4-methyl-3-penten-2-one

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Structural formula
Structural formula of mesityl oxide
General
Surname 4-methyl-3-penten-2-one
other names
  • Mesity oxide
  • Isopropylidene acetone
  • 1-isobutenyl methyl ketone
  • Methyl isobutenyl ketone
  • 4-METHYLPENT-3-EN-2-ONE ( INCI )
Molecular formula C 6 H 10 O
Brief description

colorless to yellowish, aromatic, flammable liquid

External identifiers / databases
CAS number 141-79-7
EC number 205-502-5
ECHA InfoCard 100.005.002
PubChem 8858
ChemSpider 8526
Wikidata Q425668
properties
Molar mass 98.14 g mol −1
Physical state

liquid

density

0.85 g cm −3

Melting point

−59 ° C

boiling point

130 ° C

Vapor pressure

10.9 h Pa (20 ° C)

solubility

poor in water (30 g l −1 at 20 ° C)

Refractive index

1.44397

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
02 - Highly / extremely flammable 06 - Toxic or very toxic

danger

H and P phrases H: 226-302-331-315-319-335
P: 210-261-280-303 + 361 + 353-311-403 + 233
MAK
  • DFG : 2 ml m −3 , 8.1 mg m −3
  • Switzerland: 5 ml m −3 , 20 mg m −3
  • Austria: 25 ml m −3 , 100 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

4-methyl-3-penten-2-one (also mesityl oxide), a colorless to yellow, oily liquid with a peppermint-like odor , is a condensation product of acetone .

Extraction and presentation

The preparation of 4-methyl-3-penten-2-one is carried out by dehydration of diacetone alcohol , which is produced from acetone.

It is an aldol reaction (aldol addition and aldol condensation). In the laboratory, the representation is often done using a Soxhlet sleeve over calcium hydroxide .

use

Most of the industrially produced 4-methyl-3-penten-2-one is processed into methyl isobutyl ketone .

It also serves as a starting product for the synthesis of terpenes and fragrances , as well as an extractant for thorium and uranium in ore flotation .

Individual evidence

  1. ↑ Entry on 4-METHYLPENT-3-EN-2-ONE in the CosIng database of the EU Commission, accessed on March 18, 2020.
  2. ↑ a b c d e f g h i Entry on 4-methyl-3-penten-2-one in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
  3. ↑ CRC Handbook of Tables for Organic Compound Identification , Third Edition, 1984, ISBN 0-8493-0303-6 .
  4. ↑ Entry on 4-methylpent-3-en-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 .
  5. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 141-79-7 or mesityloxide ), accessed on November 2, 2015.
  6. ↑ Limit values ​​for working materials ( Memento of the original from September 23, 2015 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. , Ordinance of the Federal Minister for Labor, Social Affairs and Consumer Protection (Limit Values ​​Ordinance GKV 2011), Austria. @1@ 2Template: Webachiv / IABot / www.arbeitsinspektion.gv.at
  7. ↑ JB Conant, N. Tuttle: Mesityl oxide In: Organic Syntheses . 1, 1921, p. 53, doi : 10.15227 / orgsyn.001.0053 ; Coll. Vol. 1, 1941, p. 345 ( PDF ).
  8. ↑ Hoffman, J. Am. Chem. Soc. 31 , 1909 , 722.