Phenol

carbolic acidphenoxidephenolatephenolicphenoxy5% phenolalkyl phenolsaromatic alcoholbisphenolatecarbolic
Phenol is an aromatic organic compound with the molecular formula C 6 H 5 OH.wikipedia
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Bakelite

Bakelite Corporationphenolic resinBakelite Corp.
Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical drugs. Condensation of phenol, alkylphenols, or diphenols with formaldehyde gives phenolic resins, a famous example of which is Bakelite.
It is a thermosetting phenol formaldehyde resin, formed from a condensation reaction of phenol with formaldehyde.

Polycarbonate

lexanpolycarbonatesPC
Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical drugs. Condensation with acetone gives bisphenol-A, a key precursor to polycarbonates and epoxide resins.
The diphenoxide (Na 2 (OC 6 H 4 ) 2 CMe 2 ) reacts with phosgene to give a chloroformate, which subsequently is attacked by another phenoxide.

Sodium phenoxide

sodium phenolatephenoxide
The sodium salt of phenol, sodium phenoxide, is far more water-soluble.
Its anion, phenoxide, also known as phenolate, is the conjugate base of phenol.

Aniline

aniline dyeaniline dyesanilines
However, phenol's ring is so strongly activated—second only to aniline—that bromination or chlorination of phenol leads to substitution on all carbon atoms ortho and para to the hydroxy group, not only on one carbon.
Aniline can alternatively be prepared from ammonia and phenol derived from the cumene process.

Petroleum

crude oiloilcrude
Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 billion kg/year) from petroleum.
Combination happened in a similar fashion as phenol and formaldehyde molecules react to urea-formaldehyde resins, but kerogen formation occurred in a more complex manner due to a bigger variety of reactants.

Picric acid

melinitelydditetrinitrophenol
Phenol reacts with dilute nitric acid at room temperature to give a mixture of 2-nitrophenol and 4-nitrophenol while with concentrated nitric acid, more nitro groups get substituted on the ring to give 2,4,6-trinitrophenol which is known as picric acid.
Its synthesis from phenol, and the correct determination of its formula, were successfully accomplished in 1841.

Cumene process

air-oxidation of cumene
The dominant current route, accounting for 95% of production (2003), is the cumene process, which uses benzene and propene as feedstock and involves the partial oxidation of cumene (isopropylbenzene) via the Hock rearrangement:
The cumene process (cumene-phenol process, Hock process) is an industrial process for synthesizing phenol and acetone from benzene and propylene.

Benzene

benzene ringbenzolbenzene rings
Phenol is reduced to benzene when it is distilled with zinc dust, or when phenol vapour is passed over granules of zinc at 400 °C:
In 1836, the French chemist Auguste Laurent named the substance "phène"; this word has become the root of the English word "phenol", which is hydroxylated benzene, and "phenyl", the radical formed by abstraction of a hydrogen atom (free radical H•) from benzene.

Acetone

methyl ketonepropanone(CH 3 ) 2 CO
In support of the second explanation, the pK a of the enol of acetone in water is 10.9, making it only slightly less acidic than phenol (pK a 10.0).
In the cumene process, benzene is alkylated with propylene to produce cumene, which is oxidized by air to produce phenol and acetone:

Acid dissociation constant

p''K'' a pKapK a
In support of the second explanation, the pK a of the enol of acetone in water is 10.9, making it only slightly less acidic than phenol (pK a 10.0).
In aromatic compounds, such as phenol, which have an OH substituent, conjugation with the aromatic ring as a whole greatly increases the stability of the deprotonated form.

Electrophilic aromatic substitution

electrophilic substitutionsubstitutionEAS
Phenol is highly reactive toward electrophilic aromatic substitution as the oxygen atom's pi electrons donate electron density into the ring.
Examples of activated aromatic rings are toluene, aniline and phenol.

Phenol formaldehyde resin

phenolic resinphenolicphenol-formaldehyde resin
Condensation of phenol, alkylphenols, or diphenols with formaldehyde gives phenolic resins, a famous example of which is Bakelite.
Phenol formaldehyde resins (PF) or phenolic resins are synthetic polymers obtained by the reaction of phenol or substituted phenol with formaldehyde.

Nonylphenol

4-Nonylphenolalkylphenol ethoxylates
Nonionic detergents are produced by alkylation of phenol to give the alkylphenols, e.g., nonylphenol, which are then subjected to ethoxylation.
Nonylphenols, from the Latin nōnus (number 9) and phenol, are a family of closely related organic compounds composed of phenol bearing a 9 carbon-tail.

Raschig–Hooker process

hydrolysis of chlorobenzene, using base (Dow's Process) or steam (Raschig–Hooker process):
The Raschig–Hooker process is a chemical process for the production of phenol, named after German chemist Friedrich Raschig.

Amine

aminoaminesamino group
The phenoxide anion has a similar nucleophilicity to free amines, with the further advantage that its conjugate acid (neutral phenol) does not become entirely deactivated as a nucleophile even in moderately acidic conditions.
Aryldiazonium couple with electron-rich aromatic compounds such as a phenol to form azo compounds.

Diazomethane

methyldiazonium
When phenol is reacted with diazomethane in the presence of boron trifluoride (BF 3 ), anisole is obtained as the main product and nitrogen gas as a byproduct.
Diazomethane reacts with alcohols or phenols in presence of boron trifluoride (BF 3 ) to give methyl ethers.

Coal tar

tarcoal-tarcoal tar pitch
Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 billion kg/year) from petroleum.
Others include benzene, toluene, xylenes, cumenes, coumarone, indene, benzofuran, naphthalene and methyl-naphthalenes, acenaphthene, fluorene, phenol, cresols, pyridine, picolines, phenanthracene, carbazole, quinolines, fluoranthene.

Keto–enol tautomerism

keto-enol tautomerismenolizationketo-enol tautomerization
Phenol exhibits keto-enol tautomerism with its unstable keto tautomer cyclohexadienone, but only a tiny fraction of phenol exists as the keto form.
In certain aromatic compounds such as phenol, the enol is important due to the aromatic character of the enol but not the keto form.

Ethoxylation

ethoxylatedethoxylatealcohol ethoxylates
Nonionic detergents are produced by alkylation of phenol to give the alkylphenols, e.g., nonylphenol, which are then subjected to ethoxylation.
In the usual application, alcohols and phenols are converted into R(OC 2 H 4 ) n OH where n ranges from 1 to 10. Such compounds are called alcohol ethoxylates.

Cumene

isopropylbenzeneCH(CH 3 ) 2
The dominant current route, accounting for 95% of production (2003), is the cumene process, which uses benzene and propene as feedstock and involves the partial oxidation of cumene (isopropylbenzene) via the Hock rearrangement:
Nearly all the cumene that is produced as a pure compound on an industrial scale is converted to cumene hydroperoxide, which is an intermediate in the synthesis of other industrially important chemicals, primarily phenol and acetone.

Plastic

plasticsadditivesynthetic plastic
The first plastic based on a synthetic polymer was made from phenol and formaldehyde, with the first viable and cheap synthesis methods invented in 1907, by Leo Hendrik Baekeland, a Belgian-born American living in New York state.

Alkylphenol

alkylphenolsalkylphenol ethoxylatesoctylphenol
Nonionic detergents are produced by alkylation of phenol to give the alkylphenols, e.g., nonylphenol, which are then subjected to ethoxylation.
Alkylphenols are a family of organic compounds obtained by the alkylation of phenols.

Bisphenol A

BPAbisphenol-Abisphenol A (BPA)
Condensation with acetone gives bisphenol-A, a key precursor to polycarbonates and epoxide resins.
This compound is synthesized by the condensation of acetone (hence the suffix A in the name) with two equivalents of phenol.

Dow Chemical Company

DowDow ChemicalThe Dow Chemical Company
oxidation of toluene, as developed by Dow Chemical:
Within twenty years, Dow had become a major producer of agricultural chemicals, elemental chlorine, phenol and other dyestuffs, and magnesium metal.

Carbolic soap

coal tar soap
From the early 1900s to the 1970s it was used as a soap, known as carbolic soap.
Carbolic 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.