P. Gallezot and D. Richard, Catal. Adúriz and O.A. Augustine, D.C. Migliorini, R.E. Hydrogenation of (–)-Menthone, (+)-Isomenthone, and (+)-Pulegone with Platinum/Tin Catalysts. Catalysts modified with (2R,3R)-(+)-tartaric acid were tested as well. Smith and C. Amezcua, Magn. 257, (, 1900, La Plata, Argentina, Facultad de Farmacia y Bioquímica, UBA, Departamento de Química Orgánica, Junín 954, (, 1113, Buenos Aires, Argentina, Albertina Moglioni & Graciela Y. Moltrasio Iglesias, You can also search for this author in This material is available via the Internet at http://pubs.acs.org. © 2020 Springer Nature Switzerland AG. redistribute this material, requesters must process their own requests via the RightsLink permission Am. McGraw-Hill, New York, N.Y., 1962. Roberts, J. Org. Correspondence to Research on Chemical Intermediates Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. T. Chihara and K. Tanaka, Bull. Users are Wagner, W.M. Immediate online access to all issues from 2019. A.N. Res. Immediate online access to all issues from 2019. Please note: If you switch to a different device, you may be asked to login again with only your ACS ID. Beumel, J. 53, 3270 (1980). Moulder, Handbook of X-Ray Photoelectron Spectroscopy, ed. Subscription will auto renew annually. This “green” modification dramatically reduces the quantity of waste, eliminates the hazards of concentrated acid, and allows for the isomer ratio to be monitored as a function of time. Lett. T. Chihara and K. Tanaka, Bull. System Maintenance Alert: Due to planned maintenance of our internal systems, web functionality including order placement, price and availability checks and SDS display will not be available for Asia and several European countries from Saturday, November 7th at 2:30 CET until Sunday, November 8th at 7:00 AM CET. volume 26, pages913–922(2000)Cite this article. Surf. Google Scholar. CAS  130 (2000) 2063. The oxidation itself produced (-)-menthone with a purity of 98%. Jpn. Surf. Soc. Sci. Subscription will auto renew annually. 33 (1994) 1881. Soc. Ferretti, Appl. Khim. A traditional organic chemistry laboratory experiment involves the acid-catalyzed isomerization of (−)-menthone to (+)-isomenthone. For permission to reproduce, republish and A: Chemistry 186 (2002) 223. 8, 1920 (1989). Boelens Aroma Chemical Information Service (BACIS), The Netherlands (1996). - 37.97.185.129. system. Foscante, C.S. You have to login with your ACS ID befor you can login with your Mendeley account. Soc. Find more information about Crossref citation counts. Soc. Jpn. 36, S3 (1998). 64 (1990) 1. Information about how to use the RightsLink permission system can be found at By pooling their data, students can examine the effect of both catalyst quantity and temperature on the position of the equilibrium, and the rate of the reaction. This article has not yet been cited by other publications. 39, 1017 (1974). Tax calculation will be finalised during checkout. H. Rothbacher and F. Suteu, Pharmazie 222 (1969). Learn more about Institutional subscriptions. 41, 3461 (1976). Molecular Weight 154.25 . Soc. V. Vetere, G. Santori, A. Moglioni, G. Moltrasio, M. Casella and O. Ferretti, to be published. P. Ravi, R. Ravichandran and S. Divakar, J. Mol. G. Santori, M. Casella, G. Siri, O. Ferretti, A. Moglioni and G. Moltrasio, Stud. Department of Organic Technology, Institute of Chemical Technology — ICT Prague, Technická 5, 166 28, Prague 6, Czech Republic, You can also search for this author in not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information OUILUIVI. Chem. Murzin, A.E. Sodano, and M.J. Sisbarro, J. Org. 41, 1902 (1968). Catal. Chem. Muilemberg (Minnesota, USA, 1978). Chem. Electronic Supporting Information files are available without a subscription to ACS Web Editions. The catalysts Raney nickel and Ni/SiO2 were used for these hydrogenations. 83, 1246 (1961). 40 (1988) 81 and references therein. It is a monoterpene and a ketone; it is structurally related to menthol and is seen to have carbonyl positioned in the place of secondary alcohol. Catal. Catal. Chem. PubMed Google Scholar, Vetere, V., Santori, G.F., Moglioni, A. et al. 75 (2002) 225. https://doi.org/10.1163/156856700X00390, DOI: https://doi.org/10.1163/156856700X00390, Over 10 million scientific documents at your fingertips, Not logged in 6/28/11 Chirality, Gas Chromatography and Menthone Abstract The purpose of this experiment is to isomerize (-)-menthone to its diasteriomer (-)-isomenthone under acidic conditions. Many ketones can be toxic internally and topically. G.F. Santori, M.L. Phelps, J. 5) The observed optical rotation of a mixture of (-)-menthone and (+)-isomenthone with a concentration of 0.0662 g/ml was measured at +0.891° in a 1 decimeter (dm) cell. Find more information about Crossref citation counts. 96, 543 (1974). R.M. Students then test their hypothesis by performing the reaction with different catalyst quantities and at different temperatures. 41, 2396 (1976). Chem. - 193.70.89.154. © 2020 Springer Nature Switzerland AG. Calculate the mole fraction (x) of (+)-isomenthone using Equation 6. You’ve supercharged your research process with ACS and Mendeley! M. Sugahara, S. Tsuchida, I. Anazawa, Y. Takagi, and S. Teratani, Chem. Catal. Catal. The modification with tin was performed by means of the techniques of surface organometallic chemistry on metals. This is a preview of subscription content, log in to check access. A: Gen. 197 (2000) 141. K. Sakai, M. Ishige, H. Kono, I. Motoyama, K. Watwnabe, and K. Hata, Bull. Tax calculation will be finalised during checkout. Eng. 43, 442 (1970). Chem. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting 257, (, 1900, La Plata, Argentina, Virginia Vetere, Gerardo F. Santori, Mónica L. Casella & Osmar A. Ferretti, Facultad de Ingeniería de la UNLP, 47 No. the Altmetric Attention Score and how the score is calculated. G. Santori, M. Casella and O. Ferretti, J. Mol. Files available from the ACS website may be downloaded for personal use only. C.D. from the ACS website, either in whole or in part, in either machine-readable form or any other form Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. 29, 1531 (1973). The hydrogenation of these terpenones was favored by the presence of tin in the bimetallic phase. W.B. Various non-equilibrium mixtures of isomers were produced by means of these reactions, especially mixtures containing the less stable menthol isomers, (+)-neomenthol and (+)-neoisomenthol. J. Solodar, J. Org. Some can be convulsent, toxic to the liver, or neurotoxic in high doses. Phelps, J. Org. This experiment generates large quantities of organic and aqueous waste, and only allows the final ratio of isomers to be determined. Information. Isomerization of (−)-menthone and (+)-isomenthone occurred during these reactions. 4) Consider the ketones piperitone, menthone, and isomenthone. G.F. Santori, M.L. without permission from the American Chemical Society. The catalysts used showed a very low activity under the given reaction conditions. Makouangou, D.Y. J. Margitfalvi, M. Hegedüs, S. Göbölös, E. Kern-Tálas, P. Szedlacsek, S. Szabó and F. Nagy, Proc. Catal. This way of modifying the catalysts allowed stereoisomers of menthol to be obtained in a one-step process. Casella, G.J. A. Tungler, T. Máthé, Z. Bende and J. Petro, Appl. Jpn. Empirical Formula (Hill Notation) C 10 H 18 O . Get article recommendations from ACS based on references in your Mendeley library. Res Chem Intermed 26, 913–922 (2000). G.E. The hydrogenation of (-)-menthone, (+)-isomenthone, and (+)-pulegone over SiO2-supported Pt and Pt-Sn catalysts was studied in this work. B. Rickborn, J. Chem. Pavel Kukula. Am. L. Červený (Ed. The hydrogenation of (-)-menthone, (+)-isomenthone, and (+)-pulegone over SiO2-supported Pt and Pt-Sn catalysts was studied in this work. Sci. Collins, G.N. This way of modifying the catalysts allowed stereoisomers of menthol to be obtained in a one-step process. The rotational spectra of the monoterpenoids menthol, menthone, and isomenthone are reported in the frequency range of 2-8.5 GHz, obtained with broadband Fourier-transform microwave spectroscopy. 8th Int. 4, p. 903. CINDECA (UNLP-CONICET), 47 No. Kukula, P., Červený, L. Stereoselective hydrogenation of (−)-menthone and (+)-isomenthone mixture using nickel catalysts. The equilibrium mixture of (-)-menthone and (+)-isomenthone was prepared by (-)- menthol oxidation using peracetic acid in ethyl acetate using NaBr. Chem. https://doi.org/10.1023/A:1021444407222, DOI: https://doi.org/10.1023/A:1021444407222, Over 10 million scientific documents at your fingertips, Not logged in Davies and J.F. Akad. Find more information on the Altmetric Attention Score and how the score is calculated.