Methyl acrylate CAS 96-33-3
Introduction：Basic information about Methyl acrylate CAS 96-33-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Methyl acrylate Basic information
| Product Name: | Methyl acrylate |
| Synonyms: | Acrylate de methyle;acrylatedemethyle;ACRYLIC ACID METHYL ESTER;AKOS BBS-00004387;METHYL PROPENOATE;METHYL ACRYLATE;METHYL 2-PROPENOATE;2-PROPENOIC ACID METHYL ESTER |
| CAS: | 96-33-3 |
| MF: | C4H6O2 |
| MW: | 86.09 |
| EINECS: | 202-500-6 |
| Product Categories: | ester series;Alpha Sort;Analytical Standards;Chemical Class;EstersOther Lipid Related Products;Fatty AcidsVolatiles/ Semivolatiles;AcrylateCarbonyl Compounds;Acrylic Monomers;Lipid Analytical Standards;M;MAlphabetic;META - METHGasoline, Diesel,&Petroleum;Olefins;Substance classes;C2 to C5;Esters;Monomers;Carbonyl Compounds;96-33-3 |
| Mol File: | 96-33-3.mol |
Methyl acrylate Chemical Properties
| Melting point | -75 °C (lit.) |
| Boiling point | 80 °C (lit.) |
| density | 0.956 g/mL at 25 °C (lit.) |
| vapor density | 3 (vs air) |
| vapor pressure | 67.5 mm Hg ( 20 °C) |
| refractive index | n |
| Fp | 26.6 °F |
| storage temp. | 2-8°C |
| solubility | 60g/l |
| form | Liquid |
| color | Clear |
| Odor | acrid odor |
| PH | 7 (20°C) |
| Odor Threshold | 0.0035ppm |
| explosive limit | 2.8%(V) |
| Water Solubility | 60 g/L (20 ºC) |
| Sensitive | Light Sensitive |
| Merck | 14,6011 |
| BRN | 605396 |
| Henry's Law Constant | (x 10-4 atm?m3/mol):1.3 at 20 °C (approximate - calculated from water solubility and vapor pressure) |
| Dielectric constant | 7.1200000000000001 |
| Exposure limits | TLV-TWA 10 ppm (～35 mg/m3) (ACGIHand MSHA), TLV-TWA skin 10 ppm(～35 mg/m3) (OSHA); IDLH 1000 ppm(NIOSH). |
| Stability: | Stable. Incompatible with bases, acids, oxidizing agents, peroxides. May polymerize on exposure to light. Highly flammable. Commercial product may be inhibited by the presence of hydroquinone monomethyl ether. |
| Major Application | environmental petroleum |
| InChI | 1S/C4H6O2/c1-3-4(5)6-2/h3H,1H2,2H3 |
| InChIKey | BAPJBEWLBFYGME-UHFFFAOYSA-N |
| SMILES | COC(=O)C=C |
| LogP | 0.739 at 25℃ |
| Surface tension | 26.96mN/m at 293.15K |
| CAS DataBase Reference | 96-33-3(CAS DataBase Reference) |
| IARC | 2B (Vol. 39, Sup 7, 71, 122) 2019 |
| NIST Chemistry Reference | 2-Propenoic acid, methyl ester(96-33-3) |
| EPA Substance Registry System | Methyl acrylate (96-33-3) |
| ECETOC JACC REPORT | Methyl acrylate (96-33-3) |
Safety Information
| Hazard Codes | F,Xn |
| Risk Statements | 11-20/21/22-36/37/38-43 |
| Safety Statements | 9-25-26-33-36/37-43-43A |
| RIDADR | UN 1919 3/PG 2 |
| OEB | A |
| OEL | TWA: 10 ppm (35 mg/m3) [skin] |
| WGK Germany | 2 |
| RTECS | AT2800000 |
| F | 8 |
| Autoignition Temperature | 874 °F |
| TSCA | TSCA listed |
| HS Code | 2916 12 00 |
| HazardClass | 3 |
| PackingGroup | II |
| Storage Class | 3 - Flammable liquids |
| Hazard Classifications | Acute Tox. 3 Inhalation Acute Tox. 4 Dermal Acute Tox. 4 Oral Aquatic Chronic 3 Eye Irrit. 2 Flam. Liq. 2 Skin Irrit. 2 Skin Sens. 1 STOT SE 3 |
| Hazardous Substances Data | 96-33-3(Hazardous Substances Data) |
| Toxicity | LD50 orally in rats: 0.3 g/kg (Smyth, Carpenter) |
| IDLA | 250 ppm |
| Description | Methyl acrylate is an organic compound with the formula CH2CHCO2CH3. It is the methyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced to make acrylate fiber, which is used to weave synthetic carpets. It is also a reagent in the synthesis of various pharmaceutical intermediates. |
| Chemical Properties | Methyl acrylate is a clear, colorless, corrosive liquid with a sharp, fruity odor. It is soluble in water and completely miscible with most organic solvents. Methyl acrylate has a variety of industrial uses. the more important commercial uses of methyl acrylate include the preparation of thermoplastic coatings, use in the manufacture of acrylic and modacrylic fibers. In the fiber application, methyl acrylate is used as a comonomer with acrylonitrile. These acrylic fibers usually contain about 85% acrylonitrile and are used to fabricate clothing, blankets, carpets, and curtains. Other uses of methyl acrylate include coatings, adhesives, textile backcoatings, elastomers, plastics, and it is also found in ionic exchange resins, barrier film resins, antioxidant intermediates and acrylic fibers. |
| Physical properties | Clear, colorless, flammable liquid with a heavy, sweet, pungent odor. An odor thresholdconcentration of 3.5 ppbv was reported by Nagata and Takeuchi (1990). |
| Uses | Methyl acrylate is a monomer used in the manufacture of acrylic fibers, plastic films, textiles, papercoatings, and other acrylate ester resins. It is also used in amphoteric surfactants. |
| Definition | methacrylate: A salt or ester ofmethacrylic acid (2-methylpropenoicacid). |
| Production Methods | Methyl acrylate is manufactured via a reaction of nickelcarbonyl and acetylene with methanol in the presence ofan acid; more commonly, however, it is manufacturedvia oxidation of propylene to acrolein and then toacrylic acid. The acid is reacted with methanol to yieldthe ester. |
| Preparation | Acrylate esters can be produced in a number of ways. The most commonly used method, developed in 1970, involves a propylene oxidation process. The reaction occurs initially with the oxidation of propylene to acrolein, which in turn is oxidized to acrylic acid. Once the acrylic acid is formed, it is reacted with methanol which causes the formation of the methyl acrylate. This reaction is shown as follows: An older method, the Reppe process, involves reacting acetylene with nickel carbonyl and methyl alcohol in the presence of an acid to produce methyl acrylate. More recent methods for producing acrylate esters involve the use of organic carbonates as esterifying agents or isolating 2-halo- 1-alkenes from hydrocarbon feedstocks to produce the acrylate esters (Haggin, 1985). |
| General Description | Colorless volatile liquid with an acrid odor. Flash point 27°F. Vapors may irritate the eyes and respiratory system. Highly toxic by inhalation, ingestion and skin absorption. Less dense than water (0.957 gm / cm3) and slightly soluble in water, hence floats on water. Vapors heavier than air. |
| Air & Water Reactions | Highly flammable. Forms peroxides when exposed to air that may initiate spontaneous, exothermic polymerization. Peroxide formation usually proceeds slowly. Slightly soluble in water. |
| Reactivity Profile | METHYL ACRYLATE ignites readily when exposed to heat, flame or sparks. Offers a dangerous fire and explosion hazard. Reacts vigorously with strong oxidizing materials. Forms peroxides when exposed to air that may initiate spontaneous exothermic polymerization. Peroxide formation usually proceeds slowly. Added inhibitor retards polymerization. If the inhibitor is consumed during long storage, explosive polymerization may occur [MCA Case History No. 2033]. Also subject to strongly exothermic polymerization if heated for prolonged periods or contaminated. |
| Hazard | Flammable, dangerous fire and explosionrisk. Toxic by inhalation, ingestion, and skin absorption; irritant to skin, eyes and upper respiratory tractirritant; eye damage. Questionable carcinogen. |
| Health Hazard | The liquid is a strong irritant, and prolongedcontact with the eyes or skin may causesevere damage. Inhalation of its vapors cancause lacrimation, irritation of respiratorytract, lethargy, and at high concentrations,convulsions. One-hour exposure to a concen tration of 700–750 ppm in air caused deathto rabbits. The oral toxicity of methyl acry late in animals varied from low to moderate,depending on species, the LD50 values ranging between 250 and 850 mg/kg. The liquidmay be absorbed through the skin, producingmild toxic effects. |
| Fire Hazard | Flammable liquid; flash point (closed cup)-4°C (25°F), (open cup) -3°C (27°F); vaporpressure 68 torr at 20°C (68°F); vapor density3.0 (air = 1); the vapor is heavier than air andcan travel a considerable distance to a sourceof ignition and flashback; autoignition tem perature not established; fire-extinguishingagent: dry chemical, CO2, or “alcohol” foam;use water to keep the fire-exposed containerscool and to flush or dilute any spill; the vaporsmay polymerize and block the vents. The vapors of methyl acrylate form explo sive mixtures with air, over a relatively widerange; the LEL and UEL values are 2.8 and25.0% by volume in air, respectively. Methylacrylate undergoes self-polymerization at25°C (77°F). The polymerization reactionproceeds with evolution of heat and theincreased pressure can cause rupture ofclosed containers. The reaction rate is accelerated by heat, light, or peroxides. Vigorousto violent reaction may occur when mixedwith strong oxidizers (especially nitrates andperoxides) and strong alkalie. |
| Safety Profile | Poison by ingestion and intraperitoneal routes. Moderately toxic by skin contact. Mddly toxic by inhalation. Human systemic effects by inhalation: olfaction effects, eye effects, and respiratory effects. A skin and eye irritant. Mutation data reported. Chronic exposure has produced injury to lungs, liver, and kidneys in experimental animals. Questionable carcinogen. Dangerously flammable when exposed to heat, flame, or oxidzers. Dangerous explosion hazard in the form of vapor when exposed to heat, sparks, or flame. Can react vigorously with oxidzing materials. A storage hazard; it forms peroxides, which may initiate exothermic polymerization. To fight fire, use foam, COa, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS. |
| Safety | It is an acute toxin with an LD50 (rats, oral) of 300 mg/kg and a TLV of 10 ppm. |
| Potential Exposure | Methyl acrylate is used in productionof acrylates, copolymers, barrier resins; and surfactants forshampoos; as a monomer in the manufacture of polymersfor plastic films, textiles, paper, and leather coatingresins. It is also used as a pesticide intermediate and inpharmaceutical manufacture. |
| First aid | If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. Medical observation is recommended for 2448 h after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a corticosteroid spray. |
| Carcinogenicity | Methyl acrylate was not shown to be carcinogenic in male and female rats in a lifetime inhalation study. Not listed by ACGIH, California Proposition 65, IARC, NTP, or OSHA. |
| Environmental fate | Photolytic. Polymerizes on standing and is accelerated by heat, light, and peroxides (Windholzet al., 1983). Methyl acrylate reacts with OH radicals in the atmosphere (296 K) and aqueoussolution at rates of 3.04 x 10-12 and 2.80 x 10-12 cm3/molecule?sec, respectively (Wallington et al.,1988b). Chemical/Physical. Begins to polymerize at 80.2 °C (Weast, 1986). Slowly hydrolyzes in waterforming methyl alcohol and acrylic acid (Morrison and Boyd, 1971). Based on a hydrolysis rateconstant of 0.0779/M?h at pH 9 at 25 °C, an estimated half-life of 2.8 yr at pH 7 was reported(Roy, 1972). The reported rate constant for the reaction of methacrylonitrile with ozone in the gasphase is 2.91 x 10-18 cm3 mol/sec (Munshi et al., 1989a). |
| storage | Methyl acrylate is stored in a flammable materials storage room or cabinet below 20°C (68°F), separated from oxidizing substances. It is inhibited with 200 ppm ofhydroquinone monomethyl ether to preventself-polymerization. It is shipped in bottles,cans, drums, or tank cars. |
| Shipping | UN1919 Methyl acrylate, stabilized, HazardClass: 3; Labels: 3-Flammable liquid. |
| Purification Methods | Wash the ester repeatedly with aqueous NaOH until free from inhibitors (such as hydroquinone), then wash it with distilled water, dry (CaCl2) and fractionally distil it under reduced pressure in an all-glass apparatus. Seal it under nitrogen and store it at 0o in the dark. [Bamford & Han J Chem Soc, Faraday Trans 1 78 855 1982, Beilstein 2 IV 1457.] |
| Toxicity evaluation | Methyl acrylate (MA) is moderately toxic to fish (LC50 1.1 - 7.5 mg/l), crustaceans (LC50/EC50 0.31 - 2.6 mg/l) and algae(EC50 6.9 - 15.0 mg/l). In Selenastrum capricornutum, MA is algistatic at a concentration of 19 mg/l.It is of low acute toxicity to bacteria and protozoa. |
| Incompatibilities | Forms explosive mixture in air.Incompatible with nitrates, oxidizers, such as peroxides,strong alkalis. Polymerizes easily from heat, light, peroxides; usually contains an inhibitor, such as hydroquinone. |
| Toxics Screening Level | The current initial threshold screening level (ITSL) for methyl acrylate is 70 μg/m3 based on anannual averaging time. |
| Waste Disposal | Dissolve or mix the materialwith a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal,state, and local environmental regulations must beobserved. Consult with environmental regulatory agenciesfor guidance on acceptable disposal practices. Generatorsof waste containing this contaminant (≥100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal |
Methyl acrylate Preparation Products And Raw materials
| Raw materials | Methanol-->Maleic anhydride-->Propylene oxide-->Glycerol-->Acrylic acid-->Poly(acrylic acid)-->Acrylamide-->Castor oil-->Acrolein-->Benzoic acid-->Propylene glycol-->PASSION FLOWER OIL-->Pentaerythritol-->Polyethylene-polypropylene glycol-->Fatty acids, C8-10, triesters with trimethylolpropane-->ketene-->RAPESEED OIL |
| Preparation Products | 2-Phosphonobutane-1,2,4-tricarboxylic acid-->Adhesive for nonwoven fabric-->(E)-METHYL 3-(4-BROMOPHENYL)ACRYLATE-->BT modified acrylic resin binder series-->CSF series modified sacrylic binder-->1-Methyl-4-piperidinol hydrochloride-->oil-proof, water-proof finishing agent-->weather-proof acrylic binder series-->AC anti-fungus leather finishing agent-->Undecan-4-olide-->Tetradecanal-->2-Ethylhexyl acrylate-->4-Chloro-1-methylpiperidine hydrochloride-->efficient polymer catalyst for acrylation-synthesis and characterigation of polyamide containing supernucleophilic reagent-->acrylate resin emulsion s-1-->3-DIMETHYLAMINOPROPIONIC ACID-->Methyl 4-oxotetrahydrothiophene-3-carboxylate-->warp dressing agent MVAc-->laurylamide propionate JHZ-101-->N-hydroxyethyl-N-hydroxyalkyl-β-alanine-->acrylate resin emulsion new type-->Pioglitazone-->EPROSARTAN-->laurylamide carboxyamine propionate JHZ-102-->softener D3-->Methyl 3-methylthiopropionate-->acrylate resin emulsion M-1-->REMIFENTANIL-->chelating resin containing acrylic acid amino acetic group-->METHYL 4-(AMINOMETHYL)CYCLOHEXANECARBOXYLATE-->3-dodecylaminopropionic acid-->1,3-Dimethylpiperidin-4-one-->AMBERLITE XAD-16-->Nitrocellulose enamel-->5-Chloro-2-methyl-4-isothiazolin-3-one-->Leather coating agent of filling acrylic resin-->Disperse Brown 19-->4-Dodecanolide-->Methyl 1-methyl-4-oxopiperidine-3-carboxylate-->1-Phenethyl-4-piperidone |
