Diethylaminoethyl methacrylate

185.26

185.26

203-275-7

N5SI2E7HOU

14490

1993

DTXSID4026713

Clear, colorless liquid

2922199090

29.5

1.9

Diethylaminoethylmethacrylate, [liquid] appears as a clear light colored liquid. Insoluble in water and slightly denser than water. May be toxic by ingestion. Contact may severely irritate skin.

0.98 g/cm³ @ Temp: 20 °C

-60°C

49 °C @ Press: 0.30 Torr

81.0±13.5 °C

1.449

In water, 21,900 mg/L at 25 deg C (est)

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. Temperatures must be kept low to minimize formation of peroxides and other products. Moisture may cause rust-initiated polymerization. /Acrylic acid & derivatives/

0.11 mm Hg at 25 deg C (est)

Henry's Law constant: 2.1X10-7 atm cu m/mol at 25 °C /est/

pKa = 8.96 at 25 °C (est)

Most aliphatic amines have an unpleasant, fishy or fishlike odor and in high concentrations they all have the odor of ammonia. /Aliphatic amines/|Hydroxyl radical reaction rate constant: 1.1X10-10 cu cm/molecule-sec at 25 °C (est)

Flammable. Insoluble in water.

Amines, Phosphines, and Pyridines

Polymerizable

An acrylic acid ester/amine. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

NA 1993 / PGIII

1

R20;R36/38;R43

S26

OZ4150000

Xn:Harmful;

Stable under recommended storage conditions. Contains the following stabiliser(s): Mequinol (*** ppm)

P280-P305 + P351 + P338

H315-H317-H319-H332

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.

Incompatible materials: Steel (all types and surface treatments), Strong oxidizing agents, Copper, Carbon dioxide (CO2)

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. Substance may be transported hot. For hybrid vehicles, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. If molten aluminum is involved, refer to ERG Guide 169. (ERG, 2016)

|Warning|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P280, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, and P501|H302 (16.42%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, and P501|Aggregated GHS information provided by 530 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H227: Combustible liquid [Warning Flammable liquids]|P210, P261, P264, P271, P272, P280, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P403+P235, and P501|Danger|P201, P202, P210, P260, P261, P264, P271, P280, P281, P301+P330+P331, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P363, P370+P378, P403+P235, P405, and P501|P201, P202, P210, P260, P261, P264, P270, P271, P272, P280, P281, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P308+P313, P309+P311, P310, P312, P321, P330, P333+P313, P363, P370+P378, P403+P235, P405, and P501

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|Body Protection: Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Skin protection: Handle with gloves.|Eye/face protection: Face shield and safety glasses Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|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/

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

ACCIDENTAL RELEASE MEASURES. Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Beware of vapours accumulating to form explosive concentrations. Vapours can accumulate in low areas.; Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains.; 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.

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.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapour or mist. Keep away from sources of ignition - No smoking.Take measures to prevent the build up of electrostatic charge.|... 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.

The lower molecular weight esters of acrylic acids are irritants to skin, eyes and mucous membranes. /Acrylic acid esters/

IDENTIFICATION AND USE: 2-(N,N-Diethylamino)ethyl methacrylate is a clear, colorless liquid. It is used as a pH-responsive component in the formation of nanocarriers. HUMAN EXPOSURE AND TOXICITY: No human studies available. ANIMAL STUDIES: 2-(N,N-diethylamino)ethyl methacrylate, in acute studies with rabbits, initially suppressed brain electrical activity and then induced clonic-tonic spasms. It was strongly irritating to skin of guinea pigs and conjunctiva of rabbits. Animal studies using rats revealed that some acrylates and methacrylates are embryotoxic. The doses of monomers used in the animal studies, however, were much higher than concentrations likely encountered by workers. This chemical did not induce gene mutations in S. typhimurium and E. coli strains. Toxicity was observed at 5000 ug/plate (TA100, TA1535, TA98, TA1537) without an S9 mix and at 2500 ug/plate (five strains) with an S9 mix. Toxicity was not observed at 5000 ug/plate in WP2 uvrA without an S9 mix. In a chromosome aberration test using Chinese hamster lung cells, structural chromosomal aberrations were induced at 0.30 and 0.60 mg/mL in the presence of an exogenous metabolic activation system.

LD50 Rat oral 4696 mg/kg

2-(N,N-Diethylamino)ethyl methacrylate's production and use as an intermediate for chemical synthesis and as a monomer in the production of a variety of copolymers and homopolymers(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 71(SRC), determined from a structure estimation method(2), indicates that 2-(N,N-diethylamino)ethyl methacrylate is expected to have high mobility in soil(SRC). The pKa of 2-(N,N-diethylamino)ethyl methacrylate is estimated to be 8.96(3), indicating that this compound will exist mostly in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of 2-(N,N-diethylamino)ethyl methacrylate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.1X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(2). 2-(N,N-Diethylamino)ethyl methacrylate may volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.11 mm Hg(SRC), determined from a fragment constant method(2). Utilizing the Japanese MITI test, 70% of the Theoretical BOD was reached in 4 weeks(6) suggesting that biodegradation is an important environmental fate process in soil(SRC). Based on the Japanese MITI test(6) and analog to the similar 2-(N,N-dimethylamino)ethyl methacrylate(7), 2-(N,N-diethylamino)ethyl methacrylate may degrade via abiotic hydrolysis in moist alkaline and neutral soils(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 71(SRC), determined from a structure estimation method(2), indicates that 2-(N,N-diethylamino)ethyl methacrylate 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 2.1X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 9(SRC), from an estimated log Kow of 1.95(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 70% of the Theoretical BOD was reached in 4 weeks(5) suggesting that biodegradation is an important environmental fate process in water(SRC). The analogous compound 2-(N,N-dimethylamino)ethyl methacrylate is hydrolyzed at pH 7 and at pH 9 with half-lives of 4.54 days and 3.31 hours, respectively (at 25 °C), whereas it is stable at pH 4(6); 2-(N,N-diethylamino)ethyl methacrylate is expected to have very similar hydrolysis rates(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-(N,N-diethylamino)ethyl methacrylate, which has an estimated vapor pressure of 0.11 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-(N,N-diethylamino)ethyl 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 3.4 hours(SRC), calculated from its rate constant of 1.1X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Vapor-phase 2-(N,N-diethylamino)ethyl methacrylate is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 24 hours(SRC), calculated from its rate constant of 1.1X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Based on analogy to a measured nitrate radical rate constant of 4.90X10-15 cu cm/molecule-sec at 25 °C for ethyl methacrylate(3), the atmospheric half-life of 2-(N,N-diethylamino)ethyl methacrylate is estimated to be about 6.5 days(SRC).

The rate constant for the vapor-phase reaction of 2-(N,N-diethylamino)ethyl methacrylate with photochemically-produced hydroxyl radicals has been estimated as 1.1X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3.4 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of 2-(N,N-diethylamino)ethyl 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 24 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(1). Based on analogy to a measured nitrate radical rate constant of 4.90X10-15 cu cm/molecule-sec at 25 °C for ethyl methacrylate(2), the atmospheric half-life of 2-(N,N-diethylamino)ethyl methacrylate is estimated to be about 6.5 days(SRC) at an atmospheric concentration of 2.5X10+8 nitrate radicals per cu cm(3). 2-(N,N-Diethylamino)ethyl methacrylate is an olefin and olefins in surface waters exposed to sunlight react with photo-oxidants (such as hydroxyl radicals, peroxy radicals and singlet oxygen) with a half-life on the order of 25 days(4). The analogous compound 2-(N,N-dimethylamino)ethyl methacrylate is hydrolyzed at pH 7 and at pH 9 (25 °C) with half-lives of 4.54 days and 3.31 hours, respectively, whereas it is stable at pH 4(5); 2-(N,N-diethylamino)ethyl methacrylate is expected to have very similar hydrolysis rates(SRC).

An estimated BCF of 9 was calculated in fish for 2-(N,N-diethylamino)ethyl methacrylate(SRC), using an estimated log Kow of 1.95(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2-(N,N-diethylamino)ethyl methacrylate can be estimated to be 71(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-(N,N-diethylamino)ethyl methacrylate is expected to have high mobility in soil. The estimated pKa of 2-(N,N-diethylamino)ethyl methacrylate is 8.96(3), indicating that this compound will exist mostly in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

The Henry's Law constant for 2-(N,N-diethylamino)ethyl methacrylate is estimated as 2.1X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-(N,N-diethylamino)ethyl methacrylate is expected to be essentially nonvolatile from water surfaces(2). 2-(N,N-Diethylamino)ethyl methacrylate's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). 2-(N,N-Diethylamino)ethyl methacrylate may volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.11 mm Hg(SRC), determined from a fragment constant method(1).

According to the 2012 TSCA Inventory Update Reporting data, 1 reporting facilities estimate the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of 2-(N,N-diethylamino)ethyl methacrylate (CAS 105-16-8) is reported as 100-499 workers; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|Occupational exposure to 2-(N,N-diethylamino)ethyl methacrylate may occur through inhalation and dermal contact with this compound at workplaces where 2-(N,N-diethylamino)ethyl methacrylate is produced or used(SRC). Based on analogy to the very similar 2-(N,N-dimethylamino)ethyl methacrylate(1), the general population may be exposed to 2-(N,N-diethylamino)ethyl methacrylate via dermal contact with consumer products containing polymers made with the compound and resulting migration of residual monomer from the polymer matrix(SRC).

Small quantities of methacrylates may readily be metabolized by saponification into the alcohol and methacrylic acid. The latter may form an acetyl-coenzyme A derivative, which then enters the normal lipid metabolism. /Methacrylates/|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. /Methacrylates/

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. (ERG, 2016)

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Wash skin with soap and water. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Keep victim calm and warm. (ERG, 2016)

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Esters and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilation if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Esters and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Esters and related compounds/

2-(diethylamino)ethyl methacrylate

Construction|2-Propenoic acid, 2-methyl-, 2-(diethylamino)ethyl ester: ACTIVE|2-Propenoic acid, 2-methyl-, 2-(diethylamino)ethyl ester, homopolymer: ACTIVE|XU - indicates a substance exempt from reporting under the Chemical Data Reporting Rule, (40 CFR 711).|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/

Thin-layer chromatography (TLC), polarography, and spectrometry are used for solution measurements. Methacrylates in air have been analyzed by TLC, polarography, and colorimetry. Polarography has been used for determination of any residual monomer in the polymer. A variety of spectroscopic techniques, e.g., NMR, IR, and Raman spectroscopy also have been used, particularly for analysis of surgical cements and dental restorative resins. /Methacrylic acid and derivatives/