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Denatured alcohol (also called methylated spirits in Australia, Canada, Ireland, New Zealand, South Africa, and the United Kingdom; wood spirit; and denatured rectified spirit) is
ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a h ...
that has additives to make it
poison Poison is a chemical substance that has a detrimental effect to life. The term is used in a wide range of scientific fields and industries, where it is often specifically defined. It may also be applied colloquially or figuratively, with a broa ...
ous, bad-tasting, foul-smelling, or nauseating to discourage its recreational consumption. It is sometimes dyed so that it can be identified visually.
Pyridine Pyridine is a basic (chemistry), basic heterocyclic compound, heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakl ...
and methanol, each and together, make denatured alcohol poisonous; and denatonium makes it bitter. Denatured alcohol is used as a
solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
and as fuel for
alcohol burner An alcohol burner or spirit lamp is a piece of laboratory equipment used to produce an open flame. It can be made from brass, glass, stainless steel or aluminium. Uses Alcohol burners are preferred for some uses over Bunsen burners for safety pu ...
s and camping stoves. Because of the diversity of industrial uses for denatured alcohol, hundreds of additives and denaturing methods have been used. The main additive usually is 10% methanol (methyl alcohol), hence the name ''methylated spirits''. Other common additives include
isopropyl alcohol Isopropyl alcohol (IUPAC name propan-2-ol and also called isopropanol or 2-propanol) is a colorless, flammable organic compound with a pungent alcoholic odor. As an isopropyl group linked to a hydroxyl group (chemical formula ) it is the simp ...
,
acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscible wi ...
,
methyl ethyl ketone Butanone, also known as methyl ethyl ketone (MEK), is an organic compound with the formula CH3C(O)CH2CH3. This colourless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in na ...
, and methyl isobutyl ketone. Denatured alcohol blends average 60 to 90% ethanol. Denaturing alcohol does not alter the ethanol molecule (
chemically A chemical reaction is a process that leads to the IUPAC nomenclature for organic transformations, chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the pos ...
or structurally), unlike denaturation in biochemistry. Rather, the ethanol is mixed with other chemicals to form a foul-tasting, often toxic, solution. For many of these solutions, it is intentionally difficult to separate the components.


Uses

In many countries, sales of alcoholic beverages are heavily taxed for revenue and public health policy purposes (see
Pigovian tax A Pigouvian tax (also spelled Pigovian tax) is a tax on any market activity that generates negative externalities (i.e., external costs incurred by the producer that are not included in the market price). The tax is normally set by the governm ...
). In order to avoid paying beverage taxes on alcohol that is not meant to be consumed, the alcohol must be "denatured", or treated with added chemicals to make it unpalatable. Its composition is tightly defined by government regulations in countries that tax alcoholic beverages. Denatured alcohol is used identically to ethanol itself except for applications that involve fuel, surgical and laboratory stock. Pure ethanol is required for food and beverage applications and certain chemical reactions where the denaturant would interfere. In
molecular biology Molecular biology is the branch of biology that seeks to understand the molecular basis of biological activity in and between cells, including biomolecular synthesis, modification, mechanisms, and interactions. The study of chemical and phys ...
, denatured ethanol should not be used for the
precipitation In meteorology, precipitation is any product of the condensation of atmospheric water vapor that falls under gravitational pull from clouds. The main forms of precipitation include drizzle, rain, sleet, snow, ice pellets, graupel and hai ...
of
nucleic acid Nucleic acids are biopolymers, macromolecules, essential to all known forms of life. They are composed of nucleotides, which are the monomers made of three components: a 5-carbon sugar, a phosphate group and a nitrogenous base. The two main ...
s, since the additives may interfere with downstream applications. Denatured alcohol has no advantages for any purpose over normal ethanol; it is a public policy compromise. As denatured alcohol is sold without the often heavy taxes on alcohol suitable for consumption, it is a cheaper solution for most uses that do not involve drinking. If pure ethanol were made cheaply available for fuel, solvents, or medicinal purposes, it would likely be enjoyed as a drink by many people without payment of alcoholic beverage taxes.


Toxicity

Despite its poisonous content, denatured alcohol is sometimes consumed as a surrogate alcohol. This can result in blindness or death if it contains methanol. For instance, during the Prohibition in the United States, federal law required methanol in domestically manufactured industrial alcohols. From 25–27 December 1926, which was roughly at the midpoint of the "Noble Experiment" of nationwide alcohol prohibition, 31 people in New York City alone died of methanol poisoning. To help prevent this, denatonium is often added to give the substance an extremely bitter flavour. Substances such as
pyridine Pyridine is a basic (chemistry), basic heterocyclic compound, heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakl ...
are added to give the mixture an unpleasant odour, and agents such as syrup of ipecac may also be included to induce vomiting. New Zealand has removed methanol from its government-approved "methylated spirits" formulation. In the
USSR The Soviet Union,. officially the Union of Soviet Socialist Republics. (USSR),. was a transcontinental country that spanned much of Eurasia from 1922 to 1991. A flagship communist state, it was nominally a federal union of fifteen nation ...
, denatured alcohol was used as drinking alcohol surrogate, along with many other technical ethanol-containing products. This was especially common during various anti-alcohol campaigns initiated by the Soviet government. There is much evidence to that in both popular folklore and in literature and music. The word “denaturat” (Russian: денатурат) even gained a special symbolic meaning. Its consumption is mentioned in songs of
Vladimir Vysotsky Vladimir Semyonovich Vysotsky ( rus, links=no, Владимир Семёнович Высоцкий, p=vlɐˈdʲimʲɪr sʲɪˈmʲɵnəvʲɪtɕ vɨˈsotskʲɪj; 25 January 1938 – 25 July 1980), was a Soviet singer-songwriter, poet, and actor ...
, as well as written works of Venedikt Yerofeev, Yuz Aleshkovsky, and Vyacheslav Shishkov.


Formulations

Diverse additives are used to make it difficult to use
distillation Distillation, or classical distillation, is the process of separating the components or substances from a liquid mixture by using selective boiling and condensation, usually inside an apparatus known as a still. Dry distillation is the he ...
or other simple processes to reverse the denaturation. Methanol is commonly used both because its boiling point is close to that of ethanol and because it is toxic. Another typical denaturant is pyridine. Often the denatured alcohol is dyed with
methyl violet Methyl violet is a family of organic compounds that are mainly used as dyes. Depending on the number of attached methyl groups, the color of the dye can be altered. Its main use is as a purple dye for textiles and to give deep violet colors in pai ...
.Naim Kosaric, Zdravko Duvnjak, Adalbert Farkas, Hermann Sahm, Stephanie Bringer-Meyer, Otto Goebel and Dieter Mayer in "Ethanol" Ullmann's Encyclopedia of Industrial Chemistry, 2011, Wiley-VCH, Weinheim. There are several grades of denatured alcohol, but in general the denaturants used are similar. As an example, the formulation for ''completely denatured alcohol'', according to 2005 British regulations was as follows: The European Union agreed in February 2013 to the mutual procedures for the complete denaturing of alcohol:


Specially denatured alcohol

A specially denatured alcohol (SDA) is one of many types of denatured alcohol specified under the United States
Title 27 of the Code of Federal Regulations CFR Title 27 – Alcohol, Tobacco Products and Firearms is one of 50 titles composing the United States Code of Federal Regulations (CFR) and contains the principal set of rules and regulations issued by federal agencies regarding alcohol, tobacco p ...
Section 21.151. A specially denatured alcohol is a combination of ethanol and another chemical substance, e.g.,
ethyl acetate Ethyl acetate ( systematically ethyl ethanoate, commonly abbreviated EtOAc, ETAC or EA) is the organic compound with the formula , simplified to . This colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues ...
in SDA 29, 35, and 35A, added to render the mixture unsuitable for drinking. SDAs are often used in cosmetic products, and can also be used in chemical manufacturing, pharmaceuticals, and solvents. Another example is SDA 40-B, which contains tert-butyl alcohol and denatonium benzoate, N.F. In the United States and other countries, the use of denatured alcohol unsuitable for beverages avoids
excise file:Lincoln Beer Stamp 1871.JPG, upright=1.2, 1871 U.S. Revenue stamp for 1/6 barrel of beer. Brewers would receive the stamp sheets, cut them into individual stamps, cancel them, and paste them over the Bunghole, bung of the beer barrel so when ...
taxes on alcohol.2004 CFR Title 27, Volume 1
. access.gpo.gov. Retrieved on 29 May 2011.


See also

* Aversive agent * Bitterant *
Isopropyl alcohol Isopropyl alcohol (IUPAC name propan-2-ol and also called isopropanol or 2-propanol) is a colorless, flammable organic compound with a pungent alcoholic odor. As an isopropyl group linked to a hydroxyl group (chemical formula ) it is the simp ...
*
Rubbing alcohol Rubbing alcohol is either an isopropyl alcohol or an ethanol-based liquid, with isopropyl alcohol products being the most widely available. The comparable ''British Pharmacopoeia'' (''BP'') is surgical spirit. Rubbing alcohol is denatured and un ...
* E85


References


External links

{{Commons category, Denatured alcohol
27 CFR 20, regulations relating to denatured alcohol in the United States

Specifications and licensing of methylated spirits in the United Kingdom

European Community COMMISSION REGULATION (EC) No 162/2013 on the mutual recognition of procedures for the complete denaturing of alcohol for the purposes of exemption from excise duty
*
HM Revenue and Customs HM Revenue and Customs (His Majesty's Revenue and Customs, or HMRC) is a non-ministerial government department, non-ministerial Departments of the United Kingdom Government, department of the His Majesty's Government, UK Government responsible fo ...

Production, distribution and use of denatured alcohol

"List of SDAs with denaturing chemical"
Alcohols Alcohol solvents Excipients Product safety Methanol Adulteration ja:エタノール#利用