Vinyl acetate

Structural formula
General
Surname	Vinyl acetate
other names	Ethenyl acetate ( IUPAC ) Vinyl acetate Ethenyl ethanoate Ethenyl acetate 1-acetoxyethylene VAM
Molecular formula	C 4 H 6 O 2
Brief description	colorless, light-sensitive, highly flammable liquid with a sweet odor
External identifiers / databases
CAS number 108-05-4 EC number 203-545-4 ECHA InfoCard 100.003.224 PubChem 7904 Wikidata Q377339
properties
Molar mass	86.09 g mol −1
Physical state	liquid
density	0.93 g cm −3
Melting point	−100 ° C
boiling point	72 ° C
Vapor pressure	120 h Pa (20 ° C) 192 hPa (30 ° C) 297 hPa (40 ° C) 445 hPa (50 ° C)
solubility	poor in water (20 g l −1 at 20 ° C) readily soluble in common solvents, e.g. B. ethyl acetate and ethanol
Refractive index	1.3956
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 225-332-335-351-412 P: 210-261-273-304 + 340 + 312-403 + 235
MAK	DFG : no information, as carcinogenic Switzerland: 10 ml m −3 or 35 mg m −3
Toxicological data	2920 mg kg −1 ( LD 50 ,  rat ,  oral )
Thermodynamic properties
ΔH f 0	−349.2 kJ mol −1
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

Vinyl acetate (according to IUPAC nomenclature: ethenyl acetate , systematically also referred to as ethenyl ethanoate ) is an organic-chemical compound from the group of carboxylic acid esters . It is in the form of a colorless liquid with a sweetish odor. Vinyl acetate is photosensitive and then tends to polymerize spontaneously .

history

The monomeric vinyl acetate was first presented in 1912 by Fritz Klatte at Griesheim-Elektron .

Extraction and presentation

The large-scale synthesis of vinyl acetate takes place through the selective gas phase oxidation of acetic acid with ethene in the presence of oxygen . The reaction takes place in steam-heated tube bundle reactors at temperatures of 150–160 ° C. and pressures of 8–11 bar. Bimetallic palladium- gold shell catalysts are used as catalysts .

The selectivity for vinyl acetate is 92%, the space-time yield is around 900 g / l per hour.

The annual demand for vinyl acetate in the United States is approximately 1.14 million tons (as of 2005).

properties

Physical Properties

Vinyl acetate has a viscosity of 0.43 mPa · s at 20 ° C, a specific heat capacity of 1.926 kJ / (kg · K) at 20 ° C, a heat of vaporization of 379.3 kJ / kg, a heat of polymerization of 1035.8 kJ / kg (at 76.8 ° C), a heat of combustion 2082.9 kJ / mol at 25 ° C. Vinyl acetate vapors are three times as heavy as air. With water, vinyl acetate forms an azeotrope which boils at 66 ° C. under normal pressure and contains 92.7% vinyl acetate.

Chemical properties

Vinyl acetate polymerizes very easily under the influence of various activators, e.g. B. light or peroxides , as well as thermally when heated. The heat of polymerization is −88 kJ · mol ⁻¹ or –1020 kJ · kg ⁻¹ . A number of addition and transesterification reactions are possible as an unsaturated ester .

Safety-related parameters

Vinyl acetate forms highly flammable vapor-air mixtures. The compound has a flash point of −8 ° C. The explosion range is between 2.6% by volume (93 g / m³) as the lower explosion limit (LEL) and 13.4% by volume (480 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 0.93 mm. This results in an assignment to explosion group IIA. The ignition temperature is 385 ° C. The substance therefore falls into temperature class T2.

use

Vinyl acetate is a monomer and is mainly used in the production of polyvinyl acetate and, to a lesser extent, vinyl acetate copolymers (such as ethylene-vinyl acetates or ethylene-vinyl alcohol copolymers ) and polyvinyl alcohol . These polymers are used in the form of liquid dispersions , dispersion powders, solid resins and solutions, in particular as binders in the construction, paint and lacquer sectors and as raw materials for the adhesive, paper and textile industries.

Safety instructions / risk assessment

Vinyl acetate is classified as carcinogenic in accordance with EC Category 3 (substances that give cause for concern because of their possible carcinogenic effects in humans). Vinyl acetate can easily form explosive peroxides in air, which can be suppressed by adding stabilizers (e.g. hydroquinone or methylhydroquinone in a concentration of 3 to 20 ppm).

In 2016, vinyl acetate 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 vinyl acetate were concerns about consumer use , high (aggregated) tonnage and widespread use as well as the possible dangers of reproductive toxicity and sensitizing properties and as a potential endocrine disruptor . The re-evaluation has been running since 2019 and is carried out by Latvia .

Web links

Commons : Vinyl Acetate  - Collection of images, videos, and audio files

• Vinyl Acetate Council: Guide to the Safe Use of Vinyl Acetate , April 2010 (pdf)

Individual evidence

1. ↑ ^{a b c d e f g h i j k l m n o p q} Entry on vinyl acetate in the GESTIS substance database of the IFA , accessed on June 20, 2018(JavaScript required) .
2. ↑ ^{a b c d} data sheet from Celanese Chemicals .
3. ↑ Entry on vinyl acetate 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 108-05-4 or vinyl acetate ), accessed on September 30, 2019.
5. ↑ ^{a b} Guide to the Safe Handling of Vinyl Acetate. (PDF; 956 kB) Vinyl Acetate Council, April 2010, p. 7 , accessed on December 29, 2017 (English). 
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. 5-25.
7. ↑ Data sheet from Kremer Pigments ( Memento of the original from February 10, 2008 in the Internet Archive ) Info: The archive link was automatically inserted and not yet checked. Please check the original and archive link according to the instructions and then remove this notice. 
8. ↑ ^{a b} Entry on vinyl acetate. In: Römpp Online . Georg Thieme Verlag, accessed on February 26, 2019 .
9. ↑ Trade Association Raw Materials and Chemical Industry , Leaflet R 008 Polyreactions and Polymerizable Systems , Edition 05/2015, ISBN 978-3-86825-069-5 .
10. ^ ^{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.
11. ^ MD Lechner, K. Gehrke and EH Nordmeier: Makromolekulare Chemie , 4th edition, Birkhäuser Verlag, 2010, ISBN 978-3-7643-8890-4 , p. 53, p. 58 and P. 63.
12. ↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): Vinyl acetate , accessed on March 26, 2019.