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Nitroethane

Nitroethane is an organic compound with the chemical formula CH₃CH₂NO₂, classified as a nitroalkane where a nitro group (-NO₂) is attached to the ethyl chain.^[1] It appears as a colorless, oily liquid at standard temperature and pressure, exhibiting a mild, fruity odor, and is characterized by its density of 1.052 g/cm³, boiling point of 114.1 °C, and low solubility in water while being miscible with common organic solvents such as ethanol, methanol, and diethyl ether.^[1] Chemically, it acts as a mild oxidizer and can undergo reactions typical of nitro compounds, including reduction to amines and participation in condensation reactions.^[1] In industrial applications, nitroethane functions as a versatile solvent for polymers like polystyrene and for removing cyanoacrylate adhesives, as well as serving as a propellant and fuel additive in specialized formulations. In the United States, nitroethane is classified as a DEA List I chemical, subjecting its handling to regulatory oversight.^[1]^[2] It plays a key role as an intermediate in organic synthesis, particularly for introducing nitro groups into molecules used in the production of pharmaceuticals, agrochemicals, and other fine chemicals.^[1] Industrially, it is produced by the vapor-phase nitration of propane with nitric acid at high temperatures (350–450 °C), yielding nitroethane alongside other nitroparaffins.^[1] Safety considerations are critical due to its flammability (flash point of 28 °C) and potential to form explosive mixtures with air, as well as its ability to produce toxic nitrogen oxides upon decomposition.^[1] Exposure can irritate the skin, eyes, and respiratory tract, and inhalation or ingestion may lead to methemoglobinemia, central nervous system effects, and other systemic toxicities, with permissible exposure limits set at 100 ppm for an 8-hour time-weighted average.^[1]^[3] Proper handling requires ventilation, protective equipment, and avoidance of ignition sources to mitigate these hazards.^[1]

Properties

Physical properties

Nitroethane is an organic compound with the molecular formula C₂H₅NO₂ and a molecular weight of 75.05 g/mol.^[1] It appears as a colorless oily liquid at room temperature, exhibiting a mild, fruity odor.^[4]^[1] The compound has a boiling point of 114–116 °C at 760 mmHg and a melting point of −90 °C.^[5]^[1] Its density is 1.052 g/cm³ at 20 °C, and the refractive index is 1.391 at 20 °C.^[1]^[5] Nitroethane is miscible with organic solvents such as ethanol, diethyl ether, and acetone, but has limited solubility in water at 48 g/L (20 °C).^[1] The vapor pressure is approximately 15 mmHg at 20 °C, and the flash point is 28 °C (closed cup).^[1] Nitroethane remains stable under normal storage conditions but decomposes at temperatures above 177 °C.^[1]

Property	Value	Conditions	Source
Molecular formula	C₂H₅NO₂	-	PubChem
Molecular weight	75.05 g/mol	-	PubChem
Appearance	Colorless oily liquid	Room temperature	PubChem
Odor	Mild, fruity	-	CDC NIOSH
Boiling point	114–116 °C	760 mmHg	Sigma-Aldrich
Melting point	−90 °C	-	Sigma-Aldrich
Density	1.052 g/cm³	20 °C	PubChem
Refractive index	1.391	20 °C (D line)	Sigma-Aldrich
Water solubility	48 g/L	20 °C	PubChem
Vapor pressure	15 mmHg	20 °C	PubChem
Flash point	28 °C	Closed cup	PubChem
Decomposition temp.	>177 °C	-	PubChem

Chemical properties

Nitroethane has the structural formula CH₃CH₂NO₂, consisting of an ethyl group with the nitro group (-NO₂) attached to the alpha carbon, which imparts significant electron-withdrawing character to the molecule.^[1] The alpha hydrogens on the carbon adjacent to the nitro group are notably acidic, with a pKa of approximately 8.6, owing to the ability of the nitro group to stabilize the resulting nitronate anion through resonance delocalization of the negative charge.^[6] This enhanced acidity facilitates deprotonation to form the nitronate anion under mildly basic conditions.^[6] Due to the highly electronegative nitro group, nitroethane is a polar molecule with a dipole moment of about 3.5 D, contributing to its solvating properties and reactivity in polar media.^[7] In infrared spectroscopy, nitroethane displays characteristic absorptions for the nitro group at 1550–1350 cm⁻¹, arising from the asymmetric and symmetric stretching vibrations of the N-O bonds.^[8] The ¹H NMR spectrum features signals at δ 1.20 (triplet for CH₃) and δ 4.40 (quartet for CH₂), reflecting the deshielding effect of the nitro group on the alpha protons, while the ¹³C NMR shows peaks at δ ≈13 (CH₃) and δ ≈79 (CH₂).^[1]^[9] Nitroethane exhibits no significant tautomerism to an aci-nitro form, as the equilibrium strongly favors the nitro tautomer, though the nitro group itself engages in internal resonance between equivalent oxygen atoms.^[10] Nitroethane possesses explosive potential, particularly when forming mixtures with oxidizers or under conditions of shock or heat, but it is less sensitive to detonation than nitromethane.^[1]

Synthesis

Laboratory methods

One of the classical laboratory methods for synthesizing nitroethane is the Victor Meyer reaction, which involves the reaction of ethyl iodide with silver nitrite (AgNO₂) to produce nitroethane and ethyl nitrite as a byproduct.^[11] The reaction proceeds via nucleophilic substitution, where the silver salt promotes the formation of the nitro compound over the nitrite ester, though a mixture is typically obtained.^[11] The balanced equation is:

\text{CH}_3\text{CH}_2\text{I} + \text{AgNO}_2 \rightarrow \text{CH}_3\text{CH}_2\text{NO}_2 + \text{AgI}

This procedure is conducted under an inert atmosphere, such as nitrogen, to minimize side reactions from moisture or oxygen, with typical conditions involving stirring the reactants in an anhydrous ether solvent at room temperature for several hours.^[12] Yields for primary alkyl halides like ethyl iodide range from 50% to 70%, depending on purification efficiency and byproduct separation.^[11] An alternative laboratory route involves the direct nitration of ethane with gaseous nitric acid under controlled high-temperature conditions (around 400–700 K) in the vapor phase, which generates nitroethane alongside other nitroparaffins and oxidation products.^[13] This free-radical process, while conceptually simple, suffers from low selectivity and yields below 20% for nitroethane due to over-nitration and fragmentation.^[13] It is less favored in modern laboratory settings compared to halide-based methods. Purification of crude nitroethane from either route typically requires distillation under reduced pressure (boiling point approximately 115 °C at atmospheric pressure, lower under vacuum) to separate it from byproducts such as alkyl nitrites and unreacted halides.^[12] The distillate is collected between 50–60 °C at 20–30 mmHg, yielding a colorless liquid of high purity (>95%) after drying over a desiccant like calcium chloride.^[12] A modern adaptation of the nitrite displacement method employs sodium nitrite with an ethyl halide (e.g., ethyl bromide) in dimethyl sulfoxide (DMSO) as solvent, leveraging the high solubility of NaNO₂ in DMSO to drive the reaction at room temperature over 3–6 hours.^[12] This Kornblum modification reduces the need for silver salts and achieves yields of 50–70% for primary systems, though it remains less common than the traditional Victor Meyer approach due to similar byproduct issues.^[12] Note that the Henry reaction, which condenses nitroethane with aldehydes or ketones to form β-nitro alcohols, is a key application of nitroethane rather than a synthetic route to it and should not be confused with these preparative methods.^[11]

Industrial production

Nitroethane is primarily produced on an industrial scale through the vapor-phase nitration of propane using nitric acid, a process developed in the 1930s and first commercialized in the mid-20th century.^[14] The method originated from patents granted in 1934 for batch and continuous-flow nitration techniques, with Commercial Solvents Corporation (CSC) licensing the technology in 1935 and initiating commercial production shortly thereafter.^[14] Initially pursued as a route to higher nitroalkanes like 1-nitropropane and 2-nitropropane, the process yields nitroethane as a significant byproduct, reflecting its evolution during the 1940s and 1950s amid growing demand for nitroparaffin solvents and intermediates.^[15] In the primary industrial process, gaseous propane is reacted with nitric acid vapor at temperatures of 350–450 °C and pressures of 8–12 atm in specialized tubular reactors designed to handle the exothermic radical chain reaction. No catalyst is required, though the high temperatures necessitate robust, corrosion-resistant equipment to manage heat transfer and prevent side reactions.^[16] The reaction proceeds as an overview equation:

\mathrm{CH_3CH_2CH_3 + HNO_3 \rightarrow CH_3CH_2NO_2 + \text{byproducts}}

This yields a complex mixture of nitroparaffins, including approximately 10% nitroethane, alongside nitromethane (∼25%), 1-nitropropane (∼25%), and 2-nitropropane (∼40%), with unreacted hydrocarbons and oxidation products.^[17] Only 35–40% of the nitric acid typically converts to nitroparaffins, emphasizing the process's inefficiency but economic viability due to low-cost feedstocks.^[16] The crude mixture is quenched, washed to remove acids, and separated via fractional distillation, exploiting the boiling point differences (nitroethane at 114 °C, versus 101 °C for nitromethane and 122 °C for 1-nitropropane) to isolate pure nitroethane fractions. Current global production of nitroethane is estimated at around 6,500 metric tons annually as of 2023, with major output centered in the United States (via facilities like those operated by ANGUS Chemical, a successor to CSC) and China, which accounts for over 3,000 tons.^[18] This represents a portion of the broader mixed nitroparaffins produced yearly, estimated at approximately 65,000 tons as of 2023 based on the typical product distribution.^[18]^[17] An alternative approach involves direct vapor-phase nitration of ethane, which selectively forms nitroethane but suffers from lower overall yields and poorer selectivity due to competing oxidation pathways, rendering it less commercially viable than the propane route.^[13]

Applications

In organic synthesis

Nitroethane serves as a versatile nucleophile in the Henry (nitroaldol) reaction, where it undergoes deprotonation at the α-position to form a nitronate anion that adds to the carbonyl group of aldehydes or ketones, yielding β-nitro alcohols.^[19] The general reaction proceeds as follows:

\ce{CH3CH2NO2 + RCHO ->[base] RCH(OH)CH(NO2)CH3}

This C–C bond-forming process is catalyzed by metal-based systems such as lanthanide or zinc complexes, or organocatalysts, providing high yields of the addition products, which are valuable precursors for further transformations into amino alcohols or alkaloids.^[19] For instance, the reaction with aromatic aldehydes typically affords anti-selective adducts under copper catalysis, enhancing synthetic efficiency. The Nef reaction enables the conversion of nitroethane-derived nitro compounds, such as those from the Henry reaction, into corresponding carbonyl compounds under acidic conditions. For compounds bearing an ethyl nitro group (e.g., -CH(NO₂)CH₃), the mechanism involves initial deprotonation to a nitronate anion, followed by protonation to form a nitronic acid intermediate, which tautomerizes to a nitroso tautomer and hydrolyzes to the ketone (e.g., -CH₂C(O)CH₃) with release of nitrous oxide.^[20] This transformation is particularly useful for primary and secondary nitroalkanes derived from nitroethane, offering a mild alternative to oxidative methods with titanium or cerium reagents achieving near-quantitative yields. In pharmaceutical synthesis, nitroethane acts as a precursor for amino acid derivatives through reduction of the nitro group to ethylamine functionalities.^[21] For example, Henry reaction products from nitroethane and aldehydes can be reduced to β-amino alcohols, which serve as building blocks for chiral amino acids via Nef or direct hydrogenation.^[22] Historically, nitroethane has been employed in the synthesis of phenylnitroethane intermediates, such as 1-phenyl-2-nitropropene from benzaldehyde, which upon reduction yields amphetamine derivatives; this route, though regulated due to illicit applications, highlights its role in early 20th-century medicinal chemistry.^[23] Nitroethane functions as a carbon nucleophile in Michael additions to α,β-unsaturated carbonyl compounds, where the nitronate anion adds conjugate to the β-position, forming γ-nitro carbonyl adducts with potential for further elaboration.^[24] Catalyzed by fluoride on basic alumina or chiral phosphonates, these reactions exhibit stereoselectivity, often favoring syn diastereomers in asymmetric variants using cinchona alkaloid derivatives, with enantiomeric excesses exceeding 90% for cyclic enones.^[25] The stereocontrol arises from bifunctional activation of both the donor and acceptor, enabling applications in natural product synthesis.^[26] Reduction of nitroethane or its derivatives proceeds to oximes, hydroxylamines, or amines using established methods.^[21] Selective reduction to ethylhydroxylamine (CH₃CH₂NHOH) is achieved with zinc in ammonium chloride or catalytic hydrogenation over Raney nickel at mild pressures, yielding up to 80% with minimal over-reduction.^[27] Full conversion to ethylamine derivatives employs Zn/HCl or Pd/C-mediated hydrogenation, providing primary amines in high purity for peptide or alkaloid assembly.^[28] Post-2000 developments in asymmetric synthesis have leveraged chiral catalysts for the Henry reaction of nitroethane, achieving high enantioselectivity in β-nitro alcohol formation.^[19] Copper-bis(sulfonamide) complexes or recyclable heterogeneous catalysts, such as Cu-Schiff base on silica, promote additions to aldehydes with ee values over 95%, favoring anti products through bidentate coordination of the nitronate and carbonyl.^[29] These advancements, including bifunctional thioureas, have expanded nitroethane's utility in enantiopure pharmaceutical intermediates.^[30]

Industrial and other uses

Nitroethane serves as an effective solvent in various industrial applications due to its polarity and ability to dissolve a range of organic materials. It is particularly valued for dissolving nitrocellulose, cyanoacrylate adhesives, and styrene polymers, making it suitable for use in paints, inks, and coatings where it enhances solvency for resins such as acrylic and vinyl types.^[1]^[31] Additionally, nitroethane acts as a solvent for cellulose esters, alkyd resins, waxes, fats, and dyestuffs, contributing to its role in formulating high-performance coatings for sectors like aerospace and marine applications.^[1]^[18] In the fuels sector, nitroethane functions as a fuel additive, leveraging its oxygenate properties to improve combustion efficiency in specialized applications. It is incorporated into racing fuels and model engines, often in blends with nitromethane at concentrations of 5–20% to enhance power output while providing inherent oxygen for more complete burning.^[1] This additive role extends to experimental liquid propellants, where nitroethane supports higher energy release in internal combustion processes.^[1] Nitroethane also finds use as a propellant in aerosol formulations and as a chemical intermediate for explosives, though its application in the latter is restricted by regulations. In aerosol products, it aids in stabilization and dispersion, similar to related nitro compounds.^[1] As an intermediate, it contributes to the production of nitroplasticizers for solid propellants in military contexts.^[1] Other niche applications include its role as an extraction solvent for certain alkaloids and in perfume manufacturing to impart fruity notes, drawing on its inherent fruity odor. Historically, nitroethane has been explored as a component in rocket fuels.^[1] The global nitroethane market, valued at approximately USD 188 million in 2023, sees a significant portion allocated to solvent and fuel uses, with projections estimating growth to USD 314 million by 2032 driven by demand in coatings and additives.^[32] In the United States, nitroethane is classified as a DEA List I chemical (code 6724) due to its potential misuse as a precursor in illicit drug synthesis, subjecting it to strict reporting and threshold regulations for importation, exportation, and distribution.^[1]^[33]

Safety and environmental considerations

Health effects and toxicity

Nitroethane's primary toxicity arises from its metabolism to nitrite ion following inhalation or ingestion, which oxidizes the ferrous iron (Fe²⁺) in hemoglobin to ferric iron (Fe³⁺), forming methemoglobin and impairing oxygen transport.^[34] This methemoglobinemia manifests as cyanosis, headache, and dyspnea, with severe cases leading to tissue hypoxia.^[34] Acute exposure to nitroethane produces moderate toxicity, with an oral LD50 of 1,100 mg/kg in rats and an inhalation LC50 greater than 2,200 ppm for 6 hours in rats. Dermal exposure causes skin irritation but shows low systemic absorption due to limited penetration.^[34] Chronic exposure to nitroethane may result in liver damage, as evidenced by minimal histological changes and increased liver weights in rats after repeated inhalation at concentrations around 100 ppm for 13 weeks. Kidney effects have been observed at higher concentrations.^[34] Animal studies indicate no reproductive toxicity or teratogenic effects at tested doses.^[35] A notable case of nitroethane poisoning occurred in 1994 when a child ingested an artificial fingernail remover containing the compound, resulting in severe methemoglobinemia that was successfully treated with intravenous methylene blue.^[36] No widespread human epidemics from nitroethane exposure have been reported. Nitroethane has not been classified by the International Agency for Research on Cancer (IARC) and shows negative results in genotoxicity assays, including the Ames test.^[34] Occupational exposure limits for nitroethane include an OSHA permissible exposure limit (PEL) of 100 ppm as an 8-hour time-weighted average (TWA) and an ACGIH threshold limit value (TLV) of 100 ppm TWA.^[37]

Handling and environmental impact

Nitroethane should be stored in tightly closed containers in a cool, dry, well-ventilated area away from sources of ignition, heat, sparks, and open flames, as it is a flammable liquid with a flash point of 28°C.^[38] It is incompatible with strong oxidizing agents, strong acids, and strong bases, which can lead to violent reactions or formation of shock-sensitive compounds.^[35] Handling requires explosion-proof equipment and grounding to prevent static discharge, and operations should be conducted in a fume hood to minimize vapor exposure.^[39] In the event of a spill, responders should evacuate the area, ventilate thoroughly, and avoid ignition sources before containing the liquid with absorbent materials such as sand or vermiculite.^[40] The absorbed material should be collected in suitable containers for disposal, and the area decontaminated with water if safe. Personal protective equipment (PPE) including chemical-resistant gloves, safety goggles, and a respirator with organic vapor cartridges is essential during cleanup to prevent skin contact, eye irritation, or inhalation.^[1] Nitroethane is classified as a flammable liquid under UN 2842 and is subject to international transport regulations.^[41] In the European Union, it is registered under REACH with registration number 01-2119966158-27-XXXX.^[42] In the United States, it is listed on the TSCA inventory as an active chemical substance. In the United States, it is also regulated as a List I chemical by the Drug Enforcement Administration (DEA) under the Controlled Substances Act, requiring registration for manufacturers, distributors, and importers due to its role as a precursor in the synthesis of methamphetamine.^[2]^[1] Due to its potential use as a precursor in explosives and pharmaceuticals, export controls apply in various countries under dual-use regulations.^[43] In the environment, nitroethane exhibits low persistence under aerobic conditions, with limited data indicating potential biodegradation, though it is not classified as readily biodegradable (less than 10% degradation in 28 days per OECD 301D).^[42] Its octanol-water partition coefficient (log Kow) is approximately 0.16, suggesting low bioaccumulation potential (BCF of 1 in fish).^[42] Spills can pose a risk as a groundwater contaminant due to its moderate solubility in water (about 48 g/L at 20°C) and potential for leaching.^[1] Ecologically, nitroethane is harmful to aquatic life, with an LC50 for zebrafish (Danio rerio) of 880 mg/L over 48 hours.^[39] Combustion of nitroethane can release nitrogen oxides (NOx), contributing to air pollution and acid rain formation.^[44] Waste nitroethane should be managed as hazardous waste through incineration in facilities equipped with scrubbers to control NOx emissions, particularly for large quantities.^[44] Solvent recovery processes can enable recycling where feasible, reducing environmental release.^[45]

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