2,3-epoxypropyl methacrylate

Structural formula
	Simplified structural formula without stereochemistry
General
Surname	2,3-epoxypropyl methacrylate
other names	Glycidyl methacrylate; (±) -Glycidyl methacrylate; ( RS ) glycidyl methacrylate;
Molecular formula	C 7 H 10 O 3
Brief description	colorless liquid with a sweet odor
External identifiers / databases
EC number	203-441-9
ECHA InfoCard	100.003.130
PubChem	7837
Wikidata	Q2013175
properties
Molar mass	142.15 g mol −1
Physical state	liquid
density	1.04 g cm −3
Melting point	−41.5 ° C
boiling point	189 ° C
Vapor pressure	13.3 mbar (82 ° C)
solubility	little in water (<10 g l −1 at 20 ° C)
Refractive index	1,449 (20 ° C)
safety instructions
H and P phrases	H: 302-311-314-317-335-341-350-360F-372
	P: 201-260-280-305 + 351 + 338-310
Toxicological data	500 mg kg −1 ( LD 50 , rat , oral ) ; 484 mg kg −1 ( LD 50 , rabbit , transdermal ) ; 0.262 mg (l / 4 h) −1 ( LC 50 , rat , inh. ) ;
	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

2,3-Epoxypropyl methacrylate is a chemical compound from the group of substituted carboxylic acid esters and epoxides . It is an ester of methacrylic acid .

Stereoisomerism

2,3-Epoxypropyl methacrylate contains a stereocenter, there are two enantiomeric forms:

( R ) -2,3-epoxypropyl methacrylate and
( S ) -2,3-epoxypropyl methacrylate.

Only ( RS ) -2,3-epoxypropyl methacrylate, i.e. the racemate (1: 1 mixture) of the two enantiomers , is of practical importance . Whenever “2,3-epoxypropyl methacrylate” is mentioned in this article or in the scientific literature without any additional name, it means ( RS ) -2,3-epoxypropyl methacrylate.

Extraction and presentation

2,3-Epoxypropyl methacrylate can be obtained by condensing allyl alcohol and epichlorohydrin with subsequent dehydrochlorination with an alkali to form the epoxy ring.

In 1998 Japan produced about 3,000 t. This makes 2,3-epoxypropyl methacrylate 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).

use

2,3-Epoxypropyl methacrylate is used as a comonomer for polymers . So it is for example for the production of acrylic resin of the powder coating of the Smart used.

safety instructions

2,3-Epoxypropyl methacrylate tends to polymerize spontaneously and there is a risk of explosion if it comes into contact with air. At the suggestion of the Dutch chemicals authority, the chemical classification of 2,3-epoxypropyl methacrylate was revised in 2015. The Committee for Risk Assessment (RAC) of the European Chemicals Agency (ECHA) changed the classification for 2,3-epoxypropyl methacrylate as follows on December 4th: 2,3-epoxypropyl methacrylate is classified as carcinogenic Carc 1B, mutagenic Muta 2, repr 1B and STOT SE3, STOT RE1, Acut Tox 3, Eye Dam 1 and Skin Corr 1C. The warning labels were set to H350, H341, H360F, H311, H335, H372 (respiratory tract, inhalation), H318, H314. This classification of the RAC has yet to be implemented by the EU Commission into applicable law, but with the publication it represents the state of knowledge that must be taken into account by companies and authorities.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on 2,3-epoxypropyl methacrylate in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ ^a ^b Data sheet Glycidyl methacrylate, ≥97.0% (GC) from Sigma-Aldrich , accessed on February 5, 2018 ( PDF ).
↑ Entry on 2,3-epoxypropyl methacrylate 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 .
↑ Entry on 2,3-epoxypropyl methacrylate in the Hazardous Substances Data Bank , accessed on April 18, 2014.
↑ ^a ^b OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for Glycidyl methacrylate , accessed on October 3, 2014.
↑ Gerhard Lagaly, Olivier Schulz, Ralf Zimehl: dispersions and emulsions . Springer, 1997, ISBN 3-642-59248-1 , p. 220 ( limited preview in Google Book search).
^ Judith Pietschmann: Industrial powder coating: Basics, applications, processes . Springer, 2009, ISBN 3-8348-0463-0 , pp. 15 ( limited preview in Google Book search).
↑ RAC decision of December 4, 2015

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on 2,3-epoxypropyl methacrylate in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[Sigma-2] Data sheet Glycidyl methacrylate, ≥97.0% (GC) from Sigma-Aldrich , accessed on February 5, 2018 ( PDF ).

[CLP_100.003.130-3] Entry on 2,3-epoxypropyl methacrylate 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 .

[HSDB-4] Entry on 2,3-epoxypropyl methacrylate in the Hazardous Substances Data Bank , accessed on April 18, 2014.

[SIDS-5] OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for Glycidyl methacrylate , accessed on October 3, 2014.

[Gerhard_Lagaly,_Olivier_Schulz,_Ralf_Zimehl-6] Gerhard Lagaly, Olivier Schulz, Ralf Zimehl: dispersions and emulsions . Springer, 1997, ISBN 3-642-59248-1 , p. 220 ( limited preview in Google Book search).

[Judith_Pietschmann-7] Judith Pietschmann: Industrial powder coating: Basics, applications, processes . Springer, 2009, ISBN 3-8348-0463-0 , pp. 15 ( limited preview in Google Book search).

[8] RAC decision of December 4, 2015