Ethylene glycol dimethacrylate

Ethylene glycol dimethacrylate^[1]
	Skeletal formula
	Ball-and-stick model
Names
	Preferred IUPAC name Ethane-1,2-diyl bis(2-methylprop-2-enoate)
	Other names Methacrylic acid, ethylene ester; 1,2-Bis(methacryloyloxy)ethane; 1,2-Ethanediol dimethacrylate; Diglycol dimethacrylate; Ethanediol dimethacrylate; Ethylene dimethacrylate; Ethylene glycol bis(methacrylate); Ethylene glycol dimethacrylate; Ethylene methacrylate; 2-(Methacryloyloxy)ethyl methacrylate
Identifiers
CAS Number	97-90-5 ;
3D model (JSmol)	Interactive image;
Abbreviations	EGDMA
Beilstein Reference	1776663
ChEBI	CHEBI:53436 ;
ChEMBL	ChEMBL1709582;
ChemSpider	7077 ;
ECHA InfoCard	100.002.380
EC Number	202-617-2;
Gmelin Reference	637376
PubChem CID	7355;
RTECS number	OZ4400000;
UNII	7BK5G69305 ;
CompTox Dashboard (EPA)	DTXSID20891154 DTXSID1026615, DTXSID20891154 ;
	InChI InChI=1S/C10H14O4/c1-7(2)9(11)13-5-6-14-10(12)8(3)4/h1,3,5-6H2,2,4H3 Key: STVZJERGLQHEKB-UHFFFAOYSA-N ;
	SMILES CC(=C)C(=O)OCCOC(=O)C(=C)C;
Properties
Chemical formula	C10H14O4
Molar mass	198.218 g·mol−1
Density	1.051 g/mL
Melting point	−40 °C (−40 °F; 233 K)
Boiling point	98 to 100 °C (208 to 212 °F; 371 to 373 K) (5 mmHg)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H317, H319, H335, H412
Precautionary statements	P261, P264, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, P501
Flash point	101 °C (214 °F; 374 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Ethylene glycol dimethylacrylate (EGDMA) is a diester formed by condensation of two equivalents of methacrylic acid with ethylene glycol. It is a colorless viscous liquid.^[2] It is sometimes called ethylene dimethacrylate.^[3]

Polymerization

Containing a pair of reactive alkene groups, EGDMA is a crosslinking agent. Like other acrylates, it is susceptible free radical polymerization. When used with methyl methacrylate, it leads to gel point at relatively low concentrations because of the nearly equivalent reactivities of all the double bonds involved. As a monomer, It is used to prepare hydroxyapatite/poly methyl methacrylate composites.

Preparation

EGDMA is also synthesized by esterification of methacrylic acid with ethylene glycol:

2 H₂C=C(CH₃)CO₂H + HOCH₂CH₂OH → H₂C=C(CH₃)CO₂CH₂CH₂O₂C(CH₃)C=CH₂ + 2 H₂O

It also forms inadvertently in the hydroxyethylation of methacrylic acid, which is usually intended to give (hydroxyethyl)methacrylate:

2 H₂C=C(CH₃)CO₂H + CH₂CH₂O → H₂C=C(CH₃)CO₂CH₂CH₂O₂C(CH₃)C=CH₂ + H₂O

Safety

Its toxicity profile has been fairly well studied.^[4]

References

^ "Ethylene glycol dimethacrylate". Sigma-Aldrich.
^ Bielstein 2, IV, 1532
^ PubChem. "Ethylene glycol dimethacrylate". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-03-16.
^ Bielecka-Kowalska, Anna; Czarny, Piotr; Wigner, Paulina; Synowiec, Ewelina; Kowalski, Bartosz; Szwed, Marzena; Krupa, Renata; Toma, Monika; Drzewiecka, Malgorzata; Majsterek, Ireneusz; Szemraj, Janusz; Sliwinski, Tomasz; Kowalski, Michał (March 2018). "Ethylene glycol dimethacrylate and diethylene glycol dimethacrylate exhibits cytotoxic and genotoxic effect on human gingival fibroblasts via induction of reactive oxygen species". Toxicology in Vitro. 47: 8–17. doi:10.1016/j.tiv.2017.10.028.

[1] "Ethylene glycol dimethacrylate". Sigma-Aldrich.

[2] Bielstein 2, IV, 1532

[3] PubChem. "Ethylene glycol dimethacrylate". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-03-16.

[4] Bielecka-Kowalska, Anna; Czarny, Piotr; Wigner, Paulina; Synowiec, Ewelina; Kowalski, Bartosz; Szwed, Marzena; Krupa, Renata; Toma, Monika; Drzewiecka, Malgorzata; Majsterek, Ireneusz; Szemraj, Janusz; Sliwinski, Tomasz; Kowalski, Michał (March 2018). "Ethylene glycol dimethacrylate and diethylene glycol dimethacrylate exhibits cytotoxic and genotoxic effect on human gingival fibroblasts via induction of reactive oxygen species". Toxicology in Vitro. 47: 8–17. doi:10.1016/j.tiv.2017.10.028.

[1]

[2]

[3]

[4]