Nitromethane

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Nitromethane
Structural formula of nitromethane Valence structural formula of nitromethane.svg
Structural formula of nitromethane
Nitromethane Nitromethane-3D-vdW.png
Nitromethane
Names
IUPAC name
Nitromethane
Preferred IUPAC name
Nitromethane [1]
Other names
Nitrocarbol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.797 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
RTECS number
  • PA9800000
UNII
  • InChI=1S/CH3NO2/c1-2(3)4/h1H3 Yes check.svgY
    Key: LYGJENNIWJXYER-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/CH3NO2/c1-2(3)4/h1H3
    Key: LYGJENNIWJXYER-UHFFFAOYAW
  • C[N+](=O)[O-]
Properties
CH3NO2
Molar mass 61.04 g/mol
Appearancecolorless, 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]
ca. 10 g/100 mL
Solubility miscible in diethyl ether, acetone, ethanol, methanol [3]
Vapor pressure 28 mmHg (20 °C) [2]
Acidity (pKa)
  • 10.21 (H2O) [5]
  • 17.2 (DMSO) [6]
-21.0·10−6 cm3/mol [7]
Thermal conductivity 0.204 W/(m·K) at 25 °C [8]
1.3817 (20 °C) [3]
Viscosity 0.63 cP at 25 °C [8]
3.46 [9]
Explosive data
Shock sensitivity Low
Friction sensitivity Low
Detonation velocity 6400 m/s
Thermochemistry [10]
106.6 J/(mol·K)
Std molar
entropy (S⦵298)
171.8 J/(mol·K)
-112.6 kJ/mol
-14.4 kJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable, health hazard
GHS labelling:
GHS-pictogram-explos.svg GHS-pictogram-flamme.svg GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg
Danger
H203, H226, H301, H331, H351
P210, P261, P280, P304+P340, P312, P370+P378, P403+P233
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazards (white): no code
2
3
3
Flash point 35 [9]  °C (95 °F; 308 K)
418 [9]  °C (784 °F; 691 K)
Explosive limits 7–22% [9]
20 ppm [9]
Lethal dose or concentration (LD, LC):
940 mg/kg (oral, rat)
950 mg/kg (oral, mouse) [11]
750 mg/kg (rabbit, oral)
125 mg/kg (dog, oral) [11]
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
nitroethane
Related compounds
 methyl nitrite
methyl nitrate
Supplementary data page
Nitromethane (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Nitromethane, sometimes shortened to simply "nitro", is an organic compound with the chemical formula CH
3NO
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. As an intermediate in organic synthesis, it is used widely in the manufacture of 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.

Contents

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 dominant use of the nitromethane is as a precursor reagent. A major derivative is chloropicrin (CCl3NO2), a widely used pesticide. It condenses with formaldehyde (Henry reaction) to eventually give tris(hydroxymethyl)aminomethane ("tris"), a widely used buffer and ingredient in alkyd resins. [12]

Solvent and stabilizer

The major application is as a stabilizer in chlorinated solvents. As an organic solvent, nitromethane has an unusual combination of properties: highly polar (εr = 36 at 20 °C and μ = 3.5 Debye) but aprotic and weakly basic. This combination makes it useful for dissolving positively charged, strongly electrophilic species. It is a solvent for acrylate monomers, such as cyanoacrylates (more commonly known as "super-glues"). [12]

Fuel

Although a minor application in terms of volume, [12] nitromethane also is used as a fuel or fuel additive for sports and hobby. For some application, it is mixed with methanol in racing cars, boats, and model engines.

Nitromethane is used as a fuel in motor racing, particularly drag racing, as well as for radio-controlled model power boats, cars, planes and helicopters. In this context, nitromethane is commonly referred to as "nitro fuel" or simply "nitro", and is the principal ingredient for fuel used in the "Top Fuel" category of drag racing. [14]

The oxygen content of nitromethane enables it to burn with much less atmospheric oxygen than conventional fuels. [15] During nitromethane combustion, nitric oxide (NO) is one of the major emission products along with CO2 and H2O. [16] Nitric oxide contributes to air pollution, acid rain, and ozone layer depletion. Recent (2020) studies [17] 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.[ citation needed ] This analysis indicates that nitromethane generates about 2.3 times the power of gasoline when combined with a given amount of oxygen.[ citation needed ]

Nitromethane can also be used as a monopropellant, i.e., a propellant that decomposes to release energy without added oxygen. It was first tested as rocket monopropellant in 1930s by Luigi Crocco  [ it ] fom Italian Rocket Society. [18] [19] There is a renewed interest in nitromethane as safer replacement of hydrazine monopropellant. [20] 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.[ citation needed ]

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.[ citation needed ]

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. The National Hot Rod Association and Academy of Model Aeronautics do not permit its use in competitions. [21]

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).

Former uses

It formerly was used in the explosives industry as a component in a binary explosive formulation with ammonium nitrate and in shaped charges, and it was used as a chemical stabilizer to prevent decomposition of various halogenated hydrocarbons. [22] It is also used as a fuel in some forms of racing.

Other

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.

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. [23] It is so acidic because the anion admits an alternate, stabilizing resonance structure:

Nitromethane anion resonance.jpg

The acid deprotonates only slowly. Protonation of the conjugate base O2NCH2−, which is nearly isosteric with nitrate, occurs initially at oxygen. [24]

Organic reactions

In organic synthesis nitromethane is employed as a one carbon building block. [25] [26] 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.

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. [27]

Safety

Nitromethane has a modest acute toxicity. LD50 (oral, rats) is 1210±322 mg/kg. [12]

Nitromethane is "reasonably anticipated to be a human carcinogen" according to a U.S. government report. [28]

Explosive properties

Nitromethane was not known to be a high explosive until a railroad tank car loaded with it exploded on June 1, 1958. [29] After much testing[ citation needed ], it was realized that nitromethane was a more energetic high explosive than TNT [ citation needed ], although TNT has a higher velocity of detonation (VoD) and brisance [ citation needed ]. 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[ citation needed ] 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.[ citation needed ]

If mixed with ammonium nitrate, which is used as an oxidizer, it forms an explosive mixture known as ANNM.

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 reacts with solutions of sodium hydroxide or methoxide in alcohol to produce an insoluble salt of nitromethane. This substance is a sensitive explosive which reverts to nitromethane under acidic conditions and decomposes in water to form another explosive compound, sodium methazonate, which has a reddish-brown color:

2 CH3NO2 + NaOH → HON=CHCH=NO2Na + 2 H2O

Nitromethane's reaction with solid sodium hydroxide is hypergolic.

See also

Related Research Articles

<span class="mw-page-title-main">Hydrogen peroxide</span> Chemical compound

Hydrogen peroxide is a chemical compound with the formula H2O2. In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution in water for consumer use and in higher concentrations for industrial use. Concentrated hydrogen peroxide, or "high-test peroxide", decomposes explosively when heated and has been used as both a monopropellant and an oxidizer in rocketry.

<span class="mw-page-title-main">Nitric acid</span> Highly corrosive mineral acid

Nitric acid is the inorganic compound with the formula HNO3. It is a highly corrosive mineral acid. The compound is colorless, but samples tend to acquire a yellow cast over time due to decomposition into oxides of nitrogen. Most commercially available nitric acid has a concentration of 68% in water. When the solution contains more than 86% HNO3, it is referred to as fuming nitric acid. Depending on the amount of nitrogen dioxide present, fuming nitric acid is further characterized as red fuming nitric acid at concentrations above 86%, or white fuming nitric acid at concentrations above 95%.

<span class="mw-page-title-main">TNT</span> Impact-resistant high explosive

Trinitrotoluene, more commonly known as TNT (and more specifically 2,4,6-trinitrotoluene), and by its preferred IUPAC name 2-methyl-1,3,5-trinitrobenzene, is a chemical compound with the formula C6H2(NO2)3CH3. TNT is occasionally used as a reagent in chemical synthesis, but it is best known as an explosive material with convenient handling properties. The explosive yield of TNT is considered to be the standard comparative convention of bombs and asteroid impacts. In chemistry, TNT is used to generate charge transfer salts.

<span class="mw-page-title-main">Toluene</span> Chemical compound

Toluene, also known as toluol, is a substituted aromatic hydrocarbon with the chemical formula C6H5CH3, often abbreviated as PhCH3, where Ph stands for phenyl group. It is a colorless, water-insoluble liquid with the odor associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) attached to a phenyl group by a single bond. As such, its systematic IUPAC name is methylbenzene. Toluene is predominantly used as an industrial feedstock and a solvent.

<span class="mw-page-title-main">Ammonium perchlorate</span> Chemical compound

Ammonium perchlorate ("AP") is an inorganic compound with the formula NH4ClO4. It is a colorless or white solid that is soluble in water. It is a powerful oxidizer. Combined with a fuel, it can be used as a rocket propellant called ammonium perchlorate composite propellant. Its instability has involved it in a number of accidents, such as the PEPCON disaster.

<span class="mw-page-title-main">Hydrazine</span> Colorless flammable liquid with an ammonia-like odor

Hydrazine is an inorganic compound with the chemical formula N2H4. It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. Hydrazine is highly hazardous unless handled in solution as, for example, hydrazine hydrate.

<span class="mw-page-title-main">Oxidizing agent</span> Chemical compound used to oxidize another substance in a chemical reaction

An oxidizing agent is a substance in a redox chemical reaction that gains or "accepts"/"receives" an electron from a reducing agent. In other words, an oxidizer is any substance that oxidizes another substance. The oxidation state, which describes the degree of loss of electrons, of the oxidizer decreases while that of the reductant increases; this is expressed by saying that oxidizers "undergo reduction" and "are reduced" while reducers "undergo oxidation" and "are oxidized". Common oxidizing agents are oxygen, hydrogen peroxide, and the halogens.

<span class="mw-page-title-main">Nitrogen dioxide</span> Chemical compound with formula NO₂

Nitrogen dioxide is a chemical compound with the formula NO2. One of several nitrogen oxides, nitrogen dioxide is a reddish-brown gas. It is a paramagnetic, bent molecule with C2v point group symmetry. Industrially, NO2 is an intermediate in the synthesis of nitric acid, millions of tons of which are produced each year, primarily for the production of fertilizers.

<span class="mw-page-title-main">Nitrobenzene</span> Chemical compound

Nitrobenzene is an aromatic nitro compound and the simplest of the nitrobenzenes, with the chemical formula C6H5NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from benzene as a precursor to aniline. In the laboratory, it is occasionally used as a solvent, especially for electrophilic reagents.

<span class="mw-page-title-main">Nitration</span> Chemical reaction which adds a nitro (–NO₂) group onto a molecule

In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters between alcohols and nitric acid. The difference between the resulting molecular structures of nitro compounds and nitrates is that the nitrogen atom in nitro compounds is directly bonded to a non-oxygen atom, whereas in nitrate esters, the nitrogen is bonded to an oxygen atom that in turn usually is bonded to a carbon atom.

<span class="mw-page-title-main">Nitro compound</span> Organic compound containing an −NO₂ group

In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups. The nitro group is one of the most common explosophores used globally. The nitro group is also strongly electron-withdrawing. Because of this property, C−H bonds alpha (adjacent) to the nitro group can be acidic. For similar reasons, the presence of nitro groups in aromatic compounds retards electrophilic aromatic substitution but facilitates nucleophilic aromatic substitution. Nitro groups are rarely found in nature. They are almost invariably produced by nitration reactions starting with nitric acid.

<span class="mw-page-title-main">Methyl nitrite</span> Chemical compound

Methyl nitrite is an organic compound with the chemical formula CH
3ONO. It is a gas, and is the simplest alkyl nitrite.

<span class="mw-page-title-main">Guanidine nitrate</span> Chemical compound

Guanidine nitrate is the chemical compound with the formula [C(NH2)3]NO3. It is a colorless, water-soluble salt. It is produced on a large scale and finds use as precursor for nitroguanidine, fuel in pyrotechnics and gas generators. Its correct name is guanidinium nitrate, but the colloquial term guanidine nitrate is widely used.

<span class="mw-page-title-main">Vanadium(V) oxide</span> Precursor to vanadium alloys and industrial catalyst

Vanadium(V) oxide (vanadia) is the inorganic compound with the formula V2O5. Commonly known as vanadium pentoxide, it is a brown/yellow solid, although when freshly precipitated from aqueous solution, its colour is deep orange. Because of its high oxidation state, it is both an amphoteric oxide and an oxidizing agent. From the industrial perspective, it is the most important compound of vanadium, being the principal precursor to alloys of vanadium and is a widely used industrial catalyst.

<span class="mw-page-title-main">Methyl nitrate</span> Chemical compound

Methyl nitrate is the methyl ester of nitric acid and has the chemical formula CH3NO3. It is a colourless explosive volatile liquid.

<span class="mw-page-title-main">Ethylenediamine</span> Chemical compound

Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.

<span class="mw-page-title-main">Nitroethane</span> Chemical compound

Nitroethane is an organic compound having the chemical formula C2H5NO2. Similar in many regards to nitromethane, nitroethane is an oily liquid at standard temperature and pressure. Pure nitroethane is colorless and has a fruity odor.

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References

  1. ↑ "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 (inactive 2024-04-14). ISBN   978-0-85404-182-4.{{cite book}}: CS1 maint: DOI inactive as of April 2024 (link)
  2. 1 2 3 4 5 6 NIOSH Pocket Guide to Chemical Hazards. "#0457". National Institute for Occupational Safety and Health (NIOSH).
  3. 1 2 3 4 5 Haynes, p. 3.414
  4. ↑ Haynes, p. 6.69
  5. ↑ Haynes, p. 5.94
  6. ↑ Reich, Hans. "Bordwell pKa table: "Nitroalkanes"". University of Wisconsin Chemistry Department. Retrieved 27 January 2022.
  7. ↑ Haynes, p. 3.576
  8. 1 2 Haynes, p. 6.231
  9. 1 2 3 4 5 Haynes, p. 15.19
  10. ↑ Haynes, p. 5.20
  11. 1 2 3 "Nitromethane". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  12. 1 2 3 4 5 6 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.
  13. ↑ Whitmore, F. C.; Whitmore, M. G. (1941). "Nitromethane". Organic Syntheses ; Collected Volumes, vol. 1, p. 401.
  14. ↑ Carley, Larry (2013-01-06). "HPBG: The Power of Racing Fuels". Engine Builder Magazine. Retrieved 2024-05-31.
  15. ↑ "What is Nitro Methane Fuel: Understanding High-Performance Racing's Power Source - Ran When Parked - Car, Vehicle & Truck Guides and Repair Journals". ranwhenparked.net. 2024-03-05. Retrieved 2024-05-31.
  16. ↑ 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. Bibcode:2020Fuel..26116349S. doi:10.1016/j.fuel.2019.116349. ISSN   0016-2361. S2CID   208755285.
  17. ↑ 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. Bibcode:2020Fuel..26116349S. doi:10.1016/j.fuel.2019.116349. ISSN   0016-2361. S2CID   208755285.
  18. ↑ Boyer, E.; Kuo, K. (January 2006). Characteristics of Nitromethane for Propulsion Applications. 44th AIAA Aerospace Sciences Meeting and Exhibit. Reno, NV. doi:10.2514/6.2006-361. ISBN   978-1-62410-039-0. AIAA 2006-361.
  19. ↑ Clark, J. D.; Asimov, Isaac (1972). Ignition! an informal history of liquid rocket propellants . Rutgers University Press. pp.  9-10. ISBN   978-0-8135-0725-5.
  20. ↑ Kurilov, Maxim; Werling, Lukas; Kirchberger, Christoph (2023). Nitromethane as a Green Propellant: First Results of a Combustion Test Campaign (PDF). Aerospace Europe Conference 2023. doi: 10.13009/EUCASS2023-372 .
  21. ↑ "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.
  22. ↑ SABIC, Cas AardenGraduate University of Groningen Worked as a chemist in companies such as Wilmar Oleochemicals B. Vand. "Nitromethane: An Ultimate Guide to Properties, Uses and Synthesis". Safrole. Retrieved 2024-05-31.
  23. ↑ 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.
  24. ↑ 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.
  25. ↑ 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 ; Collected Volumes, vol. 4, p. 221.
  26. ↑ Noland, W. E. (1963). "2-Nitroethanol". Organic Syntheses ; Collected Volumes, vol. 4, p. 833.
  27. ↑ 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. S2CID   95631774.
  28. ↑ "National Toxicology Program 15th Report on Carcinogens" (PDF). National Toxicology Program U.S. Department of Health and Human Services. December 21, 2021. Archived (PDF) from the original on October 2, 2023. Retrieved May 30, 2024.
  29. ↑ Interstate Commerce Commission. "Accident Near Mt. Pulaski, ILL" (PDF). Ex Parte No 213. Archived from the original (PDF) on 1 November 2020.

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