Alcohol

This article is about the generic chemistry term. For the kind of alcohol found in alcoholic beverages, see Ethanol. For beverages containing alcohol, see Alcoholic beverage. For other uses, see Alcohol (disambiguation).

The hydroxyl (OH) functional group in an alcohol molecule

Ball-and-stick model of the hydroxyl (OH) functional group in an alcohol molecule

In chemistry, an alcohol is an organic compound in which the hydroxy functional group (-OH) is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms.^[1]

An important class of alcohols are the simple acyclic alcohols, the general formula for which is C_nH_2n+1OH. Of those, ethanol (C₂H₅OH) is the type of alcohol found in alcoholic beverages, and in common speech the word alcohol refers specifically to ethanol.

Other alcohols are usually described with a clarifying adjective, as in isopropyl alcohol (propan-2-ol) or wood alcohol (methyl alcohol, or methanol). The suffix -ol appears in the IUPAC chemical name of all substances where the hydroxyl group is the functional group with the highest priority; in substances where a higher priority group is present the prefix hydroxy- will appear in the IUPAC name. The suffix -ol in non-systematic names (such as paracetamol or cholesterol) also typically indicates that the substance includes a hydroxyl functional group and, so, can be termed an alcohol. But many substances, particularly sugars (examples glucose and sucrose) contain hydroxyl functional groups without using the suffix.

Simple alcohols

Space filling model of the hydroxyl (OH) functional group in an alcohol molecule

The most commonly used alcohol is ethanol, C₂H₅OH, with the ethane backbone. Ethanol has been produced and consumed by humans for millennia, in the form of fermented and distilled alcoholic beverages. It is a clear flammable liquid that boils at 78.4 °C, which is used as an industrial solvent, car fuel, and raw material in the chemical industry. In the US and some other countries, because of legal and tax restrictions on alcohol consumption, ethanol destined for other uses often contains additives that make it unpalatable (such as Bitrex) or poisonous (such as methanol). Ethanol in this form is known generally as denatured alcohol; when methanol is used, it may be referred to as methylated spirits or "surgical spirits".

The simplest alcohol is methanol, CH₃OH, which was formerly obtained by the distillation of wood and, therefore, is called "wood alcohol". It is a clear liquid resembling ethanol in smell and properties, with a slightly lower boiling point (64.7 °C), and is used mainly as a solvent, fuel, and raw material. Unlike ethanol, methanol is extremely toxic: One sip (as little as 10 ml) can cause permanent blindness by destruction of the optic nerve and 30 ml (one fluid ounce) is potentially fatal.^[2]

Two other alcohols whose uses are relatively widespread (though not so much as those of methanol and ethanol) are propanol and butanol. Like ethanol, they can be produced by fermentation processes. (However, the fermenting agent is a bacterium, Clostridium acetobutylicum, that feeds on cellulose, not sugars like the Saccharomyces yeast that produces ethanol.) Saccharomyces yeast are known to produce these higher alcohols at temperatures above 75 °F (24 °C). These alcohols are called fusel alcohols or fusel oils in brewing and tend to have a spicy or peppery flavor. They are considered a fault in most styles of beer.^{[citation needed]}

Simple alcohols, in particular, ethanol and methanol, possess denaturing and inert rendering properties, leading to their use as anti-microbial agents in medicine, pharmacy, and industry.^{[citation needed]}

Nomenclature

Systematic names

In the IUPAC system, the name of the alkane chain loses the terminal "e" and adds "ol", e.g., "methanol" and "ethanol".^[3] When necessary, the position of the hydroxyl group is indicated by a number between the alkane name and the "ol": propan-1-ol for CH₃CH₂CH₂OH, propan-2-ol for CH₃CH(OH)CH₃. Sometimes, the position number is written before the IUPAC name: 1-propanol and 2-propanol. If a higher priority group is present (such as an aldehyde, ketone, or carboxylic acid), then it is necessary to use the prefix "hydroxy",^[3] for example: 1-hydroxy-2-propanone (CH₃COCH₂OH).^[4]

Some examples of simple alcohols and how to name them

The IUPAC nomenclature is used in scientific publications and where precise identification of the substance is important. In other less formal contexts, an alcohol is often called with the name of the corresponding alkyl group followed by the word "alcohol", e.g., methyl alcohol, ethyl alcohol. Propyl alcohol may be n-propyl alcohol or isopropyl alcohol, depending on whether the hydroxyl group is bonded to the 1st or 2nd carbon on the propane chain.

Alcohols are classified into primary, secondary, and tertiary, based upon the number of carbon atoms connected to the carbon atom that bears the hydroxyl group. The primary alcohols have general formulas RCH₂OH; secondary ones are RR'CHOH; and tertiary ones are RR'R"COH, where R, R', and R" stand for alkyl groups. Ethanol and n-propyl alcohol are primary alcohols; isopropyl alcohol is a secondary one. The prefixes sec- (or s-) and tert- (or t-), conventionally in italics, may be used before the alkyl group's name to distinguish secondary and tertiary alcohols, respectively, from the primary one. For example, isopropyl alcohol is occasionally called sec-propyl alcohol, and the tertiary alcohol (CH₃)₃COH, or 2-methylpropan-2-ol in IUPAC nomenclature is commonly known as tert-butyl alcohol or tert-butanol.

Common Names

Chemical Formula	IUPAC Name	Common Name
Monohydric alcohols
CH3OH	Methanol	Wood alcohol
C2H5OH	Ethanol	Grain alcohol
C3H7OH	Isopropyl alcohol	Rubbing alcohol
C5H11OH	Pentanol	Amyl alcohol
C16H33OH	Hexadecan-1-ol	Cetyl alcohol
Polyhydric alcohols
C2H4(OH)2	Ethane-1,2-diol	Ethylene glycol
C3H5(OH)3	Propane-1,2,3-triol	Glycerin
C4H6(OH)4	Butane-1,2,3,4-tetraol	Erythritol
C5H7(OH)5	Pentane-1,2,3,4,5-pentol	Xylitol
C6H8(OH)6	Hexane-1,2,3,4,5,6-hexol	Mannitol, Sorbitol
C7H9(OH)7	Heptane-1,2,3,4,5,6,7-heptol	Volemitol
Unsaturated aliphatic alcohols
C3H5OH	Prop-2-ene-1-ol	Allyl alcohol
C10H17OH	3,7-Dimethylocta-2,6-dien-1-ol	Geraniol
C3H3OH	Prop-2-in-1-ol	Propargyl alcohol
Alicyclic alcohols
C6H6(OH)6	Cyclohexane-1,2,3,4,5,6-hexol	Inositol
C10H19OH	2 - (2-propyl)-5-methyl-cyclohexane-1-ol	Menthol

Etymology

The word alcohol appears in English in the 16th century, loaned via French from medical Latin, ultimately from the Arabic الكحل (al-kuḥl, "the kohl, a powder used as an eyeliner").

ال al is Arabic for the definitive article, the in English.

The current Arabic name for alcohol is الكحول al-kuḥūl, re-introduced from western usage.

kuḥl was the name given to the very fine powder, produced by the sublimation of the natural mineral stibnite to form antimony sulfide Sb₂S₃ (hence the essence or "spirit" of the substance), which was used as an antiseptic and eyeliner.

Bartholomew Traheron in his 1543 translation of John of Vigo introduces the word as a term used by "barbarous" (Moorish) authors for "fine powder":

the barbarous auctours use alcohol, or (as I fynde it sometymes wryten) alcofoll, for moost fine poudre.

William Johnson in his 1657 Lexicon Chymicum glosses the word as antimonium sive stibium. By extension, the word came to refer to any fluid obtained by distillation, including "alcohol of wine", the distilled essence of wine. Libavius in Alchymia (1594) has vini alcohol vel vinum alcalisatum. Johnson (1657) glosses alcohol vini as quando omnis superfluitas vini a vino separatur, ita ut accensum ardeat donec totum consumatur, nihilque fæcum aut phlegmatis in fundo remaneat. The word's meaning became restricted to "spirit of wine" (ethanol) in the 18th century, and was again extended to the family of substances so called in modern chemistry from 1850.

Physical and chemical properties

Alcohols have an odor that is often described as “biting” and as “hanging” in the nasal passages. Ethanol has a slightly sweeter odor than the other alcohols.

In general, the hydroxyl group makes the alcohol molecule polar. Those groups can form hydrogen bonds to one another and to other compounds (except in certain large molecules where the hydroxyl is protected by steric hindrance of adjacent groups^[5]). This hydrogen bonding means that alcohols can be used as protic solvents. Two opposing solubility trends in alcohols are: the tendency of the polar OH to promote solubility in water, and the tendency of the carbon chain to resist it. Thus, methanol, ethanol, and propanol are miscible in water because the hydroxyl group wins out over the short carbon chain. Butanol, with a four-carbon chain, is moderately soluble because of a balance between the two trends. Alcohols of five or more carbons (pentanol and higher) are effectively insoluble in water because of the hydrocarbon chain's dominance. All simple alcohols are miscible in organic solvents.

Because of hydrogen bonding, alcohols tend to have higher boiling points than comparable hydrocarbons and ethers. The boiling point of the alcohol ethanol is 78.29 °C, compared to 69 °C for the hydrocarbon hexane (a common constituent of gasoline), and 34.6 °C for diethyl ether.

Alcohols, like water, can show either acidic or basic properties at the -OH group. With a pK_a of around 16-19, they are, in general, slightly weaker acids than water, but they are still able to react with strong bases such as sodium hydride or reactive metals such as sodium. The salts that result are called alkoxides, with the general formula RO^- M⁺.

Meanwhile, the oxygen atom has lone pairs of nonbonded electrons that render it weakly basic in the presence of strong acids such as sulfuric acid. For example, with methanol:

Alcohols can also undergo oxidation to give aldehydes, ketones, or carboxylic acids, or they can be dehydrated to alkenes. They can react to form ester compounds, and they can (if activated first) undergo nucleophilic substitution reactions. The lone pairs of electrons on the oxygen of the hydroxyl group also makes alcohols nucleophiles. For more details, see the reactions of alcohols section below.

As one moves from primary to secondary to tertiary alcohols with the same backbone, the hydrogen bond strength, the boiling point, and the acidity typically decrease.

Applications

Total recorded alcohol per capita consumption (15+), in litres of pure alcohol^[6]

Alcohols can be used as a beverage (ethanol only), as fuel and for many scientific, medical, and industrial utilities. Ethanol in the form of alcoholic beverages has been consumed by humans since pre-historic times. A 50% v/v solution of ethylene glycol in water is commonly used as an antifreeze.

Some alcohols, mainly ethanol and methanol, can be used as an alcohol fuel. Fuel performance can be increased in forced induction internal combustion engines by injecting alcohol into the air intake after the turbocharger or supercharger has pressurized the air. This cools the pressurized air, providing a denser air charge, which allows for more fuel, and therefore more power.

Alcohols have applications in industry and science as reagents or solvents. Because of its low toxicity and ability to dissolve non-polar substances, ethanol can be used as a solvent in medical drugs, perfumes, and vegetable essences such as vanilla. In organic synthesis, alcohols serve as versatile intermediates.

Ethanol can be used as an antiseptic to disinfect the skin before injections are given, often along with iodine. Ethanol-based soaps are becoming common in restaurants and are convenient because they do not require drying due to the volatility of the compound. Alcohol is also used as a preservative for specimens.

Alcohol gels have become common as hand sanitizers.

Production

In industry, alcohols are produced in several ways:

• By fermentation using glucose produced from sugar from the hydrolysis of starch, in the presence of yeast and temperature of less than 37 °C to produce ethanol, for instance, the conversion of invertase to glucose and fructose or the conversion of glucose to zymase and ethanol.
• By direct hydration using ethylene (ethylene hydration)^[7] or other alkenes from cracking of fractions of distilled crude oil.

Endogenous

Several of the benign bacteria in the intestine use fermentation as a form of anaerobic respiration. This metabolic reaction produces ethanol as a waste product, just like aerobic respiration produces carbon dioxide and water. Thus, human bodies contain some quantity of alcohol endogenously produced by these bacteria.

Laboratory synthesis

Several methods exist for the preparation of alcohols in the laboratory.

Substitution

Primary alkyl halides react with aqueous NaOH or KOH mainly to primary alcohols in nucleophilic aliphatic substitution. (Secondary and especially tertiary alkyl halides will give the elimination (alkene) product instead). Grignard reagents react with carbonyl groups to secondary and tertiary alcohols. Related reactions are the Barbier reaction and the Nozaki-Hiyama reaction.

Reduction

Aldehydes or ketones are reduced with sodium borohydride or lithium aluminium hydride (after an acidic workup). Another reduction by aluminiumisopropylates is the Meerwein-Ponndorf-Verley reduction. Noyori asymmetric hydrogenation is the asymmetric reduction of β-keto-esters.

Hydrolysis

Alkenes engage in an acid catalysed hydration reaction using concentrated sulfuric acid as a catalyst that gives usually secondary or tertiary alcohols. The hydroboration-oxidation and oxymercuration-reduction of alkenes are more reliable in organic synthesis. Alkenes react with NBS and water in halohydrin formation reaction. Amines can be converted to diazonium salts, which are then hydrolyzed.

The formation of a secondary alcohol via reduction and hydration is shown:

Reactions

Deprotonation

Alcohols can behave as weak acids, undergoing deprotonation. The deprotonation reaction to produce an alkoxide salt is performed either with a strong base such as sodium hydride or n-butyllithium or with sodium or potassium metal.

2 R-OH + 2 NaH → 2 R-O^-Na⁺ + 2H₂↑

2 R-OH + 2 Na → 2 R-O⁻Na⁺ + H₂

2 CH₃CH₂-OH + 2 Na → 2 CH₃-CH₂-O⁻⁺ + H₂↑

Water is similar in pK_a to many alcohols, so with sodium hydroxide there is an equilibrium set-up, which usually lies to the left:

R-OH + NaOH ⇌ R-O^-Na⁺ + H₂O (equilibrium to the left)

It should be noted, however, that the bases used to deprotonate alcohols are strong themselves. The bases used and the alkoxides created are both highly moisture-sensitive chemical reagents.

The acidity of alcohols is also affected by the overall stability of the alkoxide ion. Electron-withdrawing groups attached to the carbon containing the hydroxyl group will serve to stabilize the alkoxide when formed, thus resulting in greater acidity. On the other hand, the presence of electron-donating group will result in a less stable alkoxide ion formed. This will result in a scenario whereby the unstable alkoxide ion formed will tend to accept a proton to reform the original alcohol.

With alkyl halides alkoxides give rise to ethers in the Williamson ether synthesis.

Nucleophilic substitution

The OH group is not a good leaving group in nucleophilic substitution reactions, so neutral alcohols do not react in such reactions. However, if the oxygen is first protonated to give R−OH₂⁺, the leaving group (water) is much more stable, and the nucleophilic substitution can take place. For instance, tertiary alcohols react with hydrochloric acid to produce tertiary alkyl halides, where the hydroxyl group is replaced by a chlorine atom by unimolecular nucleophilic substitution. If primary or secondary alcohols are to be reacted with hydrochloric acid, an activator such as zinc chloride is needed. In alternative fashion, the conversion may be performed directly using thionyl chloride.^[1]

Alcohols may, likewise, be converted to alkyl bromides using hydrobromic acid or phosphorus tribromide, for example:

3 R-OH + PBr₃ → 3 RBr + H₃PO₃

In the Barton-McCombie deoxygenation an alcohol is deoxygenated to an alkane with tributyltin hydride or a trimethylborane-water complex in a radical substitution reaction.

Dehydration

Alcohols are themselves nucleophilic, so R−OH₂⁺ can react with ROH to produce ethers and water in a dehydration reaction, although this reaction is rarely used except in the manufacture of diethyl ether.

More useful is the E1 elimination reaction of alcohols to produce alkenes. The reaction, in general, obeys Zaitsev's Rule, which states that the most stable (usually the most substituted) alkene is formed. Tertiary alcohols eliminate easily at just above room temperature, but primary alcohols require a higher temperature.

This is a diagram of acid catalysed dehydration of ethanol to produce ethene:

A more controlled elimination reaction is the Chugaev elimination with carbon disulfide and iodomethane.

Esterification

To form an ester from an alcohol and a carboxylic acid the reaction, known as Fischer esterification, is usually performed at reflux with a catalyst of concentrated sulfuric acid:

R-OH + R'-COOH → R'-COOR + H₂O

In order to drive the equilibrium to the right and produce a good yield of ester, water is usually removed, either by an excess of H₂SO₄ or by using a Dean-Stark apparatus. Esters may also be prepared by reaction of the alcohol with an acid chloride in the presence of a base such as pyridine.

Other types of ester are prepared in a similar manner — for example, tosyl (tosylate) esters are made by reaction of the alcohol with p-toluenesulfonyl chloride in pyridine.

Oxidation

Main article: Alcohol oxidation

Primary alcohols (R-CH₂-OH) can be oxidized either to aldehydes (R-CHO) or to carboxylic acids (R-CO₂H), while the oxidation of secondary alcohols (R¹R²CH-OH) normally terminates at the ketone (R¹R²C=O) stage. Tertiary alcohols (R¹R²R³C-OH) are resistant to oxidation.

The direct oxidation of primary alcohols to carboxylic acids normally proceeds via the corresponding aldehyde, which is transformed via an aldehyde hydrate (R-CH(OH)₂) by reaction with water before it can be further oxidized to the carboxylic acid.

Mechanism of oxidation of primary alcohols to carboxylic acids via aldehydes and aldehyde hydrates

Reagents useful for the transformation of primary alcohols to aldehydes are normally also suitable for the oxidation of secondary alcohols to ketones. These include Collins reagent and Dess-Martin periodinane. The direct oxidation of primary alcohols to carboxylic acids can be carried out using Potassium permanganate or the Jones reagent.

Toxicity

Main articles: Short-term effects of alcohol and Long-term effects of alcohol

Most significant of the possible long-term effects of ethanol. In addition, in pregnant women, it causes fetal alcohol syndrome.

Ethanol in alcoholic beverages has been consumed by humans since prehistoric times for a variety of hygienic, dietary, medicinal, religious, and recreational reasons. The consumption of large doses of ethanol causes drunkenness (intoxication), which may lead to a hangover as its effects wear off. Depending upon the dose and the regularity of its consumption, ethanol can cause acute respiratory failure or death. Because ethanol impairs judgment in humans, it can be a catalyst for reckless or irresponsible behavior. The LD₅₀ of ethanol in rats is 10.3 g/kg.^[8]

Other alcohols are substantially more poisonous than ethanol, partly because they take much longer to be metabolized and partly because their metabolism produces substances that are even more toxic. Methanol (wood alcohol), for instance, is oxidized to formaldehyde and then to the poisonous formic acid in the liver by alcohol dehydrogenase and formaldehyde dehydrogenase enzymes, respectively; accumulation of formic acid can lead to blindness or death.^[9] Likewise, poisoning due to other alcohols such as ethylene glycol or diethylene glycol are due to their metabolites, which are also produced by alcohol dehydrogenase.^[10][11] An effective treatment to prevent toxicity after methanol or ethylene glycol ingestion is to administer ethanol. Alcohol dehydrogenase has a higher affinity for ethanol, thus preventing methanol from binding and acting as a substrate. Any remaining methanol will then have time to be excreted through the kidneys.^[9][12][13]

Methanol itself, while poisonous, has a much weaker sedative effect than ethanol. Some longer-chain alcohols such as n-propanol, isopropanol, n-butanol, t-butanol, and 2-methyl-2-butanol do, however, have stronger sedative effects, but also have higher toxicity than ethanol.^[14][15] These longer chain alcohols are found as contaminants in some alcoholic beverages and are known as fusel alcohols,^[16][17] and are reputed to cause severe hangovers although it is unclear if the fusel alcohols are actually responsible.^[18] Many longer chain alcohols are used in industry as solvents and are occasionally abused by alcoholics,^[19][20] leading to a range of adverse health effects.^[21]

Occurrence in nature

Alcohol has been found outside the Solar System. It can be found in low densities in star and planetary system forming regions of space.^[22]

See also

• Blood alcohol content
• Breathalyzer
• Cooking with alcohol
• Enol
• Fatty alcohol
• History of alcoholic beverages
• List of countries by alcohol consumption
• Phenols
• Polyol
• Rubbing alcohol
• Sugar alcohol
• Surrogate alcohol
• Transesterification

References

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3. ^ ^{a b} William Reusch. "Alcohols". VirtualText of Organic Chemistry. http://www.cem.msu.edu/~reusch/VirtualText/alcohol1.htm#alcnom. Retrieved 2007-09-14. 
4. ^ Organic chemistry IUPAC nomenclature. Alcohols Rule C-201. http://www.acdlabs.com/iupac/nomenclature/79/r79_202.htm
5. ^ Majerza Irena, Natkaniec Ireneusz (2006). "Experimental and theoretical IR, R, and INS spectra of 2,2,4,4-tetramethyl-3-t-butyl-pentane-3-ol". Journal of Molecular Structure 788 (1–3): 93–101. doi:10.1016/j.molstruc.2005.11.022. 
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8. ^ Robert S. Gable (2004). "Comparison of acute lethal toxicity of commonly abused psychoactive substances" (reprint). Addiction 99 (6): 686–696. doi:10.1111/j.1360-0443.2004.00744.x. PMID 15139867. http://web.cgu.edu/faculty/gabler/toxicity%20Addiction%20offprint.pdf. 
9. ^ ^{a b} Schep LJ, Slaughter RJ, Vale JA, Beasley DM (Sep 30 2009). "A seaman with blindness and confusion". BMJ 339: b3929. doi:10.1136/bmj.b3929. PMID 19793790. http://www.bmj.com/cgi/content/full/339/sep30_1/b3929. 
10. ^ Brent J (May 2009). "Fomepizole for ethylene glycol and methanol poisoning". N. Engl. J. Med. 360 (21): 2216–23. doi:10.1056/NEJMct0806112. ISSN 0028-4793. PMID 19458366. 
11. ^ Schep LJ, Slaughter RJ, Temple WA, Beasley DM (July 2009). "Diethylene glycol poisoning". Clin Toxicol (Phila) 47 (6): 525–35. doi:10.1080/15563650903086444. ISSN 1556-3650. PMID 19586352. 
12. ^ Zimmerman HE, Burkhart KK, Donovan JW (1999). "Ethylene glycol and methanol poisoning: diagnosis and treatment". Journal of emergency nursing: JEN : official publication of the Emergency Department Nurses Association 25 (2): 116–20. PMID 10097201. 
13. ^ Lobert S (2000). "Ethanol, isopropanol, methanol, and ethylene glycol poisoning". Critical care nurse 20 (6): 41–7. PMID 11878258. 
14. ^ McKee M, Suzcs S, Sárváry A, Adany R, Kiryanov N, Saburova L, Tomkins S, Andreev E et al. (2005). "The composition of surrogate alcohols consumed in Russia". Alcoholism, clinical and experimental research 29 (10): 1884–8. doi:10.1097/01.alc.0000183012.93303.90. PMID 16269919. 
15. ^ Bunc M, Pezdir T, Mozina H, Mozina M, Brvar M (2006). "Butanol ingestion in an airport hangar". Human & experimental toxicology 25 (4): 195–7. doi:10.1191/0960327106ht607oa. PMID 16696295. 
16. ^ Woo KL (2005). "Determination of low molecular weight alcohols including fusel oil in various samples by diethyl ether extraction and capillary gas chromatography". Journal of AOAC International 88 (5): 1419–27. doi:10.5555/jaoi.2005.88.5.1419. PMID 16385992. 
17. ^ Lachenmeier DW, Haupt S, Schulz K (2008). "Defining maximum levels of higher alcohols in alcoholic beverages and surrogate alcohol products". Regulatory toxicology and pharmacology : RTP 50 (3): 313–21. doi:10.1016/j.yrtph.2007.12.008. PMID 18295386. 
18. ^ Hori H, Fujii W, Hatanaka Y, Suwa Y (2003). "Effects of fusel oil on animal hangover models". Alcoholism, clinical and experimental research 27 (8 Suppl): 37S–41S. doi:10.1097/01.ALC.0000078828.49740.48. PMID 12960505. 
19. ^ Wiernikowski A, Piekoszewski W, Krzyzanowska-Kierepka E, Gomułka E (1997). "Acute oral poisoning with isopropyl alcohol in alcoholics". Przeglad lekarski 54 (6): 459–63. PMID 9333902. 
20. ^ Mańkowski W, Klimaszyk D, Krupiński B (2000). "How to differentiate acute isopropanol poisoning from ethanol intoxication? -- a case report". Przeglad lekarski 57 (10): 588–90. PMID 11199895. 
21. ^ Bogomolova IN, Bukeshov MK, Bogomolov DV (2004). "The forensic medical diagnosis of intoxication of alcohol surrogates by morphological findings". Sudebno-meditsinskaia ekspertiza 47 (5): 22–5. PMID 15523882. 
22. ^ Charnley, S. B.; Kress, M. E., Tielens, A. G. G. M., & Millar, T. J.. "Interstellar Alcohols". Astrophysical Journal 448: 232. Bibcode 1995ApJ...448..232C. doi:10.1086/175955. 

Bibliography

Media related to Alcohol at Wikimedia Commons Quotations related to Alcohol at Wikiquote

• Metcalf, Allan A. (1999). The World in So Many Words. Houghton Mifflin. ISBN 0395959209.