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CH3NO2.com is a site dedicated to Nitromethane in all it's glory. We're just starting to build the new site now, so keep on checking back to see the progress. Posted by Phil Luyer - High Octane Photos at 1:26 PM No comments: Email This BlogThis! Share to Twitter Share to Facebook Share to Pinterest.1,780 ch3no2 products are offered for sale by suppliers on Alibaba.com A wide variety of ch3no2 options are available to you, There are 216 suppliers who sells ch3no2 on Alibaba.com, mainly located in Asia. The top countries of supplier is China, from which the percentage of ch3no2 supply is 100% respectively.CH3NO2 Formula T-Shirt. $28.00. was . CH3NO2 Formula T-Shirt. $28.00. was . Share: Product Description / Details. Make your NHRA love show in this CH3NO2 t-shirt! Order yours today! Black; 100% Cotton; Left Chest/Full Back Screenprint; Size Chart. Men's T-Shirt Size Chart. S: M: L: XL: 2XL: 3XL: 4XL: 5XL: Chest: 34-37" 38-41"Search results for CH3NO2 at Sigma-Aldrich. Compare Products: Select up to 4 products. *Please select more than one item to compareNitromethane has the formula CH3NO2, with the N bonded to the C and without O-O bonds. Draw its two most important contributing structures. a. What is the hybridization of the C, and how many hybrid orbitals are in the molecule? b. What is the shortest bond? c. Between which two atoms is the strongest bond found? d.

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Solid nitromethane (CH3NO2) along with its isotopically labelled counterpart D3-nitromethane (CD3NO2) ices were exposed to Lyman α photons to investigate the mechanism involved in the decomposition of energetic materials in the condensed phase. The chemical processes in the ices were monitored onlin …Nitromethane, CH3NO2, is burned as a fuel; the (unbalanced) equation for the reaction is: CH3NO2(liquid) + O2 (gas) ---> Co2(gas) + N2(gas)+ H2O(gas) The standard enthalpy change of the reaction H°rxn for the balanced reaction with the lowest whole number coefficients is -1288.5kJ. If the H°f of CO2(gas) is -393.5kJ/mol and the H°f of H2O(gas) is .242 kJ/mol, calculate H°f for theFor the CH3NO2 Lewis structure, we have a total of 24 valence electrons. We'll form bonds between atoms, and each one of these bonds represents two electrons. We've used 12 valence electrons. And then we'll go around the outside of the Oxygens to fill their octets. So we have 12, 14, and 24 total valence electrons there.CH3NO2 The chemical formula of NITROMETHANE shown above is based on the molecular formula indicating the numbers of each type of atom in a molecule without structural information, which is different from the empirical formula which provides the numerical proportions of atoms of each type. The above chemical formula is the basis of stoichiometry

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The first resonance structure of nitromethane, CH3NO2, is shown. Determine the correct second resonance structure of nitromethane? asked by @marlont5 • 11 months ago • Chemistry → Resonance Structures. Comments. d Xin Li commented about 2 months agoWhat is the Hybridizations and Formal Charges of CH3NO2? Answer Save. 1 Answer. Relevance. Anonymous. 1 decade ago. Favorite Answer. This is nitromethane. The C is SP3 hybridized, an the N SP2. The formal charge on one of the O'2 is -1, and on the N is +1. Everything else has a formal charge of 0. 0 0.Nitromethane, sometimes shortened to just Nitro, is an organic compound with the chemical formula CH 3 NO 2.It is the simplest organic nitro compound.It is a 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.Nitromethane-or CH3NO2-is one member of a family of explosive compounds that contain nitrogen and oxygen. Remember the old safecracker crime movies where the "specialist" had to be real carefulMultiply that by the 9,500 btu's per lb of alcohol and our motor would be making 35,055btu's at 7000rpms. Nitromethane Nitromethane is a fuel that is used mostly in specialized drag racing classes such as "Top Fuel Funny Cars" . Nitromethane's chemical formula is CH3NO2.

Jump to navigation Jump to search Not to be confused with methyl nitrate or methyl nitrite. Nitromethane Names IUPAC name Nitromethane Preferred IUPAC name Nitromethane[1] Other names Nitrocarbol Identifiers CAS Number 75-52-5  3D model (JSmol) Interactive image ChEBI CHEBI:77701  ChEMBL ChEMBL276924  ChemSpider 6135  ECHA InfoCard 100.000.797 KEGG C19275  PubChem CID 6375 RTECS number PA9800000 UNII RU5WG8C3F4  CompTox Dashboard (EPA) DTXSID2020977 InChI InChI=1S/CH3NO2/c1-2(3)4/h1H3 Key: LYGJENNIWJXYER-UHFFFAOYSA-N InChI=1/CH3NO2/c1-2(3)4/h1H3Key: LYGJENNIWJXYER-UHFFFAOYAW SMILES C[N+](=O)[O-] Properties Chemical formula CH3NO2 Molar mass 61.04 g/mol Appearance colorless, oily liquid[2]Odor Light, fruity[2]Density 1.1371 g/cm3 (20 °C)[3]Melting point −28.7 °C (−19.7 °F; 244.5 K)[3] Boiling point 101.2 °C (214.2 °F; 374.3 K)[3] Critical point (T, P) 588 K, 6.0 MPa[4]Solubility in water ca. 10 g/100 mL Solubility miscible in diethyl ether, acetone, ethanol[3]Vapor pressure 28 mmHg (20 °C)[2]Acidity (pKa) 17.2 in DMSO; 10.21 in water[5][6]Magnetic susceptibility (χ) -21.0·10−6 cm3/mol[7]Thermal conductivity 0.204 W/(m·K) at 25 °C[8]Refractive index (nD) 1.3817 (20 °C)[3]Viscosity 0.63 cP at 25 °C[8]Dipole moment 3.46[9]Thermochemistry[10]Heat capacity (C) 106.6 J/(mol·K) Std molarentropy (So298) 171.8 J/(mol·K) Std enthalpy offormation (ΔfH⦵298) -112.6 kJ/mol Gibbs free energy (ΔfG˚) -14.4 kJ/mol Hazards Main hazards Flammable, health hazard Safety data sheet See: data page GHS pictograms GHS Signal word Danger GHS hazard statements H203, H226, H301, H331, H351 GHS precautionary statements P210, P261, P280, P304+340, P312, P370+378, P403+233 NFPA 704 (fire diamond) 2 3 3 Flash point 35[9] °C (95 °F; 308 K) Autoignitiontemperature 418[9] °C (784 °F; 691 K) Explosive limits 7–22%[9]Threshold limit value (TLV) 20 ppm[9]Lethal dose or concentration (LD, LC): LD50 (median dose) 940 mg/kg (oral, rat)950 mg/kg (oral, mouse)[11]LDLo (lowest published) 750 mg/kg (rabbit, oral)125 mg/kg (dog, oral)[11]LCLo (lowest published) 7087 ppm (mouse, 2 h)1000 ppm (monkey)2500 ppm (rabbit, 12 h)5000 ppm (rabbit, 6 h)[11]NIOSH (US health exposure limits): PEL (Permissible) TWA 100 ppm (250 mg/m3)[2]REL (Recommended) none[2]IDLH (Immediate danger) 750 ppm[2]Related compounds Related nitro compounds nitroethane Related compounds methyl nitritemethyl nitrate Supplementary data page Structure andproperties Refractive index (n),Dielectric constant (εr), etc. Thermodynamicdata Phase behavioursolid–liquid–gas Spectral data UV, IR, NMR, MS 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

Nitromethane, sometimes shortened to just Nitro, is an organic compound with the chemical formula CH3NO2. It is the simplest organic nitro compound. It is a 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.[12] Nitromethane is used as a fuel additive in various motorsports and hobbies, e.g. Top Fuel drag racing and miniature internal combustion engines in radio control, control line and free flight model aircraft.

Preparation

Nitromethane is produced industrially by combining propane and nitric acid in the gas phase at 350–450 °C (662–842 °F). This exothermic reaction produces the four industrially significant nitroalkanes: nitromethane, nitroethane, 1-nitropropane, and 2-nitropropane. The reaction involves free radicals, including the alkoxyl radicals of the type CH3CH2CH2O, which arise via homolysis of the corresponding nitrite ester. These alkoxy radicals are susceptible to C—C fragmentation reactions, which explains the formation of a mixture of products.[12]

Laboratory methods

It 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:[13]

ClCH2COONa + NaNO2 + H2O → CH3NO2 + NaCl + NaHCO3

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-glues").[12] It is also used as a fuel in some forms of racing. It can be used as an explosive, when gelled with several percent of gelling agent. This type of mixture is called PLX. Other mixtures include ANNM and ANNMAl – explosive mixtures of ammonium nitrate, nitromethane and aluminium powder.

As an organic solvent, it is considered to be highly polar (εr = 36 at 20 °C and μ = 3.5 Debye) but is aprotic and possesses very low Lewis basicity. Thus, it is a rare example of a polar solvent that is also weakly coordinating. This makes it useful for dissolving positively charged, strongly electrophilic species. However, its relatively high acidity and explosive properties (see below) limit its applications.

Reactions

Acid-base properties

Nitromethane is a relatively acidic carbon acid. It has a pKa of 17.2 in DMSO solution. This value indicates an aqueous pKa of about 11.[14] The reason of that being so acidic is due to the resonance structure below:

The anion is resonance stabilized

It is slow to deprotonate. Protonation of the conjugate base O2NCH2−, which is nearly isosteric with nitrate, occurs initially at oxygen.[15]

Organic reactions

In organic synthesis nitromethane is employed as a one carbon building block.[16][17] Its acidity 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. Some important derivatives include the pesticides chloropicrin (Cl3CNO2), beta-nitrostyrene, and tris(hydroxymethyl)nitromethane, ((HOCH2)3CNO2). Reduction of the latter gives tris(hydroxymethyl)aminomethane, (HOCH2)3CNH2, better known as tris, a widely used buffer. In more specialized organic synthesis, nitromethane serves as a Michael donor, adding to α,β-unsaturated carbonyl compounds via 1,4-addition in the Michael reaction.

As an engine fuel

Nitromethane is used as a fuel in motor racing, particularly drag racing, as well as for radio-controlled models[12] (such as cars, planes and helicopters). In this context, nitromethane is commonly referred to as "nitro", and is the principal ingredient for fuel used in the "Top Fuel" category of drag racing.

The oxygen content of nitromethane enables it to burn with much less atmospheric oxygen than conventional fuels. During nitromethane combustion nitric oxide (NO) is one of the major emission products along with CO2 and H2O.[18] Recent (2020) studies[19]suggest the correct stoichiometric equation for the burning of nitromethane is:

4 CH3NO2 + 5 O2 → 4 CO2 + 6 H2O + 4 NO

The amount of air required to burn 1 kg (2.2 lb) of gasoline is 14.7 kg (32 lb), but only 1.7 kg (3.7 lb) of air is required for 1 kg of nitromethane. Since an engine's cylinder can only contain a limited amount of air on each stroke, 8.6 times as much nitromethane as gasoline can be burned in one stroke. Nitromethane, however, has a lower specific energy: gasoline provides about 42–44 MJ/kg, whereas nitromethane provides only 11.3 MJ/kg. This analysis indicates that nitromethane generates about 2.3 times the power of gasoline when combined with a given amount of oxygen.

Nitromethane can also be used as a monopropellant, i.e., a fuel that burns without added oxygen. The following equation describes this process:

2 CH3NO2 → 2 CO + 2 H2O + H2 + N2

Nitromethane has a laminar combustion velocity of approximately 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 2,400 °C (4,350 °F). The high heat of vaporization 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. 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. Very rich mixtures are necessary to reduce the temperature of combustion chamber hot parts in order to control pre-ignition and subsequent detonation. Operational details depend on the particular mixture and engine characteristics.

A small amount of hydrazine blended in nitromethane can increase the power output even further. With nitromethane, hydrazine forms an explosive salt that is again a monopropellant. This unstable mixture poses a severe safety hazard and the Academy of Model Aeronautics does not permit its use in competitions.[20]

In model aircraft and car glow fuel, the primary ingredient is generally methanol with some nitromethane (0% to 65%, but rarely over 30%, and 10–20% lubricants (usually castor oil and/or synthetic oil). 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 a railroad tanker car loaded with it exploded on June 1, 1958.[21] After much testing, it was realized that nitromethane was a more energetic high explosive than TNT, although TNT has a higher velocity of detonation (VoD) and brisance. Both of these explosives are oxygen-poor, and some benefits are gained from mixing with an oxidizer, such as ammonium nitrate. Pure nitromethane is an insensitive explosive with a VoD of approximately 6,400 m/s (21,000 ft/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 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.

Nitromethane can also be mixed with ammonium nitrate, which is used as an oxidizer, to form an explosive mixture known as ANNM. One graphic example of this was the use of nitromethane and ammonium nitrate in the Oklahoma City bombing.

Nitromethane is used as a model explosive, along with TNT. It has several advantages as a model explosive over TNT, namely its uniform density and lack of solid post-detonation species that complicate the determination of equation of state and further calculations.

Nitromethane exhaust

Exhaust gas from an internal combustion engine whose fuel includes nitromethane will contain nitric acid vapour, which is corrosive, and when inhaled causes a muscular reaction making it impossible to breathe. The condensed nitric acid-based residue left over in a glow-fueled model engine after a model-flight session can also corrode their internal components, usually mandating use of a combination of kerosene to neutralize the residual nitric acid, and an "after-run oil" (often the lower-viscosity "air tool oil" variety of a popular preservative oil) for lubrication to safeguard against such damage, when such an engine is placed into storage.

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.[22]

See also

Top Fuel Adiabatic flame temperature, a thermodynamic calculation of the flame temperature of nitromethane Dinitromethane Model engine Trinitromethane Tetranitromethane RE factor

References

^ .mw-parser-output cite.citationfont-style:inherit.mw-parser-output .citation qquotes:"\"""\"""'""'".mw-parser-output .id-lock-free a,.mw-parser-output .citation .cs1-lock-free abackground:linear-gradient(transparent,transparent),url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat.mw-parser-output .id-lock-limited a,.mw-parser-output .id-lock-registration a,.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration abackground:linear-gradient(transparent,transparent),url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat.mw-parser-output .id-lock-subscription a,.mw-parser-output .citation .cs1-lock-subscription abackground:linear-gradient(transparent,transparent),url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registrationcolor:#555.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration spanborder-bottom:1px dotted;cursor:help.mw-parser-output .cs1-ws-icon abackground:linear-gradient(transparent,transparent),url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat.mw-parser-output code.cs1-codecolor:inherit;background:inherit;border:none;padding:inherit.mw-parser-output .cs1-hidden-errordisplay:none;font-size:100%.mw-parser-output .cs1-visible-errorfont-size:100%.mw-parser-output .cs1-maintdisplay:none;color:#33aa33;margin-left:0.3em.mw-parser-output .cs1-formatfont-size:95%.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-leftpadding-left:0.2em.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-rightpadding-right:0.2em.mw-parser-output .citation .mw-selflinkfont-weight:inherit"Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 662. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0457". National Institute for Occupational Safety and Health (NIOSH). ^ a b c d e Haynes, p. 3.414 ^ Haynes, p. 6.69 ^ Haynes, p. 5.94 ^ Reich, Hans. "Bordwell pKa table: "Nitroalkanes"". University of Wisconsin Chemistry Department. Retrieved 17 January 2016. ^ Haynes, p. 3.576 ^ a b Haynes, p. 6.231 ^ a b c d e Haynes, p. 15.19 ^ Haynes, p. 5.20 ^ a b c "Nitromethane". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH). ^ a b c d Markofsky, S. B. (2000). "Nitro Compounds, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_401.pub2. ISBN 978-3527306732. ^ Whitmore, F. C.; Whitmore, M. G. (1941). "Nitromethane". Organic Syntheses.; Collective Volume, 1, p. 401 ^ Bordwell, F. G.; Satish, A. V. (1994). "Is Resonance Important in Determining the Acidities of Weak Acids or the Homolytic Bond Dissociation Enthalpies (BDEs) of Their Acidic H-A Bonds?". Journal of the American Chemical Society. 116 (20): 8885–8889. doi:10.1021/ja00099a004. ^ Kramarz, K. W.; Norton, J. R. (2007). "Slow Proton-Transfer Reactions in Organometallic and Bioinorganic Chemistry". Progress in Inorganic Chemistry. pp. 1–65. doi:10.1002/9780470166437.ch1. ISBN 9780470166437. ^ Dauben, H. J. Jr.; Ringold, H. J.; Wade, R. H.; Pearson, D. L.; Anderson, A. G. Jr.; de Boer, T. J.; Backer, H. J. (1963). "Cycloheptanone". Organic Syntheses.; Collective Volume, 4, p. 221 ^ Noland, W. E. (1963). "2-Nitroethanol". Organic Syntheses.; Collective Volume, 4, p. 833 ^ Shrestha, Krishna Prasad; Vin, Nicolas; Herbinet, Olivier; Seidel, Lars; Battin-Leclerc, Frédérique; Zeuch, Thomas; Mauss, Fabian (2020-02-01). "Insights into nitromethane combustion from detailed kinetic modeling – Pyrolysis experiments in jet-stirred and flow reactors" (PDF). Fuel. 261: 116349. doi:10.1016/j.fuel.2019.116349. ISSN 0016-2361. ^ Shrestha, Krishna Prasad; Vin, Nicolas; Herbinet, Olivier; Seidel, Lars; Battin-Leclerc, Frédérique; Zeuch, Thomas; Mauss, Fabian (2020-02-01). "Insights into nitromethane combustion from detailed kinetic modeling – Pyrolysis experiments in jet-stirred and flow reactors" (PDF). Fuel. 261: 116349. doi:10.1016/j.fuel.2019.116349. ISSN 0016-2361. ^ "AMA Competition Regulations 2015–2016 Part 7. Fuels" (PDF). www.modelaircraft.org. Academy of Model Aeronautics. February 15, 2016. p. 24. Retrieved April 18, 2014. ^ Interstate Commerce Commission. "Accident Near Mt. Pulaski, ILL" (PDF). Ex Parte No 213. ^ Coetzee, J. F.; Chang, T.-H. (1986). "Recommended Methods for the Purification of Solvents and Tests for Impurities: Nitromethane" (PDF). Pure and Applied Chemistry. 58 (11): 1541–1545. doi:10.1351/pac198658111541.

Cited sources

Haynes, William M., ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). CRC Press. ISBN 978-1439855119.

External links

WebBook page for nitromethane History of Nitromethane CDC – NIOSH Pocket Guide to Chemical HazardsvteMotor fuelsFuel types Gasoline/petrol Diesel Biodiesel Biogasoline Lead Replacement Petrol Electricity Kerosene Compressed natural gas Hydrogen Ethanol Butanol fuel Racing fuel (Tetraethyllead)Fuel additives Butyl rubber Butylated hydroxytoluene 1,2-Dibromoethane 1,2-Dichloroethane Dimethyl methylphosphonate 2,4-Dimethyl-6-tert-butylphenol Dinonylnaphthylsulfonic acid 2,6-Di-tert-butylphenol Ecalene Ethylenediamine Metal deactivator Methyl tert-butyl ether Nitromethane Tetraethyllead TetranitromethaneFluids Motor oil Antifreeze Automatic transmission fluid Brake fluid Gear oil Windshield washer fluidRetail Fuel card Full service MTBE controversy Pay at the pump Authority control GND: 4253374-0 LCCN: sh98000189 MA: 2777327210 Retrieved from "https://en.wikipedia.org/w/index.php?title=Nitromethane&oldid=999365012"

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