2-Hydroxyethyl acrylate

log Kow = -0.21

-0.21

-0.21

1.1 at 77 °F (USCG, 1999) - Denser than water; will sink

1.011 g/cu cm at 23 °C

Liquid heat capacity = 0.491 BTU/lb-F at 70 °F; Liquid thermal conductivity = 1.048 BTU-in/hr-sq ft-F at 70 °F; Liquid viscosity: 5.438 cP at 70 °C; Saturated vapor pressure = 0.090 lb/sq in at 177 °F; Saturated vapor density = 0.00153 lb/cu ft at 177 °F

1.1 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.0

1.011 @25 °C

Liquid

Clear colorless liquid

In water, miscible /1X10+6 mg/L/ at 25 °C

Solubility in water: miscible

214 °F (NFPA, 2010)

214 °F (101 °C) (closed cup)

101 °C c.c.

greater than 346 °F at 760 mmHg (USCG, 1999)

191 °C

BP: 40 °C at 0.001 kPa (0.0075 mm Hg)

Boiling point: 40 °C at 0.001 kPa

210 °C

220 °C @760 [mm Hg]

Danger

H311: Toxic in contact with skin [Danger Acute toxicity, dermal]

P260, P261, P262, P264, P270, P272, P273, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P333+P317, P361+P364, P362+P364, P363, P391, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1484) of reports.

Danger

H302 (54%): Harmful if swallowed [Warning Acute toxicity, oral]

Chemical: 2-Propenoic acid, 2-hydroxyethyl ester

2-Propenoic acid, 2-hydroxyethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 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)

REACH registered substance: 2-hydroxyethyl acrylate (EC: 212-454-9)

Poly(oxy-1,2-ethanediyl), .alpha.-(1-oxo-2-propenyl)-.omega.-hydroxy-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

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

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Behavior in Fire: Containers may explode (USCG, 1999)

Combustible. Heating will cause rise in pressure with risk of bursting.

Organization for Economic Cooperation and Development; Screening Information Data Set for Hydroxyethyl acrylate, CAS No. 818-61-1 (April 2005). This OECD Initial Assessment of HPV Chemicals is part of a series of OECD SIDS documents published by UNEP Chemicals to facilitate the access to information needed for health and environmental risk assessments of chemicals.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Use water spray, dry powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest. Half-upright position. Refer immediately for medical attention.

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

Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention.

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

Water or foam may cause frothing.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature 2 - 8 °C

The effectiveness of phenolic inhibitors is dependent on the presence of oxygen and the monomers must be stored under air rather than an inert atmosphere. Temp must be kept low to minimize formation of peroxides and other products. ... The acrylic esters may be stored in mild or stainless steel, or aluminum. /Acrylic acid & derivatives/

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

LC50; Species: Pimephales promelas (Fathead minnows) age 28 days, mean length 18.5 mm, mean weight 0.110 g; Conditions: flow through, 24.5 °C, pH 7.69, hardness 44.0 mg/L (CaCO3), alkalinity 49.8 mg/L (CaCO3), dissolved oxygen 7.1 mg/L; Concentration: 4.8 mg/L for 96 hr />97% purity/

LC50; Species: Cyprinodon variegatus (Sheepshead minnow); Conditions: flow-through; Concentration: 17.5 mg/L for 96 hr

EC50; Species: Daphnia magna (water flea); Conditions: static (OECD Guideline 292), pH 8.1-8.2, temperature 22 °C; Concentration: 0.78 mg/L for 48 hr (95% confidence limits 0.64-0.95 mg/L); Effect: mobility

EC50; Species: Pseudokirchneriella subcapitata (green algae); Conditions: static (OECD Guideline 201); Concentration: 4.12 mg/L for 96 hr (95% confidence interval: 3.75-4.52 mg/L); Endpoint: biomass

EC50; Species: Pseudokirchneriella subcapitata (green algae); Conditions: static (OECD Guideline 201); Concentration: 8.26 mg/L for 96 hr (95% confidence interval: 7.62-8.95 mg/L); Endpoint: growth rate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 2-hydroxyethyl acrylate is expected to have very high mobility in soil(SRC). Volatilization of 2-hydroxyethyl acrylate from moist soil surfaces is not expected(SRC) given an estimated Henry's Law constant of 8.0X10-9 atm-cu m/mole(SRC) based upon its vapor pressure, 0.0523 mm Hg(3), and assigned value for water solubility of 1X10+6 mg/L (miscible)(4). 2-Hydroxyethyl acrylate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). A 78% of Theoretical BOD using activated sludge in the Japanese MITI test(5) suggests that biodegradation is an important environmental fate process in soil(SRC). The degradation rate of 2-hydroxyethyl acrylate in soil was 3.6X10-7/s based on calculations using a chemical pollution footprint methodology(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 2-hydroxyethyl acrylate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 8.0X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 0.052 mm Hg(4), and assigned value for water solubility of 1X10+6 mg/L (miscible)(5). A hydrolysis half-life of >270 days at pH 7 for 2-hydroxyethyl acrylate was reported, the hydrolysis half-life decreases with increase pH indicating that 2-hydroxyethyl acrylate may undergo slow hydrolysis under basic conditions(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow of -0.21(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low. Utilizing the Japanese MITI test, 78% of the Theoretical BOD was reached in 4 weeks(8) indicating that biodegradation is an important environmental fate process in water(SRC). Degradation rates of 2-hydroxyethyl acrylate in water and sediment were 7.2X10-7/s and 8.0X10-8/s, respectively, based on calculations using a chemical pollution footprint methodology(9).

Following the 2.5 mg/kg and 50 mg/kg oral dose /in Fisher 344 male rats/, the half-lives for the terminal phase of elimination via (14)CO2 were determined to be approximately 15, and 14 hr, respectively. The half-lives for the initial phase of elimination were 1.9, and 1.8, respectively. The half life of elimination of radioactivity in the urine following oral administration were 10, and 9 hr for the 2.5 mg/kg bw oral and 50 mg/kg bw oral treatment groups, respectively.

2-hydroxyethyl acrylate (HEA) has been evaluated in a study that examined metabolism and excretion in male Fischer 344 rat using oral, intraperitoneal, dermal and inhalation routes of exposure ... For the oral and intraperitoneal routes of exposure the rats (four animals/dose level/route of exposure) received a single dose of (14)C-HEA at 2.5 or 50 mg/kg bw. For the inhalation exposure, six rats were exposed to a target concentration of 8 ppm (14)C-HEA for six hours in a head only inhalation chamber. For the dermal exposure, four rats were treated with (14)C-HEA at a dose of 50 mg/kg. No qualitative differences in urinary metabolites between routes were observed, indicating no marked route-dependent differences in the metabolic fate of HEA. The results of the study indicate that once the chemical becomes systemically available it is rapidly metabolized and eliminated from the body as either CO2 in the expired air or urinary metabolites with approximately equal percentage of administered/exposed dose eliminated by each route. The half-lives of elimination of radioactivity were approximately 14 hours for urine and 17 hours for CO2. The halflife of elimination of radioactivity from plasma was approximately 26 hours although the label was not associated with parent HEA. The available metabolic data on HEA is consistent with information on studies with other acrylates where hydrolysis of the ester functionality is the primary metabolic pathway. By analogy with ethyl acrylate and acrylic acid, it is expected that a minor metabolic pathway for HEA will be via conjugation with glutathione with the resulting mercapturic acid derivatives being excreted in the urine.

The metabolism and excretion of HEA has been examined in male Fischer 344 rat using oral, intraperitoneal, dermal and inhalation routes of exposure ... For the oral and intraperitoneal routes of exposure the rats (4 animals/dose level/route of exposure) received a single dose of 2.5 or 50 mg/kg bw (approx 15-20 uCi). For the inhalation exposure six rats were exposed to a target concentration of 8 ppm (14)C HEA for 6 hours in a head only inhalation chamber. For the dermal exposure 4 rats were treated with (14)C HEA at a dose of 12.5 mg/kg bw. No qualitative differences in urinary metabolites between routes were observed, indicating no marked route-dependent differences in the metabolic fate of HEA. The results of the study indicate that once the chemical becomes systemically available it is rapidly metabolized and eliminated from the body as either CO2 in the expired air or urinary metabolites. The available metabolic data on HEA is consistent with information on substances with other acrylates where hydrolysis of the ester functionality is the primary metabolic pathway. By analogy with ethyl acrylate and acrylic acid it is expected that a minor metabolic pathway for HEA will be via conjugation with glutathione with the resulting mercapturic acid derivatives being excreted in the urine. For the oral and intraperitoneal routes (2.5 mg/kg bw) 35-36% of the administered dose was expired as (14)CO2 and 43-47% of the dose excreted via the urine by 48 hours post-dosing. At 50 mg/kg bw 40-45% of the dose was expired as (14)CO2 and 33-36% of the dose was excreted in the urine. Following dermal administration 66% of the dose was absorbed within 48 hours of the application with remaining 33% being associated with the application site. Of the absorbed dose 27% was excreted in the urine as metabolites of HEA and 27% was excreted in the expired air as (14)CO2. For inhalation 39% of the absorbed dose was eliminated in the urine by 48 hr and 41% was expired as (14)CO2. For all routes, 9-16% was found in the tissues and carcass and less than 3% in the feces.

Following oral administration of (14)C-HEA to Fisher 344 male rats, between 91 and 95% of the administered radioactivity was recovered in the urine, CO2, feces, tissues and carcass, volatile organics and final cage wash. At the low dose of 2.5 mg (14)C-HEA/kg body weight, for the oral route of administration, approximately 43-47 % of the dose was eliminated in the urine, the primary elimination route, whereas 35-36% of the dose was expired as (14)CO2, and the tissues and carcass accounted for between 9-13 % of the dose. Less than 1.5% of the administered dose of radioactivity was recovered in the feces and less than 1% was found in the final cage wash. Less than 0.2% of the dose was recovered as volatile organics in the expired air. At the higher dose of 50 mg/kg (14)C-HEA/kg body weight, for the oral route of administration, 33-36% of the dose was eliminated in the urine, whereas 40-45% of the dose was expired as (14)CO2. At this higher dose there was a shift from the urinary pathway as the primary route of elimination to the exhalation of (14)CO2 as the primary route of elimination. As with the 2.5 mg/kg dose, the tissues and carcass accounted for 10-13% of the dose and less than 0.6% of the recovered radioactivity was in the final cage wash, less than 0.1% was recovered as volatile organics in the expired air and less than 2.5% of the dose was recovered in the feces. Following the oral route of administration, 0.3-1.5% of the dose was expired as (14)CO2 as early as 15 minutes post-dosing. The peak of CO2 excretion occurred during or before the 4-8 hr collection interval. By 12 hr post-dosing with 2.5 mg/kg for the oral route of administration, 31-32 of the dose was expired as (14)CO2. For this same collection interval following 50 mg/kg oral administration, 41 of the dose was expired as (14)CO2. The exhalation of (14)CO2 derived from (14)C-HEA appeared to follow first-order kinetics as a biphasic process, except following dermal administration. Following oral administration, greater than 92% of the total radioactivity excreted via the urine was excreted during the first 12 hr collection interval.

Used in media for electron microscope preparations; also used in UV-cured artificial nails; [Kanerva, p. 1742]

HEA is used mainly either as a co-monomer in the manufacture of polymers or as a chemical reactant in the manufacture of chemical intermediates. In the manufacture of polymers, HEA can be co-polymerized with acrylic acid, acrylates, methacrylates, vinyl acetate, vinyl chloride, vinylidene chloride, styrene, butadiene, and the like. Co-reactants with HEA include aromatic and aliphatic isocyanates, anhydrides, and epoxides. The polymers and chemical intermediates made with HEA find applications in automotive top coatings, architectural coatings, photocure resins, and adhesives. Globally about half of the HEA produced is used in the production of acrylic enamels for the automotive industry, where a clear topcoat is applied to a pigmented base coat to increase corrosion protection and durability.

... Cross-linking agents in heat-cured paints, adhesives, textile preparations, etc.

Functional monomer for the manufacture of thermosetting acrylic resins.

In acrylate grouts

MEDICATION

96%, contains 200-650 ppm monomethyl ether hydroquinone as inhibitor.

Other esters < 2% w/w; dietylene glycol monoacrylate < or = 2.1% w/w; acrylic acid < or = 1% w/w; ethylene glycol approx 0.25% w/w; ethylene oxide approx 0.001% w/w

2023: 4,000,000 - <5,500,000 lb

(1974) > 4.54 X 10+5 g

(1975) > 4.54 X 10+5 g

(2001) 10 x 10+3 tons (US)

(2001) 15 x 10+3 tons (world)

For more U.S. Production (Complete) data for 2-Hydroxyethyl acrylate (8 total), please visit the HSDB record page.