Grundinformationen
- CAS
103-11-7- Standard-SMILES
C=CC(=O)OCC(CC)CCCC- InChIKey
GOXQRTZXKQZDDN-UHFFFAOYSA-N- Summenformel
- C11H20O2
- Durchschnittliche Molmasse
- 184,27 g/mol
- Monoisotopische Masse
- 184,14632988
Überblick
2-Ethylhexyl acrylate can cause cancer according to California Labor Code and the World Health Organization's International Agency for Research on Cancer (IARC).
Namen und Bezeichner
- Bevorzugter Name
- 2-Ethylhexyl acrylate
- IUPAC
- 2-ethylhexyl prop-2-enoate
- Lokaler Name
- 2-Ethylhexylacrylat
- Englischer Name
- 2-Ethylhexyl acrylate
- Summenformel
- C11H20O2
- Molmasse
- 184.28
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
103-11-7、1322-13-0、9003-77-4、90530-31-7、93460-77-6- PubChem CID
- 7636
- DTXSID
DTXSID9025297- ChEMBL
CHEMBL1574328- ChEBI
CHEBI:82465- UNII
- HR49R9S6XG
- EC Number
- 203-080-7、215-330-2、292-071-1、618-950-5
- Nikkaji
- J3.601C
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,8
- Polarare Oberfläche (TPSA)
- 26,3 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 8
- Schwere Atome
- 13
- Formalladung
- 0
- Komplexität
- 152
Experimentelle und physikochemische Eigenschaften
LogP
log Kow = 4.09 /Estimated/
3.67
Density
0.885 at 68 °F (USCG, 1999) - Less dense than water; will float
0.880 g/cu cm at 25 °C
Relative density (water = 1): 0.89
0.885
0.8869 @ 20°C
Solubility
less than 1 mg/mL at 72 °F (NTP, 1992)
100 mg/l @ 25 °C
Solubility in water: none
Flash Point
180 °F (NTP, 1992)
180 °F (82 °C) (open cup)
86 °C (closed cup)
82 °C o.c.
180 °F
Boiling Point
417 to 424 °F at 760 mmHg (NTP, 1992)
214-218 °C
Boiling point: 130 °C @ 50 mm Hg; conversion factor: 1 ppm = 7.52 mg/cu cm
213.5 °C
417-424 °F
Melting Point
-130 °F (NTP, 1992)
-90 °C
-90 °C
-130 °F
-90 °C
Vapor Density
6.35 (NTP, 1992) - Heavier than air; will sink (Relative to Air)
6.35 (Air= 1)
Relative vapor density (air = 1): 6.35
6.35
Physikochemische Eigenschaften
- Schmelzpunkt
- -90 °C · -90°C
- Siedepunkt
- 215 · 215-219 °C(lit.)
- Dichte
- 0.885 g/mL · 0.885 g/mL at 25 °C(lit.)
- Dampfdichte
- 6.4 · 6.4 (vs air)
- Dampfdruck
- 0.15 mm · 0.15 mm Hg ( 20 °C)
- Brechungsindex
- 20 · n20/D 1.436(lit.)
- Flammpunkt
- 175 °F · 175 °F
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- 0.1 g/l · 0.1g/l
- Aggregatzustand
- Liquid
- Farbe
- Clear
- Geruch (Odor)
- Ester like odour
- Explosionsgrenze
- 0.9 · 0.9-6.0%(V)
- Wasserlöslichkeit
- 0.1 g/100 · <0.1 g/100 mL at 22 ºC
- BRN
- 1765828 · 1765828
- Henry's Law Constant
- 2.3 · 2.3×10-2 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Stabilität
- Stability Stable, but polymerizes readily, so is usually inhibited with hydroquinone or its monomethyl ether. Susceptible to hydrolysis. Combustible. Incompatible with oxidizing agents.
- Kosmetik-Inhaltsstoffe Funktionen
- BINDING
- InChI
- 1S/C11H20O2/c1-4-7-8-10(5-2)9-13-11(12)6-3/h6,10H,3-5,7-9H2,1-2H3
- InChIKey
- GOXQRTZXKQZDDN-UHFFFAOYSA-N
- SMILES
- CCCCC(CC)COC(=O)C=C
- LogP
- 4 at · 4 at 20℃
- CAS Datenbank
- 103 · 103-11-7(CAS DataBase Reference)
- NIST chemische Informationen
- 2 · 2-Propenoic acid, 2-ethylhexyl ester(103-11-7)
- EPA chemische Informationen
- 2 · 2-Ethylhexyl acrylate (103-11-7)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H315: Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P271, P272, P280, P302+P352, P304+P340, P319, P321, P332+P317, P333+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for < 0.1% (1 of 3581) of reports.
Warning
H315 (> 99.9%): Causes skin irritation [Warning Skin corrosion/irritation]
Gefahrenhinweise
Regulatory Information
Chemical: 2-Propenoic acid, 2-ethylhexyl ester
Hazard Traits - Carcinogenicity
Council Directive (EEC) No 109/1989 (Repealed by Reg. EC No 1935/2004 (amended))
2-Propenoic acid, 2-ethylhexyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-ethylhexyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 16-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15362
2-Propenoic acid, 2-ethylhexyl ester: Does not have an individual approval but may be used under an appropriate group standard
Fire Hazards
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.
Hazards Summary
Allergic contact dermatitis reported from surgical tape; [Kanerva, p. 1741] If left on clothing, can cause reddening of skin; [CHRIS] Severly irritating to skin and eyes; [HSDB] Readily polymerized by light, heat, and peroxides; A skin, eye, and respiratory tract irritant; May cause skin sensitization; [ICSC] An eye irritant; Inhalation may cause drowsiness and convulsions; [CAMEO] Irritating but not corrosive to skin; Potential for severe respiratory irritation, based on animal studies; Studies of guinea pigs have shown moderate skin sensitization potential (with and without adjuvant); Skin sensitization also reported in humans; [EC] Readily polymerizes unless inhibited with hydroquinone or its monomethyl ester; [NTP] Danger of skin sensitization; [MAK] Inhibited with 40-100 ppm MEHQ; A skin, respiratory tract, and severe eye irritant; May cause skin sensitization; A lachrymator; [Aldrich MSDS]
Sicherheit und Schutzausrüstung
First Aid Measures
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.
Rinse mouth. Give one or two glasses of water to drink. Do NOT induce vomiting. Refer for medical attention .
First Aid
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.
Storage Conditions
Materials which are toxic as stored or which can decompose into toxic components ...should be stored in a cool well-ventilated place, out of the direct rays of the sun, away from areas of high fire hazard, and should be periodically inspected. Incompatible materials should be isolated... .
Separate from heat, oxidizers, and sunlight. Store in a cool, dry, well-ventilated location. Outside or detached storage is preferred.
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. Temp must be kept low to minimize formation of peroxides and other products. Moisture may cause rust-initiated polymerization. /Acrylic acid & derivatives/
This product should be stored in a closed ocntainer, away from direct sunlight, at ambient temperatures. Storage of this product at elevated temperatures (>30 °C or >85 °F) reduces the shelf-life. ...An air space is required above the liquid in all containers; avoid storage under an oxygen-free atmosphere. ...Materials recommended for packaging include: stainless steel, mild steel, aluminum, glass, /high density polyethylene, polypropylene or polytetrafluoroethylene/. /Formulation >99% 2-ethylhexyl acrylate/
Disposal Methods
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.
Spillage Disposal
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.
Preventive Measures
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/
Toxikologische Informationen
Ecotoxicity Values
EC50 Scenedesmus subspicatus (algae; cell multiplication inhibition) 44 mg/L/72 hr
EC50 Scenedesmus subspicatus (algae; cell multiplication inhibition) 47 mg/L/96 hr
LC50 Artemia salina (Brine shrimp) 72 mg/L/24 hr /Conditions of bioassay not specified/
LC50 Leuciscus idus melanotus (Carp) 23 mg/L/48 hr /Conditions of bioassay not specified/
LC50 Carassius auratus (Goldfish) 200 mg/L/72 hr /Conditions of bioassay not specified/
Environmental Fate
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).
Signs and Symptoms
Cough. Sore throat.
Redness. Pain.
Redness. Pain.
Abdominal pain. Diarrhoea. Nausea. Vomiting.
Effluent Concentrations
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).
Soil Adsorption/Mobility
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.
TSCA Test Submissions
2-Ethylhexyl acrylate was tested for mutagenic activity at the thymidine kinase (TK) locus in L5178Y mouse lymphoma cells with and without metabolic activation provided by Aroclor-induced rat liver S9 fraction. The test article was administered at concentrations ranging from 1.95 to 60.0 nl/ml in the absence of activation, and from 7.8 to 150 nl/ml in the presence of activation. In the presence of S9, the mutation frequency was increased at the 70 and 150 nl/ml dose levels (2.2 to 4.6 times greater than controls), while an increase in mutation frequency at 15.6 nl/ml in the absence of S9 was not reproducible. The cytotoxicity of 2-ethylhexyl acrylate, as indicated by the relative growth parameter, ranged from 68% at 70 nl/ml to 8% at 150 nl/ml in the activated trials.
Atmospheric Concentrations
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).
Human Toxicity Excerpts
/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.
Regulatorische Informationen
Sicherheitsdaten
- F
- 10-23
- wgk
- 1
- tsca
- TSCA listed
- ridadr
- UN 3334
- hs_code
- 29161290
- RTECS-Nr.
- AT0855000
- risk_code
- 37/38-43
- Toxizität
- LD50 orally in Rabbit: 4435 mg/kg LD50 dermal Rabbit 7522 mg/kg
- hazard_code
- Xi
- safety_code
- 36/37-46
- Speicherklasse
- 10 - Combustible liquids
- Giftige Stoffe Daten
- 103-11-7(Hazardous Substances Data)
- Hazard Classifications
- Aquatic Chronic 3Skin Irrit. 2Skin Sens. 1STOT SE 3
- Selbstentzündungstemperatur
- 496 °F
Chemie und Industrie
Pharmakologische Informationen
Mechanism of Action
...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.
Biological Half-Life
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.
Metabolism/Metabolites
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.
Absorption, Distribution and Excretion
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.
Verwendung und Herstellung
Uses
Used as a monomer for plastics, protective coatings, and paper treatment, in copolymerization of vinyl acetate and vinyl chloride, and in the manufacture of water-based paints, adhesives, printing inks, impregnating agents, and reactive diluent/cross-linking agents; [HSDB] Used to make polymers and copolymers that are usually further processed to aqueous polymer dispersions--used mainly in adhesives and paints; Also used for coating raw materials, in the plastics industry, and as a monomer in construction industry chemicals (concentrations of 0.1-21%); [EC]
Monomer for plastics, protective coatings, paper treatment; in water-based paints
In vinyl acetate copolymerization
In vinyl chloride copolymerization
Acrylic acid, 2 ethylhexyl ester is used... in the production of water-based paints intended for use in contact with food or drink.
... Used to manufacture coating materials (especially emulsion paints), adhesives, printing inks, impregnating agents, and reactive diluent/cross-linking agents.
U.S. Exports
(1972) 1.29X10+10 G (PLUS BUTYL & METHYL)
(1975) 2.43X10+9 G (PLUS BUTYL & METHYL)
(1984) 1.63X10+10 g
(1987) 3.41X10+6 lb
(1988) 3.32X10+6 lb
U.S. Production
2023: 250,000,000 - <400,000,000 lb
(1984) 3.96X10+10 g
(1985) United States 36,020 tons; Western Europe 50,000 tons; Japan 29,000 tons. /From table/
Methods of Manufacturing
REACTION OF ACETYLENE, CARBON MONOXIDE, AND 2-ETHYLHEXANOL (MODIFIED REPPE PROCESS)
In ... propylene oxidation process acrolein is first formed by the catalytic oxidation of propylene vapor at high temp in the presence of steam. The acrolein is then oxidized to acrylic acid. ... The acrylic acid is esterified with alcohol to the ... acrylic ester in a separate process. /Acrylic ester monomers/
The acrylates can be manufactured by a number of procedures. These include dehydration of the corresponding hydroxyalkanoic acid, saponification of the alkaline nitrile, catalytic hydration of acetylene and carbon monoxide, or the reaction of acetone with hydrocyanic acid. /Acrylates/
Formulations/Preparations
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).
Household Products
Cosmetics product ingredient: 2-Ethylhexyl acrylate (Ethylhexyl Acrylate)
Information on 1 consumer products that contain 2-ethylhexyl acrylate in the following categories is provided:
General Manufacturing Information
Plastics Material and Resin Manufacturing
2-Propenoic acid, 2-ethylhexyl ester: ACTIVE
Anwendungen
Verwenden2-ethylhexyl acrylate is a monomer for plastics, protective coating, paper treatment, water-based paints, UV-curable coatings, and inks; in so me acrylicbased adhesive tapes.
Darstellung
synthetische2-Ethylhexyl acrylate is obtained by esterifying acrylic acid and 2-ethylhexanol with sulfuric acid as a catalyst, and subsequently neutralizing, dealcoholizing and rectifying the mixture.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter23 Anbieter
Ergänzende Hinweise
DefinitionChEBI: 2-Ethylhexyl acrylate is an ester of enoic acid. It is commonly used as a plasticizing co-monomer in the production of resins, which are utilized in various applications such as adhesives, latex, paints, textile and leather finishes, and coatings for paper.
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