Allyl alcohol

Source: Wikipedia, the free encyclopedia.
Allyl alcohol
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Prop-2-en-1-ol
Other names
Allyl alcohol
2-Propen-1-ol
1-Propen-3-ol[1]
Vinyl carbinol[1]
Allylic alcohol
Weed drench[citation needed]
Identifiers
3D model (
JSmol
)
3DMet
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.003.156 Edit this at Wikidata
EC Number
  • 203-470-7
KEGG
RTECS number
  • BA5075000
UNII
UN number 1098
  • InChI=1S/C3H6O/c1-2-3-4/h2,4H,1,3H2 checkY
    Key: XXROGKLTLUQVRX-UHFFFAOYSA-N checkY
  • InChI=1/C3H6O/c1-2-3-4/h2,4H,1,3H2
    Key: XXROGKLTLUQVRX-UHFFFAOYAC
  • C=CCO
Properties
C3H6O
Molar mass 58.080 g·mol−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 (pKa) 15.5 (H2O)[2]
-36.70·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Highly toxic, lachrymator
GHS labelling:
GHS02: FlammableGHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
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 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
3
1
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)
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)[4]
NIOSH (US health exposure limits):
PEL (Permissible)
 2 ppm[1]
REL (Recommended)
 TWA 2 ppm (5 mg/m3) ST 4 ppm (10 mg/m3) [skin] [1]
IDLH
(Immediate danger)
 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).
☒N verify (what is checkY☒N ?)

Allyl alcohol (

allylic alcohols
.

Production

Allyl alcohol is produced commercially by the

Shell corporations through the hydrolysis of allyl chloride
:

CH2=CHCH2Cl + NaOH → CH2dCHCH2OH + 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

propanol
.

Laboratory methods

In the laboratory,

dehydrate to allylol.[6][7]

Allyl alcohols in general are prepared by

Mislow-Evans rearrangement
.

Allyl alcohol was first prepared in 1856 by Auguste Cahours and August Hofmann by hydrolysis of allyl iodide.[5] 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).[8]

Applications

Allyl alcohol is converted mainly to

phthalate.[5]

Allyl alcohol has herbicidal activity and can be used as a weed eradicant[9]) and fungicide.[8]

Safety

Allyl alcohol is

lachrymator.[5]

See also

References

  1. ^ a b c d e f g h NIOSH Pocket Guide to Chemical Hazards. "#0017". National Institute for Occupational Safety and Health (NIOSH).
  2. ISBN 978-1498754286
    .
  3. ^ Allyl alcohol toxicity
  4. ^ "Allyl alcohol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. ^
    ISBN 978-3527306732
    .
  6. doi:10.15227/orgsyn.001.0015
    .
  7. ^ Cohen, Julius (1900). Practical Organic Chemistry (2nd ed.). London: Macmillan and Co., Limited. p. 96. Practical Organic Chemistry Cohen Julius.
  8. ^
    PMID 16207909
    .
  9. ^ 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.{{cite web}}: CS1 maint: multiple names: authors list (link)
  10. ^ "National Technical Information Service". US Environmental Protection Agency. 1984.

External links

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