ChemicalBook > Product Catalog > Organic Chemistry > Carboxylic acids and derivatives > Carboxylic acid esters and derivatives > Ethyl acrylate
Ethyl acrylate Chemical Properties
- Melting point:−71 °C(lit.)
- Boiling point:99 °C(lit.)
- Density 0.921 g/mL at 20 °C
- vapor density 3.5 (vs air)
- vapor pressure 31 mm Hg ( 20 °C)
- refractive index n
- FEMA 2418 | ETHYL ACRYLATE
- Flash point:60 °F
- storage temp. Refrigerator
- solubility 20g/l
- form Liquid
- color Clear
- OdorCharacteristic acrylic odor; sharp, fragrant; acrid; slightly nauseating; sharp, ester type.
- Odor Threshold0.00026ppm
- explosive limit1.8-14%(V)
- Water Solubility 1.5 g/100 mL (25 ºC)
- FreezingPoint 99.8℃
- Merck 14,3759
- JECFA Number1351
- BRN 773866
- Henry's Law Constant2.25(x 10-3 atm?m3/mol) at 20 °C (approximate - calculated from water solubility and vapor pressure)
- Exposure limitsTLV-TWA 5 ppm (～20 mg/m3) (ACGIH), 25 ppm (～100 mg/m3 (MSHA, NIOSH), TWA skin 25 ppm (100 mg/m3) (OSHA); IDLH 2000 ppm (NIOSH).
- Stability:Stable, but may polymerize upon exposure to light. Highly flammable. Keep cool. Incompatible with oxidizing agents, peroxides and other polymerization initiators.
- CAS DataBase Reference140-88-5(CAS DataBase Reference)
- NIST Chemistry Reference2-Propenoic acid, ethyl ester(140-88-5)
- IARC2B (Vol. 39, Sup 7, 71, 122) 2019
- EPA Substance Registry SystemEthyl acrylate (140-88-5)
- Hazard Codes F,Xn
- Risk Statements 11-20/21/22-36/37/38-43
- Safety Statements 9-16-33-36/37
- RIDADR UN 1917 3/PG 2
- WGK Germany 2
- RTECS AT0700000
- F 8
- Autoignition Temperature721 °F
- TSCA Yes
- HS Code 2916 12 00
- HazardClass 3
- PackingGroup II
- Hazardous Substances Data140-88-5(Hazardous Substances Data)
- ToxicityLD50 orally in Rabbit: 550 mg/kg LD50 dermal Rabbit 1800 mg/kg
Ethyl acrylate Usage And Synthesis
- UsesA monomer widely used in the production of polymers and copolymers for manufacturing textiles, latex paints, paper coatings, dirt release agents, and specialty plastics
- DescriptionEthyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ethyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers . It is also a reagent in the synthesis of various pharmaceutical intermediates.
- Chemical PropertiesEthyl acrylate is a colorless liquid. Sharp, acrid odor. The Odor Threshold is 0.000240.0009 ppm
- Chemical PropertiesEthyl acrylate has a characteristic penetrating and persistent odor. Ethyl acrylate is possibly carcinogenic to humans (IARC, California Proposition 65)
- Physical propertiesClear, colorless liquid with a penetrating and pungent odor. Leonardos et al. (1969) and Nagata and Takeuchi (1990) reported odor threshold concentrations of 0.47 and 0.26 ppbv, respectively. Experimentally determined detection and recognition odor threshold concentrations were 1.0 μg/m3 (0.24 ppbv) and 1.5 μg/m3 (0.37 ppbv), respectively (Hellman and Small, 1974).
- OccurrenceReported found in pineapple, yellow passion fruit and durian (Durio zibethinus).
- UsesMonomer for acrylic resins.
- UsesEthyl acrylate is used in the manufacture ofacrylic resins, acrylic fibers, textile and papercoatings, adhesives, and leather finish resins;and as a flavoring agent.
- UsesEthyl Acrylate is a flavoring agent that is a clear, colorless liquid. its odor is fruity, harsh, penetrating, and lachrymatous (causes tears). it is sparingly soluble in water and miscible in alcohol and ether, and is obtained by chemical synthesis.
- PreparationBy esterification of acrylic acid; by heating acetylene with HCl in alcoholic solution in the presence of Ni(CO)4; also from ethyl-3-chloropropionate passed over activated carbon at high temperature.
- Production MethodsEthyl acrylate is manufactured via oxidation of propylene to
acrolein and then to acrylic acid. The acid is treated with
ethanol to yield the ethyl ester .
Vinyl chloride reacts at 270 °C at >6895 kPa (68 atm) with ethanol in the presence of a cobalt and palladium catalyst to give ethyl acrylate in a yield of 17% .
- Aroma threshold valuesDetection: 0.2 ppb
- General DescriptionA clear colorless liquid with an acrid odor. Flash point 60°F. May polymerize exothermically if heated or contaminated. If the polymerization takes place inside a container, the container may rupture violently. Auto ignition temperature 721°F (383°C) (NTP). Less dense than water. Vapors heavier than air. Used to make paints and plastics.
- Air & Water ReactionsHighly flammable. Insoluble in water.
- Reactivity ProfileA flammable liquid, confirmed carcinogen. Ethyl acrylate can react vigorously with oxidizing reagents, peroxides,strong alkalis and polymerization initiators. [NTP] Ethyl acrylate reacts violently with chlorosulfonic acid [Sax, 9th ed., 1996, p. 1515]. When an inhibited monomer was placed in a clear glass bottle exposed to sunlight, exothermic polymerization set in and caused the bottle to burst. The use of brown glass or metal containers and increase in inhibitor concentration (to 200 ppm; tenfold) was recommended [MCA Case History No. 1759]. Ethyl acrylate may polymerize when exposed to light and Ethyl acrylate is subject to slow hydrolysis. Inhibitors do not function in the absence of air. Solutions in DMSO are stable for 24 hours under normal lab conditions. [NTP].
- HazardToxic by ingestion, inhalation, skin absorption; irritant to skin and eyes. Flammable, dangerous fire and explosion hazard. Possible carcinogen.
- Health HazardEthyl acrylate is a strong irritant to the eyes,skin, and mucous membranes. The liquid orits concentrated solutions can produce skinsensitization upon contact. It is toxic by allroutes of exposure. The toxicity is low inrats and mice and moderate in rabbits. Thetoxic effects from inhalation noted in animalswere congestion of lungs and degenerativechanges in the heart, liver, and kidney. Mon key exposed to 272 ppm for 28 days showedlethargy and weight loss; while exposure to1024 ppm caused death to the animals after2.2 days (Treon et al. 1949). By compari son, guinea pigs died of exposure to about1200 ppm for 7 hours. Ingestion of the liq uid may result in irritation of gastrointestinaltracts, nausea, lethargy, and convulsions
The LD50 values varied significantly indifferent species of animals. The oral LD50values in rabbits, rats, and mice are in therange 400, 800, and 1800 mg/kg, respectively. Animals administered ethyl acrylateshowed increased incidence of tumors inforestomach. However, there is no evidenceof carcinogenicity caused by this compoundin humans.
- Chemical ReactivityReactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: May occur; exclude moisture, light; avoid exposure to high temperatures; store in presence of air; Inhibitor of Polymerization: 13-17 ppm monomethyl ether of hydroquinone.
- Safety ProfileConfirmed carcinogen with experimental carcinogenic data. Poison by ingestion and inhalation. Moderately toxic by skin contact and intraperitoneal routes. Human systemic effects by inhalation: eye, olfactory, and pulmonary changes. A skin and eye irritant. Characterized in its terminal stages by dyspnea, cyanosis, and convulsive movements. It caused severe local irritation of the gastroenteric tract; and toxic degenerative changes of cardiac, hepatic, renal, and splenic tissues were observed. It gave no evidence of cumulative effects. When applied to the intact skin of rabbits, the ethyl ester caused marked local irritation, erythema, edema, thickening, and vascular damage. Animals subjected to a fairly high concentration of these esters suffered irritation of the mucous membranes of the eyes, nose, and mouth as well as lethargy, dpspnea, and convulsive movements. A substance that migrates to food from packagmg materials. Flammable liquid. A very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. Violent reaction with chlorosulfonic acid. To fight fire, use CO2, dry chemical, or alcohol foam. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.
- SafetyIt is an acute toxin with an LD50 (rats, oral) of 1020 mg / kg and a TLV of 5 ppm. The International Agency for Research on Cancer stated, "Overall evaluation, Ethyl acrylate is possibly carcinogenic to humans (Group 2B)." The United States Environmental Protection Agency (EPA) states, "Human studies on occupational exposure to ethyl acrylate... have suggested a relationship between exposure to the chemical(s) and colorectal cancer, but the evidence is conflicting and inconclusive. In a study by the National Toxicology Program (NTP), increased incidences of squamous cell papillomas and carcinomas of the fore stomach were observed in rats and mice exposed via gavage (experimentally placing the chemical in the stomach). However, the NTP recently determined that these data were not relevant to human carcinogenicity since humans do not have a fore stomach, and removed ethyl acrylate from its list of carcinogens." (Occupational exposure generally involves exposure that occurs regularly, over an extended period of time.)
One favorable safety aspect is that ethyl acrylate has good warning properties; the odor threshold is much lower than any level of health concern. In other words, the bad odor warns people of ethyl acrylate's presence long before the concentration reaches a level capable of creating a serious health risk.
- Potential ExposureThis material is used in emulsion polymers for paints, textiles, adhesives, coatings and binders; as a monomer in the manufacture of homopolymer and copolymer resins for the production of paints and plastic films
- CarcinogenicityA retrospective study found
an excess of colorectal cancers in one exposed population of
workers; however, the data were confounded by other exposures
and lack of association of causality and risk in similarly
exposed populations from other locations. Therefore, there
was inadequate evidence based on the study that ethyl acrylate
is a human carcinogen . Ethyl acrylate is listed as
USEPA group B2, “Probable human carcinogen”; IARC
group B2, “Possibly carcinogenic in humans”; NIOSH,
“Carcinogen with no further categorization”; NTP group 2,
“Reasonably anticipated to be a carcinogen” and listed as a
carcinogen by California Proposition 65 .
Dermal studies of acrylic acid, ethyl acrylate, and n-butyl acrylate using mice did not result in local carcinogenesis, but several mice in the ethyl acrylate-treated group did exhibit dermatitis, dermal fibrosis, epidermal necrosis, and hyperkeratosis .
- Environmental FateChemical/Physical. Polymerizes on standing and is catalyzed by heat, light, and peroxides
(Windholz et al., 1983). Slowly hydrolyzes in water forming ethanol and acrylic acid. The
reported rate constant for the reaction of ethyl acrylate with ozone in the gas phase was determined
to be 5.70 x 10-18 cm3 mol/sec (Munshi et al., 1989).
At an influent concentration of 1,015 mg/L, treatment with GAC resulted in an effluent concentration of 226 mg/L. The adsorbability of the carbon used was 157 mg/g carbon (Guisti et al., 1974).
- ShippingUN1917 Ethyl acrylate, Hazard Class: 3; Labels: 3-Flammable liquid
- Purification MethodsWash the ester repeatedly with aqueous NaOH until free from inhibitors such as hydroquinone, then wash it with saturated aqueous CaCl2 and distil it under reduced pressure. Hydroquinone should be added if the ethyl acrylate is to be stored for extended periods. [Beilstein 2 IV 1460.] LACHRYMATORY.
- IncompatibilitiesMay form explosive mixture with air. Atmospheric moisture and strong alkalies may cause fire and explosions unless properly inhibited (Note: Inert gas blanket not recommended). Heat, light or peroxides can cause polymerization. Incompatible with oxidizers (may be violent), peroxides, polymerizers, strong alkalis; moisture, chlorosulfonic acid, strong acids; amines. May accumulate static electrical charges, and may cause ignition of its vapors. Polymerizes readily unless an inhibitor, such as hydroquinone is added. Uninhibited vapors may plug vents by the formation of polymers.
- Waste DisposalIncineration or by absorption and landfill disposal
Ethyl acrylate Preparation Products And Raw materials
- Preparation ProductsCarbomer 940EnalaprilEthyl 5-[3-(4,6-dimethoxy pyrimidyl-2-yl)ureido]methylpyrazolyl-4-carboxylic esterStyrene-acrylic latexETHYL 2-(BROMOMETHYL)ACRYLATECiprofloxacin hydrochlorideETHYL 4-PIPERIDONE-3-CARBOXYLATE HYDROCHLORIDE1-BENZYL-3-METHYL-4-PIPERIDONE2,3,4,5-Tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one5,6-DIHYDRO-4-(2-METHYL-2-PHENYLHYDRAZINO)-2-1H-PYRIDINONE4-Piperidinonecarfentrazone-ethylacrylic resin coating finish2,4-Piperadinedione3-AMINO-PROPIONIC ACID ETHYL ESTERimpregnanting agent for leatherThickening agentEthyl 3-(benzylamino)propanoate3-ISOPROPYLAMINO-PROPIONIC ACID ETHYL ESTER X HCL >98%Adhesive for electrostatic flockingLeather coating agent of filling acrylic resinVinyl acetate-acrylate copolymer,emulsionEthyl 3-methylthiopropionate
- Raw materialsEtanolSULFURIC ACIDAcrylonitrileCARBON MONOXIDEAcrylic acidCarbomer 940AcrylamideAcrolein2-OxetanoneETHYLENE3-HydroxypropionitrileAmmonium hydrogen sulfateSelf-interlinkage adhesive TEthyl 3-chloropropionateNICKEL CARBONYL
- Ethyl acrylate Ethyl acetate Ethylparaben Trinexapac-ethyl 2-Hydroxyethyl acrylate 2-Hydroxyethyl methacrylate Ethyl 3-benzoylacrylate ETHYL 2-CYANOACRYLATE URETHANE ACRYLATE 2-Ethoxyethanol ISOXADIFEN-ETHYL Butyl acrylate Ethanol Acrylic acid Ethyl 3-ethoxyacrylate Methyl methacrylate Ethyl methacrylate Ethyl 2-(hydroxymethyl)acrylate
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