519.1139
[23]	K. L. Li, N. Zhou and Z. W. Xi, “Title of This Paper,” Chinese Journal of Catalysis, Vol. 23, No. 2, 2002, pp. 125-126.
[24]	X. G, Yang, S. J. Zhang, M. Li, et al., “Title of This Pa-per,” Name of Journal, Vol. 27, No. 1, 2006, pp. 50-54,
[25]	N.Kuroda and T.Nakamura, JP2001302570, 2001.
[26]	T. Matsuzaki, Y. Nakamura and T. Manabe, “Method for Producing Cycloalkanol and Cycloalkanone,” JP No. 2002161057, 2002.
[27]	T .Matsuzaki, Y. Nakamura and O. Yamazaki, “Process for the Production of a Cycloalkanone and/or a Cycloal-kanol,” JP No. 2002114732, 2002.
[28]	T. Matsuzaki, Y. Nakamura and O. Yamazaki, “Method for Producing Cycloalkanol and Cycloalkanone,” JP No. 2002047220, 2002.
[29]	P. Mueller and J. Godoy, “Catalyzed Oxidation of Alco-hols and Aldehydes with Iodosylbenzene,” Tetrahedron Letters, Vol. 22, No. 25, 1981, pp. 2361-2364. doi:10.1016/S0040-4039(01)82906-3
[30]	M. E. Krafft and B. Zorc, “Oxidation of Secondary Al-cohols Using Raney Nickel,” The Journal of Organic Chemistry, Vol. 51, No. 26, 1986, pp. 5482-5484. doi:10.1021/jo00376a099
[31]	Y. Kurusu and Y.Masuyama, “Catalysis by Tetrabromoo- xomolybdate(V) Complex: Oxidation of Olefins and Al-cohols with t-Butyl Hydroperoxide,” Polyhedron, Vol. 5, No. 1-2, 1986, pp. 289-296. doi:10.1016/S0277-5387(00)84924-4
[32]	T. Morimoto, M. Hirano, H. Ashiya, et al., “Oxidation of Aliphatic Secondary and Benzylic Alcohols to Carbonyl Compounds by Peracetic Acid in the Presence of Sodium Bromide in Acetic Acid,” Bulletin of the Chemical Society of Japan, Vol. 60, No. 11, 1987, pp. 4143-4144. doi:10.1246/bcsj.60.4143
[33]	T. Morimoto, M. Hirano, Y. Aikawa, et al., ““Title of This Paper,” Journal of the Chemical Society, Perkin Transactions 1, No. 8, 1988, pp. 2423-4.
[34]	T. Nishiguchi and F.Asano, “Oxidation of Alcohols by Metallic Nitrates Supported on Silica Gel,” The Journal of Organic Chemistry, Vol. 54, No. 7, 1989, pp. 1531- 1535. doi:10.1021/jo00268a011
[35]	M. Yamaguchi, T. Takata and T. Endo, “Oxidation of Cycloalkanols to the Corresponding Cycloalkanones with Chlorine in the Presence of Nitroxide Radical as a Me-diator,” Bulletin of the Chemical Society of Japan, Vol. 63, No. 3, 1990, pp. 947-949. doi:10.1246/bcsj.63.947
[36]	S. Furusaki, M. Matsuda and M. Hida, “Production of Cyclododecanone,” JP No. 03115247, 1991.