Methyl isobutyl ketone

Structural formula
General
Surname	Methyl isobutyl ketone
other names	MIBK; Isobutyl methyl ketone; 4-methyl-2-pentanone; Methyl (beta-methylpropyl) ketone; Methyl isobutyl ketone; Isopropyl acetone; Hexon; 4-methylpentan-2-one ( IUPAC );
Molecular formula	C 6 H 12 O
Brief description	colorless liquid with a pleasant odor
External identifiers / databases
EC number	203-550-1
ECHA InfoCard	100.003.228
PubChem	7909
Wikidata	Q418104
properties
Molar mass	100.16 g mol −1
Physical state	liquid
density	0.80 g cm −3
Melting point	−80 ° C
boiling point	116 ° C
Vapor pressure	18.8 h Pa (20 ° C); 33.3 hPa (30 ° C); 56.2 hPa (40 ° C); 90.9 hPa (50 ° C);
solubility	poor in water (19 g l −1 at 20 ° C)
Refractive index	1.395 (20 ° C)
safety instructions
H and P phrases	H: 225-332-335-319
	EUH: 066
	P: 210-305 + 351 + 338-304 + 340
MAK	DFG : 20 ml m −3 or 83 mg m −3 ; Switzerland: 20 ml m −3 or 82 mg m −3 ;
	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

Methyl isobutyl ketone ( MIBK ) is a chemical compound from the group of ketones . It is made from acetone , serves as a solvent , extractant and is an intermediate for synthesis .

Manufacturing

MIBK is produced industrially in a one-pot reaction from acetone and hydrogen in the presence of a transition metal catalyst. The acetone first undergoes an aldol condensation with itself, the diacetone alcohol formed eliminates water and is then hydrogenated . Alternatively, a step-by-step production starting from acetone via the intermediate products diacetone alcohol and mesityl oxide is also possible.

properties

Methyl isobutyl ketone is a volatile, highly flammable, colorless liquid with a pleasant ketone-like odor and low water solubility.

Safety-related parameters

Methyl isobutyl ketone forms highly flammable vapor-air mixtures. The compound has a flash point of 14 ° C. The explosion range is between 1.2% by volume (50 g / m³) as the lower explosion limit (LEL) and 8% by volume (330 g / m³) as the upper explosion limit (UEL). According to the vapor pressure function, there is a lower explosion point of 10 ° C. The limit gap width was determined to be 0.98 mm. This results in an assignment to explosion group IIA. The ignition temperature is 475 ° C. The substance therefore falls into temperature class T1.

use

MIBK is used as a polar solvent , especially for paints, synthetic resins, in electronics and when using CS tear gas . It is also useful as an extraction agent in the analysis and extraction of rare metals. Large quantities are produced as an intermediate product in the synthesis of 6PPD , a rubber and wax plasticizer, and in other syntheses.

safety instructions

The IARC classified MIBK as possibly carcinogenic in 2013. According to the announcement of the list of substances hazardous to water in the Federal Gazette of August 10, 2017 (last amended on August 10, 2018), the substance with the WGK 1 classification is only slightly hazardous to water.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r Entry on 4-methyl-2-pentanone in the GESTIS substance database of the IFA , accessed on September 24, 2018(JavaScript required) .
↑ Data sheet 4-Methyl-2-pentanone from Sigma-Aldrich , accessed on April 10, 2011 ( PDF ).
↑ Entry on 4-methylpentan-2-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 108-10-1 or methyl isobutyl ketone ), accessed on November 2, 2015.
↑ US Patent 4,289,911 .
^ ^A ^b ^c ^d E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.
↑ IARC Monograph 101 - Methyl Isobutyl Ketone, 2013

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r Entry on 4-methyl-2-pentanone in the GESTIS substance database of the IFA , accessed on September 24, 2018(JavaScript required) .

[Sigma-2] Data sheet 4-Methyl-2-pentanone from Sigma-Aldrich , accessed on April 10, 2011 ( PDF ).

[CLP_100.003.228-3] Entry on 4-methylpentan-2-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 .

[4] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 108-10-1 or methyl isobutyl ketone ), accessed on November 2, 2015.

[5] US Patent 4,289,911 .

[Brandes-6] A ^b ^c ^d E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.

[7] IARC Monograph 101 - Methyl Isobutyl Ketone, 2013