View source for Allyl alcohol

{{Short description|1=Organic compound (CH2=CHCH2OH)}}
{{chembox
| Verifiedfields = changed
| Watchedfields  = changed
| verifiedrevid  = 477314350
| ImageFile      = Allyl_alcohol_v2.svg
| ImageName      = Skeletal formula
| ImageFile1     = Allyl-alcohol-3D-balls-2.png
| 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 [[Alcohol (chemistry)|alcohol]]s, it is a water-soluble, colourless liquid.  It is more toxic than typical small alcohols. Allyl alcohol is used as a [[Precursor (chemistry)|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 [[allyl]]ic [[Alcohol (chemistry)|alcohol]]s.

==Production==
Allyl alcohol is produced commercially by the [[Olin Corporation|Olin]] and [[Royal Dutch Shell|Shell]] [[corporation]]s 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 [[Propan-1-ol|propanol]].

===Laboratory methods===
In the laboratory, [[glycerol]] reacts with [[oxalic acid|oxalic]] or [[formic acid]]s to give (respectively) [[dioxalin]] or glyceric formate, either of which [[decarboxylate]] and [[Dehydration reaction|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 [[Riley oxidation|selenium dioxide]] or [[Kharasch-Sosnovsky reaction|organic peroxide]]s. 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 [[enone]]s 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 André Thomas Cahours|Auguste Cahours]] and [[August Wilhelm von Hofmann|August Hofmann]] by [[hydrolysis]] of [[allyl iodide]].<ref name=Ullmann /> Today a
Allyl alcohol can be formed after [[trituration]] of [[Garlic|garlic (Allium sativum)]] cloves (producing from garlic in two ways: firstly by a [[Condensation reaction|self-condensation]] reaction of [[allicin]] and its [[Chemical decomposition|decomposition]] products such as  [[Diallyl trisulfide|diallyl trisulphide]] and [[Diallyl disulfide|diallyl disulphide]] and secondly by the [[Chemical reaction|reaction]] between [[alliin]], the [[Precursor (chemistry)|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>

==Applications==
Allyl alcohol is converted mainly to [[glycidol]], which is a [[Reaction intermediate|chemical intermediate]] in the synthesis of [[glycerol]], glycidyl ethers, [[ester]]s, and [[amine]]s. Also, a variety of [[polymer]]izable esters are prepared from allyl alcohol, e.g. diallyl [[phthalate]].<ref name=Ullmann/>

Allyl alcohol has [[herbicide|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 [[rat]]s, ''[[in vivo]]'', allyl alcohol is [[Metabolism|metabolized]] by [[liver]] [[alcohol dehydrogenase]] to [[acrolein]], which can cause [[damage]] to the [[microtubule]]s of rat [[hepatocyte]] [[Mitochondrion|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]]