Organic compound (CH2=CHCH2OH)
Allyl alcohol
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Other names
Identifiers
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.156
EC Number
KEGG
RTECS number
UNII
UN number
1098
InChI=1S/C3H6O/c1-2-3-4/h2,4H,1,3H2
Y Key: XXROGKLTLUQVRX-UHFFFAOYSA-N
Y InChI=1/C3H6O/c1-2-3-4/h2,4H,1,3H2
Key: XXROGKLTLUQVRX-UHFFFAOYAC
Properties
C 3 H 6 O
Molar mass
−1
Appearance
colorless liquid[ 1]
Odor
mustard-like[ 1]
Density
0.854 g/ml
Melting point
−129 °C
Boiling point
97 °C (207 °F; 370 K)
Miscible
Vapor pressure
17 mmHg[ 1]
Acidity (pK a )
15.5 (H2 O)[ 2]
-36.70·10−6 cm3 /mol
Hazards
Occupational safety and health
Main hazards
Highly toxic, lachrymator
GHS labelling
Danger
H225 , H301 , H302 , H311 , H315 , H319 , H331 , H335 , H400
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
Flash point
21 °C (70 °F; 294 K)
378 °C (712 °F; 651 K)
Explosive limits
2.5–18.0%
Lethal dose or concentration (LD, LC):
80 mg/kg (rat, orally)[ 3]
1000 ppm (mammal, 1 hr)[ 4]
NIOSH
2 ppm[ 1]
TWA 2 ppm (5 mg/m3 ) ST 4 ppm (10 mg/m3 ) [skin] [ 1]
20 ppm[ 1]
Safety data sheet (SDS)
External MSDS
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Allyl alcohol (IUPAC name : prop-2-en-1-ol ) is an organic compound with the structural formula CH2 =CHCH2 OH . 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 .[ 5] allylic alcohols .
Production
Allyl alcohol is produced commercially by the Olin and Shell corporations through the hydrolysis of allyl chloride :
CH2 =CHCH2 Cl + NaOH → CH2 =CHCH2 OH + 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 + CH3 CO2 H → CH2 =CHCH2 O2 CCH3 + H2 O 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.[ 6] [ 7]
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 .[ 5] 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 ).[ 8]
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 .[ 5]
Allyl alcohol has herbicidal activity and can be used as a weed eradicant[ 9] fungicide .[ 8]
Allyl alcohol is the precursor in the commercial synthesis of allyl bromide :[ 10]
CH2 =CHCH2 OH + HBr → CH2 =CHCH2 Br + H2 O
Safety
Allyl alcohol is hepatotoxic . In rats , in vivo metabolized by liver alcohol dehydrogenase to acrolein , which can cause damage to the microtubules of rat hepatocyte mitochondria and depletion of glutathione .[ 8] [ 5] [ 11] lachrymator .[ 5]
See also
References
^ a b c d e f g h 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 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).^ a b c d e Ludger Krähling; Jürgen Krey; Gerald Jakobson; Johann Grolig; Leopold Miksche (2002). "Allyl Compounds". Ullmann's Encyclopedia of Industrial Chemistry 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 96 . Practical Organic Chemistry Cohen Julius. ^ a b c 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
