2-PROPANONE

2-Propanone, commonly known as acetone, is the simplest aliphatic ketone and one of the most widely used organic solvents in laboratory and industrial settings. 
It is a colorless, volatile, and flammable liquid with exceptional solvency for a wide range of organic and some inorganic compounds. 
Historically isolated in the 17th–19th centuries as a product of fermentations and discovered as a component of acetous distillates, acetone rose to industrial prominence in the late 19th and early 20th centuries as demand for solvents and precursors to organic syntheses grew. 
The large-scale industrial production of acetone expanded dramatically during World War I and II due to its role in producing cellulose acetate and other materials.

Acetone's simple structure and reactivity make it a fundamental building block in organic synthesis, a common solvent for paints and coatings, a component in pharmaceutical and cosmetic formulations, a precursor to methyl methacrylate and bisphenol A syntheses (historically and in some routes), and a laboratory staple for cleaning and extractions.
CAS number: 67-64-1
Synonyms: acetone, propan-2-one, dimethyl ketone, β-ketopropane, 2-propanone, 2-propanone (acetone), dimethylketone, dimethylformaldehyde (historic), propanone.

Chemical structure
Acetone is a symmetrical ketone: CH₃–CO–CH₃. The carbonyl carbon is sp² hybridized, planar, and participates in conjugation with the adjacent methyl groups to a small extent through hyperconjugation. 
The resonance picture is dominated by the polarized C=O bond (partial negative charge on oxygen, partial positive on carbon).

Bond lengths and geometry
Carbonyl C=O: typical ketone bond length ~1.20 Å (slightly variable with environment).
C–C (methyl–carbonyl): ~1.52 Å.
The O atom has two lone pairs and accepts hydrogen bonds from donors (e.g., water, alcohols) but does not donate hydrogen bonds.

Electronic properties
Polar aprotic solvent: the carbonyl oxygen is a strong Lewis base site and can coordinate Lewis acids and form hydrogen bonds as acceptor.
Dipole moment: acetone possesses a substantial dipole moment (approx. 2.88 D in gas phase reported in literature), contributing to its high dielectric constant relative to alkanes.
Frontier orbitals: the LUMO has significant contribution on the carbonyl π* orbital (site for nucleophilic attack), while the HOMO involves filled lone-pair/π bonding orbitals.

Identifiers
SMILES: CC(=O)C
InChI: InChI=1S/C3H6O/c1-3(2)4/h1-2H3 (canonical InChI varies by source)

Physical properties and phase behavior
Below are the typical physical property values commonly used for formulations, engineering, and laboratory practice. 
Exact values can vary slightly with temperature, purity, and measurement technique.

Key physical constants (typical literature values)
Appearance: colorless, volatile liquid
Odor: characteristic, sweetish, ketonic
Boiling point (1 atm): ~56.0 °C
Melting point: ~−94 to −95 °C
Density (20 °C): ~0.784–0.79 g·cm⁻³
Vapor pressure (20 °C): high volatility (substantial vapor pressure; commonly reported values ~200–300 mmHg at 20 °C — consult product spec for exact values)
Flash point: typically highly flammable; closed cup flash point around −20 °C to −18 °C depending on method
Autoignition temperature: high (several hundred °C; reported values often in the 430–540 °C range depending on source)
Solubility: miscible with water in all proportions; mixes with most organic solvents (alcohols, ethers, esters, chloroform, benzene, etc.)
Refractive index (20 °C): ~1.358–1.359
Dielectric constant (20–25 °C): moderate (approx. 20.7 at 20 °C) — this value explains its effectiveness dissolving both polar and nonpolar solutes.

Phase behavior
Acetone is fully miscible with water over all proportions.
It forms azeotropes with some solvents (e.g., with water it does not form a constant boiling binary azeotrope at atmospheric pressure in the same sense as some solvents do; however acetone–water mixtures show composition-dependent boiling behavior and require specific fractional distillation considerations).
Vapor density greater than air? Acetone vapor is slightly heavier than air (air = 1.0), but in practical settings vapor distribution depends on ventilation and temperature.

Spectroscopic and analytical signatures

Infrared (IR) spectroscopy
Strong carbonyl stretch (C=O) near ~1705–1715 cm⁻¹ (typical ketone band; exact position influenced by solvent and concentration).
C–H stretches (methyl) near ~2960–2870 cm⁻¹.
Lack of O–H stretch (no OH), unless hydrates/contaminants present.

Nuclear Magnetic Resonance (NMR)
¹H NMR (CDCl₃): singlet for the two equivalent methyl groups ~δ 2.1–2.2 ppm (six protons total, equivalent by symmetry). No other proton signals in pure acetone.
¹³C NMR: carbonyl carbon appears downfield ~δ 206–207 ppm; methyl carbons near δ 26–30 ppm.

Mass spectrometry (electron ionization)
M⁺• (molecular ion) at m/z 58 (base molecular mass 58). Fragmentation gives common peaks at m/z 43 (acyl fragment, C₃H₇⁺) and m/z 15 (methyl).

Ultraviolet–visible (UV–Vis)
Acetone has no strong chromophore in the visible region; weak n→π* transitions may be observed in the UV (below 300 nm), but acetone is effectively transparent in visible light.

Other analytical techniques
Gas chromatography (GC) with flame ionization detection (FID) or mass spectrometry (MS) is commonly used for purity and residual solvent analysis.
Headspace GC is used for volatile quantification in formulations.
Karl Fischer titration is not applicable; acetone contains no water of constitution but affects Karl Fischer measurements if water is present.

Thermodynamic and transport properties

Thermodynamic data (representative)
Standard enthalpy of formation (gas, ΔH°f): approximately −248.4 kJ·mol⁻¹ (literature values vary by source and phase).
Enthalpy of vaporization (ΔHvap) at boiling point: on the order of 30–35 kJ·mol⁻¹.
Heat capacity (Cp): depends on phase and temperature; for gas and liquid phases consult tabulated data for engineering calculations.

Transport properties
Viscosity (liquid, 20 °C): low (≈0.3–0.35 mPa·s), facilitating rapid diffusion and mixing.
Diffusivity in air: high relative to heavier solvents, enabling rapid vapor dispersal.

Thermochemical behavior
Acetone is thermally stable at moderate temperatures but will oxidize at high temperatures and can decompose under severe conditions to form light gases. 
It is compatible with many process conditions but care is required in reactions generating peroxides or with strong oxidizers.

Chemical reactivity and key reactions

Acetone's chemistry centers on the carbonyl functional group and the α-carbon positions (the methyl groups adjacent to C=O). 
It participates in a wide range of organic reactions:

Acid- and base-catalyzed enolization / enolate chemistry
Formation of enol and enolate ions under acidic or basic catalysis; enolate chemistry enables aldol reactions, Michael additions, alkylation at α positions, and Robinson annulations.

Self-condensation (aldol) under basic conditions yields diacetone alcohol and, upon dehydration, mesityl oxide and further condensates. 
These side reactions are important in production and purification (must be controlled).

Nucleophilic additions to the carbonyl
Typical carbonyl chemistry: addition of hydrides (e.g., reductions with NaBH₄, LiAlH₄) to give isopropanol; formation of imines/oximes with amines/hydroxylamine.

Reaction with organometallic reagents: Grignards add to yield tertiary alcohols after workup (reaction control needed: acetone is usually incompatible with strong nucleophiles used to form those reagents unless carefully controlled).

Oxidation and reduction
Reduction → isopropanol (industrial hydrogenation or chemical reduction).
Oxidation → cleavage under severe oxidation gives acetic acid, CO₂, or small fragments depending on conditions; mild oxidation produces acetate under certain catalytic conditions.

Condensation and polymerization
Under acid or base catalysis, acetone can condense with other carbonyl compounds; polymerization is not common under normal storage, but in presence of strong acids or bases and heat, oligomeric by-products may form.

Halogenation / functionalization
α-halogenation can occur under enol/enolate pathways to form α-halo ketones (synthetically useful intermediates).

Complexation and coordination
Acetone can act as a ligand to Lewis acids and coordinate to metal centers (e.g., in metal–acetone adducts). 
It easily solvates many salts and reagents.

Industrial production and synthesis routes

Main industrial route (cumene process byproduct & direct methods)
Historically, acetone was produced via dry distillation of acetates (like Kermes and other older processes) and by fermentation. 
Modern industrial production primarily uses the following methods:
Cumene (Hock) process: phenol and acetone are co-produced by acid-catalyzed cumene hydroperoxide cleavage (cumene process) — acetone is a major coproduct of phenol manufacture in this route. 
This remains a dominant industrial source because it integrates with phenol demand.
Direct oxidation of isopropylbenzene followed by hydroperoxide decomposition (the cumene route detail).
Propene oxidation and other petrochemical routes: alternative routes involve catalytic oxidation or partial oxidation of hydrocarbons and other petrochemical feedstocks, but the cumene process dominates large-scale production.
Fermentation (historical / small scale): acetone–butanol–ethanol (ABE) fermentation by Clostridium acetobutylicum produces acetone and butanol; historically important, now niche or renewable route interest.

Purification
Industrial crude acetone is purified by fractional distillation, using dehydration and removal of higher boiling impurities and condensates (e.g., diacetone alcohol, mesityl oxide). 
Adsorptive and membrane methods are used for specialty grades.

Quality grades
Commercial grades: reagent grade, solvent grade, anhydrous (water ≤ 50 ppm or specific), pharmaceutical grade (meeting pharmacopeial standards), technical grades with varying impurity profiles.

SAFETY INFORMATION ABOUT 2-PROPANONE

First aid measures:
Description of first aid measures:
General advice:
Consult a physician. 
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
 
If inhaled:
If breathed in, move person into fresh air. 
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately. 
Wash off with soap and plenty of water.
Consult a physician.
 
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
 
If swallowed:
Do NOT induce vomiting. 
Never give anything by mouth to an unconscious person. 
Rinse mouth with water. 
Consult a physician.
 
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
 
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. 
 
Avoid breathing vapours, mist or gas. 
Evacuate personnel to safe areas.
 
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
 
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste. 
Keep in suitable, closed containers for disposal.
 
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
 
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place. 
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
 
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
 
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles. 
Faceshield (8-inch minimum). 
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
 
Skin protection:
Handle with gloves. 
Gloves must be inspected prior to use. 
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product. 
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. 
Wash and dry hands.
 
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
 
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. 
 
If the respirator is the sole means of protection, use a full-face supplied air respirator. 
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. 
Do not let product enter drains.
Discharge into the environment must be avoided.
 
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions. 
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
 
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company. 
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product