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2-Butanol

2-Butanol, also known as butan-2-ol or sec-butyl alcohol, is a secondary alcohol with the chemical formula C₄H₁₀O and structural formula CH₃CH(OH)CH₂CH₃.^[1]^[2] It is a chiral molecule existing as two enantiomers, and the racemic mixture is a colorless liquid with a characteristic sweet odor at room temperature.^[1] This compound serves primarily as an industrial solvent and chemical intermediate, with applications in extraction processes, flavoring, and synthesis of other chemicals.^[3]^[1] Physically, 2-butanol has a boiling point of 99–100 °C, a melting point of approximately -115 °C, a density of 0.81 g/cm³, and is soluble in water (125–181 g/L at 20–25 °C).^[1]^[2]^[3] Chemically, it is flammable with a flash point of 24 °C and can form explosive peroxides upon exposure to air; it reacts with strong oxidants and certain metals like aluminum.^[2]^[1] The compound is produced industrially through hydration of butene or reduction of butanone, and it exhibits moderate biodegradability in environmental settings.^[1] Key uses of 2-butanol include its role as a solvent for resins, paints, and industrial cleaners, as well as an extraction agent for processes like fish protein concentrate production and an intermediate in methyl ethyl ketone manufacturing.^[1]^[3] It is also employed as a flavoring agent in food and beverages due to its mild taste.^[3] From a safety perspective, 2-butanol is classified as a flammable liquid that poses risks of eye, skin, and respiratory irritation, along with central nervous system effects such as drowsiness and dizziness at high exposures.^[2]^[1] Toxicological data indicate an acute oral LD₅₀ in rats of about 6.5 g/kg, suggesting low acute toxicity, though inhalation can lead to narcosis and it may cause aspiration hazards if swallowed.^[3]^[1] Occupational exposure limits are set at 100 ppm as a time-weighted average.^[2]

Chemical identity and nomenclature

Structural formula and molecular properties

2-Butanol, also known as butan-2-ol, is an organic compound with the molecular formula C₄H₁₀O.^[1] Its structural formula is CH₃CH(OH)CH₂CH₃, featuring a linear four-carbon chain where a hydroxyl group (-OH) is attached to the second carbon atom.^[1] This configuration classifies 2-butanol as a secondary alcohol, in which the hydroxyl group is bonded to a carbon atom that is itself connected to two alkyl groups (a methyl and an ethyl group).^[1] The molecule has a molar mass of 74.12 g/mol.^[4] In terms of molecular geometry, the carbon atoms in the chain adopt tetrahedral arrangements with typical C-C bond lengths of approximately 1.54 Å and C-O bond lengths of about 1.43 Å, consistent with sp³ hybridization in aliphatic alcohols.^[5] The O-H bond length is around 0.96 Å, and bond angles at the hydroxyl-bearing carbon and oxygen are near 109.5°.^[5] Key identifiers for 2-butanol are summarized below:

Identifier	Value
CAS Number	78-92-2
SMILES	CCC(C)O
InChI	InChI=1S/C4H10O/c1-3-4(2)5/h4-5H,3H2,1-2H3

Naming and stereochemistry

The IUPAC name for 2-butanol is butan-2-ol.^[1] It is also known by common names such as sec-butanol, sec-butyl alcohol, and ethyl methyl carbinol.^[6] 2-Butanol is one of four structural isomers of butanol (C₄H₁₀O), the others being 1-butanol (butan-1-ol), 2-methyl-1-propanol (isobutanol), and 2-methyl-2-propanol (tert-butanol).^[1] 2-Butanol possesses a chiral center at the carbon atom in position 2, which bears four different substituents: a hydroxyl group, a methyl group, an ethyl group, and a hydrogen atom. This chirality results in two enantiomers: (2R)-butan-2-ol, also denoted as (R)-(-)-2-butanol, and (2S)-butan-2-ol, or (S)-(+)-2-butanol. These enantiomers are non-superimposable mirror images of each other and exhibit identical physical properties except for their optical rotation. In most industrial and laboratory contexts, 2-butanol is produced and utilized as a racemic mixture, containing equal proportions of the (R) and (S) enantiomers.^[7] The specific rotation [\alpha]_D^{25} for pure (S)-(+)-2-butanol is +13.52°, while for (R)-(-)-2-butanol it is -13.52°. These values indicate that the (S) enantiomer rotates plane-polarized light to the right (dextrorotatory), and the (R) enantiomer rotates it to the left (levorotatory).^[8] Enantiomerically pure forms of 2-butanol can be obtained through classical resolution methods, which involve forming diastereomeric salts with a chiral resolving agent, such as a chiral acid or base, followed by separation based on differing solubilities; subsequent liberation of the alcohol yields the individual enantiomers.^[9]

Physical properties

Appearance and basic physical data

2-Butanol appears as a clear, colorless liquid at standard conditions, exhibiting a strong, fruity odor often described as pleasant and alcoholic. The odor threshold is approximately 3.2 ppm.^[1]^[10] Key physical measurements include the following:

Property	Value	Conditions	Source
Density	0.808 g/cm³	20°C	https://www.chemeo.com/cid/46-479-0/2-Butanol.pdf
Refractive index	1.3978	20°C	https://pubchem.ncbi.nlm.nih.gov/compound/2-Butanol
Viscosity	~3.5 mPa·s	20°C	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0751661.htm
Flash point	22–27°C (closed cup)	-	https://pubchem.ncbi.nlm.nih.gov/compound/6568
Autoignition temperature	405°C	-	https://www.chemeo.com/cid/46-479-0/2-Butanol.pdf

Thermodynamic properties

2-Butanol exhibits typical thermodynamic behaviors of a secondary alcohol, remaining in the liquid phase at room temperature and atmospheric pressure due to its melting point of -114.7 °C and boiling point of 99.5 °C. These phase transition temperatures indicate that the compound freezes at moderately low temperatures and vaporizes near 100 °C under standard conditions, consistent with its role in various industrial processes involving heating or cooling.^[11] The vapor pressure of 2-butanol is 1.67 kPa at 20 °C, reflecting its moderate volatility and potential for forming flammable vapors in air.^[12] The heat of vaporization is approximately 40.8 kJ/mol at the boiling point, corresponding to 583 kJ/kg, which quantifies the energy required for phase change from liquid to gas and influences distillation efficiency.^[11] The liquid heat capacity is 197.1 J/mol·K at 298.15 K, providing a measure of the energy needed to raise its temperature in liquid form.^[13] At higher pressures and temperatures, 2-butanol reaches its critical temperature of 536 K (263 °C), beyond which it cannot be liquefied regardless of pressure, marking the end of distinct liquid and vapor phases.^[14] The phase diagram of 2-butanol shows a stable liquid region between its melting and boiling points at 1 atm, with vapor pressure curves describing the equilibrium between liquid and gas phases up to the critical point.^[11]

Property	Value	Conditions	Source
Melting point	-114.7 °C	1 atm	PubChem
Boiling point	99.5 °C	1 atm	PubChem
Vapor pressure	1.67 kPa	20 °C	Sigma-Aldrich
Heat of vaporization	40.8 kJ/mol (583 kJ/kg)	Boiling point	NIST WebBook
Heat capacity (liquid)	197.1 J/mol·K	298.15 K	NIST WebBook
Critical temperature	536 K (263 °C)	Critical point	NIST WebBook

Solubility

2-Butanol has a solubility in water of 35.0 g per 100 g of water at 20°C, decreasing with increasing temperature to 29 g per 100 g at 25°C and 22 g per 100 g at 30°C.^[15] These values reflect the compound's ability to form hydrogen bonds with water molecules, though solubility diminishes as thermal energy disrupts these interactions.^[15] Earlier reports citing a solubility of 12.5 g/100 g at 20°C, found in many textbooks and databases, stem from a historical miscalculation based on volume measurements rather than mass, as clarified in experimental re-evaluations.^[15] The compound is completely miscible with ethanol, diethyl ether, chloroform, and most organic solvents, owing to compatible intermolecular forces such as hydrogen bonding and van der Waals interactions. The octanol-water partition coefficient (log P) for 2-butanol is 0.61, signifying moderate hydrophilicity where the polar -OH group promotes aqueous affinity while the butyl chain confers some lipophilicity.^[16] 2-Butanol is miscible with non-polar hydrocarbons such as hexane.^[17] This behavior arises primarily from hydrogen bonding enabled by the -OH group, which favors polar environments over purely hydrocarbon ones.

Synthesis

Industrial production

The primary industrial production of 2-butanol involves the acid-catalyzed hydration of butene isomers, particularly 1-butene and 2-butene, sourced from petroleum refining streams such as raffinate-2.^[18]^[19] This process has become the dominant method since the mid-20th century, replacing earlier, less efficient routes as petrochemical feedstocks became abundant and cost-effective.^[19] The conventional approach is an indirect hydration using concentrated sulfuric acid as the catalyst. In the first step, butene reacts with sulfuric acid to form sec-butyl hydrogen sulfate (and some di-sec-butyl sulfate as a byproduct):

\text{CH}_3\text{CH=CHCH}_3 + \text{H}_2\text{SO}_4 \rightarrow \text{CH}_3\text{CH(OSO}_3\text{H})\text{CH}_2\text{CH}_3

This intermediate is then hydrolyzed with water under controlled conditions (typically at 70–90°C and atmospheric pressure) to produce 2-butanol while regenerating the sulfuric acid for recycling:

\text{CH}_3\text{CH(OSO}_3\text{H})\text{CH}_2\text{CH}_3 + \text{H}_2\text{O} \rightarrow \text{CH}_3\text{CH(OH)CH}_2\text{CH}_3 + \text{H}_2\text{SO}_4

The overall process operates in a continuous or semi-continuous manner, with butene absorption in acid followed by hydrolysis and distillation to separate the product. Yields typically reach 90–95%, depending on butene composition and process optimization, with byproducts like di-sec-butyl sulfate converted during hydrolysis to minimize waste.^[20] Acid corrosion and effluent management are key engineering challenges addressed through material selection and neutralization steps.^[21] Alternative industrial routes include direct hydration using solid acid catalysts such as zeolites (e.g., H-ZSM-5 or beta zeolites) in fixed-bed reactors, which avoid liquid acid handling but are less widespread due to ongoing deactivation issues from water and coke formation. Direct hydration processes have been commercialized, for example, using phosphoric acid catalysts or supported ion-exchange resins.^[21] Another option is the catalytic hydrogenolysis of butanone (methyl ethyl ketone), often over supported copper or nickel catalysts under mild hydrogen pressure (1–10 bar, 100–200°C), though this is typically integrated into solvent production chains rather than standalone for 2-butanol.^[22] Global production of 2-butanol occurs on the scale of thousands of metric tons annually, largely as a co-product in multi-output butene hydration processes that also yield butanes, with major capacity in Asia and North America.^[23]^[20]

Laboratory methods

One common laboratory method for synthesizing 2-butanol involves the Grignard reaction, where ethylmagnesium bromide reacts with acetaldehyde to form the magnesium alkoxide intermediate, followed by acidic hydrolysis to yield the alcohol.^[24] The reaction proceeds as follows:

\ce{CH3CHO + CH3CH2MgBr -> CH3CH(OMgBr)CH2CH3 ->[H2O/H+] CH3CH(OH)CH2CH3}

This approach is suitable for small-scale preparations due to the availability of reagents and straightforward workup under anhydrous conditions.^[24] Another widely used laboratory route is the reduction of butanone (methyl ethyl ketone) to 2-butanol. Sodium borohydride (NaBH₄) serves as a mild, selective reducing agent for this transformation, typically performed in protic solvents like methanol or ethanol at room temperature.^[25] The reduction equation is:

\ce{CH3C(O)CH2CH3 + NaBH4 -> CH3CH(OH)CH2CH3}

Catalytic hydrogenation using nickel or palladium catalysts under hydrogen gas pressure offers an alternative, often achieving high yields in laboratory settings with controlled stereochemistry potential.^[25] For the preparation of enantiomerically enriched 2-butanol, asymmetric synthesis via catalytic hydrogenation of butanone employs chiral ruthenium-BINAP complexes, pioneered by Noyori, enabling high enantioselectivity (up to 100% ee) for simple aliphatic ketones lacking directing groups.^[26] These reactions utilize Ru(II) catalysts with diphosphine ligands like BINAP and diamine co-ligands, proceeding under mild hydrogen pressure (4–100 atm) in alcoholic solvents, with substrate-to-catalyst ratios up to 10,000.^[26] Purification of laboratory-synthesized 2-butanol typically involves fractional distillation to remove impurities and unreacted materials. Due to its formation of a minimum-boiling azeotrope with water (boiling at approximately 90°C), anhydrous conditions or additional drying agents like molecular sieves are often required post-distillation to obtain pure product.^[27]

Chemical properties and reactions

General reactivity

2-Butanol is a secondary alcohol, characterized by a hydroxyl group attached to a carbon bearing two alkyl substituents, which imparts specific reactivity patterns dominated by the functional group. This structural feature makes it susceptible to oxidation under mild conditions, typically yielding ketones such as butan-2-one, and to dehydration, which eliminates water to form alkenes like but-1-ene, (E)-but-2-ene, and (Z)-but-2-ene. The acidity of 2-butanol arises from the -OH proton, with a pKa value of approximately 17.7, rendering it a weaker acid than water (pKa 15.7); this reduced acidity stems from the electron-donating effects of the adjacent alkyl groups, which stabilize the neutral alcohol relative to the alkoxide ion.^[16] In terms of basicity, the lone pairs on the oxygen atom allow 2-butanol to act as a weak base by accepting a proton, though it is only marginally basic, as indicated by the pKa of its protonated conjugate acid (2-butanolium ion) at about -1.6.^[16] Under neutral conditions at ambient temperatures, 2-butanol exhibits good chemical stability, showing no significant decomposition. However, upon strong heating, it undergoes thermal decomposition, primarily through dehydration pathways to produce butene and water, along with potential formation of other byproducts.^[28] Additionally, like certain other alcohols, 2-butanol has the potential to form unstable peroxides when exposed to air over extended periods, particularly if concentrated by distillation or evaporation; these peroxides can be explosive and require careful handling to mitigate risks.^[29] Spectroscopic methods provide reliable identification of 2-butanol's functional group and structure. In infrared (IR) spectroscopy, the characteristic O-H stretching vibration manifests as a broad absorption band centered around 3300 cm⁻¹, indicative of hydrogen bonding in the alcohol.^[30] Proton nuclear magnetic resonance (¹H NMR) spectroscopy reveals key signals, including a doublet for the three protons of the methyl group attached to the carbinol carbon (C1 in CH₃-CHOH-), typically around 1.1 ppm, and a multiplet for the single methine proton at the carbinol carbon (C2), appearing near 3.8 ppm due to coupling with adjacent protons and the hydroxyl group.

Specific reactions

One key transformation of 2-butanol involves its oxidation to butan-2-one (methyl ethyl ketone, MEK), a secondary alcohol to ketone conversion. This reaction proceeds using pyridinium chlorochromate (PCC) in dichloromethane, which selectively oxidizes the secondary alcohol without over-oxidation, yielding the ketone and chromium byproducts.^[31] Alternatively, chromic acid (Jones reagent, CrO₃ in aqueous sulfuric acid) achieves the same oxidation, forming a chromate ester intermediate that eliminates to the ketone.^[32] The general equation is:

\mathrm{CH_3CH(OH)CH_2CH_3 + [O] \rightarrow CH_3COCH_2CH_3 + H_2O}

where [O] represents the oxidant.^[31] Dehydration of 2-butanol eliminates water to form butene isomers, typically using concentrated sulfuric acid at 140°C, following an E1 mechanism via a secondary carbocation intermediate.^[33] Zaitsev's rule dictates the major product as the more substituted alkene, 2-butene (cis and trans isomers), with 1-butene as the minor product.^[33] Esterification of 2-butanol with carboxylic acids, such as acetic acid, occurs via the Fischer method under acidic catalysis (e.g., H₂SO₄ reflux), forming sec-butyl esters through protonation of the carbonyl, nucleophilic attack by the alcohol, and elimination of water.^[34] For acetic acid, the product is sec-butyl acetate.^[35] The equation is:

\mathrm{CH_3CH(OH)CH_2CH_3 + CH_3COOH \rightleftharpoons CH_3CH(OCOCH_3)CH_2CH_3 + [H_2O](/page/Water)}

This equilibrium reaction favors the ester with excess alcohol or removal of water.^[34] Halogenation converts 2-butanol to 2-bromobutane using phosphorus tribromide (PBr₃), where the alcohol oxygen coordinates to phosphorus, forming a phosphite ester that undergoes bromide attack.^[36] This SN2 pathway results in inversion of configuration at the chiral carbon for enantiopure 2-butanol.^[36] Due to its chirality, 2-butanol exhibits stereospecific behavior in reactions; acidic conditions, such as dilute sulfuric acid, lead to racemization via protonation of the hydroxyl group, carbocation formation, and nucleophilic attack from either side.^[37] In contrast, enzymatic oxidations, such as by yeast alcohol dehydrogenase (ADH1), preserve stereochemistry, preferentially oxidizing (S)-2-butanol over the (R)-enantiomer with high enantioselectivity.^[38]

Applications

Industrial applications

2-Butanol serves primarily as a precursor for the industrial production of methyl ethyl ketone (MEK), an important solvent in paints, adhesives, and coatings.^[39] The dehydrogenation process involves the catalytic conversion of 2-butanol to MEK and hydrogen gas, typically using copper-zinc oxide (Cu/ZnO) catalysts at temperatures of 400-550°C, achieving yields of 85-90%.^[40] In the United States, approximately 86% of MEK production derives from this route, with global MEK output exceeding 1.1 million metric tons annually as of 2022, a significant portion of which originates from 2-butanol.^[39]^[41] The compound is also employed as a solvent in the manufacture of coatings and printing inks, owing to its moderate polarity and controlled evaporation rate, which facilitate effective dissolution of resins and polymers while ensuring proper film formation.^[42] Additionally, 2-butanol functions as an extractant in petrochemical processes for separating hydrocarbons, leveraging its selective solvency properties to isolate specific fractions from complex mixtures.^[43] In ester production, 2-butanol reacts with acetic acid to form sec-butyl acetate, a versatile ester utilized in lacquers for surface coatings and as a component in flavor formulations.^[44]^[18]

Other uses

2-Butanol serves as a precursor for the synthesis of sec-butyl acetate, a volatile ester employed in artificial fruit flavorings, particularly those mimicking banana and pear profiles. This ester contributes to the fruity notes in confectionery, beverages, and other food products, leveraging its organoleptic properties for sensory enhancement.^[45] Enantiopure forms of 2-butanol, such as (R)-(-)-2-butanol, act as chiral auxiliaries or intermediates in the biocatalytic synthesis of pharmaceutical compounds, enabling the production of stereospecific drugs through enzymatic reductions or resolutions. These applications capitalize on the molecule's chirality to achieve high enantiomeric purity in active pharmaceutical ingredients, as demonstrated in processes involving oxidoreductases for chiral alcohol intermediates.^[46]^[47] In laboratory settings, 2-butanol functions as a solvent for organic extractions, particularly effective for isolating polar compounds from aqueous phases due to its moderate hydrophilicity and compatibility with non-polar solvents like hexane. Its relatively low acute toxicity, with an oral LD50 of 6.5 g/kg in rats, makes it suitable for such routine procedures where safer alternatives to more hazardous solvents are preferred.^[1] Additionally, 2-butanol is utilized in nuclear magnetic resonance (NMR) spectroscopy, both as an analyte for spectral characterization and occasionally as a co-solvent in studies of alcohol mixtures, benefiting from its well-documented chemical shift data.^[17] As a potential biofuel additive, 2-butanol can be blended into gasoline at low concentrations (typically under 1% by volume in experimental formulations) to enhance octane ratings and improve combustion efficiency, offering a renewable alternative to traditional oxygenates while maintaining compatibility with existing fuel infrastructure. Such blends have been explored in patents for mixed butanol fuels, where sec-butanol contributes to anti-knock properties without significantly altering vehicle performance.^[48] In analytical chemistry, 2-butanol is employed as a calibration standard and internal standard in gas chromatography (GC) methods for quantifying alcohols, including in blood alcohol concentration (BAC) analysis and quality control of oxygenated fuels. Certified standards from suppliers ensure accurate retention time and response factor calibration, supporting precise detection limits in forensic and industrial applications.^[49]^[50]

Safety, handling, and environmental impact

Health and safety hazards

2-Butanol exhibits low acute toxicity via oral exposure, with an LD50 of 2.193 g/kg in rats, indicating it is not highly poisonous but can cause adverse effects at elevated doses.^[51] Inhalation toxicity is also relatively low, with an LCLo of 16,000 ppm for 4 hours in rats, leading to symptoms such as central nervous system depression, ataxia, and prostration at high concentrations.^[51] Like other secondary alcohols, it acts as a mild to moderate irritant to the eyes, skin, and respiratory tract, potentially causing redness, tearing, and discomfort upon direct contact or vapor inhalation at elevated levels.^[52] Chronic exposure to 2-butanol may result in defatting and drying of the skin, leading to dermatitis with prolonged contact, and it can function as a central nervous system depressant similar to other alcohols, potentially causing narcosis or neurological effects over time.^[52] It is not classified as a carcinogen by the International Agency for Research on Cancer (IARC), with no evidence of carcinogenic potential in available data. As a physical hazard, 2-butanol is a highly flammable liquid classified as NFPA Class IB, with a flash point of 24°C and the ability to form explosive vapor-air mixtures in concentrations ranging from 1.7% to 9.8% by volume.^[52] Additionally, it poses a peroxide formation risk, auto-oxidizing in air to produce unstable peroxides that can become explosive, particularly in aged or distilled samples, with reported incidents of detonation upon disturbance.^[52] Occupational exposure limits for 2-butanol include an OSHA Permissible Exposure Limit (PEL) of 150 ppm as an 8-hour time-weighted average (TWA) and a NIOSH Recommended Exposure Limit (REL) of 100 ppm TWA with a short-term exposure limit (STEL) of 150 ppm.^[53]^[54]

Precautions and regulations

2-Butanol should be stored in a cool, dry, well-ventilated area, preferably in a dedicated flammables cabinet, away from heat sources, ignition points, and oxidizing agents to minimize fire risks and chemical incompatibility. Containers must be kept tightly closed to prevent vapor buildup, and non-sparking tools and explosion-proof equipment should be used during handling to avoid static discharge or sparks, given its low flash point of approximately 24°C.^[55]^[56] Safe handling requires the use of personal protective equipment, including nitrile or chloroprene gloves, safety goggles or face shield, and flame-retardant antistatic clothing to protect against skin contact, eye irritation, and fire hazards. Operations should be conducted in a fume hood or well-ventilated space to avoid inhalation of vapors, with grounding of equipment to prevent static ignition; direct contact with skin or eyes must be avoided.^[55]^[56] As a secondary alcohol, 2-butanol may form explosive peroxides upon prolonged storage, particularly if concentrated by evaporation or distillation, necessitating the addition of stabilizers such as butylated hydroxytoluene (BHT) to inhibit autoxidation and routine testing for peroxides prior to such processes. Commercial supplies often include inhibitors, but their efficacy diminishes over time, so fresh material or stabilized grades are recommended.^[56]^[57] In the event of a spill, immediately eliminate all ignition sources and ventilate the area to disperse vapors, then absorb the liquid with an inert material such as sand or vermiculite and transfer to suitable closed containers for disposal, ensuring spills do not enter drains or waterways.^[55]^[56] Under the Globally Harmonized System (GHS), 2-butanol is classified as a flammable liquid (Category 3, H226: Flammable liquid and vapour) and an eye irritant (Category 2A, H319: Causes serious eye irritation), requiring appropriate labeling and safety data sheets for transport and use. In the European Union, it is registered under REACH with number 01-2119475146-36-xxxx, subjecting it to evaluation and potential restrictions. In the United States, it is listed as an active substance on the Toxic Substances Control Act (TSCA) inventory.^[55]^[58]^[59] First aid measures include flushing eyes immediately with plenty of water for at least 15 minutes while holding eyelids open and seeking medical attention; for ingestion, do not induce vomiting and obtain immediate medical help, particularly if more than 50 mL has been swallowed, to prevent aspiration risks.^[55]^[56]

Environmental considerations

2-Butanol is readily biodegradable under aerobic conditions, with studies demonstrating greater than 90% degradation within 5 days according to OECD Guideline 301C.^[60] This low persistence indicates minimal long-term accumulation in environmental compartments such as soil and water.^[60] The compound exhibits low bioaccumulation potential, characterized by an octanol-water partition coefficient (log Kow) of 0.61 and a bioconcentration factor (BCF) estimated at 0.66.^[60] These properties suggest negligible uptake and magnification in aquatic organisms.^[60] Ecotoxicity assessments reveal low acute risk to aquatic life, with a 96-hour LC50 of 3,670 mg/L for fathead minnows (Pimephales promelas).^[60] Corresponding values include a 48-hour EC50 of 3,500 mg/L for Daphnia magna and an EC50 of 8,900 mg/L for algae, confirming limited toxicity at environmentally relevant concentrations.^[60] In the atmosphere, 2-butanol primarily degrades through reaction with hydroxyl (OH) radicals, with an estimated half-life of approximately 34 hours under typical tropospheric conditions.^[61] This rapid degradation pathway reduces its contribution to long-range atmospheric transport or secondary pollutant formation.^[60] Primary release sources of 2-butanol to the environment stem from industrial effluents during manufacturing and use as a solvent or intermediate, while consumer applications contribute minimally due to contained usage.^[3] Regulatory evaluations classify 2-butanol as not meeting persistent, bioaccumulative, and toxic (PBT) criteria under frameworks like REACH Annex XIII, owing to its biodegradability and low bioaccumulation.^[62] In the United States, it is not designated a priority pollutant but may be subject to monitoring under the Clean Water Act for industrial discharges via National Pollutant Discharge Elimination System (NPDES) permits.^[63]

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[23]
The gas phase hydrogenation of 2-butanone over supported nickel ...
The gas phase hydrogenation of 2-butanone to 2-butanol at 343 K promoted using a Y zeolite-supported nickel catalyst (2.2% w/w Ni) prepared by ion exchange ...
[24]
2-butanol production by hydration of butene, UPR, ecoinvent 3.6 ...
The multioutput-process "butene hydration" delivers the co-products 2-butanol and butanes from butenes. The allocation is based on mass balance.
[25]
[PDF] The Final Learning Experience
(b) Suggest a synthesis of 2-butanol by way of a Grignard reaction starting from H3C-CH2-CHO. Draw the Lewis structures of the substrate, specify the ...
[26]
[PDF] NaBH4 Reduction of Ketone to Alcohol 39 NaBH
NaBH4 Reduction of Ketone to Alcohol. 39. NaBH. 4. Reduction of 2-Methylcyclohexanone. Use of H-NMR Integration for Analysis of Isomeric Product Ratios.
[27]
[PDF] Ryoji Noyori - Nobel Lecture
Furthermore, asymmetric hydrogenation was limited to the synthesis of amino acids. A major breakthrough occurred when we devised the BINAP-Ru (II) dicar-.Missing: butanone | Show results with:butanone
[28]
Separation of 2-butanol–water mixtures by pervaporation through ...
Aug 9, 2025 · 2BuOH forms a binary azeotrope with water, which is hard to separate by distillation [10] . Therefore, recovery of this alcohol from aqueous ...
[29]
2-Butanol CAS#: 78-92-2 - ChemicalBook
Boiling point is 99.5 ℃. The flash point is 28 ℃. The refractive index is 1.3955. Specific rotation is-13.51 ° (25 ℃). 2-butanol oxidation can generate methyl ...Missing: viscosity | Show results with:viscosity
[30]
https://webbook.nist.gov/cgi/cbook.cgi?ID=C78922&Type=IR-SPEC&Index=1
[31]
2-Butanol - the NIST WebBook
This IR spectrum is from the Coblentz Society's evaluated infrared reference spectra collection. References. Go To: Top, Infrared Spectrum, Notes. Data ...
[32]
Oxidation by PCC (pyridinium chlorochromate) - Chemistry LibreTexts
Jan 22, 2023 · PCC oxidizes alcohols one rung up the oxidation ladder, from primary alcohols to aldehydes and from secondary alcohols to ketones.
[33]
17.7: Oxidation of Alcohols - Chemistry LibreTexts
Mar 17, 2024 · PCC oxidizes 1o alcohols one rung up the oxidation ladder, turning primary alcohols into aldehydes and secondary alcohols into ketones.
[34]
10.4: Elimination Reactions of Alcohols- Dehydration
Aug 9, 2014 · Application of this reaction sequence is shown here for 2-butanol. The Zaitsev rule favors the formation of 2-butene (cis + trans) over 1-butene ...
[35]
Fischer Esterification - Carboxylic Acid to Ester Under Acidic ...
Nov 16, 2022 · It was found that running the Fischer esterification using equal amounts of acetic acid and ethanol gave a 65% yield of the ester at equilibrium ...
[36]
15.7: Preparation of Esters - Chemistry LibreTexts
Sep 15, 2022 · The reaction is reversible. As a specific example of an esterification reaction, butyl acetate can be made from acetic acid and 1-butanol.
[37]
PBr3 and SOCl2 - Master Organic Chemistry
Mar 20, 2015 · Phosphorus tribromide (PBr3) and thionyl chloride (SOCl2) are useful reagents for converting alcohols to alkyl halides.
[38]
2-Butanol slowly racemizes on standing in dilute sulfuric acid. Explain.
The racemization of 2-butanol is given below: The hydroxyl oxygen is protonated and then the water molecule will be removed. Thus, it forms a planar ...
[39]
Yeast Alcohol Dehydrogenase Structure and Catalysis - PMC - NIH
ADH1 has highly preferential activity on (S)-2-butanol as compared to (R)-2-butanol, and it appears that the methyl group of (S)-2-butanol must be accommodated ...Missing: preservation | Show results with:preservation
[40]
[PDF] Locating and Estimating Sources of methyl ethyl ketone
MEK is a colorless organic liquid with an acetone-like odor. In the U.S., MEK is produced using dehydrogenation of secondary butyl alcohol (approximately 86%) ...
[41]
The dehydrogenation of 2-butanol over copper-based catalysts
The study examined 2-butanol dehydrogenation over copper catalysts, finding 15 wt.% copper on silica gave highest MEK yields. Kinetic parameters were measured ...
[42]
Methyl Ethyl Ketone Market Size, Growth & Forecast, 2030
The global Methyl Ethyl Ketone market stood at approximately 1100 thousand tonnes in 2022 and is expected to grow at a CAGR of 3.53% during the forecast period ...
[43]
Secondary Butyl Alcohol (2-Butanol) - SPS
Secondary Butyl Alcohol (2-Butanol) · Solvent for paints, coatings, varnishes, resins, gums, camphor, vegetable oils, dyes, fats, waxes, resins, shellac, rubbers ...
[44]
Production of Methyl Ethyl Ketone From Secondary Butanol - Scribd
Rating 4.2 (5) It is used as an extraction solvent for hardwood pulping and vegetable oil. 10. It is used as a solvent in pharmaceutical and cosmetic production. Table 3 shows ...
[45]
2 Butanol Market: Trends & Growth Analysis 2035 - WiseGuy Reports
Aug 4, 2025 · The 2-Butanol Market Size was valued at 3200 USD Million in 2024. The 2-Butanol Market is expected to grow from 3300 USD Million in 2025 to ...
[46]
[PDF] Substance name: sec-butyl acetate
Sep 4, 2018 · Once absorbed, sec-butyl acetate is hydrolysed by unspecific esterases to acetic acid and sec- butanol, which is further metabolized to ethyl ...Missing: extractant petrochemicals
[47]
Biocatalytic Synthesis of Chiral Alcohols and Amino Acids for ...
In this article, biocatalytic processes are described for the synthesis of chiral alcohols and unntural aminoacids for pharmaceuticals.
[48]
Biocatalytic synthesis of some chiral drug intermediates by ...
Nov 1, 1997 · Chiral intermediates were prepared by biocatalytic processes with oxidoreductases for the chemical synthesis of some pharmaceutical drug ...
[49]
WO2011001285A1 - Combustible mixed butanol fuels
The fuel additive includes a butanol and is present in an amount sufficient to improve an octane rating for the fuel composition. In an aspect, the butanol ...
[50]
https://ez.restek.com/compound/view/en/78-92-2/sec-Butanol
[51]
2-Butanol - EZGC Method Translator
ASTM D3606 Calibration Standard #3 with sec-Butanol Internal Standard, In isooctane, 1 mL/ampul. Application Chromatograms. 12 Total Show All. ASTM D3606 ...
[52]
https://pubchem.ncbi.nlm.nih.gov/compound/2-Butanol#section=Safety-and-Hazards
[53]
https://www.cdc.gov/niosh/npg/npgd0077.html
[54]
sec-Butyl alcohol - NIOSH Pocket Guide to Chemical Hazards - CDC
OSHA PEL. TWA 150 ppm (450 mg/m3) See Appendix G. Measurement Methods. NIOSH 1401 , 1405; OSHA 7. See: NMAM or OSHA Methods. Physical Description. Colorless ...
[55]
https://www.sigmaaldrich.com/US/en/sds/sial/96870
[56]
None
### Summary of 2-Butanol Safety Data Sheet (Sigma-Aldrich 96870)
[57]
[PDF] SAFETY DATA SHEET - Fisher Scientific
Jun 29, 2009 · sec-Butyl alcohol, 2-Butanol. Recommended Use. Laboratory chemicals ... Melting Point/Range. -115 °C / -175 °F. Boiling Point/Range. 99 °C ...
[58]
[PDF] Time-sensitive Chemicals - Environmental Health & Safety
Whenever possible, purchase material that contains an appropriate peroxide inhibitor or stabilizer, such as butylated hydroxytoluene (BHT) or ethanol.
[59]
[PDF] Safety Data Sheet: 2-Butanol - Carl ROTH
2-Butanol is a flammable liquid, causes serious eye irritation, may cause respiratory irritation, and may cause drowsiness or dizziness. Keep away from heat ...
[60]
2-Butanol - Substance Details - SRS | US EPA
2-Butanol. Substance Details. Systematic Name: 2-Butanol. EPA ... Formula: C4H10O. Molecular Weight: 74.12 g/mol. The IUPAC name, InChI, and structure SMILES ...
[61]
[PDF] sec-Butanol (CAS No. 78-92-2) - ECETOC
sBA contributes to the formation of tropospheric ozone, but has a low ozone creation potential. sBA is readily biodegradable and is not expected to accumulate.
[62]
[PDF] The Hydroxyl Radical Reaction Rate Constant and Atmospheric ...
OH radical concentration of 1 X 106 molecules cm-3 the atmospheric (1/e) lifetimes for 2-butanol and 2- pentanol are approximately 34 and 23 h, respectively.Missing: sec- | Show results with:sec-
[63]
[PDF] Safety Data Sheet: 2-Butanol - Carl ROTH
According to the results of its assessment, this substance is not a PBT or a vPvB. Endocrine disrupting properties. Does not contain an endocrine disruptor (ED) ...
[64]
[PDF] SAFETY DATA SHEET - Fisher Scientific
Jun 29, 2009 · Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are ...<|separator|>