2-Ethyl-2-[[(1-oxoallyl)oxy]methyl]-1,3-propandiyldiacrylat

log Kow = 2.75

2.75

Liquid; Dry Powder; CBI

Liquid; [IUCLID] Colorless liquid with a pungent odor; Hygroscopic; Tan or amber in color if impure; [NTP] Clear or yellow liquid with a pungent odor; [Alfa Aesar MSDS]

Warning

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

P203, P261, P264, P264+P265, P272, P273, P280, P302+P352, P305+P351+P338, P318, P321, P332+P317, P333+P317, P337+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.1% (4 of 3852) of reports.

Warning

H315 (99.9%): Causes skin irritation [Warning Skin corrosion/irritation]

Chemical: 2-Propenoic acid, 2-ethyl-2-[[(1-oxo-2-propenyl)oxy]methyl]-1,3-propanediyl ester

Hazard Traits - Carcinogenicity

2-Propenoic acid, 1,1'-[2-ethyl-2-[[(1-oxo-2-propen-1-yl)oxy]methyl]-1,3-propanediyl] ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 1,1'-[2-ethyl-2-[[(1-oxo-2-propen-1-yl)oxy]methyl]-1,3-propanediyl] 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: 04-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15232

Trimethylolpropane triacrylate: Does not have an individual approval but may be used under an appropriate group standard

Allergic contact dermatitis reported in workers exposed to UV-cured coatings and textile inks; [Kanerva, p. 1745] Labeled in the EU as causing skin and eye irritation with the potential to cause skin sensitization; [IUCLID] May spontaneously polymerize on exposure to heat or light (stabilized with monomethyl ester of hydroquinone); [NTP] Occupational asthma confirmed in a worker exposed for 20 years in a kiosk to a tint containing trimethylolpropane triacrylate from a thermal printer; [Reference #1]

Skin Irrit. 2 (99.9%)

Eye irritation - category 2

Skin corrosion/irritation - Category 2

Serious eye damage/eye irritation - Category 2A

Carc. 2

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. 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 soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1510(SRC), determined from a structure estimation method(2), indicates that trimethylolpropane triacrylate is expected to have low mobility in soil(SRC). Volatilization of trimethylolpropane triacrylate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Trimethylolpropane triacrylate's estimated vapor pressure of 5.9X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), suggests that volatilization from dry soil surfaces will not be important fate process(SRC); however, trimethylolpropane triacrylate is a liquid with a noticeable acrylic odor(3) suggesting some volatilization may occur(SRC). A 19% of theoretical BOD using activated sludge in the Japanese MITI test(4) suggests that some biodegradation may occur in soil(SRC); in the 4-week biodegradation test, 87% of initial trimethylolpropane triacrylate was degraded yielding the di- and monoacrylate esters plus trimethylolpropane(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1510(SRC), determined from a structure estimation method(2), indicates that trimethylolpropane triacrylate is 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 6X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 30(SRC), from a log Kow of 2.75(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low. Bioconcentration tests using 6 or 8 week exposures found low bioconcentration(6). A base-catalyzed second-order hydrolysis rate constant of 0.0242 L/mole-sec at 25 °C(SRC) was estimated using a structure estimation method(7); this corresponds to half-lives of 9 years and 331 days at pH values of 7 and 8, respectively(SRC). A 19% of theoretical BOD using activated sludge in the Japanese MITI test(6) suggests that some biodegradation may occur in soil(SRC); in the 4-week biodegradation test, 87% of initial trimethylolpropane triacrylate was degraded yielding the di- and monoacrylate esters plus trimethylolpropane(6).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trimethylolpropane triacrylate, which has an estimated vapor pressure of 5.9X10-4 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 trimethylolpropane triacrylate 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 11 hours(SRC), calculated from its rate constant of 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Vapor-phase trimethylolpropane triacrylate is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 2 days(SRC), calculated from its rate constant of 5.25X10-18 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Trimethylolpropane triacrylate is reported to be light sensitive when exposed to direct sunlight(3); therefore, direct photolysis may have some importance in the environment(SRC).

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from, as of June 21, 2012: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=15625-89-5]

Using a structure estimation method based on molecular connectivity indices(1), the Koc of trimethylolpropane triacrylate can be estimated to be 1510(SRC). According to a classification scheme(2), this estimated Koc value suggests that trimethylolpropane triacrylate is expected to have low mobility in soil.

/HUMAN EXPOSURE STUDIES/ Skin sensitivity and photo patch testing of 0.2% trimethylolpropane triacrylate in petrolatum was performed on 47 employees of a citrus juice bottling plant who were exposed to ultraviolet-cured printing inks. All 47 workers had positive reactions to one or both tests. Because few workers showed skin sensitization to trimethylolpropane triacrylate, the past skin reactions were considered to be irritant, not allergic, reactions to the inks and their components.

/HUMAN EXPOSURE STUDIES/ Four workers in a plastic floor manufacturing facility developed hand and face dermatitis a year after the introduction of a varnish with an aziridine-based hardener containing 3% to 5% trimethylolpropane triacrylate. The workers had positive reactions to skin patch tests with trimethylolpropane triacrylate in acetone at 0.0001% (1/4), 0.03% (3/4), and 0.1% (4/4), with the most severe reactions occurring in the worker who reacted to the 0.0001% formulation.

/HUMAN EXPOSURE STUDIES/ Seven of 10 workers exposed to ultraviolet-curable printing inks at a plastic food container manufacturing plant developed contact dermatitis; one person had a positive reaction for sensitization to 0.1% trimethylolpropane triacrylate in petrolatum.

/HUMAN EXPOSURE STUDIES/ /Investigators/ reported the development of allergic dermatitis in six people who worked with ultraviolet-curable inks containing trimethylolpropane triacrylate for 3 to 32 weeks. All six had positive reactions to skin patch tests with 0.1% or 0.5% trimethylolpropane triacrylate in acetone.

For more Human Toxicity Excerpts (Complete) data for Trimethylolpropane triacrylate (6 total), please visit the HSDB record page.

Trimethylolpropane triacrylate's production and use as a multifunctional monomer, cross-linking agent, reactive diluent, and chemical intermediate and use in producing inks, coatings, varnishes, paints and resins(1) may result in its release to the environment through various waste streams(SRC).

AEROBIC: Trimethylolpropane triacrylate, present at 100 mg/L, reached 19% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(1); however, total degradation of trimethylolpropane triacrylate was 87% over the 4-week period with the formation of the diacrylate and monoacrylate esters plus trimethylolpropane(1).

Trimethylolpropane triacrylate, technical grade

Group 2B: Possibly carcinogenic to humans

Volume 122: (2019) Isobutyl Nitrite, β-Picoline, and Some Acrylates

2019

2018

Trimethylolpropane Triacrylate

An estimated BCF of 30 was calculated in fish for trimethylolpropane triacrylate(SRC), using a log Kow of 2.75(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(SRC). Based on exposure periods of 6 or 8 weeks in flow-through tests, the bioconcentration potential of trimethylolpropane triacrylate in carp has been classified as low (actual BCF values not reported)(4).

The Henry's Law constant for trimethylolpropane triacrylate is estimated as 6X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that trimethylolpropane triacrylate is expected to be essentially nonvolatile from water surfaces(2). Trimethylolpropane triacrylate's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Trimethylolpropane triacrylate's estimated vapor pressure of 5.9X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(1), suggests that volatilize from dry soil surfaces will not be important fate process(SRC); however, trimethylolpropane triacrylate is a liquid with a noticeable acrylic odor(3) suggesting some volatilization may occur(SRC).

/LABORATORY ANIMALS: Acute Exposure/ Eye irritation was scored 9 on a 10-grade scale 24 hours after application of trimethylolpropane triacrylate. By a Draize test, instillation of trimethylolpropane triacrylate into rabbit eyes induced irritation and reversible corneal opacity for 7 days.

/LABORATORY ANIMALS: Acute Exposure/ The NTP conducted a contact hypersensitivity study in conjunction with a subchronic study of technical grade trimethylolpropane triacrylate. It was not shown to be a skin sensitizer in female BALB/c mice. Although there was a significant trend toward increased responses at doses of 0.05%, 0.1%, and 0.25% in the murine local lymph node assay (LLNA), no individual dose was significantly different from the vehicle control and the highest response did not reach the threefold stimulation index suggested for a positive in the LLNA. Trimethylolpropane triacrylate was negative in a mouse ear swelling test. In the same study, trimethylolpropane triacrylate was positive in the murine irritancy assay at concentrations of 0.05%, 0.25%, and 0.5% when applied directly to the skin.

/LABORATORY ANIMALS: Acute Exposure/ /Investigators/ immunized outbred male and female Hartley guinea pigs (number not specified) with subcutaneous injection into the footpad and the nape of the neck with 0.1 mL of an emulsion containing trimethylolpropane triacrylate in ethanol:saline (1:4) in FCA. The total trimethylolpropane triacrylate dose was 11.5 umol. Skin tests of 0.02 mL of 0.25% or 0.5% trimethylolpropane triacrylate in acetone:olive oil (4:1) were then applied to the shaved flank of the guinea pig, and reactions were recorded at 24, 48, 72, and 96 hours. Skin reactions were graded on a scale of 0 (no reaction) to 3 (severe reaction). On day 7, the reactions for both concentrations were mild at 24 hours and moderate at 48 hours; the 24- and 48-hour reactions on day 14 were moderate.

/LABORATORY ANIMALS: Acute Exposure/ In a maximization test of acrylates and methacrylate esters, outbred female SSc:AL guinea pigs were induced with three 2 x 50 uL intradermal injections, including one of FCA in sterile water and one each of a test compound (methyl methacrylate, ethyleneglycol dimethacrylate, triethyleneglycol dimethacrylate, or trimethylolpropane trimethylacrylate) in soybean oil and in a mixture of emulsified FCA and water. On day 7, approximately 250 mg of 10% sodium lauryl sulfate in petrolatum was applied to the neck and left uncovered for 24 hours. On day 8, the test compound or petrolatum (400 uL) was applied to a filter paper patch that was applied to the flank and left in place for 48 hours. On day 21, the guinea pigs were challenged with up to six patches containing 25 uL of the sensitizing compound: 2-hydroxy-methacrylate, 1,6-hexane diolodiacrylate, pentaerythritol triacrylate, or trimethylolpropane triacrylate. Sensitization determinations were made at 48 and 72 hours. The treatment was repeated on the opposite flank of each animal after 35 days. Positive skin sensitization reactions occurred in 14 of 19 guinea pigs induced with trimethylolpropane trimethylacrylate and challenged with 2% trimethylolpropane triacrylate; animals induced with the other test chemicals did not have cross reactions with trimethylolpropane triacrylate.

For more Non-Human Toxicity Excerpts (Complete) data for Trimethylolpropane triacrylate (22 total), please visit the HSDB record page.

The rate constant for the vapor-phase reaction of trimethylolpropane triacrylate with photochemically-produced hydroxyl radicals has been estimated as 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 11 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of trimethylolpropane triacrylate with ozone has been estimated as 5.25X10-18 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1) which corresponds to an atmospheric half-life of about 2 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 0.0242 L/mole-sec at 25 °C(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 9 years and 331 days at pH values of 7 and 8, respectively(SRC). Trimethylolpropane triacrylate is reported to be light sensitive and may undergo spontaneous polymerization when exposed to direct sunlight(3); therefore, photodegradation may have some importance in the environment(SRC).

In male B6C3F1 mice, 75% of the dose was absorbed 72 hours after a single application of 1.2 mg/kg. The percent dose remaining at the dose site was higher in mice (31%) than in rats (9%). Approximately 42% of the applied dose was recovered in urine, feces, and exhaled carbon dioxide 72 hours after application, an amount similar to that excreted by rats (45%) following dermal application of 1.7 mg/kg. The radioactivity associated with tissues at 72 hours was less than 1%. The nonapplication site skin had an elevated tissue:blood ratio.

Metabolism and disposition of (14)C-trimethylolpropane triacrylate was investigated in male F344/N rats and B6C3F1 mice following single intravenous administration and dermal application (protected from oral grooming). In male rats, the percent dose absorbed was 55.7%, 32.7%, or 18.7% at 72 hours following dermal application of 1.7, 15.2, or 130 mg/kg. In mass terms, approximately five times more trimethylolpropane triacrylate was absorbed as the dose concentration increased by one order of magnitude. About 9% of the dose was recovered from the dose site regardless of the applied dose. About 45%, 19%, or 5% of the applied dose was recovered in the excreta 72 hours after dermal application of 1.7, 15.2, or 130 mg/kg, respectively. The radioactivity associated with tissues at 72 hours was less than 1%. The kidney had elevated tissue:blood ratios at each dose. Following intravenous administration of 9.4 mg/kg (14)C-trimethylolpropane triacrylate in male rats, a total of 77.4% of the applied dose was excreted in urine, feces, and exhaled carbon dioxide 72 hours after administration. Among the tissues collected, the highest radiolabeled concentration was associated with blood.

After a single 124 mg/kg dermal application of (14)C-trimethylolpropane triacrylate in male rats followed by tape stripping the application site at 72 hours, most of the radioactivity associated with the dose site was trimethylolpropane triacrylate thereby confirming that the test article was stable on the skin.

Used in the chemical industry for synthesis and in the paints, lacquers, and varnishes industry; [IUCLID] Uses based on cross-linking in radiation curing: Making inks and coatings (wood, paper, glass, metal, textiles, vinyl, and other plastics), in coatings, print varnishes, inks, other polymer systems, and in colloidal dispersions for industrial baked goods; Non-radiation curing uses: Paper and wood impregnates, rubber cross-linking, wire and cable extrusion, and anaerobic adhesives; Also used as a chemical intermediate; Present in many consumer products; [NTP]

Pulp and Paper Processing [Category: Industry]

Used in the production of ultraviolet-curable inks, electron beam irradiation-curable coatings, and polymers and resins; as a component of photopolymer and flexographic printing plates and photoresists; and as an ingredient in acrylic glues and anaerobic sealants. Also used in paper and wood impregnates, wire and cable extrusion, polymer-impregnated concrete, and polymer concrete structural composites.

Trimethylolpropane triacrylate is a multifunctional monomer with a wide range of industrial applications as a cross-linking agent, reactive diluent, and chemical intermediate. It is used in the production of ultraviolet-curable inks, electron beam irradiation-curable coatings, thermal paper, plastic hardener, optical fibers, UV-cured acrylate varnishes in the furniture industry, and polymers and resins; as a component of photopolymer and flexographic printing plates and photoresists; and as an ingredient in acrylic glues, adhesives, and anaerobic sealants. It is incorporated in colloidal dispersions for industrial baked coatings, waterborne and solvent based alkyds, and vinyl/acrylic nonwoven binders. Additionally, trimethylolpropane triacrylate is used in paper and wood impregnates, wire and cable extrusion, polymer-impregnated concrete, polymer concrete structural composites, and production of superabsorbent polymers for baby diapers.

2023: 10,000,000 - <25,000,000 lb

2-Propenoic acid, 2-ethyl-2-[[(1-oxo-2-propenyl)oxy]methyl]-1,3-propanediyl ester is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).[EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program. 2-Propenoic acid, 2-ethyl-2-[

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#8042]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 2-Propenoic acid, 1,1'-[2-ethyl-2-[[(1-oxo-2-propen-1-yl)oxy]methyl]-1,3-propanediyl] ester. Aggregated National Production Volume: 10 to < 50 million lbs.[US EPA; Non-Confidential 2006 Inventory Update Reporting. National Chemical Information. 2-Propenoic acid, 1,1'-[2-ethyl-2-[

Primary Metal Manufacturing

2-Propenoic acid, 1,1'-[2-ethyl-2-[[(1-oxo-2-propen-1-yl)oxy]methyl]-1,3-propanediyl] ester: ACTIVE

Ethylenimine and propylenimine react with trifunctional acrylates, such as 2-ethyl-2-(hydroxymethyl)-1,3-propanediol triacrylate ... to produce trifunctional aziridines.