n-Propyl methacrylate

0.9022 at 68 °F (NTP, 1992) - Less dense than water; will float

0.9022 g/cu cm at 20 °C

Insoluble (<1 mg/ml at 70 °F) (NTP, 1992)

Miscible with ethyl alcohol, ethyl ether

Insoluble in water

286 °F at 760 mmHg (NTP, 1992)

141 °C

Methyl methacrylate, and in general the methacrylic esters, polymerize much less readily than the corresponding ordinary acrylates. Nonetheless, they are stabilized by adding hydroquinone or pyrogallol, particularly in the presence of metallic copper. /Methacrylates/

6.38 [mmHg]

6.38 mm Hg at 25 °C

Warning

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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

Propyl methacrylate: 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.

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

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: 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.

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

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.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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 a manner that results in no direct personal contact by personnel who handle, dispose of, or clean the clothing. Quality assurance procedures to confirm the efficacy of the cleaning procedures should be implemented prior to the decontaminated protective clothing being returned for reuse by the workers. Contaminated clothing (including shoes/socks) should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

... 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/

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter.

Suitable protective clothing and self-contained respiratory protective apparatus should be available for use of those who may have to rescue persons overcome by fumes. /Acrylic acid and derivatives/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 130(SRC), determined from a structure estimation method(2), indicates that n-propyl methacrylate is expected to have high mobility in soil(SRC). Volatilization of n-propyl methacrylate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.6X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). n-Propyl methacrylate is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 6.38 mm Hg at 25 °C(4). Biodegradation data were not available(SRC, 2010).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 130(SRC), determined from a structure estimation method(2), indicates that n-propyl methacrylate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 5.6X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 5.1 hours and 5.0 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 14(SRC), from an estimated log Kow of 2.26(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2010).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), n-propyl methacrylate, which has a vapor pressure of 6.38 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase n-propyl 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 18 hours(SRC), calculated from its rate constant of 2.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). n-Propyl methacrylate contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of n-propyl methacrylate can be estimated to be 130(SRC). According to a classification scheme(2), this estimated Koc value suggests that n-propyl methacrylate is expected to have high mobility in soil.

/OTHER TOXICITY INFORMATION/ Biologically, methacrylates resemble acrylates, except for lower reactivity and thus decreased toxicity. This is probably due to steric hindrance by its methyl group and in turn decreased rates of membrane transport and systemic translocation. /Methacrylic esters/

An estimated BCF of 14 was calculated for n-propyl methacrylate(SRC), using an estimated log Kow of 2.26(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).

The Henry's Law constant for n-propyl methacrylate is estimated as 5.6X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that n-propyl methacrylate is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 5.1 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 5.0 days(SRC). n-Propyl methacrylate's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). n-Propyl methacrylate is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 6.38 mm Hg(3).

/LABORATORY ANIMALS: Acute Exposure/ Methacrylic acid administered iv increased respiratory rate, decreased heart rate, and produced electrocardiogram changes in anesthetized dogs (breed not identified). 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.

/GENOTOXICITY/ Ames assay (preincubation) in S. typhimurium TA98, TA100, TA1535, and TA1537 with and without rat and hamster liver S-9: negative.

The rate constant for the vapor-phase reaction of n-propyl methacrylate with photochemically-produced hydroxyl radicals has been estimated as 2.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 18 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of n-propyl methacrylate with ozone has been estimated as 1.1X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.0 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). A base-catalyzed second-order hydrolysis rate constant of 2.7X10-3 L/mole-sec(SRC) was estimated using a structure estimation method(3); this corresponds to half-lives of 81 and 8.1 years at pH values of 7 and 8, respectively(3). n-Propyl methacrylate is expected to undergo hydrolysis in the environment due to the presence of functional groups that hydrolyze under environmental conditions(4). n-Propyl methacrylate contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Occupational exposure to n-propyl methacrylate may occur through inhalation and dermal contact with this compound at workplaces where n-propyl methacrylate is produced or used. The general population may be exposed to n-propyl methacrylate via dermal contact with products containing n-propyl methacrylate. (SRC)

n-Propyl methacrylate's production and use as a monomer for methacrylic polymers may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 6.38 mm Hg at 25 °C indicates n-propyl methacrylate will exist solely as a vapor in the atmosphere. Vapor-phase n-propyl methacrylate will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 18 hours. n-Propyl methacrylate contains chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight. If released to soil, n-propyl methacrylate is expected to have high mobility based upon an estimated Koc of 130. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 5.6X10-4 atm-cu m/mole. n-Propyl methacrylate may volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation data were not available. If released into water, n-propyl methacrylate is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 5.1 hours and 5.0 days, respectively. An estimated BCF of 14 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is expected to be an important environmental fate process since this compound contains functional groups that hydrolyze under environmental conditions. Occupational exposure to n-propyl methacrylate may occur through inhalation and dermal contact with this compound at workplaces where n-propyl methacrylate is produced or used. The general population may be exposed to n-propyl methacrylate via dermal contact with products containing n-propyl methacrylate. (SRC)

Acrylates and methacrylates are detoxified predominantly via conjugation with glutathione via the Michael addition reaction or glutathione-S-transferase. They are also likely to be hydrolyzed via carboxylesterases. The lower molecular weight esters are rapidly metabolized and eliminated, therefore, will not likely cause cumulative toxicity.

Methyl methacrylate and other short chain alkyl-methacrylate esters are initially hydrolyzed by non-specific carboxylesterases to methacrylic acid and the structurally corresponding alcohol in several tissues. Methacrylic acid and the corresponding alcohol are subsequently cleared predominantly via the liver (valine pathway and the TCA (tricarboxylic acid) cycle, respectively). The carboxylesterases are a group of non-specific enzymes that are widely distributed throughout the body and are known to show high activity within many tissues and organs, including the liver, blood, GI tract, nasal epithelium and skin ... Those organs and tissues that play an important role and/or contribute substantially to the primary metabolism of the short-chain, volatile, alkyl-methacrylate esters are the tissues at the primary point of exposure, namely the nasal epithelia and the skin, and systemically, the liver and blood. /Short chain alkyl-methacrylate esters/

Recent studies have confirmed that alkyl-methacrylate esters are rapidly hydrolyzed by ubiquitous carboxylesterases ... First pass (local) hydrolysis of the parent ester has been shown to be significant for all routes of exposure. For example, no parent ester can be measured systemically following skin exposure to EMA and larger esters, as the lower rate of absorption for these esters is within the metabolic capacity of the skin ... Parent ester will also be effectively hydrolyzed within the G.I. tract and within the tissues of the upper respiratory tract (particularly the olfactory tissue). Systemically absorbed parent ester will be effectively removed during the first pass through the liver ... resulting in their relatively rapid elimination from the body ... /Short chain alkyl-methacrylate esters/

Methacrylate esters can conjugate with glutathione (GSH) in vitro, although they show a low reactivity, since the addition of a nucleophile at the double bond is hindered by the alpha-methyl side-group ... Hence, ester hydrolysis is considered to be the major metabolic pathway for alkyl-methacrylate esters, with GSH conjugation only playing a minor role in their metabolism, and then possibly only when very high tissue concentrations are achieved. /Short chain alkyl-methacrylate esters/

For more Metabolism/Metabolites (Complete) data for n-Propyl methacrylate (6 total), please visit the HSDB record page.

Used as monomer for acrylic resins; [HSDB]

Plastic Composites Manufacturing [Category: Industry]

Monomer for methacrylic polymers /Methacrylic acid esters/

Monomer for acrylic resins.

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/

Esterification or transesterification of n-propyl alcohol with either methacrylic acid or methyl methacrylate

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

Alkyl mercury compounds have been used as seed disinfectants and for fungicides. They have also been used in organic synthesis. /Mercury alkyl compounds/

Methyl methacrylate, and in general the methacrylic esters, polymerize much less readily than the corresponding ordinary acrylates. Nonetheless, they are stabilized by adding hydroquinone or pyrogallol, particularly in the presence of metallic copper. /Methacrylates/