Methyl acrylate

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Methyl acrylate
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Template:Longitem Template:Chembox Elements/molecular formula
Molar mass Template:Chem molar mass
Appearance Colorless liquid
Odor Acrid[2]
Density 0.95 g/cm3[3]
Melting point Template:Chembox CalcTemperatures
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Vapor pressure 65 mmHg (20°C)[2]
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Explosive limits 2.8–25%[2]

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Methyl acrylate is an organic compound, more accurately 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.[5] It is also a reagent in the synthesis of various pharmaceutical intermediates. Owing to the tendency of methyl acrylate to polymerize, samples typically contain an inhibitor such as hydroquinone.

Production

The standard industrial reaction for producing methyl acrylate is esterification of acrylic acid with methanol under acid catalysis (sulfuric acid, p-toluenesulfonic acid or acidic ion exchangers.[6]). The transesterification is facilitated because methanol and methyl acrylate form a low boiling azeotrope (boiling point 62–63 °C).[7]

The patent literature[8] describes a one-pot route involving vapor-phase oxidation of propene or 2-propenal with oxygen in the presence of methanol.

Other methods

Methyl acrylate can be prepared by debromination of methyl 2,3-dibromopropanoate with zinc.[9] Methyl acrylate is formed in good yield on pyrolysis of methyl lactate in the presence of ethenone (ketene).[10] Methyl lactate is a renewable "green chemical". Another patent[11] describes the dehydration of methyl lactate over zeolites.

The nickel tetracarbonyl-catalyzed hydrocarboxylation of acetylene with carbon monoxide in the presence of methanol also yields methyl acrylate.[12] The reaction of methyl formate with acetylene in the presence of transition metal catalysts also leads to methyl acrylate.[13] Both, the alcoholysis of propiolactone with methanol as well as the methanolysis of acrylonitrile via intermediately formed acrylamide sulfate[14] are also proven but obsolete processes.

Use

Methyl acrylate is after butyl acrylate and ethyl acrylate the third most important acrylic ester with a worldwide annual production of about 200,000 tons in 2007.[15] Poly(methyl acrylate) is a tacky material near room temperature, and as such it is not particularly useful as a structural material. Commonly, methyl acrylate (and other acrylate esters) are copolymerized with other alkenes to give useful engineering plastics.[16] A variety of vinyl monomers are used, including styrene and other acrylates.[17] The resulting copolymers give acrylic paints that are harder and more brittle than those with the homologous acrylates. Copolymerizing methyl acrylate with acrylonitrile improves their melt processability to fibers, which could be used as precursors for carbon fibers.[18] Methyl acrylate is the precursor to fibers that are woven to make carpets.

Amino derivatives

Methyl acrylate reacts catalysed by Lewis bases in a Michael addition with amines in high yields to β-alanine derivatives which provide amphoteric surfactants when long-chain amines are used and the ester function is hydrolysed subsequently.

Acrylates are also used in the preparation of poly(amidoamine) (PAMAM) dendrimers typically by Michael addition with a primary amine.

Amphotere beta-alanine

Methyl acrylate is used for the preparation of 2-dimethylaminoethyl acrylate by transesterification with dimethylaminoethanol in significant quantities of over 50,000 tons / year.[19]

Reactions

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:[20]

2 CH2CHCO2CH3 + H2S → S(CH2CH2CO2CH3)2

It is also a good dienophile.

Safety

It is an acute toxin with an LD50 (rats, oral) of 300 mg/kg and a TLV of 10 ppm.

References

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  1. ↑ a b Script error: No such module "citation/CS1".
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  3. ↑ Record in the GESTIS Substance Database of the Institute for Occupational Safety and HealthScript error: No such module "TemplatePar". Script error: No such module "TemplatePar".
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  7. ↑ Script error: No such module "Citation/CS1".; Script error: No such module "citation/CS1"..
  8. ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Ferlazzo, Natale; Buzzi, Gian Fausto & Ghirga, Marcello, "Process for the production of methyl acrylate", published Script error: No such module "auto date formatter"., assigned to Societa' Italiana Resine S.I.R., S.p.A. Script error: No such module "Check for unknown parameters".
  9. ↑ F. Beilstein: Handbuch der organischen Chemie, 3. Auflage, 1. Band. Verlag Leopold Voss, 1893, S. 501. Volltext.
  10. ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Hagemeyer, Hugh J., "Preparation of methyl acrylate", published Script error: No such module "auto date formatter"., assigned to Eastman Kodak Company Script error: No such module "Check for unknown parameters".
  11. ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Abe, Takafumi & Hieda, Shinichi, "Process for preparing unsaturated carboxylic acid or ester thereof", published Script error: No such module "auto date formatter"., assigned to Mitsubishi Gas Chemical Company Script error: No such module "Check for unknown parameters".
  12. ↑ W. Reppe, J. Liebigs Ann. Chem., 582 (1), 116-132 (1953)
  13. ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Liu, Zhao-Tie; Zhang, Jia-Qi & Yang, Xian-Gui, "Method for synthesizing methyl acrylate", published Script error: No such module "auto date formatter"., assigned to Chengdu Institute of Organic Chemistry and National Research and Engineering Centre for Coal Slurry Gasification and Coal Chemical Industry Script error: No such module "Check for unknown parameters".
  14. ↑ H.-J. Arpe, Industrielle Organische Chemie, 6. Aufl., Wiley-VCH Verlag, Weinheim, 2007, Template:ISBN.
  15. ↑ CEH Marketing Research Report Acrylic Acid and Esters, SRI Consulting, July 2007.
  16. ↑ Script error: No such module "citation/CS1".
  17. ↑ DOW Methyl acrylate, Product Safety Assessment
  18. ↑ Script error: No such module "citation/CS1".
  19. ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Paul, Jean-Michel; Tonnelier, Boris & Augustin, Francis, "Composition including dialkyl tin oxide and use thereof as a transesterification catalyst for the synthesis of (meth)acrylic esters", published Script error: No such module "auto date formatter"., assigned to Arkema Script error: No such module "Check for unknown parameters".
  20. ↑ Script error: No such module "Citation/CS1".; Script error: No such module "citation/CS1"..

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