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Home > Encyclopedia > 2-Ethylhexyl acrylate

2-Ethylhexyl acrylate

2-Ethylhexyl acrylate structure

2-Ethylhexyl acrylate 

structure
  • CAS No:

    103-11-7

  • Formula:

    C11H20O2

  • Chemical Name:

    2-Ethylhexyl acrylate

  • Synonyms:

    2-Propenoic acid,2-ethylhexyl ester;Acrylic acid,2-ethylhexyl ester;2-Ethylhexyl acrylate;2-Ethylhexyl 2-propenoate;NSC 4803;2EHA;Norsocryl 2-EHA;EHA;JR 910;45016-65-7;78733-32-1;84948-57-2;93460-77-6;126830-02-2;1329996-89-5;1453489-97-8

  • Categories:

    Cosmetic Ingredient  >  Binding Agent

Description

Clear liquid with a pleasant odor.


2-ethylhexyl acrylate appears as a clear colorless liquid with a pleasant odor. Less dense than water and insoluble in water. Vapors heavier than air. Flash point 180°F. Used in making of paints and plastics.|Liquid|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.|Clear liquid with a pleasant odor.


2-ethylhexyl acrylate appears as a clear colorless liquid with a pleasant odor. Less dense than water and insoluble in water. Vapors heavier than air. Flash point 180°F. Used in making of paints and plastics.|2-Ethylhexyl acrylate is an enoate ester.

2-Ethylhexyl acrylate Basic Attributes

184.27500

184.28

618-950-5

0478

4803

1993

DTXSID9025297|DTXSID0050398

Colorless liquid

29161290

Characteristics

26.30000

3.8

Colourless liquid

0.880 g/cm3 @ Temp: 25 °C

-90 °C

214-218 °C

86ºC

1.434-1.436

H2O: <0.1 g/100 mL at 22 ºC

Storage Room low temperature ventilation drying

0.143mmHg at 25°C

6.35

Lower flammable limit: 0.7% by volume; Upper flammable limit: 8.2% by volume

vol% in air: 0.8.4

Pleasant

Henry's Law constant: 0.000432 atm-cu m/mol @ 25 °C /Estimated/

Polymerizes readily, unless inhibited|Sets to glass at -90 °C|SHARP, MILD-ESTER TYPE, INOFFENSIVE ODOR; LIQUID SURFACE TENSION (ESTIMATED): 26 DYNES/CM; LATENT HEAT OF VAPORIZATION: 110 BTU/LB; LIQUID-WATER INTERFACIAL TENSION (ESTIMATED): 30 DYNES/CM; HEAT OF POLYMERIZATION: -142 BTU/LB; HEAT OF COMBUSTION: -15500 BTU/LB /INHIBITED/|Liquid heat capacity= 0.421 BTU/lb-F @ 70 °F; Liquid thermal conductivity= 1.048 BTU-in/hr-sq ft-F at 70 °F; Liquid viscosity: 1.761 cP at 70 °C; Saturated vapor pressure= 0.011 lb/sq in @ 100 °F; Saturated vapor density= 0.00035 lb/cu ft @ 100 °F; Solubility in water: 0.340 lb/100 lb at 68 °C /Inhibited/|Heat of evaporation: 0.25 kJ/g; specific heat: 1.92 J/g °C|React readily with electrophilic, free-radical, and nucleophilic agent /Acrylic acid and esters/|For more Other Experimental Properties (Complete) data for 2-ETHYLHEXYL ACRYLATE (7 total), please visit the HSDB record page.

Insoluble in water.

Acrylates and Acrylic Acids

Polymerizable

2-ETHYLHEXYL ACRYLATE polymerizes readily in the presence of heat and light generating much heat; reacts with strong oxidants. REF [Handling Chemicals Safely, 1980. p. 235].

496 °F (USCG, 1999)|485 °F (252 °C)|252 °C

Lower flammable limit: 0.7% by volume; Upper flammable limit: 8.2% by volume

Vapours are uninhibited and may polymerize, causing blockage of vents.

Safety Information

UN3334 9

1

R37/38; R43

S36/37-S46

AT0855000

Xi

Separated from strong oxidants. Cool. Keep in the dark. Store only if stabilized.

Stability Stable, but polymerizes readily, so is usually inhibited with hydroquinone or its monomethyl ether. Susceptible to hydrolysis. Combustible. Incompatible with oxidizing agents.

P273-P280-P304 + P340 + P312-P333 + P313

H315-H317-H335-H412

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.|Incineration.|The following wastewater treatment technologies have been investigated for 2-ethylhexyl-acrylate: Biological treatment.

Material will react with strong acids and alkalies.

2-Ethylhexyl acrylate is an indirect food additive for use only as a component of adhesives.

Behavior in Fire: Heat can result in a severe polymerization with rapid release of energy. Sealed containers may rupture explosively if hot. (USCG, 1999)|Combustible. Above 82 °C explosive vapour/air mixtures may be formed.|Flammable - 2nd degree, Reactive - 2nd degree

|Warning|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P280, P302+P352, P304+P340, P312, P321, P332+P313, P333+P313, P362, P363, P403+P233, P405, and P501|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P273, P280, P302+P352, P304+P340, P312, P321, P332+P313, P333+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 3566 companies from 42 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Aggregated GHS information provided by 11 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H227: Combustible liquid [Warning Flammable liquids]|P210, P260, P261, P264, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P312, P314, P321, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501|P201, P202, P210, P260, P261, P264, P271, P272, P273, P280, P281, P302+P352, P304+P340, P308+P313, P312, P314, P321, P332+P313, P333+P313, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501

Self-contained breathing apparatus; rubber gloves; vapor- proof chemical safety goggles; impervious apron and boots. (USCG, 1999)|Wear full protective clothing and positive pressure self contained breathing apparatus.|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 & derivatives/|... Gloves and protective clothing and shoes or boots should be used in addition to eye (or full face) protective equipment. /Acrylic acid & derivatives/

Moderate, when exposed to heat or flame ...

Above 82 °C explosive vapor/air mixtures may be formed.|Explosive limits, vol% in air: 0.8-6.4|Explosive limits , vol% in air: 0.8-6.4

Use water spray, dry chemical, foam, or carbon dioxide. Use water spray to keep fire-exposed containers cool. Water or foam may cause frothing. Fight fire from protected location or maximum possible distance.

Containers may explode in fire.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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 such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|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 irritant 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/

A severe skin and eye irritant.|/Ethyl acrylate/ vapors are highly irritating to the nose, eyes and respiratory tract. It can cause corneal lesions, and inspiration of high concentrations of the vapors can lead to pulmonary edema. /acrylates/|The lower molecular weight esters of acrylic acids are irritants to skin, eyes and mucous membranes. /Acrylic acid esters/

Personal protection: chemical protection suit and filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in covered containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Separated from strong oxidants. Cool. Keep in the dark. Store only if stabilized.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is irritating to the eyes, skin and respiratory tract.

Repeated or prolonged contact may cause skin sensitization.

NO open flames. Above 82 °C use a closed system, ventilation and explosion-proof electrical equipment.

AVOID ALL CONTACT!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles or eye protection in combination with breathing protection.

| 1 - Materials that, under emergency conditions, can cause significant irritation.| 2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.| 1 - Materials that in themselves are normally stable but that can become unstable at elevated temperatures and pressures.

2-Ethylhexyl acrylate was detected at concn ranging from 0.6-11 ppb, 4 ppb mean concn, in the effluent from the last stage of an on-site waste treatment facility which received wastewater from a large petrochemical plant(1). The influent untreated wastewater contained 0.55-5.6 ppm, 2.0 ppm mean concn, of 2-ethylhexyl acrylate(1). 2-Ethylhexyl acrylate was identified in 9 occurrences in an air chamber under dynamic conditions used to test emissions of volatile organic compounds from different furniture coatings(2). A total of 44 furniture samples manufactured under industrial conditions with different coatings were tested(2). Samples 1-17 were placed in the chamber immediately after production and monitored for 30-40 days(2). Samples 18-44 were preconditioned after production for 19 days in a special climate room with an air exchange of 0.5-1.0 1/hr(2).

Mean time weighted average (TWA) 2-ethylhexyl acrylate concn of <1-2 ppb were detected in the breathing zone of workers near 2 polymerization reactors and a loading dock in a polystyrene production plant(1). The chemical was not detected in the breathing zone of workers near 2 other polymerization reactors(1). The individual TWA concn detected in the breathing zone of workers ranged from <1 ppb to 5 ppb(1). A TWA concn of 161 ppb was detected in the general area atmosphere of one of the reactors(1).

Toxicity

LD50 Rat oral 6500 uL/kg|LD50 Rat ip 1670 mg/kg|LD50 Mouse oral 4400 mg/kg|LD50 Mouse ip 1326 mg/kg|For more Non-Human Toxicity Values (Complete) data for 2-ETHYLHEXYL ACRYLATE (9 total), please visit the HSDB record page.

2-Ethylhexyl acrylate's production and use in the manufacture of plastics, protective coatings, papers treatments, and water-based paints(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 430(SRC), determined from a structure estimation method(2), indicates that 2-ethylhexyl acrylate is expected to have moderate mobility in soil(SRC). Volatilization of 2-ethylhexyl acrylate from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 0.000432 atm-cu m/mole(SRC), derived from its vapor pressure, 0.178 mm Hg(3) and water solubility, 100 mg/L(4). 2-Ethylhexyl acrylate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Biodegradation data in soil were not found; however, 2-ethylhexyl acrylate was found to biodegrade 51 to >90% in biodegradation screening tests(4,5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 430(SRC), determined from a structure estimation method(2), indicates that 2-ethylhexyl acrylate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 0.000432 atm-cu m/mole(SRC), derived from its vapor pressure, 0.178 mm Hg(4) and water solubility, 100 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 7 hours and 6 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 280(SRC), from an estimated log Kow of 4.09(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not altered physically or chemically once released into the environment(SRP). No hydrolysis data are available for 2-ethylhexyl acrylate; however, hydrolysis is expected to be an important environmental fate process for 2-ethylhexyl acrylate but only at alkaline pHs(SRC). The base-catalyzed second-order hydrolysis rate constant for an analogous compound, ethyl acrylate, is reported to be 0.078 L/mol-s(9), which corresponds to half-lives of 3 years, 103 and 10 days at pH 7, 8, and 9, respectively(SRC). Biodegradation data in water were not found; however, 2-ethylhexyl acrylate was found to biodegrade 51 to >90% in biodegradation screening tests(5,10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-ethylhexyl acrylate, which has a vapor pressure of 0.178 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-ethylhexyl acrylate 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 19 hours(SRC), calculated from its rate constant of 2.0X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). The rate constant for the vapor-phase reaction of 2-ethylhexyl acrylate with ozone has been estimated as 1.8X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). This corresponds to an atmospheric half-life of about 6.5 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(4). 2-Ethylhexyl acrylate is not expected to be susceptible to direct photolysis by sunlight, since it does not contain functional groups that are expected to absorb light with wavelengths >290 nm(SRC).

The rate constant for the vapor-phase reaction of 2-ethylhexyl acrylate with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 19 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of 2-ethylhexyl acrylate with ozone has been estimated as 1.8X10-16 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 6.5 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). No hydrolysis data are available for 2-ethylhexyl acrylate; however, hydrolysis is expected to be an important environmental fate process for 2-ethylhexyl acrylate only at alkaline pHs(SRC). The base-catalyzed second-order hydrolysis rate constant for an analogous compound, ethyl acrylate, is reported to be 0.078 L/mol-s(3), which corresponds to half-lives of 3 years, 103 and 10 days at pH 7, 8, and 9, respectively(SRC). 2-Ethylhexyl acrylate is not expected to be susceptible to direct photolysis by sunlight, since it does not contain functional groups that are expected to absorb light with wavelengths >290 nm(SRC).

An estimated BCF of 430 was calculated for 2-ethylhexyl acrylate(SRC), using an estimated log Kow of 4.09(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not altered biologically or chemically once released into the environment(SRP).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2-ethylhexyl acrylate can be estimated to be 430(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-ethylhexyl acrylate is expected to have moderate mobility in soil.

The Henry's Law constant for 2-ethylhexyl acrylate is 0.000432 atm-cu m/mole(SRC) derived from its vapor pressure, 0.178 mm Hg(1), and water solubility, 100 mg/L(2). This Henry's Law constant indicates that 2-ethylhexyl acrylate is expected to volatilize from water surfaces(3). 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)(3) is estimated as 7 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)(3) is estimated as 6 days(SRC). 2-Ethylhexyl acrylate's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 2-Ethylhexyl acrylate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 11,277 workers (2,341 of these are female) are potentially exposed to 2-ethylhexyl acrylate in the US(1). Occupational exposure to 2-ethylhexyl acrylate may occur through inhalation and dermal contact with this compound at workplaces where 2-ethylhexyl acrylate is produced or used(SRC). The most probable route of human exposure to 2-ethylhexyl acrylate is by inhalation of contaminated air especially at workplaces where 2-ethylhexyl acrylate is manufactured and used(2) Monitoring data are limited(SRC). The general population may be exposed to 2-ethylhexyl acrylate via inhalation of ambient air(SRC) containing 2-ethylhexyl acrylate from products such as commercial furniture coatings(3).

Drug Information

2-Ethylhexyl acrylate is believed to undergo carboxylesterase-catalysed metabolism, like other acrylate esters. It is excreted in the urine both as N-acetyl-S-(2- carboxyethyl)cysteine and as N-acetyl-S-2-(2-ethylhexyloxycarbonyl)ethylcysteine. Two unidentified metabolites were detected in the bile of rats. In rats exposed by inhalation, the percentage of a dose of the acrylate excreted in urine as thioethers over 24 hr was dose dependent and decreased from 8.0 to 3.0% as the 6 hr exposure concentration in air increased from 250 to 1000 mg/cu m, indicating saturable metabolism along this pathway. A decrease in the number of non-protein SH groups was also observed in the blood and liver of these animals.|The toxicokinetics of carbon-14 labeled 2-ethylhexyl-acrylate (2EHA) was assessed in 4 and 7 month old male Wistar-rats. The chemical was administered by iv or ip injection at a dose of 10 mg/kg, and the animals were maintained in metabolism cages until sacrifice at 1, 2, 12, and 24 hr post dosing. A biexponential elimination of radioactivity was observed in both 4 and 7 month old male animals following the administration of labeled 2EHA through iv or ip routes. The half lives of the slow and fast phases of elimination were 5-6 hr and 30-60 min in the younger animals and 14 hr and 115-130 min in the older animals respectively. The rank order of tissue concentrations of 2EHA following iv dosing was kidney, liver, brain, thymus, spleen, lungs, heart, testes, blood, fat. Tissue levels of the acrylate were lower following ip administration, but followed a similar pattern. The major routes of elimination during the first 12 hours after both dosing regimen was expired air and urinary excretion. Expired air accounted for approximately 50% of the radioactivity administered at 24 hr post treatment with another 7-13% determined in the urine. Trapping the exhaled radioactivity in 2 molar sodium-hydroxide and gas chromatographic analysis revealed that the primary metabolite was carbon-dioxide.|The disposition of ...2-ethylhexylacrylate (EHA) was studied in rats. Adult male Wistar-rats were given a single oral or ip 100 mg/kg dose of carbon-14 (C-14) labeled ...EHA. ...More than 90% of the dose was excreted within 72 hours by all animals, mostly in the expired air and urine. Urinary excretion of radiolabel was higher for animals dosed orally. Maximum C-14 concentrations in the plasma and erythrocytes occurred ...3 hours after dosing with EHA. Elimination of C-14 from erythrocytes was biphasic for both compounds. In plasma EHA was eliminated monophasically with a halflife of about 22 hours. ...EHA derived activity was widely distributed to all tissues. The amounts of tissue radioactivity decreased slowly. Small increases in the amount of EHA derived activity were found in the adipose tissue, sciatic nerve, and brain 72 hours after dosing. ...The retention of EHA derived C-14 activity in the adipose tissue and sciatic nerve 72 hours after dosing suggests that EHA may accumulate in living organisms.|Excretion balance studies were conducted with 2-ethylhexanol (2-EH) in female Fischer 344 rats following single high (500 mg/kg) and low (50 mg/kg) oral doses of [14C]2-EH, following repeated oral dosing with unlabelled 2-EH at the low level, following dermal exposure for 6 hr with a 1 g/kg applied dose of [14C]2-EH, and following a 1 mg/kg iv dose of [14C]2-EH. The high, low and repeated low oral dose studies with 2-EH showed similar excretion balance profiles of [14C], with some evidence of metabolic saturation at the high dose. No evidence of metabolic induction was seen following the repeated low oral dosing. All of the oral doses were eliminated rapidly, predominantly in the urine during the first 24 hr following dosing. The dermal dosing resulted in only about 5% absorption of the 1 g/kg dose, with the major portion of the dose recovered unabsorbed from the dermal exposure cell at 6 hr. Urinary metabolites eliminated following the oral and dermal doses were predominantly glucuronides of oxidized metabolites of 2-EH, including glucuronides of 2-ethyladipic acid, 2-ethylhexanoic acid, 5-hydroxy-2-ethylhexanoic acid and 6-hydroxy-2-ethylhexanoic acid. /2-Ethylhexanol, metabolite/|Rats were intravenously administered (14C)-2-ethylhexyl acrylate at the dose 10 mg/kg or 50 mg/kg b. w. ... Highest radioactivity was found in liver, less in the kidneys and the least in the brain. A significant increase of bile flow was observed. In the 24-hour intervals 2.2% of the dose was eliminated via bile at both dosages, most of it (83%) during the first 3 hours.

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. /Acrylates/|Excretion balance studies were conducted with 2-ethylhexanol (2-EH) in female Fischer 344 rats following single high (500 mg/kg) and low (50 mg/kg) oral doses of [14C]2-EH, following repeated oral dosing with unlabelled 2-EH at the low level, following dermal exposure for 6 hr with a 1 g/kg applied dose of [14C]2-EH, and following a 1 mg/kg iv dose of [14C]2-EH. ...Urinary metabolites eliminated following the oral and dermal doses were predominantly glucuronides of oxidized metabolites of 2-EH, including glucuronides of 2-ethyladipic acid, 2-ethylhexanoic acid, 5-hydroxy-2-ethylhexanoic acid and 6-hydroxy-2-ethylhexanoic acid. /2-Ethylhexanol, metabolite/|From toxicokinetic studies, it can be concluded by analogy with other acrylates that 2-ethylhexyl acrylate is hydrolysed relatively quickly by carboxyl esterases to alcohol and acrylic acid. ...Studies of the metabolites deal only with the detection of mercapturic acid derivatives of 2-ethylhexyl acrylate and acrylic acid in bile.|2-Ethylhexanol is a metabolite of 2-ethylhexyl acrylate.|2-Ethylhexyl acrylate is believed to undergo carboxylesterase-catalysed metabolism, like other acrylate esters. It is excreted in the urine both as N-acetyl-S-(2- carboxyethyl)cysteine and as N-acetyl-S-2-(2-ethylhexyloxycarbonyl)ethylcysteine.

The toxicokinetics of carbon-14 labeled 2-ethylhexyl-acrylate (2EHA) was assessed in 4 and 7 month old male Wistar-rats. ...The half lives of the slow and fast phases of elimination were 5-6 hr and 30-60 min in the younger animals and 14 hr and 115-130 min in the older animals respectively.

...Male Wistar rats /were/ exposed to acrylic acid derivatives. The 6-hr inhalation of acrylonitrile (AN), methyl acrylate (MA), ethyl acrylate (EA), n-butyl acrylate (BA) and 2-ethylhexyl acrylate (2-EHA) in several concentrations increased the urinary thioether excretion; the portion metabolized to thioethers was... only 1.5-8% for the acrylates. Total-SH levels in the liver significantly decreased after the inhalation of AN, EA, BA and 2-EHA. ...Most pronounced NP-SH depletion was in the liver, less in blood and moderate in brain and lungs. There was an exponential relationship between the tissue NP-SH and the inhaled concentrations. Calculated concentrations inducing 50% NP-SH depletion indicated that reaction of acrylic acid derivatives with SH groups was decreasing in the order AN >>2-EHA >EA = BA for the chemicals and liver >blood >lungs >brain for the tissues. All inhaled acrylates induced hyperglycemia... . The chemical reactivity of acrylates with glutathione (GSH) decreased in the order EA >BA >MA >AN >2-EHA. The results suggest that GSH depletion may participate in acute lethal and biochemical toxic effects of acrylic acid esters.

ACRYLIC ACID-0.009% BY WT (MAX); 2-ETHYL 4-METHYL PENTYL ACRYLATE-0.4% BY WT (MAX); WATER-0.05% BY WT (MAX)

Inhalation of concentrated vapor causes drowsiness and convulsions. Liquid causes irritation of eyes and may irritate skin on prolonged exposure. Ingestion produces same symptoms as inhalation. (USCG, 1999)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)


Fresh air, rest. Refer for medical attention.


Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. 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 ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

/HUMAN EXPOSURE STUDIES/ 2-Ethylhexyl acrylate causes dermatitis, but effective dermal protection is provided by gloves.|/HUMAN EXPOSURE STUDIES/ ... Data from a total of 275 patients with histories of methacrylate exposure tested with the series between 1985 and 1995 were examined. An allergic reaction to at least one methacrylate in the series was seen in 17.5% of the patients. The compounds most commonly induced an allergic patch reaction were 2-hydroxyethyl-acrylate, 2-hydroxypropyl-methacrylate, and 2-hydroxyethyl-methacrylate. No reactions to 2-ethylhexyl-acrylate, 2,2-bis(4-(methacryloxy)phenyl)propane, trimethylolpropane-triacrylate, oligotriacrylate-480, N,N-methylenebisacrylamide, or ethyl-cyanoacrylate were seen in any of the patients. These data showed large variations from those obtained in animal sensitization studies.|/HUMAN EXPOSURE STUDIES/ No allergic responses were recorded for 2-ethylhexyl acrylate /in a study reviewing 10 yr of patch testing data./|/HUMAN EXPOSURE STUDIES/ Among 13,833 patients suspected of contact dermatitis examined during the years 1978-1999, occupational contact allergy to (meth)acrylates was diagnosed in 31 patients. .../2-Ethylhexyl acrylate (test concentration: 0.5% in petrolatum) was not listed as an important occupational contact allergen./|For more Human Toxicity Excerpts (Complete) data for 2-ETHYLHEXYL ACRYLATE (8 total), please visit the HSDB record page.

2-ethylhexyl acrylate

The substance can be absorbed into the body by inhalation and by ingestion.

Cough. Sore throat.


Redness. Pain.


Redness. Pain.

2-Ethylhexyl acrylate Use and Manufacturing

Methods of Manufacturing

1、Direct esterification :Acrylic acid and 2-ethyl-hexanol esterificat by the sulfuric acid as the catalyst , and then by neutralize, dealcoholization and distillation to get the products.
2、Transesterification:Methyl acrylate and 2-ethylhexanol are in the presence of catalyst titanium tetrachloride transesterification reaction to produce 2-ethylhexyl acrylate , and then distillat to get the inished product.Ethyl methacrylate and 2-ethylethanolamine were mixed at a ratio of 3: 1 (mol ratio), and a gas phase transesterification reaction was carried out at 227 to 228℃ The catalyst was titanium tetrachloride supported on silica gel .The conversion was 32% and the yield was 97% .When the transesterification reaction is carried out in a liquid phase, the yield is 70 to 80%.In the reaction kettle by adding a certain amount of acrylic acid, isooctanol, catalyst (SO42- / ZrO2) and polymerization inhibitor phenothiazine heating back to the water separation The reaction solution was washed with caustic, washed with water to neutral vacuum distillation and then collect the productions. The amount of the catalyst is 5% of the mass of the acrylic acid, and the amount of the polymerization inhibitor is 0.05% of the mass of the acrylic acid. The ratio of raw materials (iso-octanol): (acrylic acid) = 1.2: 1 .Reaction temperature is 120 ℃, reaction time is 3 h.

Uses

Comonomer with vinyl acetate for polymer emulsion paints, with vinyl chloride for latex paints.


Adhesives and sealant chemicals


Adhesives and sealants

Production

250,000,000 - 500,000,000 lb|(1984) 3.96X10+10 g|(1985) United States 36,020 tons; Western Europe 50,000 tons; Japan 29,000 tons. /From table/

45% FOR COATINGS, 16% FOR TEXTILES & LEATHER FINISHES, 9% FOR PAPER FINISHES, 9% FOR PAPER COATINGS, 8% FOR ADHESIVES, 6% FOR POLYACRYLATES, 5% FOR POLISHES, 5% FOR ACRYLIC FIBERS, 6% OTHER (1983 EST) /ACRYLATES & ACRYLIC ACID/

GRADES OR PURITY: 99+%. /INHIBITED/|PURITY: 99.5% BY WT, MIN-INCLUDES 0.4% BY WT (MAX) OF 2-ETHYL 4-METHYL PENTYL ACRYLATE /INHIBITED/|INHIBITOR OF POLYMERIZATION: MONOMETHYL ETHER OF HYDROQUINONE, 13-120 PPM. HYDROQUINONE, 90-120 PPM. /INHIBITED/|NORSOCRYL(R) 2 Ethylhexyl Acrylate: >99% 2-ethylhexyl acrylate and 15 ppm monomethyl ether of hydroquinone (MEHQ).

Adhesive manufacturing|2-Propenoic acid, 2-ethylhexyl ester: ACTIVE|2-Propenoic acid, 2-ethylhexyl ester, homopolymer: ACTIVE|XU - indicates a substance exempt from reporting under the Chemical Data Reporting Rule, (40 CFR 711).

Chemical assay is preferably performed by gas-liquid chromatography or by the conventional methods for determination of unsaturation such as bromination or addition of mercaptan, sodium bisulfide, or mercuric acetate. /Acrylic acid & derivatives/|RETENTION TIMES FOR ACRYLATES WERE MEASURED WITH 2 DIFFERENT COLUMNS (C18 CORASIL & C8 LICHROSORB) USING REVERSE-PHASE HIGH PRESSURE LIQ CHROMATOGRAPHY IN ORDER TO OBTAIN THE PARTITION COEFFICIENTS OF ACRYLATES BETWEEN 1-OCTANOL AND WATER (LOG P). /ACRYLATES/|THE MONOMER CAN BE DETERMINED BY GAS CHROMATOGRAPHY.|AN AIR SAMPLING & ANALYSIS METHOD FOR MONITORING PERSONAL EXPOSURE TO VAPORS OF ACRYLATE MONOMERS WAS DEVELOPED. 2-ETHYLHEXYL ACRYLATE CONCN AS LOW AS 0.01 PPM BY VOL (PPMV) CAN BE MEASURED. THESE LIMITS OF SENSITIVITY ARE BASED ON A 60 MIN SAMPLE AT A FLOW RATE OF 500 CU M/MIN. THE ACRYLATE MONOMER VAPOR IS ADSORBED ON ACTIVATED SILICA GEL, DESORBED IN ACETONE, AND ANALYZED BY GAS CHROMATOGRAPHY USING FFAP OR OV-17 LIQUID PHASE COLUMNS.|Method: OSHA PV2026, Gas Chromatography using Flame Ionization Detector; Analyte: 2-ethylhexyl acrylate; Matrix: air; Detection Limit: 0.31 ug/sample (0.025 mg/cu m)

Fire Hazards -> Flammable - 2nd degree, Reactive - 2nd degree

Computed Properties

Molecular Weight:184.27
XLogP3:3.8
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:8
Exact Mass:184.146329876
Monoisotopic Mass:184.146329876
Topological Polar Surface Area:26.3
Heavy Atom Count:13
Complexity:152
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Downstream Products

Price Analysis

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  • Data: 2026-07-15
  • Price: 9100.00Yuan/mt
  • Change: 500.0

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