PHENOL (BENZENOL)

Phenol (benzenol) is an aromatic organic compound with the molecular formula C₆H₅OH, consisting of a hydroxyl group directly bonded to a benzene ring, which increases its acidity through resonance stabilization of the phenoxide ion.
Phenol (benzenol) is a white crystalline, volatile, and toxic compound with a characteristic odor, moderately soluble in water and readily soluble in organic solvents.
Phenol (benzenol) is a major industrial chemical primarily used as a precursor in the manufacture of plastics, phenolic resins, bisphenol A, pharmaceuticals, detergents, dyes, and numerous other chemical intermediates.

CAS Number: 108-95-2
EC Number: 203-632-7
Molecular Formula: C6H6O
Molecular Weight: 94.11 g/mol

Synonyms: phenol, 108-95-2, carbolic acid, Hydroxybenzene, Phenic acid, Oxybenzene, Benzenol, Phenylic acid, Phenylic alcohol, Monophenol, Phenyl hydrate, Phenyl hydroxide, PhOH, Monohydroxybenzene, Paoscle, Izal, Phenyl alcohol, Phenole, Phenol alcohol, Acide carbolique, Phenol, liquefied, Fenolo, Carbolsaure, Fenol, Liquid phenol, Liquefied phenol, Phenol, pure, Fenosmolin, Fenosmoline, Rcra waste number U188, Liquified Phenol, Phenol, molten, Carbolicum acidum, NCI-C50124, Baker's P & S liquid & Ointment, Baker's P and S Liquid and Ointment, Caswell No. 649, 2-allphenol, Phenol, liquified, Carbolsaeure, Karbolsaeure, DTXSID5021124, Phenol,liquified, NSC-36808, 339NCG44TV, ENT-1814, DTXCID501124, CHEBI:15882, NSC36808, Phylorinol, Topcare, Ulcerease, Carbol, Acid Carbolicum, Fungus Fighter, Fungus Fighte, Liver Supplement, Sore Throat, Fortinia ID, Acidum Carbolicum, ABC Sore Throat, CVS Sore Throat, HEB Sore Throat, Phenolate, Sodium, Sore Throat Spray, Meijer Sore Throat, Sore Throat Cherry, Rugby Cherry Flavor, Sore Throat Menthol, Topcare Sore Throat, S.b. ward, PUBLIX Sore Throat, Walgreens Sore Throat, TopCare Cherry Flavor, RefChem:6668, Sore Throat Readyincase, Vortex Moisturizer Oral, DRx Choice Sore Throat, CVS Sore Throat Cherry, Wild Horse 777 Oral, Castellani Paint 1.5%, Good Neighbor Sore Throat, Sore Throat Relief Cherry, Pain Relieving Petro Carbo, Sore Throat Relief Menthol, NICE SORE THROAT Cherry, CEPASTAT EXTRA STRENGTH, NICE SORE THROAT Spearmint, CHLORASEPTIC SORE THROAT, HEB Sore Throat Cherry Flavor, Chloraseptic Sore Throat Cherry, Chloraseptic Sore Throat Citrus, ABC Sore Throat Menthol Flavor, CVS Sore Throat Menthol Flavor, HEB Sore Throat Menthol Flavor, Chloraseptic Sore Throat Menthol, Chloraseptic Warming Sore Throat, NICE SORE THROAT Honey Lemon, Sore Throat Relief Cherry Flavor, Diabetic Tussin Sore Throat Cherry, phenol 0.6% anesthetic oral rinse, PUBLIX Sore Throat Menthol Flavor, Topcare Sore Throat Menthol Flavor, Walgreens Sore Throat Cherry Flavor, DRx Choice Sore Throat Menthol Flavor, Eos Medicated Pain Relieving Lip Balm, Sterile Diluent for Allergenic Extract, Bestmade Natural Products Carbolic Acid, Good Neighbor Sore Throat Cherry Flavor, Chloraseptic Childrens Sore Throat Cherry, PUBLIX Sore Throat Fast Relief Oral Anesthetic, CVS Health Sore Throat Fast Relief Oral Anesthetic, 203-632-7, hydron;phenoxide, Phenosmolin, Benzene, hydroxy-, Fenolo [Italian], Phenole [German], Campho-Phenique Gel, Phenol [JAN], Phenic, Carbolsaure [German], Campho-Phenique Liquid, Fenol [Dutch, Polish], MFCD00002143, NSC 36808, Monohydroxy benzene, UN 2312 (molten), Acide carbolique [French], UN 1671 (solid), Campho-Phenique Cold Sore Gel, Phenic alcohol, Synthetic phenol, Phenol, dimer, RCRA waste no. U188, UN2312, UN2821, AI3-01814, 27073-41-2, CHEMBL14060, Phenol, Glass Distilled Under Argon, 17442-59-0, Phenol, solid [UN1671] [Poison], Phenol, molten [UN2312] [Poison], NCGC00091454-04, Phenol, >=99.0%, IPH, phenylalcohol, hydroxy benzene, Phenol 100 microg/mL in Methanol, Phenol, liquid, Phenol, solid, Benzenol; Hydroxybenzene; NSC 36808, Baker's p and s, CAS-108-95-2, CCRIS 504, FEMA No. 3223, HSDB 113, (14C)Phenol, Phenol [USP:JAN], PHENOL (2,3,4,5,6-D5), EINECS 203-632-7, EPA Pesticide Chemical Code 064001, arenols, UNII-339NCG44TV, Benzophenol, Hydrozybenzene, acide phenique, Hydroxy-benzene, Phenol liquid, Phenol molten, Phenol synthetic, Pandy's reagent, Cepastat lozenges, Phenol, labeled with carbon-14, Phenol (liquid), 2-phenyl alcohol, Phenol, synthetic, Phenol, ultrapure, Phenol ACS grade, Paoscle (TN), Carbolic acid liquid, Phenol (NIST), Phenol, ACS reagent, Carbolic acid, liquid, 63496-48-0, Water-Saturated Phenol, 1ai7, 1li2, 4i7l, PHENOL [VANDF], PHENOL [FHFI], PHENOL [HSDB], PHENOL [IARC], SCHEMBL48, Phenol (JP18/USP), PHENOL [USP-RS], PHENOL [WHO-DD], Phenol, detached crystals, PHENOL [II], PHENOL [MI], Phenol, >=99%, PHENOL [MART.], WLN: QR, Liquefied phenol (JP18), Salicylic Acid Impurity 9, bmse000290, bmse010026, C6H5OH, Fenol(DUTCH, POLISH), EC 203-632-7, SCHEMBL2350, SCHEMBL3290, SCHEMBL4037, PHENOL, 80% in ethanol, Phenol, LR, >=99%, SCHEMBL10428, MLS001065591, Phenol (CGA 73330), Phenol, for molecular biology, BIDD:ER0293, PHENOL [EP MONOGRAPH], SCHEMBL167552, SCHEMBL496777, SCHEMBL744464, Phenol, natural, 97%, FG, PHENOL [USP MONOGRAPH], SCHEMBL1642833, SCHEMBL1644243, SCHEMBL1644245, SCHEMBL1713042, SCHEMBL2640831, Cuticura pain relieving ointment, CARBOLICUM ACIDUM [HPUS], Phenol, AR, >=99.5%, PHENOL,LIQUIFIED [VANDF], SCHEMBL10939954, SCHEMBL20421902, SCHEMBL22284125, SCHEMBL22284137, BDBM26187, CHEBI:33853, Phenol for disinfection (JP18), MSK7905, 3f39, Phenol 10 microg/mL in Methanol, Phenol; Pirfenidone EP Impurity C, Tox21_113463, Tox21_201639, Tox21_300042, EBC-26037, Phenol 5000 microg/mL in Methanol, STL194294, AKOS000119025, Tox21_113463_1, DB03255, FP01241, NA 2821, Phenol, BioXtra, >=99.5% (GC), Phenol, SAJ first grade, >=98.0%, UN 1671, UN 2312, UN 2821, NCGC00091454-01, NCGC00091454-02, NCGC00091454-03, NCGC00091454-05, NCGC00091454-06, NCGC00091454-07, NCGC00254019-01, NCGC00259188-01, Phenol, JIS special grade, >=99.0%, 73607-76-8, BP-30160, METHYL SALICYLATE IMPURITY B [EP], SMR000568492, Phenol 1000 microg/mL in Dichloromethane, Phenol, PESTANAL(R), analytical standard, Liquified Phenol (contains 7-10 % water), METACRESOL IMPURITY A [EP IMPURITY], NS00010045, P1610, P2771, EN300-19432, C00146, D00033, Phenol, unstabilized, ReagentPlus(R), >=99%, R00328, SALICYLIC ACID IMPURITY C [EP IMPURITY], SBI-0653931.0001, HEXYLRESORCINOL IMPURITY A [EP IMPURITY], Phenol, p.a., ACS reagent, 99.5-100.5%, Q130336, Phenol, for molecular biology, ~90% (T), liquid, BRD-K76549667-001-04-6, F1908-0106, Phenol, unstabilized, purified by redistillation, >=99%, Z104473830, InChI=1/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7, Phenol, BioUltra, for molecular biology, >=99.5% (GC), Phenol, United States Pharmacopeia (USP) Reference Standard, Liquified Phenol, meets USP testing specifications, >=89.0%, Phenol, BioUltra, for molecular biology, TE-saturated, ~73% (T), phenol;phenol [jan];phenol, pure;phenol phenol [jan] phenol, pure, Phenol water-saturated, stabilised and with separate Tris buffer solution, Phenol, puriss. p.a., ACS reagent, reag. Ph. Eur., 99.0-100.5%, Phenol, contains hypophosphorous as stabilizer, loose crystals, ACS reagent, >=99.0%, Phenol, puriss., meets analytical specification of Ph. Eur., BP, USP, 99.5-100.5% (GC), Phenol, puriss., meets analytical specification of Ph. Eur., BP, USP, >=99.5% (GC), crystalline (detached)

Phenol (benzenol) is an aromatic organic compound consisting of a hydroxyl group (–OH) directly bonded to a benzene ring, with the molecular formula C₆H₆O.
The direct attachment of the hydroxyl group to the aromatic ring significantly influences its chemical behavior, increasing its acidity compared to aliphatic alcohols due to resonance stabilization of the phenoxide ion.

Phenol (benzenol) appears as a colorless to white crystalline solid at room temperature and may turn pink upon exposure to air and light due to oxidation.
Phenol (benzenol) has a distinct, characteristic odor and is moderately soluble in water while being readily soluble in organic solvents.

Phenol (benzenol) is a fundamental industrial chemical widely used as a precursor in the production of resins, plastics, pharmaceuticals, disinfectants, and numerous specialty chemical intermediates.
Phenol (benzenol) is used as a general disinfectant, as a reagent in chemical analysis and for the manufacture of artificial resins, medical and industrial organic compounds and dyes.

Phenol (benzenol) is also used in the manufacture of fertilisers, explosives, paints and paint removers, drugs, pharmaceuticals, textiles and coke.
Phenol (benzenol) is produced in large volume, mostly as an intermediate in the production of other chemicals.

Phenol (benzenol) is a white crystalline (at room temperature), odorous and toxic chemical compound, which is used widely as a raw material in the manufacture of other chemical products.

Phenol (benzenol) is an aromatic organic compound with the molecular formula C6H5OH.
Phenol (benzenol) is a white crystalline solid that is volatile and can catch fire.

The molecule consists of a phenyl group (−C6H5) bonded to a hydroxy group (−OH).
Mildly acidic, Phenol (benzenol) requires careful handling because it can cause chemical burns.
Phenol (benzenol) is acutely toxic and is considered a health hazard.

Phenol (benzenol) was first extracted from coal tar, but today is produced on a large scale (about 7 million tonnes a year) from petroleum-derived feedstocks.
Phenol (benzenol) is an important industrial commodity as a precursor to many materials and useful compounds, and is a liquid when manufactured.

Phenol (benzenol) is primarily used to synthesize plastics and related materials.
Phenol (benzenol) and its chemical derivatives are essential for production of polycarbonates, epoxies, explosives such as picric acid, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical drugs.[10]

Phenol (benzenol) is used as a precursor for cyclohexanone, plastics, nonionic detergents and pharmaceutical drugs like aspirin.
Phenol (benzenol) acts as an anesthetic in chloraseptic.

Phenol (benzenol) reacts with acetone to get bisPhenol (benzenol)-A which is used in the synthesis of poly carbonates and epoxide resins.
Phenol (benzenol) is also used in the manufacture of synthetic resins, dyes, pharmaceuticals, synthetic tanning agents, perfumes, lubricating oils and solvents.

In molecular biology, Phenol (benzenol) is used in the extraction of nucleic acid from tissues by using the liquid/liquid Phenol (benzenol)-chloroform extraction technique.
Phenol (benzenol) is an active component of paint strippers which are used for the removal of epoxy and polyurethane.

Phenol (benzenol) is also used in the preparation of cosmetics, hair colors and skin lightening preparations.
In the field of medicine, Phenol (benzenol)'s spray is useful in helping sore throat.

Phenol (benzenol) is defined as an aromatic organic compound which can be either naturally occurring or synthetically produced.
Phenol (benzenol) is a white crystalline, volatile solid that is widely used in various industries and is known for its strong influence on the odour and taste of water, even at low concentrations.

Uses of Phenol (Benzenol):
The primary use of Phenol (benzenol) is in the production of Phenol (benzenol)ic resins, which are used in the plywood, construction, automotive, and appliance industries.
Other uses of Phenol (benzenol) include as a slimicide, as a disinfectant, and in medicinal products such as ear and nose drops, throat lozenges, and mouthwashes.

Phenol (benzenol) is used in organic synthesis and as a disinfectant.
Phenol (benzenol) is used mainly as an intermediate for chemicals and resins.

Phenol (benzenol) is also used in cosmetics, medical preparations, non-agricultural biocides, adhesives, binders, impregnating agents, paints, lacquers, varnishes, solvents, flooring, hardeners, and insulating materials.
Phenol (benzenol) is used as a flavoring agent.
Phenol (benzenol)'s other uses include reagent in chemical analysis, in germicidal paints and slimicides, as a preservative for pharmaceutical injections, and in human and veterinary medicine.

Phenol (benzenol) is a reactive organic chemical which is used in a wide variety of chemical products vital to the economy of the world.
Phenol (benzenol) is used as starting material or produce as an intermediate in industry.

Plastics, explosive, picric acid and different drugs are made from Phenol (benzenol).
In dye industry Phenol (benzenol)s are widely used to make azo dyes.
As wood preservatives, Phenol (benzenol)s (like cresols) are also used.

Chemicals:
The major uses of Phenol (benzenol), consuming two thirds of its production, involve its conversion to precursors for plastics.
Condensation with acetone gives bisPhenol (benzenol) A, a key precursor to polycarbonates and epoxide resins.

Condensation of Phenol (benzenol), alkylPhenol (benzenol)s, or diPhenol (benzenol)s with formaldehyde gives Phenol (benzenol)ic resins, an example of which is Bakelite.
Partial hydrogenation of Phenol (benzenol) gives cyclohexanone a precursor to nylon.
Nonionic detergents are produced by alkylation of Phenol (benzenol) to give the alkylPhenol (benzenol)s, e.g., nonylPhenol (benzenol), which are then subjected to ethoxylation.

Phenol (benzenol) is also a versatile precursor to a large collection of drugs, most notably aspirin but also many herbicides and pharmaceutical drugs.
Phenol (benzenol) is a component in liquid–liquid Phenol (benzenol)–chloroform extraction technique used in molecular biology for obtaining nucleic acids from tissues or cell culture samples.
Depending on the pH of the solution either DNA or RNA can be extracted.

Phenol (benzenol) is so inexpensive that it also attracts many small-scale uses.
Phenol (benzenol) is a component of industrial paint strippers used in the aviation industry for the removal of epoxy, polyurethane and other chemically resistant coatings.

Topical anesthetic:
Concentrated liquid Phenol (benzenol) 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.
Phenol (benzenol) spray, with Phenol (benzenol) as the active ingredient, is used medically to treat sore throat.
Phenol (benzenol) is the active ingredient in some oral analgesics.

Concentrated Phenol (benzenol) liquids are used for permanent treatment of ingrown toe and finger nails, a procedure known as a chemical matrixectomy.
The procedure was first described by Otto Boll in 1945.

Nerve block:
Phenol (benzenol) is used as a chemical denervation agent in analgesia treatment, such as for spasticity, arthritis, or cancer pain.
Phenol (benzenol)'s effect on the nerve is to denature protein, diminish nerve fat and myelin content, and interrupt sensory transmission to the brain.

If successful, pain relief may last for weeks to two years.
Complications may include pain on injection, bleeding, or infection.

Clinical studies from 2023-25 reported that local injection of Phenol (benzenol) (1.5–3 ml of 6% Phenol (benzenol) in sterile water) at three to five sensory knee nerves was effective as a neurolytic treatment to relieve pain associated with chronic osteoarthritis.
The Phenol (benzenol) method may be used for people who did not experience pain relief from radiofrequency ablation of knee nerves.

Resin production:
Phenol (benzenol) is primarily used in the manufacture of Phenol (benzenol)-formaldehyde resins, including Bakelite and other thermosetting plastics.

BisPhenol (benzenol) A synthesis:
Phenol (benzenol) serves as a key raw material in the production of bisPhenol (benzenol) A (BPA), which is used to manufacture polycarbonate plastics and epoxy resins.

Caprolactam production:
Phenol (benzenol) is used as an intermediate in the synthesis of caprolactam, the precursor for nylon-6.

Disinfectants and antiseptics:
Phenol (benzenol) has antimicrobial properties and is used in certain disinfectant formulations.

Pharmaceutical intermediates:
Phenol (benzenol) is utilized in the synthesis of drugs, including aspirin and other aromatic compounds.

Chemical intermediates:
Phenol (benzenol) functions as a building block in dyes, herbicides, plasticizers, and specialty chemical manufacturing.

Industry Uses:
Ion exchange agents
Abrasives
Chemical reaction regulator
Monomers
UV stabilizer
Solvents (which become part of product formulation or mixture)
Antioxidant
Adhesion/cohesion promoter
Other (specify)
Laboratory chemicals
Intermediates
Adhesives and sealant chemicals
Intermediate
Solvent
Fuel agents

Consumer Uses:
Monomers
Paint additives and coating additives not described by other categories
Abrasives
Not Known or Reasonably Ascertainable
Intermediate
Solvent
Intermediates
Adhesives and sealant chemicals
Other (specify)
Insulators

Properties of Phenol (Benzenol):
Phenol (benzenol) is an organic compound appreciably soluble in water, with about 84.2 g dissolving in 1000 ml (0.895 M).
Homogeneous mixtures of Phenol (benzenol) and water at Phenol (benzenol) to water mass ratios of ~2.6 and higher are possible.

The sodium salt of Phenol (benzenol), sodium phenoxide, is far more water-soluble.
Phenol (benzenol) is a combustible solid (NFPA rating = 2).

When heated, Phenol (benzenol) produces flammable vapors that are explosive at concentrations of 3 to 10% in air.
Carbon dioxide or dry chemical extinguishers should be used to fight Phenol (benzenol) fires.

Acidity:
Phenol (benzenol) is a weak acid, with a pH range of 5 to 6.

In aqueous solution in the pH range ca. 8–12 Phenol (benzenol) is in equilibrium with the Phenol (benzenol)ate anion C6H5O− (also called phenoxide or carbolate):
C6H5OH ⇌ C6H5O− + H+

Phenol (benzenol) is more acidic than aliphatic alcohols.
Phenol (benzenol)'s enhanced acidity is attributed to resonance stabilization of Phenol (benzenol)ate anion.

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 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 pKa of the enol of acetone in water is 10.9, making Phenol (benzenol) only slightly less acidic than Phenol (benzenol) (pKa 10.0).
Thus, the greater number of resonance structures available to phenoxide compared to acetone enolate seems to contribute little to Phenol (benzenol)'s stabilization.
However, the situation changes when solvation effects are excluded.

Hydrogen bonding:
In carbon tetrachloride and in alkane solvents, Phenol (benzenol) hydrogen bonds with a wide range of Lewis bases such as pyridine, diethyl ether, and diethyl sulfide.
The enthalpies of adduct formation and the −OH IR frequency shifts accompanying adduct formation have been compiled.
Phenol (benzenol) is classified as a hard acid.

Tautomerism:
Phenol (benzenol) exhibits keto-enol tautomerism with its unstable keto tautomer cyclohexadienone, but the effect is nearly negligible.
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 (benzenol) therefore exists essentially entirely in the enol form.
4,4' Substituted cyclohexadienone can undergo a dienone–Phenol (benzenol) rearrangement in acid conditions and form stable 3,4‐disubstituted Phenol (benzenol).

For substituted Phenol (benzenol)s, several factors can favor the keto tautomer: (a) additional hydroxy groups (see resorcinol) (b) annulation as in the formation of naphthols, and (c) deprotonation to give the Phenol (benzenol)ate.[19]

Phenoxides are enolates stabilised by aromaticity.
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".[20]

Reactions of Phenol (Benzenol):
Phenol (benzenol) is highly reactive toward electrophilic aromatic substitution.
The enhanced nucleophilicity is attributed to donation pi electron density from O into the ring.
Many groups can be attached to the ring, via halogenation, acylation, sulfonation, and related processes.

Phenol (benzenol) is so strongly activated that bromination and chlorination lead readily to polysubstitution.
The reaction affords 2- and 4-substituted derivatives.

The regiochemistry of halogenation changes in strongly acidic solutions where PhOH2]+ predominates.
Phenol (benzenol) reacts with dilute nitric acid at room temperature to give a mixture of 2-nitroPhenol (benzenol) and 4-nitroPhenol (benzenol) while with concentrated nitric acid, additional nitro groups are introduced, e.g. to give 2,4,6-trinitroPhenol (benzenol).

Friedel Crafts alkylations of Phenol (benzenol) and its derivatives often proceed without catalysts.
Alkylating agents include alkyl halides, alkenes, and ketones.

Thus, adamantyl-1-bromide, dicyclopentadiene), and cyclohexanones give respectively 4-adamantylPhenol (benzenol), a bis(2-hydroxyphenyl) derivative, and a 4-cyclohexylPhenol (benzenol)s.
Alcohols and hydroperoxides alkylate Phenol (benzenol)s in the presence of solid acid catalysts (e.g. certain zeolite).
Cresols and cumyl Phenol (benzenol)s can be produced in that way.

Aqueous solutions of Phenol (benzenol) are weakly acidic and turn blue litmus slightly to red.
Phenol (benzenol) is neutralized by sodium hydroxide forming sodium phenate or Phenol (benzenol)ate, but being weaker than carbonic acid, it cannot be neutralized by sodium bicarbonate or sodium carbonate to liberate carbon dioxide.

C6H5OH + NaOH → C6H5ONa + H2O

When a mixture of Phenol (benzenol) and benzoyl chloride are shaken in presence of dilute sodium hydroxide solution, phenyl benzoate is formed.

This is an example of the Schotten–Baumann reaction:
C6H5COCl + HOC6H5 → C6H5CO2C6H5 + HCl

Phenol (benzenol) is reduced to benzene when it is distilled with zinc dust or when its vapour is passed over granules of zinc at 400 °C:
C6H5OH + Zn → C6H6 + ZnO

When Phenol (benzenol) is treated with diazomethane in the presence of boron trifluoride (BF3), anisole is obtained as the main product and nitrogen gas as a byproduct.

C6H5OH + CH2N2 → C6H5OCH3 + N2

Phenol (benzenol) and its derivatives react with neutral iron(III) chloride to give intensely violet colored solutions containing phenoxide complexes.
Phenol (benzenol) gives a positive result with the Ceric Ammonium Nitrate (CAN) test, and produces a dark brownish precipitate, contrary to standard aliphatic alcohols which typically give a pink or red color.[24]

Production of Phenol (Benzenol):
Because of Phenol (benzenol)'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, also called Hock process.

Phenol (benzenol) involves the partial oxidation of cumene (isopropylbenzene) via the Hock rearrangement:
Compared to most other processes, the cumene process uses mild conditions and inexpensive raw materials.
For the process to be economical, both Phenol (benzenol) 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.
Phenol (benzenol) is oxidized to a hydroperoxide, akin to the production of cumene hydroperoxide.

Via the Hock rearrangement, cyclohexylbenzene hydroperoxide cleaves to give Phenol (benzenol) and cyclohexanone.
Cyclohexanone is an important precursor to some nylons.

Oxidation of benzene, toluene, cyclohexylbenzene:

The direct oxidation of benzene (C6H6) to Phenol (benzenol) is possible, but it has not been commercialized:
C6H6 + O → C6H5OH

Nitrous oxide 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 employing alternating current gives Phenol (benzenol) from benzene.

The oxidation of toluene 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.
Autoxidation of cyclohexylbenzene gives the hydroperoxide.
Decomposition of this hydroperoxide affords cyclohexanone and Phenol (benzenol).

Older methods:
Early methods relied on extraction of Phenol (benzenol) from coal derivatives or the hydrolysis of benzene derivatives.

Hydrolysis of benzenesulfonic acid:
The original commercial route was developed by Bayer and Monsanto in the early 1900s, based on discoveries by Wurtz and Kekulé.
The method involves the reaction of a strong base with benzenesulfonic acid, proceeded by the reaction of hydroxide with sodium benzenesulfonate to give sodium phenoxide.
Acidification of the latter gives Phenol (benzenol).

The net conversion is:
C6H5SO3H + 2 NaOH → C6H5OH + Na2SO3 + H2O

Hydrolysis of chlorobenzene:

Chlorobenzene can be hydrolyzed to Phenol (benzenol) using a base (Dow process) 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 byproduct.

Coal pyrolysis:
Phenol (benzenol) is also a recoverable byproduct of coal pyrolysis.
In the Lummus process, the oxidation of toluene to benzoic acid is conducted separately.

Miscellaneous methods:
Phenyldiazonium salts hydrolyze to Phenol (benzenol).
The method is of no commercial interest since the precursor is expensive.

C6H5NH2 + HCl + NaNO2 → C6H5OH + N2 + H2O + NaCl

Salicylic acid decarboxylates to Phenol (benzenol).

Shipping:
Phenol (benzenol), which is produced and hence transported in large volumes, is shipped in a molten state below 70 °C (158 °F).
The melting point is lowered and corrosive nature enhanced in the presence of small amounts of water.
Typically, stainless steel containers and nitrogen-blanketing are required to prevent discoloration.

History of Phenol (Benzenol):
Phenol (benzenol) was discovered in 1834 by Friedlieb Ferdinand Runge, who extracted it (in impure form) from coal tar.
Runge called Phenol (benzenol) "Karbolsäure" (coal-oil-acid, carbolic acid).

Coal tar remained the primary source until the development of the petrochemical industry.
French chemist Auguste Laurent extracted Phenol (benzenol) in its pure form, as a derivative of benzene, in 1841.

In 1836, Auguste Laurent coined the name "phène" for benzene; this is the root of the word "Phenol (benzenol)" and "phenyl".
In 1843, French chemist Charles Gerhardt coined the name "phénol".

The antiseptic properties of Phenol (benzenol) were used by Sir Joseph Lister in his pioneering technique of antiseptic surgery.
Lister decided that the wounds had to be thoroughly cleaned.

He then covered the wounds with a piece of rag or lint covered in Phenol (benzenol).
The skin irritation caused by continual exposure to Phenol (benzenol) eventually led to the introduction of aseptic (germ-free) techniques in surgery.

Lister's work was inspired by the works and experiments of his contemporary Louis Pasteur in sterilizing various biological media.
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 sewage treatment using carbolic acid to reduce the smell of sewage cesspools.
Having heard of these developments, and having 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, he 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.
Phenol (benzenol) was a remarkable achievement

— Richard Hollingham, Blood and Guts: A History of Surgery, p. 63
Phenol (benzenol) 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.
In the tort law case of Roe v Minister of Health, Phenol (benzenol) was used to sterilize anaesthetic packed in ampoules, in which it contaminated the anaesthetic through invisible micro-cracks and caused paraplegia to the plaintiffs.

Second World War:
The toxic effect of Phenol (benzenol) on the central nervous system 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 (benzenol) were used as a means of individual execution by Nazi Germany during the Second World War.

Phenol (benzenol) was originally used by the Nazis in 1939 as part of the mass-murder of disabled people under Aktion T4.
The Germans learned that extermination of smaller groups was more economical by injection of each victim with Phenol (benzenol).

Phenol (benzenol) injections were given to thousands of people.
Maximilian Kolbe was also murdered with a Phenol (benzenol) injection after surviving two weeks of dehydration and starvation in Auschwitz when he volunteered to die in place of a stranger.
Approximately one gram is sufficient to cause death.

Occurrences of Phenol (Benzenol):
Phenol (benzenol) is a normal metabolic product, excreted in quantities up to 40 mg/L in human urine.
The temporal gland secretion of male elephants showed the presence of Phenol (benzenol) and 4-methylPhenol (benzenol) during musth.

Phenol (benzenol) is also one of the chemical compounds found in castoreum.
Phenol (benzenol) is ingested from the plants the beaver eats.

Phenol (benzenol) is a measurable component in the aroma and taste of the distinctive Islay scotch whisky generally ~30 ppm, but it can be over 160 ppm in the malted barley used to produce whisky.
This amount is different from and presumably higher than the amount in the distillate.

Biodegradation of Phenol (Benzenol):
Cryptanaerobacter Phenol (benzenol)icus is a bacterium species that produces benzoate from Phenol (benzenol) via 4-hydroxybenzoate.
Rhodococcus Phenol (benzenol)icus is a bacterium species able to degrade Phenol (benzenol) as sole carbon source.

Stability and Reactivity of Phenol (Benzenol):

Chemical Stability:
Remaining stable under normal ambient temperatures and recommended storage conditions.
Undergoing slow oxidation upon exposure to air and light, leading to possible discoloration.

Reactivity:
Exhibiting moderate reactivity due to the activated aromatic ring and hydroxyl group.
Reacting readily with strong oxidizing agents, strong bases, and certain halogenating agents.

Conditions to Avoid:
Avoiding excessive heat.
Avoiding open flames.

Avoiding direct sunlight.
Avoiding prolonged exposure to air.
Preventing contact with incompatible reactive chemicals.

Incompatible Materials:
Avoiding strong oxidizing agents.
Avoiding strong acids.

Avoiding strong bases.
Avoiding acid chlorides.
Avoiding reactive metals.

Hazardous Decomposition Products:
Producing carbon monoxide (CO) during thermal decomposition or combustion.
Producing carbon dioxide (CO₂) during combustion.
Releasing irritating Phenol (benzenol)ic vapors when heated.

Handling and Storage of Phenol (Benzenol):

Safe Handling:
Handling in well-ventilated areas using appropriate protective equipment.
Avoiding inhalation of vapors.
Preventing skin and eye contact due to corrosive nature and dermal absorption risk.

Hygiene Measures:
Washing hands thoroughly after handling.
Avoiding eating, drinking, or smoking in work areas.
Removing contaminated clothing immediately.

Storage Requirements:
Storing in tightly sealed containers.
Keeping in a cool, dry, well-ventilated location.
Maintaining distance from heat and ignition sources.

Packaging Integrity:
Using corrosion-resistant containers such as stainless steel or compatible lined drums.

Shelf Stability:
Maintaining stability under recommended storage conditions.
Minimizing exposure to air and light to preventing oxidation.

First Aid Measures of Phenol (Benzenol):

Inhalation:
Moving the exposed person to fresh air immediately.
Seeking medical attention if respiratory irritation, dizziness, or breathing difficulty occurs.

Skin Contact:
Removing contaminated clothing immediately.
Rinsing affected skin with large amounts of water for at least 15 minutes.
Seeking urgent medical attention due to systemic absorption risk.

Eye Contact:
Rinsing cautiously with water for at least 15 minutes while holding eyelids open.
Seeking immediate medical attention.

Ingestion:
Rinsing mouth with water.
Avoiding induction of vomiting.
Seeking immediate medical attention due to potential toxicity.

Firefighting Measures of Phenol (Benzenol):

Flammability:
Being combustible and forming flammable mixtures at elevated temperatures.

Suitable Extinguishing Media:
Using water spray.
Using foam.

Using dry chemical powder.
Using carbon dioxide (CO₂) appropriate for surrounding materials.

Hazardous Combustion Products:
Generating carbon oxides during combustion.
Releasing toxic Phenol (benzenol)ic fumes.

Special Protective Equipment for Firefighters:
Wearing self-contained breathing apparatus.
Wearing full protective clothing.

Specific Hazards:
Producing irritating and toxic vapors.
Preventing contaminated runoff from entering drains.

Accidental Release Measures of Phenol (Benzenol):

Personal Precautions:
Evacuating non-essential personnel.
Avoiding skin contact and inhalation.
Wearing appropriate protective equipment including gloves and respiratory protection.

Environmental Precautions:
Preventing release into drains, soil, or waterways due to aquatic toxicity.

Cleanup Methods:
Absorbing spills with inert materials such as sand or vermiculite.
Collecting into appropriate containers for regulated disposal.
Washing contaminated area thoroughly after material removal.

Additional Advice:
Ventilating the area adequately.
Avoiding vapor generation.
Disposing of waste according to hazardous waste regulations.

Exposure Controls / Personal Protective Equipment of Phenol (Benzenol):

Engineering Controls:
Using local exhaust ventilation and closed systems to minimizing vapor exposure.
Maintaining airborne concentrations below occupational exposure limits.

Respiratory Protection:
Using appropriate organic vapor respirators when ventilation is insufficient.

Hand Protection:
Wearing chemical-resistant gloves such as nitrile, neoprene, or butyl rubber.

Eye Protection:
Wearing chemical splash goggles and face shield when necessary.

Skin and Body Protection:
Wearing protective clothing resistant to chemical penetration.

Environmental Exposure Controls:
Implementing containment and proper waste management systems to preventing environmental contamination.

Identifiers of Phenol (Benzenol):
Linear Formula: C6H5OH
CAS Number: 108-95-2
Molecular Weight: 94.11
FEMA Number: 3223
Council of Europe no.: 11811
UNSPSC Code: 12164502
PubChem Substance ID: 24901564
Flavis number: 4.041
EC Number: 203-632-7
NACRES: NA.21
MDL number: MFCD00002143
Beilstein/REAXYS Number: 969616
Organoleptic: Phenol (benzenol)ic
Grade: Halal, Kosher
Biological source: synthetic
Agency: meets purity specifications of JECFA

CAS: 108-95-2
IUPAC Name: Phenol (benzenol)
Molecular Formula: C6H6O
InChI Key: ISWSIDIOOBJBQZ-UHFFFAOYSA-N
SMILES: OC1=CC=CC=C1
Molecular Weight (g/mol): 94.11

CAS Number: 108-95-2
ChEBI: CHEBI:15882
ChEMBL: ChEMBL14060
ChemSpider: 971
DrugBank: DB03255
ECHA InfoCard: 100.003.303
KEGG: D00033
PubChem CID: 996
RTECS number: SJ3325000
UNII: 339NCG44TV

UN number:
2821 (solution)
2312 (molten)
1671 (solid)

CompTox Dashboard (EPA): DTXSID5021124
InChI: InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
Key: ISWSIDIOOBJBQZ-UHFFFAOYSA-N
InChI=1/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
SMILES: Oc1ccccc1

Properties of Phenol (Benzenol):
Chemical formula: C6H6O
Molar mass: 94.113 g/mol
Appearance: Transparent crystalline solid
Odor: Sweet and tarry
Density: 1.07 g/cm3
Melting point: 40.5 °C (104.9 °F; 313.6 K)
Boiling point: 181.7 °C (359.1 °F; 454.8 K)
Solubility in water: 8.3 g/100mL (20 °C)
log P: 1.48
Vapor pressure: 0.4 mmHg (20 °C)
Acidity (pKa): 
9.95 (in water),
18.0 (in DMSO),
29.1 (in acetonitrile)
Conjugate base: Phenoxide
UV-vis (λmax): 270.75 nm
Dipole moment: 1.224 D

SMILES string: Oc1ccccc1
InChI: 1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
InChI key: ISWSIDIOOBJBQZ-UHFFFAOYSA-N
biological source: synthetic
grade: Halal, Kosher
agency: meets purity specifications of JECFA
vapor density: 3.24 (vs air)
vapor pressure: 0.09 psi ( 55 °C), 0.36 mmHg ( 20 °C)
assay: ≥99%
autoignition temp.: 1319 °F
may contain: ≤0.15% hypophosphorous acid as additive
expl. lim.: 8.6 %
Quality Level: 300, 400
Gene Information: human ... GABRA1(2554)
density: 1.071 g/mL at 25 °C (lit.)
application(s): flavors and fragrances
food allergen: no known allergens
organoleptic: Phenol (benzenol)ic

Appearance: white crystals (est)
Assay: 99.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity: 1.07100 @ 25.00 °C.
Melting Point: 38.00 to 41.00 °C. @ 760.00 mm Hg
Boiling Point: 181.00 to 182.00 °C. @ 760.00 mm Hg
Boiling Point: 104.00 to 105.00 °C. @ 50.00 mm Hg
Vapor Pressure: 0.614000 mmHg @ 25.00 °C. (est)
Flash Point: 175.00 °F. TCC ( 79.44 °C. )
logP (o/w): 1.460

Molecular Weight: 94.11 g/mol
XLogP3: 1.5
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 0
Exact Mass: 94.041864811 Da
Monoisotopic Mass: 94.041864811 Da
Topological Polar Surface Area: 20.2 Ų
Heavy Atom Count: 7
Complexity: 46.1
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of Phenol (Benzenol):
Assay (Iodometric Titration): ≥99.0%
Appearance (Color): Colorless
Form: Cryslals or crystalline solid
Comment: May become pink on exposure to air
Freezing Point: Not below 40.5°C (dry basis)
Water Content (Karl Fischer Titration): ≤0.5%
Residue on Evaporation: ≤0.05%

Pharmacology of Phenol (Benzenol):

ATC code:
C05BB05
D08AE03
N01BX03
R02AA19

Related Compounds of Phenol (Benzenol):
ThioPhenol (benzenol)
Benzeneselenol
Benzenetellurol
Sodium phenoxide

Names of Phenol (Benzenol):

Preferred IUPAC name:
Phenol

Systematic IUPAC name:
Benzenol

Other names:
Carbolic acid
Phenolic acid
Phenylic acid
Hydroxybenzene
Phenic acid
Phenyl alcohol
Phenyl hydroxide