Nitroglycerin
- Formula: C3H5N3O9
- Molecular weight: 227.0865
- IUPAC Standard InChI: InChI=1S/C3H5N3O9/c7-4(8)13-1-3(15-6(11)12)2-14-5(9)10/h3H,1-2H2
- IUPAC Standard InChIKey: SNIOPGDIGTZGOP-UHFFFAOYSA-N
- CAS Registry Number: 55-63-0
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: 1,2,3-Propanetriol, trinitrate; Angibid; Anginine; Angiolingual; Angorin; Blasting gelatin; Blasting oil; Cardamist; Gilucor nitro; Glonoin; Glycerin trinitrate; Glycerol trinitrate; Glyceryl nitrate; Glyceryl trinitrate; GTN; Klavikordal; Lenitral; Myoglycerin; Niglin; Niglycon; Nitora; Nitrine-TDC; Nitro-lent; Nitro-Span; Nitroglycerine; Nitroglycerol; Nitroglyn; Nitrolan; Nitroletten; Nitrolingual; Nitrolowe; Nitromel; Nitrong; Nitrorectal; Nitroretard; Nitrostabilin; Nitrostat; Nitrozell retard; Nysconitrine; NG; NTG; Perglottal; Propanetriol Trinitrate; S.N.G.; Soup; SNG; Temponitrin; Trinalgon; Trinitrin; Trinitroglycerin; Trinitroglycerol; Trinitrol; Vasoglyn; 1,2,3-Propanetriyl Nitrate; Glycerol, nitric acid triester; Glyceroltrinitraat; Glycerol(trinitrate de); Myocon; Niong; Nitric acid triester of glycerol; Nitrin; Nitrine; Nitro-Dur; Nitroglicerina; Nitrogliceryna; Nitroglycerine, spirit of; Nitroglycerin, spirits of; Nitrol; Nitronet; NK-843; RCRA Waste number P081; SK-106N; Solution glyceryl trinitrate; Spirit of glonoin; Spirit of glyceryl trinitrate; Spirit of trinitroglycerin; Spirits of nitroglycerin; TNG; Deponit; Nitro-Bid; Nitrocine; Nitrodisc; Nitrogard; Nitrolingual Spray; Susadrin; Transderm-Nitro TTS; Tridil; Adesitrin; Aquo-trinitrosan; Corangil; Cordipatch; Corditrine; Coro-nitro; Glonoine oil; Nitro-PRN; Nitro Mack; Nitrolande; Nitrolar; Nitromex; Nitronal; Nitrosigma; Percutol; Perlinganit; Reminitrol; Suscard; Sustac; Sustonit; Sutonit; Transderm-nitro; Transiderm-nitro; Trinitrosan; 1,2,3-Propanetriol, 1,2,3-trinitrate; Solinitrina; Triniplas; Nitroderm; Nitrofortin; Nitroglin; Epinitril; Chitamite
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -66.71 ± 0.65 | kcal/mol | Ccb | Miroshnichenko, Korchatova, et al., 1988 | see Miroshnichenko, Korchatova, et al., 1985 |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -88.4 ± 0.5 | kcal/mol | Eqk | Kazakov, Kirpichev, et al., 1990 | Heat of nitration |
| ΔfH°liquid | -88.70 ± 0.41 | kcal/mol | Ccb | Miroshnichenko, Korchatova, et al., 1988 | see Miroshnichenko, Korchatova, et al., 1985 |
| ΔfH°liquid | -89.6 | kcal/mol | Ccb | Handrick, 1956 | Naval Powder Factory, 1951 |
| ΔfH°liquid | -89.0 ± 0.9 | kcal/mol | Ccb | Taylor and Hall, 1947 | Heat of combustion corrected for pressure |
| ΔfH°liquid | -84.58 | kcal/mol | Ccb | Rinkenbach, 1926 | Author's h288_condensed=-81.70 kcal/mol |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -365. ± 3. | kcal/mol | AVG | N/A | Average of 7 values; Individual data points |
Phase change data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔvapH° | 22.0 ± 0.50 | kcal/mol | C | Miroshnichenko, Korchatova, et al., 1988 | see Miroshnichenko, Korchatova, et al., 1985; ALS |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 24.98 | 308. | A | Stephenson and Malanowski, 1987 | Based on data from 293. to 373. K.; AC |
| 14.0 | 415. | N/A | Stull, 1947 | Based on data from 400. to 524. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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| Temperature (K) | A | B | C | Reference | Comment |
|---|---|---|---|---|---|
| 400. to 524. | 4.07017 | 2508.448 | -39.235 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
| ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 5.227 | 285.5 | Acree, 1991 | AC |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
+
=
+
By formula: C3H6N2O7 + HNO3 = C3H5N3O9 + H2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -1.4 ± 0.3 | kcal/mol | Eqk | Kazakov, Kirpichev, et al., 1990 | liquid phase; Heat of nitration |
| ΔrH° | -1.3 ± 0.3 | kcal/mol | Cm | Kazakov, Lagodzinskaya, et al., 1989 | liquid phase |
+
=
+
By formula: C3H6N2O7 + HNO3 = C3H5N3O9 + H2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -2.5 ± 0.3 | kcal/mol | Eqk | Kazakov, Kirpichev, et al., 1990 | liquid phase; Heat of nitration |
+ 2
=
+ 2
By formula: C3H7NO5 + 2HNO3 = C3H5N3O9 + 2H2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -4.2 ± 0.3 | kcal/mol | Cm | Kazakov, Lagodzinskaya, et al., 1989 | liquid phase |
+ 3
=
+ 3
By formula: C3H8O3 + 3HNO3 = C3H5N3O9 + 3H2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -8.7 ± 0.4 | kcal/mol | Cm | Kazakov, Lagodzinskaya, et al., 1989 | liquid phase |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
| Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| Origin | AAFS Toxicology Section MS DB Committee, U. Alberta, Canada |
| NIST MS number | 246295 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | DB-5 | 140. | 1364.54 | Hobbs and Conde, 1992 | 30. m/0.25 mm/0.25 μm |
| Capillary | DB-5 | 140. | 1372.91 | Hobbs and Conde, 1992 | 30. m/0.25 mm/0.25 μm |
Kovats' RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Packed | OV-101 | 1387. | Alley and Dykes, 1972 | 6. K/min; Tstart: 70. C; Tend: 220. C |
Kovats' RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Methyl Silicone | 1356. | Staples, 2005 | Column diameter: 0.25 mm; Program: not specified |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 1356.07 | Hobbs and Conde, 1992 | 30. m/0.25 mm/0.25 μm, 5. K/min; Tstart: 40. C; Tend: 300. C |
| Capillary | DB-5 | 1366.09 | Hobbs and Conde, 1992 | 30. m/0.25 mm/0.25 μm, 5. K/min; Tstart: 40. C; Tend: 300. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 1356. | Staples, 2004 | He; Program: not specified |
| Capillary | DB-5 | 1361. | Staples, 2004 | He; Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Miroshnichenko, Korchatova, et al., 1988
Miroshnichenko, E.A.; Korchatova, L.I.; Shelaputina, V.P.; Zyuz'kevich, S.A.; Lebedev, Yu.A.,
Thermochemistry of glyceryl trinitrate,
Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988, 1778-1781. [all data]
Miroshnichenko, Korchatova, et al., 1985
Miroshnichenko, E.A.; Korchatova, L.I.; Shelaputina, V.P.; Zyuzkevich, S.A.; Lebedev, Yu.A.,
Thermochemistry of glyceryl trinitrate,
Bull. Acad. Sci. USSR, Div. Chem. Sci., 1985, 1778-1781. [all data]
Kazakov, Kirpichev, et al., 1990
Kazakov, A.I.; Kirpichev, E.P.; Lagodzinskaya, G.V.; Andrienko, L.P.; Yunda, N.G.; Korolev, A.M.; Rubstov, Yu.I.; Manelis, G.B.; Eremenko, L.T.,
Study of nitration equilibrium in the glycerin-aqueous nitric acid system. 2. Changes in ΔH and ΔS in the nitration reaction,
Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, 1565-1570. [all data]
Handrick, 1956
Handrick, G.R.,
Report of the study of pure explosive compounds. Part IV. Calculation of heat of combustion of organic compounds from structural features and calculation of power of high explosives, Rpt. C-58247 for the Office of the Chief of Ordnance, contract DA-19-020-ORD-47 by the Arthur D. Little, Inc., Cambridge, MA, 1956, 467-573. [all data]
Taylor and Hall, 1947
Taylor, J.; Hall, C.R.L.,
Determination of the heat of combustion of nitroglycerin and the thermochemical constants of nitrocellulose,
J. Phys. Chem., 1947, 51, 593-611. [all data]
Rinkenbach, 1926
Rinkenbach, W.H.,
The properties of glycol dinitrate,
Ind. Eng. Chem., 1926, 18, 1195-1197. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [all data]
Kazakov, Lagodzinskaya, et al., 1989
Kazakov, A.I.; Lagodzinskaya, E.P.; Kirpichev, E.P.; Andrienko, L.P.; Yunda, N.G.; Korolev, A.M.; Robtsov, Yu.I.; Manelis, G.V.; Eremenko, L.T.,
Thermodynamics of nitration of glycerol,
Dokl. Phys. Chem. (Engl. Transl.), 1989, 305, 287-291. [all data]
Hobbs and Conde, 1992
Hobbs, J.R.; Conde, E.P.,
Gas chromatographic retention indices of explosives and nitro-compounds
in Advances in Analysis and Detection of Explosives: Proceedings of the 4th International Symposium on Analysis of Detection of Explosives, September 7-10, 1992, Jerusalem Israel, J. Yinon, ed(s)., Kluwer Academic Publishers, Netherlands, 1992, 153-164. [all data]
Alley and Dykes, 1972
Alley, B.J.; Dykes, H.W.H.,
Gas-Liquid Chromatographic Determination of Nitrate Esters,Stabilizers and Plasticizers in Nitrocellulose-Base Propellants,
J. Chromatogr., 1972, 71, 1, 23-37, https://doi.org/10.1016/S0021-9673(01)85687-9
. [all data]
Staples, 2005
Staples, E.J.,
Ultrahigh-speed chromatography and virtual chemical sensors for detecting explosives and chemical warfare agents,
IEEE Sens. J., 2005, 5, 4, 622-631, https://doi.org/10.1109/JSEN.2005.850990
. [all data]
Staples, 2004
Staples, E.J.,
Analysis of odors from explosives using an electronic nose, 2004, retrieved from http://www.estcal.com/TechPapers/OdorsofExplosives.doc. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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