{{Short description|1=Organic compound (CH2=CHCH2OH)}} {{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477314350 | ImageFile = Allyl_alcohol_v2.svg | ImageClass = skin-invert | ImageName = Skeletal formula | ImageFile1 = Allyl-alcohol-3D-balls-2.png | ImageClass1 = bg-transparent | ImageName1 = Ball-and-stick model | PIN = Prop-2-en-1-ol | OtherNames = Allyl alcohol<br />2-Propen-1-ol<br />1-Propen-3-ol<ref name=NIOSH/><br/>Vinyl carbinol<ref name=NIOSH/><br/>Allylic alcohol<br/>Weed drench{{citation needed|date=July 2023}} | Section1 = {{Chembox Identifiers | PubChem = 7858 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C02001 | InChIKey = XXROGKLTLUQVRX-UHFFFAOYAC | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 234926 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C3H6O/c1-2-3-4/h2,4H,1,3H2 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = XXROGKLTLUQVRX-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo =107-18-6 | UNII_Ref = {{fdacite|changed|FDA}} | UNII = 3W678R12M0 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 16605 | SMILES = C=CCO | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID =13872989 | 3DMet = B00381 | RTECS = BA5075000 | UNNumber = 1098 | EC_number = 203-470-7 | InChI =1/C3H6O/c1-2-3-4/h2,4H,1,3H2}} | Section2 = {{Chembox Properties | C=3 | H=6 | O=1 | Appearance = colorless liquid<ref name=NIOSH/> | Odor = mustard-like<ref name=NIOSH/> | Density =0.854 g/ml | BoilingPtC = 97 | BoilingPt_notes = | MeltingPtC = −129 | pKa = 15.5 (H<sub>2</sub>O)<ref name="CRC97">{{cite book | editor= Haynes, William M. | year = 2016 | title = CRC Handbook of Chemistry and Physics | edition = 97th | publisher = CRC Press | isbn = 978-1498754286 | pages=5–88 | title-link = CRC Handbook of Chemistry and Physics }}</ref> | Solubility =Miscible | Solvent =Water | VaporPressure = 17 mmHg<ref name=NIOSH/> | MagSus = −36.70·10<sup>−6</sup> cm<sup>3</sup>/mol }} | Section3 = {{Chembox Hazards | MainHazards= Highly toxic, lachrymator | ExternalSDS = [https://www.finarchemicals.com/msds/Allyl%20alcohol.pdf External MSDS] | NFPA-H=3 | NFPA-F=3 | NFPA-R=1 | GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}}{{GHS09}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|225|301|302|311|315|319|331|335|400}} | PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|270|271|273|280|301+310|302+352|303+361+353|304+340|305+351+338|311|312|321|322|330|332+313|337+313|361|362|363|370+378|391|403+233|403+235|405|501}} | FlashPtC = 21 | AutoignitionPtC = 378 | ExploLimits =2.5–18.0% | PEL = 2 ppm<ref name=NIOSH>{{PGCH|0017}}</ref> | IDLH = 20 ppm<ref name=NIOSH/> | REL = TWA 2 ppm (5 mg/m<sup>3</sup>) ST 4 ppm (10 mg/m<sup>3</sup>) [skin] <ref name=NIOSH/> | LD50 = 80 mg/kg (rat, orally)<ref>Allyl alcohol toxicity</ref> | LC50 = 1000 ppm (mammal, 1 hr)<br/>76 ppm (rat, 8 hr)<br/>207 ppm (mouse, 2 hr)<br/>1000 ppm (rabbit, 3.5 hr)<br/>1000 ppm (monkey, 4 hr)<br/>1060 ppm (rat, 1 hr)<br/>165 ppm (rat, 4 hr)<br/>76 ppm (rat, 8 hr)<ref>{{IDLH|107186|Allyl alcohol}}</ref> }} }}
'''Allyl alcohol''' (IUPAC name: '''prop-2-en-1-ol''') is an organic compound with the structural formula {{chem2|CH2\dCHCH2OH}}. Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a precursor to many specialized compounds such as flame-resistant materials, drying oils, and plasticizers.<ref name=Ullmann>{{Ullmann|author=Ludger Krähling|author2=Jürgen Krey|author3=Gerald Jakobson|author4=Johann Grolig|author5=Leopold Miksche|title=Allyl Compounds|year=2002|doi=10.1002/14356007.a01_425}}</ref> Allyl alcohol is the smallest representative of the allylic alcohols.
==Production== Allyl alcohol is produced commercially by the Olin and Shell corporations through the hydrolysis of allyl chloride: :{{chem2|CH2\dCHCH2Cl + NaOH -> CH2\dCHCH2OH + NaCl}} Allyl alcohol can also be made by the rearrangement of propylene oxide, a reaction that is catalyzed by potassium alum at high temperature. The advantage of this method relative to the allyl chloride route is that it does not generate salt. Also avoiding chloride-containing intermediates is the "acetoxylation" of propylene to allyl acetate: :{{chem2|CH2\dCHCH3 + 1/2 O2 + CH3CO2H -> CH2\dCHCH2O2CCH3 + H2O}} Hydrolysis of this acetate gives allyl alcohol. In alternative fashion, propylene can be oxidized to acrolein, which upon hydrogenation gives the alcohol.
In principle, allyl alcohol can be obtained by dehydrogenation of propanol.
===Laboratory methods=== In the laboratory, glycerol reacts with oxalic or formic acids to give (respectively) dioxalin or glyceric formate, either of which decarboxylate and dehydrate to allylol.<ref>{{OrgSynth | volume = 1 | page = 15 | doi= 10.15227/orgsyn.001.0015 | title = Allyl alcohol | author =Oliver Kamm | author2 =C. S. Marvel | name-list-style=amp | year = 1941}}</ref><ref>{{cite book|last=Cohen|first=Julius|title=Practical Organic Chemistry|edition=2nd|year=1900|publisher=Macmillan and Co., Limited|location=London|page=[https://archive.org/details/practicalorgani00cohegoog/page/n114 96]|url=https://archive.org/details/practicalorgani00cohegoog|quote=Practical Organic Chemistry Cohen Julius.}}</ref>
Allyl alcohols in general are prepared by allylic oxidation of allyl compounds, using selenium dioxide or organic peroxides. Other methods include carbon-carbon bond-forming reactions such as the Prins reaction, the Morita-Baylis-Hillman reaction, or a variant of the Ramberg-Bäcklund reaction. Hydrogenation of enones is another route. Some of these methods are achieved by the Luche reduction, Wharton reaction, and the Mislow-Evans rearrangement.
Allyl alcohol was first prepared in 1856 by Auguste Cahours and August Hofmann by hydrolysis of allyl iodide.<ref name=Ullmann /> Allyl alcohol can be formed by trituration of garlic (Allium sativum) cloves (producing from garlic in two ways: firstly by a self-condensation reaction of allicin and its decomposition products such as diallyl trisulphide and diallyl disulphide and secondly by the reaction between alliin, the precursor of allicin, and water).<ref name=":0">{{Cite journal |last1=Lemar |first1=Katey M. |last2=Passa |first2=Ourania |last3=Aon |first3=Miguel A. |last4=Cortassa |first4=Sonia |last5=Müller |first5=Carsten T. |last6=Plummer |first6=Sue |last7=O'Rourke |first7=Brian |last8=Lloyd |first8=David |date=2005 |title=Allyl alcohol and garlic (Allium sativum) extract produce oxidative stress in ''Candida albicans'' |journal=Microbiology |volume=151 |issue=10 |pages=3257–3265 |doi=10.1099/mic.0.28095-0 |doi-access=free |issn=1465-2080 |pmc=2711876 |pmid=16207909}}</ref> The compound's various connections with garlic give the allyl group its name (from Latin "allium" meaning garlic).
==Applications== Allyl alcohol is converted mainly to glycidol, which is a chemical intermediate in the synthesis of glycerol, glycidyl ethers, esters, and amines. Also, a variety of polymerizable esters are prepared from allyl alcohol, e.g. diallyl phthalate.<ref name=Ullmann/>
Allyl alcohol has herbicidal activity and can be used as a weed eradicant<ref name=":1">{{Cite web |last=Laiho Mikola |first=O.P. |orig-date=1964 |title=Studies on the effect of some eradicants on mycorrhizal development in forest nurseries. |url=https://helda.helsinki.fi/bitstream/handle/10138/17658/77-1964_Laiho.pdf?sequence=1 |access-date=2024-01-24 |website=helda.helsinki.fi}}</ref>) and fungicide.<ref name=":0" />
Allyl alcohol is the precursor in the commercial synthesis of allyl bromide:<ref>{{cite book| doi = 10.1002/14356007.a04_405.pub2| chapter = Bromine Compounds| title = Ullmann's Encyclopedia of Industrial Chemistry| date = 2013| last1 = Yoffe| first1 = David| last2 = Frim| first2 = Ron| last3 = Ukeles| first3 = Shmuel D.| last4 = Dagani| first4 = Michael J.| last5 = Barda| first5 = Henry J.| last6 = Benya| first6 = Theodore J.| last7 = Sanders| first7 = David C.| pages = 1–31| isbn = 978-3-527-30385-4}}</ref> :{{chem2|CH2\dCHCH2OH + HBr → CH2\dCHCH2Br + H2O}}
==Safety== Allyl alcohol is hepatotoxic. In rats, ''in vivo'', allyl alcohol is metabolized by liver alcohol dehydrogenase to acrolein, which can cause damage to the microtubules of rat hepatocyte mitochondria and depletion of glutathione.<ref name=":0" /> It is significantly more toxic than related alcohols.<ref name=Ullmann/><ref>{{cite web |title=National Technical Information Service |url=https://ntrl.ntis.gov/NTRL/dashboard/searchResults.xhtml?searchQuery=PB88170857 |website=US Environmental Protection Agency|date = 1984}}</ref> Its threshold limit value (TLV) is 2 ppm. It is a lachrymator.<ref name=Ullmann/>
==See also== * Propargyl alcohol
==References== {{Reflist}}
== External links == *{{ICSC|0095|00}} *{{PGCH|0017}} *{{INRS|title=Alcool allylique|number=156|year=2004}} * [http://www.michigan.gov/documents/MDCH_-_Allyl_Alcohol_Public_Draft_117607_7.pdf State of Michigan public information on allyl alcohol] * [https://web.archive.org/web/20051221170932/http://hazmap.nlm.nih.gov/cgi-bin/hazmap_generic?tbl=TblAgents&id=242 Occupational exposure guidelines]
{{Authority control}}
Category:Primary alcohols Category:Allyl compounds Category:Hepatotoxins Category:Substances discovered in the 19th century