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Butanone

Butanone, also known as 2-butanone or methyl ethyl ketone (MEK), is a simple aliphatic and an important industrial with the molecular formula C₄H₈O. It features a four-carbon chain where the (C=O) is attached to the second carbon atom, giving it the systematic name butan-2-one, and it appears as a colorless, volatile with a characteristic sharp, sweet . This compound is highly flammable and soluble in (to about 27.5 g/100 mL at 20 °C) and miscible with most organic solvents, making it versatile for chemical processes. Key physical properties of butanone include a boiling point of 79.6 °C, a melting point of -86.3 °C, and a density of 0.805 g/cm³ at 20 °C, which contribute to its widespread utility as a low-boiling solvent (see § Properties). Commercially, butanone is produced primarily through the catalytic dehydrogenation of 2-butanol in the gas phase, accounting for about 86% of U.S. production (based on 1991 data), with the remainder derived from the oxidation of n-butane; global production was approximately 1.1 million metric tons in 2022 (see § Production). In industry, butanone serves mainly as a solvent in manufacturing paints, coatings, adhesives, printing inks, and other products, with additional applications in , pharmaceuticals, and purification processes (see § Uses). Regarding , butanone is classified as a hazardous substance due to its flammability ( of -9 °C) and potential effects; acute can cause to the eyes, , and , while higher concentrations may lead to , , , and (see § Safety and ). It is harmful if swallowed or absorbed through the skin, potentially causing or liver and kidney effects upon prolonged , though it is not considered carcinogenic. Occupational limits are set at 200 ppm (time-weighted average) by agencies like OSHA to mitigate risks.

Properties

Physical properties

Butanone, also known as methyl ethyl ketone (MEK), is a with a sweet, acetone-like odor. Its molecular formula is C₄H₈O, and it has a molecular weight of 72.11 g/mol. The compound exhibits a of 79.6 °C and a of −86.3 °C. At 20 °C, its is 78 mmHg. Key physical properties of butanone are summarized in the following table:
PropertyValueConditionsSource
0.8049 g/cm³20 °Chttps://www.sigmaaldrich.com/US/en/product/sigald/360473
1.378820 °C (n_D)https://webbook.nist.gov/chemistry/silmarils-liquids-n-k/docs/META.MIR.PUR.2-Butanone.LIQ.SIGMA-ALDRICH.PNNL515381.pdf
0.41 cP20 °Chttps://trc.nist.gov/ThermoML/10.1021/je050110r.html
−9 °CClosed cuphttps://www.sigmaaldrich.com/US/en/sds/Aldrich/W217018
in 27.5 g/100 mL20 °Chttps://pubchem.ncbi.nlm.nih.gov/compound/Methyl-Ethyl-Ketone
Miscible with , N/Ahttps://pubchem.ncbi.nlm.nih.gov/compound/Methyl-Ethyl-Ketone
2.20 J/g·K25 °Chttps://webbook.nist.gov/cgi/cbook.cgi?ID=C78933&Mask=7
Heat of vaporization31.3 kJ/molhttps://webbook.nist.gov/cgi/cbook.cgi?ID=C78933&Mask=4
These properties indicate butanone's utility as a volatile, low-viscosity that is moderately soluble in but fully compatible with many solvents.

Chemical properties

Butanone, also known as methyl ethyl ketone, has the molecular formula C₄H₈O and the CH₃C(O)CH₂CH₃, featuring a (C=O) at the 2-position of a four-carbon chain, classifying it as a simple aliphatic . The carbonyl carbon in butanone is sp² hybridized, resulting in bond angles approximately 120° around this atom due to the trigonal planar geometry of the C=O unit. The alpha hydrogens in butanone exhibit moderate acidity, with a value of approximately 20, enabling to form ions under basic conditions. The carbonyl oxygen acts as a , with the of its protonated form around -7, allowing coordination with acids in catalytic processes. Butanone undergoes several characteristic reactions typical of ketones. Under extremely vigorous conditions, such as prolonged heating with hot concentrated alkaline KMnO₄, butanone can be oxidized with of the C-C bond adjacent to the carbonyl, yielding acetic acid and propanoic acid. Reduction with (NaBH₄) or catalytic selectively converts the carbonyl to a secondary , producing . In acid-catalyzed , butanone reacts with (Br₂) at the alpha position to form 3-bromobutanone, with the reaction proceeding via the and potentially leading to polyhalogenation if uncontrolled. Butanone also participates in aldol condensation reactions, where it acts as a (via its ) toward aldehydes, forming β-hydroxy ketones or α,β-unsaturated ketones upon , as exemplified in crossed aldol reactions with non-enolizable carbonyls like . Butanone demonstrates good stability under both acidic and basic conditions at moderate temperatures, resisting or , though prolonged exposure to strong bases can promote side reactions via formation. It exhibits a tendency for enolization, equilibrating with its form (but-1-en-2-ol) in trace amounts under acidic or basic , driven by the acidity of its alpha hydrogens and stabilized by in the enol . Spectroscopic characterization of butanone includes a characteristic infrared (IR) absorption for the carbonyl stretch at 1715 cm⁻¹, indicative of an unconjugated aliphatic ketone. In ¹H NMR spectroscopy, the methyl group attached to the carbonyl (CH₃C=O) appears as a singlet at δ 2.1 ppm, the methylene group (CH₂) as a quartet at δ 2.4 ppm, and the terminal methyl (CH₃) as a triplet at δ 1.0 ppm, reflecting the deshielding effect of the carbonyl on adjacent protons.

Production

Industrial production

Butanone, also known as methyl ethyl ketone (MEK), is primarily produced industrially through the catalytic dehydrogenation of 2-butanol. This gas-phase employs catalysts such as , zinc-copper alloys, or oxide at temperatures ranging from 400 to 500 °C and , yielding butanone alongside gas. The reaction proceeds as 2-butanol is vaporized and passed over the catalyst bed, with subsequent cooling and separation of the product stream. This method accounts for the majority of global production due to its efficiency and reliance on readily available feedstocks from refinery streams. A secondary route produces butanone as a from the liquid-phase oxidation of n-butane to acetic acid. This process uses catalysts such as or acetates at 150–225 °C and pressures around 5.5 MPa, yielding butanone alongside other products like , , and . While less dominant than dehydrogenation, it utilizes streams from processing and accounts for approximately 14% of in regions like the U.S. Historically, butanone was largely obtained as a from the modified for phenol and acetone production, involving the oxidation of (isopropylbenzene) derived from and . However, since the 1960s, there has been a shift toward dedicated direct synthesis methods like those described above, driven by increasing demand and process optimizations that improved yields and reduced dependency on phenol coproduction. In modern facilities, the crude product from either route undergoes purification via multistage to achieve greater than 99% purity, removing , unreacted alcohols or alkenes, and light impurities such as acetone. Global production of butanone was approximately 1.1 million metric tons annually as of 2022 and reached about 1.17 million tons in 2024, with projections indicating steady growth to around 1.45 million tons by 2030, primarily fueled by demand in coatings and adhesives. As of 2024, accounts for over 45% of global , with ongoing investments in energy-efficient processes to reduce the ~11.6 /ton energy intensity. China leads as the largest producer, contributing approximately 35% of worldwide output, supported by its expansive . The process is energy-intensive, requiring about 11.6 per ton in optimized setups, encompassing reaction, , and utilities. Economic factors, including feedstock costs from and , influence pricing, which averaged around $1,200 per metric ton in 2024 amid fluctuations in oil prices and regional supply dynamics.

Laboratory synthesis

One common laboratory method for synthesizing butanone involves the oxidation of 2-butanol, a secondary , using Jones reagent, which consists of in aqueous . The reaction proceeds at or slightly above, typically requiring 30 minutes to 1 hour, and yields butanone in 70–95% depending on reaction scale and workup conditions. This method selectively converts the secondary to the corresponding without over-oxidation. A milder alternative is the use of (PCC) in as the solvent. The oxidation of 2-butanol with PCC occurs at over 1–2 hours, providing butanone in 80–90% yield while minimizing side products. To optimize yield, the reaction mixture is stirred under conditions, and excess PCC (1.5 equivalents) is employed to ensure complete conversion. Butanone can also be prepared via the of gem-dichlorides, such as 2,2-dichlorobutane, using aqueous (e.g., KOH or NaOH) under . The gem-dichloride undergoes to form a gem-diol intermediate, which spontaneously dehydrates to the , typically affording 70–85% yield after 2–4 hours of heating. This route is useful when starting from readily available alkyl halides but requires careful control to avoid elimination side reactions. A historical laboratory approach involves the dry distillation of a mixture of calcium acetate and calcium propionate in a 1:1 molar ratio at 400–500°C. This ketonization reaction decarboxylates the salts to produce butanone along with calcium carbonate, with yields around 60–80% based on the propionate content. The distillate is collected and separated from byproducts like acetone formed from excess acetate. Following synthesis, butanone is purified by solvent extraction with diethyl ether to remove aqueous impurities, followed by fractional distillation at atmospheric pressure (boiling point 79.6°C). This process achieves >95% purity for analytical use, with extraction efficiencies improved by multiple washes and drying over anhydrous sodium sulfate. In laboratory settings, safety precautions are essential when handling oxidants; for instance, chromic acid and PCC generate toxic chromium(VI) waste, requiring fume hood operation and proper disposal, while potassium permanganate (an alternative oxidant for 2-butanol) poses risks as a strong oxidizer and must be used in cooled conditions to prevent runaway reactions.

Uses

Solvent applications

Butanone, also known as methyl ethyl ketone (MEK), serves as an effective in numerous applications due to its moderate , characterized by a dielectric constant of 18.5 at 20°C. This property enables it to dissolve a range of polar and semi-polar substances, including resins, adhesives, and components in paints, facilitating their formulation and application. In the coatings industry, butanone is widely employed in nitrocellulose lacquers for and automotive paints, where it provides rapid drying and good solvency for polymers. It is also used in the production of films for and , as well as in magnetic tapes, where it aids in dispersing magnetic particles and binding them to the . Additionally, butanone functions as an in the for isolating active compounds and in oil refining processes for dewaxing lubricating oils by selectively dissolving waxes. As a in polymer processing, it dissolves at concentrations typically ranging from 10% to 20% by weight, enabling casting and molding operations. One key advantage of butanone over more hazardous alternatives like is its lower toxicity profile; is classified as a Class 1 residual solvent due to its carcinogenic potential, whereas butanone falls into Class 3, indicating minimal toxicological concern at typical exposure levels. Its evaporation rate, approximately 3.8 relative to n-butyl acetate, contributes to efficient drying in solvent-based systems without excessive residue. In 2023, solvent applications accounted for approximately 50% of global butanone consumption, underscoring its dominant role in industrial formulations.

Other industrial uses

Butanone, commonly known as methyl ethyl ketone (MEK), plays a vital role in by cleaning and softening the surfaces of thermoplastics such as (PVC) and acrylics, enabling effective bonding without heat. This process is widely applied in the automotive sector for repairing dashboards, bumpers, and interior components, as well as in the signage industry for assembling durable acrylic displays and letters. As a chemical intermediate, MEK is essential for producing (MEKP), a catalyst that initiates the polymerization of unsaturated polyester used in fiberglass-reinforced plastics for boat hulls, automotive parts, and construction materials. MEKP is synthesized by oxidizing MEK with under controlled conditions to ensure stability and efficacy in resin curing. MEK is incorporated into flexographic inks as a solvent to dissolve resins and control , supporting high-speed printing on flexible packaging, labels, and corrugated materials. In anti-corrosion coatings, it facilitates uniform film formation on metal substrates, enhancing and barrier properties to prevent in and environments. In household products, MEK appears in glues and sealants for bonding plastics and metals, as well as in removers to dissolve cured coatings, often at concentrations of 5–40% to balance and in commercial formulations. Niche applications include lube oil dewaxing, where MEK acts as a selective to extract crystals from lubricating oils, improving and cold-flow performance in refining. It is also used in synthetic rubber processing to dissolve and blend polymers, aiding the of tires, hoses, and . As of , chemical intermediates account for approximately 15% of global MEK use, while adhesives and related applications represent around 20%, reflecting steady demand in sectors.

Safety and regulation

Flammability hazards

Butanone, also known as methyl ethyl ketone (MEK), is as a Class IB flammable liquid according to the (NFPA), characterized by a below 22.8 °C (73 °F) and a above 37.8 °C (100 °F). This underscores its high and potential for ignition under ambient conditions, with an NFPA flammability rating of 3, indicating that it can be ignited under almost all ambient temperatures and produces hazardous atmospheres when vapors are present in air. The autoignition temperature of butanone is 515 °C (959 °F), meaning it can spontaneously ignite in air without an external spark or flame at this threshold. Additionally, its limits in air range from 1.4% to 11.4% by volume, allowing vapor-air mixtures within this concentration to form atmospheres if ignited. The vapor density of butanone is 2.5 (relative to air at 1), which causes its vapors to be heavier than air and prone to accumulation in low-lying areas, basements, or confined spaces, thereby increasing the risk of flash-back ignition from distant sources. This behavior heightens explosion risks in poorly ventilated environments where vapors can travel along the ground to ignition sources such as open flames, sparks, or hot surfaces. In terms of firefighting, suitable extinguishing agents include alcohol-resistant foam, carbon dioxide, or dry chemical extinguishers, as these suppress vapors effectively without exacerbating the fire; however, direct water streams should be avoided, as they can spread the flammable liquid and vapors rather than contain the blaze. Safe storage practices for butanone mandate the use of grounded metal containers to prevent buildup, maintained at temperatures below 27 °C (80 °F) in well-ventilated areas distant from ignition sources, heat, or incompatible materials like strong oxidizers. A notable incident illustrating these s occurred on October 2, 2007, at the Cabin Creek hydroelectric plant near , where MEK vapors accumulated in a during equipment cleaning, ignited, and caused a that resulted in five fatalities due to inadequate preparation and . Such events highlight the critical need for rigorous controls to mitigate butanone's flammability risks in industrial settings.

Health and toxicity effects

Butanone can cause acute irritation to the eyes and , with mild eye discomfort and slight nose and throat irritation reported in humans at concentrations of 100 for 6 hours. At 200 , some individuals experience mild eye irritation and symptoms of (CNS) depression, such as headache, , and a feeling of after 4 hours of . Higher concentrations, above 10,000 , lead to severe respiratory and ocular irritation in animals, including lacrimation and . Chronic exposure to butanone has been associated with potential liver and damage in , with increased liver weights observed in female rats exposed to 3,000 for 15 days, though no histopathological lesions were noted. In rats, oral doses around 1,080 mg/kg caused mild renal tubule , indicating effects at elevated levels, while the OSHA (PEL) is set at 200 to prevent such risks. Potential , including and , has been observed in animals at chronic high doses, though suggest minimal long-term neurological impacts below occupational limits. The (LD50) for butanone in rats is approximately 2,737 mg/kg orally and 11,700 via inhalation for 4 hours. Butanone is rapidly metabolized in the liver primarily via 2E1 () to 3-hydroxy-2-butanone, which is further reduced to 2,3-butanediol; these metabolites are excreted in urine, with rapid elimination preventing significant accumulation. Studies on reproductive and developmental effects show no teratogenicity in rats and mice exposed to up to 3,000 during , though slight fetotoxicity, such as reduced fetal body weight, occurred at this level without embryotoxic or teratogenic outcomes. Regarding carcinogenicity, butanone is not classifiable as to its carcinogenicity to humans by the International Agency for Research on Cancer (IARC Group 3), due to inadequate evidence in humans and animals.

Environmental and regulatory aspects

Butanone exhibits favorable environmental fate characteristics, being readily biodegradable in aerobic conditions. According to OECD Test Guideline 301D, it achieves 98% biodegradation within 28 days, meeting the criteria for ready biodegradability. Its low octanol-water partition coefficient (log Kow of 0.29) indicates minimal potential for bioaccumulation in aquatic organisms. In the atmosphere, butanone primarily undergoes via reaction with hydroxyl (OH) radicals, with an estimated of about 1 day (approximately 21 hours) under typical conditions. As a (VOC), it contributes to the formation of photochemical by participating in reactions that generate and other secondary pollutants. Butanone demonstrates low to aquatic life. The 96-hour LC50 for (e.g., bluegill sunfish) is 2480 mg/L, indicating moderate tolerance, while concentrations below 100 mg/L show no significant adverse effects on growth. These toxicity thresholds inform regulatory limits on environmental releases to protect ecosystems. Regulatory frameworks address butanone's environmental releases due to its VOC status and potential ecological impacts. Under the U.S. Clean Air Act, the Environmental Protection Agency (EPA) classifies butanone as a subject to emission controls, though it receives exemptions or reduced reactivity weighting in certain architectural coatings to limit formation. In the , butanone is registered under REACH with no specific Annex XVII restrictions, but its use in mixtures is monitored for environmental hazards, including aquatic chronic toxicity classifications. The (OSHA) sets a of 200 ppm as an 8-hour time-weighted average for workplace air to mitigate risks during handling. For spill response, butanone releases should be contained using absorbent materials such as or , followed by proper disposal as ; entry into waterways must be prevented to avoid diluting aquatic habitats. Global regulatory trends emphasize reducing butanone emissions to curb . In , post-2020 amendments to the Aerosol Coatings Regulation under the Air Resources Board limit VOC content and reactivity in consumer aerosol products, effectively phasing out high-butanone formulations to combat , with methyl ethyl ketone assigned a maximum incremental reactivity of 1.48. Production facilities worldwide are increasingly required to monitor and report emissions under frameworks like the EPA's Toxics Release Inventory.

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