Methyl acrylate

Product Name: Methyl acrylate

Synonyms: Trandolaprilat 2-Benzyl Ester 1’[sri773]methylacrylate,monomer;2-Propenoicacidmethylesetr;Acrylate de methyle;acrylatedemethyle;propenoicacidmethylester;METHYL PROPENOATE;METHYL ACRYLATE

CAS: 96-33-3

MF: C4H6O2

MW: 86.09

EINECS: 202-500-6

Product Categories: Alpha Sort;Analytical Standards;Chemical Class;EstersOther Lipid Related Products;Fatty AcidsVolatiles/ Semivolatiles;Lipid Analytical Standards;M;MAlphabetic;META - METHGasoline, Diesel,&Petroleum;Olefins;Substance classes;AcrylateCarbonyl Compounds;Acrylic Monomers;C2 to C5;Esters;Monomers;Carbonyl Compounds;ester series

Mol File: 96-33-3.mol

Methyl acrylate Structure

Methyl acrylate Chemical Properties

Melting point -75 °C

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 n20/D 1.402(lit.)

Fp 26.6 °F

storage temp. Refrigerator (+4°C) + Flammables area

solubility 60g/l

form Liquid

color Clear

explosive limit 2.8%(V)

Odor Threshold 0.0035ppm

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)

Exposure limits TLV-TWA 10 ppm (～35 mg/m3) (ACGIH and 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.

CAS DataBase Reference 96-33-3(CAS DataBase Reference)

NIST Chemistry Reference 2-Propenoic acid, methyl ester(96-33-3)

EPA Substance Registry System 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

WGK Germany 2

RTECS AT2800000

F 8

Autoignition Temperature 874 °F

TSCA Yes

HS Code 2916 12 00

HazardClass 3

PackingGroup II

Hazardous Substances Data 96-33-3(Hazardous Substances Data)

Toxicity LD50 orally in rats: 0.3 g/kg (Smyth, Carpenter)

MSDS Information

Provider Language

ACROS English

SigmaAldrich English

ALFA English

Methyl acrylate Usage And Synthesis

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 colourless liquid

Chemical Properties Methyl acrylate is a clear, colorless liquid with a sharp, fruity odor.

Physical properties Clear, colorless, flammable liquid with a heavy, sweet, pungent odor. An odor threshold concentration of 3.5 ppbv was reported by Nagata and Takeuchi (1990).

Uses Acrylic polymers, amphoteric surfactants, vitamin B 1, chemical intermediate.

Uses Methyl acrylate is a monomer used in themanufacture of plastic films, textiles, papercoatings, and other acrylate ester resins. It isalso used in amphoteric surfactants.

Definition methacrylate: A salt or ester ofmethacrylic acid (2-methylpropenoicacid).

Production Methods Methyl acrylate is manufactured via a reaction of nickel carbonyl and acetylene with methanol in the presence of an acid; more commonly, however, it is manufactured via oxidation of propylene to acrolein and then to acrylic acid. The acid is reacted with methanol to yield the ester.

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 explosion risk. Toxic by inhalation, ingestion, and skin absorption; irritant to skin, eyes and upper respiratory tract irritant; eye damage. Questionable carcinogen.

Health Hazard May irritate skin, eyes, respiratory system, and gastro- intestinal tract. Fumes cause tears.

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); vapor pressure 68 torr at 20°C (68°F); vapor density 3.0 (air = 1); the vapor is heavier than air and can travel a considerable distance to a source of ignition and flashback; autoignition tem perature not established; fire-extinguishing agent: dry chemical, CO2, or “alcohol” foam; use water to keep the fire-exposed containers cool and to flush or dilute any spill; the vapors may polymerize and block the vents.

The vapors of methyl acrylate form explo sive mixtures with air, over a relatively wide range; the LEL and UEL values are 2.8 and 25.0% by volume in air, respectively. Methyl acrylate undergoes self-polymerization at 25°C (77°F). The polymerization reaction proceeds with evolution of heat and the increased pressure can cause rupture of closed containers. The reaction rate is accelerated by heat, light, or peroxides. Vigorous to violent reaction may occur when mixed with strong oxidizers (especially nitrates and peroxides) 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 production of acrylates, copolymers, barrier resins; and surfactants for shampoos; as a monomer in the manufacture of polymers for plastic films, textiles, paper, and leather coating resins. It is also used as a pesticide intermediate and in pharmaceutical manufacture.

Carcinogenicity Methyl acrylate was not shown to be carcinogenic in male and female rats in a lifetime inhalation study .

Carcinogenicity 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 (Windholz et al., 1983). Methyl acrylate reacts with OH radicals in the atmosphere (296 K) and aqueous solution 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 water forming methyl alcohol and acrylic acid (Morrison and Boyd, 1971). Based on a hydrolysis rate constant 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 gas phase is 2.91 x 10-18 cm3 mol/sec (Munshi et al., 1989a).

storage Methyl acrylate is stored in a flammablematerials storage room or cabinet below20°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, Hazard Class: 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.]

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.

Waste Disposal Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal