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2-Ethylhexylmethacrylat
2-EHMA · OCTYL METHACRYLATE · UNII:8Q7XLQ325N · CHLUMICRYI EHMA · Ethylhexyl Methacrylat · ETHYLHEXYLMETHACRYLATE · 2-ethylhexylmethacryate · 2-Ethylhexylmethacrylat
Identifikatoren & physikalische Daten
| CAS No. | 25719-51-1 |
|---|---|
| Summenformel | C12H22O2 |
| Durchschnittliche Molmasse | 198,3 g/mol |
| Monoisotopische Masse | 198,16197994 g/mol |
| SMILES | C=C(C)C(=O)OCC(CC)CCCC |
| InChIKey | WDQMWEYDKDCEHT-UHFFFAOYSA-N |
| PubChem CID | 12713 |
| ChEMBL | CHEMBL1871010 |
| EC No. | 211-708-6 |
| DTXSID | DTXSID3027293 |
| Lokaler Name | 2-Ethylhexylmethacrylat |
Chemische & physikalische Eigenschaften
| XLogP | 4,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 8 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 185 |
| Polymers | Plastics & Rubber -> (Meth)acrylates |
| LogP (Verteilungskoeffizient) | log Kow = 4.544.2-4.84.67 |
| Dichte | 0.880 g/cu cm @ 25 °CRelative density (water = 1): 0.90.885 g/mL at 25 °C(lit.) |
| Löslichkeit | Solubility in water: none<0.1g/l<0.1 g/L |
| Flammpunkt | 92 °C198 °F |
| Siedepunkt | 110 °C @ 14 mm Hg113-224 °C218 °C |
| Dampfdichte | 6.8 (Air= 1)Relative vapor density (air = 1): 6.86.9 (vs air) |
| Polymerization | The substance may polymerize due to warming.METHYL METHACRYLATE, AND IN GENERAL THE METHACRYLIC ESTERS, POLYMERIZE MUCH LESS READILY THAN THE CORRESPONDING ORDINARY ACRYLATES. NONE THE LESS, THEY ARE STABILIZED BY ADDING HYDROQUINONE OR PYROGALLOL, PARTICULARLY IN THE PRESENCE OF METALLIC COPPER. /METHACRYLATES/ |
| Dampfdruck | 0.07 [mmHg]VP: < 1 mm Hg at 20 °CConversion factor: 8.09 mg/cu m= 1 ppm0.076 mm Hg @ 25 °C /Estimated/Vapor pressure, Pa at 20 °C: 1330.13 hPa (20 °C) |
| Food Contact Substances | FCS -> FDA Cumulative Estimated Daily Intake (CEDI)FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR |
| Brechungsindex | Index of refraction: 1.436 @ 25 °Cn20/D 1.438(lit.) |
| Henry-Konstante | Henry's Law constant: 1.1X10-3 atm-cu m/mol @ 25 °C /Estimated/ |
| Schmelzpunkt | -50 °C |
| Lagerbedingungen | Store at +2°C to +8°C. |
| Aggregatzustand | Liquid |
| Farbe | Colorless |
| Wichte | 0.885 |
| Geruch | Ester like odour |
| Explosionsgrenze | 0.6%(V) |
| BRN | 1769420 |
| Stabilität | Stable, but may polymerize upon exposure to light. Heat sensitive. Incompatible with strong acids, strong oxidizing agents, strong bases. |
| Kosmetik-Inhaltsstoffe Funktionen | FILM FORMING |
| InChI | 1S/C12H22O2/c1-5-7-8-11(6-2)9-14-12(13)10(3)4/h11H,3,5-9H2,1-2,4H3 |
| InChIKey | WDQMWEYDKDCEHT-UHFFFAOYSA-N |
| SMILES | CCCCC(CC)COC(=O)C(C)=C |
| LogP (Verteilungskoeffizient) | 4.95 at 20℃ |
| CAS Datenbank | 688-84-6(CAS DataBase Reference) |
| NIST chemische Informationen | Octyl methacrylate(688-84-6) |
| EPA chemische Informationen | 2-Ethylhexyl methacrylate (688-84-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (41.7%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 835 reports by companies from 33 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H227: Combustible liquid [Warning Flammable liquids] |
|---|---|
| Regulatorische Informationen | Chemical: 2-Propenoic acid, 2-methyl-, 2-ethylhexyl ester2-Propenoic acid, 2-methyl-, 2-ethylhexyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-methyl-, 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: 20-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/147612-Propenoic acid, 2-methyl-, 2-ethylhexyl ester: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Weitere Sicherheitsinformationen | Evaluation - 2-Propenoic acid, 2-methyl-, 2-ethylhexyl ester (ethylhexyl methacrylate) |
| Brandgefahren | Combustible. |
| Brandpotenzial | Combustible. |
| Gefahrenübersicht | May polymerize if heatedA skin and eye irritant[ICSC] May polymerizeAn irritant and lachrymator[MSDSonline] See ACRYLIC RESINS (MONOMERS). |
| EG-Einstufung | Symbol: XiR: 36/37/38S: (2)-26-28Note: A |
| Special Reports | BIBRA working groupTA:Toxicity profile. BIBRA Toxicology International:19 (1996). |
| Chemical Dangers | The substance may polymerize due to warming. |
| Physical Dangers | Vapours are uninhibited and may polymerize in vents or flame arresters, causing blockage. |
| Hazard Classes and Categories | Skin Irrit. 2 (41.7%)Flammable liquids - Category 4 |
| Explosive Limits and Potential | This material polymerizes exothermically in the presence of heat, contamination, oxygen free atmosphere, free radicals, peroxides, and inhibitor depletion liberating heat. /Formulation >99% 2-ethylhexyl methacrylate/ |
| Skin, Eye, and Respiratory Irritations | The substance irritates the eyes and the skin. |
| Brandbekämpfung | Use water spray, powder, alcohol-resistant foam, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest.Remove contaminated clothes. Rinse and then wash skin with water and soap.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. |
| Sichere Lagerung | Cool. Store only if stabilized. |
| Lagerbedingungen | To avoid photoinitiation of polymerization, all methacrylates should be stored with minimal exposure to light.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/ |
| Entsorgungsverfahren | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Verschüttetes entsorgen | Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. |
| Preventive Measures | When designing a safe plant, among other important considerations, it is necessary to be aware of the considerable exothermic heat generated in some reactions. Thus, high pressure and temperatures may develop. Dangerous exposures can be avoided with careful design such as completely enclosing those processes where toxic chemical or intermediates occur.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.Employees should be instructed about the necessity of cleansing the skin if it is contaminated by materials which are irritants or skin-absorbed.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.Wear protective gloves to prevent skin exposure. If contact occurs, remove contaminated clothesrinse and then wash skin with water and soap. Wear safety glasses to prevent eye exposure. If contact occurs, first rinse with plenty of water for several minutes (remove contact lenses if easily possible), then take to a doctor. Do not eat, drink, or smoke during work. /From table/ |
| Eye Prevention | Wear safety spectacles. |
| Fire Prevention | NO open flames. |
| Inhalation Risk | 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. |
| Skin Prevention | Protective gloves. |
| Ingestion Prevention | Do not eat, drink, or smoke during work. |
| Unerwünschte Wirkungen | Lacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears. |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its aerosol. |
| Signs and Symptoms | Redness. |
| TSCA Test Submissions | A combined Repeat Dose and Reproductive/Developmental Toxicity Screen was conducted with 2-ethylhexyl methacrylate (CAS #688-84-6) on groups of Sprague-Dawley CD rats (12/sex/group). The test compound was administered in an olive oil vehicle at doses of 0, 30, 100, 300, or 1000 mg/kg/day by oral gavage for 49 days for males. Females received treatments from 14 days before mating through day 3 of lactation. Terminal sacrifice and necropsy took place the day after final dosing for both males and females. Absolute kidney weights and relative weights of pituitary, liver, and kidneys were increased in males from the 300 and 1000 mg/kg/day groups. Males in the highest dose group (1000 mg/kg/day) exhibited suppression of body weight gain, decreased food consumption, RBC, hemoglobin, hematocrit, WBC and total protein. Increased GOT, GPT, A/G ratio, BUN and CI, as well as focal necrosis in the liver and a decrease of extramedullary hematopoiesis in the spleen was seen in males receiving 1000 mg/kg. Females receiving 100 mg/kg and above showed increased relative kidney weights, while females in the high dose group exhibited suppression of body weight gain, decrease in food consumption, atrophy of the thymus, and increased absolute kidney, and relative liver and thyroid weights, and a decrease of extramedullary hematopoiesis in the spleen. There was one death among females receiving 1000 mg/kg/day. The numbers of corpora lutea and implantation scars were decreased for the high dose group. Decreased birth, live birth and viability indices, and decreased body weights of both male and female pups were seen on days 0 and 4 after birth. Decreased numbers of live pups born were seen in groups receiving 300 and 1000 mg/kg/day. NOELs for repeated dose toxicity were considered to be 100 mg/kg/day for males and 30 mg/kg/day for females. The NOELs for reproductive effects were considered to be 1000 mg/kg/day for males and 300 mg/kg/day for females and the NOEL for developmental effects was considered to be 100 mg/kg/day.2-Ethylhexyl methacrylate was tested for mutagenic potential in bacteria. Salmonella typhimurium (strains TA100, TA1535, and TA1537) were exposed in the absence of S9 metabolic activation to 0, 0.610, 1.22, 2.44, 4.88, 9.77, 19.5, or 39.1 ug/plate. Alternate concentrations of the test material, 0, 9.77, 19.5, 39.1, 78.1, 156, 313, or 625 ug/plate, were used with S9 activation on S. typhimurium strains TA100, TA1535, and TA1537. Salmonella typhimurium strain TA98 and E. coli strain WP2 uvrA were exposed to 313, 625, 1250, 2500, or 5000 ug/plate in the absence of S9 metabolic activationin the presence of S9 activation, they were exposed to concentrations of 39.1, 78.1, 156, 313, 1250, or 2500 ug/plate of the test compound. 2-Ethylhexyl methacrylate did not induce gene mutations in the bacterial strains.2-Ethylhexyl methacrylate was tested for potential to induce chromosomal aberrations in Chinese hamster lung (CHL) cells in the presence and absence of S9 metabolic activation. CHL cells were exposed without metabolic activation to concentrations of 0, 10, 20, 40, or 80 ug/ml for 24 or 48 hours continuous treatment, or 6 hours short-term treatment. An additional short term (6 hr) test was conducted with concentrations of 0, 0, 625, 1250, 2500, or 5000 ug/ml with S9 metabolic activation mix. Longer term exposures with metabolic activation were not reported. The test chemical did not induce any chromosomal aberrations under the conditions of this test. |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ Five male volunteers who developed contact dermatitis to acrylic based adhesive were tested for cross sensitization with other acrylic derivatives. ... None of the subjects had a reaction to methylmethacrylate or 2-ethyl-hexylmethacrylate. 2-Ethyl-hexyl-acrylate induced allergies in all subjects. Two subjects reacted to hydroxy-propyl-methacrylatethe other three subjects were not tested. There were broad cross reaction patterns within the acrylate esters up to octyl-acrylate. There was no reaction to N-tert-butyl-maleamic-acid (NTBM) or acrylonitrile./SIGNS AND SYMPTOMS/ Skin and/or eye exposure can cause redness. /From table/ |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Acute Exposure/ Methacrylic acid administered IV increased respiratory rate, decreased heart rate, and produced electrocardiogram changes in anesthetized dogs. Methacrylic acid, methyl, n-propyl, n-butyl, isobutyl, and hydroxyethyl methacrylates produced a biphasic response, an abrupt fall in blood pressure followed by a secondary rise. 2-Ethylhexyl, isodecyl, lauryl, and tert-butylaminoethyl methacrylates produced only a hypotensive effect. Dimethylaminoethylmethacrylate produced only a hypertensive effect./LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ 2-Ethylhexyl methacrylate was studied for oral toxicity in rats in an OECD combined repeat dose and reproductive/developmental toxicity screening test at doses of 0, 30, 100, 300 and 1000 mg/kg/day for 49 days. For the males, the absolute kidney weights and the relative pituitary, liver and kidney weights were increased in the 300 and 1000 mg/kg groups. Suppression of body weight gain and decreased food consumption, RBC, hemoglobin, hematocrit, WBC and total protein, and increased GOT, GPT, A/G ratio, BUN and Cl, as well as focal necrosis in the liver and decrease of extramedullary hematopoiesis in the spleen were seen in the 1000 mg/kg group. For the females, the relative kidney weights were increased in the 100 mg/kg or more groups. Suppression of body weight gain during the pre-mating, pregnancy and lactation periods, decrease in food consumption during the pre-mating period, atrophy of the thymus, the increased absolute kidney, relative thyroid and liver weights, and decrease of extramedullary hematopoiesis in the spleen and focal malacia in the medulla oblongata were seen in the 1000 mg/kg group, one animal of which died. The NOELs for repeat dose toxicity are considered to be 100 mg/kg for males, and 30 mg/kg for females./LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ 2-Ethylhexyl methacrylate was studied for oral toxicity in rats in an OECD combined repeat dose and reproductive/developmental toxicity screening test at doses of 0, 30, 100, 300 and 1000 mg/kg/day for 49 days. With regard to reproductive/developmental toxicity, three of the seven females lost their pups in the 1000 mg/kg group. Numbers of corpora lutea and implantation scars were decreased in the 1000 mg/kg group. The NOELs for reproductive performance are considered to be 1000 mg/kg for males, and 300 mg/kg for females. With regard to pups, decreased numbers of live pups born were seen in the 300 and 1000 mg/kg groups. Decreased birth, live birth and viability indices, and decreased body weights of both sexes on day 0 and day 4 after birth were seen in the 1000 mg/kg group. The NOEL for pup development is considered to be 100 mg/kg./LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Animal studies using rats revealed that some acrylates and methacrylates are embryotoxic. The doses of monomers used in the animal studies, however, were much higher than concentrations likely encountered by workers. /Acrylates and Methacrylates/For more Non-Human Toxicity Excerpts (Complete) data for 2-ETHYLHEXYL METHACRYLATE (7 total), please visit the HSDB record page. |
| Antidote and Emergency Treatment | 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/ |
| Non-Human Toxicity Values | LD50 Rat oral >2,000 mg/kgLD50 Mouse ip 2.614 ml/kg |
| F | 19 |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3334 |
| Zollcode | 29161290 |
| RTECS-Nr. | OZ4630000 |
| R-Sätze (R) | 36/37/38-43-52/53 |
| Toxizität | LD50 orally in Rabbit: > 2000 mg/kg |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-37/39-24-61-36/37-28 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 688-84-6(Hazardous Substances Data) |
| Gefahrenklasse | Aquatic Chronic 3Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3 |
| Selbstentzündungstemperatur | 380 °C |
Anwendungen & Verwendung
Beschreibung
2-Ethylhexyl methacrylate is an ester of Methacrylic acid used as a raw material component in synthesizing polymers. It is a monofunctional monomer consisting of a methacrylate group with a characteristic high reactivity and a cyclic hydrophobic group and could form homopolymers and copolymers. 2-Ethylhexyl methacrylate could be used as a monomer for polymers in latex paints, lacquers, polishes, coating resins for food contact, and viscosity index improvers.
Verwenden
2-Ethylhexyl Methacrylate(2-EHMA) can be used as a release coating composition,it is also used in Coating resins, Plastic improvers, Reactive Systems, Textile treating agents, Fabric auxiliary, Paper and water, Lubricating oil additives, Adhesives, and also Dental materials.