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140-88-5

140-88-5 Structure

140-88-5 Structure
IdentificationMore
[Name]

Ethyl acrylate
[CAS]

140-88-5
[Synonyms]

2-PROPENOIC ACID ETHYL ESTER
ACRYLIC ACID ETHYL ESTER
EA
ETHYL 2-PROPENOATE
ETHYL ACRYLATE
FEMA 2418
RARECHEM AL BI 0670
Acrylate d'ethyle
acrylated’ethyle
acrylated’ethyle(french)
Acrylic acid, ethyl ester (inhibited)
Akrylanem etylu
akrylanemetylu
Carboset 511
carboset511
CH2=CHCOOC2H5
Ethoxycarbonylethylene
Ethyl acrylate, inhibited
Ethyl ester of 2-propenoic acid
Ethyl propenoate
[EINECS(EC#)]

205-438-8
[Molecular Formula]

C5H8O2
[MDL Number]

MFCD00009188
[Molecular Weight]

100.12
[MOL File]

140-88-5.mol
Chemical PropertiesBack Directory
[Appearance]

colourless liquid
[Appearance]

Ethyl acrylate is a colorless liquid. Sharp, acrid odor. The Odor Threshold is 0.000240.0009 ppm
[Melting point ]

−71 °C(lit.)
[mp ]

−71 °C(lit.)
[Boiling point ]

99 °C(lit.)
[bp ]

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 ]

n20/D 1.406(lit.)
[FEMA ]

2418
[Fp ]

60 °F
[storage temp. ]

Refrigerator
[solubility ]

20g/l
[form ]

Liquid
[color ]

Clear
[Odor]

Characteristic acrylic odor; sharp, fragrant; acrid; slightly nauseating; sharp, ester type.
[Stability:]

Stable, but may polymerize upon exposure to light. Highly flammable. Keep cool. Incompatible with oxidizing agents, peroxides and other polymerization initiators.
[explosive limit]

1.8-14%(V)
[Odor Threshold]

0.00026ppm
[Water Solubility ]

1.5 g/100 mL (25 ºC)
[FreezingPoint ]

99.8℃
[JECFA Number]

1351
[Merck ]

14,3759
[BRN ]

773866
[Henry's Law Constant]

2.25(x 10-3 atm?m3/mol) at 20 °C (approximate - calculated from water solubility and vapor pressure)
[Exposure limits]

TLV-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).
[Uses]

Monomer for acrylic resins.
[Uses]

Ethyl 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.
[CAS DataBase Reference]

140-88-5(CAS DataBase Reference)
[NIST Chemistry Reference]

2-Propenoic acid, ethyl ester(140-88-5)
[IARC]

2B (Vol. 39, Sup 7, 71, 122) 2019
[EPA Substance Registry System]

140-88-5(EPA Substance)
Questions And AnswerBack Directory
[Uses]

A monomer widely used in the production of polymers and copolymers for manufacturing textiles, latex paints, paper coatings, dirt release agents, and specialty plastics
Safety DataBack Directory
[Hazard Codes ]

F,Xn
[Risk Statements ]

R11:Highly Flammable.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
R43:May cause sensitization by skin contact.
[Safety Statements ]

S9:Keep container in a well-ventilated place .
S16:Keep away from sources of ignition-No smoking .
S33:Take precautionary measures against static discharges .
S36/37:Wear suitable protective clothing and gloves .
[RIDADR ]

UN 1917 3/PG 2
[WGK Germany ]

2
[RTECS ]

AT0700000
[F ]

8
[Autoignition Temperature]

721 °F
[TSCA ]

Yes
[HazardClass ]

3
[PackingGroup ]

II
[HS Code ]

29161220
[Safety Profile]

Confirmed 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.
[Hazardous Substances Data]

140-88-5(Hazardous Substances Data)
[Toxicity]

LD50 orally in Rabbit: 550 mg/kg LD50 dermal Rabbit 1800 mg/kg
Raw materials And Preparation ProductsBack Directory
【Raw materials】

Ethanol-->FUMING SULFURIC ACID-->Acrylonitrile-->CARBON MONOXIDE-->Acrylic acid-->Poly(acrylic acid)-->Acrylamide-->Acrolein-->2-Oxetanone-->ETHYLENE-->3-Hydroxypropionitrile-->Ammonium hydrogen sulfate-->Self-interlinkage adhesive T-->Ethyl 3-chloropropionate-->NICKEL CARBONYL
【Preparation Products】

Poly(acrylic acid)-->Enalapril-->Ethyl 5-[3-(4,6-dimethoxy pyrimidyl-2-yl)ureido]methylpyrazolyl-4-carboxylic ester-->Styrene-acrylic latex-->ETHYL 2-(BROMOMETHYL)ACRYLATE-->Ciprofloxacin hydrochloride-->ETHYL 4-PIPERIDONE-3-CARBOXYLATE HYDROCHLORIDE-->1-BENZYL-3-METHYL-4-PIPERIDONE-->2,3,4,5-Tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one-->5,6-DIHYDRO-4-(2-METHYL-2-PHENYLHYDRAZINO)-2-1H-PYRIDINONE-->4-Piperidinone-->carfentrazone-ethyl-->acrylic resin coating finish-->2,4-Piperadinedione-->3-AMINO-PROPIONIC ACID ETHYL ESTER-->impregnanting agent for leather-->Thickening agent-->Ethyl 3-(benzylamino)propanoate-->3-ISOPROPYLAMINO-PROPIONIC ACID ETHYL ESTER X HCL >98%-->Adhesive for electrostatic flocking-->Leather coating agent of filling acrylic resin-->Vinyl acetate-acrylate copolymer,emulsion-->Ethyl 3-methylthiopropionate
Hazard InformationBack Directory
[General Description]

A 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.
[Reactivity Profile]

A flammable liquid, confirmed carcinogen. ETHYL ACRYLATE, INHIBITED(140-88-5) can react vigorously with oxidizing reagents, peroxides,strong alkalis and polymerization initiators. [NTP] ETHYL ACRYLATE, INHIBITED(140-88-5) 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, INHIBITED(140-88-5) may polymerize when exposed to light and ETHYL ACRYLATE, INHIBITED(140-88-5) 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].
[Air & Water Reactions]

Highly flammable. Insoluble in water.
[Hazard]

Toxic by ingestion, inhalation, skin absorption; irritant to skin and eyes. Flammable, dangerous fire and explosion hazard. Possible carcinogen.
[Health Hazard]

May cause irritation and burns of eyes and skin. Exposure to excessive vapor concentrations can also cause drowsiness accompanied by nausea, headache, or extreme irritation of the respiratory tract.
[Potential Exposure]

This 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
[First aid]

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. Medical observation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy.
[Shipping]

UN1917 Ethyl acrylate, Hazard Class: 3; Labels: 3-Flammable liquid
[Incompatibilities]

May 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.
[Description]

Ethyl 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.
[Waste Disposal]

Incineration or by absorption and landfill disposal
[Chemical Properties]

Ethyl acrylate has a characteristic penetrating and persistent odor. Ethyl acrylate is possibly carcinogenic to humans (IARC, California Proposition 65)
[Chemical Properties]

Ethyl acrylate is a colorless liquid. Sharp, acrid odor. The Odor Threshold is 0.000240.0009 ppm
[Physical properties]

Clear, 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).
[Occurrence]

Reported found in pineapple, yellow passion fruit and durian (Durio zibethinus).
[Preparation]

By 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 Methods]

Ethyl 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 values]

Detection: 0.2 ppb
[Chemical Reactivity]

Reactivity 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]

It 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.
[Carcinogenicity]

A 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 Fate]

Chemical/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).
[Purification Methods]

Wash 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.
[Toxicity evaluation]

The toxic mode of action for ethyl acrylate is unknown. However, the parent compound may play a significant role since pretreatment of rats with a carboxylesterase inhibitor enhances the respiratory irritation and lethality produced by the inhalation of ethyl acrylate. The enhanced toxicity could be a direct effect of methyl acrylate on surrounding tissues and/or a secondary effect due to the increased conjugation of methyl acrylate with glutathione that occurs under these conditions which in turn can result in toxicity due to the depletion of local glutathione stores.
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

ethyl acrylate(140-88-5).msds
Spectrum DetailBack Directory
[Spectrum Detail]

Ethyl acrylate(140-88-5) 13C NMR
Ethyl acrylate(140-88-5) IR1
Ethyl acrylate(140-88-5) 1H NMR
Ethyl acrylate(140-88-5) Raman
Ethyl acrylate(140-88-5) MS
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Ethyl acrylate, stabilized, 99.50%(140-88-5)
[Alfa Aesar]

Ethyl acrylate, 99%, stab. with ca 20ppm 4-methoxyphenol(140-88-5)
[Sigma Aldrich]

140-88-5(sigmaaldrich)
[TCI AMERICA]

Ethyl Acrylate  (stabilized with MEHQ),>99.0%(GC)(140-88-5)
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