Allyl alcohol (
IUPAC name
In chemical nomenclature, a preferred IUPAC name (PIN) is a unique name, assigned to a chemical substance and preferred among all possible names generated by IUPAC nomenclature. The "preferred IUPAC nomenclature" provides a set of rules for choos ...
: prop-2-en-1-ol) is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the
structural formula
The structural formula of a chemical compound is a graphic representation of the molecular structure (determined by structural chemistry methods), showing how the atoms are connected to one another. The chemical bonding within the molecule is al ...
. Like many
alcohol
Alcohol may refer to:
Common uses
* Alcohol (chemistry), a class of compounds
* Ethanol, one of several alcohols, commonly known as alcohol in everyday life
** Alcohol (drug), intoxicant found in alcoholic beverages
** Alcoholic beverage, an alco ...
s, 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
A plasticizer (British English, UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity (physics), plasticity, to decrease its viscosity, and/or to decrease friction during its ...
.
Allyl alcohol is the smallest representative of the
allyl
In organic chemistry, an allyl group is a substituent with the structural formula . It consists of a methylene bridge () attached to a vinyl group (). The name is derived from the scientific name for garlic, . In 1844, Theodor Wertheim isolated a ...
ic
alcohol
Alcohol may refer to:
Common uses
* Alcohol (chemistry), a class of compounds
* Ethanol, one of several alcohols, commonly known as alcohol in everyday life
** Alcohol (drug), intoxicant found in alcoholic beverages
** Alcoholic beverage, an alco ...
s.
Production
Allyl alcohol is produced commercially by the
Olin Olin may refer to:
People
Organizations
* OLIN, American landscape architecture firm
* Olin Business School at Washington University in St. Louis
* Olin College, an undergraduate engineering college in Massachusetts
* Olin Corporation, a chem ...
and
Shell
Shell may refer to:
Architecture and design
* Shell (structure), a thin structure
** Concrete shell, a thin shell of concrete, usually with no interior columns or exterior buttresses
Science Biology
* Seashell, a hard outer layer of a marine ani ...
corporation
A corporation or body corporate is an individual or a group of people, such as an association or company, that has been authorized by the State (polity), state to act as a single entity (a legal entity recognized by private and public law as ...
s through the hydrolysis of
allyl chloride
Allyl chloride is the organic compound with the formula C H2=CHCH2 Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a c ...
:
:
Allyl alcohol can also be made by the rearrangement of
propylene oxide
Propylene oxide is an epoxide with the molecular formula C3H6O. This colourless volatile liquid with an odour similar to ether, is produced on a large scale industrially. Its major application is its use for the production of polyether polyols f ...
, a reaction that is catalyzed by
potassium alum
Potassium alum, potash alum, or potassium aluminium sulfate is a chemical compound defined as the double sulfate of potassium and aluminium, with chemical formula KAl(SO4)2. It is commonly encountered as the dodecahydrate, KAl(SO4)2·12H2O. It ...
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
Propylene, also known as propene, is an unsaturated organic compound with the chemical formula . It has one double bond, and is the second simplest member of the alkene class of hydrocarbons. It is a colorless gas with a faint petroleum-like o ...
to
allyl acetate:
:
Hydrolysis of this acetate gives allyl alcohol. In alternative fashion,
propylene
Propylene, also known as propene, is an unsaturated organic compound with the chemical formula . It has one double bond, and is the second simplest member of the alkene class of hydrocarbons. It is a colorless gas with a faint petroleum-like o ...
can be oxidized to
acrolein, which upon
hydrogenation
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...
gives the alcohol.
In principle, allyl alcohol can be obtained by
dehydrogenation
In chemistry, dehydrogenation is a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. At ...
of
propanol
There are two isomers of propanol.
* 1-Propanol, ''n''-propanol, or propan-1-ol: CH3CH2CH2OH, the most common meaning
*2-Propanol, isopropyl alcohol, isopropanol, or propan-2-ol: (CH3)2CHOH
See also
* Propanal (propionaldehyde) differs in spel ...
.
Laboratory methods
In the laboratory,
glycerol
Glycerol () is a simple triol compound. It is a colorless, odorless, sweet-tasting, viscous liquid. The glycerol backbone is found in lipids known as glycerides. It is also widely used as a sweetener in the food industry and as a humectant in pha ...
reacts with
oxalic or
formic acid
Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid. It has the chemical formula HCOOH and structure . This acid is an important intermediate in chemical synthesis and occurs naturally, most notably in some an ...
s to give (respectively)
dioxalin
Dioxalin is a reaction product of glycerol with oxalic acid at 533 Kelvin, K. Its IUPAC nomenclature, IUPAC name is 5-(hydroxymethyl)-1,4-dioxane-2,3-dione. Dioxalin readily loses two molecules of carbon dioxide at this high temperature to form ...
or glyceric formate, either of which
decarboxylate
Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is ...
and
dehydrate to allylol.
Allyl alcohols in general are prepared by
allylic oxidation
In organic chemistry, an allyl group is a substituent with the structural formula . It consists of a methylene bridge () attached to a vinyl group (). The name is derived from the scientific name for garlic, . In 1844, Theodor Wertheim isola ...
of
allyl
In organic chemistry, an allyl group is a substituent with the structural formula . It consists of a methylene bridge () attached to a vinyl group (). The name is derived from the scientific name for garlic, . In 1844, Theodor Wertheim isolated a ...
compounds, using
selenium dioxide
Selenium dioxide is the chemical compound with the formula SeO2. This colorless solid is one of the most frequently encountered compounds of selenium. It is used in making specialized glasses as well as a reagent in organic chemistry.
Properties ...
or
organic peroxide
In organic chemistry, organic peroxides are organic compounds containing the peroxide functional group (). If the R′ is hydrogen, the compounds are called hydroperoxides, which are discussed in that article. The O−O bond of peroxides easily b ...
s. Other methods include carbon-carbon bond-forming reactions such as the
Prins reaction
The Prins reaction is an organic reaction consisting of an electrophilic addition of an aldehyde or ketone to an alkene or alkyne followed by capture of a nucleophile or elimination of an H+ ion. The outcome of the reaction depends on react ...
, 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
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...
of
allyl iodide.
Today a
Allyl alcohol can be formed after
trituration
Trituration (Latin, ''grinding'') is the name of several different methods used to process materials. In one sense, it is a form of comminution (reducing the particle size of a substance). In another sense, it is the production of a homogeneous pow ...
of
garlic (Allium sativum) cloves (producing from garlic in two ways: firstly by a
self-condensation reaction of
allicin
Allicin is an organosulfur compound obtained from garlic and leeks. When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic. Allicin is unstable and quickl ...
and its
decomposition
Decomposition is the process by which dead organic substances are broken down into simpler organic or inorganic matter such as carbon dioxide, water, simple sugars and mineral salts. The process is a part of the nutrient cycle and is ess ...
products such as
diallyl trisulphide and
diallyl disulphide and secondly by the
reaction
Reaction may refer to a process or to a response to an action, event, or exposure.
Physics and chemistry
*Chemical reaction
*Nuclear reaction
*Reaction (physics), as defined by Newton's third law
* Chain reaction (disambiguation)
Biology and ...
between
alliin
Alliin is a sulfoxide that is a natural constituent of fresh garlic. It is a derivative of the amino acid cysteine. When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma o ...
, the
precursor of
allicin
Allicin is an organosulfur compound obtained from garlic and leeks. When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic. Allicin is unstable and quickl ...
, and
water
Water is an inorganic compound with the chemical formula . It is a transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance. It is the main constituent of Earth's hydrosphere and the fluids of all known liv ...
).
Applications
Allyl alcohol is converted mainly to
glycidol, which is a
chemical intermediate in the synthesis of
glycerol
Glycerol () is a simple triol compound. It is a colorless, odorless, sweet-tasting, viscous liquid. The glycerol backbone is found in lipids known as glycerides. It is also widely used as a sweetener in the food industry and as a humectant in pha ...
, glycidyl ethers,
ester
In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
s, and
amine
In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...
s. Also, a variety of
polymer
A polymer () is a chemical substance, substance or material that consists of very large molecules, or macromolecules, that are constituted by many repeat unit, repeating subunits derived from one or more species of monomers. Due to their br ...
izable esters are prepared from allyl alcohol, e.g. diallyl
phthalate
Phthalates ( ), or phthalate esters, are esters of phthalic acid. They are mainly used as plasticizers, i.e., substances added to plastics to increase their flexibility, transparency, durability, and longevity. They are used primarily to soften ...
.
[
Allyl alcohol has herbicidal activity and can be used as a ]weed
A weed is a plant considered undesirable in a particular situation, growing where it conflicts with human preferences, needs, or goals.Harlan, J. R., & deWet, J. M. (1965). Some thoughts about weeds. ''Economic botany'', ''19''(1), 16-24. Pla ...
eradicant) and fungicide
Fungicides are pesticides used to kill parasitic fungi or their spores. Fungi can cause serious damage in agriculture, resulting in losses of yield and quality. Fungicides are used both in agriculture and to fight fungal infections in animals, ...
.
Allyl alcohol is the precursor in the commercial synthesis of allyl bromide:
:
Safety
Allyl alcohol is hepatotoxic
Hepatotoxicity (from ''hepatic toxicity'') implies chemical-driven liver damage. Drug-induced liver injury (DILI) is a cause of acute and chronic liver disease caused specifically by medications and the most common reason for a drug to be withdr ...
. In rat
Rats are various medium-sized, long-tailed rodents. Species of rats are found throughout the order Rodentia, but stereotypical rats are found in the genus ''Rattus''. Other rat genera include '' Neotoma'' (pack rats), '' Bandicota'' (bandicoo ...
s, ''in vivo
Studies that are ''in vivo'' (Latin for "within the living"; often not italicized in English) are those in which the effects of various biological entities are tested on whole, living organisms or cells, usually animals, including humans, an ...
'', allyl alcohol is metabolized
Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the co ...
by liver
The liver is a major metabolic organ (anatomy), organ exclusively found in vertebrates, which performs many essential biological Function (biology), functions such as detoxification of the organism, and the Protein biosynthesis, synthesis of var ...
alcohol dehydrogenase
Alcohol dehydrogenases (ADH) () are a group of dehydrogenase enzymes that occur in many organisms and facilitate the interconversion between alcohols and aldehydes or ketones with the reduction of nicotinamide adenine dinucleotide (NAD+) to N ...
to acrolein, which can cause damage
Damage is any change in a thing, often a physical object, that degrades it away from its initial state. It can broadly be defined as "changes introduced into a system that adversely affect its current or future performance".Farrar, C.R., Sohn, H., ...
to the microtubule
Microtubules are polymers of tubulin that form part of the cytoskeleton and provide structure and shape to eukaryotic cells. Microtubules can be as long as 50 micrometres, as wide as 23 to 27 nanometer, nm and have an inner diameter bet ...
s of rat hepatocyte
A hepatocyte is a cell of the main parenchymal tissue of the liver. Hepatocytes make up 80% of the liver's mass.
These cells are involved in:
* Protein synthesis
* Protein storage
* Transformation of carbohydrates
* Synthesis of cholesterol, bi ...
mitochondria
A mitochondrion () is an organelle found in the cells of most eukaryotes, such as animals, plants and fungi. Mitochondria have a double membrane structure and use aerobic respiration to generate adenosine triphosphate (ATP), which is us ...
and depletion of glutathione
Glutathione (GSH, ) is an organic compound with the chemical formula . It is an antioxidant in plants, animals, fungi, and some bacteria and archaea. Glutathione is capable of preventing damage to important cellular components caused by sources ...
. It is significantly more toxic than related alcohols. Its threshold limit value (TLV) is 2 ppm. It is a lachrymator.[
]
See also
* Propargyl alcohol
Propargyl alcohol, or 2-propyn-1-ol, is an organic compound with the formula C3H4O. It is the simplest stable alcohol containing an alkyne functional group. Propargyl alcohol is a colorless viscous liquid that is miscible with water and most pol ...
References
External links
*
*
*
State of Michigan public information on allyl alcohol
Occupational exposure guidelines
{{Authority control
Primary alcohols
Allyl compounds
Hepatotoxins
Substances discovered in the 19th century