96-33-3 Usage
Description
Methyl acrylate, with the chemical formula CH2=CHCO2CH3, is an organic compound that is the methyl ester of acrylic acid. It is a colorless liquid with a distinctive acrid odor and is highly toxic by inhalation, ingestion, and skin absorption. Methyl acrylate is soluble in water and completely miscible with most organic solvents. It is mainly produced for the manufacture of acrylate fibers and as a reagent in the synthesis of various pharmaceutical intermediates.
Uses
Used in Nail Lacquers:
Methyl acrylate is used in some nail lacquers for its ability to form a hard, durable film that provides a glossy finish and long-lasting wear.
Used in Fiber Production:
Methyl acrylate is used as a comonomer with acrylonitrile in the production of acrylic and modacrylic fibers. These fibers, which usually contain about 85% acrylonitrile, are used to fabricate clothing, blankets, carpets, and curtains.
Used in Coatings:
Methyl acrylate is used in the preparation of thermoplastic coatings, providing properties such as adhesion, flexibility, and resistance to chemicals and weathering.
Used in Chemical Synthesis:
Methyl acrylate serves as a chemical intermediate in the synthesis of various compounds, including acrylic polymers, amphoteric surfactants, and vitamin B1.
Used in Plastic Films and Textiles:
Methyl acrylate is a monomer used in the manufacture of plastic films, textiles, and paper coatings, contributing to their strength, durability, and versatility.
Used in Amphoteric Surfactants:
Methyl acrylate is also used in the production of amphoteric surfactants, which are important in the formulation of personal care and cleaning products due to their mildness and foaming properties.
Used in Elastomers and Plastics:
Methyl acrylate is utilized in the production of elastomers and plastics, enhancing their elasticity, toughness, and resistance to deformation.
Used in Ionic Exchange Resins:
Methyl acrylate is found in ionic exchange resins, which are used in water treatment, food processing, and various industrial applications to remove ions from solutions.
Used in Barrier Film Resins:
Methyl acrylate is used in the production of barrier film resins, which are employed in the creation of films with improved barrier properties for packaging and other applications.
Used in Antioxidant Intermediates:
Methyl acrylate is also used as an intermediate in the synthesis of antioxidants, which are important additives in various industries to prevent oxidation and degradation of materials.
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).
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.
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
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.
Flammability and Explosibility
Flammable
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 .
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 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, 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.]
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.
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
Check Digit Verification of cas no
The CAS Registry Mumber 96-33-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 6 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 96-33:
(4*9)+(3*6)+(2*3)+(1*3)=63
63 % 10 = 3
So 96-33-3 is a valid CAS Registry Number.
InChI:InChI=1/C4H6O2/c1-3-4(5)6-2/h3H,1H2,2H3
96-33-3Relevant articles and documents
Scalable Total Synthesis of (-)-Triptonide: Serendipitous Discovery of a Visible-Light-Promoted Olefin Coupling Initiated by Metal-Catalyzed Hydrogen Atom Transfer (MHAT)
Fang, Xianhe,Zhang, Nan,Chen, Si-Cong,Luo, Tuoping
supporting information, p. 2292 - 2300 (2022/02/09)
An efficient and scalable total synthesis of (-)-triptonide is accomplished based on a metal-catalyzed hydrogen atom transfer (MHAT)-initiated radical cyclization. During the optimization of the key step, we discovered that blue LEDs significantly promoted the efficiency of reaction initiated by Co(TPP)-catalyzed MHAT. Further exploration and optimization of this catalytic system led to development of a dehydrogenative MHAT-initiated Giese reaction.
Method for preparing methyl acrylate from methyl acetate
-
Paragraph 0138-0168, (2021/04/28)
The invention provides a method for preparing methyl acrylate from methyl acetate, which comprises the following steps: in the presence of a solid base catalyst, methyl acetate reacts with an aldehyde source to obtain methyl acrylate, and the solid base catalyst comprises the following components in parts by mass: a) a catalytic amount of alkali metal oxide; and b) 50 to 80 parts of a carrier; wherein the carrier is silicon dioxide of which the silicon hydroxyl density is 0.6-1.5 Si-OH/nm. The invention also provides a solid base catalyst, and an application and a preparation method thereof. The methyl acrylate synthesis route and the corresponding solid base catalyst have the advantages that the yield and selectivity are improved, and the catalytic activity can be maintained for a long time, so that the industrialization can be realized, and the problem that the production capacity of methyl acetate is greatly excessive is solved.
Phosphine-Catalyzed Cascade Annulation of MBH Carbonates and Diazenes: Synthesis of Hexahydrocyclopenta[c]pyrazole Derivatives
Guo, Hongchao,Li, Hongxiang,Liu, Hao,Shi, Wangyu,Wang, Chang,Wang, Wei,Wu, Yongjun
supporting information, p. 5571 - 5575 (2021/07/31)
A phosphine-catalyzed cascade annulation of Morita-Baylis-Hillman (MBH) carbonates and diazenes was achieved, giving tetrahydropyrazole-fused heterocycles bearing two five-membered rings in moderate to excellent yields. The reaction underwent an unprecedented reaction mode of MBH carbonates, in which two molecules of MBH carbonates were fully merged into the ring system.
This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.