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Phenol (also called carbolic acid) is an
aromatic In chemistry Chemistry is the scientific Science () is a systematic enterprise that builds and organizes knowledge Knowledge is a familiarity or awareness, of someone or something, such as facts A fact is an occurrence in ...
organic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behavior and the changes they undergo during ...
with the molecular
formula In science Science () is a systematic enterprise that Scientific method, builds and organizes knowledge in the form of Testability, testable explanations and predictions about the universe."... modern science is a discovery as well a ...
C6H5OH. It is a white
crystal A crystal or crystalline solid is a solid Solid is one of the four fundamental states of matter (the others being liquid A liquid is a nearly incompressible fluid In physics, a fluid is a substance that continually Deformatio ...

crystal
line
solid Solid is one of the four fundamental states of matter 4 (four) is a number A number is a mathematical object A mathematical object is an abstract concept arising in mathematics. In the usual language of mathematics, an ''object'' is an ...

solid
that is
volatile Volatility or volatile may refer to: Chemistry * Volatility (chemistry), a measuring tendency of a substance or liquid to vaporize easily * Relative volatility, a measure of vapor pressures of the components in a liquid mixture * Volatiles, a gr ...
. The molecule consists of a
phenyl group In organic chemistry Organic chemistry is a branch of chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, prope ...

phenyl group
(−C6H5) bonded to a
hydroxy group A hydroxy or hydroxyl group is a functional group with the chemical formula -OH and composed of one oxygen Oxygen is the chemical element Image:Simple Periodic Table Chart-blocks.svg, 400px, Periodic table, The periodic table of the ...
(−OH). Mildly
acidic An acid is a molecule A molecule is an electrically Electricity is the set of physical phenomena associated with the presence and motion Image:Leaving Yongsan Station.jpg, 300px, Motion involves a change in position In phys ...
, it requires careful handling because it can cause
chemical burn A chemical burn occurs when living tissue is exposed to a corrosive substance (such as a strong acid An acid is a or capable of donating a (hydrogen ion H+) (a ), or, alternatively, capable of forming a with an (a ). The first categ ...
s. Phenol was first extracted from
coal tar Coal tar is a thick dark liquid which is a by-product of the production of coke and coal gas Coal gas is a flammable gaseous fuel Fuel gas is any one of a number of fuels that under ordinary conditions are gaseous. Many fuel gases are c ...
, but today is produced on a large scale (about 7 billion kg/year) from
petroleum Petroleum, also known as crude oil and oil, is a naturally occurring, yellowish-black liquid A liquid is a nearly incompressible In fluid mechanics or more generally continuum mechanics, incompressible flow (isochoric process, isoc ...

petroleum
-derived feedstocks. It is an important industrial
commodity In economics Economics () is a social science Social science is the branch A branch ( or , ) or tree branch (sometimes referred to in botany Botany, also called , plant biology or phytology, is the science of plan ...
as a
precursor Precursor or Precursors may refer to: *Precursor (religion) In religion, a precursor, also known as forerunner, predecessor, harbinger or herald, is a holy person who announced the approaching appearance of a central figure of the religion or who ...
to many materials and useful compounds. It is primarily used to synthesize
plastics Plastics are a wide range of syntheticA synthetic is an artificial material produced by organic chemistry, organic chemical synthesis. Synthetic may also refer to: In the sense of both "combination" and "artificial" * Synthetic chemical or s ...

plastics
and related materials. Phenol and its chemical
derivatives Derivative may refer to: In mathematics and economics *Brzozowski derivative in the theory of formal languages *Derivative in calculus, a quantity indicating how a function changes when the values of its inputs change. *Formal derivative, an opera ...
are essential for production of
polycarbonate Polycarbonates (PC) are a group of thermoplastic A thermoplastic, or thermosoft plastic, is a plastic polymer A polymer (; Greek ''wikt:poly-, poly-'', "many" + ''wikt:-mer, -mer'', "part") is a Chemical substance, substance or material c ...

polycarbonate
s,
epoxies The Epoxies were an American New wave music, new wave band from Portland, Oregon, formed in 2000. Heavily influenced by new wave, the band jokingly described themselves as robot garage rock. Members included FM Static on synthesizers, guitarist ...

epoxies
,
Bakelite Bakelite ( ; sometimes spelled Baekelite) or polyoxybenzylmethylenglycolanhydride was the first plastic Plastics are a wide range of syntheticA synthetic is an artificial material produced by organic chemistry, organic chemical synthesis. ...

Bakelite
,
nylon Nylon is a generic designation for a family of synthetic polymerSynthetic polymers are human-made polymers, often derived from petroleum oil. From the utility point of view they can be classified into three main categories: thermoplastics, ela ...

nylon
,
detergent A detergent is a surfactant Surfactants are compounds that lower the (or interfacial tension) between two liquids, between a gas and a liquid, or between a liquid and a solid. Surfactants may act as s, agents, , s, or s. The word "surfact ...
s,
herbicide Herbicides (, ), also commonly known as weedkillers, are substances used to control unwanted plant Plants are predominantly photosynthetic Photosynthesis is a process used by plants and other organisms to Energy transformation, conv ...
s such as
phenoxy herbicide Phenoxy herbicides (or "phenoxies") are two families of chemicals that have been developed as commercially important herbicide Herbicides (, ), also commonly known as weedkillers, are substances used to control unwanted plant Plants are ...
s, and numerous
pharmaceutical drug A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug Uncoated tablets, consisting of about 90% acetylsalicylic acid, along with a minor amount of inert fillers and binders. Aspir ...
s.


Properties

Phenol is a organic compound appreciably
soluble In chemistry Chemistry is the scientific Science () is a systematic enterprise that builds and organizes knowledge Knowledge is a familiarity or awareness, of someone or something, such as facts A fact is an occurrence i ...

soluble
in water, with about 84.2 g dissolving in 1000 mL (0.895 M). Homogeneous mixtures of phenol and water at phenol to water mass ratios of ~2.6 and higher are possible. The sodium salt of phenol,
sodium phenoxide Sodium phenoxide (sodium phenolate) is an organic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, struct ...
, is far more water-soluble.


Acidity

Phenol is a weak acid. In aqueous solution in the pH range ca. 8 - 12 it is in equilibrium with the phenolate
anion An ion () is an atom An atom is the smallest unit of ordinary matter In classical physics and general chemistry, matter is any substance that has mass and takes up space by having volume. All everyday objects that can be touched are ...
C6H5O (also called phenoxide): :C6H5OH C6H5O + H+ Phenol is more acidic than aliphatic alcohols. The differing pKa is attributed to
resonance stabilization In chemistry Chemistry is the scientific Science () is a systematic enterprise that builds and organizes knowledge Knowledge is a familiarity or awareness, of someone or something, such as facts A fact is an occurrence in ...
of the phenoxide
anion An ion () is an atom An atom is the smallest unit of ordinary matter In classical physics and general chemistry, matter is any substance that has mass and takes up space by having volume. All everyday objects that can be touched are ...
. In this way, the negative charge on oxygen is delocalized on to the ortho and para carbon atoms through the pi system. An alternative explanation involves the sigma framework, postulating that the dominant effect is the
induction Induction may refer to: Philosophy * Inductive reasoning, in logic, inferences from particular cases to the general case Biology and chemistry * Labor induction (birth/pregnancy) * Induction chemotherapy, in medicine * Induction period, the t ...
from the more electronegative sp2 hybridised carbons; the comparatively more powerful inductive withdrawal of electron density that is provided by the sp2 system compared to an sp3 system allows for great stabilization of the oxyanion. In support of the second explanation, the p''K''a of the
enol Enols, or more formally, alkenols, are a type of reactive structure or intermediate in organic chemistry Organic chemistry is a branch of chemistry Chemistry is the study of the properties and behavior of . It is a that covers the ...

enol
of
acetone Acetone, or propanone, is an organic compound , CH4; is among the simplest organic compounds. In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds composed of atoms, ...

acetone
in water is 10.9, making it only slightly less acidic than phenol (p''K''a 10.0). Thus, the greater number of resonance structures available to phenoxide compared to acetone enolate seems to contribute very little to its stabilization. However, the situation changes when solvation effects are excluded''.'' A recent ''in silico'' comparison of the gas phase acidities of the vinylogues of phenol and cyclohexanol in conformations that allow for or exclude resonance stabilization leads to the inference that about of the increased acidity of phenol is attributable to inductive effects, with resonance accounting for the remaining difference.


Hydrogen bonding

In
carbon tetrachloride Carbon tetrachloride, also known by many other names (such as tetrachloromethane, also recognised by the IUPAC, carbon tet in the cleaning industry Cleaning is the process of removing unwanted substances, such as dirt, infectious agents, and ...

carbon tetrachloride
and alkane solvents phenol
hydrogen bonds A hydrogen bond (or H-bond) is a primarily Electrostatics, electrostatic force of attraction between a hydrogen Hydrogen is the chemical element Image:Simple Periodic Table Chart-blocks.svg, 400px, Periodic table, The periodic table of ...
with a wide range of Lewis bases such as
pyridine Pyridine is a basic BASIC (Beginners' All-purpose Symbolic Instruction Code) is a family of general-purpose, high-level programming language In computer science Computer science deals with the theoretical foundations of informati ...

pyridine
,
diethyl ether Diethyl ether, or simply ether, is an organic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, ...

diethyl ether
, and
diethyl sulfide Diethyl sulfide is an organosulfur compound with the chemical formula . It is a colorless, malodorous liquid. Although a common thioether, it has few applications. Preparation Diethyl sulfide is a by-product of the commercial production of ethan ...
. The enthalpies of adduct formation and the –OH IR frequency shifts accompanying adduct formation have been studied. Phenol is classified as a hard acid which is compatible with the ''C''/''E'' ratio of the ''ECW'' model with ''E''A = 2.27 and ''C''A = 1.07. The relative acceptor strength of phenol toward a series of bases, versus other Lewis acids, can be illustrated by C-B plots.


Phenoxide anion

The phenoxide anion is a strong
nucleophile In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behavior and the changes they undergo during a ...

nucleophile
with a
nucleophilicity In chemistry Chemistry is the scientific Science () is a systematic enterprise that builds and organizes knowledge Knowledge is a familiarity or awareness, of someone or something, such as facts A fact is an occurrence in the ...
comparable to the one of carbanions or tertiary amines. It can react at both its oxygen or carbon sites as an ambident nucleophile (see
HSAB theory HSAB concept is an initialism An acronym is a word In linguistics Linguistics is the scientific study of language A language is a structured system of communication used by humans, including speech (spoken language), gestur ...
). Generally, oxygen attack of phenoxide anions is kinetically favored, while carbon-attack is thermodynamically preferred (see
Thermodynamic versus kinetic reaction control Thermodynamic reaction control or kinetic reaction control in a chemical reaction can decide the composition in a reaction product mixture when competing pathways lead to different products and the reaction conditions influence the conversion (che ...
). Mixed oxygen/carbon attack and by this a loss of selectivity is usually observed if the reaction rate reaches diffusion control.


Tautomerism

Phenol exhibits
keto-enol tautomerism Enols, or more formally, alkenols, are a type of reactive structure or chemical intermediate, intermediate in organic chemistry that is represented as an alkene (olefin) with a hydroxyl group attached to one end of the alkene double bond. The ter ...

keto-enol tautomerism
with its unstable keto tautomer cyclohexadienone, but only a tiny fraction of phenol exists as the keto form. The equilibrium constant for enolisation is approximately 10−13, which means only one in every ten trillion molecules is in the keto form at any moment. The small amount of stabilisation gained by exchanging a C=C bond for a C=O bond is more than offset by the large destabilisation resulting from the loss of aromaticity. Phenol therefore exists essentially entirely in the enol form. 4, 4' Substituted cyclohexadienone can undergo a dienone–phenol rearrangement in acid conditions and form stable 3,4‐disubstituted phenol. Phenoxides are
enolate Enolates are organic anions derived from the deprotonation of carbonyl compounds. Rarely isolated, they are widely used as reagents in the synthesis of organic compounds. Bonding and structure Enolate anions are electronically related to allyl ...

enolate
s stabilised by
aromaticity In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behavior and the changes they undergo during ...
. Under normal circumstances, phenoxide is more reactive at the oxygen position, but the oxygen position is a "hard" nucleophile whereas the alpha-carbon positions tend to be "soft".


Reactions

Phenol is highly reactive toward
electrophilic aromatic substitution Electrophilic aromatic substitution is an organic reaction Organic reactions are chemical reaction A chemical reaction is a process that leads to the chemical transformation of one set of chemical substance A chemical substance is a form of ...

electrophilic aromatic substitution
. The enhance nucleophilicity is attributed to donation
pi electron In chemistry Chemistry is the scientific Science () is a systematic enterprise that builds and organizes knowledge Knowledge is a familiarity or awareness, of someone or something, such as facts A fact is an occurrence in ...
density from O into the ring. Many groups can be atttached to the ring, via
halogenation In chemistry Chemistry is the scientific Science () is a systematic enterprise that builds and organizes knowledge Knowledge is a familiarity or awareness, of someone or something, such as facts A fact is an occurrence in ...

halogenation
,
acylationIn chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds composed of atoms, molecules and ions: their composition, structure, properties, behavior and the changes they undergo ...

acylation
,
sulfonation Aromatic sulfonation is an organic reaction Organic reactions are chemical reaction A chemical reaction is a process that leads to the chemical transformation of one set of chemical substance A chemical substance is a form of matter In ...
, and related processes. Phenol's ring is so strongly activated that bromination and chlorination lead readily to polysubstitution. Phenol reacts with dilute nitric acid at room temperature to give a mixture of 2-nitrophenol and 4-nitrophenol while with concentrated nitric acid, additional nitro groups are introduced, e.g. to give
2,4,6-trinitrophenol Picric acid is an organic compound with the formula (O2N)3C6H2OH. Its IUPAC name is 2,4,6-trinitrophenol (TNP). The name "picric" comes from the Greek language, Greek word πικρός (''pikros''), meaning "bitter", due to its bitter taste. It ...

2,4,6-trinitrophenol
. Aqueous solutions of phenol are weakly acidic and turn blue litmus slightly to red. Phenol is neutralized by
sodium hydroxide Sodium hydroxide, also known as lye A lye is a metal hydroxide traditionally obtained by leaching wood ashes, or a strong alkali In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chem ...

sodium hydroxide
forming sodium phenate or phenolate, but being weaker than
carbonic acid In chemistry, carbonic acid is a dibasic acid with the chemical formula A chemical formula is a way of presenting information about the chemical proportions of s that constitute a particular or molecule, using symbols, numbers, and s ...

carbonic acid
, it cannot be neutralized by
sodium bicarbonate Sodium bicarbonate ( IUPAC name: sodium hydrogen carbonate), commonly known as baking soda or bicarbonate of soda, is a chemical compound with the formula NaHCO3. It is a salt composed of a sodium cation (Na+) and a bicarbonate anion ( HCO3 ...

sodium bicarbonate
or
sodium carbonate Sodium carbonate, ·10, (also known as Natrium Carbonate, washing soda, soda ash and soda crystals) is the inorganic compound with the formula Na2CO3 and its various hydrates. All forms are white, odourless, water-soluble salts that yield modera ...

sodium carbonate
to liberate
carbon dioxide Carbon dioxide (chemical formula A chemical formula is a way of presenting information about the chemical proportions of s that constitute a particular or molecule, using symbols, numbers, and sometimes also other symbols, such as pare ...

carbon dioxide
. :C6H5OH + NaOH → C6H5ONa + H2O When a mixture of phenol and
benzoyl chloride Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound , CH4; is among the simplest organic compounds. ...

benzoyl chloride
are shaken in presence of dilute
sodium hydroxide Sodium hydroxide, also known as lye A lye is a metal hydroxide traditionally obtained by leaching wood ashes, or a strong alkali In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chem ...

sodium hydroxide
solution,
phenyl benzoate
phenyl benzoate
is formed. This is an example of the Schotten–Baumann reaction: :C6H5COCl + HOC6H5 → C6H5CO2C6H5 + HCl Phenol is reduced to
benzene Benzene is an organic Organic may refer to: * Organic, of or relating to an organism, a living entity * Organic, of or relating to an anatomical organ (anatomy), organ Chemistry * Organic matter, matter that has come from a once-living organ ...

benzene
when it is distilled with
zinc Zinc is a chemical element In chemistry, an element is a pure Chemical substance, substance consisting only of atoms that all have the same numbers of protons in their atomic nucleus, nuclei. Unlike chemical compounds, chemical element ...

zinc
dust or when its vapour is passed over granules of zinc at 400 °C: :C6H5OH + Zn → C6H6 + ZnO When phenol is treated with
diazomethane Diazomethane is the chemical compound CH2N2, discovered by German chemist Hans von PechmannHans von Pechmann (1 April 1850 – 19 April 1902) was a German chemist, renowned for his discovery of diazomethane in 1894. Pechmann condensation and Pech ...

diazomethane
in the presence of
boron trifluoride Boron trifluoride is the inorganic compound with the chemical formula, formula BF3. This pungent colourless toxic gas forms white fumes in moist air. It is a useful Lewis acid and a versatile building block for other boron compounds. Structure ...
(BF3),
anisole Anisole, or methoxybenzene, is an organic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, p ...

anisole
is obtained as the main product and nitrogen gas as a byproduct. :C6H5OH + CH2N2 → C6H5OCH3 + N2 When phenol reacts with iron(III) chloride solution, an intense violet-purple solution is formed.


Production

Because of phenol's commercial importance, many methods have been developed for its production, but the cumene process is the dominant technology.


Cumene process

Accounting for 95% of production (2003) is the
cumene process The cumene process (cumene–phenol process, Hock process) is an industrial process Industrial processes are procedures involving chemical A chemical substance is a form of matter having constant chemical composition and characteristic propert ...
, also called Hock process. It involves the partial
oxidation Redox (reduction–oxidation, pronunciation: or ) is a type of chemical reaction A chemical reaction is a process that leads to the chemical transformation of one set of chemical substance A chemical substance is a form of matter ...

oxidation
of
cumene Cumene (isopropylbenzene) is an organic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, prope ...

cumene
(isopropylbenzene) via the
Hock rearrangementThe cumene process (cumene–phenol process, Hock process) is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term stems from cumene (isopropyl benzene), the intermediate material during the process. It was i ...
: Compared to most other processes, the cumene process uses relatively mild conditions and relatively inexpensive raw materials. For the process to be economical, both phenol and the acetone by-product must be in demand. In 2010, worldwide demand for acetone was approximately 6.7 million tonnes, 83 percent of which was satisfied with acetone produced by the cumene process. A route analogous to the cumene process begins with
cyclohexylbenzene Cyclohexylbenzene is the organic compound , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen chemical bond, bonds. Due to carbon's ability to Catenatio ...

cyclohexylbenzene
. It is
oxidized (mild reducing agent) are added to powdered potassium permanganate (strong oxidizing agent), a violent redox reaction accompanied by self-ignition starts. Redox (reduction–oxidation, pronunciation: or ) is a type of chemical reaction A ...

oxidized
to a
hydroperoxide Hydroperoxides or peroxols are Chemical compound, compounds containing the hydroperoxide functional group (ROOH). If the R is organic, the compounds are called organic hydroperoxides. Such compounds are a subset of organic peroxides, which have t ...

hydroperoxide
, akin to the production of
cumene hydroperoxide Cumene hydroperoxide is the organic compound with the formula C6H5CMe2OOH (Me = CH3). An oily liquid, it is classified as an organic peroxide, organic hydroperoxide. Products of decomposition of cumene hydroperoxide are methylstyrene, acetopheno ...

cumene hydroperoxide
. Via the Hock rearrangement, cyclohexylbenzene hydroperoxide cleaves to give phenol and
cyclohexanone Cyclohexanone is the organic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, beh ...

cyclohexanone
. Cyclohexanone is an important precursor to some
nylon Nylon is a generic designation for a family of synthetic polymerSynthetic polymers are human-made polymers, often derived from petroleum oil. From the utility point of view they can be classified into three main categories: thermoplastics, ela ...

nylon
s.


Oxidation of benzene and toluene

The direct oxidation of
benzene Benzene is an organic Organic may refer to: * Organic, of or relating to an organism, a living entity * Organic, of or relating to an anatomical organ (anatomy), organ Chemistry * Organic matter, matter that has come from a once-living organ ...

benzene
to phenol is theoretically possible and of great interest, but it has not been commercialized: :C6H6 + O → C6H5OH
Nitrous oxide Nitrous oxide, commonly known as laughing gas, nitrous, or nos, is a chemical compound A chemical compound is a chemical substance A chemical substance is a form of matter In classical physics and general chemistry, matter is an ...
is a potentially "green" oxidant that is a more potent oxidant than O2. Routes for the generation of nitrous oxide however remain uncompetitive. An
electrosynthesis Electrosynthesis in chemistry Chemistry is the scientific Science () is a systematic enterprise that builds and organizes knowledge Knowledge is a familiarity or awareness, of someone or something, such as facts A fact is an ...
employing
alternating current Alternating current (AC) is an electric current An electric current is a stream of charged particle In physics Physics (from grc, φυσική (ἐπιστήμη), physikḗ (epistḗmē), knowledge of nature, from ''phýsis'' 'natu ...
gives phenol from benzene. The oxidation of
toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon Aromatic compounds are those chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entity, molecular enti ...

toluene
, as developed by
Dow Chemical The Dow Chemical Company (TDCC) is an American multinational corporation, multinational chemical corporation headquartered in Midland, Michigan, United States and is a subsidiary of Dow Inc. The company is among the three List of largest chemical ...
, involves copper-catalyzed reaction of molten sodium benzoate with air: :C6H5CH3 + 2 O2 → C6H5OH + CO2 + H2O The reaction is proposed to proceed via formation of benzyoylsalicylate.


Older methods

Early methods relied on extraction of phenol from coal derivatives or the hydrolysis of benzene derivatives.


Hydrolysis of benzenesulfonic acid

An early commercial route, developed by
Bayer Bayer Aktiengesellschaft, AG (; ) is a German multinational corporation, multinational pharmaceutical company, pharmaceutical and life sciences company and one of the largest pharmaceutical companies in the world. Headquartered in Leverkusen, ...

Bayer
and
Monsanto The Monsanto Company () was an American agrochemical An agrochemical or agrichemical, a contraction of ''agricultural chemical'', is a chemical A chemical substance is a form of matter having constant chemical composition and characteris ...

Monsanto
in the early 1900s, begins with the reaction of a strong base with
benzenesulfonic acid Benzenesulfonic acid (conjugate acid, conjugate base benzenesulfonate) is an organosulfur compound with the formula carbon, C6hydrogen, H6oxygen, O3sulfur, S. It is the simplest aromaticity, aromatic sulfonic acid. It forms white deliquescent sheet ...
. The conversion is represented by this idealized equation:Wittcoff, H.A., Reuben, B.G. Industrial Organic Chemicals in Perspective. Part One: Raw Materials and Manufacture. Wiley-Interscience, New York. 1980. :C6H5SO3H + 2 NaOH → C6H5OH + Na2SO3 + H2O


Hydrolysis of chlorobenzene

Chlorobenzene Chlorobenzene is an aromatic forms of benzene (top) combine to produce an average structure (bottom) In chemistry, aromaticity is a property of cyclic compound, cyclic (ring (chemistry), ring-shaped), plane (geometry), planar (flat) structures ...

Chlorobenzene
can be hydrolyzed to phenol using base (
Dow process The Dow process is the electrolytic An electrolyte is a substance that produces an conductivity (electrolytic), electrically conducting solution when dissolved in a polar solvent, such as water. The dissolved electrolyte separates into cations an ...
) or steam ( Raschig–Hooker process): :C6H5Cl + NaOH → C6H5OH + NaCl :C6H5Cl + H2O → C6H5OH + HCl These methods suffer from the cost of the chlorobenzene and the need to dispose of the chloride by product.


Coal pyrolysis

Phenol is also a recoverable byproduct of
coal Coal is a combustible , Germany ) , image_map = , map_caption = , map_width = 250px , capital = Berlin , coordinates = , largest_city = capital , languages_type = Official language , languages = German language, German , ...

coal
pyrolysis.Franck, H.-G., Stadelhofer, J.W. Industrial Aromatic Chemistry. Springer-Verlag, New York. 1988. pp. 148-155. In the Lummus Process, the oxidation of toluene to
benzoic acid Benzoic acid is a white (or colorless) solid with the formula C6H5CO2H. It is the simplest aromatic In chemistry Chemistry is the scientific Science () is a systematic enterprise that builds and organizes knowledge Know ...

benzoic acid
is conducted separately.


Miscellaneous methods

Phenyldiazonium Benzenediazonium chloride is an organic compound with the chemical formula, formula 6H5N2l. It is a salt of a diazonium compound, diazonium cation and chloride. It exists as a colourless solid that is soluble in polar solvents including water. ...
salts hydrolyze to phenol. The method is of no commercial interest since the precursor is expensive. :C6H5NH2 + HCl/NaNO2 → C6H5OH + N2 + H2O + NaCl :
Salicylic acid Salicylic acid is an organic compound with the formula HOC6H4CO2H. A colorless, bitter-tasting solid, it is a precursor to and a active metabolite, metabolite of aspirin (acetylsalicylic acid). It is a plant hormone, and has been listed by the ...

Salicylic acid
decarboxylates to phenol.


Uses

The major uses of phenol, consuming two thirds of its production, involve its conversion to precursors for plastics.
Condensation Condensation is the change of the state of matter In physics Physics is the natural science that studies matter, its Elementary particle, fundamental constituents, its Motion (physics), motion and behavior through Spacetime, space ...
with acetone gives
bisphenol-A Bisphenol A (BPA) is an organic synthetic compound with the chemical formula A chemical formula is a way of presenting information about the chemical proportions of atom An atom is the smallest unit of ordinary matter In classi ...
, a key precursor to
polycarbonate Polycarbonates (PC) are a group of thermoplastic A thermoplastic, or thermosoft plastic, is a plastic polymer A polymer (; Greek ''wikt:poly-, poly-'', "many" + ''wikt:-mer, -mer'', "part") is a Chemical substance, substance or material c ...

polycarbonate
s and
epoxide An epoxide is a cyclic ether with a three-atom ring. This ring approximates an equilateral triangle, which makes it ring strain, strained, and hence highly reactive, more so than other ethers. They are produced on a large scale for many applicat ...

epoxide
resins. Condensation of phenol, alkylphenols, or diphenols with
formaldehyde Formaldehyde ( , also ) (systematic nameA systematic name is a name given in a systematic way to one unique group, organism, object or chemical substance A chemical substance is a form of matter In classical physics and general chemist ...
gives
phenolic resin Phenol formaldehyde resins (PF) or phenolic resins (also infrequently called phenoplasts) are synthetic polymers obtained by the reaction of phenol or substituted phenol with formaldehyde. Used as the basis for Bakelite, PFs were the first commerc ...
s, a famous example of which is
Bakelite Bakelite ( ; sometimes spelled Baekelite) or polyoxybenzylmethylenglycolanhydride was the first plastic Plastics are a wide range of syntheticA synthetic is an artificial material produced by organic chemistry, organic chemical synthesis. ...

Bakelite
. Partial
hydrogenation Hydrogenation is a chemical reaction A chemical reaction is a process that leads to the chemical transformation of one set of chemical substance A chemical substance is a form of matter In classical physics and general chemistry, m ...

hydrogenation
of phenol gives
cyclohexanone Cyclohexanone is the organic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, beh ...

cyclohexanone
, a precursor to
nylon Nylon is a generic designation for a family of synthetic polymerSynthetic polymers are human-made polymers, often derived from petroleum oil. From the utility point of view they can be classified into three main categories: thermoplastics, ela ...

nylon
. Nonionic
detergent A detergent is a surfactant Surfactants are compounds that lower the (or interfacial tension) between two liquids, between a gas and a liquid, or between a liquid and a solid. Surfactants may act as s, agents, , s, or s. The word "surfact ...
s are produced by alkylation of phenol to give the
alkylphenol Alkylphenols are a family of organic compounds obtained by the alkylation of phenol Phenol (also called carbolic acid) is an aromatic forms of benzene (top) combine to produce an average structure (bottom) In chemistry, aromaticity is a pro ...
s, e.g.,
nonylphenol Nonylphenols are a family of closely related organic compounds composed of phenol bearing a 9 carbon-tail. Nonylphenols can come in numerous structures, all of which may be considered alkylphenols. They are used in manufacturing antioxidants, lubr ...

nonylphenol
, which are then subjected to
ethoxylation Ethoxylation is a chemical reaction A chemical reaction is a process that leads to the chemical transformation of one set of chemical substances to another. Classically, chemical A chemical substance is a form of matter having constant chem ...
. Phenol is also a versatile precursor to a large collection of drugs, most notably
aspirin Aspirin, also known as acetylsalicylic acid (ASA), is a medication used to reduce pain, fever, or inflammation. Specific inflammatory conditions which aspirin is used to treat include Kawasaki disease, pericarditis, and rheumatic fever. Aspirin ...

aspirin
but also many
herbicide Herbicides (, ), also commonly known as weedkillers, are substances used to control unwanted plant Plants are predominantly photosynthetic Photosynthesis is a process used by plants and other organisms to Energy transformation, conv ...
s and
pharmaceutical drug A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug Uncoated tablets, consisting of about 90% acetylsalicylic acid, along with a minor amount of inert fillers and binders. Aspir ...
s. Phenol is a component in liquid–liquid
phenol–chloroform extraction Phenol–chloroform extraction is a liquid-liquid extraction technique in molecular biology used to separate nucleic acids from proteins and lipids. Process Aqueous samples, lysed cells, or homogenised tissue are mixed with equal volumes of a pheno ...
technique used in
molecular biology Molecular biology is the branch of biology Biology is the natural science that studies life and living organisms, including their anatomy, physical structure, Biochemistry, chemical processes, Molecular biology, molecular interactions, P ...
for obtaining
nucleic acid Nucleic acids are biopolymer Biopolymers are natural polymer A polymer (; Greek ''wikt:poly-, poly-'', "many" + ''wikt:-mer, -mer'', "part") is a Chemical substance, substance or material consisting of very large molecules, or macromolecule ...

nucleic acid
s from tissues or cell culture samples. Depending on the pH of the solution either
DNA Deoxyribonucleic acid (; DNA) is a molecule A scanning tunneling microscopy image of pentacene molecules, which consist of linear chains of five carbon rings. A molecule is an electrically Electricity is the set of physical ...

DNA
or
RNA Ribonucleic acid (RNA) is a polymer A polymer (; Greek ''wikt:poly-, poly-'', "many" + ''wikt:-mer, -mer'', "part") is a Chemical substance, substance or material consisting of very large molecules, or macromolecules, composed of many Re ...

RNA
can be extracted.


Medical

Phenol is widely used as an antiseptic, its use was pioneered by Joseph Lister (see
History History (from Greek#REDIRECT Greek Greek may refer to: Greece Anything of, from, or related to Greece Greece ( el, Ελλάδα, , ), officially the Hellenic Republic, is a country located in Southeast Europe. Its population is approxima ...
section). From the early 1900s to the 1970s it was used in the production of
carbolic soap Carbolic soap, sometimes referred to as red soap, is a mildly antiseptic soap containing carbolic acid and/or cresylic acid, both of which are phenols derived from either coal tar or petroleum sources. In 1834, German chemist Friedlieb Ferdinand ...
. Concentrated phenol liquids are commonly used for permanent treatment of ingrown toe and finger nails, a procedure known as a chemical
matrixectomy Image:ToeGN.jpg, 300px, Toe healing process after nail removal, right Surgical treatments of ingrown toenails include a number of different options. If conservative treatment of a minor ingrown toenail does not succeed or if the ingrown toenail ...
. The procedure was first described by Otto Boll in 1945. Since that time it has become the chemical of choice for chemical matrixectomies performed by podiatrists. Concentrated liquid phenol can be used topically as a local anesthetic for otology procedures, such as myringotomy and tympanotomy tube placement, as an alternative to general anesthesia or other local anesthetics. It also has hemostatic and antiseptic qualities that make it ideal for this use. Phenol spray, usually at 1.4% phenol as an active ingredient, is used medically to help sore throat. It is the active ingredient in some oral analgesics such as
Chloraseptic Chloraseptic is an American brand of oral analgesic that is produced by Tarrytown, NY-based Prestige Brands, Prestige Brands Inc., used for the relief of sore throat and mouth pain. Its active ingredient is phenol (just in Sore Throat Spray, not ...
spray, TCP and
Carmex Carmex is a brand of lip balm Homemade lip balms Lip balm or lip salve is a wax , a typical wax ester. Image:Beeswax foundation.jpg, Commercial honeycomb foundation, made by pressing beeswax between patterned metal rollers. Waxes are a diverse ...
, commonly used to temporarily treat
pharyngitis Pharyngitis is inflammation Inflammation (from la, inflammatio) is part of the complex biological response of body tissues to harmful stimuli, such as pathogen In biology Biology is the natural science that studies life and living o ...

pharyngitis
.


Niche uses

Phenol is so inexpensive that it attracts many small-scale uses. It is a component of industrial
paint stripper Paint stripper, or paint remover, is a chemical product designed to remove paint, wood finishing, finishes, and coatings while also cleaning the underlying surface. The product's material safety data sheet provides more safety information than i ...
s used in the aviation industry for the removal of epoxy, polyurethane and other chemically resistant coatings. Phenol derivatives have been used in the preparation of
cosmetics Cosmetics are constituted mixtures of chemical compound A chemical compound is a chemical substance A chemical substance is a form of matter In classical physics and general chemistry, matter is any substance that has mass and take ...
including
sunscreen Sunscreen, also known as sunblock or suntan lotion, is a photoprotective topical A topical medication is a medication A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug use ...
s,
hair coloring Hair coloring, or hair dyeing, is the practice of changing the hair color. The main reasons for this are beauty, cosmetic: to cover Gray hair, gray or white hair, to change to a color regarded as more fashionable or desirable, or to restore the or ...
s, preparations, as well as in skin toners/exfoliators. However, due to safety concerns, phenol is banned from use in cosmetic products in the
European Union The European Union (EU) is a political and economic union of member states that are located primarily in Europe Europe is a which is also recognised as part of , located entirely in the and mostly in the . It comprises the wester ...

European Union
and
Canada Canada is a country in the northern part of North America North America is a continent A continent is any of several large landmasses. Generally identified by convention (norm), convention rather than any strict criteria, ...

Canada
.


History

Phenol was discovered in 1834 by
Friedlieb Ferdinand Runge Friedlieb Ferdinand Runge (8 February 1794 – 25 March 1867) was a German German(s) may refer to: Common uses * of or related to Germany * Germans, Germanic ethnic group, citizens of Germany or people of German ancestry * For citizens of Ge ...
, who extracted it (in impure form) from
coal tar Coal tar is a thick dark liquid which is a by-product of the production of coke and coal gas Coal gas is a flammable gaseous fuel Fuel gas is any one of a number of fuels that under ordinary conditions are gaseous. Many fuel gases are c ...
. Runge called phenol "Karbolsäure" (coal-oil-acid, carbolic acid). Coal tar remained the primary source until the development of the
petrochemical industry The petrochemical industry is concerned with the production and trade of petrochemicals Petrochemicals (sometimes abbreviated as petchems) are the chemical products obtained from petroleum Petroleum (), also known as crude oil and oil, is a ...
. In 1841, the French chemist
Auguste Laurent Auguste Laurent (14 November 1807 – 15 April 1853) was a French chemist A chemist (from Greek ''chēm(ía)'' alchemy; replacing ''chymist'' from Medieval Latin ''alchemist'') is a scientist A scientist is a person who conducts Scientific me ...
obtained phenol in pure form. In 1836, Auguste Laurent coined the name "phène" for benzene; this is the root of the word "phenol" and "
phenyl In organic chemistry Organic chemistry is a branch of that studies the structure, properties and reactions of s, which contain in .Clayden, J.; Greeves, N. and Warren, S. (2012) ''Organic Chemistry''. Oxford University Press. pp. 1–15. . Stu ...
". In 1843, French chemist Charles Gerhardt coined the name "phénol". The
antiseptic Antiseptics (from Greek ἀντί ''anti'', "against" and σηπτικός ''sēptikos'', "putrefactive") are antimicrobial substances that are applied to living tissue Tissue may refer to: Biology * Tissue (biology), an ensemble of similar cel ...

antiseptic
properties of phenol were used by Sir
Joseph Lister Joseph Lister, Baron Lister of Lyme Regis (5 April 182710 February 1912), was a British surgeon In modern medicine Medicine is the science Science (from the Latin word ''scientia'', meaning "knowledge") is a systematic enterpri ...
(1827–1912) in his pioneering technique of antiseptic surgery. Lister decided that the wounds themselves had to be thoroughly cleaned. He then covered the wounds with a piece of rag or lint covered in phenol, or carbolic acid as he called it. The skin irritation caused by continual exposure to phenol eventually led to the introduction of aseptic (germ-free) techniques in surgery. Joseph Lister was a student at University College London under Robert Liston, later rising to the rank of Surgeon at Glasgow Royal Infirmary. Lister experimented with cloths covered in carbolic acid after studying the works and experiments of his contemporary, Louis Pasteur in sterilizing various biological media. Lister was inspired to try to find a way to sterilize living wounds, which could not be done with the heat required by Pasteur's experiments. In examining Pasteur's research, Lister began to piece together his theory: that patients were being killed by germs. He theorized that if germs could be killed or prevented, no infection would occur. Lister reasoned that a chemical could be used to destroy the micro-organisms that cause infection. Meanwhile, in Carlisle, England, officials were experimenting with a sewage treatment, using carbolic acid to reduce the smell of sewage cess pools. Having heard of these developments and having himself previously experimented with other chemicals for antiseptic purposes without much success, Lister decided to try carbolic acid as a wound antiseptic. He had his first chance on August 12, 1865, when he received a patient: an eleven-year-old boy with a tibia bone fracture which pierced the skin of his lower leg. Ordinarily, amputation would be the only solution. However, Lister decided to try carbolic acid. After setting the bone and supporting the leg with splints, Lister soaked clean cotton towels in undiluted carbolic acid and applied them to the wound, covered with a layer of tin foil, leaving them for four days. When he checked the wound, Lister was pleasantly surprised to find no signs of infection, just redness near the edges of the wound from mild burning by the carbolic acid. Reapplying fresh bandages with diluted carbolic acid, the boy was able to walk home after about six weeks of treatment.
By 16 March 1867, when the first results of Lister's work were published in the Lancet, he had treated a total of eleven patients using his new antiseptic method. Of those, only one had died, and that was through a complication that was nothing to do with Lister's wound-dressing technique. Now, for the first time, patients with compound fractures were likely to leave the hospital with all their limbs intact :— Richard Hollingham, ''Blood and Guts: A History of Surgery'', p. 62
Before antiseptic operations were introduced at the hospital, there were sixteen deaths in thirty-five surgical cases. Almost one in every two patients died. After antiseptic surgery was introduced in the summer of 1865, there were only six deaths in forty cases. The mortality rate had dropped from almost 50 per cent to around 15 per cent. It was a remarkable achievement :— Richard Hollingham, ''Blood and Guts: A History of Surgery'', p. 63
Phenol was the main ingredient of the Carbolic Smoke Ball, an ineffective device marketed in London in the 19th century as protection against influenza and other ailments, and the subject of the famous law case ''
Carlill v Carbolic Smoke Ball Company ''Carlill v Carbolic Smoke Ball Company'' [1892EWCA Civ 1is an English contract law decision by the English Court of Appeal, Court of Appeal, which held an advertisement containing certain terms to get a reward constituted a binding unilateral off ...
''.


Second World War

The toxic effect of phenol on the central nervous system, discussed below, causes sudden collapse and loss of consciousness in both humans and animals; a state of cramping precedes these symptoms because of the motor activity controlled by the central nervous system. Injections of phenol were used as a means of individual execution by Nazi Germany during the Second World War.''The Experiments''
by Peter Tyson. NOVA
It was originally used by the Nazis in 1939 as part of the
Aktion T4 ''Aktion T4'' (German, ) was a campaign of mass murder #REDIRECT Mass murder Mass murder is the act of murder Murder is the unlawful killing of another human Humans (''Homo sapiens'') are the most populous and widespread spec ...
euthanasia program.''The Nazi Doctors''
Chapter 14, Killing with Syringes: Phenol Injections. By Dr. Robert Jay Lifton
The Germans learned that extermination of smaller groups was more economical by injection of each victim with phenol. Phenol injections were given to thousands of people.
Maximilian Kolbe Maximilian Maria Kolbe (born Rajmund Kolbe; pl, Maksymilian Maria Kolbe ; 8 January 1894 – 14 August 1941), venerated as Saint Maximilian Kolbe, was a Polish Catholic The Catholic Church, also known as the Roman Catholic Church, i ...

Maximilian Kolbe
was also killed with a phenol injection after surviving two weeks of dehydration and starvation in
Auschwitz The Auschwitz concentration camp () was a complex of over 40 concentration In chemistry Chemistry is the scientific Science () is a systematic enterprise that builds and organizes knowledge Knowledge is a familiarity or ...

Auschwitz
when he volunteered to die in place of . Approximately one gram is sufficient to cause death.


Occurrences

Phenol is a normal metabolic product, excreted in quantities up to 40 mg/L in human urine. The
temporal gland Temporins are a family of peptide Peptides (from Greek language Greek ( el, label=Modern Greek Modern Greek (, , or , ''Kiní Neoellinikí Glóssa''), generally referred to by speakers simply as Greek (, ), refers collectively to the d ...
secretion of male
elephant Elephants are the largest existing land animals. Three living species In biology, a species is the basic unit of biological classification, classification and a taxonomic rank of an organism, as well as a unit of biodiversity. A specie ...

elephant
s showed the presence of phenol and 4-methylphenol during
musth Musth or must (; ur, مست, from Persian, )''The Oxford Dictionary and Thesaurus: American edition'', published 1996 by Oxford University Press; p. 984 is a periodic condition in bull (male) elephants characterized by highly aggressive behavior ...

musth
. It is also one of the chemical compounds found in
castoreum Castoreum is a yellowish exudate from the castor sacs of mature beaver Beavers are large, semiaquatic In biology Biology is the natural science that studies life and living organisms, including their anatomy, physical structure, ...
. This compound is ingested from the plants the beaver eats.


Occurrence in whisky

Phenol is a measurable component in the aroma and taste of the distinctive Islay scotch whisky, generally ~30 ppm, but it can be over 160ppm in the malted
barley Barley (''Hordeum vulgare''), a member of the grass family Poaceae () or Gramineae () is a large and nearly ubiquitous family In human society, family (from la, familia) is a group of people related either by consanguinity (by recogn ...

barley
used to produce
whisky Whisky or whiskey is a type of distilled alcoholic beverage made from fermented Fermentation is a metabolic Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life Life is a characteristic that ...

whisky
. This amount is different from and presumably higher than the amount in the distillate.


Biodegradation

'' Cryptanaerobacter phenolicus'' is a bacterium species that produces
benzoate Benzoic acid is a white (or colorless) solid with the formula C6H5CO2H. It is the simplest aromaticity, aromatic carboxylic acid. The name is derived from benzoin (resin), gum benzoin, which was for a long time its only source. Benzoic acid oc ...

benzoate
from phenol via 4-hydroxybenzoate. '' Rhodococcus phenolicus'' is a bacterium species able to degrade phenol as sole carbon source.


Toxicity

Phenol and its vapors are corrosive to the eyes, the skin, and the respiratory tract. Its corrosive effect on skin and mucous membranes is due to a protein-degenerating effect. Repeated or prolonged skin contact with phenol may cause
dermatitis Dermatitis is inflammation of the Human skin, skin, typically characterized by itchiness, erythema, redness and a rash. In cases of short duration, there may be small blisters, while in long-term cases the skin may become lichenification, thick ...

dermatitis
, or even second and third-degree burns. Inhalation of phenol vapor may cause lung
edema Edema, also spelled oedema, and also known as fluid retention, dropsy, hydropsy and swelling, is the build-up of fluid in the body's tissue Tissue may refer to: Biology * Tissue (biology), an ensemble of similar cells that together carry out a ...

edema
. The substance may cause harmful effects on the central nervous system and heart, resulting in dysrhythmia,
seizure An epileptic seizure, formally known as a seizure, is a period of symptom Signs and symptoms are the observed or detectable signs, and experienced symptoms of an illness, injury, or condition. A sign for example may be a higher or lower tem ...
s, and
coma A coma is a deep state of prolonged unconsciousness Unconsciousness is a state which occurs when the ability to maintain an consciousness, awareness of self and environment is lost. It involves a complete, or near-complete, lack of responsiv ...
. The
kidney The kidneys are two reddish-brown bean-shaped organs An organ is a group of tissues with similar functions. Plant life and animal life rely on many organs that co-exist in organ systems. A given organ's tissues can be broadly categorized ...

kidney
s may be affected as well. Long-term or repeated exposure of the substance may have harmful effects on the
liver The liver is an organ Organ may refer to: Biology * Organ (anatomy) An organ is a group of Tissue (biology), tissues with similar functions. Plant life and animal life rely on many organs that co-exist in organ systems. A given organ's t ...

liver
and
kidney The kidneys are two reddish-brown bean-shaped organs An organ is a group of tissues with similar functions. Plant life and animal life rely on many organs that co-exist in organ systems. A given organ's tissues can be broadly categorized ...

kidney
s. There is no evidence that phenol causes
cancer Cancer is a group of diseases involving abnormal cell growth with the potential to invade or spread to other parts of the body. These contrast with benign tumor A benign tumor is a mass of cells Cell most often refers to: * Cell (biolo ...

cancer
in humans. Besides its
hydrophobic In chemistry Chemistry is the scientific Science () is a systematic enterprise that builds and organizes knowledge Knowledge is a familiarity or awareness, of someone or something, such as facts A fact is an occurrence ...
effects, another mechanism for the toxicity of phenol may be the formation of free radical, radicals. Since phenol is absorbed through the skin relatively quickly, systemic poisoning can occur in addition to the local caustic burns. Resorptive poisoning by a large quantity of phenol can occur even with only a small area of skin, rapidly leading to paralysis of the central nervous system and a severe drop in body temperature. The for oral toxicity is less than 500 mg/kg for dogs, rabbits, or mice; the minimum lethal human dose was cited as 140 mg/kg. The Agency for Toxic Substances and Disease Registry (ATSDR), U.S. Department of Health and Human Services states the fatal dose for ingestion of phenol is from 1 to 32 g. Chemical burns from human skin, skin exposures can be decontaminated by washing with polyethylene glycol, isopropyl alcohol, or perhaps even copious amounts of water. Removal of contaminated clothing is required, as well as immediate hospital treatment for large splashes. This is particularly important if the phenol is mixed with phenol-chloroform extraction, chloroform (a commonly used mixture in molecular biology for
DNA Deoxyribonucleic acid (; DNA) is a molecule A scanning tunneling microscopy image of pentacene molecules, which consist of linear chains of five carbon rings. A molecule is an electrically Electricity is the set of physical ...

DNA
and
RNA Ribonucleic acid (RNA) is a polymer A polymer (; Greek ''wikt:poly-, poly-'', "many" + ''wikt:-mer, -mer'', "part") is a Chemical substance, substance or material consisting of very large molecules, or macromolecules, composed of many Re ...

RNA
purification). Phenol is also a reproductive toxin causing increased risk of miscarriage and low birth weight indicating retarded development in utero.


Phenols

The word ''phenol'' is also used to refer to any compound that contains a six-membered aromatic ring, bonded directly to a hydroxyl group (-OH). Thus, phenols are a class of
organic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behavior and the changes they undergo during ...
s of which the phenol discussed in this article is the simplest member.


See also

*Bamberger rearrangement *Claisen rearrangement *Cresol *Fries rearrangement *Polyphenol


References


External links


International Chemical Safety Card 0070National Pollutant Inventory: Phenol Fact SheetCDC - Phenol - NIOSH Workplace Safety and Health Topic
{{Authority control Antiseptics Commodity chemicals Hazardous air pollutants Oxoacids Phenyl compounds 1834 in science