| Identification | More | [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 Properties | Back Directory | [Appearance]
Ethyl acrylate is a colorless liquid. Sharp,
acrid odor. The Odor Threshold is 0.000240.0009 ppm | [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)
| [FEMA ]
2418 | [refractive index ]
n20/D 1.406(lit.)
| [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 | [Odor Type]
plastic | [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). | [LogP]
1.18 at 25℃ | [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) | [IARC]
2B (Vol. 39, Sup 7, 71, 122) 2019 | [NIST Chemistry Reference]
2-Propenoic acid, ethyl ester(140-88-5) | [EPA Substance Registry System]
140-88-5(EPA Substance) |
| Questions And Answer | Back 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 Data | Back 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 | [IDLA]
300 ppm |
| Hazard Information | Back 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. | [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 | [Waste Disposal]
Incineration or by absorption and landfill disposal | [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). | [Definition]
ChEBI: Ethyl acrylate is an enoate ester. | [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
| [Flammability and Explosibility]
Flammable | [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). | [storage]
Color Code—Red: Flammability Hazard: Store ina flammable liquid storage area or approved cabinet awayfrom ignition sources and corrosive and reactive materials.Ethyl acrylate must be stored to avoid contact with oxidizers (such as peroxides, perchlorates, chlorates, nitrates, andpermanganates), strong alkalis (such as sodium hydroxideand potassium hydroxide) and moisture since violent reactions occur. Store in tightly closed containers in a cool,well-ventilated area away from heat. Heat can cause ethylacrylate to react by itself. If this takes place in a closed container, an explosion could occur. Ethyl acrylate usually contains an inhibitor, such as hydroquinone or its methyl ether,to prevent a self-reaction. If it does not contain an inhibitor,the reaction may occur without the application of heat.Sources of ignition, such as smoking and open flames, areprohibited where ethyl acrylate is handled, used, or stored.Metal containers involving the transfer of 5 gallons or moreof ethyl acrylate should be grounded and bonded. Drumsmust be equipped with self-closing valves, pressure vacuumbungs, and flame arresters. Use only nonsparking tools andequipment, especially when opening and closing containersof ethyl acrylate. Wherever ethyl acrylate is used, handled,manufactured, or stored, use explosion-proof electricalequipment and fittings | [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. |
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