Alcohol

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Ball-and-stick model of an alcohol molecule (R3COH). The red and grey balls represent the hydroxyl group (-OH). The three "R's" stand for carbon substituents or hydrogen atoms. Alcohol.png
Ball-and-stick model of an alcohol molecule (R3COH). The red and grey balls represent the hydroxyl group (-OH). The three "R's" stand for carbon substituents or hydrogen atoms.
The bond angle between an hydroxyl group (-OH) and a chain of carbon atoms (R) Alcohol general.svg
The bond angle between an hydroxyl group (-OH) and a chain of carbon atoms (R)

In chemistry, an alcohol is any organic compound in which the hydroxyl functional group (–O H) is bound to a carbon. [2] The term alcohol originally referred to the primary alcohol ethanol (ethyl alcohol), which is used as a drug and is the main alcohol present in alcoholic beverages. An important class of alcohols, of which methanol and ethanol are the simplest members, includes all compounds for which the general formula is CnH2n+1OH. It is these simple monoalcohols that are the subject of this article.

Chemistry is the scientific discipline involved with elements and compounds composed of atoms, molecules and ions: their composition, structure, properties, behavior and the changes they undergo during a reaction with other substances.

Organic compound Chemical compound that contains carbon (except for a several compounds traditionally classified as inorganic compounds)

In chemistry, an organic compound is generally any chemical compound that contains carbon. Due to carbon's ability to catenate, millions of organic compounds are known. Study of the properties and synthesis of organic compounds is the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds, along with a handful of other exceptions, are not classified as organic compounds and are considered inorganic. No consensus exists among chemists on precisely which carbon-containing compounds are excluded, making the definition of an organic compound elusive. Although organic compounds make up only a small percentage of the Earth's crust, they are of central importance because all known life is based on organic compounds. Most synthetically produced organic compounds are ultimately derived from petrochemicals consisting mainly of hydrocarbons.

Functional group moiety that imparts a molecules characteristic chemical reactions; moiety that participates in similar chemical reactions in most molecules that contain it

In organic chemistry, functional groups are specific substituents or moieties within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction(s) regardless of the size of the molecule it is a part of. This allows for systematic prediction of chemical reactions and behavior of chemical compounds and design of chemical syntheses. Furthermore, the reactivity of a functional group can be modified by other functional groups nearby. In organic synthesis, functional group interconversion is one of the basic types of transformations.

Contents

The suffix -ol appears in the IUPAC chemical name of all substances where the hydroxyl group is the functional group with the highest priority. When a higher priority group is present in the compound, the prefix hydroxy- is used in its IUPAC name. The suffix -ol in non-IUPAC names (such as paracetamol or cholesterol) also typically indicates that the substance is an alcohol. However, many substances that contain hydroxyl functional groups (particularly sugars, such as glucose and sucrose) have names which include neither the suffix -ol, nor the prefix hydroxy-.

In chemical nomenclature, the IUPAC nomenclature of organic chemistry is a systematic method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). It is published in the Nomenclature of Organic Chemistry. Ideally, every possible organic compound should have a name from which an unambiguous structural formula can be created. There is also an IUPAC nomenclature of inorganic chemistry.

Paracetamol common drug for pain and fever

Paracetamol, also known as acetaminophen and APAP, is a medication used to treat pain and fever. It is typically used for mild to moderate pain relief. There is mixed evidence for its use to relieve fever in children. It is often sold in combination with other medications, such as in many cold medications. Paracetamol is also used for severe pain, such as cancer pain and pain after surgery, in combination with opioid pain medication. It is typically used either by mouth or rectally, but is also available by injection into a vein. Effects last between 2 to 4 hours.

Cholesterol sterol (or modified steroid),[4] a type of lipid molecule, and is biosynthesized by all animal cells, because it is an essential structural component of all animal cell membranes

Cholesterol is an organic molecule. It is a sterol, a type of lipid molecule, and is biosynthesized by all animal cells, because it is an essential structural component of all animal cell membranes.

History

Alcohol distillation likely originated in India. During 2000 BCE, people of India used an alcoholic drink called Sura . [3] Alcohol distillation was known to Islamic chemists as early as the eighth century. [4] [5]

India Country in South Asia

India, also known as the Republic of India, is a country in South Asia. It is the seventh largest country by area and with more than 1.3 billion people, it is the second most populous country and the most populous democracy in the world. Bounded by the Indian Ocean on the south, the Arabian Sea on the southwest, and the Bay of Bengal on the southeast, it shares land borders with Pakistan to the west; China, Nepal, and Bhutan to the northeast; and Bangladesh and Myanmar to the east. In the Indian Ocean, India is in the vicinity of Sri Lanka and the Maldives, while its Andaman and Nicobar Islands share a maritime border with Thailand and Indonesia.

The Arab chemist, al-Kindi, unambiguously described the distillation of wine in a treatise titled as "The Book of the chemistry of Perfume and Distillations". [6] [7] [8]

Al-Kindi Muslim Arab philosopher, mathematician, physician, and musician

Abu Yūsuf Yaʻqūb ibn ʼIsḥāq aṣ-Ṣabbāḥ al-Kindī was an Arab Muslim philosopher, polymath, mathematician, physician and musician. Al-Kindi was the first of the Muslim peripatetic philosophers, and is unanimously hailed as the "father of Arab philosophy" for his synthesis, adaptation and promotion of Greek and Hellenistic philosophy in the Muslim world.

The Persian physician, alchemist, polymath and philosopher Rhazes (854 CE – 925 CE) [9] is credited with the discovery of ethanol. [10] [11]

The Persians are an Iranian ethnic group that make up over half the population of Iran. They share a common cultural system and are native speakers of the Persian language, as well as closely related languages.

Medicine in the medieval Islamic world

In the history of medicine, Islamic medicine is the science of medicine developed in the Islamic Golden Age, and written in Arabic, the lingua franca of Islamic civilization.

Alchemy and chemistry in medieval Islam

Alchemy and chemistry in Islam refers to the study of both traditional alchemy and early practical chemistry by scholars in the medieval Islamic world. The word alchemy was derived from the Arabic word كيمياء or kīmiyāʾ. and may ultimately derive from the ancient Egyptian word kemi, meaning black.

Nomenclature

Etymology

The word "alcohol" is from the Arabic kohl (Arabic : الكحل, translit.  al-kuḥl), a powder used as an eyeliner. [12] Al- is the Arabic definite article, equivalent to the in English. Alcohol was originally used for the very fine powder produced by the sublimation of the natural mineral stibnite to form antimony trisulfide Sb
2
S
3
. It was considered to be the essence or "spirit" of this mineral. It was used as an antiseptic, eyeliner, and cosmetic. The meaning of alcohol was extended to distilled substances in general, and then narrowed to ethanol, when "spirits" was a synonym for hard liquor. [13]

Kohl (cosmetics) ancient eye cosmetic, traditionally made by grinding stibnite (Sb₂S₃) for similar purposes to charcoal used in mascara

Kohl (Arabic: كُحْل‎ kuḥl) is an ancient eye cosmetic, traditionally made by grinding stibnite (Sb2S3) for similar purposes to charcoal used in mascara. It is widely used in the Middle East, North Africa, the Mediterranean, South Asia, and the Horn of Africa as eyeliner to contour and/or darken the eyelids and as mascara for the eyelashes. It is worn mostly by women, but also by some men and children.

The romanization of Arabic writes written and spoken Arabic in the Latin script in one of various systematic ways. Romanized Arabic is used for a number of different purposes, among them transcription of names and titles, cataloging Arabic language works, language education when used in lieu of or alongside the Arabic script, and representation of the language in scientific publications by linguists. These formal systems, which often make use of diacritics and non-standard Latin characters and are used in academic settings or for the benefit of non-speakers, contrast with informal means of written communication used by speakers such as the Latin-based Arabic chat alphabet.

An article is a word that is used with a noun to specify grammatical definiteness of the noun, and in some languages extending to volume or numerical scope.

Bartholomew Traheron, in his 1543 translation of John of Vigo, introduces the word as a term used by "barbarous" (Moorish) authors for "fine powder." Vigo wrote: "the barbarous auctours use alcohol, or (as I fynde it sometymes wryten) alcofoll, for moost fine poudre." [14]

The 1657 Lexicon Chymicum, by William Johnson glosses the word as "antimonium sive stibium." [15] 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) refers to "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" (the chemical known today as ethanol) in the 18th century and was extended to the class of substances so-called as "alcohols" in modern chemistry after 1850. [14]

The term ethanol was invented 1892, combining the word ethane with the "-ol" ending of "alcohol". [16]

Systematic names

IUPAC nomenclature is used in scientific publications and where precise identification of the substance is important, especially in cases where the relative complexity of the molecule does not make such a systematic name unwieldy. In naming simple alcohols, the name of the alkane chain loses the terminal e and adds the suffix -ol, e.g., as in "ethanol" from the alkane chain name "ethane". [17] When necessary, the position of the hydroxyl group is indicated by a number between the alkane name and the -ol: propan-1-ol for CH
3
CH
2
CH
2
OH
, propan-2-ol for CH
3
CH(OH)CH
3
. If a higher priority group is present (such as an aldehyde, ketone, or carboxylic acid), then the prefix hydroxy-is used, [17] e.g., as in 1-hydroxy-2-propanone (CH
3
C(O)CH
2
OH
). [18]

Some examples of simple alcohols and how to name them
CH3–CH2–CH2–OH Propan-2-ol displayed.svg Cyclohexanol displayed.svg 2-methylpropan-1-ol displayed.svg 2-methylbutan-2-ol displayed.svg
Propan-1-ol.svg 2-Propanol.svg Cyclohexanol acsv.svg Isobutanol.svg 2-Methyl-2-butanol FormulaV1-Seite001.svg
n-propyl alcohol,
propan-1-ol, or
1-propanol
isopropyl alcohol,
propan-2-ol, or
2-propanol
cyclohexanolisobutyl alcohol,
2-methylpropan-1-ol, or
2-methyl-1-propanol
tert-amyl alcohol,
2-methylbutan-2-ol, or
2-methyl-2-butanol
A primary alcoholA secondary alcoholA secondary alcoholA primary alcoholA tertiary alcohol

In cases where the OH functional group is bonded to an sp2 carbon on an aromatic ring the molecule is known as a phenol, and is named using the IUPAC rules for naming phenols. [19]

Common names

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 end or middle carbon on the straight propane chain. As described under systematic naming, if another group on the molecule takes priority, the alcohol moiety is often indicated using the "hydroxy-" prefix. [20]

Alcohols are then classified into primary, secondary (sec-, s-), and tertiary (tert-, t-), based upon the number of carbon atoms connected to the carbon atom that bears the hydroxyl functional group. (The respective numeric shorthands 1°, 2°, and 3° are also sometimes used in informal settings. [21] ) The primary alcohols have general formulas RCH2OH. The simplest primary alcohol is methanol (CH3OH), for which R=H, and the next is ethanol, for which R=CH3, the methyl group. Secondary alcohols are those of the form RR'CHOH, the simplest of which is 2-propanol (R=R'=CH3). For the tertiary alcohols the general form is RR'R"COH. The simplest example is tert-butanol (2-methylpropan-2-ol), for which each of R, R', and R" is CH3. In these shorthands, R, R', and R" represent substituents, alkyl or other attached, generally organic groups.

TypeFormula IUPAC NameCommon name
Monohydric
alcohols
CH3OH Methanol Wood alcohol
C2H5OH Ethanol Alcohol
C3H7OH Propan-2-ol Isopropyl alcohol,
Rubbing alcohol
C4H9OH Butan-1-ol Butanol,
Butyl alcohol
C5H11OH Pentan-1-ol Pentanol,
Amyl alcohol
C16H33OHHexadecan-1-ol Cetyl alcohol
Polyhydric
alcohols
C2H4(OH)2Ethane-1,2-diol Ethylene glycol
C3H6(OH)2Propane-1,2-diol Propylene glycol
C3H5(OH)3Propane-1,2,3-triol Glycerol
C4H6(OH)4Butane-1,2,3,4-tetraol Erythritol,
Threitol
C5H7(OH)5Pentane-1,2,3,4,5-pentol Xylitol
C6H8(OH)6hexane-1,2,3,4,5,6-hexol Mannitol,
Sorbitol
C7H9(OH)7Heptane-1,2,3,4,5,6,7-heptol Volemitol
Unsaturated
aliphatic
alcohols
C3H5OHProp-2-ene-1-ol Allyl alcohol
C10H17OH3,7-Dimethylocta-2,6-dien-1-ol Geraniol
C3H3OHProp-2-yn-1-ol Propargyl alcohol
Alicyclic
alcohols
C6H6(OH)6Cyclohexane-1,2,3,4,5,6-hexol Inositol
C10H19OH5-Methyl-2-(propan-2-yl)cyclohexan-1-ol Menthol

Applications

Total recorded alcohol per capita consumption (15+), in litres of pure ethanol Alcohol by Country.png
Total recorded alcohol per capita consumption (15+), in litres of pure ethanol

Alcohols have a long history of myriad uses. For simple mono-alcohols, which is the focus on this article, the following are most important industrial alcohols: [23]

Methanol is the most common industrial alcohol, with about 12 million tons/y produced in 1980. The combined capacity of the other alcohols is about the same, distributed roughly equally. [23]

Toxicity

With respect to acute toxicity, simple alcohols have low acute toxicities. Doses of several milliliters are tolerated. For pentanols, hexanols, octanols and longer alcohols, LD50 range from 2–5 g/kg (rats, oral). Methanol and ethanol are less acutely toxic. All alcohols are mild skin irritants. [23]

The metabolism of methanol (and ethylene glycol) is affected by the presence of ethanol, which has a higher affinity for liver alcohol dehydrogenase. In this way methanol will be excreted intact in urine. [24] [25] [26]

Physical properties

In general, the hydroxyl group makes alcohols polar. Those groups can form hydrogen bonds to one another and to most other compounds. Owing to the presence of the polar OH alcohols are more water-soluble than simple hydrocarbons. Methanol, ethanol, and propanol are miscible in water. Butanol, with a four-carbon chain, is moderately soluble.

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, and 34.6 °C for diethyl ether.

Occurrence in nature

Simple alcohols are found widely in nature. Ethanol is most prominent because it is the product of fermentation, a major energy-producing pathway. The other simple alcohols are formed in only trace amounts. More complex alcohols are pervasive, as manifested in sugars, some amino acids, and fatty acids.

Production

Ziegler and oxo processes

In the Ziegler process, linear alcohols are produced from ethylene and triethylaluminium followed by oxidation and hydrolysis. [23] An idealized synthesis of 1-octanol is shown:

Al(C2H5)3 + 9 C2H4 → Al(C8H17)3
Al(C8H17)3 + 3 O + 3 H2O → 3 HOC8H17 + Al(OH)3

The process generates a range of alcohols that are separated by distillation.

Many higher alcohols are produced by hydroformylation of alkenes followed by hydrogenation. When applied to a terminal alkene, as is common, one typically obtains a linear alcohol: [23]

RCH=CH2 + H2 + CO → RCH2CH2CHO
RCH2CH2CHO + 3 H2 → RCH2CH2CH2OH

Such processes give fatty alcohols, which are useful for detergents.

Hydration reactions

Some low molecular weight alcohols of industrial importance are produced by the addition of water to alkenes. Ethanol, isopropanol, 2-butanol, and tert-butanol are produced by this general method. Two implementations are employed, the direct and indirect methods. The direct method avoids the formation of stable intermediates, typically using acid catalysts. In the indirect method, the alkene is converted to the sulfate ester, which is subsequently hydrolyzed. The direct hydration using ethylene (ethylene hydration) [27] or other alkenes from cracking of fractions of distilled crude oil.

Hydration is also used industrially to produce the diol ethylene glycol from ethylene oxide.

Biological routes

Ethanol is obtained 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, such a process might proceed by the conversion of sucrose by the enzyme invertase into glucose and fructose, then the conversion of glucose by the enzyme complex zymase into ethanol (and carbon dioxide).

Several species of the benign bacteria in the intestine use fermentation as a form of anaerobic metabolism. This metabolic reaction produces ethanol as a waste product. Thus, human bodies contain some quantity of alcohol endogenously produced by these bacteria. In rare cases, this can be sufficient to cause "auto-brewery syndrome" in which intoxicating quantities of alcohol are produced. [28] [29] [30]

Like ethanol, butanol can be produced by fermentation processes. Saccharomyces yeast are known to produce these higher alcohols at temperatures above 75 °F (24 °C). The bacterium Clostridium acetobutylicum can feed on cellulose to produce butanol on an industrial scale. [31]

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:

Secondary alcohol formation-diagram.svg

Reactions

Deprotonation

With a pKa of around 16–19, they are, in general, slightly weaker acids than water. With strong bases such as sodium hydride or sodium they form salts called alkoxides , with the general formula RO M +.

2 R-OH + 2 NaH → 2 R-ONa+ + 2 H2
2 R-OH + 2 Na → 2 R-ONa+ + H2

The acidity of alcohols is strongly affected by solvation. In the gas phase, alcohols are more acidic than is water. [32]

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]

Alcohol reaction examples.gif

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

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:

Methanol acid base.svg

Upon treatment with strong acids, alcohols undergo the E1 elimination reaction 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 ethylene:

DehydrationOfAlcoholWithH-.png

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

Esterification

Alcohol and carboxylic acids react in the so-called Fischer esterification. The reaction usually requires a catalyst, such as concentrated sulfuric acid:

R-OH + R'-CO2H → R'-CO2R + H2O

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

Primary alcohols (R-CH2OH) can be oxidized either to aldehydes (R-CHO) or to carboxylic acids (R-CO2H). 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 Alcohol to aldehyde to acid.png
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.

See also

Notes

  1. "alcohols". IUPAC Gold Book. Retrieved 16 December 2013.
  2. IUPAC , Compendium of Chemical Terminology , 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006) " Alcohols ". doi : 10.1351/goldbook.A00204
  3. Dhawendra Kumar. Genomics and Health in the Developing World. Oxford University Press. p. 1128.
  4. Al-Hassani, Salim; Abattouy, Mohammed. "The Advent of Scientific Chemistry". Muslim Heritage. Retrieved 17 May 2018.
  5. Curzon, George Nathaniel (7 July 2010). "The History of Alcohol in Islam". Coming Anarchy . Retrieved 17 May 2018.
  6. Forbes, R. J. (1970). A Short History of the Art of Distillation. Brill Publishers. p. 87. ISBN   9004006176.
  7. Multhauf, Robert (1966). The Origins of Chemistry. London. pp. 204–6.
  8. Hill, Donald Routledge (1993). Islamic science and engineering. Edinburgh University Press. ISBN   9780748604555.
  9. Hitti, Philip K. (1977). History of the Arabs from the earliest times to the present (10th ed.). London: Macmillan Publishers. p. 365. ISBN   978-0-333-09871-4. The most notable medical authors who followed the epoch of the great translators were Persian in nationality but Arab in language: 'Ali al-Tabari, al-Razi, 'Ali ibn-al-'Abbas al-Majusi and ibn-Sina.
  10. Modanlou, Houchang D. (November 2008). "A tribute to Zakariya Razi (865 - 925 AD), an Iranian pioneer scholar" (PDF). Archives of Iranian Medicine. 11 (6): 673–677. PMID   18976043 . Retrieved 17 May 2018. Abu Bakr Mohammad Ibn Zakariya al-Razi, known in the West as Rhazes, was born in 865 AD in the ancient city of Rey, Near Tehran. A musician during his youth he became an alchemist. He discovered alcohol and sulfuric acid. He classified substances as plants, organic, and inorganic.
  11. Schlosser, Stefan (May 2011). "Distillation – from Bronze Age till today" . Retrieved 17 May 2018. Al-Razi (865–925) was the preeminent Pharmacist and physician of his time [5]. The discovery of alcohol, first to produce acids such as sulfuric acid, writing up extensive notes on diseases such as smallpox and chickenpox, a pioneer in ophthalmology, author of first book on pediatrics, making leading contributions in inorganic and organic chemistry, also the author of several philosophical works.
  12. Harper, Douglas. "Alcohol". Etymonline . MaoningTech. Retrieved 17 May 2018.
  13. Lohninger, H. (21 December 2004). "Etymology of the Word "Alcohol"". VIAS Encyclopedia. Retrieved 17 May 2018.
  14. 1 2 "alcohol, n.". OED Online . Oxford University Press. 15 November 2016.
  15. Johnson, William (1652). Lexicon Chymicum.
  16. Armstrong, Henry E. (8 July 1892). "Contributions to an international system of nomenclature. The nomenclature of cycloids". Proc. Chem. Soc. 8 (114): 128. doi:10.1039/PL8920800127. As ol is indicative of an OH derivative, there seems no reason why the simple word acid should not connote carboxyl, and why al should not connote COH; the names ethanol ethanal and ethanoic acid or simply ethane acid would then stand for the OH, COH and COOH derivatives of ethane.
  17. 1 2 William Reusch. "Alcohols". VirtualText of Organic Chemistry. Archived from the original on 19 September 2007. Retrieved 14 September 2007.
  18. Organic chemistry IUPAC nomenclature. Alcohols Rule C-201.
  19. Organic Chemistry Nomenclature Rule C-203: Phenols
  20. "How to name organic compounds using the IUPAC rules". www.chem.uiuc.edu. THE DEPARTMENT OF CHEMISTRY AT THE UNIVERSITY OF ILLINOIS. Retrieved 14 November 2016.
  21. Reusch, William. "Nomenclature of Alcohols". chemwiki.ucdavis.edu/. Retrieved 17 March 2015.
  22. "Global Status Report on Alcohol 2004" (PDF). Retrieved 28 November 2010.
  23. 1 2 3 4 5 Falbe, Jürgen; Bahrmann, Helmut; Lipps, Wolfgang; Mayer, Dieter, "Alcohols, Aliphatic", Ullmann's Encyclopedia of Industrial Chemistry , Weinheim: Wiley-VCH, doi:10.1002/14356007.a01_279 .
  24. Schep LJ, Slaughter RJ, Vale JA, Beasley DM (30 September 2009). "A seaman with blindness and confusion". BMJ . 339: b3929. doi:10.1136/bmj.b3929. PMID   19793790.
  25. Zimmerman HE, Burkhart KK, Donovan JW (1999). "Ethylene glycol and methanol poisoning: diagnosis and treatment". Journal of Emergency Nursing. 25 (2): 116–20. doi:10.1016/S0099-1767(99)70156-X. PMID   10097201.
  26. Lobert S (2000). "Ethanol, isopropanol, methanol, and ethylene glycol poisoning". Critical care nurse. 20 (6): 41–7. PMID   11878258.
  27. Lodgsdon J.E. (1994). "Ethanol". In Kroschwitz J.I. Encyclopedia of Chemical Technology. 9 (4th ed.). New York: John Wiley & Sons. p. 820. ISBN   0-471-52677-0.
  28. P. Geertinger MD; J. Bodenhoff; K. Helweg-Larsen; A. Lund (1 September 1982). "Endogenous alcohol production by intestinal fermentation in sudden infant death". Zeitschrift für Rechtsmedizin. Springer-Verlag. 89 (3): 167–172. doi:10.1007/BF01873798.
  29. Logan BK, Jones AW (July 2000). "Endogenous ethanol 'auto-brewery syndrome' as a drunk-driving defence challenge". Medicine, science, and the law. 40 (3): 206–15. doi:10.1177/002580240004000304. PMID   10976182.
  30. Cecil Adams (20 October 2006). "Designated drunk: Can you get intoxicated without actually drinking alcohol?". The Straight Dope. Retrieved 27 February 2013.
  31. Zverlov, W; Berezina, O; Velikodvorskaya, GA; Schwarz, WH (August 2006). "Bacterial acetone and butanol production by industrial fermentation in the Soviet Union: use of hydrolyzed agricultural waste for biorefinery". Applied Microbiology and Biotechnology. 71 (5): 587–97. doi:10.1007/s00253-006-0445-z. PMID   16685494.
  32. Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, ISBN   0-471-72091-7

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A carboxylic acid is an organic compound that contains a carboxyl group. The general formula of a carboxylic acid is R–COOH, with R referring to the rest of the molecule. Carboxylic acids occur widely. Important examples include the amino acids and acetic acid. Deprotonation of a carboxyl group gives a carboxylate anion. Important carboxylate salts are soaps.

Ether class of organic compounds

Ethers are a class of organic compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula R–O–R′, where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anesthetic diethyl ether, commonly referred to simply as "ether" (CH3–CH2–O–CH2–CH3). Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

Ester chemical compounds consisting of a carbonyl adjacent to an ether linkage

In chemistry, an ester is a chemical compound derived from an acid in which at least one –OH (hydroxyl) group is replaced by an –O–alkyl (alkoxy) group. Usually, esters are derived from a carboxylic acid and an alcohol. Glycerides, which are fatty acid esters of glycerol, are important esters in biology, being one of the main classes of lipids, and making up the bulk of animal fats and vegetable oils. Esters with low molecular weight are commonly used as fragrances and found in essential oils and pheromones. Phosphoesters form the backbone of DNA molecules. Nitrate esters, such as nitroglycerin, are known for their explosive properties, while polyesters are important plastics, with monomers linked by ester moieties. Esters usually have a sweet smell and are considered high-quality solvents for a broad array of plastics, plasticizers, resins, and lacquers. They are also one of the largest classes of synthetic lubricants on the commercial market.

Ethanol is a chemical compound, a simple alcohol with the chemical formula C
2
H
5
OH
. Its formula can be also written as CH
3
CH
2
OH or C
2
H
5
OH, and is often abbreviated as EtOH. Ethanol is a volatile, flammable, colorless liquid with a slight characteristic odor. It is a psychoactive substance and is the principal type of alcohol found in alcoholic drinks.

Methanol, also known as methyl alcohol among others, is a chemical with the formula CH3OH (a methyl group linked to a hydroxyl group, often abbreviated MeOH). Methanol acquired the name wood alcohol because it was once produced chiefly by the destructive distillation of wood. Today, methanol is mainly produced industrially by hydrogenation of carbon monoxide.

Aldehyde organic compound containing a functional group with the structure −CHO, consisting of a carbonyl center (a carbon double-bonded to oxygen) with the carbon atom also bonded to hydrogen and to an R group, which is any generic alkyl or side chain

An aldehyde is an organic compound containing a functional group with the structure −CHO, consisting of a carbonyl center with the carbon atom also bonded to hydrogen and to an R group, which is any generic alkyl or side chain. The group—without R—is the aldehyde group, also known as the formyl group. Aldehydes are common in organic chemistry, and many fragrances are aldehydes.

Butanol (also called butyl alcohol) is a four-carbon alcohol with a formula of C4H9OH, which occurs in five isomeric structures (four structural isomers), from a straight-chain primary alcohol to a branched-chain tertiary alcohol; all are a butyl or isobutyl group linked to a hydroxyl group (sometimes represented as BuOH, n-BuOH, and i-BuOH). These are n-butanol, 2 stereoisomers of sec-butanol, isobutanol and tert-butanol. Butanol is primarily used as a solvent, as an intermediate in chemical synthesis, and as a fuel. It is sometimes also called biobutanol when produced biologically and petrobutanol when produced from petroleum, those two names refer to very same substance, but highlight the different origin.

Haloalkane

The haloalkanes are a group of chemical compounds derived from alkanes containing one or more halogens. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially and, consequently, are known under many chemical and commercial names. They are used as flame retardants, fire extinguishants, refrigerants, propellants, solvents, and pharmaceuticals. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious pollutants and toxins. For example, the chlorofluorocarbons have been shown to lead to ozone depletion. Methyl bromide is a controversial fumigant. Only haloalkanes which contain chlorine, bromine, and iodine are a threat to the ozone layer, but fluorinated volatile haloalkanes in theory may have activity as greenhouse gases. Methyl iodide, a naturally occurring substance, however, does not have ozone-depleting properties and the United States Environmental Protection Agency has designated the compound a non-ozone layer depleter. For more information, see Halomethane. Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen.

In chemistry, a hydration reaction is a chemical reaction in which a substance combines with water. In organic chemistry, water is added to an unsaturated substrate, which is usually an alkene or an alkyne. This type of reaction is employed industrially to produce ethanol, isopropanol, and 2-butanol.

A diol is a chemical compound containing two hydroxyl groups. An aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified.

Primary alcohol alcohols with the hydroxy-group attached to the first carbon atom

A primary alcohol is an alcohol which has the hydroxyl group connected to a primary carbon atom. It can also be defined as a molecule containing a “–CH2OH” group. In contrast, a secondary alcohol has a formula “–CHROH” and a tertiary alcohol has a formula “–CR2OH”, where “R” indicates a carbon-containing group.

Benzyl group The organic moiety C6H5CH2‒

In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure C6H5CH2–. Benzyl features a benzene ring attached to a CH2 group.

2-Butanol group of stereoisomers

2-Butanol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. This secondary alcohol is a flammable, colorless liquid that is soluble in 3 parts water and completely miscible with polar organic solvents such as ethers and other alcohols. It is produced on a large scale, primarily as a precursor to the industrial solvent methyl ethyl ketone. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-2-butanol and (S)-(+)-2-butanol. It is normally found as an equal mixture of the two stereoisomers — a racemic mixture.

<i>tert</i>-Butyl alcohol chemical compound

tert-Butyl alcohol (TBA), also called tert-butanol or t-butanol, is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). It is one of the four isomers of butanol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

1-Propanol is a primary alcohol with the formula CH3CH2CH2OH (sometimes represented as PrOH or n-PrOH). This colorless liquid is also known as propan-1-ol, 1-propyl alcohol, n-propyl alcohol, and n-propanol. It is an isomer of 2-propanol (propan-2-ol, isopropyl alcohol, isopropanol). It is formed naturally in small amounts during many fermentation processes and used as a solvent in the pharmaceutical industry mainly for resins and cellulose esters.

Bioconversion of biomass to mixed alcohol fuels

The bioconversion of biomass to mixed alcohol fuels can be accomplished using the MixAlco process. Through bioconversion of biomass to a mixed alcohol fuel, more energy from the biomass will end up as liquid fuels than in converting biomass to ethanol by yeast fermentation.

Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbonylation also refers to oxidation of protein side chains.

Acetic acid A colourless liquid organic compound found in vinegar

Acetic acid, systematically named ethanoic acid, is a colourless liquid organic compound with the chemical formula CH3COOH (also written as CH3CO2H or C2H4O2). When undiluted, it is sometimes called glacial acetic acid. Vinegar is no less than 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. Acetic acid has a distinctive sour taste and pungent smell. In addition to household vinegar, it is mainly produced as a precursor to polyvinyl acetate and cellulose acetate. It is classified as a weak acid since it only partially dissociates in solution, but concentrated acetic acid is corrosive and can attack the skin.

Isopropyl alcohol (IUPAC name propan-2-ol; commonly called isopropanol or 2-propanol) is a compound with the chemical formula CH3CHOHCH3. It is a colorless, flammable chemical compound with a strong odor. As an isopropyl group linked to a hydroxyl group, it is the simplest example of a secondary alcohol, where the alcohol carbon atom is attached to two other carbon atoms. It is a structural isomer of 1-propanol and ethyl methyl ether.

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