Allyl alcohol: Difference between revisions

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	\| Watchedfields = changed		\| Watchedfields = changed
	\| verifiedrevid = 477314350		\| verifiedrevid = 477314350
	\| ImageFile = ~~Allylalcohol~~.~~png~~		\| ImageFile = Allyl_alcohol_v2.svg
	\| ImageName = Skeletal formula		\| ImageName = Skeletal formula
	\| ImageFile1 = Allyl-alcohol-3D-balls-2.png		\| ImageFile1 = Allyl-alcohol-3D-balls-2.png
	\| ImageName1 = Ball-and-stick model		\| ImageName1 = Ball-and-stick model
	\| PIN = Prop-2-en-1-ol		\| 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{{~~cite~~ needed\|date=July 2023}}		\| 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		\| Section1 = {{Chembox Identifiers
	\| PubChem = 7858		\| PubChem = 7858
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	\| BoilingPt_notes =		\| BoilingPt_notes =
	\| MeltingPt =−129 °C		\| MeltingPt =−129 °C
	\| 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 \| ~~page~~=5–88 \| title-link = CRC Handbook of Chemistry and Physics }}</ref>		\| 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>
	\| Solubility =Miscible		\| Solubility =Miscible
	\| Solvent =Water		\| Solvent =Water
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	==Production==		==Production==
	Allyl alcohol is produced commercially by the ] and ] ]s through the hydrolysis of ]:		Allyl alcohol is produced commercially by the ] and ] ]s through the hydrolysis of ]:
	:{{chem2\|CH2~~=CHCH2Cl~~ + NaOH -> CH2~~=CHCH2OH~~ + NaCl}}		:{{chem2\|CH2\dCHCH2Cl + NaOH -> CH2\dCHCH2OH + NaCl}}
	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 ]:		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 ]:
	:{{chem2\|CH2~~=CHCH3~~ + 1/2 O2 + CH3CO2H -> CH2~~=CHCH2O2CCH3~~ + H2O}}		:{{chem2\|CH2\dCHCH3 + 1/2 O2 + CH3CO2H -> CH2\dCHCH2O2CCH3 + H2O}}
	Hydrolysis of this acetate gives allyl alcohol. In alternative fashion, ] can be oxidized to ], which upon ] gives the alcohol.		Hydrolysis of this acetate gives allyl alcohol. In alternative fashion, ] can be oxidized to ], which upon ] gives the alcohol.

	In principle, allyl alcohol can be obtained by ] of ].		In principle, allyl alcohol can be obtained by ] of ].

	===Laboratory methods===		===Laboratory methods===
	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>		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>

	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 ].		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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	==Applications==		==Applications==
	Allyl alcohol is converted mainly to ], which is a ] in the synthesis of ], glycidyl ethers, ], and ]. Also, a variety of ] esters are prepared from allyl alcohol, e.g. diallyl ].<ref name=Ullmann/>		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/>

			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" />
	Allyl alcohol can both '''enhance and inhibit the growth of ]''', which depends on the ] and ].

			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>
	Allyl alcohol is a ] (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>), ] (toxic to numerous unrelated ]; inhibiting the growth of such ] as ]<ref name=":0" />, ], ], ], ]<ref name=":2">{{Cite journal \|last1=Huang \|first1=H.C. \|last2=Huang \|first2=J. \|last3=Saindon \|first3=G. \|last4=Erickson \|first4=R.S. \|date=March 1997 \|title=Effect of allyl alcohol and fermented agricultural wastes on carpogenic germination of sclerotia of Sclerotinia sclerotiorum and colonization by Trichoderma spp. \|url=http://www.tandfonline.com/doi/abs/10.1080/07060669709500570 \|journal=Canadian Journal of Plant Pathology \|language=en \|volume=19 \|issue=1 \|pages=43–46 \|doi=10.1080/07060669709500570 \|bibcode=1997CaJPP..19...43H \|issn=0706-0661}}</ref>), ]. It is rapidly detoxified in ] (the treatment with allyl alcohol did not destroy the ] so completely<ref name=":1" />), and inhibitory effects in studies were absent after 4 ] on ], and after 4-8 days on ] ].<ref name=":2" />
			:{{chem2\|CH2\dCHCH2OH + HBr → CH2\dCHCH2Br + H2O}}

	Application of allyl alcohol to soils free from ] resulted in an '''increased growth of ] seedlings and improvement of their ] ]'''<ref name=":2" /> (allyl alcohol retards the fungal ], has stimulatory effects on ] and has little effect on the formation of ], causing abnormalities in the structure of the mycorrhizae<ref name=":1" />). Allyl alcohol was '''stimulatory to such beneficial fungi as ] spp.'''<ref name=":2" /> Trichoderma has proved to be able to utilize allyl alcohol as a ].<ref name=":1" /> Many species of Trichoderma have been reported as ] of ], including the ] ], hence allyl alcohol may have potential for use as a '''soil amendment for enhancing ] of ] caused by ] or ]'''. ], which only occurred sporadically in the ] and other treatments in one ], became the overwhelmingly ] ] after allyl alcohol treatment. The ] of Trichoderma continued even through the second ]<ref name=":1" />. Trichoderma sp. PDR1-7 can be utile for '''pine ] and ]''' of ]-] ] soil<ref>{{Cite journal \|last1=Babu \|first1=A. Giridhar \|last2=Shea \|first2=Patrick J. \|last3=Oh \|first3=Byung-Taek \|date=2014-04-01 \|title=Trichoderma sp. PDR1-7 promotes Pinus sylvestris reforestation of lead-contaminated mine tailing sites \|url=https://www.sciencedirect.com/science/article/pii/S0048969713016112 \|journal=Science of the Total Environment \|volume=476-477 \|pages=561–567 \|doi=10.1016/j.scitotenv.2013.12.119 \|pmid=24496029 \|bibcode=2014ScTEn.476..561B \|issn=0048-9697}}</ref>. Allyl alcohol also '''increased ] ]''' (especially such beneficial<ref name=":3">{{Cite web \|last=Hewavitharana \|first=Shashika \|date=2013 \|title=Carbon source dependent efficacy of anaerobic soil disinfestation in controlling apple replant disease \|url=https://rex.libraries.wsu.edu/esploro/outputs/99900525080301842/filesAndLinks?institution=01ALLIANCE_WSU&skipUsageReporting=true&recordUsage=false&index=0 \|access-date=2024-01-24 \|website=rex.libraries.wsu.edu}}</ref> as ] and ]<ref name=":2" /><ref name=":3" />).

	==Safety==		==Safety==
	Allyl alcohol is ~~more ], especially~~ ] ~~(in~~ ], '']'', allyl alcohol is ] by ] ] to ]; ~~causes~~ ~~severe~~ ] to the ] of rat ] ] and depletion of ]<ref name=":0" />) 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/>		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/>

	A well-researched mechanism of allyl alcohol ] is by its ] of ] after its ] to the toxic ] ]<ref name=":0" />. ] is also known to deplete ] stores of ] and cause ]. This affects the ] of the ] and consequently undermines the ] of the cell<ref name=":0" />.

	Allyl alcohol decreases both ] and ] ] of ], depletion of ], the ] for ], would diminish the recovery of the ] ] in both ]. As allyl alcohol depletes ], one might predict an increase in ].<ref name=":0" />

	==See also==		==See also==

Latest revision as of 22:12, 17 December 2024

Organic compound (CH2=CHCH2OH)

Allyl alcohol
Names


Preferred IUPAC name Prop-2-en-1-ol
Other names Allyl alcohol 2-Propen-1-ol 1-Propen-3-ol Vinyl carbinol Allylic alcohol Weed drench
Identifiers
CAS Number	107-18-6
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16605
ChEMBL	ChEMBL234926
ChemSpider	13872989
ECHA InfoCard	100.003.156
EC Number	203-470-7
KEGG	C02001
PubChem CID	7858
RTECS number	BA5075000
UNII	3W678R12M0
UN number	1098
CompTox Dashboard (EPA)	DTXSID8020044
InChI InChI=1S/C3H6O/c1-2-3-4/h2,4H,1,3H2Key: XXROGKLTLUQVRX-UHFFFAOYSA-N InChI=1/C3H6O/c1-2-3-4/h2,4H,1,3H2Key: XXROGKLTLUQVRX-UHFFFAOYAC
SMILES C=CCO
Properties
Chemical formula	C₃H₆O
Molar mass	58.080 g·mol
Appearance	colorless liquid
Odor	mustard-like
Density	0.854 g/ml
Melting point	−129 °C
Boiling point	97 °C (207 °F; 370 K)
Solubility in water	Miscible
Vapor pressure	17 mmHg
Acidity (pK_a)	15.5 (H₂O)
Magnetic susceptibility (χ)	-36.70·10 cm/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Highly toxic, lachrymator
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H301, H302, H311, H315, H319, H331, H335, H400
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)	3 3 1
Flash point	21 °C (70 °F; 294 K)
Autoignition temperature	378 °C (712 °F; 651 K)
Explosive limits	2.5–18.0%
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	80 mg/kg (rat, orally)
LC₅₀ (median concentration)	1000 ppm (mammal, 1 hr) 76 ppm (rat, 8 hr) 207 ppm (mouse, 2 hr) 1000 ppm (rabbit, 3.5 hr) 1000 ppm (monkey, 4 hr) 1060 ppm (rat, 1 hr) 165 ppm (rat, 4 hr) 76 ppm (rat, 8 hr)
NIOSH (US health exposure limits):
PEL (Permissible)	2 ppm
REL (Recommended)	TWA 2 ppm (5 mg/m) ST 4 ppm (10 mg/m)
IDLH (Immediate danger)	20 ppm
Safety data sheet (SDS)	External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Allyl alcohol (IUPAC name: prop-2-en-1-ol) is an organic compound with the structural formula CH₂=CHCH₂OH. 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. 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:

CH₂=CHCH₂Cl + NaOH → CH₂=CHCH₂OH + 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:

CH₂=CHCH₃ + 1/₂ O₂ + CH₃CO₂H → CH₂=CHCH₂O₂CCH₃ + 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.

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. Today a Allyl alcohol can be formed after 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).

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.

Allyl alcohol has herbicidal activity and can be used as a weed eradicant) and fungicide.

Allyl alcohol is the precursor in the commercial synthesis of allyl bromide:

CH₂=CHCH₂OH + HBr → CH₂=CHCH₂Br + 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. It is significantly more toxic than related alcohols. Its threshold limit value (TLV) is 2 ppm. It is a lachrymator.

References

^ NIOSH Pocket Guide to Chemical Hazards. "#0017". National Institute for Occupational Safety and Health (NIOSH).
Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–88. ISBN 978-1498754286.
Allyl alcohol toxicity
"Allyl alcohol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ Ludger Krähling; Jürgen Krey; Gerald Jakobson; Johann Grolig; Leopold Miksche (2002). "Allyl Compounds". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_425. ISBN 978-3527306732.
Oliver Kamm & C. S. Marvel (1941). "Allyl alcohol". Organic Syntheses. 1: 15. doi:10.15227/orgsyn.001.0015.
Cohen, Julius (1900). Practical Organic Chemistry (2nd ed.). London: Macmillan and Co., Limited. p. 96. Practical Organic Chemistry Cohen Julius.
^ Lemar, Katey M.; Passa, Ourania; Aon, Miguel A.; Cortassa, Sonia; Müller, Carsten T.; Plummer, Sue; O'Rourke, Brian; Lloyd, David (2005). "Allyl alcohol and garlic (Allium sativum) extract produce oxidative stress in Candida albicans". Microbiology. 151 (10): 3257–3265. doi:10.1099/mic.0.28095-0. ISSN 1465-2080. PMC 2711876. PMID 16207909.
Laiho Mikola, O.P. "Studies on the effect of some eradicants on mycorrhizal development in forest nurseries" (PDF). helda.helsinki.fi. Retrieved 2024-01-24.
Yoffe, David; Frim, Ron; Ukeles, Shmuel D.; Dagani, Michael J.; Barda, Henry J.; Benya, Theodore J.; Sanders, David C. (2013). "Bromine Compounds". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–31. doi:10.1002/14356007.a04_405.pub2. ISBN 978-3-527-30385-4.
"National Technical Information Service". US Environmental Protection Agency. 1984.

External links

International Chemical Safety Card 0095
NIOSH Pocket Guide to Chemical Hazards. "#0017". National Institute for Occupational Safety and Health (NIOSH).
Institut national de recherche et de sécurité (2004). "Alcool allylique." Fiche toxicologique n° 156. Paris:INRS. (in French)
State of Michigan public information on allyl alcohol
Occupational exposure guidelines

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