2-Hydroxyethyl Methacrylate

log Kow= 0.47

0.42

1.034 @ 25 °C/4 °C

1.07 g/cm³

1.034 @25 °C

Miscible with water and soluble in common org solvents

Solubility in water: miscible

97 °C (closed cup)

97 °C c.c.

67 °C @ 3.5 mm Hg

250 °C (calculated)

67 °C @760 [mm Hg]

Warning

H315: Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.2% (3 of 1898) of reports.

Warning

H315 (94.3%): Causes skin irritation [Warning Skin corrosion/irritation]

Chemical: 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester

2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl 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: 16-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15124

2-Hydroxyethyl methacrylate: Does not have an individual approval but may be used under an appropriate group standard

Allergic contact dermatitis reported in a laboratory technician and in the printing industry; A skin and eye irritant; [HSDB] Hydrolyzed forming methacrylic acid and ethylene glycol; A mild skin and moderate eye irritant; Possesses skin sensitizing properties with equivocal results in human patch testing; [Reference #2] A skin and severe eye irritant; May cause skin sensitization; [Alfa Aesar MSDS]

The substance will polymerize due to heating, on contact with peroxides, and under the influence of light. Heating may cause violent combustion or explosion. This produces acrid smoke. The substance may spontaneously polymerize if it is not stabilized.

Skin Irrit. 2 (94.3%)

Eye irritation - category 2A

Serious eye damage/eye irritation - Category 2A

Serious eye damage/eye irritation - Category 2

Skin corrosion/irritation - Category 2

Skin Irrit. 2

Fresh air, rest. Refer for medical attention.

First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer immediately for medical attention.

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/

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Personal protection: chemical protection suit and filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking liquid in covered containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

... 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: 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.

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.

LC50 Pimephales promelas (fathead minnows) 0.99 g/l/96 hr (95% confidence limit 0.90-1.1 g/l); age 30 days old, water hardness 45.6 mg/l calcium carbonate, temp 24.9 °C, pH 7.66, dissolved oxygen 7.1 mg/l, alkalinity 44.4 mg/l (CaCO3), Tank vol: 2.0 l, additions: 18 vol/day (flow-through bioassay)

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 43(SRC), determined from a log Kow of 0.47(2) and a regression-derived equation(3), indicates that 2-hydroxyethyl methacrylate is expected to have very high mobility in soil(SRC). Volatilization of 2-hydroxyethyl methacrylate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.6X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). 2-Hydroxyethyl methacrylate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.126 mm Hg(5). Screening tests indicate that 2-hydroxyethyl methacrylate is readily biodegradable; it reached 92-100% of its theoretical BOD in 2 weeks using an activated sludge inoculum(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 43(SRC), determined from a log Kow of 0.47(2) and a regression-derived equation(3), indicates that 2-hydroxyethyl methacrylate is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.6X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 1.3(SRC), from the log Kow(2), suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis of 2-hydroxyethyl methacrylate may be a significant process under basic conditions based upon a hydrolytic half-life of 4 hours at pH 11 for the structurally similar butyl acrylate(6); half-lives for butyl acrylate at pH 7, 8, and 9 were 4 years, 150 days, and 15 days(SRC), respectively, based upon a hydrolytic rate constant of 0.053 L/mole-sec(8). Screening tests indicate that 2-hydroxyethyl methacrylate is readily biodegradable; it reached 92-100% of its theoretical BOD in 2 weeks using an activated sludge inoculum(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-hydroxyethyl methacrylate, which has a vapor pressure of 0.126 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-hydroxyethyl methacrylate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 16 hours(SRC) from its estimated rate constant of 2.4X10-11 cu cm/molecule-sec at 25 °C(3). Because the structurally similar ethyl methacrylate does not absorb light in the environmental spectrum above 290 nm(4), direct photolysis of 2-hydroxyethyl methacrylate is not expected to occur(SRC).

Based on available data, the CIR Expert Panel concluded that...HEMA is safe as used in nail enhancement products when skin contact is avoided. Products containing these ingredients should be accompanied with directions to avoid skin contact, because of the sensitizing potential of Methacrylates.

Safe for use in cosmetics, with qualifications

Cough. Sore throat.

Redness.

Redness.

Sore throat. Aspiration hazard!

The Koc of 2-hydroxyethyl methacrylate is estimated as approximately 43(SRC), using a log Kow of 0.47(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2-hydroxyethyl methacrylate is expected to have very high mobility in soil.

LAB TECHNICIAN DEVELOPED ALLERGIC CONTACT DERMATITIS ASSOC WITH NAUSEA, DIARRHEA, & PERSISTENT PARESTHESIA OF FINGERTIPS. HYDROXYETHYLMETHACRYLATE WAS DEMONSTRATED TO PASS THROUGH VINYL GLOVES.

2-Hydroxy-ethyl methacrylate and di- and tetra-ethylene glycol dimethacrylates have produced contact sensitization in workers in the printing industry.

The Henry's Law constant for 2-hydroxyethyl methacrylate is estimated as 4.6X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-hydroxyethyl methacrylate is expected to be essentially nonvolatile from water surfaces(2) and from moist soil surfaces(SRC). 2-Hydroxyethyl methacrylate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.126 mm Hg(3).

TOXICOLOGICALLY, HYDROXYETHYL METHACRYLATE APPEARS ALMOST THREE TIMES AS TOXIC AS THE METHACRYLIC ETHYL ESTER.

INTRACORNEAL IMPLANTS OF PLASTIC FOILS MADE WITH HYDROXYETHYLMETHACRYLATE OR HYDROXYETHYLACRYLATE PLUS ETHYLENEGLYCOL DIMETHACRYLATE IN RABBITS PRODUCED EDEMA, VASCULARIZATION, NECROSIS, & ULCERATION & EVEN CHANGES IN THE PLASTICS THEMSELVES. CAUSATIVE AGENT NOT IDENTIFIED.

THE TOXICITY OF 6 ACRYLATES AND 6 METHACRYLATES, INCLUDING 2-HYDROXYETHYL METHACRYLATE, WAS DETERMINED IN RATS AND FISH. ALL THE ESTERS WERE LESS TOXIC THAN ACRYLAMIDE AND ACRYLONITRILE. METHACRYLATES WERE APPROXIMATELY 5-FOLD LESS TOXIC THAN ACRYLATES. FOR A GIVEN SERIES, TOXICITY DECREASED WITH INCREASING LENGTH OF THE CARBON CHAIN.

METHACRYLIC ACID ADMIN IV INCR RESPIRATORY RATE, DECR HEART RATE, & PRODUCED ELECTROCARDIOGRAM CHANGES IN ANESTHETIZED DOGS. METHACRYLIC ACID, METHYL, N-PROPYL, N-BUTYL, ISOBUTYL, AND HYDROXYETHYL METHACRYLATES PRODUCED A BIPHASIC RESPONSE, AN ABRUPT FALL IN BLOOD PRESSURE FOLLOWED BY A SECONDARY RISE. 2-ETHYLHEXYL, ISODECYL, LAURYL, AND TERT-BUTYLAMINOETHYL METHACRYLATES PRODUCED ONLY A HYPOTENSIVE EFFECT. DIMETHYLAMINOETHYLMETHACRYLATE PRODUCED ONLY A HYPERTENSIVE EFFECT.

TWENTY-ONE DIFFERENT ACRYLATE & METHACRYLATE COMPOUNDS, INCLUDING 2-HYDROXYETHYL 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.

CIR ingredient: HEMA

Frequently used in UV-curable inks and coatings; also used in adhesives, artificial nails, dental materials, and lacquers; [HSDB] Used in dentistry as one of the main volatile acrylates along with methyl methacrylate; [Reference #1] Used as a monomer in the synthesis of polymers (used in paints, adhesives, coatings, dental adhesive systems, etc.) for dental prosthetics, and for geotechnical grouting in construction work; [Reference #2]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

Acrylic resins; binder for nonwoven fabrics; enamels.

IN OPTOMETRY UTILIZED AS BASIC MATERIAL FOR CONTACT LENSES; AS DENTAL FILLER; IN PHARMACEUTICAL AREAS AS A DRUG RELEASE CONTROL MEDIUM; IN MEDICINE AS A SYNTHETIC WOUND DRESSING COMPONENT; AS A HYDROGEL FOR ORGAN GRAFTING; FOR SURFACE TENSION CONTROL IN BIOENGINEERING.

CROSSLINKING MONOMER FOR THERMOSET & UV CURABLE ACRYLICS.

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/

REACTION OF METHACRYLIC ACID WITH ETHYLENE OXIDE; TRANSESTERIFICATION OR ESTERIFICATION OF ETHYLENE GLYCOL WITH EITHER METHYL METHACRYLATE OR METHACRYLIC ACID.

Hydroxyalkyl methacrylates are prepared by the addition of methacrylic acid to the epoxide ring of alkylene oxides to form hydroxyalkyl methacrylates, ie, beta-hydroxyethyl and hydroxypropyl methacrylate. Oxides other than ethylene oxide give isomeric products; commercial hydroxypropyl methacrylate has about a 2-to-1 ratio of 2-hydroxypropyl methacrylate to 1-methyl-2-hydroxyethyl methacrylate. Effective catalysts include tertiary amines, anion-exchange resins, ferric chloride, and lithium methacrylate.

The 30% solution is made with xylene. Grades: 30%; 96%.

An inhibitor is usually added to solutions to prolong shelf life.

Commercial products contain hydroquinone methyl ether or similar polymerization inhibitors.

Adhesive Manufacturing

2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester: ACTIVE

METHYL METHACRYLATE, AND IN GENERAL THE METHACRYLIC ESTERS, POLYMERIZE MUCH LESS READILY THAN THE CORRESPONDING ORDINARY ACRYLATES. NONE THE LESS, THEY ARE STABILIZED BY ADDING HYDROQUINONE OR PYROGALLOL, PARTICULARLY IN THE PRESENCE OF METALLIC COPPER. /METHACRYLATES/

In hydrogel contact lenses