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Methyl acrylate

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Name

Methyl acrylate

EINECS 202-500-6
CAS No. 96-33-3 Density 0.924 g/cm3
PSA 26.30000 LogP 0.34540
Solubility 60 g/L (20 °C) in water Melting Point -75 °C
Formula C4H6O2 Boiling Point 80.199 °C at 760 mmHg
Molecular Weight 86.0904 Flash Point 6.667 °C
Transport Information UN 1919 3/PG 2 Appearance colourless liquid
Safety 9-25-26-33-36/37-43-43A Risk Codes 11-20/21/22-36/37/38-43
Molecular Structure Molecular Structure of 96-33-3 (Methyl acrylate) Hazard Symbols FlammableF, HarmfulXn
Synonyms

Acrylicacid methyl ester (6CI,8CI);2-Propenoic acid methyl ester;Methoxycarbonylethylene;Methyl acrylic ester;Methylprop-2-enoate;Methyl propenoate;NSC 24146;Methyl Acrylate(MA);

Article Data 290

Methyl acrylate Specification

Methyl acrylate, also known as 2-Propenoic acid, methyl ester, is colourless, flammable, volatile liquid with pungent odor. It has lacrimation. It is 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.What's more, it is soluble in alcohol, ether, acetone and benzene, slightly soluble in water. Methyl acrylate may polymerize on exposure to light. So the commercial product may be inhibited by the presence of hydroquinone monomethyl ether. In addition, it is used primarily as a comonomer with acrylonitrile in the manufacture of acrylic and modacrylic fibers.

Preparation of Methyl acrylate:
Methyl acrylate can be obtained by acrylonitrile hydrolysis, the direct oxidation of propylene and Ketene.
1. Acrylonitrile hydrolysis: The acrylamide sulfate which is obtained by hydrolysis of raw material acrylonitrile in the presence of concentrated sulfuric acid reacts with methanol to get methyl acrylate. This method can consume acrylonitrile (98%) 860kg, methanol (95%) 960kg, sulfuric acid (93%) 2000kg per ton of methyl acrylate.
CH2=CHCN+H2SO4+H2O→ CH2=CHCONH2•H2SO4
CH2=CHCONH2•H2SO4+CH4OH→ CH2=CHCOOCH3+NH4HSO4
2. Direct oxidation of propylene: First, oxidize raw material propylene to acrolein, and then further oxidize to acrylic acid. The acrylic acid reacts with methanol to obtain methyl acrylate. This method can consume propylene (95%) 544kg per ton of methyl acrylate.
CH2=CHCH3+O2→ CH2=CHCHO+H2O
CH2=CHCHO+1/2O2→ CH2=CHCOOH
CH2=CHCOOH+CH3OH→ CH2=CHCOOCH3+H2O
3. From ketene: First, go through condensation of ketene and formaldehyde with boron trifluoride as a catalyst. And then use methanol quenching, while esterification is carried out to obtain methyl acrylate.

Uses of Methyl acrylate:
Methyl acrylate is an important organic synthetic monomer and raw material. It is the second monomer of polyacrylonitrile fibers (acrylic fibers), which can be used as plastics and adhesives. The latex copolymerized with butyl acrylate can greatly improve the quality of leather to make leather soft, light and wearproof. So it is widely used in leather industry and the pharmaceutical industry. Methyl acrylate also can be used as a co-polymer in the process of polymerization of polyanionic cellulose (PAC) polymers, to reduce the glass transition temperature of the PAC polymers. In addition, it is used for synthesis of resin, preparation of plastic and coating, and processing of leather, textile and paper, etc.

Safty information of Methyl acrylate:
Methyl acrylate is harmful by inhalation and if swallowed. It is irritating to eyes, respiratory system and skin that may cause sensitisation by skin contact. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Please take precautionary measures against static discharges. If you want to contact this product, you must wear suitable protective clothing and gloves and avoid contact with eyes. 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).

Other properties of Methyl acrylate are :
(1)ACD/LogP: 0.79; (2)ACD/LogD (pH 5.5): 0.788; (3)ACD/LogD (pH 7.4): 0.788; (4)ACD/BCF (pH 5.5): 2.339; (5)ACD/BCF (pH 7.4): 2.339; (6)ACD/KOC (pH 5.5): 63.939; (7)ACD/KOC (pH 7.4): 63.939; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 26.3 Å2; (11)Index of Refraction: 1.39; (12)Molar Refractivity: 22.081 cm3; (13)Molar Volume: 93.138 cm3; (14)Polarizability: 8.753×10-24 cm3; (15)Surface Tension: 23.482 dyne/cm; (16)Density: 0.924 g/cm3; (17)Flash Point: 6.667 °C; (18)Enthalpy of Vaporization: 32.096 kJ/mol; (19)Boiling Point: 80.199 °C at 760 mmHg; (20)Vapour Pressure: 86.281 mmHg at 25°C

Structure Descriptors:
1. Smiles:C(=O)(C=C)OC
2. InChI:InChI=1/C4H6O2/c1-3-4(5)6-2/h3H,1H2,2H3

Toxicity date of Methyl acrylate as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TCLo inhalation 75ppm (75ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 75, 1969.
mouse LC50 inhalation 12800mg/m3 (12800mg/m3)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 23(9), Pg. 55, 1979.
mouse LD50 intraperitoneal 254mg/kg (254mg/kg)   Journal of Dental Research. Vol. 51, Pg. 526, 1972.
mouse LD50 oral 827mg/kg (827mg/kg)   Toxicology Letters. Vol. 11, Pg. 125, 1982.
rabbit LCLo inhalation 2522ppm/1H (2522ppm) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Industrial Hygiene and Toxicology. Vol. 31, Pg. 317, 1949.
rabbit LD50 skin 1243mg/kg (1243mg/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 30, Pg. 63, 1948.
rabbit LDLo oral 280mg/kg (280mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: TREMOR
Journal of Industrial Hygiene and Toxicology. Vol. 31, Pg. 317, 1949.
rat LC50 inhalation 1350ppm/4H (1350ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
Journal of Toxicology and Environmental Health. Vol. 16, Pg. 811, 1985.
rat LD50 intraperitoneal 325mg/kg (325mg/kg)   Archives des Maladies Professionnelles de Medecine du Travail et de Securite Sociale. Vol. 36, Pg. 58, 1975.
rat LD50 oral 277mg/kg (277mg/kg)   Archives des Maladies Professionnelles de Medecine du Travail et de Securite Sociale. Vol. 36, Pg. 58, 1975.