3-pentanone

Structural formula
General
Surname	3-pentanone
other names	Pentan-3-one; Amyl ketone; Dimethylacetone; Diethyl ketone; Propionone; Propion; Metacetone; DEK; DIETHYL KETONE ( INCI ) ;
Molecular formula	C 5 H 10 O
Brief description	volatile, highly flammable, colorless liquid with a sweet, acetone-like odor
External identifiers / databases
EC number	202-490-3
ECHA InfoCard	100.002.265
PubChem	7288
Wikidata	Q223112
properties
Molar mass	86.13 g · mol -1
Physical state	liquid
density	0.81 g cm −3
Melting point	−39 ° C
boiling point	102 ° C
Vapor pressure	500 h Pa (80.3 ° C)
solubility	soluble in water (35 g l −1 at 25 ° C); miscible with ethanol and diethyl ether;
Refractive index	1.3905 (25 ° C)
safety instructions
H and P phrases	H: 225-335-336-319
	EUH: 066
	P: 210-305 + 351 + 338-261-304 + 340-312-403 + 233
MAK	Switzerland: 200 ml m −3 or 705 mg m −3
Toxicological data	2140 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

3-Pentanone is a colorless liquid with a sweet, acetone-like odor and belongs to the ketone class of compounds .

Extraction and presentation

3-Pentanone can be obtained by hydroformylating ethene with carbon monoxide and hydrogen . The selectivity between the two possible products (3-pentanone and propanal ) can be shifted towards 3-pentanone through the choice of suitable catalysts and conditions.

Another synthetic route involves the conversion of propionic acid with manganese dioxide as a catalyst.

It is also produced by the oxidation of 3-pentanol .

properties

3-Pentanone is a colorless liquid that boils at 102 ° C under normal pressure . According to Antoine, the vapor pressure function results from log ₁₀ (P) = A− (B / (T + C)) (P in bar, T in K) with A = 4.14917, B = 1309.653 and C = −59.032 in the temperature range from 330 to 484 K. The miscibility with water is limited. As the temperature rises, the solubility of 3-pentanone in water decreases or the solubility of water in 3-pentanone increases.

Miscibility between 3-pentanone and water
Temperature ° C		0	9.7	19.3	30.6	40.3	50.0	60.1	70.1	80.2	90.5
3-pentanone in water	in%	7.68	6.25	5.30	4.24	3.86	3.62	3.43	3.30	3.16
Water in 3-pentanone	in%	1.57	1.77	2.00	2.51	2.49	2.81	2.98	2.99	3.69	4.10

The ketone forms highly flammable vapor-air mixtures. The compound has a flash point of 6 ° C. The explosion range is between 1.6 vol.% As the lower explosion limit (LEL) and 7.7 vol.% As the upper explosion limit (UEL). The limit gap width was determined to be 0.88 mm (50 ° C). This results in an assignment to explosion group IIA. The ignition temperature is 455 ° C. The substance therefore falls into temperature class T2.

use

3-Pentanone is used as a solvent and for organic synthesis.

Individual evidence

↑ Entry on DIETHYLKETONE in the CosIng database of the EU Commission, accessed on March 21, 2020.

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o Entry on 3-pentanone in the GESTIS substance database of the IFA , accessed on April 10, 2018(JavaScript required) .

↑ ^a ^b David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-416.

↑ Entry on Pentan-3-one in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 96-22-0 or 3-pentanone ), accessed on November 2, 2015.

↑ US Patent 3829499, "Production of diethyl ketone", August 13, 1974, Shell Oil Corp. .

↑ US Patent 4754074, "Preparation of dialkyl ketones from aliphatic carboxylic acids" of June 28, 1988, Amoco Corp. .

↑ 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 .

↑ Committee on Updating of Occupational Exposure Limits: Datasheet Pentan-3-one ( page no longer available , search in web archives ) Info: The link was automatically marked as defective. Please check the link according to the instructions and then remove this notice. , (English, PDF file; 128 kB), accessed on March 30, 2013.@1@ 2Template: Dead Link / www.gr.nl

[CosIng-1] Entry on DIETHYLKETONE in the CosIng database of the EU Commission, accessed on March 21, 2020.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o Entry on 3-pentanone in the GESTIS substance database of the IFA , accessed on April 10, 2018(JavaScript required) .

[CRC90_3_416-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-416.

[CLP_100.002.265-4] Entry on Pentan-3-one in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[5] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 96-22-0 or 3-pentanone ), accessed on November 2, 2015.

[6] US Patent 3829499, "Production of diethyl ketone", August 13, 1974, Shell Oil Corp. .

[7] US Patent 4754074, "Preparation of dialkyl ketones from aliphatic carboxylic acids" of June 28, 1988, Amoco Corp. .

[8] 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-9] 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 .