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Synthesis of nitric acid esters from alcohols in a dinitrogen pentoxide/carbon dioxide liquid system

Ilya Vladimirovich Kuchurov 1
Ilya Vladimirovich Kuchurov
, 
Igor Vladimirovich Fomenkov 1
Igor Vladimirovich Fomenkov
, 
Sergei Grigorievich Zlotin 1
Sergei Grigorievich Zlotin
, 
Vladimir Alexandrovich Tartakovsky 1
Vladimir Alexandrovich Tartakovsky
10.1016/j.mencom.2012.03.004
Published 2012-02-27
Communication , Volume 22, Issue 2, 67-69
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Kuchurov I. V. et al. Synthesis of nitric acid esters from alcohols in a dinitrogen pentoxide/carbon dioxide liquid system // Mendeleev Communications. 2012. Vol. 22. No. 2. pp. 67-69.
GOST all authors (up to 50) Copy
Kuchurov I. V., Fomenkov I. V., Zlotin S. G., Tartakovsky V. A. Synthesis of nitric acid esters from alcohols in a dinitrogen pentoxide/carbon dioxide liquid system // Mendeleev Communications. 2012. Vol. 22. No. 2. pp. 67-69.
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TY - JOUR
DO - 10.1016/j.mencom.2012.03.004
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.03.004
TI - Synthesis of nitric acid esters from alcohols in a dinitrogen pentoxide/carbon dioxide liquid system
T2 - Mendeleev Communications
AU - Kuchurov, Ilya Vladimirovich
AU - Fomenkov, Igor Vladimirovich
AU - Zlotin, Sergei Grigorievich
AU - Tartakovsky, Vladimir Alexandrovich
PY - 2012
DA - 2012/02/27
PB - Mendeleev Communications
SP - 67-69
IS - 2
VL - 22
ER -
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@article{2012_Kuchurov,
author = {Ilya Vladimirovich Kuchurov and Igor Vladimirovich Fomenkov and Sergei Grigorievich Zlotin and Vladimir Alexandrovich Tartakovsky},
title = {Synthesis of nitric acid esters from alcohols in a dinitrogen pentoxide/carbon dioxide liquid system},
journal = {Mendeleev Communications},
year = {2012},
volume = {22},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.03.004},
number = {2},
pages = {67--69},
doi = {10.1016/j.mencom.2012.03.004}
}
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Kuchurov, Ilya Vladimirovich, et al. “Synthesis of nitric acid esters from alcohols in a dinitrogen pentoxide/carbon dioxide liquid system.” Mendeleev Communications, vol. 22, no. 2, Feb. 2012, pp. 67-69. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.03.004.

Abstract

Organic nitric acid esters have been prepared in 89–98% yield by the nitration of the corresponding alcohols and polyols with N2O5 in liquid CO2.

References

1.
10.1016/j.mencom.2012.03.004_bib0005_1
Urbánski
1965
2.
R. Mayer, Explosives, 5th edn. (electronic), Wiley-VCH Verlag, GmbH, 2002.
3.
10.1016/j.mencom.2012.03.004_bib0010_1
Ahlner
Pharmacol. Rev., 1991
4.
NO donors. Part 18: Bioactive metabolites of GTN and PETN—Synthesis and vasorelaxant properties
Lange K., Koenig A., Roegler C., Seeling A., Lehmann J.
Bioorganic and Medicinal Chemistry Letters, 2009
5.
Aspects of Nitrate Ester Metabolism
Litchfield M.H.
Journal of Pharmaceutical Sciences, 1971
6.
The preparation of some glucose nitrates
O'Meara D., Shepherd D.M.
Journal of the Chemical Society (Resumed), 1955
8.
The Chemistry of Nitrate Esters
Boschan R., Merrow R.T., van Dolah R.W.
Chemical Reviews, 1955
9.
Sugar Nitrates
Honeyman J., Morgan J.W.
Advances in Carbohydrate Chemistry, 1957
10.
Synthesis and reactions of 2-nitro-1-propen-3-ol
Oreshko G.V., Eremenko L.T.
Russian Chemical Bulletin, 1989
11.
Some aromatic nitrate esters: synthesis, structural aspects, thermal and explosive properties
Agrawal J.P., Surve R.N., Mehilal, Sonawane S.H.
Journal of Hazardous Materials, 2000
12.
10.1016/j.mencom.2012.03.004_bib0020_5
Olah
Nitration: Methods and Mechanisms, 1989
13.
The Electrolytic Reduction of Simple Nitrate Esters1
Kaufman F., Cook H.J., Davis S.M.
Journal of the American Chemical Society, 1952
14.
Nitration of Unsaturated Alcohols1
WOLFROM M.L., McFADDEN G.H., CHANEY A.
Journal of Organic Chemistry, 1960
15.
Circulardichroismus—XXXII
Snatzke G., Laurent H., Wiechert R.
Tetrahedron, 1969
18.
Selective nitration of paclitaxel and related taxanes
Rao K.V., Johnson J.H.
Tetrahedron Letters, 1998
19.
10.1016/j.mencom.2012.03.004_bib0030_1
Yu.
Usp. Khim, 1983
20.
J. H. Ridd, T. Yoshida, in Industrial and Laboratory Nitrations, ACS Symposium Series 22, eds. L. F. Albright and C. Hanson,;1; American Chemical Society, Washington, DC,;1; 1976, ch. 6.
21.
G. A. Olah, in Chemistry of Energetic Materials, eds. G. A. Olah and D. R. Squire, Academic Press, New York, 1991, ch. 7.
22.
10.1016/j.mencom.2012.03.004_bib0035_1
Feldman
J. Am. Chem. Soc., 1957
23.
Nitration studies. XVI. Conversion of nitrite and nitrate esters in nitro alkanes
Bachman G.B., Connon N.W.
Journal of Organic Chemistry, 1969
24.
10.1016/j.mencom.2012.03.004_bib0035_3
Elias
Tappi J., 1958
28.
R. W. Millar, M.E. Colclough, A.W. Arber, R.P. Claridge, R.M. Endsor and J. Hamid, in Energetic Materials: Chemistry, Hazards and Environmental Aspects, eds. J. R. Howell and T. E. Fletcher, Nova Science Pub. Inc., New York, 2010.
30.
Aromatic substitution. 45. Transfer nitration of aromatics with N-nitropyridinium and quinolinium ions
Olah G.A., Narang S.C., Olah J.A., Pearson R.L., Cupas C.A.
Journal of the American Chemical Society, 1980
31.
The Synthesis and Application of Novel Nitrating and Nitrosating Agents
Hakimalahi G.H., Sharghi H., Zarrinmayeh H., Khalafi-Nezhad A.
Helvetica Chimica Acta, 1984
32.
10.1016/j.mencom.2012.03.004_bib0040_4
Li
Synthesis, 1993
33.
10.1016/j.mencom.2012.03.004_bib0040_5
Cupas
Synthesis, 1978
34.
NEW ONE-POT SYNTHESIS OF ALKYL NITRATES FROM ALCOHOLS
Castedo L., Marcos C.F., Monteagudo M., Tojo G.
Synthetic Communications, 1992
35.
10.1016/j.mencom.2012.03.004_bib0045
Agrawal
Chemical World, 2006
37.
10.1016/j.mencom.2012.03.004_bib0055
Jessop
Chemical Syntheses Using Supercritical Fluids, 1999
38.
Innovative polymer processing in carbon dioxide
Farncomb R.E., Nauflett G.W.
Waste Management, 1998
39.
10.1016/j.mencom.2012.03.004_bib0060_2
Nauflett
Characterization Subcommittee Safety Environmental Protection Subcommittee Joint Meeting, U.S.A., 1998
40.
R. E. Farncomb and G. W. Nauflett, US Patent 6177033, 2001.
41.
The nitrolysis of N,N-dialkylcarboxamides in liquid carbon dioxide
Kuchurov I.V., Fomenkov I.V., Zlotin S.G.
Russian Chemical Bulletin, 2010
42.
N. Chanhan, M.E. Colclough, J. Hamid, Proc. 6th Meeting on Supercritical Fluids, Nottingham, UK,;1; 1999.
43.
10.1016/j.mencom.2012.03.004_bib0070_2
Lobbecke
Proc. 7th Meeting on Supercritial Fluids, 2000
44.
Inorganic Syntheses , ed. L. F. Audrieth, McGraw-Hill, New York, 1950, vol. III, p. 78.
45.
10.1016/j.mencom.2012.03.004_bib0080
Fedorov
Izv. Akad. Nauk, Ser. Khim., 1997
47.
Infra-red spectra of nitric esters. Part 2.—Rotational isomerism of some esters
Urbański T., Witanowski M.
Transactions of the Faraday Society, 1963
49.
J. A. Riddick, W. B. Bunger, 20 Organic Solvents, 3rd edn., Interscience–Wiley, New York, 1970.
51.
Potency and In Vitro Tolerance of Organic Nitrates: Partially Denitrated Metabolites Contribute to the Tolerance-Devoid Activity of Pentaerythrityl Tetranitrate
Koenig A., Lange K., Konter J., Daiber A., Stalleicken D., Glusa E., Lehmann J.
Journal of Cardiovascular Pharmacology, 2007