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96-33-3

96-33-3 Structure

96-33-3 Structure
IdentificationMore
[Name]

Methyl acrylate
[CAS]

96-33-3
[Synonyms]

2-PROPENOIC ACID METHYL ESTER
ACRYLIC ACID METHYL ESTER
AKOS BBS-00004387
MA
METHYL 2-PROPENOATE
METHYL ACRYLATE
METHYL PROPENOATE
[sri773]methylacrylate,monomer
2-Propenoicacidmethylesetr
Acrylate de methyle
acrylatedemethyle
acrylatedemethyle(french)
Acrylsaeuremethylester
CH2=CHCOOCH3
Curithane 103
curithane103
Methacrylate
Methoxycarbonylethylene
Methyl acrylate, inhibited
Methyl ester acrylic acid
[EINECS(EC#)]

202-500-6
[Molecular Formula]

C4H6O2
[MDL Number]

MFCD00008627
[Molecular Weight]

86.09
[MOL File]

96-33-3.mol
Chemical PropertiesBack Directory
[Appearance]

Methyl acrylate is a clear, colorless liquid with a sharp, fruity odor.
[Appearance]

colourless liquid
[mp ]

-75 °C
[Melting point ]

-75 °C (lit.)
[Boiling point ]

80 °C (lit.)
[bp ]

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
[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.
[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).
[Uses]

Acrylic polymers, amphoteric surfactants, vitamin B 1, chemical intermediate.
[CAS DataBase Reference]

96-33-3(CAS DataBase Reference)
[NIST Chemistry Reference]

2-Propenoic acid, methyl ester(96-33-3)
[IARC]

2B (Vol. 39, Sup 7, 71, 122) 2019
[EPA Substance Registry System]

96-33-3(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

F,Xn
[Risk Statements ]

R11:Highly Flammable.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
R43:May cause sensitization by skin contact.
[Safety Statements ]

S9:Keep container in a well-ventilated place .
S25:Avoid contact with eyes .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S33:Take precautionary measures against static discharges .
S36/37:Wear suitable protective clothing and gloves .
S43:In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add-Never use water) .
[RIDADR ]

UN 1919 3/PG 2
[WGK Germany ]

2
[RTECS ]

AT2800000
[F ]

8
[Autoignition Temperature]

874 °F
[TSCA ]

Yes
[HazardClass ]

3
[PackingGroup ]

II
[HS Code ]

29161210
[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.
[Hazardous Substances Data]

96-33-3(Hazardous Substances Data)
[Toxicity]

LD50 orally in rats: 0.3 g/kg (Smyth, Carpenter)
Raw materials And Preparation ProductsBack Directory
【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-->FEMA 2763-->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-->Isothiazolinones-->Leather coating agent of filling acrylic resin-->Disperse Brown 19-->4-Dodecanolide-->Methyl 1-methyl-4-oxopiperidine-3-carboxylate-->1-Phenethyl-4-piperidone
Hazard InformationBack Directory
[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.
[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.
[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.
[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.
[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.
[First aid]

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, 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 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy.
[Shipping]

UN1919 Methyl acrylate, stabilized, Hazard Class: 3; Labels: 3-Flammable liquid.
[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.
[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
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.
[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
[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).
[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:
manufacture of methyI acrylate
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).
[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.
[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]

It is an acute toxin with an LD50 (rats, oral) of 300 mg/kg and a TLV of 10 ppm.
[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 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.
[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.
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

methyl acrylate(96-33-3).msds
Spectrum DetailBack Directory
[Spectrum Detail]

Methyl acrylate(96-33-3) MS
Methyl acrylate(96-33-3) IR1
Methyl acrylate(96-33-3) 13C NMR
Methyl acrylate(96-33-3) Raman
Methyl acrylate(96-33-3) 1H NMR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Methyl acrylate, stabilized, 99%(96-33-3)
[Alfa Aesar]

Methyl acrylate, 99%, stab. with ca 15ppm 4-methoxyphenol(96-33-3)
[Sigma Aldrich]

96-33-3(sigmaaldrich)
[TCI AMERICA]

Methyl Acrylate  (stabilized with MEHQ),>99.0%(GC)(96-33-3)
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