Cyclopentanone

Structural formula
General
Surname	Cyclopentanone
other names	Ketopentamethylene; Adipinketone;
Molecular formula	C 5 H 8 O
Brief description	colorless liquid with a faint peppermint odor
External identifiers / databases
EC number	204-435-9
ECHA InfoCard	100.004.033
PubChem	8452
ChemSpider	8141
Wikidata	Q416065
properties
Molar mass	84.12 g mol −1
Physical state	liquid
density	0.95 g cm −3 (20 ° C)
Melting point	−58.2 ° C
boiling point	131 ° C
Vapor pressure	11.4 h Pa (20 ° C); 20.5 hPa (30 ° C); 35.2 hPa (40 ° C); 57.8 hPa (50 ° C);
solubility	poor in water (9.18 g l −1 at 25 ° C); soluble in many organic solvents;
Refractive index	1.4366 (20 ° C)
safety instructions
H and P phrases	H: 226-315-319
	P: 210-302 + 352-305 + 351 + 338
Thermodynamic properties
ΔH f 0	−235.9 kJ / mol (l) ; −192.1 kJ / mol (g)
	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

Cyclopentanone is a cyclic ketone ( cycloalkanone ) derived from cyclopentane . The compound can be found as a building block in natural compounds, such as thujones and some prostaglandins , but also in synthetic pharmaceutical products such as alprostadil and misoprostol .

Manufacturing

Cyclopentanone can be produced synthetically by heating salts of adipic acid . Other synthetic routes are the catalytic oxidation of cyclopentene with oxygen and the oxidation of cyclopentane.

properties

The miscibility with water is limited. As the temperature rises, the solubility of cyclopentanone in water decreases or the solubility of water in cyclopentanone increases.

Solubilities between cyclopentanone and water
temperature	° C	0	10.0	20.1	30.0	40.2	50.0	60.6	70.5	80.0	90.7
Cyclopentanone in water	% (m / m)	37.7	34.4	31.0	27.9	25.7	24.4	23.6	23.7	24.8	26.1
Water in cyclopentanone	% (m / m)	13.0	13.8	14.4	15.0	15.7	16.9	18.3	20.3	22.4	26.5

Cyclopentanone forms highly flammable vapor-air mixtures. The compound has a flash point of 26 ° C. The explosion range is between 1.6% by volume as the lower explosion limit (LEL) and 10.8% by volume as the upper explosion limit (UEL). The ignition temperature is 445 ° C. The substance therefore falls into temperature class T2.

use

In microelectronics , cyclopentanone is used as a solvent for photoresists and polyimides .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Entry on cyclopentanone in the GESTIS substance database of the IFA , accessed on October 14, 2019(JavaScript required) .

↑ ^a ^b entry on cyclopentanone. In: Römpp Online . Georg Thieme Verlag, accessed on November 12, 2014.

↑ 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. 3-130.

↑ Entry on Cyclopentanone 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 .

↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 95th edition. (Internet version: 2015), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-28. See also entry on cyclopentanone . In: P. J. Linstrom, W. G. Mallard (Eds.): NIST Chemistry WebBook, NIST Standard Reference Database Number 69 . National Institute of Standards and Technology , Gaithersburg MD, accessed on 22 March 2010 .

↑ J. Smidt, W. Hafner, R. Jira, J. Sedlmeier, R. Sieber, R. Rüttinger, H. Kojer: Catalytic reactions of olefins on platinum metal compounds The Consortium process for the production of acetaldehyde , in: Angew. Chem. 1959 , 71 , 176-182; doi: 10.1002 / anie.19590710503 .

↑ Patent US2391740 : Sensitization of hydrogen bromide catalyzed oxidation reactions. Applied January 17, 1944 , published December 25, 1945 , Applicant: Shell Devel. Co., Inventors: John H. Raley, Frederick F. Rust. ‌

^ ^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 .

↑ E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.

↑ Marc J. Madou: Manufacturing Techniques for Microfabrication and Nanotechnology. CRC Press, 2011, ISBN 978-1-439-89530-6 , p. 34 ( limited preview in Google book search).

↑ Joachim Bargon: Methods and Materials in Microelectronic Technology. Springer Science & Business Media, 2013, ISBN 978-1-468-44847-4 , p. 204 ( limited preview in Google book search).

[gestis-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Entry on cyclopentanone in the GESTIS substance database of the IFA , accessed on October 14, 2019(JavaScript required) .

[roempp-2] try on cyclopentanone. In: Römpp Online . Georg Thieme Verlag, accessed on November 12, 2014.

[CRC90_3_130-3] 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. 3-130.

[CLP_100.004.033-4] Entry on Cyclopentanone 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 .