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2-Hydroxyethylmethacrylat
HEMA · HYDROXYETHYL METHACRYLATE · GLYCOL METHACRYLATE · ETHYLENE GLYCOL METHACRYLATE · N5-Methyl-L-glutamine · 1,2-ETHANEDIOL MONO(2-METHYLPROPENOATE) · 2-methyl-2 · BisoMer HEMA
Identifikatoren & physikalische Daten
| CAS No. | 12676-48-1 |
|---|---|
| Summenformel | C6H10O3 |
| Durchschnittliche Molmasse | 130,14 g/mol |
| Monoisotopische Masse | 130,06299418 g/mol |
| SMILES | C=C(C)C(=O)OCCO |
| InChIKey | WOBHKFSMXKNTIM-UHFFFAOYSA-N |
| PubChem CID | 13360 |
| ChEMBL | CHEMBL1730239 |
| ChEBI | CHEBI:34288 |
| EC No. | 212-782-2 |
| DTXSID | DTXSID7022128 |
| Lokaler Name | 2-Hydroxyethylmethacrylat |
Chemische & physikalische Eigenschaften
| XLogP | 0,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 46,5 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 117 |
| Polymers | Plastics & Rubber -> (Meth)acrylates |
| Kosmetika | Cosmetic ingredients (HEMA) -> CIR (Cosmetic Ingredient Review) |
| LogP (Verteilungskoeffizient) | log Kow= 0.470.42 |
| Dichte | 1.034 @ 25 °C/4 °C1.07 g/cm³1.034 @25 °C1.073 g/mL at 25 °C(lit.) |
| Viscosity | 8.4 mm²/s at 20 °C |
| Color/Form | Clear mobile liquid |
| Löslichkeit | Miscible with water and soluble in common org solventsSolubility in water: miscibleChloroform, Methanol (Slightly) |
| Flammpunkt | 97 °C (closed cup)97 °C c.c.207 °F |
| Siedepunkt | 67 °C @ 3.5 mm Hg250 °C (calculated)67 °C @760 [mm Hg]67 °C3.5 mm Hg(lit.) |
| Decomposition | When heated to decomp it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | FP: -12 °C |
| Dampfdichte | Relative vapor density (air = 1): 4.55 (vs air) |
| Dampfdruck | 0.01 mm Hg ( 25 °C) |
| Brechungsindex | n20/D 1.453(lit.) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | 13.83±0.10(Predicted) |
| Farbe | Clear |
| Geruch | Ester like |
| BRN | 1071583 |
| Henry-Konstante | 4.6×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Stabilität | Unstable - may polymerize in the absence of stabilizer. May be stabilized with, or contain small amounts of, diethylene glycol monomethacrylate, di(ethylene glycol)dimethacrylate, methacrylic acid. Incompatible with strong oxidizing agents, free radical initiators, peroxides, steel. Closed containers may explode if heated due to runaway polymer |
| Kosmetik-Inhaltsstoffe Funktionen | NAIL SCULPTING |
| InChI | 1S/C6H10O3/c1-5(2)6(8)9-4-3-7/h7H,1,3-4H2,2H3 |
| InChIKey | WOBHKFSMXKNTIM-UHFFFAOYSA-N |
| SMILES | CC(=C)C(=O)OCCO |
| LogP (Verteilungskoeffizient) | 0.42 at 25℃ |
| CAS Datenbank | 868-77-9(CAS DataBase Reference) |
| NIST chemische Informationen | 2-Hydroxyethyl methacrylate(868-77-9) |
| EPA chemische Informationen | 2-Hydroxyethyl methacrylate (868-77-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315: Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.2% (3 of 1898) of reports.H315 (94.3%): Causes skin irritation [Warning Skin corrosion/irritation] |
|---|---|
| Regulatorische Informationen | Chemical: 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl 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/151242-Hydroxyethyl methacrylate: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester: Human health tier II assessment |
| Brandgefahren | Combustible. Above 97 °C explosive vapour/air mixtures may be formed. |
| Brandpotenzial | 30% GRADE (WITH XYLENE) IS FLAMMABLEMODERATE FIRE RISK. |
| Gefahrenübersicht | Allergic contact dermatitis reported in a laboratory technician and in the printing industryA skin and eye irritant[HSDB] Hydrolyzed forming methacrylic acid and ethylene glycolA mild skin and moderate eye irritantPossesses skin sensitizing properties with equivocal results in human patch testing[Reference #2] A skin and severe eye irritantMay cause skin sensitization[Alfa Aesar MSDS] |
| FDA-Anforderungen | Homopolymers and copolymers of 2-Hydroxyethyl methacrylate is an indirect food additive for use only as a component of adhesives. |
| EG-Einstufung | Symbol: XiR: 36/38-43S: (2)-26-28Note: D |
| Chemical Dangers | The substance will polymerize due to heating, on contact with peroxides, and under the influence of light. Heating may cause violent combustion or explosion. This produces acrid smoke. The substance may spontaneously polymerize if it is not stabilized. |
| Hazard Classes and Categories | Skin Irrit. 2 (94.3%)Eye irritation - category 2ASerious eye damage/eye irritation - Category 2ASerious eye damage/eye irritation - Category 2Skin corrosion/irritation - Category 2 |
| Skin, Eye, and Respiratory Irritations | Irritating to eyes and skin. |
| Brandbekämpfung | Use water spray, dry powder, alcohol-resistant foam. In case of fire: keep drums, etc., cool by spraying with water. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Refer for medical attention.First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. 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. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer immediately for medical attention. |
| Sichere Lagerung | Store only if stabilized. Keep in the dark. Cool. Ventilation along the floor. |
| Lagerbedingungen | Temp during storage must be kept low to minimize formation of peroxides and other oxidation products. ... Storage temp below 30 °C are recommended for the polyfunctional methacrylates. ... The methacrylate monomers should not be stored for longer than one year. Shorter storage times are recommended for the aminomethacrylates, ie, three months, and the polyfunctional methacrylates, ie, six months. Many of these cmpd are sensitive to UV light and should, therefore, be stored in the dark. The methacrylic esters may be stored in mild steel, stainless steel, or aluminum. /Methacrylic acid & derivatives/ |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Verschüttetes entsorgen | Personal protection: chemical protection suit and filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking liquid in covered containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Preventive Measures | ... Hazard is the generation of considerable exothermic heat in some of the reactions, so that high pressures & temp may develop. This danger ... should be borne in mind when designing plant. 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 irritants 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/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.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. |
| Eye Prevention | Wear safety spectacles or eye protection in combination with breathing protection. |
| Fire Prevention | NO open flames. Above 97 °C use a closed system and ventilation. |
| Inhalation Risk | No indication can be given about the rate at which a harmful concentration of this substance in the air is reached. |
| Skin Prevention | Protective gloves. Protective clothing. |
| Exposure Prevention | PREVENT GENERATION OF MISTS! |
| Ökotoxizitätswerte | LC50 Pimephales promelas (fathead minnows) 0.99 g/l/96 hr (95% confidence limit 0.90-1.1 g/l)age 30 days old, water hardness 45.6 mg/l calcium carbonate, temp 24.9 °C, pH 7.66, dissolved oxygen 7.1 mg/l, alkalinity 44.4 mg/l (CaCO3), Tank vol: 2.0 l, additions: 18 vol/day (flow-through bioassay) |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 43(SRC), determined from a log Kow of 0.47(2) and a regression-derived equation(3), indicates that 2-hydroxyethyl methacrylate is expected to have very high mobility in soil(SRC). Volatilization of 2-hydroxyethyl methacrylate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.6X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). 2-Hydroxyethyl methacrylate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.126 mm Hg(5). Screening tests indicate that 2-hydroxyethyl methacrylate is readily biodegradableit reached 92-100% of its theoretical BOD in 2 weeks using an activated sludge inoculum(6).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 43(SRC), determined from a log Kow of 0.47(2) and a regression-derived equation(3), indicates that 2-hydroxyethyl methacrylate is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.6X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 1.3(SRC), from the log Kow(2), suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis of 2-hydroxyethyl methacrylate may be a significant process under basic conditions based upon a hydrolytic half-life of 4 hours at pH 11 for the structurally similar butyl acrylate(6)half-lives for butyl acrylate at pH 7, 8, and 9 were 4 years, 150 days, and 15 days(SRC), respectively, based upon a hydrolytic rate constant of 0.053 L/mole-sec(8). Screening tests indicate that 2-hydroxyethyl methacrylate is readily biodegradableit reached 92-100% of its theoretical BOD in 2 weeks using an activated sludge inoculum(7).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-hydroxyethyl methacrylate, which has a vapor pressure of 0.126 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-hydroxyethyl methacrylate 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 16 hours(SRC) from its estimated rate constant of 2.4X10-11 cu cm/molecule-sec at 25 °C(3). Because the structurally similar ethyl methacrylate does not absorb light in the environmental spectrum above 290 nm(4), direct photolysis of 2-hydroxyethyl methacrylate is not expected to occur(SRC). |
| Unerwünschte Wirkungen | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| Toxizitätsübersicht | Based on available data, the CIR Expert Panel concluded that...HEMA is safe as used in nail enhancement products when skin contact is avoided. Products containing these ingredients should be accompanied with directions to avoid skin contact, because of the sensitizing potential of Methacrylates.Safe for use in cosmetics, with qualifications |
| Signs and Symptoms | Cough. Sore throat.Redness.Sore throat. Aspiration hazard! |
| Soil Adsorption/Mobility | The Koc of 2-hydroxyethyl methacrylate is estimated as approximately 43(SRC), using a log Kow of 0.47(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2-hydroxyethyl methacrylate is expected to have very high mobility in soil. |
| Human Toxicity Excerpts | LAB TECHNICIAN DEVELOPED ALLERGIC CONTACT DERMATITIS ASSOC WITH NAUSEA, DIARRHEA, & PERSISTENT PARESTHESIA OF FINGERTIPS. HYDROXYETHYLMETHACRYLATE WAS DEMONSTRATED TO PASS THROUGH VINYL GLOVES.2-Hydroxy-ethyl methacrylate and di- and tetra-ethylene glycol dimethacrylates have produced contact sensitization in workers in the printing industry. |
| Artificial Pollution Sources | 2-Hydroxyethyl methacrylate's production and use in acrylic resins, enamels, and as a binder for non-woven fabrics(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | 2-Hydroxyethyl methacrylate, present at 100 mg/l, reached 92-100% of its theoretical BOD in 2 weeks using an activated sludge inoculum and the Japanese MITI test(1). |
| Environmental Bioconcentration | An estimated BCF of 1.3 was calculated for 2-hydroxyethyl methacrylate(SRC), using a log Kow of 0.47(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low. |
| Volatilization from Water/Soil | The Henry's Law constant for 2-hydroxyethyl methacrylate is estimated as 4.6X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-hydroxyethyl methacrylate is expected to be essentially nonvolatile from water surfaces(2) and from moist soil surfaces(SRC). 2-Hydroxyethyl methacrylate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.126 mm Hg(3). |
| Non-Human Toxicity Excerpts | TOXICOLOGICALLY, HYDROXYETHYL METHACRYLATE APPEARS ALMOST THREE TIMES AS TOXIC AS THE METHACRYLIC ETHYL ESTER.INTRACORNEAL IMPLANTS OF PLASTIC FOILS MADE WITH HYDROXYETHYLMETHACRYLATE OR HYDROXYETHYLACRYLATE PLUS ETHYLENEGLYCOL DIMETHACRYLATE IN RABBITS PRODUCED EDEMA, VASCULARIZATION, NECROSIS, & ULCERATION & EVEN CHANGES IN THE PLASTICS THEMSELVES. CAUSATIVE AGENT NOT IDENTIFIED.THE TOXICITY OF 6 ACRYLATES AND 6 METHACRYLATES, INCLUDING 2-HYDROXYETHYL METHACRYLATE, WAS DETERMINED IN RATS AND FISH. ALL THE ESTERS WERE LESS TOXIC THAN ACRYLAMIDE AND ACRYLONITRILE. METHACRYLATES WERE APPROXIMATELY 5-FOLD LESS TOXIC THAN ACRYLATES. FOR A GIVEN SERIES, TOXICITY DECREASED WITH INCREASING LENGTH OF THE CARBON CHAIN.METHACRYLIC ACID ADMIN IV INCR RESPIRATORY RATE, DECR HEART RATE, & 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.TWENTY-ONE DIFFERENT ACRYLATE & METHACRYLATE COMPOUNDS, INCLUDING 2-HYDROXYETHYL METHACRYLATE, WERE SCANNED FOR THEIR ABILITY TO INDUCE CONTACT SENSITIVITY, USING 5 DIFFERENT SENSITIZATION PROTOCOLS. CONTACT REACTIONS OF VARYING INTENSITIES WERE PRODUCED TO ALL THE MONO-, DI-, AND TRIACRYLATES TESTED. METHACRYLATES DID NOT SENSITIZE GUINEA PIGS. |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29161490 |
| RTECS-Nr. | OZ4725000 |
| R-Sätze (R) | 36/38-43-36/37/38 |
| Toxizität | LD50 orally in Rabbit: 5050 mg/kg LD50 dermal Rabbit > 3000 mg/kg |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36/37-28A-28 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 868-77-9(Hazardous Substances Data) |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2Skin Sens. 1 |
Anwendungen & Verwendung
Beschreibung
2-Hydroxyethyl methacrylate (HEMA) is a widely used monomer compound employed in the preparation of poly(2-hydroxyethyl methacrylate) (PHEMA) and its derivatives. PHEMA is a favourable biomaterial primarily utilised in the production of hydrogel medical materials. HEMA is a raw material for contact lenses, paints, adhesives, resin modifiers, photosensitive resins, paper processing agents, and similar products.
Verwenden
2-Hydroxyethyl methacrylate is used for preparation of hydrophilic polymers for biomedical devices.