Acetophenone

Structural formula
General
Surname	Acetophenone
other names	1-phenylethanone ( IUPAC ) ; Methyl phenyl ketone; Phenyl methyl ketone; Hypnon; Acetylbenzene; Dymex; ACETOPHENONE ( INCI ) ;
Molecular formula	C 8 H 8 O
Brief description	colorless to slightly yellowish, oily liquid with a sweet odor
External identifiers / databases
EC number	202-708-7
ECHA InfoCard	100.002.462
PubChem	7410
ChemSpider	7132
DrugBank	DB04619
Wikidata	Q375112
properties
Molar mass	120.15 g mol −1
Physical state	Liquid above 20 ° C, solid below
density	1.03 g cm −3
Melting point	20 ° C
boiling point	202 ° C
Vapor pressure	0.4 h Pa (20 ° C); 0.8 hPa (30 ° C); 2.9 hPa (50 ° C);
solubility	Slightly soluble in water (6.9 g l −1 at 25 ° C) * in ethanol , diethyl ether , benzene and chloroform ;
Refractive index	1.5372 (20 ° C)
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
H and P phrases	H: 302-319
	P: 305 + 351 + 338
Toxicological data	815 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

Acetophenon [ at͡setofeˈnoːn ] (name composed of: Acet yl-, o , phen from the phenyl group and on to denote as ketone) is an aromatic organic - chemical compound and belongs to the ketones . Acetophenone is used, among other things, as a hypnotic and is known as such under the common name Hypnon .

Occurrence

Acetophenone is also a component of many essential oils such as Labdanum , Castoreum and Stirlingia latifolia . This ketone is also found in many natural flavors and in coal tar .

Extraction and presentation

Acetophenone can be produced by Friedel-Crafts acylation of benzene with acetic acid chloride or acetic anhydride . In contrast to Friedel-Crafts alkylation , the Lewis acid aluminum chloride (AlCl ₃ ) does not act as a catalyst , but is consumed as a reagent in equivalent amounts, with aluminum hydroxide being formed after the necessary hydrolysis of the intermediate product .

properties

Physical Properties

Acetophenone is a colorless to yellowish liquid with a sweet smell reminiscent of orange blossom. The compound boils at 202 ° 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 = 4.64896, B = 2006.397 and C = −43.472 in the temperature range from 310 to 475 K. Acetophenone forms an azeotropic mixture with water at 98 ° C and 82% water.

Compilation of the most important thermodynamic properties
property	Type	Value [unit]	Remarks
Standard enthalpy of formation	Δ _f H ⁰_liquid Δ _f H ⁰_gas	−142.5 kJ mol ⁻¹ −86.7 kJ mol ⁻¹
Standard entropy	S ⁰_gas	372.88 J mol ⁻¹ K ⁻¹	than gas
Enthalpy of combustion	Δ _c H ⁰_liquid	−4148.9 kJ mol ⁻¹
Heat capacity	c _p	227.6 J mol ⁻¹ K ⁻¹ (25 ° C)	as a liquid
Critical temperature	T _c	709.6 K
Critical pressure	p _c	40.1 bar
Critical density	ρ _c	2.59 mol·l ⁻¹
Enthalpy of fusion	Δ _f H	16.65 kJ mol ⁻¹	at the melting point
Enthalpy of evaporation	Δ _V H	43.63 kJ mol ⁻¹	at normal pressure boiling point

Safety-related parameters

Acetophenone forms flammable vapor-air mixtures at higher temperatures. The compound has a flash point of 77 ° C. The lower explosion limit is 1.1 vol.% (55 g / m ³ ), the lower explosion point at 70 ° C. The ignition temperature is 535 ° C. The substance therefore falls into temperature class T1. The electrical conductivity is rather low at 3.1 · 10 ⁻⁷ S · m ⁻¹ .

use

Due to its reactive structure, acetophenone is the starting material of numerous syntheses as a starting or intermediate product for other fragrances and pharmaceuticals as well as synthetic resins. It can also be used as a high-boiling solvent for paints and resins.

safety instructions

Acetophenone as a pure substance is harmful if swallowed. It is irritating to the eyes and can cause dermatitis if exposed to unprotected skin . Suitable gloves should be worn as splash protection. In higher concentrations it has a hypnotic effect, hence the synonym hypnon. At a concentration of 80 ppm, the vapors produce severe symptoms of poisoning after exposure for over an hour . Acetophenone is difficult to ignite and not very volatile. The vapors are much heavier than air. Strongly exothermic reactions can occur with strong oxidizing agents and strong bases. Above 300 ° C, acetophenone decomposes. Here can benzene , biphenyl , 1,4-diphenylbenzene , carbon monoxide , methane , hydrogen , ethene and / or toluene arise.

Derivatives

Starting from acetophenone, there are some derivatives with additional hydroxyl and methoxy groups as substituents:

Individual evidence

↑ Entry on ACETOPHENONE in the CosIng database of the EU Commission, accessed on May 4, 2020.
↑ ^a ^b ^c ^d ^e Entry on acetophenone. In: Römpp Online . Georg Thieme Verlag, accessed on March 3, 2014.
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m Entry on acetophenone in the GESTIS substance database of the IFA , accessed on July 28, 2017(JavaScript required) .
↑ 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. 3-6.
↑ Entry on Acetophenone 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 .
↑ Stull, DR: Vapor Pressure of Pure Substances Organic Compounds in Ind. Eng. Chem. 39 (1947) 517-540, doi : 10.1021 / ie50448a022 .
^ IM Smallwood: Handbook of organic solvent properties , Arnold London 1996, ISBN 0-340-64578-4 , pp. 183-185.
↑ ^a ^b ^c Colomina, M .; Latorre, C .; Perez-Ossorio, R .: Heats of combustion of five alkyl phenyl ketones in Pure Appl. Chem. 2 (1961) 133-135.
^ Stull DR, Jr .: The Chemical Thermodynamics of Organic Compounds , Wiley, New York, 1969.
↑ Phillip, NM: Adiabatic and isothermal compressibilities of liquids in Proc. Indian Acad. Sci., 1939, A9, 109-120.
↑ ^a ^b Teja, AS; Rosenthal, DJ: The critical pressures and temperatures of ten substances using a low residence time flow apparatus in Experimental Results for Phase Equilibria and Pure Component Properties in DIPPR DATA Series No. 1, 1991.
↑ Teja, AS; Anselme, MJ: The critical properties of thermally stable and unstable fluids. I. 1985 results in AIChE Symp. Ser., 1990, 86, 279, 115-121.
↑ Luginin: Bull. Soc. Chim. Fr. 9 (1911) 223.
^ Steele, WV; Chirico, RD; Knipmeyer, SE; Nguyen, A .: in J. Chem. Eng. Data 41 (1996) 1255-1268, doi : 10.1021 / je9601117 .
^ ^A ^b ^c E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.
↑ Technical rule for hazardous substances TRGS 727, BG RCI leaflet T033 Avoidance of ignition hazards due to electrostatic charges , status August 2016, Jedermann-Verlag Heidelberg, ISBN 978-3-86825-103-6 .

[CosIng-1] Entry on ACETOPHENONE in the CosIng database of the EU Commission, accessed on May 4, 2020.

[roempp-2] Entry on acetophenone. In: Römpp Online . Georg Thieme Verlag, accessed on March 3, 2014.

[GESTIS-3] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m Entry on acetophenone in the GESTIS substance database of the IFA , accessed on July 28, 2017(JavaScript required) .

[CRC90_3_6-4] 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. 3-6.

[CLP_100.002.462-5] Entry on Acetophenone 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 .

[Stull1-6] Stull, DR: Vapor Pressure of Pure Substances Organic Compounds in Ind. Eng. Chem. 39 (1947) 517-540, doi : 10.1021 / ie50448a022 .

[Smallwood-7] IM Smallwood: Handbook of organic solvent properties , Arnold London 1996, ISBN 0-340-64578-4 , pp. 183-185.

[Colomina-8] Colomina, M .; Latorre, C .; Perez-Ossorio, R .: Heats of combustion of five alkyl phenyl ketones in Pure Appl. Chem. 2 (1961) 133-135.

[Stull-9] Stull DR, Jr .: The Chemical Thermodynamics of Organic Compounds , Wiley, New York, 1969.

[10] Phillip, NM: Adiabatic and isothermal compressibilities of liquids in Proc. Indian Acad. Sci., 1939, A9, 109-120.

[Teja-11] Teja, AS; Rosenthal, DJ: The critical pressures and temperatures of ten substances using a low residence time flow apparatus in Experimental Results for Phase Equilibria and Pure Component Properties in DIPPR DATA Series No. 1, 1991.

[Teja2-12] Teja, AS; Anselme, MJ: The critical properties of thermally stable and unstable fluids. I. 1985 results in AIChE Symp. Ser., 1990, 86, 279, 115-121.

[13] Luginin: Bull. Soc. Chim. Fr. 9 (1911) 223.

[Steele-14] Steele, WV; Chirico, RD; Knipmeyer, SE; Nguyen, A .: in J. Chem. Eng. Data 41 (1996) 1255-1268, doi : 10.1021 / je9601117 .

[Brandes-15] A ^b ^c E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.

[16] Technical rule for hazardous substances TRGS 727, BG RCI leaflet T033 Avoidance of ignition hazards due to electrostatic charges , status August 2016, Jedermann-Verlag Heidelberg, ISBN 978-3-86825-103-6 .