3-Pentanone

Last updated
3-Pentanone
3-Pentanone structure.svg
3-Pentanone-3D-balls.png
Names
Preferred IUPAC name
Pentan-3-one
Other names
Diethyl ketone, diethylketone, 3-pentanone, dimethyl acetone, propione, DEK, metacetone, methacetone, ethyl ketone fraction
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.265 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-490-3
PubChem CID
RTECS number
  • SA8050000
UNII
UN number 1156
  • InChI=1S/C5H10O/c1-3-5(6)4-2/h3-4H2,1-2H3 Yes check.svgY
    Key: FDPIMTJIUBPUKL-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C5H10O/c1-3-5(6)4-2/h3-4H2,1-2H3
    Key: FDPIMTJIUBPUKL-UHFFFAOYAJ
  • O=C(CC)CC
Properties
C5H10O
Molar mass 86.134 g·mol−1
AppearanceColorless liquid [1]
Odor Acetone-like [2]
Density 0.81 g/cm3 at 20 °C [2]
Melting point −39 °C (−38 °F; 234 K) [2]
Boiling point 102 °C (216 °F; 375 K) [2]
35 g/L [2]
Vapor pressure 35 mmHg [1]
-58.14·10−6 cm3/mol
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Danger
H225, H335, H336
P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P340, P312, P370+P378, P403+P233, P403+P235, P405, P501
Flash point 12.78 °C (55.00 °F; 285.93 K)
425 °C (797 °F; 698 K)
Explosive limits 1.6%-6.4% [1]
NIOSH (US health exposure limits):
PEL (Permissible)
none [1]
REL (Recommended)
TWA 200 ppm (705 mg/m3) [1]
IDLH (Immediate danger)
N.D. [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

3-Pentanone (also known as diethyl ketone) is a simple, symmetrical dialkyl ketone. It is a colorless liquid ketone with an odor like that of acetone. It is soluble in about 25 parts water, but miscible with organic solvents.

Contents

Uses

It is mainly used as a solvent in paint and a precursor to vitamin E. [3]

Syntheses

Ketonic decarboxylation route

3-Pentanone is produced by ketonic decarboxylation of propanoic acid using metal oxide catalysts:

2 CH3CH2CO2H → (CH3CH2)2CO + CO2 + H2O

in the laboratory, the reaction can be conducted in a tube furnace. [4]

Carbonylation route

It can also be prepared by combining ethylene, CO, and H2. [3] When the reaction is catalyzed by dicobalt octacarbonyl, water can be used as a source of hydrogen. A proposed intermediate is the ethylene-propionyl species [CH3C(O)Co(CO)3(ethylene)] which undergoes a migratory insertion to form [CH3COCH2CH2Co(CO)3]. The required hydrogen arises from the water shift reaction. For details, see [5] If the water shift reaction is not operative, the reaction affords a polymer containing alternating carbon monoxide and ethylene units. Such aliphatic polyketones are more conventionally prepared using palladium catalysts. [6]

Safety

The TLV value for 3-pentanone is 200 ppm (705 mg/m3). [3] 3-pentanone can be hazardous if it comes in contact with the skin or eyes, and can cause irritation of the skin and redness, watering, and itching of the eyes. This chemical can also cause nervous system or organ damage if ingested. Although considered stable, 3-pentanone is extremely flammable if exposed to flame, sparks, or another source of heat. For safety, it should be stored in a flammable materials cabinet away from heat or sources of ignition, preferably in a cool, well-ventilated area. [7]

See also

Related Research Articles

Butanone Chemical compound

Butanone, also known as ethyl methyl ketone, is an organic compound with the formula CH3C(O)CH2CH3. This colourless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.

Tetrahydrofuran Chemical compound

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent.

Ethylene oxide Chemical compound

Ethylene oxide is an organic compound with the formula C
2
H
4
O
. It is a cyclic ether and the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintly sweet odor. Because it is a strained ring, ethylene oxide easily participates in a number of addition reactions that result in ring-opening. Ethylene oxide is isomeric with acetaldehyde and with vinyl alcohol. Ethylene oxide is industrially produced by oxidation of ethylene in the presence of silver catalyst.

Methyl ethyl ketone peroxide (MEKP) is an organic peroxide with the formula [(CH3)(C2H5)C(O2H)]2O2. MEKP is a colorless oily liquid. It is widely used in vulcanization (crosslinking) of polymers.

Diethyl ether Organic chemical compound

Diethyl ether, or simply ether, is an organic compound in the ether class with the formula (C
2
H
5
)
2
O
, sometimes abbreviated as Et
2
O
. It is a colourless, highly volatile, sweet-smelling, extremely flammable liquid. It is commonly used as a solvent in laboratories and as a starting fluid for some engines. It was formerly used as a general anesthetic, until non-flammable drugs were developed, such as halothane. It has been used as a recreational drug to cause intoxication.

Cyclohexanol Chemical compound

Cyclohexanol is the organic compound with the formula HOCH(CH2)5. The molecule is related to cyclohexane by replacement of one hydrogen atom by a hydroxyl group. This compound exists as a deliquescent colorless solid with a camphor-like odor, which, when very pure, melts near room temperature. Billions of kilograms are produced annually, mainly as a precursor to nylon.

Hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes from alkenes. This chemical reaction entails the net addition of a formyl group (CHO) and a hydrogen atom to a carbon-carbon double bond. This process has undergone continuous growth since its invention: Production capacity reached 6.6×106 tons in 1995. It is important because aldehydes are easily converted into many secondary products. For example, the resulting aldehydes are hydrogenated to alcohols that are converted to detergents. Hydroformylation is also used in speciality chemicals, relevant to the organic synthesis of fragrances and drugs. The development of hydroformylation is one of the premier achievements of 20th-century industrial chemistry.

Methylamine is an organic compound with a formula of CH3NH2. This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine.

Ethyl acetate Chemical compound

Ethyl acetate is the organic compound with the formula CH3−COO−CH2−CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and in the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

In chemistry, homogeneous catalysis is catalysis by a soluble catalyst in a solution. Homogeneous catalysis refers to reactions where the catalyst is in the same phase as the reactants, principally in solution. In contrast, heterogeneous catalysis describes processes where the catalysts and substrate are in distinct phases, typically solid-gas, respectively. The term is used almost exclusively to describe solutions and implies catalysis by organometallic compounds. Homogeneous catalysis is established technology that continues to evolve. An illustrative major application is the production of acetic acid. Enzymes are examples of homogeneous catalysts.

Dimethoxyethane Chemical compound

Dimethoxyethane, also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve, and DME, is a colorless, aprotic, and liquid ether that is used as a solvent, especially in batteries. Dimethoxyethane is miscible with water.

2-Butanol Secondary alcohol

2-Butanol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. Its structural isomers are 1-butanol. isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-2-butanol and (S)-(+)-2-butanol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

Cyclohexanone Chemical compound

Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oil has an odor reminiscent of that of acetone. Over time, samples of cyclohexanone assume a yellow color. Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Billions of kilograms are produced annually, mainly as a precursor to nylon.

The chemical compound 1,2-dichloroethane, commonly known as ethylene dichloride (EDC), is a chlorinated hydrocarbon. It is a colourless liquid with a chloroform-like odour. The most common use of 1,2-dichloroethane is in the production of vinyl chloride, which is used to make polyvinyl chloride (PVC) pipes, furniture and automobile upholstery, wall coverings, housewares, and automobile parts. 1,2-Dichloroethane is also used generally as an intermediate for other organic chemical compounds, and as a solvent. It forms azeotropes with many other solvents, including water and other chlorocarbons.

Methyl isobutyl ketone Chemical compound

Methyl isobutyl ketone (MIBK) is the common name for the organic compound 4-methylpentan-2-one, condensed chemical formula (CH3)2CHCH2C(O)CH3. This colourless liquid, a ketone, is used as a solvent for gums, resins, paints, varnishes, lacquers, and nitrocellulose.

Isobutanol Chemical compound

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.

Propan-1-ol Primary alcohol compound

Propan-1-ol is a primary alcohol with the formula CH3CH2CH2OH and sometimes represented as PrOH or n-PrOH. It is a colorless liquid and an isomer of 2-propanol. It is formed naturally in small amounts during many fermentation processes and used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.

Ethylamine, also known as ethanamine, is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It condenses just below room temperature to a liquid miscible with virtually all solvents. It is a nucleophilic base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis.

Isopropyl alcohol is a colorless, flammable chemical compound with a strong odor. As an isopropyl group linked to a hydroxyl group, it is the simplest example of a secondary alcohol, where the alcohol carbon atom is attached to two other carbon atoms. It is a structural isomer of 1-propanol and ethyl methyl ether.

References

  1. 1 2 3 4 5 6 NIOSH Pocket Guide to Chemical Hazards. "#0212". National Institute for Occupational Safety and Health (NIOSH).
  2. 1 2 3 4 5 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. 1 2 3 Hardo Siegel, Manfred Eggersdorfer "Ketones" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2002 by Wiley-VCH, Wienheim. doi : 10.1002/14356007.a15_077
  4. Furniss, Brian; Hannaford, Antony; Smith, Peter & Tatchell, Austin (1996). Vogel's Textbook of Practical Organic Chemistry (5th ed.). London: Longman Science & Technical. p.  613. ISBN   9780582462366.
  5. Murata K.; Matsuda A. (1981). "Application of Homogeneous Water-Gas Shift Reaction III Further Study of the Hydrocarbonylation – A highly Selective Formation of Diethyl Keton from Ethene, CO and H2O". Bulletin of the Chemical Society of Japan . 54 (7): 2089–2092. doi: 10.1246/bcsj.54.2089 .
  6. J. Liu; B.T. Heaton; J.A. Iggo & R. Whyman (2004). "The Complete Delineation of the Initiation, Propagation, and Termination Steps of the Carbomethoxy Cycle for the Carboalkoxylation of Ethene by Pd–Diphosphane Catalysts". Angew. Chem. Int. Ed. 43 (1): 90–94. doi:10.1002/anie.200352369. PMID   14694480.
  7. Chemicals & Laboratory Equipment, Material Safety Data Sheet for 3-pentanone Archived 2010-01-02 at the Wayback Machine , ScienceLab.com, updated 11/06/2008