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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 | Hazard Symbols | F, Xn | |
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, 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. |