2-Ethylhexylacrylat

2-Ethylhexyl acrylate

HCID 7636

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

2-ETHYLHEXYL ACRYLATE103-11-72-Ethylhexyl 2-propenoateAcrylic acid, 2-ethylhexyl ester2-Ethyl-1-hexyl acrylate2-Propenoic acid, 2-ethylhexyl esterDTXSID90252971-Hexanol, 2-ethyl-, acrylateacrylic acid 2-ethylhexyl esterHR49R9S6XGDTXCID405297RefChem:6740
Weitere Namen anzeigen
2-EHAEHA2-ethyl2-ETHYLHEXYL ACRYLATE extrapureAcrylic acid 2-ethylhexyl2-ETHYLHEXYL ACRYLATE MONOMEROCTYL ACRYLATEPropenoic acid 2-ethylhexyl ester2-ETHYLEXYL ACRYLATE
203-080-7618-950-52-ethylhexyl prop-2-enoate2-ETHYLHEXYLACRYLATENSC 4803Mono(2-ethylhexyl) acrylate2-Ethylhexylester kyseliny akrylove2EHA

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

Experimentelle und physikochemische Eigenschaften

Chemical ClassesFlammable agents - 2nd degree
PolymersPlastics & Rubber -> (Meth)acrylates
LogP · 2 Einträge

log Kow = 4.09 /Estimated/

3.67

OdorPleasant
Density · 5 Einträge

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

Color/FormColorless liquid

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.)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

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 · 6 Einträge

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

Other Safety InformationIMAP assessments - 2-Propenoic acid, 2-ethylhexyl ester: Environment tier I assessment
Fire Hazards · 2 Einträge

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.

Fire PotentialModerate, when exposed to heat or flame ...
Health HazardsInhalation 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)
Hazards Summary · 1 Eintrag

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

Fire FightingUse powder, AFFF, foam, carbon dioxide. Use water spray. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures · 4 Einträge

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 · 1 Eintrag

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.

Safe StorageSeparated from strong oxidants. Cool. Keep in the dark. Store only if stabilized.
Firefighting HazardsContainers may explode in fire.
Exposure Control and Personal Protection5.0 [ppm]

Toxikologische Informationen

Ecotoxicity Values · 5 Einträge

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 · 3 Einträge

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).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure RoutesThe substance can be absorbed into the body by inhalation and by ingestion.
Signs and Symptoms · 4 Einträge

Cough. Sore throat.

Redness. Pain.

Redness. Pain.

Abdominal pain. Diarrhoea. Nausea. Vomiting.

Effluent Concentrations · 1 Eintrag

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).

Regulatorische Informationen

FDA Requirements2-Ethylhexyl acrylate is an indirect food additive for use only as a component of adhesives.

Sicherheitsdaten

F
10-23
wgk
1
tsca
TSCA listed
ridadr
UN 3334
hs_code
29161290
RTECS-Nr.
AT0855000

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

...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 · 1 Eintrag

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 · 5 Einträge

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 · 5 Einträge

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 · 6 Einträge

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.

ImpuritiesACRYLIC ACID-0.009% BY WT (MAX); 2-ETHYL 4-METHYL PENTYL ACRYLATE-0.4% BY WT (MAX); WATER-0.05% BY WT (MAX)
U.S. Exports · 5 Einträge

(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. Imports(1983) 1.36x10+9 g /Acrylates & Acrylic Acid/
U.S. Production · 3 Einträge

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/

Consumption Patterns45% 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/

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.

Anbieter23 Anbieter

郑州阿尔法化工有限公司+86-18530059196 · [email protected]
咸宁深蓝生物医药研发有限公司18171815831 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
上海维亦特生物科技有限公司15317051735 · [email protected]
湖北广奥生物科技有限公司027-02702759223056 18162699093 · [email protected]
Ergänzende Hinweise · 1 Eintrag

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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