2-pentanone

Structural formula
General
Surname	2-pentanone
other names	Pentan-2-one; Methyl propyl ketone; PENTANONE ( INCI ) ;
Molecular formula	C 5 H 10 O
Brief description	volatile, highly flammable, colorless liquid with an acetone-like odor
External identifiers / databases
EC number	203-528-1
ECHA InfoCard	100.003.208
PubChem	7895
Wikidata	Q209460
properties
Molar mass	86.13 g mol −1
Physical state	liquid
density	0.81 g cm −3
Melting point	−78 ° C
boiling point	102 ° C
Vapor pressure	37 h Pa (20 ° C); 283 hPa (65 ° C);
solubility	moderate in water (43 g l −1 at 20 ° C)
Refractive index	1.389-1.391
safety instructions
H and P phrases	H: 225-302-319
	P: 210-301 + 312 + 330-305 + 351 + 338-370 + 378-403 + 235
MAK	Switzerland: 200 ml m −3 or 700 mg m −3
Toxicological data	3730 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

2-pentanone is a chemical compound from the ketone group . It is in the form of a colorless liquid with an odor similar to acetone and is isomeric to 3-pentanone and methyl isopropyl ketone .

Extraction and presentation

2-pentanone can e.g. B. obtained from acetoacetic ester . It is also produced by the oxidation of 2-pentanol .

properties

2-Pentanone is a colorless liquid with an acetone-like odor. The boiling point at normal pressure is 102 ° C. According to Antoine, the vapor pressure function results from log ₁₀ (P) = A− (B / (T + C)) (P in bar, T in ° C) with A = 4.14243, B = 1311.145 and C = - 58.457 in the temperature range between 329.8 and 384.8 K. The miscibility with water is limited. As the temperature rises, the solubility of 2-pentanone in water decreases or the solubility of water in 2-pentanone increases.

Miscibility between 2-pentanone and water
temperature	° C	0	9.7	19.7	31.0	39.6	49.8	60.1	70.2	80.0	90.5
2-pentanone in water	in%	8.7	6.9	5.9	5.0	4.6	4.2	4.0	4.0	3.8	3.4
Water in 2-pentanone	in%	2.57	2.92	3.19	3.48	4.13	4.17	5.13	4.86	4.72	5.28

2-Pentanone forms highly flammable vapor-air mixtures with air. The compound has a flash point below 7 ° C. The explosion range is between 1.5 vol.% (53 g / m ³ ) as the lower explosion limit (LEL) and 8.2 vol.% (300 g / m ³ ) as the upper explosion limit (UEL). Correlating the explosion limits with the vapor pressure function results in a lower explosion point of 4 ° C. The limit gap width was determined to be 0.99 mm. This results in an assignment to explosion group IIA. The ignition temperature is 445 ° C. The substance therefore falls into temperature class T2.

use

2-Pentanone is used as a solvent , for organic synthesis and as an odorous substance with a fruity, banana-like odor. By reductive amination with ammonia and hydrogen as a reducing agent in the presence of a nickel - catalyst can be 2-pentylamine are obtained.

Web links

National Institute of Standards and Technology: Physical data on 2-Pentanone

Individual evidence

↑ Entry on PENTANONE in the CosIng database of the EU Commission, accessed on March 11, 2020.
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p Entry on 2-pentanone in the GESTIS substance database of the IFA , accessed on April 10, 2018(JavaScript required) .
↑ Entry on 2-Pentanone at ChemBlink , accessed on February 25, 2011.
↑ Swiss Accident Insurance Fund (Suva): Limits - Current MAK and BAT values (search for 107-87-9 or 2-pentanone ), accessed on November 2, 2015.
↑ ^a ^b Entry on 2-pentanone at The Good Scents Company , accessed June 18, 2017.
^ OC seminar pages from Peet, University of Düsseldorf: 8th exercise sheet: Carbonyl compounds II ( Memento from March 5, 2000 in the Internet Archive ).
↑ ^a ^b Collerson, RR; Counsel, JF; Handley, R .; Martin, JF; Sprake, CHS: Thermodynamic Properties of Organic Oxygen Compounds. Part XV. Purification and Vapor Pressures of Some Ketones and Ethers in J. Chem. Soc. 1965, 3697-3700, doi : 10.1039 / jr9650003697 .
^ ^A ^b R. M. Stephenson: Mutual Solubilities: Water-Ketones, Water-Ethers, and Water-Gasoline-Alcohols in J. Chem. Eng. Data 37 (1992) 80-95, doi: 10.1021 / je00005a024 .
↑ ^a ^b ^c Sorbe - Safety-related characteristics of chemical substances, 131. Supplementary delivery 8/2009, ecomed-Verlag.
↑ Joseph A. Alvarez, Pauline Beard, R. Chasnov, AP Davis, LA Giesmann, GF Greif, TM Hagle, M. Hankins, Thomas C. Kennedy, James S. Malek, MR Murnik, JC Norman, JG Robison, GW Sheldon , WL Stone, B. Swyhart, GD Thomas, WC Uhland, WF Wachol: Mcat, The Best Test Preparation For The Medical College Admission Test . Research & Education Assoc., 2004, ISBN 0-7386-0034-2 , pp. 145 ( limited preview in Google Book search).

[CosIng-1] Entry on PENTANONE in the CosIng database of the EU Commission, accessed on March 11, 2020.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p Entry on 2-pentanone in the GESTIS substance database of the IFA , accessed on April 10, 2018(JavaScript required) .

[3] Entry on 2-Pentanone at ChemBlink , accessed on February 25, 2011.

[4] Swiss Accident Insurance Fund (Suva): Limits - Current MAK and BAT values (search for 107-87-9 or 2-pentanone ), accessed on November 2, 2015.

[goodscents-5] Entry on 2-pentanone at The Good Scents Company , accessed June 18, 2017.

[6] OC seminar pages from Peet, University of Düsseldorf: 8th exercise sheet: Carbonyl compounds II ( Memento from March 5, 2000 in the Internet Archive ).

[Collerson-7] Collerson, RR; Counsel, JF; Handley, R .; Martin, JF; Sprake, CHS: Thermodynamic Properties of Organic Oxygen Compounds. Part XV. Purification and Vapor Pressures of Some Ketones and Ethers in J. Chem. Soc. 1965, 3697-3700, doi : 10.1039 / jr9650003697 .

[Stephenson-8] A ^b R. M. Stephenson: Mutual Solubilities: Water-Ketones, Water-Ethers, and Water-Gasoline-Alcohols in J. Chem. Eng. Data 37 (1992) 80-95, doi: 10.1021 / je00005a024 .

[Sorbe-9] Sorbe - Safety-related characteristics of chemical substances, 131. Supplementary delivery 8/2009, ecomed-Verlag.

[W._F._Wachol-10] Joseph A. Alvarez, Pauline Beard, R. Chasnov, AP Davis, LA Giesmann, GF Greif, TM Hagle, M. Hankins, Thomas C. Kennedy, James S. Malek, MR Murnik, JC Norman, JG Robison, GW Sheldon , WL Stone, B. Swyhart, GD Thomas, WC Uhland, WF Wachol: Mcat, The Best Test Preparation For The Medical College Admission Test . Research & Education Assoc., 2004, ISBN 0-7386-0034-2 , pp. 145 ( limited preview in Google Book search).