| Revision as of 04:46, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 463262455 of page Allyl_acetate for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 13:42, 19 January 2024 edit Maxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,042 edits Add: publisher, title. Changed bare reference to CS1/2. |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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| verifiedrevid = 387693830 |
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| ImageFile = Allyl acetate.png |
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| verifiedrevid = 477314404 |
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| ImageSize = 200px |
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| ImageFile = Allyl Acetate ChemDraw.png |
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| IUPACName = 2-Propenyl acetate |
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| SystematicName = |
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| ImageSize = 170 |
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| ImageAlt = Skeletal formula of allyl acetate |
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| OtherNames = |
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| ImageFile1 = Allyl acetate 3D ball.png |
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| Section1 = {{Chembox Identifiers |
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| ImageAlt1 = Ball-and-stick model of the allyl acetate molecule |
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| SMILES = C=CCOC(C)=O |
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| PIN = Prop-2-enyl acetate<ref>{{cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/11584#section=IUPAC-Name&fullscreen=true | title=Allyl acetate }}</ref> |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| OtherNames = 2-Propenyl acetate<br />Allyl acetate |
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| ChemSpiderID = 11096 |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite}} |
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| CASNo = 591-87-7 |
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| SMILES = C=CCOC(C)=O |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| PubChem = |
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| StdInChI = 1S/C5H8O2/c1-3-4-7-5(2)6/h3H,1,4H2,2H3 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = FWZUNOYOVVKUNF-UHFFFAOYSA-N |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 13862665 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 591-87-7 |
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| PubChem = 11584 |
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| EC_number = 209-734-8 |
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| RTECS = AF1750000 |
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| UNNumber = 2333 |
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| UNII = E4U5E5990I |
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| ChEMBL = 1890774 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=5|H=8|O=2 |
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| C=5 | H=8 | O=2 |
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| Appearance = Colorless liquid |
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| Appearance = Colorless liquid |
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| Density = 0.928 g/cm<sup>3</sup> |
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| Density = 0.928 g/cm<sup>3</sup> |
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| MeltingPtC = |
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| BoilingPtC = 103 |
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| BoilingPtC = 103 |
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| Solubility = slightly soluble |
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| MagSus = -56.7·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| Section7 = {{Chembox Hazards |
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| RPhrases = {{R11}} {{R21}} {{R23}} {{R25}} {{R36}} |
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| GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}} |
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| GHSSignalWord = Danger |
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| SPhrases = {{S16}} {{S26}} {{S45}} {{S36}} |
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| HPhrases = {{H-phrases|225|301|312|319|330}} |
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| FlashPt = |
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| 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}} |
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| ExploLimits = |
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| AutoignitionPtC = 374 |
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'''Allyl acetate''' is an ] with formula C<sub>3</sub>H<sub>5</sub>OC(O)CH<sub>3</sub>. This colourless liquid is a precursor to especially ], which is a useful industrial intermediate. It is the ] ester of allyl alcohol. |
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==Preparation== |
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Allyl acetate is produced industrially by the gas phase reaction of ] in the presence of ] using a ] ]:<ref>{{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 = ] excerpt | year = 2004|publisher=John Wiley & Sons }}</ref><ref name=Ullmann>{{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}}</ref> |
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:C<sub>3</sub>H<sub>6</sub> + CH<sub>3</sub>COOH + ½ O<sub>2</sub> → CH<sub>2</sub>=CHCH<sub>2</sub>OCOCH<sub>3</sub> + H<sub>2</sub>O |
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This method is advantageous because propene is inexpensive and a ]. 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. |
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] is produced similarly, using ] in place of propene. These reactions are examples of acetoxylation. The palladium center is then re-oxidized by the O<sub>2</sub> present. The mechanism for the acetoxylation follows a similar pathway, with propene forming a π-allyl bond on the palladium.<ref>{{cite journal|author1=M. R. Churchill |author2=R. Mason | title = Molecular Structure of π-allyl-palladium acetate | doi = 10.1038/204777a0| journal = ] | volume = 204 | year = 1964 |pages = 777 | issue=4960|bibcode=1964Natur.204..777C | doi-access = free }}</ref> |
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==Reactions and applications== |
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Allyl acetate can be hydrolyzed to ]: |
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:CH<sub>2</sub>=CHCH<sub>2</sub>OCOCH<sub>3</sub> + H<sub>2</sub>O → CH<sub>2</sub>=CHCH<sub>2</sub>OH + CH<sub>3</sub>COOH |
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Allyl alcohol is a precursor for some specialty polymers, mainly for ]. Allyl alcohol is also a precursor to synthetic ]. Epoxidation by ] produces ], which undergoes hydrolysis to glycerol. |
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:CH<sub>2</sub>=CHCH<sub>2</sub>OH + HOOH → CH<sub>2</sub>OCHCH<sub>2</sub>OH + H<sub>2</sub>O |
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:CH<sub>2</sub>OCHCH<sub>2</sub>OH + H<sub>2</sub>O → C<sub>3</sub>H<sub>5</sub>(OH)<sub>3</sub> |
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Synthetic glycerol tends to be used in cosmetics and toiletries whereas glycerol from the hydrolysis of fats is used in food.<ref>{{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 = –214|publisher=John Wiley & Sons | isbn=978-0-471-44385-8}}</ref> |
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===Substitution reactions=== |
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Substitution of the acetate group in allyl acetate using hydrogen chloride yields ]. Reaction with ] over copper catalyst yields ].<ref>{{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}}</ref> |
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:CH<sub>2</sub>=CHCH<sub>2</sub>OCOCH<sub>3</sub> + HCl → CH<sub>2</sub>=CHCH<sub>2</sub>Cl + CH<sub>3</sub>COOH |
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:CH<sub>2</sub>=CHCH<sub>2</sub>OCOCH<sub>3</sub> + HCN → CH<sub>2</sub>=CHCH<sub>2</sub>CN + CH<sub>3</sub>COOH |
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] is generally produced directly by the chlorination of propene. |
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==References== |
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{{reflist}} |
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] |
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] |