dehydrogenation of alcohol to aldehyde

Published by on November 13, 2020

In: Beller M, Bolm C (eds) Transition metals for organic synthesis: Building Blocks and Fine Chemicals, vol 2, 2nd edn. A process for the production of a dehydrogenation product of an alcohol which comprises contacting a monohydric alcohol of the class consisting of primary alcohols containing at least three carbon atoms and secondary alcohols with a dehydrogenation catalyst consisting essentially of alloyed copper and zinc at a pressure of from about 2 to about 100 atmospheres and a temperature greater than about 400" C. but below the temperature at which substantial dehydration occurs. The dried cake was reduced to small lumps and charged into the re- ; action tube. J Chem Soc Dalton Trans 489–495. The mass was'then 4, powdered and soaked with 15% sodium carbonate solution. For example, a primary alcohol having the formula R-CH2OH will yield an aldehyde having the formula R-CHO while a secondary alcohol having the formula R CHOH / will yield a ketone having the formula 20 \C= The prior methods of accomplishing these results, however, are usually attended by one or .- more disadvantages. Chem Commun 655–656. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. Organometallics 25:873–881, Morton D, Cole-Hamilton DJ (1987) Rapid thermal hydrogen production from alcohols catalysed by [Rh(2,2′-bipyridyl)2]Cl. The human genes that encode class II, III, IV, and V alcohol dehydrogenases are ADH4, ADH5, ADH7, and ADH6, respectively. doi:10.1039/DT9890000489, Delgado-Lieta E, Luke MA, Jones RF, Cole-Hamilton DJ (1982) The photochemical decomposition of alcohols catalysed by tri(isopropyl) phosphine complexes of rhodium(I). Acceptorless catalytic alcohol dehydrogenation. 2020-11-13T18:01:35+08:00 Chem Soc Rev 35:237–248, Gunanathan C, Ben-David Y, Milstein D (2007) Direct synthesis of amides from alcohols and amines with liberation of H2. A process for the production of a dehydrogenation product of an alcohol which comprises contacting a monohydric alcohol of the class consisting of primary alcohols containing at least three carbon atoms and secondary alcohols with a dehydrogenation catalyst essentially comprising a heavy metal selected from Groups 1, 2, 7 and 8 of the Periodic System at a pressure not substantially less than two atmospheres and a temperature favorable to dehydrogenation but below the temperature at which substantial dehydration occurs, subsequently cooling the treated material under a pressure not substantially less than two atmospheres to separate a major part of the condensable materials from the hydrogen formed, and then treating said hydrogen, while substantially maintaining the pressure, with a suitable solvent for the substantially complete removal of organic materials therefrom. The LibreTexts libraries are Powered by MindTouch® and are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. doi:10.1039/C39880001154, Morton D, Cole-Hamilton DJ, Utuk ID, Paneque-Sosa M, Lopez-Poveda M (1989) Hydrogen production from ethanol catalysed by group 8 metal complexes. Chem Eur J 16:6820–6827, Makarov IS, Fristrup P, Madsen R (2012) Mechanistic Investigation of the ruthenium–N-heterocyclic carbene catalyzed amidation of amines with alcohols. J Am Chem Soc 111:7088–7093, Xu W, Rosini GP, Gupta M, Jensen CM, Kaska WC, KroghJespersen K, Goldman AS (1997) Thermochemical alkane dehydrogenation catalyzed in solution without the use of a hydrogen acceptor. [Ir]/[Rh]/[Ru]-catalyzed hydroxymethylation of n-octane to n-nonanol. A process for the production of a dehydrogenation product of an alcohol which comprises contacting a monohydric alcohol of the class consisting of primary alcohols containing at least three carbon atoms and secondary alcohols with a dehydrogenation catalyst essentially comprising copper and zinc at a pressure not substantially less than two atmospheres and at a temperature at which dehydrogenation occurs while substantial dehydration is avoided. Mechanistic understanding at the molecular level helps to develop new generation dehydrogenation catalysts. These additional metal oxides are ordinarily added in relatively small amount, as, for example, 5% to 10% by weight in the final catalyst. Tetrahedron Lett 46:8233–8235, Junge H, Beller M (2005) Ruthenium-catalyzed generation of hydrogen from iso-propanol. Angew Chem Int Ed 44:6318–6323, Rodríguez-Lugo RE, Trincado M, Vogt M, Tewes F, Santiso-Quinones G, Grützmacher H (2013) A homogeneous transition metal complex for clean hydrogen production from methanol–water mixtures. doi:10.1007/3418_2015_162, Sean CE, Hadzovic A, Morris RH (2004) Mechanisms of the H2-hydrogenation and transfer hydrogenation of polar bonds catalyzed by ruthenium hydride complexes. doi:10.1039/C4EE00389F, Morton D, Cole-Hamilton DJ (1988) Molecular hydrogen complexes in catalysis: highly efficient hydrogen production from alcoholic substrates catalysed by ruthenium complexes. [29] The level of activity may not be dependent only on level of expression but also on allelic diversity among the population. [24] It catalyzes the oxidation of ethanol to acetaldehyde (ethanal): This allows the consumption of alcoholic beverages, but its evolutionary purpose is probably the breakdown of alcohols naturally contained in foods or produced by bacteria in the digestive tract. The simplest large-scale procedure for reduction of aldehydes and ketones to alcohols is by catalytic hydrogenation: The advantage over most other kinds of reduction is that usually the product can be obtained simply by filtration from the catalyst, then distillation. Science 341:1229712, Gunanathan C, Milstein D (2014) Bond activation and catalysis by ruthenium pincer complexes. Angew Chem Int Ed 47:8661–8864, Ben-Ari E, Leitus G, Shimon LJW, Milstein D (2006) Metal–ligand cooperation in C–H and H2 activation by an electron-rich PNP Ir(I) system: facile ligand dearomatization–aromatization as key steps. 3. [7] The enzyme responsible for the conversion of acetaldehyde to acetate, however, remains unaffected, which leads to differential rates of substrate catalysis and causes a buildup of toxic acetaldehyde, causing cell damage.

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