:Methyl acetate
{{distinguish|Menthyl acetate}}
{{chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 477004208
|Reference=Merck Index, 12th Edition, 6089.
|Name = Methyl acetate
|ImageFile = Methyl-acetate-2D-skeletal.svg
|ImageSize = 150px
|ImageAlt = Skeletal formula of methyl acetate
|ImageFile1 = Methyl-acetate-from-xtal-3D-bs-17.png
|ImageSize1 = 180px
|ImageAlt1 = Ball and stick model of the methyl acetate molecule
|PIN = Methyl acetate
|SystematicName = Methyl ethanoate
|OtherNames = Methyl ester of acetic acid
|Section1={{Chembox Identifiers
|PubChem = 6584
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = W684QT396F
|KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG = C17530
|InChI = 1/C3H6O2/c1-3(4)5-2/h1-2H3
|InChIKey = KXKVLQRXCPHEJC-UHFFFAOYAV
|ChEBI_Ref = {{ebicite|changed|EBI}}
|ChEBI = 77700
|ChEMBL_Ref = {{ebicite|correct|EBI}}
|ChEMBL = 14079
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C3H6O2/c1-3(4)5-2/h1-2H3
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = KXKVLQRXCPHEJC-UHFFFAOYSA-N
|CASNo = 79-20-9
|CASNo_Ref = {{cascite|correct|CAS}}
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 6335
|SMILES = O=C(OC)C
}}
|Section2={{Chembox Properties
|C=3 | H=6 | O=2
|Density = 0.932 g cm−3
|Appearance = Colorless liquid
|Solubility = ~25% (20 °C)
|MeltingPtC = -98
|BoilingPtC = 56.9
|RefractIndex = 1.361
|VaporPressure = 173 mmHg (20°C)
|MagSus = -42.60·10−6 cm3/mol
}}
|Section3={{Chembox Hazards
|NFPA-H = 2
|NFPA-F = 3
|ExternalSDS = [https://web.archive.org/web/20201021213134/http://hazard.com/msds/mf/baker/baker/files/m2743.htm External MSDS]
|IDLH = 3100 ppm{{PGCH|0391}}
|LD50 = 3700 mg/kg (oral, rabbit){{IDLH|79209|Methyl acetate}}
|PEL = TWA 200 ppm (610 mg/m3)
|REL = TWA 200 ppm (610 mg/m3) ST 250 ppm (760 mg/m3)
|FlashPtF = 14
|LCLo = 11,039 ppm (mouse, 4 hr)
21,753 ppm (cat, 1 hr)
32,000 ppm (rat, 4 hr)
}}
|Section4={{Chembox Related
|OtherFunction = Methyl formate
Ethyl acetate
Ethyl formate
Methyl fluoroacetate
|OtherFunction_label = esters
}}
}}
Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish removers. Methyl acetate is occasionally used as a solvent, being weakly polar and lipophilic, but its close relative ethyl acetate is a more common solvent being less toxic and less soluble in water. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or aqueous acids. Methyl acetate is not regulated as a volatile organic compound in the USA.{{cite book | author = Zeno, W. Wicks, JR, Frank N. Jones, S. Peter Pappas, and Douglas A. Wicks | title = Organic Coatings | location = Hoboken, New Jersey | publisher = Wiley | year = 2007 | isbn = 978-0-471-69806-7}}{{Cite web|url=https://www.paint.org/voc-exempt/|title=Update: U.S. EPA Exempt Volatile Organic Compounds|date=2018-01-30|website=American Coatings Association|language=en-US|access-date=2019-03-20}}
Preparation and reactions
Methyl acetate is produced industrially via the carbonylation of methanol as a byproduct of the production of acetic acid.Hosea Cheung, Robin S. Tanke, G. Paul Torrence “Acetic Acid” in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a01_045}} Methyl acetate also arises by esterification of acetic acid with methanol in the presence of strong acids such as sulfuric acid; this production process is famous{{According to whom|date=September 2024}} because of Eastman Kodak's intensified process using a reactive distillation.
=Reactions=
In the presence of strong bases such as sodium hydroxide or strong acids such as hydrochloric acid or sulfuric acid it is hydrolyzed back into methanol and acetic acid, especially at elevated temperature. The conversion of methyl acetate back into its components, by an acid, is a first-order reaction with respect to the ester. The reaction of methyl acetate and a base, for example sodium hydroxide, is a second-order reaction with respect to both reactants.
Methyl acetate is a Lewis base that forms 1:1 adducts with a variety of Lewis acids. It is classified as a hard base and is a base in the ECW model with EB =1.63 and CB = 0.95.
Applications
A major use of methyl acetate is as a volatile low toxicity solvent in glues, paints, and nail polish removers.
Acetic anhydride is produced by carbonylation of methyl acetate in a process that was inspired by the Monsanto acetic acid synthesis.{{cite journal |author1=Zoeller, J. R. |author2=Agreda, V. H. |author3=Cook, S. L. |author4=Lafferty, N. L. |author5=Polichnowski, S. W. |author6=Pond, D. M. | title = Eastman Chemical Company Acetic Anhydride Process | journal = Catalysis Today | year = 1992 | volume = 13 | pages = 73–91 | doi = 10.1016/0920-5861(92)80188-S}}
See also
References
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