Nitrate esters are typically prepared by condensation of nitric acid and the alcohol:[1][2] For example, the simplest nitrate ester, methyl nitrate, is formed by reaction of methanol and nitric acid in the presence of sulfuric acid:[3]
Formation of a nitrate ester is called a nitrooxylation (less commonly, nitroxylation).
Explosive propertiesedit
The thermal decomposition of nitrate esters mainly yields the gases molecular nitrogen (N2) and carbon dioxide. The considerable chemical energy of the detonation is due to the high strength of the bond in molecular nitrogen. This stoichiometry is illustrated by the equation for the detonation of nitroglycerin.
Illustrative of the highly sensitive nature of some organic nitrates is Si(CH2ONO2)4.[4][5] A single crystal of this compound detonates even upon contact with a teflon spatula and in fact made full characterization impossible. Another contributor to its exothermic decomposition (inferred from much safer in silico experimentation) is the ability of silicon in its crystal phase to coordinate to two oxygen nitrito groups in addition to regular coordination to the four carbon atoms. This additional coordination would make formation of silicon dioxide (one of the decomposition products) more facile.
Acetyl nitrate is a nitrate anhydride, being derived from the condensation of nitric and acetic acids.
Referencesedit
^Snyder, H. R.; Handrick, R. G.; Brooks, L. A. (1942). "Imidazole". Organic Syntheses.; Collective Volume, vol. 3, p. 471
^Boschan, Robert; Merrow, Raymond T.; van Dolah, Robert W. (1955-06-01). "The Chemistry of Nitrate Esters". Chemical Reviews. 55 (3): 485–510. doi:10.1021/cr50003a001. ISSN 0009-2665.
^Alvin P. Black & Frank H. Babers. "Methyl nitrate". Organic Syntheses.; Collective Volume, vol. 2, p. 412
^The Sila-Explosives Si(CH2N3)4 and Si(CH2ONO2)4: Silicon Analogues of the Common Explosives Pentaerythrityl Tetraazide, C(CH2N3)4, and Pentaerythritol Tetranitrate, C(CH2ONO2)4Thomas M. Klapötke, Burkhard Krumm, Rainer Ilg, Dennis Troegel, and Reinhold Tacke J. Am. Chem. Soc.; 2007doi:10.1021/ja071299p
nitrate, ester, confused, with, nitro, compound, organic, chemistry, nitrate, ester, organic, functional, group, with, formula, ono2, where, stands, organyl, group, they, esters, nitric, acid, alcohols, well, known, example, nitroglycerin, which, nitro, compou. Not to be confused with Nitro compound In organic chemistry a nitrate ester is an organic functional group with the formula R ONO2 where R stands for any organyl group They are the esters of nitric acid and alcohols A well known example is nitroglycerin which is not a nitro compound despite its name Pentaerythritol tetranitrate is a commercially important explosive that contains four nitrate ester groups Contents 1 Synthesis and reactions 2 Explosive properties 3 Medical use 4 Related compounds 5 ReferencesSynthesis and reactions editNitrate esters are typically prepared by condensation of nitric acid and the alcohol 1 2 For example the simplest nitrate ester methyl nitrate is formed by reaction of methanol and nitric acid in the presence of sulfuric acid 3 CH 3 OH HNO 3 CH 3 ONO 2 H 2 O displaystyle ce CH3OH HNO3 gt CH3ONO2 H2O nbsp Formation of a nitrate ester is called a nitrooxylation less commonly nitroxylation Explosive properties editThe thermal decomposition of nitrate esters mainly yields the gases molecular nitrogen N2 and carbon dioxide The considerable chemical energy of the detonation is due to the high strength of the bond in molecular nitrogen This stoichiometry is illustrated by the equation for the detonation of nitroglycerin nbsp Illustrative of the highly sensitive nature of some organic nitrates is Si CH2ONO2 4 4 5 A single crystal of this compound detonates even upon contact with a teflon spatula and in fact made full characterization impossible Another contributor to its exothermic decomposition inferred from much safer in silico experimentation is the ability of silicon in its crystal phase to coordinate to two oxygen nitrito groups in addition to regular coordination to the four carbon atoms This additional coordination would make formation of silicon dioxide one of the decomposition products more facile Medical use editMain article Glyceryl trinitrate pharmacology The nitrate esters isosorbide dinitrate Isordil and isosorbide mononitrate Imdur Ismo Monoket Mononitron are converted in the body to nitric oxide a potent natural vasodilator In medicine these esters are used as a medicine for angina pectoris ischemic heart disease Related compounds editAcetyl nitrate is a nitrate anhydride being derived from the condensation of nitric and acetic acids References edit Snyder H R Handrick R G Brooks L A 1942 Imidazole Organic Syntheses Collective Volume vol 3 p 471 Boschan Robert Merrow Raymond T van Dolah Robert W 1955 06 01 The Chemistry of Nitrate Esters Chemical Reviews 55 3 485 510 doi 10 1021 cr50003a001 ISSN 0009 2665 Alvin P Black amp Frank H Babers Methyl nitrate Organic Syntheses Collective Volume vol 2 p 412 The Sila Explosives Si CH2N3 4 and Si CH2ONO2 4 Silicon Analogues of the Common Explosives Pentaerythrityl Tetraazide C CH2N3 4 and Pentaerythritol Tetranitrate C CH2ONO2 4Thomas M Klapotke Burkhard Krumm Rainer Ilg Dennis Troegel and Reinhold Tacke J Am Chem Soc 2007 doi 10 1021 ja071299p Sila Explosives Offer A Better Bang Stephen K Ritter Chemical amp Engineering News May 7 2007Link Retrieved from https en wikipedia org w index php title Nitrate ester amp oldid 1184341430, wikipedia, wiki, book, books, library,
