Google Scholar. Phelps, J. Org. (−)-Menthol was produced during these reactions to a limited extent, the production of (−)-isomenthol was barcly existent. H. Kuivila and O.F. Catal. Links to Plants Containing Isomenthone Chem. Catal. 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. M. Sugahara, S. Tsuchida, I. Anazawa, Y. Takagi, and S. Teratani, Chem. 31 (1987) 713. The hydrogenation of (-)-menthone, (+)-isomenthone, and (+)-pulegone over SiO2-supported Pt and Pt-Sn catalysts was studied in this work. Beumel, J. G.E. Please note: If you switch to a different device, you may be asked to login again with only your ACS ID. N.D. Zubareva, E.I. P. Ravi, R. Ravichandran and S. Divakar, J. Mol. 257, (, 1900, La Plata, Argentina, Virginia Vetere, Gerardo F. Santori, Mónica L. Casella & Osmar A. Ferretti, Facultad de Ingeniería de la UNLP, 47 No. This material is available via the Internet at http://pubs.acs.org. Learn more about Institutional subscriptions. Siri, H.R. Soc. Sci. The modification with tin was performed by means of the techniques of surface organometallic chemistry on metals. Calculate the mole fraction (x) of (+)-isomenthone using Equation 6. volume 26, pages913–922(2000)Cite this article. This article has not yet been cited by other publications. a3-Menthone enol acetate (VII) was pre-pared from both menthone and isomenthone by several workersl-5 J. 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. Find more information on the Altmetric Attention Score and how the score is calculated. Surf. Jpn. 41, 2396 (1976). https://doi.org/10.1163/156856700X00390, DOI: https://doi.org/10.1163/156856700X00390, Over 10 million scientific documents at your fingertips, Not logged in 40 (1988) 81 and references therein. Collins, G.N. Adúriz and O.A. 39, 1017 (1974). The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. T. Chihara and K. Tanaka, Bull. 4) Consider the ketones piperitone, menthone, and isomenthone. Eng. 4, p. 903. Sci. Phelps, J. 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. P.Z. Listy PubMed Google Scholar. Foscante, C.S. The modification with tin was performed by means of the techniques of surface organometallic chemistry on metals. In the present investigation, menthols were oxidized with sodium dichromate in sulfuric acid by usual way to give menthone and iso menthone and then the menthones, having two … 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. Pavel Kukula. G. Santori, M. Casella, G. Siri, O. Ferretti, A. Moglioni and G. Moltrasio, Stud. J. Margitfalvi, M. Hegedüs, S. Göbölös, E. Kern-Tálas, P. Szedlacsek, S. Szabó and F. Nagy, Proc. Chem. A: Gen. 197 (2000) 141. A traditional organic chemistry laboratory experiment involves the acid-catalyzed isomerization of (−)-menthone to (+)-isomenthone. McGraw-Hill, New York, N.Y., 1962. K. Sakai, M. Ishige, H. Kono, I. Motoyama, K. Watwnabe, and K. Hata, Bull. A “green” modification has been developed that replaces the mineral acid catalyst with an acid-form ion-exchange resin, AMBERLYST 15DRY. Correspondence to 34, 1075 (1969). Rev. Berlin, 1984, vol. D.C. Wigfield and D.J. Am. Chem. C.D. The hydrogenation of these terpenones was favored by the presence of tin in the bimetallic phase. Google Scholar. The equilibrium mixture of (-)-menthone and (+)-isomenthone was prepared by (-)- menthol oxidation using peracetic acid in ethyl acetate using NaBr. 1956, 2165 (1956). Soc. Chem. Surf. Chem. A. Tungler, T. Máthé, Z. Bende and J. Petro, Appl. A: Chemistry 186 (2002) 223. Do not overuse or use for prolonged periods of time. from the ACS website, either in whole or in part, in either machine-readable form or any other form http://pubs.acs.org/page/copyright/permissions.html. This experiment generates large quantities of organic and aqueous waste, and only allows the final ratio of isomers to be determined. Hydrogenation of (–)-Menthone, (+)-Isomenthone, and (+)-Pulegone with Platinum/Tin Catalysts. You have to login with your ACS ID befor you can login with your Mendeley account. without permission from the American Chemical Society. As part of the experimental procedure, students generate their own hypothesis regarding the position of the equilibrium using molecular modeling of (−)-menthone and (+)-isomenthone. R.M. Article Klabunovskii, and L.A. Kheifits, Izv. This way of modifying the catalysts allowed stereoisomers of menthol to be obtained in a one-step process. Nauk SSSR, Ser. Various non-equilibrium mixtures of isomers were produced by means of these reactions, especially mixtures containing the less stable menthol isomers, (+)-neomenthol and (+)-neoisomenthol. Chem. Catal. 112 (1988) 210. Catalysis Letters Catal. 19 (1985) 365. M. Bartók, Stereochemistry of Heterogeneous Metal Catalysis, John Wiley & Sons, New York, 1985. Sheldrake and J. Crosby, Chirality in Industry (Wiley, Chichester, 1992). Catal. 84, 2414 (1962). Tax calculation will be finalised during checkout. Catal. E. Eliel, S. Wilen and L. Mander, Stereochemistry of Organic Compounds (Wiley, 1994). - 188.8.131.52. Reson. © 2020 Springer Nature Switzerland AG. These metrics are regularly updated to reflect usage leading up to the last few days. G. Santori, M. Casella and O. Ferretti, J. Mol. Adúriz and O.A. Kinet. Users are Files available from the ACS website may be downloaded for personal use only. 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 The oxidation itself produced (-)-menthone with a purity of 98%. Immediate online access to all issues from 2019. 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. Res Chem Intermed 26, 913–922 (2000). This is a preview of subscription content, log in to check access. A traditional organic chemistry laboratory experiment involves the acid-catalyzed isomerization of (−)-menthone to (+)-isomenthone. The catalysts used showed a very low activity under the given reaction conditions. 64 (1990) 1. Gas chromatography is used to determine the percent isomerization. For permission to reproduce, republish and This experiment generates large quantities of organic and aqueous waste, and only allows the final ratio of isomers to be determined. A. Tungler, T. Máthé, Z. Bende, and J. Petro, Appl. Soc. CINDECA (UNLP-CONICET), 47 No. Its optical rotation was -16.02° within the wavelength À = 589 nm and at the temperature 20°C. The pedagogical impact of the experiment has been significantly improved through examination of the effect of catalysis on the position of the equilibrium and on the kinetics of the reaction. Get article recommendations from ACS based on references in your Mendeley library. Chem. Davies and J.F. 8th Int. redistribute this material, requesters must process their own requests via the RightsLink permission Catalysis Letters 84, 251–257 (2002). H. Rothbacher and F. Suteu, Pharmazie 222 (1969). J. Solodar, J. Org. Akad. Subscription will auto renew annually. J.H. Chem. Catal. Soc. Sci. Soc. Ferretti, React. Am. S. Mutsui, H. Saito, Y. Yamashita, M. Kaminaga, and Y. Senda, Tetrahedron Soc. Catalysts modified with (2R,3R)-(+)-tartaric acid were tested as well. 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. 96, 543 (1974). Google Scholar. Students then test their hypothesis by performing the reaction with different catalyst quantities and at different temperatures. Chem. 53, 3270 (1980).
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