| 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 473697878 of page Allyl_alcohol for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 22:12, 17 December 2024 edit Innerstream (talk | contribs)Autopatrolled, Extended confirmed users3,981 editsmNo edit summary |
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{{Short description|1=Organic compound (CH2=CHCH2OH)}} |
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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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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 443376202 |
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| Watchedfields = changed |
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| ImageFile = Allyl-alcohol.png |
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| verifiedrevid = 477314350 |
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| ImageName = Skeletal formula |
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| ImageFile = Allyl_alcohol_v2.svg |
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| ImageFile1 = Allyl-alcohol-3D-balls-2.png |
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| ImageName = Skeletal formula |
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| ImageName1 = Ball-and-stick model |
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| ImageFile1 = Allyl-alcohol-3D-balls-2.png |
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| IUPACName = Prop-2-en-1-ol, Allyl alcohol |
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| ImageName1 = Ball-and-stick model |
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| Section1 = {{Chembox Identifiers |
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| PIN = Prop-2-en-1-ol |
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| 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}} |
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| Section1 = {{Chembox Identifiers |
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| PubChem = 7858 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C02001 |
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| KEGG = C02001 |
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| StdInChIKey = XXROGKLTLUQVRX-UHFFFAOYSA-N |
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| StdInChIKey = XXROGKLTLUQVRX-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=107-18-6 |
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| CASNo =107-18-6 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = 3W678R12M0 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 16605 |
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| ChEBI = 16605 |
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| SMILES = C=CCO |
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| SMILES = C=CCO |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID=13872989 |
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| ChemSpiderID =13872989 |
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| 3DMet = B00381 |
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| InChI=1/C3H6O/c1-2-3-4/h2,4H,1,3H2}} |
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| RTECS = BA5075000 |
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|Section2 = {{Chembox Properties |
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| UNNumber = 1098 |
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| C = 3 | H = 6 | O = 1 |
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| EC_number = 203-470-7 |
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| Density=0.854 g/ml |
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| InChI =1/C3H6O/c1-2-3-4/h2,4H,1,3H2}} |
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| MeltingPt=−129 °C |
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| Section2 = {{Chembox Properties |
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| BoilingPt=97 °C |
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| C=3 | H=6 | O=1 |
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| Solubility=Miscible |
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| Appearance = colorless liquid<ref name=NIOSH/> |
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| Solvent=Water |
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| Odor = mustard-like<ref name=NIOSH/> |
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| Density =0.854 g/ml |
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| BoilingPtC = 97 |
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| BoilingPt_notes = |
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| MeltingPt =−129 °C |
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| 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 = ] | isbn = 978-1498754286 | pages=5–88 | title-link = CRC Handbook of Chemistry and Physics }}</ref> |
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| Solubility =Miscible |
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| Solvent =Water |
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| VaporPressure = 17 mmHg<ref name=NIOSH/> |
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| MagSus = -36.70·10<sup>−6</sup> cm<sup>3</sup>/mol |
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}} |
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|Section3={{Chembox Hazards |
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| Section3 = {{Chembox Hazards |
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| MainHazards= Highly toxic, lachrymator |
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| EUClass=Toxic ('''T''')<br />Dangerous for<br />the environment ('''N''') |
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| ExternalSDS = |
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| EUIndex=603-015-00-6 |
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| ExternalMSDS = |
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| NFPA-H=3 |
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| NFPA-H=3 |
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| NFPA-F=3 |
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| NFPA-F=3 |
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| NFPA-R=0 |
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| NFPA-R=1 |
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| RPhrases={{R10}}, {{R23/24/25}},<br />{{R36/37/38}}, {{R50}} |
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| GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}}{{GHS09}} |
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| GHSSignalWord = Danger |
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| SPhrases={{S1/2}}, {{S36/37/39}},<br />{{S38}}, {{S45}}, {{S61}} |
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| HPhrases = {{H-phrases|225|301|302|311|315|319|331|335|400}} |
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| FlashPt=21 °C |
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| 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}} |
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| Autoignition=378 °C |
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| FlashPtC = 21 |
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| ExploLimits=2.5–18.0%}} |
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| AutoignitionPtC = 378 |
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| ExploLimits =2.5–18.0% |
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| PEL = 2 ppm<ref name=NIOSH>{{PGCH|0017}}</ref> |
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| IDLH = 20 ppm<ref name=NIOSH/> |
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| REL = TWA 2 ppm (5 mg/m<sup>3</sup>) ST 4 ppm (10 mg/m<sup>3</sup>) <ref name=NIOSH/> |
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| LD50 = 80 mg/kg (rat, orally)<ref>Allyl alcohol toxicity</ref> |
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| 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> |
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}} |
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'''Allyl alcohol''' (]: '''prop-2-en-1-ol''') is an ] with the ] {{chem2|CH2\dCHCH2OH}}. Like many ]s, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a ] to many specialized compounds such as flame-resistant materials, ], and ].<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 ]ic ]s. |
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==Production== |
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Allyl alcohol is produced commercially by the ] and ] ]s through the hydrolysis of ]: |
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:{{chem2|CH2\dCHCH2Cl + NaOH -> CH2\dCHCH2OH + NaCl}} |
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Allyl alcohol can also be made by the rearrangement of ], a reaction that is catalyzed by ] 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 ] to ]: |
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:{{chem2|CH2\dCHCH3 + 1/2 O2 + CH3CO2H -> CH2\dCHCH2O2CCH3 + H2O}} |
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Hydrolysis of this acetate gives allyl alcohol. In alternative fashion, ] can be oxidized to ], which upon ] gives the alcohol. |
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In principle, allyl alcohol can be obtained by ] of ]. |
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===Laboratory methods=== |
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In the laboratory, ] reacts with ] or ]s to give (respectively) ] or glyceric formate, either of which ] and ] 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=|url=https://archive.org/details/practicalorgani00cohegoog|quote=Practical Organic Chemistry Cohen Julius.}}</ref> |
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Allyl alcohols in general are prepared by ] of ] compounds, using ] or ]s. Other methods include carbon-carbon bond-forming reactions such as the ], the ], or a variant of the ]. Hydrogenation of ]s is another route. Some of these methods are achieved by the ], ], and the ]. |
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Allyl alcohol was first prepared in 1856 by ] and ] by ] of ].<ref name=Ullmann /> Today a |
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Allyl alcohol can be formed after ] of ] cloves (producing from garlic in two ways: firstly by a ] reaction of ] and its ] products such as ] and ] and secondly by the ] between ], the ] of ], and ]).<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> |
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==Applications== |
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Allyl alcohol is converted mainly to ], which is a ] in the synthesis of ], glycidyl ethers, ]s, and ]s. Also, a variety of ]izable esters are prepared from allyl alcohol, e.g. diallyl ].<ref name=Ullmann/> |
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Allyl alcohol has ] and can be used as a ] 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 ].<ref name=":0" /> |
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Allyl alcohol is the precursor in the commercial synthesis of ]:<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> |
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:{{chem2|CH2\dCHCH2OH + HBr → CH2\dCHCH2Br + H2O}} |
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==Safety== |
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Allyl alcohol is ]. In ]s, '']'', allyl alcohol is ] by ] ] to ], which can cause ] to the ]s of rat ] ] and depletion of ].<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 ].<ref name=Ullmann/> |
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==See also== |
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* ] |
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==References== |
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{{Reflist}} |
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== External links == |
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*{{ICSC|0095|00}} |
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*{{PGCH|0017}} |
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*{{INRS|title=Alcool allylique|number=156|year=2004}} |
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{{Authority control}} |
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