Butyl acrylate

Structural formula
General
Surname	Butyl acrylate
other names	Butyl acrylate; Butyl propenoate; Butyl 2-propenoate; n -butyl acrylate;
Molecular formula	C 7 H 12 O 2
Brief description	colorless liquid with a pungent odor
External identifiers / databases
EC number	205-480-7
ECHA InfoCard	100.004.983
PubChem	8846
Wikidata	Q343005
properties
Molar mass	128.17 g mol −1
Physical state	liquid
density	0.90 g cm −3
Melting point	−65 ° C
boiling point	148 ° C
Vapor pressure	5.34 h Pa (20 ° C); 9.71 hPa (30 ° C); 16.9 hPa (40 ° C); 28.2 hPa (50 ° C);
solubility	poor in water (1.6 g l −1 at 20 ° C)
Refractive index	1.4185 (20 ° C)
safety instructions
H and P phrases	H: 226-302 + 312 + 332-315-317-319-335-412
	P: 261-273-280-305 + 351 + 338
MAK	DFG / Switzerland: 2 ml m −3 or 11 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

Acrylic acid butyl ester is a chemical compound from the group of acrylic acid esters and thus also the carboxylic acid ester .

Extraction and presentation

Acrylic acid butyl ester can be obtained by acid-catalyzed esterification of acrylic acid with n-butanol . Another industrial synthesis takes place through the conversion of carbon monoxide with acetylene in the presence of n- butanol.

In 2000, around 250 to 400 thousand tons were produced in Europe and around 500 thousand tons in the USA. This makes it one of the chemical substances that are produced in large quantities (" High Production Volume Chemical ", HPVC) and for which the Organization for Economic Cooperation and Development (OECD) collects data on possible dangers (" Screening Information Dataset ", SIDS).

properties

Acrylic acid butyl ester is a flammable, light-sensitive, colorless liquid with a pungent odor. It can polymerize and is therefore usually supplied with stabilizers . However, the action of heat can render the stabilizer ineffective, which can initiate vigorous polymerization. The heat of polymerization is −78 kJ mol ⁻¹ or −608 kJ kg ⁻¹ .

Safety-related parameters

Acrylic acid butyl ester forms highly flammable vapor-air mixtures. The compound has a flash point of 37 ° C. The explosion range is between 1.2% by volume (63 g / m ³ ) as the lower explosion limit (LEL) and 8% by volume (425 g / m ³ ) as the upper explosion limit (UEL). This results in an upper one Explosion point of 34 ° C. The limit gap width was determined to be 0.88 mm. This results in an assignment to explosion group IIB. The ignition temperature is 275 ° C. The substance therefore falls into temperature class T3.

use

Acrylic acid butyl ester is used as a softening component in acrylic resins and as a reactive diluent in radical radiation curing .

safety instructions

Acrylic acid butyl ester was included in the EU's ongoing action plan ( CoRAP ) in 2013 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 butyl acrylate were concerns about high (aggregated) tonnage and the dangers of a possible assignment to the group of CMR substances. The re-evaluation took place from 2013 and was carried out by Sweden . A final report was then published.

Web links

Commons : Butyl Acrylate - Collection of pictures, videos, and audio files

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q Entry on butyl acrylate in the GESTIS substance database of the IFA , accessed on January 16, 2018(JavaScript required) .
↑ 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. 3-76.
↑ Entry on butyl acrylates 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 141-32-2 or butyl acrylate ), accessed on November 2, 2015.
↑ ^a ^b ^c Entry on butyl acrylate. In: Römpp Online . Georg Thieme Verlag, accessed on January 16, 2018.
↑ Process for the disposal of secondary components from acrylic acid ester or methacrylic acid ester production (WIPO)
↑ Drent, E .; Eberhard, MR; Pringel, PG, WO 2001087899 A1, (2001).
↑ ^a ^b OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for butyl acrylates , accessed on October 3, 2014.
↑ Brandrup, J .; Immergut, EH; Grulke, EA; Abe, A .; Bloch, DR: Polymer Handbook , 4th Edition, Wiley-VCH 2003, ISBN 978-0-471-47936-9 , p. II / 368.
↑ ^a ^b ^c ^d ^e E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.
↑ European Chemicals Agency (ECHA): Substance Evaluation Conclusion and Evaluation Report .
↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): Butyl acrylate , accessed on May 1, 2020.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q Entry on butyl acrylate in the GESTIS substance database of the IFA , accessed on January 16, 2018(JavaScript required) .

[CRC90_3_76-2] 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. 3-76.

[CLP_100.004.983-3] Entry on butyl acrylates 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 141-32-2 or butyl acrylate ), accessed on November 2, 2015.

[Roempp-5] Entry on butyl acrylate. In: Römpp Online . Georg Thieme Verlag, accessed on January 16, 2018.

[6] Process for the disposal of secondary components from acrylic acid ester or methacrylic acid ester production (WIPO)

[7] Drent, E .; Eberhard, MR; Pringel, PG, WO 2001087899 A1, (2001).

[SIDS-8] OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for butyl acrylates , accessed on October 3, 2014.

[Polymer_Handbook-9] Brandrup, J .; Immergut, EH; Grulke, EA; Abe, A .; Bloch, DR: Polymer Handbook , 4th Edition, Wiley-VCH 2003, ISBN 978-0-471-47936-9 , p. II / 368.

[Brandes-10] E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.

[11] European Chemicals Agency (ECHA): Substance Evaluation Conclusion and Evaluation Report .

[12] Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): Butyl acrylate , accessed on May 1, 2020.