Sn(II)-catalyzed β-citronellol esterification: a Brønsted acid-free process for synthesis of fragrances at room temperature

作者: M. J. da Silva , A. A. Julio , K. T. dos Santos

DOI: 10.1039/C4CY01069H

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摘要: Simple SnCl2·2H2O was demonstrated to be able catalyze β-citronellol esterification with acetic acid at room temperature under solvent-free conditions, achieving high conversion and ester selectivity (ca. 88% 99%, respectively). Tin(II) chloride is a stable water-tolerant Lewis that commercially available less corrosive than Bronsted catalysts. This selective process an attractive alternative the mineral acid-catalyzed because it avoids product neutralization common in those reactions. The effects of main reaction parameters such as reactant stoichiometry, temperature, solvent, catalyst concentration were assessed. Among tin catalysts evaluated, SnCl2 most active selective. Moreover, sulfuric p-toluenesulfonic catalysts, acids investigated herein, additional advantages being solid catalyst.

参考文章(31)
H.F. de Castro, P.C. de Oliveira, E.B. Pereira, Evaluation of different approaches for lipase catalysed synthesis of citronellyl acetate Biotechnology Letters. ,vol. 19, pp. 229- 232 ,(1997) , 10.1023/A:1018349406159
Milene L Da Silva, Ana P Figueiredo, Abiney L Cardoso, Ricardo Natalino, Márcio J Da Silva, Effect of Water on the Ethanolysis of Waste Cooking Soybean Oil Using a Tin(II) Chloride Catalyst Journal of the American Oil Chemists' Society. ,vol. 88, pp. 1431- 1437 ,(2011) , 10.1007/S11746-011-1794-Z
Paul A. Claon, Casimir C. Akoh, Effect of reaction parameters on SP435 lipase-catalyzed synthesis of citronellyl acetate in organic solvent Enzyme and Microbial Technology. ,vol. 16, pp. 835- 838 ,(1994) , 10.1016/0141-0229(94)90056-6
Jing Luo, Jingye Yu, Raymond J. Gorte, Eyas Mahmoud, Dionisios G. Vlachos, Michael A. Smith, The effect of oxide acidity on HMF etherification Catalysis Science & Technology. ,vol. 4, pp. 3074- 3081 ,(2014) , 10.1039/C4CY00563E
Nam T. Nguyen, Kristofer J. Thurecht, Steve M. Howdle, Derek J. Irvine, Facile one-spot synthesis of highly branched polycaprolactone Polymer Chemistry. ,vol. 5, pp. 2997- 3008 ,(2014) , 10.1039/C3PY01725G
M. Karra-Chaabouni, S. Pulvin, D. Touraud, D. Thomas, Enzymatic synthesis of geraniol esters in a solvent-free system by lipases Biotechnology Letters. ,vol. 18, pp. 1083- 1088 ,(1996) , 10.1007/BF00129736
Arthur Batista Ferreira, Abiney Lemos Cardoso, Márcio José da Silva, Novel and Highly Efficient SnBr2-Catalyzed Esterification Reactions of Fatty Acids: The Notable Anion Ligand Effect Catalysis Letters. ,vol. 143, pp. 1240- 1246 ,(2013) , 10.1007/S10562-013-1089-0
Danieli Marcolan Carari, Márcio José da Silva, Fe(NO 3 ) 3 -Catalyzed Monoterpene Oxidation by Hydrogen Peroxide: An Inexpensive and Environmentally Benign Oxidative Process Catalysis Letters. ,vol. 144, pp. 615- 622 ,(2014) , 10.1007/S10562-013-1189-X
Paul T Anastas, Lauren B Bartlett, Mary M Kirchhoff, Tracy C Williamson, None, The role of catalysis in the design, development, and implementation of green chemistry Catalysis Today. ,vol. 55, pp. 11- 22 ,(2000) , 10.1016/S0920-5861(99)00222-9
Fernanda P. Silva, Marcos J. Jacinto, Richard Landers, Liane M. Rossi, Selective Allylic oxidation of Cyclohexene by a Magnetically Recoverable Cobalt Oxide Catalyst Catalysis Letters. ,vol. 141, pp. 432- 437 ,(2011) , 10.1007/S10562-010-0512-Z