Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 billion kg/year) from petroleum-derived feedstocks.
Phenol is an important industrial commodity as a precursor to many materials and useful compounds.
In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (—OH) bonded directly to an aromatic hydrocarbon group.
CAS Number: 108-95-2
EINECS No. 203-632-7
Chemical formula: C6H6O
Molar mass: 94.113 g/mol
Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula C6H5OH.
Phenol is a white crystalline solid that is volatile.
The molecule consists of a phenyl group (−C6H5) bonded to a hydroxy group (−OH).
Mildly acidic, Phenol requires careful handling because it can cause chemical burns.
The simplest is phenol, C6H5OH.
Phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule.
Phenol is primarily used to synthesize plastics and related materials.
Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical drugs.
Phenols are both synthesized industrially and produced by plants and microorganisms.
Phenols are similar to alcohols but form stronger hydrogen bonds.
Thus, Phenols are more soluble in water than are alcohols and have higher boiling points.
Phenols occur either as colourless liquids or white solids at room temperature and may be highly toxic and caustic.
Phenols are widely used in household products and as intermediates for industrial synthesis.
For example, phenol itself is used (in low concentrations) as a disinfectant in household cleaners and in mouthwash.
Phenol may have been the first surgical antiseptic.
In 1865 the British surgeon Joseph Lister used phenol as an antiseptic to sterilize his operating field.
With phenol used in this manner, the mortality rate from surgical amputations fell from 45 to 15 percent in Lister’s ward.
Phenol is quite toxic, however, and concentrated solutions cause severe but painless burns of the skin and mucous membranes.
Less-toxic phenols, such as n-hexylresorcinol, have supplanted phenol itself in cough drops and other antiseptic applications.
Butylated hydroxytoluene (BHT) has a much lower toxicity and is a common antioxidant in foods.
In industry, phenol is used as a starting material to make plastics, explosives such as picric acid, and drugs such as aspirin.
The common phenol hydroquinone is the component of photographic developer that reduces exposed silver bromide crystals to black metallic silver.
Other substituted phenols are used in the dye industry to make intensely coloured azo dyes.
Mixtures of phenols (especially the cresols) are used as components in wood preservatives such as creosote.
Properties of Phenol:
Phenol is an organic compound appreciably 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, is far more water-soluble.
Phenol is a type of organic compound.
While toxic to consume on its own, Phenol’s available in tiny doses in many household products like mouthwash and spray cleaners.
In Phenols pure form, it may be colorless or white.
Phenol has a mildly sugary scent that might remind you of somewhere that’s sterile, such as a hospital room.
In limited quantities, Phenol’s available for several medical and health-related uses.
What is phenol used for?
Pure phenol is used in certain medical procedures and as an ingredient in numerous treatments and laboratory applications.
Phenol Injection:
Phenol can be injected into your muscles to treat a condition known as muscle spasticity.
This happens when your brain doesn’t communicate properly with your spinal cord and nerves.
Phenol causes your muscles to become tight.
Muscle spasticity can even interrupt your ability to walk or talk.
Phenol can be caused by conditions like Parkinson’s disease, cerebral palsy, or brain trauma.
A phenol injection helps limit the signals sent from your nerves to your muscles that cause contractions.
This allows you to move more easily and feel less discomfort.
This treatment is similar to getting a botulinum toxin A (Botox) shot.
But phenol tends to be more useful for large muscles.
Vaccine preservative:
Phenol is used as a preservative in at least four vaccines.
Phenol helps keep bacteria from growing in and contaminating the vaccine solutions.
Phenol spray is safe to use at the recommend dose for a short time.
But using too much or giving it to children younger than 3-years old can be unsafe.
Read the ingredients label carefully to make sure you’re not allergic to any other components of the spray.
And if your sore throat is accompanied by a fever, nausea, and vomiting, see a doctor as soon as possible before using phenol for throat soreness.
Oral analgesics:
Many phenol-based products that help relieve pain or irritation in or around your mouth can also be bought over-the-counter to numb tissues in the mouth and lips.
These products are used as a short-term treatment for the symptoms of pharyngitis.
This happens when your throat gets inflamed from a bacterial or viral infection.
Phenol-based products for mouth and throat pain are widely available and safe to use in small doses.
But throat sprays and antiseptic liquids shouldn’t be used for more than a couple days at a time.
And if you’re having symptoms like fever and vomiting, see a doctor.
Phenol derivatives:
Phenol-derived compounds have a variety of uses, including:
Chemical peels:
Phenol in trichloroacetic acid is used to penetrate through layers of skin to get rid of old or damaged skin.
Food and cosmetic preservatives.
Phenol derivative butylated hydroxytoluene (BHT) is a common FDA-approved preservative used in cosmetics and to keep food from going bad.
Phenol’s safe to consume in small amounts.
But some companies have removed BHT from their foods in response to public pressure.
Phenol liquid:
Phenol liquid is often used in molecular biology with trichloromethane and chloroform to separate RNA, DNA, or proteins, and isolate them in the pure form.
This process is known as liquid-liquid extraction.
Phenol’s done by adding an equal amount of phenol and chloroform to a solution of cells or tissues.
The phenol-chloroform mixture separates molecules based on how soluble the tissue sample is in that solution.
The pH level of phenol helps separate the DNA and RNA.
Soap and antiseptic:
Soap containing phenol-based compounds is often called carbolic soap.
Phenol’s been used as an antiseptic during surgery since at least 1867.
Phenol was also a common fixture in state schools in England and Scotland until the 1980s.
Phenol’s remembered by millions in the United Kingdom for its distinct smell and red streaks it left on bathroom sinks.
Carbolic soap is still widely used throughout the world.
Phenol’s also a common tool used to assist countries who receive foreign aid from organizations like the Red Cross or Doctors Without Borders.
Phenol provides effective, low-cost hygiene to poverty-stricken communities.
Over time, pure phenol has been replaced by some of its derivatives as an antiseptic.
One derivative is n-hexylresorcinol, which can be found in cough drops.
Phenol, butylated hydroxytoluene (BHT), replaced phenol as a food antioxidant.
CAS No: 108-95-2
Japan, Chemical Substances Control Law METI-No.: 3-481
Formula: C6H5OH
Molecular Weight: 94
Appearance: Colorless or white solid
Melting Point (℃): 41
Boiling Point (℃): 182
Specific Gravity: 1.07
Flash Point (℃): 79
Autoignition Temperature (℃): 715
Flammability Range (%): 1.8～8.6
Solubility parameter: 14.5
Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical drugs.
KEYWORDS:
108-95-2, 203-632-7, CHEMBL14060, 339NCG44TV,DTXSID5021124, CHEBI:15882, Hydroxybenzene solution, Phenol solid, NCGC00091454-04, Phenol solutions
Acidity of Phenol:
Phenol is a weak acid.
In aqueous solution in the pH range ca. 8 - 12 it is in equilibrium with the phenolate anion C6H5O− (also called phenoxide):
C6H5OH ⇌ C6H5O− + H+
Phenol is more acidic than aliphatic alcohols.
The differing pKa is attributed to resonance stabilization of the phenoxide 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 it only slightly less acidic than phenol (pKa 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 1⁄3 of the increased acidity of phenol is attributable to inductive effects, with resonance accounting for the remaining difference.
Hydrogen bonding:
In carbon tetrachloride and alkane solvents phenol 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 studied.
Phenol is classified as a hard acid which is compatible with the C/E ratio of the ECW model with EA = 2.27 and CA = 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 with a nucleophilicity comparable to the one of carbanions or tertiary amines.
Phenol can react at both its oxygen or carbon sites as an ambident nucleophile (see HSAB theory).
Generally, oxygen attack of phenoxide anions is kinetically favored, while carbon-attack is thermodynamically preferred.
Mixed oxygen/carbon attack and by this a loss of selectivity is usually observed if the reaction rate reaches diffusion control.
Phenols have unique properties and are not classified as alcohols.
They have higher acidities due to the aromatic ring's tight coupling with the oxygen and a relatively loose bond between the oxygen and hydrogen.
This chapter opens up with the discussion of general conditions for separation of phenols and dowtherm impurities.
Phenol discusses gas chromatography separation of derivatized phenols and dihydroxybenzenes.
The peaks are very intense in phenol, methylphenol, and dimethylphenol, as would be predicted for aromatic compounds.
The regioisomers of dimethylphenol cannot be determined using only mass spectrometry.
Differentiating these regioisomers in a GC/MS analysis may be possible using retention indices.
An important point about the mass spectra of substituted phenols is the ortho effect.
When the position of certain substituents is ortho to a group with labile hydrogen, a rearrangement fragmentation will occur with the loss of a molecule and the formation of an odd-electron ion.
The study compares the mass spectra of 2,6-dichlorophenol and 4,5-dichlorophenol.
Applications of Phenol:
Phenol is used as a raw material to make phenolic resins and bisphenol A which in turn is a raw material for epoxy resins.
Phenol is also used as a raw material for a variety of dyes, surfactants, disinfectants, agricultural chemicals, pharmaceuticals, and intermediate chemicals.
Tautomerism:
Phenol exhibits 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 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".
Phenol is highly reactive toward electrophilic aromatic substitution.
The enhance 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'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.
Aqueous solutions of phenol are weakly acidic and turn blue litmus slightly to red.
Phenol is neutralized by sodium hydroxide forming sodium phenate or phenolate, 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 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 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 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
When phenol reacts with iron(III) chloride solution, an intense violet-purple solution is formed.
Phenols are compounds that possess a hydroxyl group directly attached to an aromatic carbocyclic nucleus.
Phenol is the trivial name for monohydroxybenzene.
The o-, m-, and p-cresols are monohydroxytoluenes (CH3.C6H4OH) and are distinct in their properties and reactions from the isomeric side-chain hydroxy compound, benzyl alcohol (C6H5.CH2OH), which is a typical aromatic alcohol.
Simple monohydric phenols are either corrosive liquids or low melting solids.
The dihydric and trihydric phenols are solids.
The mono-hydroxy compounds are only slightly soluble in water but are miscible with organic solvents.
Water solubility increases and solubility in organic solvents decreases with the introduction of additional hydroxyl groups.
They are all characterized by, and distinguished from, the aliphatic or aromatic alcohols by their ready solubility in aqueous alkali.
Phenols and the cresols are widely used as antiseptics and disinfectants; the cresols are contained in the wood preserving fluid, creosote.
Many phenols have wide application in the industrial production of plastics, dyestuffs, insectides, selective weedkillers, and germicides.
Production of Phenol:
Because of phenol's commercial importance, many methods have been developed for its production, but the cumene process is the dominant technology.
Uses of Phenol:
The primary use of phenol is in the production of phenolic resins, which are used in the plywood, construction, automotive, and appliance industries.
Phenol is also used in the production of caprolactam and bisphenol A, which are intermediates in the manufacture of nylon and epoxy resins, respectively.
Other uses of phenol include as a slimicide, as a disinfectant, and in medicinal products such as ear and nose drops, throat lozenges, and mouthwashes.
Sources and Potential Exposure:
Individuals may be exposed to phenol through breathing contaminated air or through skin contact in the workplace.
Other exposures to phenol may occur through the use of phenol-containing medicinal products (including mouthwashes, toothache drops, throat lozenges, analgesic rubs, and antiseptic lotions) or smoking tobacco.
Assessing Personal Exposure:
Phenol can be detected in urine; this test can be used to determine whether a person has recently been exposed to phenol or to substances that are changed to phenol in the body.
However, no test will tell whether a person has been exposed only to phenol, because many substances are changed to phenol in the body.
Properties of Phenol:
Phenols are more acidic than typical alcohols.
The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).
Deprotonation of a phenol forms a corresponding negative phenolate ion or phenoxide ion, and the corresponding salts are called phenolates or phenoxides.
Condensation with aldehydes and ketones
Phenols are susceptible to Electrophilic aromatic substitutions.
Condensation with formaldehyde gives resinous materials, famously Bakelite.
Another industrial-scale electrophilic aromatic substitution is the production of bisphenol A, which is produced by the condensation with acetone.
C-Alkylation with alkenes:
Phenol is readily alkylated at the ortho positions using alkenes in the presence of a Lewis acid such as aluminium phenoxide:
CH2=CR2 + C6H5OH → R2CHCH2-2-C6H4OH
More than 100,000 tons of tert-butyl phenols are produced annually (year: 2000) in this way, using isobutylene (CH2=CMe2) as the alkylating agent.
Especially important is 2,6-ditert-butylphenol, a versatile antioxidant.
Other reactions of Phenol:
Phenols undergo esterification.
Phenol esters are active esters, being prone to hydrolysis.
Phenols are reactive species toward oxidation.
Oxidative cleavage, for instance cleavage of 1,2-dihydroxybenzene to the monomethylester of 2,4 hexadienedioic acid with oxygen, copper chloride in pyridine Oxidative de-aromatization to quinones also known as the Teuber reaction and oxone.
In reaction depicted below 3,4,5-trimethylphenol reacts with singlet oxygen generated from oxone/sodium carbonate in an acetonitrile/water mixture to a para-peroxyquinole.
This hydroperoxide is reduced to the quinole with sodium thiosulfate.
Phenols are oxidized to hydroquinones in the Elbs persulfate oxidation.
Reaction of naphtols and hydrazines and sodium bisulfite in the Bucherer carbazole synthesis.
Phenol is an aromatic hydrocarbon compound composed of a benzene ring with a hydroxyl group.
Phenol is used as a raw material to make phenolic resins, bisphenol A for epoxy resins, and various pharmaceuticals.
CAS: No. 108-95-2
EINECS: No. 203-632-7
Natural sources of phenols:
Phenols are common in nature; examples include tyrosine, one of the standard amino acids found in most proteins; epinephrine (adrenaline), a stimulant hormone produced by the adrenal medulla; serotonin, a neurotransmitter in the brain; and urushiol, an irritant secreted by poison ivy to prevent animals from eating its leaves.
Many of the more complex phenols used as flavourings and aromas are obtained from essential oils of plants.
For example, vanillin, the principal flavouring in vanilla, is isolated from vanilla beans, and methyl salicylate, which has a characteristic minty taste and odour, is isolated from wintergreen.
Other phenols obtained from plants include thymol, isolated from thyme, and eugenol, isolated from cloves.
Phenol, the cresols (methylphenols), and other simple alkylated phenols can be obtained from the distillation of coal tar or crude petroleum.
Nomenclature of phenols:
Many phenolic compounds were discovered and used long before chemists were able to determine their structures.
Therefore, trivial names (i.e., vanillin, salicylic acid, pyrocatechol, resorcinol, cresol, hydroquinone, and eugenol) are often used for the most common phenolic compounds.
Physical properties of phenols:
Similar to alcohols, phenols have hydroxyl groups that can participate in intermolecular hydrogen bonding; in fact, phenols tend to form stronger hydrogen bonds than alcohols.
Hydrogen bonding results in higher melting points and much higher boiling points for phenols than for hydrocarbons with similar molecular weights.
For example, phenol (molecular weight [MW] 94, boiling point [bp] 182 °C [359.6 °F]) has a boiling point more than 70 degrees higher than that of toluene (C6H5CH3; MW 92, bp 111 °C [231.8 °F]).
Formation of phenol-formaldehyde resins:
Phenolic resins account for a large portion of phenol production.
Under the trade name Bakelite, a phenol-formaldehyde resin was one of the earliest plastics, invented by American industrial chemist Leo Baekeland and patented in 1909.
Phenol-formaldehyde resins are inexpensive, heat-resistant, and waterproof, though somewhat brittle.
The polymerization of phenol with formaldehyde involves electrophilic aromatic substitution at the ortho and para positions of phenol (probably somewhat randomly), followed by cross-linking of the polymeric chains.
Health benefits of Phenol:
Despite Phenols toxicity in its pure form, phenol has been shown to have numerous health benefits.
Antioxidants:
Plant-based compounds containing phenol are known to be antioxidants.
This means that they can stop the reaction of free radicals with other molecules in your body, preventing damage to your DNA as well as long-term health effects.
Free radicals are molecules that have lost an electron and become unstable.
This makes them prone to react with and damage molecules like DNA.
Free radicals sometimes cause the molecules they react with to create even more free radicals
Antioxidant molecules are like a barrier between free radicals and healthy molecules: antioxidants replace the missing electron and render it harmless.
Some notable phenolic antioxidants with proven health effects include:
-bioflavonoids, found in wines, teas, fruits, and vegetables
-tocopherols, including vitamin E, found in many fruits, nuts, and vegetables
-resveratrol, found in fruits, nuts, and red wine
-oregano oil, composed of many beneficial phenols like carvacrol, cymene, terpinine, and thymol
Cancer prevention:
Phenol-based compounds have been found to have some cancer prevention properties.
A 2010 animal review in Advances in Experimental Medicine and Biology suggested that getting phenols from a diet heavy in plants containing phenolic compounds and foods fortified with phenols helped strengthen the immune system and make cells more resistant to cancer throughout their life cycle.
Most of this research comes from animal models, but human studies are also promising.
According to a 2014 paper in Current Pharmaceutical Biotechnology, the complex structures of phenolic compounds can help make cancer cells more receptive to chemotherapy treatments.
Phenol is derived from benzene and propylene.
These raw materials are first used to produce cumene, which is then oxidised to become cumene hydroperoxide, before being split into phenol and its co-product, acetone.
Phenol plays a major role in our everyday lives.
Plywood, window glazing, DVDs and CDs, computers, sports equipment, fibre glass boats, automotive parts and accessories, circuit boards and flat panel televisions are some of the many items that rely on this important raw material.
The largest single market for phenol is in the production of Bisphenol A (BPA), which is manufactured from phenol and acetone.
BPA is, in turn, used to manufacture polycarbonate (the largest and fastest growing use for BPA) and epoxy resins.
Both polycarbonate and epoxy resins are used in many different industries and in countless items which we encounter every day.
Phenol is a major component of phenolic adhesives used in wood products such as plywood and oriented strand board.
Phenol is also used to produce phenolic resins used in the moulding of heat-resistant components for household appliances, counter-top and flooring laminates, and foundry castings.
In addition, Phenol is a valuable intermediate in the manufacture of detergents, agricultural chemicals, medicines, plasticisers, and dyes.
When reacted with bromine, BPA forms the fire retardant tetrabromobisphenol A.
BPA is also used to manufacture engineering thermoplastics such as polysulfones and polyacrylates.
Risks:
Phenol may have its share of uses and health benefits, but it can also be toxic or cause long-term health effects if you’re exposed to it in high amounts.
Here a few tips to avoid exposure:
Be careful at work. Being exposed to phenol in industrial facilities may increase your risk of heart disease.
This may be partly due to exposure to many other industrial chemicals in addition to phenol.
Don’t eat anything that might contain phenol.
Consuming phenol in Phenols pure form can damage your esophagus, stomach, intestines, and other digestive organs.
Phenol can be fatal if you have enough of it at one time.
Don’t put Phenol on your skin.
Pure phenol can damage your skinif it makes direct contact.
This can include burns and blisters.
Don’t inhale Phenol.
Laboratory animals experienced breathing difficulties and twitching of muscles when they breathed in a lot of phenol for even a short period of time.
Phenol has also been shown to cause systemic organ damage in laboratory animals.
Don’t drink Phenol.
Consuming water containing a lot of phenol can make muscles spasm and affect your ability to walk.
Too much of Phenol can be fatal.
Takeaway:
Phenol has numerous health benefits and can be helpful to treat a few different conditions.
But Phenol can be dangerous and even deadly in high amounts.
Be careful in places that may contain high levels of phenol, such as industrial facilities.
Don’t eat or drink anything that may have been exposed to phenol or have uncontrolled amounts of phenol in it.
Synthesis of Phenol:
Many phenols of commercial interest are prepared by elaboration of phenol or cresols.
They are typically produced by the alkylation of benzene/toluene with propylene to form cumene then O2 is added with H2SO4 to form phenol (Hock process).
In addition to the reactions above, many other more specialized reactions produce phenols:
-rearrangement of esters in the Fries rearrangement
-rearrangement of N-phenylhydroxylamines in the Bamberger rearrangement
-dealkylation of phenolic ethers
-reduction of quinones
-replacement of an aromatic amine by an hydroxyl group with water and sodium bisulfide in the Bucherer reaction
-thermal decomposition of aryl diazonium salts, the salts are converted to phenol
-by the oxidation of aryl silanes—an aromatic variation of the Fleming-Tamao oxidation
-catalytic synthesis from aryl bromides and iodides using nitrous oxide
Cumene process:
Overview of the cumene process:
Accounting for 95% of production (2003) is the cumene process, also called Hock process.
Phenol involves the partial oxidation of cumene (isopropylbenzene) via the Hock rearrangement:
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.
Phenol is oxidized to a hydroperoxide, akin to the production of cumene hydroperoxide.
Via the Hock rearrangement, cyclohexylbenzene hydroperoxide cleaves to give phenol and cyclohexanone.
Cyclohexanone is an important precursor to some nylons.
Oxidation of benzene and toluene:
The direct oxidation of benzene to phenol is theoretically possible and of great interest, 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 from benzene.
The oxidation of toluene, as developed, 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 and Monsanto in the early 1900s, begins with the reaction of a strong base with benzenesulfonic acid.
The conversion is represented by this idealized equation:
C6H5SO3H + 2 NaOH → C6H5OH + Na2SO3 + H2O
Hydrolysis of chlorobenzene:
Chlorobenzene can be hydrolyzed to phenol using 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 by product.
Coal pyrolysis:
Phenol is also a recoverable byproduct of coal pyrolysis.
In the Lummus Process, the oxidation of toluene to benzoic acid is conducted separately.
CAS Number: 108-95-2
CHEBI: 15882
ChEMBL: ChEMBL14060
ChemSpider: 971
DrugBank: DB03255
ECHA InfoCard: 100.003.303
KEGG: D00033
PubChem CID: 996
RTECS number: SJ3325000
UNII: 339NCG44TV
CompTox Dashboard (EPA): DTXSID5021124
Uses of Phenol:
The major uses of phenol, consuming two thirds of its production, involve its conversion to precursors for plastics.
Condensation with acetone gives bisphenol-A, a key precursor to polycarbonates and epoxide resins.
Condensation of phenol, alkylphenols, or diphenols with formaldehyde gives phenolic resins, a famous example of which is Bakelite.
Partial hydrogenation of phenol gives cyclohexanone, a precursor to nylon.
Nonionic detergents are produced by alkylation of phenol to give the alkylphenols, e.g., nonylphenol, which are then subjected to ethoxylation.
Phenol is also a versatile precursor to a large collection of drugs, most notably aspirin but also many herbicides and pharmaceutical drugs.
Phenol is a component in liquid–liquid phenol–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.
Medical:
Phenol is widely used as an antiseptic.
Phenols use was pioneered by Joseph Lister (see History section).
From the early 1900s to the 1970s it was used in the production of carbolic soap.
Concentrated phenol liquids are commonly 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.
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.
Phenol 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 treat sore throat.
Phenol is the active ingredient in some oral analgesics such as Chloraseptic spray, TCP and Carmex.
Niche uses of Phenol:
Phenol is so inexpensive that it attracts many small-scale uses.
Phenol is a component of industrial paint strippers 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 including sunscreens, hair colorings, and skin lightening preparations.
However, due to safety concerns, phenol is banned from use in cosmetic products in the European Union and Canada.
General Information of Phenol:
Phenol, also known as carbolic acid, is an aromatic organic compound. Pure phenol is a white crystalline solid that is volatile.
Phenol is mildly acidic and requires careful handling due to its propensity to cause chemical burns.
Although similar to alcohols, phenols have unique distinguishing properties.
Unlike in alcohols where the hydroxyl group is bound to a saturated carbon atom, in phenols the hydroxyl group is attached to an unsaturated aromatic (alternating double and single bond) hydrocarbon ring such as benzene.
Consequently, phenols have greater acidity than alcohols due to stabilization of the conjugate base through resonance in the aromatic ring.
Industrial uses involve its conversion to plastics or related materials.
In research laboratories phenol, when suspended in chloroform, is commonly used in the extraction of DNA from biological samples.
The liquid-liquid extraction of aqueous samples are mixed with equal volumes of a phenol:chloroform solution.
After combining, the mixture is centrifuged and two immiscible phases form.
The less dense aqueous phase is on top, and the organic phase (phenol:chloroform) is on the bottom.
The proteins will partition into the lower organic phase while the nucleic acids (as well as other contaminants such as salts, sugars, etc.) remain in the upper aqueous phase.
If the mixture is acidic, DNA will precipitate into the organic phase while RNA remains in the aqueous phase due to DNA being more readily neutralized than RNA.
Health and Safety of Phenol:
Phenol and its vapors are corrosive to the eyes, skin, and respiratory tract.
The corrosive effect on skin and mucous membranes is due to a protein-degenerating effect.
Repeated or prolonged skin contact with phenol may cause dermatitis, and potentially second and third-degree burns. Inhalation of phenol vapor may cause lung edema.
Phenol may adversely effect the central nervous system and heart.
Long-term, or repeated exposure, to phenol may have harmful effects on the liver and kidneys.
While there is no evidence that phenol causes cancer in humans it is readily absorbed through the skin; 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.
Phenol is also a reproductive toxin causing increased risk of abortion and low birth weight indicating retarded development in utero.
Chemical burns from skin exposures can be decontaminated by washing with polyethylene glycol or isopropyl alcohol; flushing with copious amounts of water will help to remediate the burn.
Removal of contaminated clothing is required, as well as immediate hospital treatment for large splashes.
Personal Protective Equipment - The minimum lab attire should always be worn when conducting work with phenol: long pants, closed-toe shoes and protective eyewear (safety glasses or splash goggles).
A properly fitting lab coat and chemically resistant gloves should also be worn.
When only working with phenol a chloroprene glove will be appropriate, use of a thicker glove is recommended if larger volumes are used.
Unfortunately, chloroprene gloves do not provide sufficient protection against chloroform.
The best glove to use when conducting work with phenol-chloroform mixtures is a butyl/viton multilayered glove.
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/100 mL (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
History of Phenol:
Phenol was discovered in 1834 by Friedlieb Ferdinand Runge, who extracted it (in impure form) from coal tar.
Runge called phenol "Karbolsäure" (coal-oil-acid, carbolic acid).
Coal tar remained the primary source until the development of the petrochemical industry.
In 1841, the French chemist Auguste Laurent 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 1843, French chemist Charles Gerhardt coined the name "phénol".
The antiseptic properties of phenol were used by Sir Joseph Lister (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.
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.
Phenol was originally used by the Nazis in 1939 as part of the Aktion T4 euthanasia program.
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 was also killed with a phenol 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.
Molecular Weight: 94.11
XLogP3: 1.5
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 0
Exact Mass: 94.041864811
Monoisotopic Mass: 94.041864811
Topological Polar Surface Area: 20.2 Ų
Heavy Atom Count: 7
Formal Charge: 0
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
Occurrences of Phenol:
Phenol 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 and 4-methylphenol during musth.
Phenol is also one of the chemical compounds found in castoreum.
Phenol 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 used to produce 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 from phenol via 4-hydroxybenzoate.
Rhodococcus phenolicus is a bacterium species able to degrade phenol as sole carbon source.
Preferred IUPAC name:
Phenol
Systematic IUPAC name:
Benzenol
Other names
Carbolic acid
Phenylic acid
Hydroxybenzene
Phenic acid
About Phenol helpful information:
Phenol is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 1 000 000 to < 10 000 000 tonnes per annum.
Phenol is used by consumers, in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
Consumer Uses of Phenol:
ECHA has no public registered data indicating whether or in which chemical products Phenol might be used. ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
Article service life of Phenol:
Other release to the environment of Phenol is likely to occur from: outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials) and indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment).
Phenol can be found in complex articles, with no release intended: machinery, mechanical appliances, electrical/electronic products not covered by Waste Electrical and Electronic Equipment (WEEE) directive (e.g. large-scale stationary industrial tools) and machinery, mechanical appliances and electrical/electronic products (e.g. computers, cameras, lamps, refrigerators, washing machines).
Phenol can be found in products with material based on: leather (e.g. gloves, shoes, purses, furniture).
Widespread uses of Phenol by professional workers:
Phenol is used in the following products: fertilisers and polymers.
Phenol is used in the following areas: scientific research and development.
Phenol is used for the manufacture of: chemicals and plastic products. Other release to the environment of this substance is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.
Formulation or re-packing of Phenol:
Phenol is used in the following products: polymers, coating products, adhesives and sealants, fertilisers, laboratory chemicals, leather treatment products, air care products, anti-freeze products, biocides (e.g. disinfectants, pest control products), fillers, putties, plasters, modelling clay, non-metal-surface treatment products, lubricants and greases, plant protection products, pharmaceuticals, photo-chemicals, polishes and waxes, washing & cleaning products and welding & soldering products.
Release to the environment of Phenol can occur from industrial use: formulation of mixtures, in processing aids at industrial sites, formulation in materials and in the production of articles.
Uses at industrial sites of Phenol:
Phenol is used in the following products: polymers, coating products, photo-chemicals, laboratory chemicals, washing & cleaning products, fertilisers, pharmaceuticals and cosmetics and personal care products.
Phenol is used in the following areas: scientific research and development.
Phenol is used for the manufacture of: chemicals, plastic products and rubber products.
Release to the environment of Phenol can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates), in processing aids at industrial sites, for thermoplastic manufacture, as processing aid and in the production of articles.
Manufacture of Phenol:
Release to the environment of Phenol can occur from industrial use: manufacturing of the substance.
Phenol is produced from cumene in what is known as the four-stage Hock production process.
Phenol is is an essential starting material for a wide range of applications in the electrical/electronics, automotive, construction and household/furniture industries.
Phenol can be combined with formaldehyde to produce phenolic resins, which represent the second largest commercial use of phenol.
Phenolic resins are used in a wide range of applications, including plywood and oriented strand board, furniture, insulation materials, laminates, foundry molds and adhesives.
Another application for phenol is as the raw material for caprolactam and adipic acid for the production of nylon intermediates.
Major uses of Phenol include engineering thermoplastics and synthetic fibers for clothing and carpeting.
PHENOLS USES:
Phenol is an essential starting material for a wide range of applications in the electrical/electronics, automotive, construction and household/furniture industries.
Phenol can be combined with formaldehyde to produce phenolic resins, which represent the second largest commercial use of phenol.
Phenolic resins are used in a wide range of applications, including plywood and oriented strand board, furniture, insulation materials, laminates, foundry molds and adhesives.
Another application for phenol is as the raw material for caprolactam and adipic acid for the production of nylon intermediates.
Major uses include engineering thermoplastics and synthetic fibers for clothing and carpeting.
Toxicity of Phenol:
Phenol and its vapors are corrosive to the eyes, the skin, and the respiratory tract.
Phenols corrosive effect on skin and mucous membranes is due to a protein-degenerating effect.
Repeated or prolonged skin contact with phenol may cause dermatitis, or even second and third-degree burns.
Inhalation of phenol vapor may cause lung edema.
Phenol may cause harmful effects on the central nervous system and heart, resulting in dysrhythmia, seizures, and coma.
The kidneys may be affected as well.
Long-term or repeated exposure of the substance may have harmful effects on the liver and kidneys.
There is no evidence that phenol causes cancer in humans.
Besides its hydrophobic effects, another mechanism for the toxicity of phenol may be the formation of phenoxyl 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 LD50 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.
Chemical burns from 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 chloroform (a commonly used mixture in molecular biology for DNA and RNA purification).
Phenol is also a reproductive toxin causing increased risk of miscarriage and low birth weight indicating retarded development in utero.
Handling of Phenol:
Wear impervious clothing, including close-toed shoes, lab coat or apron and butyl rubber or neoprene gloves.
Avoid heat, flames and ignition sources.
Hot liquid phenol will attack aluminum, magnesium, lead and zinc metals.
Storage of Phenol:
Store phenol in a cool, dry, ventilated area away from sources of heat or ignition.
Store separately from reactive or combustible materials and out of direct sunlight.
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 compounds of which the phenol discussed in this article is the simplest member.
phenol
108-95-2
carbolic acid
Hydroxybenzene
Phenic acid
Oxybenzene
Phenylic acid
Benzenol
Phenylic alcohol
Monophenol
Phenyl hydrate
Phenyl hydroxide
PhOH
Monohydroxybenzene
Paoscle
Phenole
Izal
Phenol alcohol
Phenyl alcohol
Phenol, liquefied
Acide carbolique
Fenolo
Carbolsaure
Fenosmolin
Fenosmoline
Phenosmolin
Fenol
Liquid phenol
Carbolic oil
Phenol, pure
Phenol homopolymer
Fenolo [Italian]
Phenole [German]
Benzene, hydroxy-
Rcra waste number U188
Campho-Phenique Gel
Phenic
Carbolsaure [German]
Campho-Phenique Liquid
NCI-C50124
Liquefied phenol
Phenol, molten
Baker's P & S liquid & Ointment
Fenol [Dutch, Polish]
Baker's P and S Liquid and Ointment
Monohydroxy benzene
Phenol, sulfurated
Un 2812 (solution)
UN 2312 (molten)
Acide carbolique [French]
UN 1671 (solid)
NSC 36808
Campho-Phenique Cold Sore Gel
Anbesol
Phenic alcohol
Synthetic phenol
Liquified Phenol
Phenol, dimer
Carbolicum acidum
RCRA waste no. U188
UNII-339NCG44TV
MFCD00002143
UN1671
UN2312
UN2821
AI3-01814
CHEMBL14060
339NCG44TV
DTXSID5021124
CHEBI:15882
Phenol (or solutions with 5% or more phenol)
NSC-36808
Hydroxybenzene solution
Phenol, solid [UN1671] [Poison]
Phenol, molten [UN2312] [Poison]
NCGC00091454-04
Phenol solutions [UN2821] [Poison]
DSSTox_CID_1124
Phenol, >=99.0%
DSSTox_RID_75955
DSSTox_GSID_21124
27073-41-2
61788-41-8
Phenol [JAN]
Caswell No. 649
phenylalcohol
hydroxy benzene
Phenol 100 microg/mL in Methanol
Phenol, liquid
Phenol, solid
Baker's p and s
17442-59-0
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
Benzophenol
Carbolsaeure
Karbolsaeure
Extracts, coal tar oil alk.
acide phenique
Hydroxy-benzene
Phenol solution
Phenol liquid
Phenol molten
Phenol solutions
Phenol synthetic
Phenol,liquified
Phenolated water
Pandy's reagent
2-allphenol
Cepastat lozenges
Phenol, labeled with carbon-14
Phenol (liquid)
2-phenyl alcohol
Phenol, liquified
Phenol, synthetic
Phenol, ultrapure
Phenol ACS grade
EINECS 262-972-4
Liquefied phenol BP
Paoscle (TN)
Carbolic acid liquid
Phenol polymer-bound
Phenol (TN)
Phenol,(S)
Phenol, ACS reagent
Carbolic acid, liquid
1ai7
1li2
4i7l
Liquefied phenol (TN)
Phenol (JP17/USP)
Phenol, detached crystals
Phenol, >=99%
WLN: QR
Liquefied phenol (JP17)
bmse000290
bmse010026
C6H5OH
Fenol(DUTCH, POLISH)
EC 203-632-7
PHENOL, 80% in ethanol
Phenol, LR, >=99%
65996-83-0
MLS001065591
Phenol, for molecular biology
BIDD:ER0293
Phenol for disinfection (TN)
Phenol, natural, 97%, FG
Phenol, 90% aqueous solution
Cuticura pain relieving ointment
Phenol, AR, >=99.5%
BDBM26187
CHEBI:33853
Phenol for disinfection (JP17)
Phenolated water for disinfection
Salicylic acid related compound c
3f39
Phenol 10 microg/mL in Methanol
Phenol solution, 1.0 M in THF
ENT-1814
NSC36808
ZINC5133329
Phenol, Glass Distilled Under Argon
Tox21_113463
Tox21_201639
Tox21_300042
Phenol 5000 microg/mL in Methanol
phenol;phenol [jan];phenol, pure;phenol phenol [jan] phenol, pure
STL194294
AKOS000119025
Tox21_113463_1
DB03255
MCULE-9943948107
NA 2821
Phenol, BioXtra, >=99.5% (GC)
Phenol, SAJ first grade, >=98.0%
UN 1671
UN 2312
UN 2821
Phenol, BP grade 80% aqueous solution
NCGC00091454-01
NCGC00091454-02
NCGC00091454-03
NCGC00091454-05
NCGC00091454-06
NCGC00091454-07
NCGC00254019-01
NCGC00259188-01
Phenol solution, 1 M in dichloromethane
Phenol, JIS special grade, >=99.0%
63496-48-0
73607-76-8
AM802906
BP-30160
SMR000568492
Phenol, PESTANAL(R), analytical standard
Liquified Phenol (contains 7-10 % water)
FT-0645154
FT-0673707
FT-0693833
P1610
Phenol stock solution, 100 mg/dL, standard
C00146
D00033
Phenol, unstabilized, ReagentPlus(R), >=99%
Phenol, p.a., ACS reagent, 99.5-100.5%
Phenol, >=96.0% (calc. on dry substance, T)
Q130336
J-610001
Phenol, for molecular biology, ~90% (T), liquid
F1908-0106
Phenol, unstabilized, purified by redistillation, >=99%
Phenol, BioUltra, for molecular biology, >=99.5% (GC)
Phenol, United States Pharmacopeia (USP) Reference Standard
UNII-3JYG22FD73 component ISWSIDIOOBJBQZ-UHFFFAOYSA-N
Liquified Phenol, meets USP testing specifications, >=89.0%
Phenol, BioUltra, for molecular biology, TE-saturated, ~73% (T)
Phenol solution, 5000 mug/mL in methanol, certified reference material
Phenol solution, certified reference material, 500 mug/mL in methanol
Phenol, puriss. p.a., ACS reagent, reag. Ph. Eur., 99.0-100.5%
p-Hydroxy polystyrene (100-200 mesh, 0.5-1.5 mmol/g)@CRLFMFCD03703209
Phenol solution, 100 mug/mL in acetonitrile, PESTANAL(R), analytical standard
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 solution, BioReagent, Equilibrated with 10??mM Tris HCl, pH??8.0, 1??mM EDTA, for molecular biology
Phenol solution, BioReagent, Saturated with 0.1 M citrate buffer, pH??4.3 +/- 0.2, for molecular biology
Phenol, polymer-bound, 100-200 mesh, extent of labeling: 0.5-1.5 mmol/g loading, 1 % cross-linked with divinylbenzene
Phenol, puriss., meets analytical specification of Ph. Eur., BP, USP, >=99.5% (GC), crystalline (detached)
Regulatory process names:
carbolic acid
monohydroxybenzene
Phenol
Phenol
phenol
PHENOL SOLUTION
PHENOL, MOLTEN
PHENOL, SOLID
phenylalcohol
Translated names:
acid carbolic (ro)
fenil-alkohol (hr)
fenilalcohol (es)
fenilalcool (ro)
fenilalkohol (hu)
fenilalkohol (sl)
fenilalkoholis (lt)
fenilspirts (lv)
fenol (cs)
fenol (da)
fenol (es)
fenol (hr)
fenol (hu)
fenol (nl)
fenol (no)
Fenol (pl)
fenol (pt)
fenol (ro)
fenol (sk)
fenol (sl)
fenol (sv)
Fenoli (fi)
fenolis (lt)
fenolo (it)
fenols (lv)
fenool (et)
fenylalkohol (sk)
fenylalkohol (sv)
fenüülalkohol (et)
hidroxibenceno (es)
Hydroksybenzen (pl)
karbolhape (et)
karbolio rūgštis (lt)
karbolna kiselina (hr)
karbolna kislina (sl)
karbolová kyselina (cs)
karbolsav (hu)
karbolskābe (lv)
Karbolsäure (de)
kyselina karbolová (sk)
monohidroksibenzen (hr)
monohidroksibenzen (sl)
monohidroksibenzenas (lt)
monohidroksibenzols (lv)
monohidroxibenzen (ro)
monohidroxibenzeno (pt)
monohidroxibenzol (hu)
Monohydroxybenzene (de)
monohydroxybenzén (sk)
monohüdroksübenseen (et)
phenol (da)
Phenol (de)
Phenylalcohol (de)
phénol; acide carbolique; monohydroxybenzène; phényléthanol (fr)
ácido carbólico (es)
ácido carbólico (pt)
álcool fenílico (pt)
φαινόλh (el)
карболова киселина (bg)
монохидроксибензен (bg)
фенилалкохол (bg)
фенол (bg)
CAS names:
Phenol
IUPAC names:
acide carbolique
Benzenol
benzenol
carbolic acid
fenolo
Hydroxybenzene
hydroxybenzene
Hydroxybenzene, Carbolic acid
Monohydroxybenzene
monohydroxybenzene
PHENOL
Phenol
phenol
Phenol
phenol
Phenol - ML0107B
phenol carbolic acid monohydroxybenzene phenylalcohol
Phenol, pure
phenol, pure
phenolphenol
phenylalcohol
Public name for Phenol Pur F900B is phenol; public name for Phenol Tech F900A is diacetone alcohol
Trade names:
(Mono)hydroxybenzene
ACIDO CARBOLICO
Acido Carbolico
Acido fenico
Acido fenico - Idrossibenzene
Benzenol
Benzyl Alcohol
Carbolic acid
Carbolsaeure
Carbolsäure, Karbolsäure, Monohydroxybenzol,
Carbolsäure, Karbolsäure, Monohydroxybenzol, Phenylalkohol, Benzophenol
CARBOLZUUR HYDROXY BENZEEN
CARBONATE OLIGOMER OF TETRABROMOBISPHENOL A
fenol
fenolo
HIDROXIBENCENO
hydrate; phenylic acid; Fenolo (Italian)
Hydroxybenzene
hydroxybenzene
Hydroxybenzene; oxybenzene; phenic acid; phenyl
Hydroxybenzene; oxybenzene; phenic acid; phenyl hydrate; phenylic acid; Fenolo (Italian)
Hydroxybenzol,Benzophenol,Karbolsäure
Idrossido di fenile
Karbolsaeure
MONOHIDROXIBENCENO
Monohydroxybenzene
Monohydroxybenzol
Monoidrossibenzene
Oxybenzene
Phenic acid
phenic acid, carbolic acid, phenyl hydroxide,
phenic acid, carbolic acid, phenyl hydroxide, hydroxybenzene
PHENOL
Phenol
phenol
Phenol Pur F900A
Phenol Pur F900B
phenol synthetic, technical
Phenol Synthetical Technical, A type
PHENOL,CARBOLIC ACID, PHENYL HYDROXIDE
phenyl hydrate
phenyl hydroxide
Phenylalcohol
Phenylalkohol, Benzophenol
Phenylhydroxide
phenylic acid
phenylic alcohol
Phenylsaeure
PhOH
Other identifiers:
108-95-2
14534-23-7
14534-23-7
50356-25-7
50356-25-7
604-001-00-2
8002-07-1
8002-07-1