Allyl acetate
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477314404
| ImageFile = Allyl Acetate ChemDraw.png
| ImageSize = 170
| ImageAlt = Skeletal formula of allyl acetate
| ImageFile1 = Allyl acetate 3D ball.png
| ImageAlt1 = Ball-and-stick model of the allyl acetate molecule
| PIN = Prop-2-enyl acetate{{cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/11584#section=IUPAC-Name&fullscreen=true | title=Allyl acetate }}
| OtherNames = 2-Propenyl acetate
Allyl acetate
|Section1={{Chembox Identifiers
| SMILES = C=CCOC(C)=O
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C5H8O2/c1-3-4-7-5(2)6/h3H,1,4H2,2H3
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = FWZUNOYOVVKUNF-UHFFFAOYSA-N
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 13862665
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 591-87-7
| PubChem = 11584
| EC_number = 209-734-8
| RTECS = AF1750000
| UNNumber = 2333
| UNII = E4U5E5990I
| ChEMBL = 1890774
}}
|Section2={{Chembox Properties
| C=5 | H=8 | O=2
| Appearance = Colorless liquid
| Density = 0.928 g/cm3
| MeltingPtC =
| BoilingPtC = 103
| Solubility = slightly soluble
| MagSus = −56.7·10−6 cm3/mol
}}
|Section7={{Chembox Hazards
| ExternalSDS =
| NFPA-H =
| NFPA-R =
| NFPA-F =
| GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|225|301|312|319|330}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|260|264|270|271|280|284|301+310|302+352|303+361+353|304+340|305+351+338|310|312|320|321|322|330|337+313|363|370+378|403+233|403+235|405|501}}
| FlashPt =
| ExploLimits =
| AutoignitionPtC = 374
}}
}}
Allyl acetate is an organic compound with formula C3H5OC(O)CH3. This colourless liquid is a precursor to especially allyl alcohol, which is a useful industrial intermediate. It is the acetate ester of allyl alcohol.
Preparation
Allyl acetate is produced industrially by the gas phase reaction of propene in the presence of acetic acid using a palladium catalyst:{{cite book | title = Industrial organic chemicals |author1=Harold Wittcoff |author2=B. G. Reuben |author3=Jeffrey S. Plotkin | page = 212 | isbn = 978-0-471-54036-6 | url = https://books.google.com/books?id=4KHzc-nYPNsC&pg=PA212 | format = Google Books excerpt | year = 2004|publisher=John Wiley & Sons }}{{cite encyclopedia|author=Ludger Krähling|author2=Jürgen Krey|author3=Gerald Jakobson|author4=Johann Grolig|author5=Leopold Miksche|chapter=Allyl Compounds|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2002|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a01_425|isbn=978-3527306732}}
:C3H6 + CH3COOH + ½ O2 → CH2=CHCH2OCOCH3 + H2O
This method is advantageous because propene is inexpensive and a green chemical. Allyl alcohol is also produced primarily from allyl chloride, but production via the hydrolysis of allyl acetate route avoids the use of chlorine, and so is increasing in use.
Vinyl acetate is produced similarly, using ethylene in place of propene. These reactions are examples of acetoxylation. The palladium center is then re-oxidized by the O2 present. The mechanism for the acetoxylation follows a similar pathway, with propene forming a π-allyl bond on the palladium.{{cite journal|author1=M. R. Churchill |author2=R. Mason | title = Molecular Structure of π-allyl-palladium acetate | doi = 10.1038/204777a0| journal = Nature | volume = 204 | year = 1964 |pages = 777 | issue=4960|bibcode=1964Natur.204..777C | doi-access = free }}
:Image:Allyl Acetate Catalytic Cycle ChemDraw.png
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Reactions and applications
Allyl acetate can be hydrolyzed to allyl alcohol:
:CH2=CHCH2OCOCH3 + H2O → CH2=CHCH2OH + CH3COOH
Allyl alcohol is a precursor for some specialty polymers, mainly for drying oils. Allyl alcohol is also a precursor to synthetic glycerol. Epoxidation by hydrogen peroxide produces glycidol, which undergoes hydrolysis to glycerol.
:CH2=CHCH2OH + HOOH → CH2OCHCH2OH + H2O
:CH2OCHCH2OH + H2O → C3H5(OH)3
Synthetic glycerol tends to be used in cosmetics and toiletries whereas glycerol from the hydrolysis of fats is used in food.{{cite book|author1=H. A. Wittcoff |author2=B. G. Reuben |author3=J. S. Plotkin | title = Industrial Organic Chemicals|url=https://archive.org/details/industrialorgani00witt |url-access=limited | chapter = Chemicals and Polymers from Propylene |year = 2004 |pages = [https://archive.org/details/industrialorgani00witt/page/n219 195]–214|publisher=John Wiley & Sons | isbn=978-0-471-44385-8}}
=Substitution reactions=
Substitution of the acetate group in allyl acetate using hydrogen chloride yields allyl chloride. Reaction with hydrogen cyanide over copper catalyst yields allyl cyanide.{{cite journal| author=Ludger Krahling| title = Allyl Compounds | journal = Ullmann's Encyclopedia of Industrial Chemistry| year=2000 | doi=10.1002/14356007.a01_425| isbn = 9783527303854 |display-authors=etal}}
:CH2=CHCH2OCOCH3 + HCl → CH2=CHCH2Cl + CH3COOH
:CH2=CHCH2OCOCH3 + HCN → CH2=CHCH2CN + CH3COOH
Allyl chloride is generally produced directly by the chlorination of propene.