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Acetonitrile

Acetonitrile is a colorless, volatile, and flammable liquid organic compound with the chemical formula CH₃CN (or C₂H₃N) and a molecular weight of 41.05 g/mol, known for its ether-like or aromatic odor and high solubility in water and most organic solvents.^[1] It has a boiling point of 81.6°C (179°F), a melting point of -45.4°C (-49°F), a density of 0.786 g/cm³ at 20°C, and a flash point of 5.5°C (42°F), making it less dense than water but capable of forming explosive vapors when heated.^[2] Primarily produced as a byproduct of acrylonitrile manufacturing through processes like the ammoxidation of propylene, acetonitrile serves as a key industrial chemical with an annual global production exceeding 200,000 metric tons.^[3] As a polar aprotic solvent, acetonitrile is extensively used in organic synthesis, pharmaceutical manufacturing, and high-performance liquid chromatography (HPLC) due to its ability to dissolve a wide range of compounds without donating protons.^[1] It plays a critical role in the production of pharmaceuticals, agrochemicals, dyes, plastics, and batteries, including lithium-ion batteries, as well as in the extraction of hydrocarbons and the separation of fatty acids from vegetable oils.^[3] Additionally, it is employed in the manufacture of photographic films, perfumes, rubber products, and pesticides, and historically as a rodenticide and alcohol denaturant.^[4] Despite its utility, acetonitrile is toxic and poses significant health and safety risks; it is harmful if swallowed, inhaled, or absorbed through the skin, with an odor threshold of 170 ppm, and metabolizes in the body to hydrogen cyanide, potentially causing central nervous system depression, respiratory failure, and cyanide poisoning.^[3] It reacts violently with strong oxidizing agents and requires careful handling in well-ventilated areas to mitigate fire and explosion hazards from its low flash point and vapor density greater than air.^[5] Environmentally, acetonitrile enters the atmosphere primarily from automobile exhaust and industrial emissions, where it can persist but is biodegradable under aerobic conditions.^[3]

Properties

Molecular structure

Acetonitrile has the chemical formula CH₃CN and a molecular weight of 41.05 g/mol.^[1] The molecule adopts a linear structure along its C-C≡N backbone, with the methyl carbon bonded to three hydrogen atoms in a tetrahedral arrangement. The C-C bond length is approximately 1.46 Å, the C≡N triple bond length is approximately 1.16 Å, and the bond angles around the cyano group are approximately 180°, consistent with the sp hybridization of the cyano carbon.^[6]^[7] The carbon atom in the methyl group (CH₃-) is sp³ hybridized, forming four sigma bonds: three C-H bonds and one C-C bond. In contrast, the cyano carbon is sp hybridized, utilizing two sp hybrid orbitals to form sigma bonds with the methyl carbon and nitrogen, while the remaining p orbitals form the pi bonds of the triple bond with nitrogen. The nitrogen atom is also sp hybridized, with its lone pair occupying an sp orbital.^[8] This electronic arrangement results in a significant dipole moment of 3.92 D, primarily arising from the electronegative nitrogen atom pulling electron density toward itself in the polar C≡N bond.^[9] The Lewis structure of acetonitrile is represented as H₃C–C≡N, where the cyano carbon shares one single bond with the methyl group and a triple bond with nitrogen; the nitrogen bears a lone pair of electrons. The nitrile group exhibits resonance, with two major contributing structures that delocalize the electron density:

\chemfig{H_3C-C#N: <-> H_3C-C^{+}=[::60]N^{-}}

This resonance stabilizes the molecule and enhances the polarity of the C≡N bond, with the cyano carbon bearing a partial positive charge and the nitrogen a partial negative charge.^[10]

Physical properties

Acetonitrile is a colorless liquid at room temperature, exhibiting a faint ether-like odor due to trace impurities or its inherent chemical nature. Its boiling point is 81.6 °C at standard atmospheric pressure, while the melting point is -45.4 °C, indicating a relatively wide liquid range suitable for various laboratory and industrial applications. The density of acetonitrile is 0.786 g/cm³ at 20 °C, which is lower than that of water, contributing to its utility as a less dense solvent. The refractive index of acetonitrile is 1.344 at 20 °C, a value that reflects its optical properties in spectroscopic analyses. Its viscosity is 0.34 cP at 25 °C, making it a low-viscosity fluid that flows easily. Additionally, the vapor pressure is 73 mmHg at 20 °C, and the heat of vaporization is 29.75 kJ/mol, parameters that influence its volatility and evaporation behavior in open systems. Thermodynamic properties include a molar heat capacity of 91.7 J/mol·K for the liquid phase at 25 °C, which describes its capacity to store thermal energy.

Property	Value	Conditions	Source
Appearance	Colorless liquid, ether-like odor	Room temperature	PubChem
Boiling point	81.6 °C	1 atm	NIST
Melting point	-45.4 °C	-	NIST
Density	0.786 g/cm³	20 °C	NIST
Refractive index	1.344	20 °C	NIST
Viscosity	0.34 cP	25 °C	NIST
Vapor pressure	73 mmHg	20 °C	NIST
Heat of vaporization	29.75 kJ/mol	Boiling point	NIST
Molar heat capacity (liquid)	91.7 J/mol·K	25 °C	NIST

Chemical properties

Acetonitrile features a nitrile functional group (-C≡N), which is characterized by a triple bond between carbon and nitrogen, enabling it to undergo nucleophilic addition reactions due to the electrophilic nature of the carbon atom in the cyano group.^[10] A prominent example is the hydrolysis of acetonitrile under acidic conditions, where it reacts with water in the presence of sulfuric acid to yield acetic acid and ammonium sulfate:

\text{CH}_3\text{CN} + 2\text{H}_2\text{O} + \text{H}_2\text{SO}_4 \rightarrow \text{CH}_3\text{COOH} + \text{NH}_4\text{HSO}_4

This reaction proceeds via initial addition of water to form an amide intermediate, followed by further hydrolysis, highlighting the reactivity of the nitrile group toward nucleophiles.^[11] Acetonitrile exhibits considerable chemical stability, particularly resistance to oxidation under standard conditions, which contributes to its utility in various chemical environments.^[12] However, it is susceptible to hydrolysis in the presence of strong acids or bases, converting to acetamide or acetic acid depending on the conditions, as the triple bond is cleaved by nucleophilic attack. The pKa of its conjugate acid (CH₃CNH⁺) is approximately -10, indicating that acetonitrile is a very weak base and protonation occurs only under highly acidic conditions.^[13] In coordination chemistry, acetonitrile serves as a ligand in transition metal complexes, coordinating through the lone pair on the nitrogen atom of the cyano group to form stable bonds with metal centers. This behavior is observed in various complexes, such as those with ruthenium or tungsten, where the nitrile ligand can be substituted or reduced while bound to the metal.^[14] Acetonitrile lacks geometric isomers due to its linear structure and simple molecular framework, with no possibility for cis-trans configurations. Tautomeric forms, such as potential imine-like structures, are negligible under normal conditions, as the energy barrier for such interconversions is prohibitively high in this aliphatic nitrile.^[10] Spectroscopically, acetonitrile is readily identified by characteristic signals from the nitrile group. In infrared (IR) spectroscopy, the C≡N stretching vibration appears as a sharp, intense peak at approximately 2250 cm⁻¹, a hallmark of the triple bond.^[15] In nuclear magnetic resonance (NMR) spectroscopy, the ¹H NMR spectrum shows a singlet at 2.0 ppm for the methyl protons, reflecting their equivalent environment. The ¹³C NMR spectrum displays signals at 1.3 ppm for the CH₃ carbon and 118.3 ppm for the CN carbon, with the latter shifted downfield due to the electronegativity of the nitrogen.^[16]^[17]

Production

Industrial synthesis

Acetonitrile is predominantly produced on an industrial scale as a byproduct of acrylonitrile manufacturing through the ammoxidation of propylene, a process developed by the Standard Oil Company of Ohio (Sohio) in the 1950s and now widely adopted globally. In this method, propylene reacts with ammonia and oxygen over a metal oxide catalyst, typically bismuth phosphomolybdate, at temperatures of 400–500°C to yield acrylonitrile as the main product, alongside water and byproducts including acetonitrile and hydrogen cyanide. The overall reaction for acrylonitrile formation is CH₃CH=CH₂ + NH₃ + ³/₂ O₂ → CH₂=CHCN + 3 H₂O, with acetonitrile formed via parallel pathways involving partial oxidation and cyanation, resulting in co-production yields of 40–60 kg of acetonitrile per metric ton of acrylonitrile, equivalent to approximately 4–6% by weight. This integrated process accounts for over 90% of global acetonitrile supply, tying its availability closely to the ~7 million metric tons annual production of acrylonitrile for polymers and fibers.^[18] Historically, prior to the dominance of the Sohio process, acetonitrile was synthesized through the dehydration of acetamide, an amide derived from acetic acid and ammonia. The reaction, CH₃CONH₂ → CH₃CN + H₂O, was facilitated industrially using dehydrating agents such as acetic anhydride or catalytic supports like alumina at elevated temperatures around 300–400°C. This method, employed in the mid-20th century, offered a dedicated route independent of acrylonitrile production but was less economical due to higher raw material costs and energy demands, leading to its decline as the ammoxidation byproduct became the preferred source.^[19] Following extraction from the reaction mixture via absorption and quenching, crude acetonitrile undergoes multi-stage purification primarily through distillation to remove water, acrylonitrile, and other impurities. Azeotropic or pressure-swing distillation is commonly used to break the acetonitrile-water azeotrope, achieving final purities exceeding 99.9% suitable for solvent applications. Global annual production of acetonitrile stands at approximately 200,000 metric tons as of the 2020s, with major producers in Asia and North America scaling output in line with acrylonitrile demand.^[20]^[21] A significant supply disruption occurred during 2008–2009, when reduced acrylonitrile production capacity—driven by the global economic crisis lowering demand for downstream products like synthetic fibers—combined with plant maintenance issues and temporary shutdowns in key facilities, particularly in China and the US, led to a sharp acetonitrile shortage. This event caused prices to escalate dramatically from about $1.50 per kg to peaks of $25 per kg, impacting pharmaceutical and analytical sectors reliant on the solvent and prompting temporary shifts to alternatives or recycling methods.^[22]^[23]

Laboratory preparation

In laboratory settings, acetonitrile is commonly prepared by the dehydration of acetamide using strong dehydrating agents such as phosphorus pentoxide (P₂O₅) or thionyl chloride (SOCl₂). The reaction involves heating acetamide with P₂O₅, which removes the elements of water from the amide group to form the nitrile:

\ce{CH3CONH2 + P2O5 -> CH3CN + HPO3 + ...}

This method is straightforward and suitable for small-scale synthesis, producing acetonitrile in good yields after isolation.^[24]^[25] Another approach starts with the reaction of acetyl chloride with ammonia to form acetamide as an intermediate, followed by dehydration to acetonitrile. The initial step is the nucleophilic acyl substitution where ammonia attacks the carbonyl carbon of acetyl chloride, yielding acetamide and ammonium chloride:

\ce{CH3COCl + NH3 -> CH3CONH2 + NH4Cl}

The acetamide is then dehydrated using P₂O₅ or SOCl₂ as described above, ultimately affording acetonitrile via the loss of water. This two-step process allows for controlled preparation in educational or research laboratories.^[25] A less common laboratory method involves the catalytic reaction of ethanol with ammonia, typically promoted by metal catalysts such as cobalt-nickel, to produce acetonitrile, water, and hydrogen:

\ce{CH3CH2OH + NH3 -> CH3CN + H2O + 2 H2}

This dehydrogenative amination process is more specialized for research applications.^[26] Across these methods, yields typically range from 70% to 90%, depending on reaction conditions and scale. The crude product is purified by distillation under reduced pressure (boiling point approximately 82°C at atmospheric pressure, lower under vacuum) to minimize decomposition and remove impurities like water or unreacted starting materials.^[27]

Applications

Solvent uses

Acetonitrile is widely used as a polar aprotic solvent in organic synthesis and analytical chemistry, characterized by its high dielectric constant of 37.5 at 20°C, which facilitates the dissolution of many ionic salts while avoiding strong solvation of anions through hydrogen bonding. This property enhances the nucleophilicity of anionic species, making it ideal for SN2 reactions, such as the displacement of alkyl halides by nucleophiles, where polar aprotic solvents like acetonitrile accelerate the reaction rate compared to protic alternatives.^[28] In high-performance liquid chromatography (HPLC), acetonitrile serves as a key mobile phase component for reverse-phase separations, valued for its transparency in the UV region down to 190 nm, low viscosity that supports high flow rates, and compatibility with aqueous buffers.^[29] Its eluotropic strength and miscibility with water enable efficient gradient elution for analyzing pharmaceuticals, biomolecules, and environmental samples. Acetonitrile functions as an entrainer in extractive distillation processes to separate azeotropic mixtures, such as benzene-cyclohexane, by selectively altering the relative volatilities of components through liquid-liquid equilibria interactions.^[30] This application leverages its polarity to preferentially solvate aromatic compounds, facilitating industrial-scale purification of hydrocarbon streams.^[31] In electrochemistry, acetonitrile is incorporated into non-aqueous electrolytes for lithium-ion batteries, typically with lithium salts like LiPF₆, due to its low viscosity (0.34 cP), high ionic conductivity (up to 35 mS/cm in formulations), and wide electrochemical stability window exceeding 4 V.^[32] These attributes support fast-charging capabilities and operation across a broad temperature range, as demonstrated in ternary solvent systems including carbonates.^[33] Acetonitrile also plays a role in peptide synthesis, particularly in solid-phase methods, where its full miscibility with water aids in resin swelling and washing steps, while its aprotic nature promotes efficient coupling of hindered amino acids without side reactions.^[34] It serves as a greener alternative to DMF in Fmoc-based protocols, yielding high-purity peptides comparable to or exceeding traditional solvents.^[35]

Other industrial applications

Acetonitrile serves as a key extractive solvent in the petroleum refining industry for the purification of 1,3-butadiene from crude C4 hydrocarbon streams obtained via steam cracking. In this process, known as extractive distillation, acetonitrile's high selectivity and polarity allow it to preferentially dissolve 1,3-butadiene while separating it from less polar components such as n-butane, isobutane, and butenes, enabling the production of high-purity butadiene for synthetic rubber and other polymer applications. This method is widely adopted in industrial plants, including those in China, due to its efficiency and compatibility with existing infrastructure.^[36]^[37] Beyond extraction, acetonitrile functions as a chemical intermediate and reagent in the synthesis of various pharmaceuticals and agrochemicals. It participates in reactions to form nitrogen-containing compounds, such as amides and heterocycles, which are building blocks for active pharmaceutical ingredients, including certain antidiabetic and antiviral drugs. For instance, acetonitrile can be incorporated into molecular frameworks through Ritter-type reactions or as a nitrile source in multi-component syntheses, contributing to the development of complex therapeutic agents. Its role as a reactant enhances reaction efficiency in electrochemical and catalytic processes tailored for pharmaceutical production.^[38]^[39] In analytical chemistry, acetonitrile is employed as a reagent in mass spectrometry workflows, particularly for the desalting and enrichment of biomolecules. A common application involves acetonitrile precipitation to selectively remove high-molecular-weight proteins and salts from complex biological samples like serum, allowing for the isolation and analysis of low-molecular-weight peptides and proteins with minimal interference. This technique improves ionization efficiency and sensitivity in electrospray ionization mass spectrometry, facilitating proteomic studies and biomarker discovery.^[40] Acetonitrile is also utilized in the production of dyes and plastics, serving as a solvent and intermediate in the synthesis of various colorants and polymers. Additionally, it finds application in the manufacture of photographic films, where it aids in coating and processing steps; in perfumery as a solvent for extracting and formulating fragrances; in rubber product manufacturing for compounding and processing; and in pesticide production as a reaction medium or intermediate. Furthermore, acetonitrile is employed in the separation of fatty acids from vegetable oils through processes like crystallization or extraction, enhancing the purification of edible oils and oleochemicals.^[3]^[41] In battery applications, acetonitrile acts as a co-solvent in electrolytes for lithium-ion batteries, enhancing ionic conductivity and enabling operation across a wide temperature range from -40°C to 60°C. By blending with carbonate solvents and additives like fluoroethylene carbonate, these formulations promote faster lithium-ion transport and improved cycle life for electric vehicles and portable electronics.^[32]^[42]

Safety and toxicology

Health hazards

Acetonitrile exhibits moderate acute toxicity through oral, dermal, and inhalation routes, primarily due to its biotransformation into hydrogen cyanide (HCN) in the body. The oral LD50 in rats is 2,460 mg/kg, while the inhalation LC50 in rats is 17,100 ppm over 4 hours.^[43]^[44] These values indicate that significant exposure can lead to severe systemic effects, including cyanide poisoning, which arises from the metabolic release of cyanide rather than direct action of the parent compound.^[3] Recent incidents include a 2025 outbreak in Vietnam from acetonitrile-adulterated alcoholic drinks, resulting in 20 hospitalizations and 2 fatalities.^[45] Symptoms of acute acetonitrile poisoning typically manifest with a delayed onset of 2 to 12 hours after exposure, attributed to the time required for metabolic conversion to cyanide. Initial signs include headache, nausea, dizziness, and vomiting, progressing to more severe manifestations such as cyanosis (bluish skin discoloration due to oxygen deprivation), weakness, shortness of breath, confusion, and tachycardia.^[46]^[4] In severe cases, respiratory depression, convulsions, coma, and death may occur if cyanide levels become critically elevated.^[47] The toxicity mechanism involves hepatic metabolism of acetonitrile via cytochrome P450 enzymes, which oxidize it to cyanomethanol (HO-CH₂-CN), followed by further breakdown to cyanide ion (CN⁻) and formaldehyde (HCHO). This process, represented as CH₃CN → HO-CH₂-CN → CN⁻ + HCHO, occurs primarily in the liver and is oxygen- and NADPH-dependent.^[48]^[49] The released cyanide inhibits cytochrome c oxidase in the mitochondrial electron transport chain, disrupting cellular respiration and leading to lactic acidosis and tissue hypoxia.^[3] Once formed, cyanide is detoxified by the enzyme rhodanese, which converts it to thiocyanate using thiosulfate as a sulfur donor; thiocyanate is then excreted primarily in the urine. The biological half-life of unmetabolized acetonitrile in humans is approximately 32 hours, while that of cyanide is about 15 hours, allowing for prolonged exposure to toxic metabolites in cases of significant ingestion or inhalation.^[1]^[50] Chronic exposure to acetonitrile may result in potential damage to the liver and kidneys, as well as central nervous system effects such as numbness and tremors, based on animal studies and limited human data indicating accumulation in these organs.^[4]^[51] The International Agency for Research on Cancer (IARC) has not classified acetonitrile as to its carcinogenicity to humans due to insufficient data.^[52]

Environmental and handling considerations

Acetonitrile is biodegradable under aerobic conditions in water and soil, serving as the primary degradation pathway in these media. In groundwater, the estimated aerobic biodegradation half-life is 2-8 weeks. It demonstrates ready biodegradability, achieving over 60% degradation within 10 days and 70% after 21 days in standard tests using non-adapted activated sludge.^[53] Due to its log Kow value of -0.34, acetonitrile exhibits low bioaccumulation potential and is not expected to concentrate in organisms.^[1] Acetonitrile is regulated as a hazardous air pollutant under the U.S. Clean Air Act by the Environmental Protection Agency.^[54] In the European Union, it is registered under the REACH regulation, with detailed dossiers on its environmental and safety profiles. The Occupational Safety and Health Administration sets a permissible exposure limit of 40 ppm as an 8-hour time-weighted average for workplace air.^[2] As a flammable liquid, acetonitrile has a flash point of 2 °C (closed cup) and an autoignition temperature of 524 °C, necessitating careful handling to avoid ignition sources.^[55] It should be used exclusively in well-ventilated areas such as chemical fume hoods to minimize inhalation exposure.^[56] Storage requires tightly sealed containers in a cool, dry place away from light, heat, and incompatible materials. For spill response, absorb the liquid with inert materials like vermiculite or dry sand, ensure adequate ventilation, and avoid confined spaces.^[4] Acetonitrile is incompatible with strong oxidizers and acids, which can lead to hazardous reactions. Disposal involves incineration at approved facilities or treatment as hazardous waste in accordance with local environmental regulations.^[57]

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