2-butanone oxime

Structural formula
( E ) shape (left) and ( Z ) shape (right)
General
Surname	2-butanone oxime
other names	Methyl ethyl ketone oxime Methyl ethyl ketoxime Butane oxime MEKO ( E ) -butanone oxime ( Z ) -butanone oxime ( EZ ) -butanone oxime
Molecular formula	C 4 H 9 N-O
Brief description	colorless liquid with an aromatic odor
External identifiers / databases
CAS number 96-29-7 [( E, Z ) -isomer mixture] 10341-63-6 [( E ) -isomer] 10341-59-0 [( Z ) -isomer] EC number 202-496-6 ECHA InfoCard 100.002.270 PubChem 5324275 Wikidata Q5230000
properties
Molar mass	87.12 g · mol -1
Physical state	liquid
density	0.92 g cm −3
Melting point	−29.5 ° C
boiling point	152 ° C
Vapor pressure	5.91 h Pa (40 ° C)
solubility	moderate in water (114 g l −1 at 20 ° C)
Refractive index	1.441-1.444
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 226-312-317-318-351 P: 280-305 + 351 + 338
Toxicological data	2528 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

2-Butanone oxime is a chemical compound from the group of oximes . It is a colorless, volatile liquid with an aromatic odor.

Extraction and presentation

2-butanone oxime can be obtained by catalytic ammoxidation of 2-butanone .

use

2-Butanone oxime is added to lacquers and wood preservative glazes based on so-called oxidatively drying binders in low concentrations (<1%) as anti-skinning agents, which evaporate relatively quickly after the lacquer has been applied. It is also used in polyurethane processing , as a corrosion protection agent and as an intermediate for the production of derived compounds.

proof

After the sample has been properly prepared, the 2-butanone oxime content can be measured by gas chromatography with a nitrogen-selective detector. For thermally unstable substances, e.g. B. prepolymers, analysis using liquid chromatography and quantification using a mass-selective detector (HPLC / MS) is recommended. The sample matrix is ​​separated by chromatography on a reversed phase column and the mass of the butanone oxime is detected. The advantage of HPLC / MS is that no over-results are generated by cleavage and that the detection sensitivity is significantly lower.

safety instructions

The vapors of 2-butanone oxime can form an explosive mixture with air when heated above its flash point of 58 ° C. It should also be noted that the compound has been shown to be carcinogenic in animal experiments ( liver carcinomas are more likely to develop in mice and rats after a lifetime of inhalation ) and that it causes allergies on skin contact.

In Germany, an occupational exposure limit of 1 mg / m ^{3 was} set for 2-butanone oxime in July 2013 .

In 2013, 2-butanone oxime was included in the EU's ongoing action plan ( CoRAP ) in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation . The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. The reasons for the uptake of 2-butanone oxime were concerns about its classification as a CMR substance, consumer use , cumulative exposure , high risk characterization ratio (RCR) and widespread use, as well as the suspected dangers of sensitizing properties. The reassessment took place from 2013 and was carried out by Germany . A final report was then published.

Individual evidence

1. ↑ ^{a b c d e f g h} Entry on 2-butanone oxime in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
2. ↑ Entry on 2-butanone oxime at ChemBlink , accessed on February 25, 2011.
3. ↑ Entry on Butanone oxime 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. ↑ Safety data sheet with information on the individual components (PDF; 45 kB).
5. ↑ Study on Catalyst and Solvent in Preparation of 2-Butanone Oxime by Catalytic Ammoxidation .
6. ↑ ^{a b} Rainer Dörr, Thorsten Reinecke, Klaus Kersting, Reinhold Rühl: 2-butanone oxime (MEKO) in paints, parquet seals and silicone sealants. In: Hazardous substances - cleanliness. Air . 77, No. 3, 2017, pp. 63–68.
7. ↑ PE Newton, HF Bolte, MJ Derelanko, JF Hardisty, WE Rinehart: An evaluation of changes and recovery in the olfactory epithelium in mice after inhalation exposure to methylethylketoxime . In: Inhalation Toxicology . tape 14 , no. 12 , 2002, p. 1249-1260 , doi : 10.1080 / 08958370290084890 .
8. ↑ ^{a b} Measurement method for butanone oxime ( Memento from July 18, 2011 in the Internet Archive ).
9. ↑ Main association of commercial trade associations: Procedure for the determination of 2-butanone oxime , 4/2001.
10. ^ Trade Association of the Construction Industry: Sealing Compounds ( Memento from March 1, 2012 in the Internet Archive ).
11. ^ European Chemicals Agency (ECHA): Substance Evaluation Report and Conclusion Document .
12. ↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): Butanone oxime , accessed on March 26, 2019.