Allyl alcohol: Difference between revisions

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	\| 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/>		\| 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
	\| Section1 = {{Chembox Identifiers		\| Section1 = {{Chembox Identifiers
	\| PubChem = 7858		\| PubChem = 7858
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	}}		}}
	\| Section3 = {{Chembox Hazards		\| Section3 = {{Chembox Hazards
			\| MainHazards= Highly toxic, lachrymator
	\| ExternalSDS =		\| ExternalSDS =
	\| NFPA-H=3		\| NFPA-H=3
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	\| GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}}{{GHS09}}		\| GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}}{{GHS09}}
	\| GHSSignalWord = Danger		\| GHSSignalWord = Danger
	\| HPhrases = {{H-phrases\|225\|301\|311\|315\|319\|331\|335\|400}}		\| 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}}		\| 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		\| FlashPtC = 21
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	\| IDLH = 20 ppm<ref name=NIOSH/>		\| 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>) <ref name=NIOSH/>		\| REL = TWA 2 ppm (5 mg/m<sup>3</sup>) ST 4 ppm (10 mg/m<sup>3</sup>) <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>		\| 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''' (] name: '''prop-2-en-1-ol''') is an ] with the ] CH<sub>2</sub>=CHCH<sub>2</sub>OH. Like many ]s, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a raw material for the production of glycerol, but is also used as a precursor 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.		'''Allyl alcohol''' (] name: '''prop-2-en-1-ol''') is an ] with the ] CH<sub>2</sub>=CHCH<sub>2</sub>OH. Like many ]s, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a raw material for the production of ], but is also used as a precursor 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.

	==Production==		==Production==

Revision as of 16:43, 23 July 2022

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 raw material for the production of glycerol, but is also 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 can be obtained by many methods. It was first prepared in 1856 by Auguste Cahours and August Hofmann by hydrolysis of allyl iodide. Today 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 + CH₃COOH → CH₂=CHCH₂OCOCH₃ + H₂O

Hydrolysis of this acetate gives allyl alcohol. In alternative fashion, propylene can be oxidized to acrolein, which upon hydrogenation gives the alcohol.

Other methods

In principle, allyl alcohol can be obtained by dehydrogenation of propanol. In the laboratory, it has been prepared by the reaction of glycerol with oxalic or formic acids. Allyl alcohols in general can be prepared by allylic oxidation of allyl compounds by selenium dioxide.

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.

Safety

Allyl alcohol is more toxic than related alcohols. Its threshold limit value (TLV) is 2 ppm. It is a lachrymator.

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.

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. p. 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; Collected Volumes, vol. 1, p. 42.
Cohen, Julius (1900). Practical Organic Chemistry (2nd ed.). London: Macmillan and Co., Limited. p. 96. Practical Organic Chemistry Cohen Julius.
"40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011. {{cite journal}}: Cite journal requires |journal= (help)

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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