2-Hydroxypropylacrylat

log Kow = 0.35

0.35

0.35

1.05 kg/L at 25 °C

Relative density (water = 1): 1.1

1.05

1.05

Liquid

Colorless liquid

Miscible with water

Miscible with oxygenated solvents

Solubility in water, g/100ml at 25 °C: 100 (good)

149 °F (closed cup)

65 °C

207 °F

149 °F

BP: 70 °C at 2 mm Hg

BP: 63 °C at 0.04 kPa (0.3 mm Hg)

BP: 77 °C at 5 mm Hg

191 °C

376 °F

376 °F

When heated to decomposition it emits acrid smoke and fumes.

Hazardous decomposition products formed under fire conditions. - Carbon dioxide (CO2)

0.17 [mmHg]

Vapor pressure, Pa at 20 °C: 5

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P270, P271, P272, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P333+P317, P361+P364, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H301+H331 (25.9%): Toxic if swallowed or if inhaled [Danger Acute toxicity, oral; acute toxicity, inhalation]

P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P333+P317, P361+P364, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Chemical: 2-Propenoic acid, 2-hydroxypropyl ester

2-Hydroxypropyl acrylate: 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.

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.)

May cause skin burns; may cause pulmonary edema after heavy inhalation exposure; [ICSC] A potential dermal sensitizer, based on weak animal data; Rats died after 4-hour exposures to 650 ppm and showed signs of eye, nasal, and respiratory irritation. [ACGIH]

The substance may polymerize due to heating and under the influence of light, and peroxides. Decomposes on heating. This produces toxic and corrosive fumes including acrolein. Reacts violently with strong acids, strong bases, strong oxidants and peroxides. This generates fire hazard.

Lower 1.4 at 212 °F (100 °C)

Class IIIA Combustible Liquid: Fl.P. at or above 140 °F and below 200 °F.

3 - Materials that, under emergency conditions, can cause serious or permanent injury.

1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.

2 - Materials that readily undergo violent chemical changes at elevated temperatures and pressures.

Acute Tox. 3 (100%)

Acute toxicity - category 3

Acute toxicity (Oral) - Category 4

Acute toxicity (Oral) - Category 4

Corrosives, Flammable agents - 2nd degree

Acute Tox. 3 *

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

Remove contaminated clothes. Rinse skin with plenty of water or shower for at least 15 minutes. 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. Refer immediately for medical attention.

Extinguishing methods: Alcohol foam

If material on fire or involved in fire: Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical, or carbon dioxide. Use water spray to knock-down vapors.

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. Further information: Use water spray to cool unopened containers.

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. Storage class (TRGS 510): 6.1B: Non-combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low 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: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal.

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Product: This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product.

Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking liquid in covered containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low 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.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

Personnel protection: Avoid breathing vapors. Keep upwind. Avoid bodily contact with the material. Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.

For more Preventive Measures (Complete) data for 2-Hydroxypropyl acrylate (8 total), please visit the HSDB record page.

LC50; Species: Pimephales promelas (Fathead minnow) juvenile age 28-34 days, weight 0.134 g, length 20.9 mm; Conditions: freshwater, flow through, hardness 45.3 mg/L CaCO3, alkalinity 47.0 mg/L CaCO3; Concentration: 3100 ug/L for 96 hr />97% purity/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.4(SRC), determined from a structure estimation method(2), indicates that 2-hydroxypropyl acrylate is expected to have very high mobility in soil(SRC). Volatilization of 2-hydroxypropyl acrylate from moist soil surfaces is not expected(SRC) given an estimated Henry's Law constant of 1.7X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). 2-Hydroxypropyl acrylate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.17 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). A 83% of Theoretical BOD using activated sludge in the Japanese MITI test(3) suggests that biodegradation is an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.4(SRC), determined from a structure estimation method(2), indicates that 2-hydroxypropyl 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 1.7X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). A hydrolysis half-life of >230 days at pH 7 for the commercial hydroxypropyl acrylate isomer mixture was reported, the hydrolysis half-life decreases with increase pH indicating that 2-hydroxypropyl acrylate may undergo slow hydrolysis under basic conditions(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of 0.35(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low. The percent Theoretical BOD of the commercial hydroxypropyl acrylate isomer mixture reached 83% after 4 weeks in the Japanese MITI test(7) and 34.9% after 4 weeks in a closed bottle test for ready biodegradability(4). These results indicate that biodegradation will be an important fate process for 2-hydroxypropyl acrylate in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-hydroxypropyl acrylate, which has an estimated vapor pressure of 0.17 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-hydroxypropyl acrylate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone(SRC); the half-lives for these reactions in air are estimated to be 19 hours and 6.5 days(SRC), calculated from its respective rate constants of 2.0X10-11 and 1.7X10-18 cu cm/molecule-sec at 25 °C(SRC) that were derived using a structure estimation method(2). 2-Hydroxypropyl acrylate contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The substance can be absorbed into the body through the skin and by ingestion. Serious local effects by all routes of exposure.

inhalation, skin absorption, ingestion, skin and/or eye contact

IDENTIFICATION AND USE: 2-Hydroxypropyl acrylate (HPA) is a colorless liquid. It is used in manufacture of thermosetting resins for surface coatings. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: Instillation of 0.1 mL in rabbit eye produced prompt, severe ocular irritation and corneal injury. In rabbits topical HPA application causes moderate burns (even when contacted as a 10% aqueous solution). Rats inhaling saturated HPA vapor generated at room temperature for 7 to 8 hours survived, but those exposed for 4 hours at approximately 650 ppm HPA vapor (generated at 100 °C) died either during exposure or within 1 hour after cessation of exposure. Marked signs of eye, nasal, and respiratory irritation were noted during the exposure period. When dogs were repeatedly exposed by inhalation at 5 ppm 6 hours/day, 5 days/week for a total of 20 or 21 days during a 1-month period, signs of ocular, nasal, and respiratory tract irritation were observed, and histologic testicular changes were seen in 3 of the 4 exposed animals. HPA was tested for mutagenicity in Salmonella typhimurium strains TA102 and TA2638 (with metabolic activation) and Escherichia coli strains WP2/pKM101 and WP2 uvrA/pKM101. It was found positive in the Escherichia coli strains.

Cough. Sore throat. Burning sensation. Shortness of breath. Laboured breathing.

MAY BE ABSORBED! Redness. Pain. Skin burns. Blisters.

Redness. Pain. Blurred vision. Severe deep burns.

Burns in mouth and throat. Abdominal pain. Vomiting. Shock or collapse.

irritation eyes, skin, respiratory system; eye, skin burns; cough, dyspnea (breathing difficulty)

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2-hydroxypropyl acrylate can be estimated to be 1.4(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-hydroxypropyl acrylate is expected to have very high mobility in soil.

AEROBIC: Biodegradation data specific to 2-hydroxypropyl acrylate were not located; however, results from ready biodegradation studies are available for the commercial hydroxypropyl acrylate isomer mixture which contains 75-80% 2-hydroxypropyl acrylate and 25-30% 1-methyl-2-hydroxyethyl acrylate(1-2). Hydroxypropyl acrylate, present at 100 mg/L, reached 83% of its Theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(1). Hydroxypropyl acrylate, present at 3 mg/L, reached 34.9% of its Theoretical OD after 4 weeks using a domestic activated sludge inoculum in the closed bottle test for ready biodegradability(2). In a similar test, hydroxypropyl acrylate was biodegraded 73% after 20 days(2).

An estimated BCF of 3 was calculated in fish for 2-hydroxypropyl acrylate(SRC), using a log Kow of 0.35(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

The goal of these studies was to measure and interpret the skin permeability characteristics of 2-hydroxypropyl acrylate (HPA) as a model compound that is completely miscible with water. METHODS: In vitro permeation from HPA-H2O binary mixtures through human epidermis and silicone membranes was measured. Thermodynamic activities of HPA and H2O in these mixtures were determined. Permeation was also measured through epidermis and silicone from donor solutions with constant HPA activity but different H2O activities. Water uptake into desiccated human stratum corneum (SC) equilibrated with HPA-H2O mixtures was determined. RESULTS: Steady-state flux of HPA through silicone was a linear function of HPA activity but not HPA concentration. For epidermis on the other hand, flux increased with HPA activity only for HPA activities = 0.35. At constant HPA activity, flux decreased 4.5-fold as water activity decreased from 1 to 0.8. Incubation of SC with HPA-H2O mixtures resulted in substantial changes in SC water content, dependent on the water activity of the mixture and consistent with measured SC water sorption data. CONCLUSIONS: These experiments provide unequivocal evidence of a substantial increase in epidermal barrier function resulting from SC dehydration. Dehydration-related alterations in the SC appear responsible for the observed flux characteristics.

Used in the manufacture of thermosetting resins in surface coatings; [ACGIH]

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

It is used to make plastics.

In manufacture of thermosetting resins for surface coatings.

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

Reactive comonomer (acrylic, vinyl acetate, styrene-butadiene, nitrile resins)

... Produced by liquid-phase esterification of acrylic acid with ... propylene oxide in the presence of a Lewis acid catalyst, such as a chromium or ruthenium compound, or the iron salt of an organic acid.

Hydroxyethyl and 2-hydroxypropyl acrylates are prepared by the addition of ethylene oxide or propylene oxide to acrylic acid. The reactions are catalyzed by tertiary amines, quaternary ammonium salts, metal salts, and basic ion-exchange resins. The products are difficult to purify and generally contain low concentrations of acrylic acid and some diester which should be kept to a minimum since its presence leads to product instability and to polymer cross-linking.

Hydroxyethyl and 2-hydroxypropyl acrylates are prepared by the addition of ethylene oxide or propylene oxide to acrylic acid. The reactions are catalyzed by tertiary amines, quaternary ammonium salts, metal salts, and basic ion-exchange resins. The products are difficult to purify and generally contain low concentrations of acrylic acid and some diester which should be kept to a minimum since its presence leads to product instability and to polymer cross-linking.