3-butene-2-one

Structural formula
General
Surname	3-butene-2-one
other names	Butenone; 1-butene-3-one; But-3-en-2-one ( IUPAC ); Vinyl methyl ketone;
Molecular formula	C 4 H 6 O
Brief description	light-sensitive, volatile, colorless liquid with an unpleasant odor
External identifiers / databases
EC number	201-160-6
ECHA InfoCard	100.001.055
PubChem	6570
ChemSpider	6322
Wikidata	Q417525
properties
Molar mass	70.09 g · mol -1
Physical state	liquid
density	0.83 g cm −3
Melting point	−7 ° C
boiling point	81.4 ° C
Vapor pressure	100 h Pa (20 ° C)
solubility	miscible with water
Refractive index	1.4081 (20 ° C)
safety instructions
H and P phrases	H: 225-300 + 310 + 330-314-317-410
	P: 210-260-264-273-280-284
Toxicological data	23.1 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-buten-2-one (also methyl vinyl ketone ) is the simplest unsaturated ketone , a pungent-smelling liquid that polymerizes easily .

Extraction and presentation

The compound can be made by hydrating vinyl acetylene ( butenine ) in the presence of sulfuric acid and mercury (II) sulfate :

properties

3-buten-2-one is a colorless, light-sensitive liquid that boils at 81 ° C under normal pressure . The compound is completely miscible with water below 28 ° C. Above this temperature, in the range exists between about 10 and 40 mole percent of a miscibility gap .

use

3-buten-2-one is used in the manufacture of gas-impermeable plastics and as an intermediate in the manufacture of pharmaceuticals , fungicides and other chemical compounds (e.g. 2-ethoxy-buta-1,3-diene or 1-phenyl-pentane-1 , 4-dione ) is used. It is implemented, for example, by a Diels-Alder reaction or Robinson annulation .

safety instructions

3-buten-2-one tends to form explosive peroxides and to spontaneous polymerization, which can be triggered by sunlight. The vapors of 3-butene-2-one form explosive mixtures with air. The compound has a flash point of −7 ° C. The explosion range is between 2.1 vol.% As the lower explosion limit (LEL) and 15.6 vol.% As the upper explosion limit (UEL). The ignition temperature is 491 ° C. The substance therefore falls into temperature class T1.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on butenone in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ ^a ^b H. Beyer u. W. Walter: Textbook of Organic Chemistry . 20th ed., Hirzel, Stuttgart, 1984. p. 211.
↑ 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. 3-74.
↑ Dortmund database .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on butenone in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[BW-2] H. Beyer u. W. Walter: Textbook of Organic Chemistry . 20th ed., Hirzel, Stuttgart, 1984. p. 211.

[CRC90_3_74-3] 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. 3-74.

[4] Dortmund database .