Acrylonitrile

Structural formula
General
Surname	Acrylonitrile
other names	Prop-2-enenitrile ( IUPAC ) 2-propenenitrile Acrylonitrile ACN Vinyl cyanide Ventox
Molecular formula	C 3 H 3 N
Brief description	colorless liquid with a pungent odor
External identifiers / databases
CAS number 107-13-1 EC number 203-466-5 ECHA InfoCard 100.003.152 PubChem 7855 ChemSpider 7567 Wikidata Q342968
properties
Molar mass	53.06 g mol −1
Physical state	liquid
density	0.8 g cm −3 (20 ° C)
Melting point	−82 ° C
boiling point	77 ° C
Vapor pressure	117 h Pa (20 ° C)
solubility	moderate in water (73 g l −1 at 20 ° C)
Refractive index	1.3911 (20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 225-350-331-311-301-361-335-315-318-317-411 P: 201-210-280-301 + 310 + 330-305 + 351 + 338-308 + 313-403 + 233
MAK	Switzerland: 2 ml m −3 or 4.5 mg m −3
Toxicological data	78 mg kg −1 ( LD 50 ,  rat ,  oral )
Thermodynamic properties
ΔH f 0	147.1 kJ / mol
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

Acrylonitrile ( IUPAC prop-2-enenitrile ) is the nitrile of acrylic acid . It is the simplest unsaturated nitrile.

Technical manufacturing

Acrylonitrile is produced using the Sohio process , a catalytically controlled conversion of propene with ammonia and pure oxygen . The reaction is also known as ammoxidation of propene. This produces acrylonitrile with elimination of water with acetonitrile and hydrocyanic acid as by-products . The catalyst is a mixture of iron , bismuth and molybdenum .

use

Acrylonitrile is used as a raw material for the production of acrylic acid , acrylic esters and acrylamide . It is also a component for adhesives , antioxidants , emulsifiers and solvents . The most important use of acrylonitrile is the polymerization to polyacrylonitrile and other copolymers ( acrylonitrile-butadiene-styrene (ABS) , styrene-acrylonitrile (SAN) , acrylonitrile-butadiene-rubber (NBR) and acrylic ester-styrene-acrylonitrile (ASA) ). In organic syntheses it is used for cyanoethylation .

Emission measurement

The emission measurement of exhaust gas loaded with acrylonitrile is usually carried out by gas chromatography . Sampling can be carried out using a gas collection vessel or absorption in cryogenic solvents. The draft of a VDI guideline , which describes the measurement of acrylonitrile by adsorption on activated carbon and desorption by dimethylformamide , was withdrawn in 2004.

Individual evidence

1. ↑ ^{a b} Entry on acrylonitrile. In: Römpp Online . Georg Thieme Verlag, accessed on May 29, 2014.
2. ↑ ^{a b c d e f g} Entry on acrylonitrile in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
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. 3-8.
4. ↑ Entry on acrylonitrile 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 107-13-1 or acrylonitrile ), accessed on November 2, 2015.
6. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-23.
7. ^ History of the development of the process ( memento of October 12, 2006 in the Internet Archive ) at Sohio .
8. ↑ VDI 3863 sheet 1: 1987-04 measurement of gaseous emissions; Measuring acrylonitrile; Gas chromatographic method; Sampling with gas collection vessels (measurement of gaseous emission; determination of acrylonitrile; gaschromatographic method; grab sampling). Beuth Verlag, Berlin, p. 2.
9. ↑ VDI 3863 sheet 2: 1991-02 measurement of gaseous emissions; Measuring acrylonitrile; Gas chromatographic process; Sampling by absorption in low temperature solvents (Gaseous emission measurement; determination of acrylonitrile; gas chromatographic method; sampling by absorption in low temperature solvents). Beuth Verlag, Berlin, p. 2.
10. ^ Association of German Engineers : VDI guideline: VDI 3863 Part 3 Measurement of gaseous emissions; Measuring acrylonitrile; Adsorption on activated carbon; Desorption by dimethylformamide (DMF) , accessed July 13, 2017