Nitromethane
IUPAC name	nitromethane
Other names	nitrocarbol
Identifiers
CAS number	[75-52-5]
RTECS number	PA9800000
SMILES	C[N+]([O-])=O
Properties
Molecular formula	CH3NO2
Molar mass	61. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to Registry of Toxic Effects of Chemical Substances ( RTECS) is a Database of Toxicity information compiled from the open scientific literature without reference A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 04 g/mol
Appearance	colorless liquid
Density	1. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 138 g/cm³, liquid
Melting point	−29 °C (244. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. 15 K)
Boiling point	100–103 °C (373-376 K)
Solubility in water	ca. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. 10 g/100 mL
Acidity (pKa)	10. 2
Viscosity	0. Viscosity is a measure of the resistance of a Fluid which is being deformed by either Shear stress or Extensional stress. 61 mPa·s at 25 °C
Hazards
MSDS	External MSDS
MSDS	MainHazards = Flammable, harmful
NFPA 704	3 2 4
R-phrases	R5 R10 R22
S-phrases	S41
Flash point	35 °C
Related compounds
Related nitro compounds	nitroethane
Related compounds	methyl nitrite methyl nitrate
Supplementary data page
Structure and properties	n, εr, etc. A material safety data sheet ( MSDS) is a form containing data regarding the properties of a particular substance This page provides supplementary chemical data on Nitromethane A material safety data sheet ( MSDS) is a form containing data regarding the properties of a particular substance Symbolism The four divisions are typically color-coded with blue indicating level of Health Hazard, red indicating R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. The flash point of a flammable liquid is the lowest Temperature at which it can form an ignitable mixture in air Nitro compounds are Organic compounds that contain one or more nitro Functional groups (-2 Nitroethane is an organic compound having the chemical formula C2H5NO2 The Chemical compound methyl nitrite is an Alkyl nitrite made from Methanol. Methyl nitrate is the methyl Ester of Nitric acid and has the chemical formula CH3NO3 This page provides supplementary chemical data on Nitromethane This page provides supplementary chemical data on Nitromethane The refractive index (or index of Refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves is reduced inside the medium Measurement The relative static permittivity εr can be measured for static Electric fields as follows first the Capacitance of a test
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Nitromethane is an organic compound with the chemical formula CH₃NO₂. This page provides supplementary chemical data on Nitromethane This page provides supplementary chemical data on Nitromethane Ultraviolet-visible spectroscopy or ultraviolet-visible spectrophotometry ( UV/ VIS) involves the Spectroscopy of Photons in the UV-visible Infrared spectroscopy (IR spectroscopy is the subset of Spectroscopy that deals with the Infrared region of the Electromagnetic spectrum. Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy, is the name given to a technique which exploits the magnetic properties of certain nuclei Mass spectrometry is an analytical technique that identifies the chemical composition of a compound or sample based on the Mass-to-charge ratio of charged particles In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly An organic compound is any member of a large class of Chemical compounds whose Molecules contain Carbon. It is the simplest organic nitro compound. Nitro compounds are Organic compounds that contain one or more nitro Functional groups (-2 It is a slightly viscous, highly polar liquid commonly used as a solvent in a variety of industrial applications such as in extractions, as a reaction medium, and as a cleaning solvent. As an intermediate in organic synthesis, it is used widely in the manufacture of pharmaceuticals, pesticides, explosives, fibers, and coatings. Organic synthesis is a special branch of Chemical synthesis and is concerned with the construction of Organic compounds via Organic reactions Organic It is also used as a racing fuel.

Contents 1 Preparation 2 Uses 2.1 Derivatives 2.2 As an engine fuel 2.2.1 Explosive properties 3 Purification 4 See also 5 References 6 External links

Preparation

Nitromethane is produced industrially by treating propane with nitric acid at 350–450 °C. Nitric acid ( H[[nitrate NO3]] also known as Aqua fortis and spirit of nitre, is a highly corrosive and This exothermic reaction produces the four industrially significant nitroalkanes: nitromethane, nitroethane, 1-nitropropane, and 2-nitropropane. Nitroethane is an organic compound having the chemical formula C2H5NO2 The reaction involves free radicals, including the alkoxyl radicals of the type CH₃CH₂CH₂O^. , which arise via homolysis of the corresponding nitrite ester. Esters are a class of Chemical compounds and Functional groups Esters consist of an inorganic or organic Acid in which at least These alkoxy radicals are susceptible to C-C fragmentation reactions, which explains the formation of a mixture of products. ^[1]

Although inexpensively available, nitromethane can be prepared in other methods that are of instructional value. The reaction of sodium chloroacetate with sodium nitrite in aqueous solution produces this compound:

ClCH₂COONa + NaNO₂ + H₂O → CH₃NO₂ + NaCl + NaHCO₃

Nitromethane is distilled from the reaction and then dried over a mild desiccant. Chloroacetic acid is the Chemical compound with the formula ClCH2CO2H Sodium nitrite, with Chemical formula Na[[Nitrogen N]] O 2 is used as a Color fixative and Preservative in meats and ^[2]

Uses

The principal use of nitromethane is as a stabilizer for chlorinated solvents, which are used in dry cleaning, semiconductor processing, and degreasing. It is also used most effectively as a solvent or dissolving agent for acrylate monomers, such as cyanoacrylates (more commonly known as "super-glue"). A monomer (from Greek mono "one" and meros "part" is a small Molecule that may become chemically bonded to other ^[1]

Derivatives

In organic synthesis nitromethane is employed as a one carbon building block. Organic synthesis is a special branch of Chemical synthesis and is concerned with the construction of Organic compounds via Organic reactions Organic A synthon is a concept in Retrosynthetic analysis. It is defined as a structural unit within a Molecule which is related to a possible synthetic operation Its acidicity allows it to undergo deprotonation, enabling condensation reactions analogous to those of carbonyl compounds. Thus, under base catalysis, nitromethane adds to aldehydes in 1,2-addition in the nitroaldol reaction. An aldehyde is an organic compound containing a terminal Carbonyl group. The Nitroaldol reaction or Henry reaction is an aldol type reaction between an Aldehyde and Nitromethane. Some important derivatives include the pesticides Chloropicrin, Cl₃CNO₂ and tris(hydroxymethyl)nitromethane, (HOCH₂)₃CNO₂. Chloropicrin is a slightly oily colorless or faintly yellow liquid of the formula CCl3NO2 Reduction of the latter gives tris(hydroxymethyl)aminomethane, (CH₂OH)₃CNH₂, better known as “tris,” a widely used buffer. Tris is an abbreviation of the Organic compound known as tris(hydroxymethylaminomethane with the formula (HOCH23CNH2

In more specialized organic synthesis, nitromethane serve as a Michael donor, adding to α,β-unsaturated carbonyl compounds via 1,4-addition in the Michael reaction. Organic synthesis is a special branch of Chemical synthesis and is concerned with the construction of Organic compounds via Organic reactions Organic The Michael reaction or Michael addition is the Nucleophilic addition of a Carbanion to an alpha beta unsaturated carbonyl compound.

As an engine fuel

In a minor application, nitromethane is used as a fuel in racing, particularly drag racing, as well as for rockets and RC Models. Drag racing is a competition in which objects compete to be the first to cross a set finish mark usually from a dead stop and in a straight line A rocket or rocket vehicle is a Missile, Aircraft or other Vehicle which obtains Thrust by the reaction of the In car racing, nitromethane is commonly referred to as "nitro" or just "fuel". The oxygen content of nitromethane enables it to burn with much less atmospheric oxygen in comparison to hydrocarbons such as gasoline:

4CH₃NO₂ + 3O₂ → 4CO₂ + 6H₂O + 2N₂

14. Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the 6 kg of air is required to burn one kg of gasoline, but only 1. 7 kg of air for one kg of nitromethane. Since an engine’s cylinder can only contain a limited amount of air on each stroke, 8. 7 times more nitromethane than gasoline can be burned in one stroke. Nitromethane, however, has a lower energy density: Gasoline provides about 42–44 MJ/kg whereas nitromethane provides only 11. The joule (written in lower case ˈdʒuːl or /ˈdʒaʊl/ (symbol J) is the SI unit of Energy measuring heat, Electricity 3 MJ/kg.

Nitromethane can also be used as a monopropellant, i. Monopropellants are Propellants composed of chemicals or mixtures of chemicals which can be stored in a single container with some degree of safety e. , a fuel that burns without added oxygen. The following equation describes this process:

4 CH₃NO₂ → 4 CO + 4 H₂O + 2 H₂ + 2 N₂

Nitromethane has a laminar combustion velocity of approx. 0. 5 m/s, somewhat higher than gasoline, thus making it suitable for high speed engines. It also has a somewhat higher flame temperature of about 2400 °C. In the study of Combustion, there are two types of adiabatic flame temperature depending on how the process is completed constant volume and constant pressure The high heat of vaporisation of 0. 56 MJ/kg together with the high fuel flow provides significant cooling of the incoming charge (about twice that of methanol), resulting in reasonably low temperatures.

Nitromethane is usually used with rich air/fuel mixtures because it provides power even in the absence of atmospheric oxygen. Air-fuel ratio ( AFR) is the mass ratio of air to fuel present during combustion When rich air/fuel mixtures are used, hydrogen and carbon monoxide are two of the combustion products. These gases often ignite, sometimes spectacularly, as the normally very rich mixtures* of the still burning fuel exits the exhaust ports and out through the exhaust pipes. [* the very rich mixtures are necessary to reduce the temperature of combustion chamber hot parts so to control Pre-ignition and subsequent Detonation]

Note: The proceding three Paragraphs refer to conditions where the volume of Nitromethane blended with Methanol => 80%. And with a typical 500 cu. in. Drag Racing Engine producing now* in excess of 8000 HP. *Aug. 2007.

A small amount of hydrazine blended in nitromethane can increase the power output even further. Hydrazine is a Chemical compound with the formula N2H4 It has an Ammonia -like odor and is derived from the same industrial chemistry With nitromethane, hydrazine forms an explosive salt that is again a monopropellant. This unstable mixture poses a severe safety hazard.

In model aircraft and car glow fuel, the primary ingredient is generally methanol with some nitromethane (0% to 65%, but rarely over 30% since nitromethane is expensive compared to methanol) and 10–20% lubricants (usually castor oil and/or synthetic oil). Model aircraft are flying or non-flying models of existing or imaginary Aircraft, often scaled down versions of full size planes using materials such as balsa A model car is a miniature representation or Scale model, of an Automobile or similar powered vehicle generally reproducing the shapes of actually-produced Glow fuel is a generic term used to describe a Fuel source used by models -- generally the same or similar fuels can be used in model airplanes, Methanol, also known as methyl alcohol, carbinol, wood alcohol, wood naphtha or wood spirits, is a Chemical compound Castor oil is a Vegetable oil obtained from the Castor bean (technically castor seed as the castor plant Ricinus communis, is not a member of Synthetic oil is Oil consisting of Chemical compounds which were not originally present in Crude oil ( Petroleum) but were Artificially Even moderate amounts of nitromethane tend to increase the power created by the engine (as the limiting factor is often the air intake), making the engine easier to tune (adjust for the proper air/fuel ratio).

Explosive properties

Nitromethane was not known to be a high explosive until the 1950s when a railroad tanker car loaded with it exploded. An explosive material is a material that either is chemically or otherwise Energetically unstable or produces a sudden expansion of the material usually accompanied After much testing it was realized that nitromethane was a more energetic high explosive than TNT, although TNT has a higher velocity of detonation and brisance (shattering power against hard targets). Trinitrotoluene ( TNT) is a Chemical compound with the formula C6H2(NO23CH3 Brisance is a measure of the rapidity with which an Explosive develops its maximum Pressure. Both of these explosives are oxygen poor and some benefits are gained from mixing with an oxidizer, such as ammonium nitrate. An oxidizing agent or oxidising agent (also called an oxidant, oxidizer or oxidiser) can be defined as either a Chemical compound The Chemical compound ammonium nitrate, the Nitrate of Ammonia with the chemical formula N[[Hydrogen H]]4 N[[Oxygen O]]3 Pure nitromethane is an insensitive explosive with a VoD of approximately 6200 m/s, but even so inhibitors may be used to reduce the hazards. The tank car explosion was speculated to be due to adiabatic compression, a hazard common to all liquid explosives. This article covers adiabatic processes in Thermodynamics. For adiabatic processes in Quantum mechanics, see Adiabatic process (quantum mechanics This is when small entrained air bubbles compress and superheat with rapid rises in pressure. It was thought that an operator rapidly snapped shut a valve creating a 'hammer-lock' pressure surge. Water hammer (or more generally fluid hammer) is a Pressure surge or wave resulting when a fluid in motion is forced to stop or change direction suddenly (Momentum Nitromethane can be sensitized by adding a base to raise the pH. pH is the measure of the acidity or alkalinity of a Solution.

Nitromethane can also be mixed with ammonium nitrate, which is used as an oxidizer, to form an explosive mixture known as ANNM. The Chemical compound ammonium nitrate, the Nitrate of Ammonia with the chemical formula N[[Hydrogen H]]4 N[[Oxygen O]]3 An oxidizing agent or oxidising agent (also called an oxidant, oxidizer or oxidiser) can be defined as either a Chemical compound ANFO (or AN/FO, for ammonium nitrate / fuel oil) is a widely used Explosive mixture One graphic example of this was the use of nitromethane and ammonium nitrate on the Alfred P. Murrah Federal Building at Oklahoma City. The Alfred P Murrah Federal Building was a United States Federal Government complex located at 200 N Oklahoma City is the capital and largest city of the US state of Oklahoma.

Purification

Nitromethane is a popular solvent in organic and electroanalytical chemistry. It can be purified by cooling below its freezing point, washing the solid with cold diethyl ether, followed by distillation. Diethyl ether, also known as ether and ethoxyethane, is a clear colorless and highly Flammable liquid with a low Boiling point and a ^[3]

See also

• Adiabatic flame temperature, a thermodynamic calculation of the flame temperature of nitromethane

References

External links

• WebBook page for nitromethane

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