Basic information
- Standard SMILES
C=C(C)C(=O)OCCOC(=O)C(=C)C- InChIKey
STVZJERGLQHEKB-UHFFFAOYSA-N- Molecular formula
- C10H14O4
- Average molar mass
- 198.22 g/mol
- Monoisotopic mass
- 198.08920893
Overview
Ethylene glycol dimethacrylate is the enoate ester that is the 1,2-bis(methacryloyl) derivative of ethylene glycol. It has a role as a cross-linking reagent, an allergen and a polymerisation monomer. It is functionally related to a methacrylic acid and an ethylene glycol.
Names & identifiers
- Preferred name
- Ethylene glycol dimethacrylate
- IUPAC
- 2-(2-methylprop-2-enoyloxy)ethyl 2-methylprop-2-enoate
- English name
- Ethylene dimethacrylate
- Molecular formula
- C10H14O4
- Molecular weight
- 198.22
Names & synonyms
Show more names
Database identifiers
- CAS
97-90-5- PubChem CID
- 7355
- DTXSID
DTXSID1026615- ChEMBL
CHEMBL1709582- ChEBI
CHEBI:53436- UNII
- 7BK5G69305
- EC Number
- 202-617-2
- Nikkaji
- J38.144F
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 52.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 7
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 237
Experimental & physicochemical properties
Cosmetics
Cosmetic ingredients (Ethylene glycol dimethacrylate) -> CIR (Cosmetic Ingredient Review)
Cosmetic ingredients (Glycol Dimethacylate) -> CIR (Cosmetic Ingredient Review)
LogP
2.4
1.22
Density
1.055 at 20 °C/20 °C
Relative density (water = 1): 1.05
1.055 @ 20°C
Solubility
> 10% in benzene
> 10% in ethanol
> 10% in ligroin
Solubility in water, g/l at 20 °C: 1.1 (slightly soluble)
Boiling Point
260
260 °C
260 °C @760 [mm Hg]
Melting Point
-40 °C
-40 °C
Physicochemical properties
- Melting point
- -40 °C · -40 °C
- Boiling point
- 98 · 98-100 °C/5 mmHg (lit.)
- Density
- 1.051 g/mL · 1.051 g/mL at 25 °C (lit.)
- vapor density
- 1 · >1 (vs air)
- vapor pressure
- 0.1 mm · <0.1 mm Hg ( 21.1 °C)
- refractive index
- 20 · n20/D 1.454(lit.)
- Flash point
- 230 °F · >230 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 5 g/l · <5g/l
- form
- Liquid
- color
- Colorless to pale yellow
- Viscosity
- 3.06 mm2/s · 3.06mm2/s
- Water Solubility
- soluble
- α-end
- methacrylate
- Ω-end
- methacrylate
- BRN
- 1776663 · 1776663
- Stability
- Unstable - may polymerize upon exposure to light. Incompatible with strong acids, strong oxidizing agents, strong bases.
- Cosmetics Ingredients Functions
- NAIL CONDITIONING
- Cosmetic Ingredient Review (CIR)
- Ethylene dimethacrylate (97-90-5)
- InChI
- 1S/C10H14O4/c1-7(2)9(11)13-5-6-14-10(12)8(3)4/h1,3,5-6H2,2,4H3
- InChIKey
- STVZJERGLQHEKB-UHFFFAOYSA-N
- SMILES
- CC(=C)C(=O)OCCOC(=O)C(C)=C
- LogP
- 2.4 at · 2.4 at 20℃
- CAS DataBase Reference
- 97 · 97-90-5(CAS DataBase Reference)
- Indirect Additives used in Food Contact Substances
- ETHYLENE GLYCOL DIMETHACRYLATE
- FDA 21 CFR
- 177.101 · 177.1010; 177.2600
- EWG's Food Scores
- 3 · 3-6
- FDA UNII
- 7 BK5G69305 · 7BK5G69305
- NIST Chemistry Reference
- 2 · 2-Propenoic acid, 2-methyl-, 1,2-ethanediyl ester(97-90-5)
- EPA Substance Registry System
- Ethylene glycol dimethacrylate (97-90-5)
- Cosmetics Info
- Glycol HEMA-Methacrylate
- UNSPSC Code
- 12352108 · 12352108
- NACRES
- 23 · NA.23
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 317 · H317-H335
- Precautionary statements
- 261 · P261-P271-P272-P280-P302+P352-P304+P340+P312
- target organs
- Respiratory system
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xi
- Risk Statements
- 37 · 37-43
- Safety Statements
- 24 · 24-37-36/37
- RIDADR
- 3334 · UN 3334
- WGK Germany
- 1 · 1
- RTECS
- 4400000 · OZ4400000
- F
- 8 · 8-19
- TSCA
- TSCA listed
- HS Code
- 29161490 · 29161490
- Storage Class
- 10 · 10 - Combustible liquids
- Hazard Classifications
- 1 STOT · Skin Sens. 1STOT SE 3
- Hazardous Substances Data
- 97 · 97-90-5(Hazardous Substances Data)
- Toxicity
- 50 orally · LD50 orally in Rabbit: 3300 mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Warning
H317: May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P271, P272, P280, P302+P352, P304+P340, P319, P321, P333+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1326) of reports.
Warning
H317 (> 99.9%): May cause an allergic skin reaction [Warning Sensitization, Skin]
Hazard information
Regulatory Information
Chemical: 2-Propenoic acid, 2-methyl-, 1,2-ethanediyl ester
2-Propenoic acid, 2-methyl-, 1,1'-(1,2-ethanediyl) ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-methyl-, 1,1'-(1,2-ethanediyl) ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 05-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14351
Ethylene glycol dimethacrylate: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Allergic contact dermatitis reported in dental technicians, dental assistants, and a manufacturing worker (making rear-view mirrors) ; [Kanerva, p. 1749] A lachrymator; [CHEMINFO] An eye and respiratory tract irritant; Not a sensitizer in one study of guinea pigs; Emergency treatment: Acrylates, multifunctional; [HSDB] May polymerize; An eye and respiratory tract irritant; May cause skin sensitization; [ICSC] Danger of skin sensitization; [MAK] An irritant; May cause skin sensitization; [Aldrich MSDS]
Hazard Classes and Categories
Skin Sens. 1 (> 99.9%)
Specific target organ toxicity (single exposure) - category 3
Skin sensitization - Category 1
Skin sensitization - Category 1B
STOT SE 3
Safety & protection
First Aid Measures
Fresh air, rest.
Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse and then wash skin with water and soap.
Rinse with plenty of water (remove contact lenses if easily possible).
Rinse mouth.
Storage Conditions
Temp during storage must be kept low to minimize formation of peroxides and other oxidation products. ... Storage temp below 30 °C are recommended for the polyfunctional methacrylates. ... The methacrylate monomers should not be stored for longer than one year. Shorter storage times are recommended for the aminomethacrylates, ie, three months, and the polyfunctional methacrylates, ie, six months. Many of these cmpd are sensitive to UV light and should, therefore, be stored in the dark. The methacrylic esters may be stored in mild steel, stainless steel, or aluminum. /Methacrylic acid & derivatives/
Preventive Measures
... Hazard is the generation of considerable exothermic heat in some of the reactions, so that high pressures & temp may develop. This danger ... should be borne in mind when designing plant. Awareness of the dangers and of good engineering design are essential to safety. Employees should be instructed about the necessity of cleansing the skin if it is contaminated by materials which are irritants or skin-absorbed. With careful design, however, and complete enclosure of those processes where toxic chemicals or intermediates occur, dangerous exposures can be avoided. /Acrylic acid & derivatives/
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
Toxicology
TSCA Test Submissions
The ability of ethylene dimethacrylate to induce mutations at the TK gene locus in L5178Y mouse lymphoma cells was evaluated in vitro. Cells were exposed to test article at concentrations ranging from 31.3 to 800 nl/ml both with and without Aroclor-induced rat liver S9 metabolic activation. In the presence of activation, a 2.4 to 10 fold increase in mutation frequency was observed in cells exposed to concentrations ranging from 400 to 700 nl/ml, while the percent relative growth decreased from 78.3 to 33.6%. In the absence of activation, exposure to concentrations of up to 800 nl/ml caused high toxicity but no increase in mutation rate.
Human Toxicity Excerpts
BIOLOGICALLY, METHACRYLATES RESEMBLE ACRYLATES, EXCEPT FOR LOWER REACTIVITY & THUS DECR TOXICITY. THIS IS PROBABLY DUE TO STERIC HINDRANCE BY ITS METHYL GROUP & IN TURN DECR RATES OF MEMBRANE TRANSPORT & SYSTEMIC TRANSLOCATION. /METHACRYLIC ESTERS/
Non-Human Toxicity Excerpts
TWENTY-ONE DIFFERENT ACRYLATE & METHACRYLATE COMPOUNDS, INCLUDING ETHYLENE METHACRYLATE, WERE SCANNED FOR THEIR ABILITY TO INDUCE CONTACT SENSITIVITY, USING 5 DIFFERENT SENSITIZATION PROTOCOLS. CONTACT REACTIONS OF VARYING INTENSITIES WERE PRODUCED TO ALL THE MONO-, DI-, AND TRIACRYLATES TESTED. METHACRYLATES DID NOT SENSITIZE GUINEA PIGS.
Regulatory information
Safety data
- F
- 8-19
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- OZ4400000
- ridadr
- UN 3334
- hs_code
- 29161490
- Toxicity
- LD50 orally in Rabbit: 3300 mg/kg
- risk_code
- 37-43
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 24-37-36/37
- Storage Class
- 10 - Combustible liquids
- target organs
- Respiratory system
- Hazard statements
- H317-H335
- REACH Registrations
- Active
- Hazard Classifications
- Skin Sens. 1STOT SE 3
- Precautionary statements
- P261-P271-P272-P280-P302+P352-P304+P340+P312
- Hazardous Substances Data
- 97-90-5(Hazardous Substances Data)
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Reagents with two reactive groups, usually at opposite ends of the molecule, that are capable of reacting with and thereby forming bridges between side chains of amino acids in proteins; the locations of naturally reactive areas within proteins can thereby be identified; may also be used for other macromolecules, like glycoproteins, nucleic acids, or other.
Uses & manufacturing
Uses
CIR ingredient: Ethylene glycol dimethacrylate
CIR ingredient: Glycol Dimethacylate
In polymers for dental restorative resins; in synthetic wound dressings; as rate-controlling barrier in slow release capsules; in acrylic nail preparation; as curing agent for acrylics and rubbers; [HSDB]
Plastic Composites Manufacturing [Category: Industry]
/SRP/: IN POLYMERS FOR DENTAL RESTORATIVE RESINS; IN SYNTHETIC WOUND DRESSINGS; AS RATE-CONTROLLING BARRIER IN SLOW RELEASE CAPSULES; IN ACRYLIC NAIL PREPN.
CROSSLINKING AGENT FOR THERMOSET & UV CURABLE ACRYLICS.
U.S. Production
2023: 2,500,000 - <4,000,000 lb
(1979) PROBABLY GREATER THAN 4.54X10+6 G
(1981) PROBABLY GREATER THAN 2.27X10+6 G
Methods of Manufacturing
TRANSESTERIFICATION OR ESTERIFICATION OF ETHYLENE GLYCOL WITH AN EXCESS OF EITHER METHYL METHACRYLATE OR METHACRYLIC ACID
The methacrylates can be synthesized by catalytic oxidation of isobutylene and subsequent esterification with the appropriate alcohol, or by reacting acetone with hydrocyanic acid and subsequent esterification in sulfuric acid with the appropriate alcohol. /Methacrylic esters/
General Manufacturing Information
Printing and Related Support Activities
2-Propenoic acid, 2-methyl-, 1,1'-(1,2-ethanediyl) ester: ACTIVE
Applications
DescriptionIt is mainly applied in the field of organic synthesis, such as a crosslinking agent for fabricating resin, resin processing, fabricating adhesives and coatings, rubber resin modifier, anaerobic adhesive, and plastic paste. Specifically, this chemical can be used as the raw material to prepare a copolymer that has been demonstrated to act as a biocompatible interface between glucose biosensors and tissue in the rat.1 Moreover, this compound may be involved in the preparation of poly(2-vinyl-4,4-dimethylazlactone-co-acrylamide-co-ethylene dimethacrylate) for designing the porous support for high throughput reactors.2 In addition, the bulk polymerization of this chemical and glycidyl methacrylate results in the formation of porous monolith as a stationary phase in dye-affinity chromatography.3
DescriptionThe crosslinking agent of acrylic resins, ethyleneglycol dimethacrylate (EGDMA), is employed to optimize the dilution of high-viscosity monomers and to link together the macromolecules costituting the polymer. It caused contact dermatitis in dental technicians and dental assistants. A case was also reported in a car rear-view mirror manufacturer.
UsesEthylene glycol dimethacrylate is used as a functional monomer for polymers and as a cross linking agent between the molecular chains of polymers and elastomers. It is also used in free radical copolymer cross linking reactions. It acts as an intermediate in the production of hydroxyapatite and poly methyl methacrylate composites. It is also used in dentaI composites, sealants, prostheses, adhesives, artificiaI nails, printing inks, etc.
General DescriptionEthylene glycol dimethylacrylate (EGDMA) is a diester formed by condensation of two equivalents of methacrylic acid and one equivalent of ethylene glycol.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
DefinitionChEBI: Ethylene glycol dimethacrylate is the enoate ester that is the 1,2-bis(methacryloyl) derivative of ethylene glycol. It has a role as a cross-linking reagent, a polymerisation monomer and an allergen. It is functionally related to an ethylene glycol and a methacrylic acid.
Related reactions
Linked notes
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