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Methyl nitrate

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Not to be confused with nitromethane or methyl nitrite.

Methyl nitrate

Names

IUPAC name

Methyl nitrate

Other names

nitric acid methyl ester, nitrooxymethane

Identifiers

CAS Number  598-58-3 

3D model (JSmol)  Interactive image

ChemSpider  11231 

ECHA InfoCard 100.009.039 

PubChem CID  11724

UNII  LAD9RT85ES 
CompTox  DTXSID4073205 
Dashboard (EPA)

show

InChI

show

SMILES

Properties

Chemical formula CH3NO3

Molar mass 77.04 g/mol

Appearance Liquid

Density 1.203 g/cm3, liquid

Melting point −82.3 °C (−116.1 °F; 190.8 K)[1]

Boiling point 64.6 °C (148.3 °F; 337.8 K) (explodes)[1]

Explosive data

Shock sensitivity High [2]

Friction sensitivity High [2]

Detonation velocity 6300 m s−1 at ρ=1.217 g cm−3 [2]

Hazards

Main hazards Toxic, High Explosive

Except where otherwise noted, data are given for materials in


their standard state (at 25 °C [77 °F], 100 kPa).

 verify (what is   ?)

Infobox references

Methyl nitrate is the methyl ester of nitric acid and has the chemical formula CH3NO3. It


is a colourless volatile liquid that is explosive.

Contents

 1Synthesis
 2Explosive properties
 3Safety
 4History
 5Structure
 6References
 7External links

Synthesis[edit]
It can be produced by the condensation of nitric acid and methanol:[3]
CH3OH + HNO3 → CH3NO3 + H2O
A newer method uses methyl iodide and silver nitrate:[4]
CH3I + AgNO3 → CH3NO3 + AgI
Methyl nitrate can be produced on a laboratory or industrial
scale either through the distillation of a mixture of methanol
and nitric acid, or by the nitration of methanol by a mixture
of sulfuric and nitric acids. The first procedure is not
preferred due to the great explosion danger presented by
the methyl nitrate vapour. The second procedure is
essentially identical to that of making nitroglycerin.
However, the process is usually run at a slightly higher
temperature and the mixture is stirred mechanically on an
industrial scale instead of with compressed air.

Explosive properties[edit]
Methyl nitrate is a sensitive explosive. When ignited it
burns extremely fiercely with a gray-blue flame. Methyl
nitrate is a very strong explosive, like nitroglycerin, ethylene
glycol dinitrate, and other nitrate esters. The sensitivity of
methyl nitrate to initiation by detonation is among the
greatest known, with even a number one blasting cap, the
lowest power available, producing a near full detonation of
the explosive.[citation needed]
Despite the superior explosive properties of methyl nitrate,
it has not received application as an explosive due mostly
to its high volatility, which prevents it from being stored or
handled safely.

Safety[edit]
As well as being an explosive, methyl nitrate is toxic and
causes headaches when inhaled.

History[edit]
Methyl nitrate has not received much attention as an
explosive, but as a mixture containing 25% methanol it was
used as rocket fuel and volumetric explosive under the
name Myrol in Germany in World War II (during the Third
Reich). This mixture would evaporate at a constant rate
and so its composition would not change over time. It
presents a slight explosive danger (it is somewhat difficult
to detonate) and does not detonate easily via shock. [5][6]
According to A. Stettbacher, the substance was used as a
combustible during the Reichstag fire in 1933.[7] Gartz
shows in a recent work that only methyl nitrate with its
production and explosion potential can represent the
famous and mysterious "shooting water" from the German
Feuerwerkbuch (fireworks book) of about 1420 [8] (the oldest
technical text in German language, handwritten
in Dresden and later printed in Augsburg).[9]
The text in the fireworks book of 1420 is in extracts as
follows (ancient German):
"Wildu mit wasser schyessen // daß du kein pulfer prauch //
est vnd sterker und waiter // mit schewst dann als du daß
aller // pest pulfer hast das yemann gehab //
en mag und ye gemacht wurd so ny // salpeter und distillier
den mit wasser // vnd nym oleo benedicto dazu auch … //
… vnd zunt sie an mit sinnen das du davon kommen magst
… //
…mit disem wasser schewst du dreytousent schrit weit
… // … es ist gar köstlich…"
Translated:
Do you want to shoot with water // so that you don't need
powder // and stronger and further // you shoot than the
very // best powder somebody might have had ever // and
was made ever //
so take salpetre and distill it with water // and also take oleo
benedicto (the oil of Benedicus) // and ignit it with the
intention that you may get off
... with this water you will shoot threethousand foot // it is so
delicious

Structure[edit]
The structure of methyl nitrate has been studied
experimentally in the gas phase (combined gas-electron
diffraction and microwave spectroscopy, GED/MW) and in
the crystalline state (X-ray diffraction, XRD) (see Table 1).[4]

Gas phase structure of methyl nitrate determined by gas electron


diffraction

Solid-state structure of methyl nitrate determined by X-ray diffraction

In the solid state there are weak interactions between the O


and N atoms of different molecules (see figure).

Table 1: Structural parameters of methyl nitrate Bond lengths in Å , angles in °

Parameter

XRD GED/MW

C–O 1.451(1) 1.425(3)


N–OC 1.388(1) 1.403(2)

N–Oterminal 1.204(1) 1.205(1)

C–O–N 113.3(1) 113.6(3)

Oterminal-N-Oterminal 128.6(1) 131.4(4)

References[edit]
1. ^ Jump up to:    CRC Handbook of Chemistry and
a b

Physics (64th ed.). 1983. pp.  C–376.


2. ^ Jump up to:      Meyer, R.; Köhler, J.; Homberg, A.
a b c

(2007).  Explosives  (PDF)  (6th ed.). Wiley-VCH.


p. 212.  ISBN  978-3-527-31656-4.
3. ^ Black, A. P.; Babers, F. H. (1939).  "Methyl
nitrate". Organic Syntheses.  19: 64.; Collective
Volume, 2, p.  412
4. ^ Jump up to:a b Reichel, Marco; Krumm, Burkhard;
Vishnevskiy, Yury V.; Blomeyer, Sebastian;
Schwabedissen, Jan; Stammler, Hans‐Georg;
Karaghiosoff, Konstantin; Mitzel, Norbert W. (2019-12-
16).  "Solid‐State and Gas‐Phase Structures and
Energetic Properties of the Dangerous Methyl and
Fluoromethyl Nitrates".  Angewandte Chemie
International Edition.  58  (51): 18557–
18561. doi:10.1002/anie.201911300. ISSN 1433-7851. 
PMC  6916544.  PMID  31573130.
5. ^ Meyer, Rudolf (2008).  Explosivstoffe. Köhler, Josef.,
Homburg, Axel. (10., vollst. überarb. Aufl  ed.). Weinheim:
Wiley-VCH.  ISBN  978-3-527-32009-7. OCLC  24406897
1.
6. ^ Koch, Ernst-Christian (17 June 2019). Sprengstoffe,
Treibmittel, Pyrotechnika. Walter de Gruyter GmbH & Co.
KG (2. Auflage  ed.). Berlin. ISBN 978-3-11-055784-
8. OCLC  1107346317.
7. ^ Stettbacher, A. (1948).  Spreng- und Schießstoffe.
Rascher Verlag, Zürich.
8. ^ Gartz, Jochen (2007).  Vom griechischen Feuer zum
Dynamit  : eine Kulturgeschichte der Explosivstoffe .
Hamburg: E.S. Mittler & Sohn. ISBN 978-3-8132-0867-
2. OCLC  153884719.
9. ^ "www.feuerwerkbuch.de". www.feuerwerkbuch.de.
Retrieved 2020-06-15.
External links[edit]
 "Methyl nitrate". Webbook. NIST.
Categories: 
 Alkyl nitrates
 Explosive chemicals
 Liquid explosives
 Methyl esters
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Tetranitratoxycarbon
From Wikipedia, the free encyclopedia
Jump to navigationJump to search
  Carbon

  Oxygen

  Nitrogen

Names

Preferred IUPAC name


3,3′,3′′,3′′′-Methanetetrayltetra(2,4,5-trioxa-1-azabicyclo[1.1.1]pentane)

Other names

 Tetra(nitrato-O,O,O-methyl)methane

 Tetrakis(nitratoxycarbon)methane

 3,3',3'',3'''-Methanetrayltetrayltetrakis-2,4,5-trioxa-1-

azabicyclo[1.1.1]pentane[1]

Identifiers

CAS Number  1400582-42-4


3D model (JSmol)  Interactive image

PubChem CID  102449643

show

InChI

show

SMILES

Properties

Chemical formula C5N4O12

Molar mass 308.071 g·mol−1

Density 1.87 g/cm3 (predicted)[2]

Except where otherwise noted, data are given for materials in


their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tetranitratoxycarbon, systematic name tetra(nitrato-O,O,O-methyl)methane (often
shortened to tetrakis(nitratoxycarbon)methane),[3] is a hypothetical molecule that was
proposed by Clara Lazen, a fifth-grader in Kansas City, Missouri, who conceived of its
structure and built a model in 2012. She is credited as co-author of a scientific paper on
the molecule, which uses computational chemistry to predict that the molecule could
actually exist.

Contents

 1Prediction
 2Properties
 3Possible reactions
 4References
 5Further reading

Prediction[edit]
Science teacher Kenneth Boehr was using ball-and-stick models to represent simple
molecules during a fifth-grade class, when ten-year-old Clara Lazen [4] assembled a
complex model and asked whether it was a real molecule. [5] It is unclear if Lazen
randomly or deliberately assembled this particular molecule. [6]
Unsure if the molecule existed, Boehr sent a picture of the model to a chemist friend,
Robert Zoellner at Humboldt State University.[4][5] Zoellner checked the molecule against
the Chemical Abstracts database[4] and confirmed that Lazen's model was of a structural
type that had not been reported before.[5]
Zoellner wrote a paper on the molecule, published in Computational and Theoretical
Chemistry, crediting Lazen and Boehr as co-authors.[3]

Properties[edit]
Tetranitratoxycarbon consists of oxygen, nitrogen, and carbon, with molecular
structure C(CO
3N)

4. Its oxygen-rich formula, in particular, a positive oxygen balance, means it does not

require any external oxidizer to undergo complete oxidation, and thus may have
explosive other high-energy properties.[3] However, it is expected to be too thermally
unstable for practical use.[7]
The nitratoxycarbon functional group itself—a carbon atom and a nitrogen atom linked
by three oxygen-atom bridges—has yet to be observed in any chemical
compound. Computational chemistry studies indicate that it is only metastable, with
other structural isomers such as the carboxylic nitroso-ester (C(=O)ONO) being more
stable.[3] As such this functional group is likely to remain purely hypothetical and no
method for its synthesis has yet been proposed. However, several other elemental
variations have been synthesized[citation needed], including the all-carbon analog
(bicyclo[1.1.1]pentane).

Possible reactions[edit]
This section does not cite any sources. Please help improve this
section by adding citations to reliable sources. Unsourced material may be
challenged and removed. (February 2020)  (Learn how and when to remove
this template message)

Several reactions of tetranitratoxycarbon have been investigated computationally. For


example, one possible equation for its decomposition is:
C(CO3N)4 → 5 CO2 + O2 + 2 N2
that is predicted to have a standard enthalpy change of
−1326 kJ/mol based on bond-energy calculation methods.
Another potential reaction is its combustion in the presence
of oxygen:
C(CO3N)4 + O2 → 5 CO2 + 2 NO2 + N2
that is predicted to have a standard enthalpy change of
−1144 kJ/mol.

References[edit]
1. ^ CAS
2. ^ Buszek, Robert J.; Lindsay, C. Michael; Boatz,
Jerry A. (February 2013).
"Tetrakis(nitratoxycarbon)methane (Née CLL-1) as a
Potential Explosive Ingredient: a Theoretical
Study".  Propellants, Explosives,
Pyrotechnics. 38 (1): 9–
13.  doi:10.1002/prep.201200156.
3. ^ Jump up to:a b c d Zoellner, Robert W.; Lazen, Clara L.;
Boehr, Kenneth M. (2012). "A computational study of
novel nitratoxycarbon, nitritocarbonyl, and nitrate
compounds and their potential as high energy
materials". Computational and Theoretical
Chemistry.  979: 33–
37.  doi:10.1016/j.comptc.2011.10.011.
4. ^ Jump up to:a b c "Professor Confirms, Publishes 10-
year-old's New Molecule".  Humboldt State
Now. Humboldt University. Retrieved 3
February  2012.
5. ^ Jump up to:a b c "10-Year-Old Accidentally Creates New
Molecule in Science Class".  Popular Science.
Retrieved 3 February 2012.
6. ^ "Clara Lazen, Ten-Year-Old Fifth Grader,
Discovers New Molecule (VIDEO)". Huffington Post.
3 February 2012. Retrieved 28 February 2018.
7. ^ "Ten Year Old "discovers"
explosive". Explosci.com Now. Explosci.
Retrieved 20 March  2012.[dead link]

Further reading[edit]
G, Calvo, Luis; Rodolfo, Pumachagua
(2015). "Evaluación teórica de nuevos derivados
nitratoxicarbono de tetraedrano" [Theoretical evaluation
of new derivatives of the tetrahedrane
nitratoxycarbon]. Revista de la Sociedad Química del
Perú (in
Spanish). 81 (1). doi:10.37761/rsqp.v81i1.6. ISSN 181
0-634X. 
Categories: 
 Nitrates
 Hypothetical chemical compounds
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