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.
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| Names | |
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| Preferred IUPAC name
Pentan-3-one | |
| Other names
Diethyl ketone, diethylketone, 3-pentanone, dimethyl acetone, propione, DEK, metacetone, methacetone, ethyl ketone fraction
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.002.265 |
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PubChem CID
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| RTECS number |
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| UNII | |
| UN number | 1156 |
CompTox Dashboard (EPA)
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| Properties | |
| C5H10O | |
| Molar mass | 86.134 g·mol−1 |
| Appearance | Colorless 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: | |
 
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| 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)
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none[1] |
REL (Recommended)
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TWA 200 ppm (705 mg/m3)[1] |
IDLH (Immediate danger)
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N.D.[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Uses
edit3-Pentanone is primarily used as starting material in chemical synthesis. A major application is in the industrial synthesis of vitamin E.[3][4] It has also been used in the synthesis of Oseltamivir (Tamiflu).
3-Pentanone itself finds some use as a specialty solvent in paint, although it is less common than butanone.
Syntheses
editKetonic decarboxylation route
edit3-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.[5]
Carbonylation route
editIt can also be prepared by combining ethylene, CO, and H2.[4] 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[6] 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.[7]
Safety
editThe TLV value for 3-pentanone is 200 ppm (705 mg/m3).[4] 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.[8]
See also
editReferences
edit- ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0212". National Institute for Occupational Safety and Health (NIOSH).
- ^ a b c d e Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ Müller, Marc-André; Schäfer, Christian; Litta, Gilberto; Klünter, Anna-Maria; Traber, Maret G.; Wyss, Adrian; Ralla, Theo; Eggersdorfer, Manfred; Bonrath, Werner (6 December 2022). "100 Years of Vitamin E: From Discovery to Commercialization" (PDF). European Journal of Organic Chemistry. 2022 (45). doi:10.1002/ejoc.202201190.
- ^ a b c 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
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Chemicals & Laboratory Equipment, Material Safety Data Sheet for 3-pentanone Archived 2010-01-02 at the Wayback Machine, ScienceLab.com, updated 11/06/2008