Acetone^[1]

Names
IUPAC name Acetone[7]
Preferred IUPAC name Propan-2-one[8]
Systematic IUPAC name 2-Propanone
Other names Acetonum (Latin pronunciation: [aˈkeːtonum]) Dimethyl ketone[2] Dimethyl carbonyl Ketone propane[3] β-Ketopropane[2] Propanone[4] 2-Propanone[2] Pyroacetic spirit (archaic)[5] Spirit of Saturn (archaic)[6]
Identifiers
CAS Number	67-64-1 Y
3D model (JSmol)	Interactive image
3DMet	B00058
Beilstein Reference	635680
ChEBI	CHEBI:15347 Y
ChEMBL	ChEMBL14253 Y
ChemSpider	175 Y
ECHA InfoCard	100.000.602
EC Number	200-662-2
Gmelin Reference	1466
KEGG	D02311 Y
MeSH	Acetone
PubChem CID	180
RTECS number	AL3150000
UNII	1364PS73AF Y
UN number	1090
CompTox Dashboard (EPA)	DTXSID8021482
InChI InChI=1S/C3H6O/c1-3(2)4/h1-2H3 Y Key: CSCPPACGZOOCGX-UHFFFAOYSA-N Y InChI=1/C3H6O/c1-3(2)4/h1-2H3 Key: CSCPPACGZOOCGX-UHFFFAOYAF
SMILES CC(=O)C
Properties
Chemical formula	C3H6O
Molar mass	58.080 g·mol−1
Appearance	Colourless liquid
Odor	Pungent, fruity[9]
Density	0.7845 g/cm3 (25 °C)[10]
Melting point	−94.9 °C (−138.8 °F; 178.2 K)[10]
Boiling point	56.08 °C (132.94 °F; 329.23 K)[10]
Solubility in water	Miscible[10]
Solubility	Miscible in benzene, diethyl ether, methanol, chloroform, ethanol[10]
log P	−0.24[11]
Vapor pressure	9.39 kPa (0 °C) 30.6 kPa (25 °C) 374 kPa (100 °C) 2.8 MPa (200 °C)[2]
Acidity (pKa)	19.16 (H2O)[12] 26.5 (DMSO)[13]
Magnetic susceptibility (χ)	−33.8·10−6 cm3/mol[14]
Thermal conductivity	0.161 W/(m·K) (25 °C)[15]
Refractive index (nD)	1.3588 (20 °C)[10]
Viscosity	0.306 mPa·s (25 °C)[16]
Structure
Coordination geometry	Trigonal planar at C2
Molecular shape	Dihedral at C2
Dipole moment	2.88 D[17]
Thermochemistry[18]
Heat capacity (C)	126.3 J/(mol·K)
Std molar entropy (S⦵298)	199.8 J/(mol·K)
Std enthalpy of formation (ΔfH⦵298)	−248.4 kJ/mol
Std enthalpy of combustion (ΔcH⦵298)	−1.79 MJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Highly flammable
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H319, H336, H373
Precautionary statements	P210, P235, P260, P305+P351+P338
NFPA 704 (fire diamond)	1 3 0
Flash point	−20 °C (−4 °F; 253 K)[19]
Autoignition temperature	465[19] °C (869 °F; 738 K)
Explosive limits	2.5–12.8%[19]
Threshold limit value (TLV)	250 ppm[20] (STEL), 500 ppm[20] (C)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	5800 mg/kg (rat, oral) 3000 mg/kg (mouse, oral) 5340 mg/kg (rabbit, oral)[21]
LC50 (median concentration)	20,702 ppm (rat, 8 h)[21]
LCLo (lowest published)	45,455 ppm (mouse, 1 h)[21]
NIOSH (US health exposure limits):
PEL (Permissible)	1000 ppm (2400 mg/m3)[3]
REL (Recommended)	TWA 250 ppm (590 mg/m3)[3]
IDLH (Immediate danger)	2500 ppm[3]
Related compounds
Related compounds	Butanone Isopropyl alcohol Formaldehyde Urea Carbonic acid
Supplementary data page
Acetone (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is YN ?) Infobox references

Acetone (2-propanone or dimethyl ketone) is an organic compound with the formula (CH₃)₂CO.^[22] It is the simplest and smallest ketone (>C=O). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odor.

Acetone is miscible with water and serves as an important organic solvent in industry, home, and laboratory. About 6.7 million tonnes were produced worldwide in 2010, mainly for use as a solvent and for production of methyl methacrylate and bisphenol A, which are precursors to widely used plastics.^[23][24] It is a common building block in organic chemistry. It serves as a solvent in household products such as nail polish remover and paint thinner. It has volatile organic compound (VOC)-exempt status in the United States.^[25]

Acetone is produced and disposed of in the human body through normal metabolic processes. It is normally present in blood and urine. People with diabetic ketoacidosis produce it in larger amounts. Ketogenic diets that increase ketone bodies (acetone, β-hydroxybutyric acid and acetoacetic acid) in the blood are used to counter epileptic attacks in children who suffer from refractory epilepsy.^[26]

Name

From the 17th century and before modern developments in organic chemistry nomenclature, acetone was given many different names. Those names include spirit of Saturn, which was given when it was thought to be a compound of lead, and later pyro-acetic spirit and pyro-acetic ester.^[6]

Prior to the "acetone" name given by Antoine Bussy, it was named "mesit" (from the Greek μεσίτης, meaning mediator) by Carl Reichenbach who also claimed that methyl alcohol consisted of mesit and ethyl alcohol.^[27][6] Names derived from mesit include mesitylene and mesityl oxide which were first synthesised from acetone.

Unlike many compounds with the acet- prefix having a 2-carbon chain, acetone has a 3-carbon chain which has caused confusion since there cannot be a ketone with 2 carbons. The prefix refers to acetone's relation to vinegar (acetum in Latin, also the source of the words "acid" and "acetic"), rather than its chemical structure.^[28]

History

Acetone was first produced by Andreas Libavius in 1606 by distillation of lead(II) acetate.^[29][30]

In 1832, French chemist Jean-Baptiste Dumas and German chemist Justus von Liebig determined the empirical formula for acetone.^[31][32] In 1833, French chemists Antoine Bussy and Michel Chevreul decided to name acetone by adding the suffix -one to the stem of the corresponding acid (viz, acetic acid) just as a similarly prepared product of what was then confused with margaric acid was named margarone.^[33][28] By 1852, English chemist Alexander William Williamson realized that acetone was methyl acetyl;^[34] the following year, the French chemist Charles Frédéric Gerhardt concurred.^[35] In 1865, the German chemist August Kekulé published the modern structural formula for acetone.^[36][37] Johann Josef Loschmidt had presented the structure of acetone in 1861,^[38] but his privately published booklet received little attention. During World War I, Chaim Weizmann developed the process for industrial production of acetone (Weizmann Process).^[39]

Production

In 2010, the worldwide production capacity for acetone was estimated at 6.7 million tonnes per year.^[40] With 1.56 million tonnes per year, the United States had the highest production capacity,^[41] followed by Taiwan and mainland China. The largest producer of acetone is INEOS Phenol, owning 17% of the world's capacity, with also significant capacity (7–8%) by Mitsui, Sunoco and Shell in 2010.^[40] INEOS Phenol also owns the world's largest production site (420,000 tonnes/annum) in Beveren (Belgium). Spot price of acetone in summer 2011 was 1100–1250 USD/tonne in the United States.^[42]

Current method

Acetone is produced directly or indirectly from propene. Approximately 83% of acetone is produced via the cumene process;^[24] as a result, acetone production is tied to phenol production. In the cumene process, benzene is alkylated with propylene to produce cumene, which is oxidized by air to produce phenol and acetone:

Other processes involve the direct oxidation of propylene (Wacker-Hoechst process), or the hydration of propylene to give 2-propanol, which is oxidized (dehydrogenated) to acetone.^[24]

Older methods

Previously, acetone was produced by the dry distillation of acetates, for example calcium acetate in ketonic decarboxylation.

${\displaystyle \text{Ca}{({\text{CH}}_3^{}\text{COO})}_2^{}⟶<!--\; ⟶\; -->{\text{CaO}}_{(\text{s})}^{}+{\text{CO}}_{2(\text{g})}^{}+{({\text{CH}}_3^{}}_{}^{}}$Zdroj:https://en.wikipedia.org?pojem=Acetone
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