Methyl acrylate
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| Names | |||
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| IUPAC name
Methyl prop-2-enoate[1]
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| Other names | |||
| Identifiers | |||
96-33-3  |
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| ChEMBL | ChEMBL9019 |
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| ChemSpider | 7022 |
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| Jmol 3D model | Interactive image | ||
| KEGG | C19443  |
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| PubChem | 7294 | ||
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| Properties | |||
| C4H6O2 | |||
| Molar mass | 86.09 g·mol−1 | ||
| Appearance | Colorless liquid | ||
| Odor | Acrid[2] | ||
| Density | 0.95 g/cm3[3] | ||
| Melting point | −74 °C (−101 °F; 199 K)[3] | ||
| Boiling point | 80 °C (176 °F; 353 K)[3] | ||
| 5 g/100 mL | |||
| Vapor pressure | 65 mmHg (20°C)[2] | ||
| Vapor pressure | {{{value}}} | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |||
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.[4] It is also a reagent in the synthesis of various pharmaceutical intermediates.
Production, reactions, and uses
It is produced by acid-catalysed esterification of acrylic acid, which in turn is produced by oxidation of propylene. Owing to its tendency to polymerize, samples typically contain an inhibitor such as hydroquinone.
The compound undergoes transesterification to give a variety of other acrylate esters. The transesterification is facilitated because methanol and methyl acrylate form a low boiling azeotrope (b.p. 62-63 °C).[5] Several other esters are precursors to useful polymers.
Methyl acrylate is a classic Michael acceptor, which means that it adds nucleophiles at its terminus. For example in the presence of a base catalyst, it adds hydrogen sulfide to give the thioether:[6]
- 2 CH2CHCO2CH3 + H2S → S(CH2CH2CO2CH3)2
It is also a good dienophile.
Methyl acrylate is the precursor to fibers that are woven to make carpets. Acrylates are also used in the preparation of polyamidoamine (PAMAM) dendrimers typically by Michael addition with a primary amine.
Safety
It is an acute toxin with an LD50 (rats, oral) of 300 mg/kg and a TLV of 10 ppm.
References
- ↑ 1.0 1.1 Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 2.0 2.1 Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 3.0 3.1 3.2 Record in the GESTIS Substance Database of the IFA
- ↑ Takashi Ohara, Takahisa Sato, Noboru Shimizu, Günter Prescher Helmut Schwind, Otto Weiberg, Klaus Marten, Helmut Greim “Acrylic Acid and Derivatives” in Ullmann's Encyclopedia of Industrial Chemistry 2003, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a01_161.pub2
- ↑ Lua error in package.lua at line 80: module 'strict' not found.; Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.; Lua error in package.lua at line 80: module 'strict' not found.
