PHENYLIC HYDRATE
PHENYLIC HYDRATE
Phenylic hydrate is a white crystalline solid that is volatile, mildly acidic, and widely used in the production of plastics, synthetic resins, and pharmaceutical drugs like aspirin.
Phenylic hydrate is both a natural metabolite and an industrial chemical with applications ranging from antiseptics and disinfectants to the synthesis of polycarbonates and phenolic resins.
Phenylic hydrate is a versatile compound used in the manufacture of a wide range of products, including plastics, detergents, and pharmaceuticals, due to its role as a precursor in chemical synthesis.
CAS Number: 108-95-2
EC Number: 203-632-7
Chemical Formula: C6H5OH
Molar Mass: 94.11 g/mol
Synonyms: Hydroxybenzene, Carbolic acid, carbolic acid, hydroxybenzene, phenic acid, phenylic acid, oxybenzene, benzenol, phenyl hydrate, monophenol, phenyl hydroxide, phenylic alcohol, phenol, 108-95-2, carbolic acid, Hydroxybenzene, Phenic acid, Oxybenzene, Benzenol, Phenylic acid, Phenylic alcohol, Monophenol, Phenyl hydrate, Phenyl hydroxide, PhOH, Monohydroxybenzene, Paoscle, Phenole, Izal, Phenyl alcohol, Phenol alcohol, Acide carbolique, Phenol, liquefied, Fenolo, Carbolsaure, Phenosmolin, Fenol, Liquid phenol, Phenol, pure, Benzene, hydroxy-, Rcra waste number U188, Liquefied phenol, Liquified Phenol, Carbolicum acidum, NCI-C50124, Campho-Phenique Gel, phenylalcohol, UN 2312 (molten), Phenol [JAN], UN 1671 (solid), Phenic, Caswell No. 649, Campho-Phenique Liquid, Phenol, molten, 2-allphenol, Baker’s P & S liquid & Ointment, Fenol [Dutch, Polish], NSC 36808, Phenol, liquified, Baker’s P and S Liquid and Ointment, Monohydroxy benzene, CCRIS 504, Campho-Phenique Cold Sore Gel, Carbolsaeure, FEMA No. 3223, Karbolsaeure, HSDB 113, acide phenique, DTXSID5021124, Phenic alcohol, Phenol, liquified, Synthetic phenol, Phenol, dimer, AI3-01814, RCRA waste no. U188, EINECS 203-632-7, UNII-339NCG44TV, MFCD00002143, NSC-36808, UN1671, UN2312, UN2821, EPA Pesticide Chemical Code 064001, 339NCG44TV, CHEBI:15882, Phenol [USP:JAN], ENT-1814, Phenol-3,5-d2, 27073-41-2, CHEMBL14060, DTXCID501124, EC 203-632-7, NSC36808, Phenol, Glass Distilled Under Argon, 65996-83-0, Phenol, solid [UN1671], Phenol (USP:JAN), Phenol, molten [UN2312], NCGC00091454-04, Fenosmoline, Fenosmolin, PHENOL (IARC), PHENOL [IARC], PHENOL (USP-RS), PHENOL [USP-RS], PHENOL (II), PHENOL [II], PHENOL (MART.), PHENOL [MART.], Phenol, >=99.0%, 17442-59-0, PHENOL (EP MONOGRAPH), PHENOL [EP MONOGRAPH], PHENOL (USP MONOGRAPH), PHENOL [USP MONOGRAPH], Carbol, hydroxy benzene, Phenol 100 microg/mL in Methanol, Phenol, liquid, Phenol, solid, Baker’s p and s, Phenol, sulfurated, CAS-108-95-2, METACRESOL IMPURITY A (EP IMPURITY), METACRESOL IMPURITY A [EP IMPURITY], (14C)Phenol, HEXYLRESORCINOL IMPURITY A (EP IMPURITY), HEXYLRESORCINOL IMPURITY A [EP IMPURITY], PHENOL (2,3,4,5,6-D5), arenols, Benzophenol, Karbolsaure, Phylorinol, Ulcerease, Hydroxy-benzene, Phenol liquid, Phenol molten, Fungus Fighte, Phenol synthetic, Pandy’s reagent, Cepastat lozenges, Fortinia ID, Phenol, labeled with carbon-14, Acidum Carbolicum, Phenol (liquid), 2-phenyl alcohol, Sore ThroatCherry, Phenol, synthetic, Phenol, ultrapure, ABC Sore Throat, HEB Sore Throat, Phenol ACS grade, RugbyCherry Flavor, Sore ThroatMenthol, Sore Throat Spray, Meijer Sore Throat, Sore Throat Cherry, Sore Throat Relief, Liquefied phenol BP, Paoscle (TN), Topcare Sore Throat, Carbolic acid liquid, Phenol (TN), Phenol,(S), TopCareCherry Flavor, Phenol, ACS reagent, PUBLIX Sore Throat, Carbolic acid, liquid, CepastatExtra Strength, Walgreens Sore Throat, 63496-48-0, Sore Throat, Vortex Moisturizer Oral, 1ai7, 1li2, 4i7l, Liquefied phenol (TN), DRx Choice Sore Throat, PHENOL [VANDF], Wild Horse 777 Oral, PHENOL [FHFI], PHENOL [HSDB], PHENOL [INCI], Sore Throat ReliefCherry, Castellani Paint 1.5%, Phenol (JP17/USP), PHENOL [WHO-DD], Phenol, detached crystals, Pain RelievingPetro Carbo, PHENOL [MI], Phenol, >=99%, Sore Throat ReliefMenthol, WLN: QR, Good Neighbor Sore Throat, Liquefied phenol (JP17), bmse000290, bmse010026, C6H5OH, Fenol(DUTCH, POLISH), NICE SORE THROAT Cherry, PHENOL, 80% in ethanol, Phenol, LR, >=99%, Phen-2,4,6-d3-ol-d, HEB Sore ThroatCherry Flavor, MLS001065591, Phenol (CGA 73330), Phenol, for molecular biology, BIDD:ER0293, Phenol for disinfection (TN), ABC Sore ThroatMenthol Flavor, HEB Sore ThroatMenthol Flavor, NICE SORE THROAT Spearmint, Phenol, natural, 97%, FG, CHLORASEPTIC SORE THROAT, Chloraseptic Sore Throat Cherry, Chloraseptic Sore Throat Citrus, Cuticura pain relieving ointment, Sore Throat ReliefCherry Flavor, CARBOLICUM ACIDUM [HPUS], Phenol, AR, >=99.5%, PHENOL,LIQUIFIED [VANDF], BDBM26187, CHEBI:33853, Phenol for disinfection (JP17), Topcare Sore ThroatMenthol Flavor, 3f39, Phenol 10 microg/mL in Methanol, PUBLIX Sore ThroatMenthol Flavor, Walgreens Sore ThroatCherry Flavor, phenol 0.6% anesthetic oral rinse, Tox21_113463, Tox21_201639, Tox21_300042, DRx Choice Sore ThroatMenthol Flavor, Phenol 5000 microg/mL in Methanol, AKOS000119025, Eos Medicated Pain Relieving Lip Balm, Tox21_113463_1, DB03255, Good Neighbor Sore ThroatCherry Flavor, NA 2821, Phenol, BioXtra, >=99.5% (GC), Phenol, SAJ first grade, >=98.0%, UN 1671, UN 2312, UN 2821, USEPA/OPP Pesticide Code: 064001, NCGC00091454-01, NCGC00091454-02, NCGC00091454-03, NCGC00091454-05, NCGC00091454-06, NCGC00091454-07, NCGC00254019-01, NCGC00259188-01, Phenol, JIS special grade, >=99.0%, 61788-41-8, 73607-76-8, AM802906, 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), NS00010045, P1610, P2771, EN300-19432, C00146, D00033, Phenol, unstabilized, ReagentPlus(R), >=99.0%, SALICYLIC ACID IMPURITY C [EP IMPURITY], Phenol, p.a., ACS reagent, 99.5-100.5%, PUBLIX Sore Throat Fast Relief Oral Anesthetic, Q130336, CVS Health Sore Throat Fast Relief Oral Anesthetic, J-610001, Phenol, for molecular biology, ~90% (T), liquid, A13-01814, 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, 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, 99.5-10
Phenol crystal is a metabolite found in or produced by Escherichia coli.
Phenol crystal is a white crystalline, aromatic organic compound that is volatile.
Phenylic hydrate is a natural product found in Aspergillus violaceofuscus, Scrophularia buergeriana, and other organisms with data available.
Phenylic hydrate is hydroxybenzene; Carbolic Acid.
Phenylic hydrate, is a colourless crystalline solid with a sweet tarry odor that resembles a hospital smell.
Phenylic hydrate is an antiseptic and disinfectant aromatic alcohol.
Phenylic hydrate appears as a colorless liquid when pure, otherwise pink or red.
Flash point of Phenylic hydrate is 175 °F.
Phenylic hydrate must be heated before ignition may occur easily.
Phenylic hydrate vapors are heavier than air.
Phenylic hydrate does not react with water.
Phenylic hydrate is stable in normal transportation.
P
henol Crystal is reactive with various chemicals and may be corrosive to lead, aluminum and its alloys, certain plastics, and rubber.
Freezing point of Phenylic hydrate is about 105 °F.
Density of Phenylic hydrate is 8.9 lb / gal.
Phenylic hydrate is a white crystalline mass dissolved in an aqueous solution.
Solution may be colorless to slightly pink in color with a distinctive Phenylic hydrate odor; sharp burning taste.
Aqueous solution of Phenylic hydrate will be acidic and act as such.
Phenylic hydrate, solid appears as a solid melting at 110 °F.
Phenylic hydrate is a colorless if pure, otherwise pink or red.
Phenylic hydrate, molten is a white crystalline solid shipped at an elevated temperature to form a semi-solid.
Phenylic hydrate is very hot and may cause burns from contact and also may cause the ignition of combustible materials.
Phenylic hydrate is formed by bonding the OH ⁻ molecule to the benzene ring.
Phenylic hydrates are aromatic compounds in which one or more hydroxyl groups are attached to the aromatic ring.
In its pure form, Phenylic hydrate is a colorless or white to slightly pink crystalline solid.
Phenylic hydrate (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula C6H5OH.
Phenylic hydrate is a white crystalline solid that is volatile.
The molecule consists of a phenyl group (−C6H5) bonded to a hydroxy group (−OH).
Mildly acidic, Phenylic hydrate requires careful handling because it can cause chemical burns.
Phenylic hydrate is primarily used to synthesize plastics and related materials.
Phenylic hydrate and its chemical derivatives are essential for production of polycarbonates, epoxies, explosives, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical drugs.
Phenylic hydrate is both a manufactured chemical and a natural substance.
Phenylic hydrate is a colorless-to-white solid when pure.
The commercial product is a liquid.
Phenylic hydrate has a distinct odor that is sickeningly sweet and tarry.
You can taste and smell Phenylic hydrate at levels lower than those that are associated with harmful effects.
Phenylic hydrate evaporates more slowly than water, and a moderate amount can form a solution with water.
Phenylic hydrate is an organic hydroxy compound that consists of benzene bearing a single hydroxy substituent.
Phenylic hydrate has a role as a disinfectant, an antiseptic drug, a human xenobiotic metabolite and a mouse metabolite.
Phenylic hydrate is a conjugate acid of a phenolate.
Phenylic hydrate is an antiseptic and disinfectant.
Phenylic hydrate is active against a wide range of micro-organisms including some fungi and viruses, but is only slowly effective against spores.
Phenylic hydrate is an organic compound that has the molecular structure of C6H5OH.
Phenylic hydrate is an extremely volatile white crystalline solid that is mildly acidic.
The major uses of Phenylic hydrate, consuming two thirds of its production, involve its conversion to plastics or related materials.
Condensation with acetone gives bisphenol-A, a key precursor to polycarbonates and epoxide resins.
Condensation of Phenylic hydrate, alkylphenols, or diphenols with formaldehyde gives phenolic resins, a famous example of which is Bakelite.
Hydrogenation of Phenylic hydrate gives cyclohexanone, a precursor to nylon.
Nonionic detergents are produced by alkylation of Phenylic hydrate to give the alkylphenols, e.g.,nonylphenol, which are then subjected to ethoxylation
Phenylic hydrate is also a versatile precursor to a large collection of drugs, most notably aspirin but also many herbicides and pharmaceutical drugs.
Phenylic hydrate 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.
Phenylic hydrate is an amino acid derivate that is used to protect plants from infections and pests and is made by the natural degradation of organic waste products.
Phenylic hydrate is soluble in water, alcohol, chloroform, ether, benzene, glycerol, acetone, carbon disulfide and aqueous alkali hydroxides.
Phenylic hydrate is an aromatic organic compound with a wide range of applications in the analytical and molecular biology laboratory, IVD manufacturing and in industry.
Uses of Phenylic Hydrate:
Phenylic hydrate is used as a precursor for cyclohexanone, plastics, nonionic detergents and pharmaceutical drugs like aspirin.
Phenylic hydrate acts as an anesthetic in chloraseptic.
Phenylic hydrate reacts with acetone to get bisphenol-A, which is used in the synthesis of poly carbonates and epoxide resins.
Phenylic hydrate is also used in the manufacture of synthetic resins, dyes, pharmaceuticals, synthetic tanning agents, perfumes, lubricating oils and solvents.
In molecular biology, it is used in the extraction of nucleic acid from tissues by using liquid/liquid Phenylic hydrate-chloroform extraction technique.
Phenylic hydrate is an active component of paint strippers, which is used for the removal of epoxy and polyurethane.
Phenylic hydrate is also used in the preparation of cosmetics, hair colorings and skin lightening preparations.
In the field of medicine, Phenylic hydrate is useful in helping sore throat.
Phenylic hydrate is used as a precursor for cyclohexanone, plastics, nonionic detergents and pharmaceutical drugs like aspirin.
Phenylic hydrate acts as an anesthetic in chloraseptic.
Phenylic hydrate reacts with acetone to get bisphenol-A, which is used in the synthesis of poly carbonates and epoxide resins.
Phenylic hydrate is also used in the manufacture of synthetic resins, dyes, pharmaceuticals, synthetic tanning agents, perfumes, lubricating oils and solvents.
In molecular biology, it is used in the extraction of nucleic acid from tissues by using liquid/liquid Phenylic hydrate-chloroform extraction technique.
Phenylic hydrate is an active component of paint strippers, which is used for the removal of epoxy and polyurethane.
Phenylic hydrate is also used in the preparation of cosmetics, hair colorings and skin lightening preparations.
In the field of medicine, Phenylic hydrate’s spray is useful in helping sore throat.
Phenylic hydrate is used as a germicidal agent and as an intermediate in chemical synthesis.
Phenylic hydrate is commonly used as an antiseptic and disinfectant.
Phenylic hydrate is active against a wide range of micro-organisms including some fungi and viruses, but is only slowly effective against spores.
Phenylic hydrate has been used to disinfect skin and to relieve itching.
Phenylic hydrate is also used in the preparation of cosmetics including sunscreens, hair dyes, and skin lightening preparations.
Phenylic hydrate is also used in the production of drugs (it is the starting material in the industrial production of aspirin), weedkillers, and synthetic resins.
Phenylic hydrate can be found in areas with high levels of motor traffic, therefore, people living in crowded urban areas are frequently exposed to traffic-derived phenol vapor.
The average (mean +/- SD) Phenylic hydrate concentration in urine among normal individuals living in urban areas is 7.4 +/- 2.2 mg/g of creatinine.
Exposure of the skin to concentrated Phenylic hydrate solutions causes chemical burns which may be severe; in laboratories where it is used, it is usually recommended that polyethylene glycol solution is kept available for washing off splashes.
Notwithstanding the effects of concentrated solutions, Phenylic hydrate is also used in cosmetic surgery as an exfoliant, to remove layers of dead skin.
In some bacteria, Phenylic hydrate can be directly synthesized from tyrosine via the enzyme tyrosine phenol-lyase.
Phenylic hydrate is used primarily in the production of phenolic resins and in the manufacture of nylon and other synthetic fibers.
Phenylic hydrate is also used in slimicides (chemicals that kill bacteria and fungi in slimes), as a disinfectant and antiseptic, and in medicinal preparations such as mouthwash and sore throat lozenges.
Phenylic hydrate is used to make plastics, adhesives and other chemicals.
Phenylic hydrate is used to make other chemicals.
Phenylic hydrate is used to make plastics and adhesives.
Phenylic hydrate was first extracted from coal tar, but today is produced on a large scale (about 7 million tonnes a year) from petroleum-derived feedstocks.
Phenylic hydrate is an important industrial commodity as a precursor to many materials and useful compounds.
Phenylic hydrate is so inexpensive that it also attracts many small-scale uses.
Phenylic hydrate is a component of industrial paint strippers used in the aviation industry for the removal of epoxy, polyurethane and other chemically resistant coatings.
Due to safety concerns, Phenylic hydrate is banned from use in cosmetic products in the European Union and Canada.
Concentrated liquid Phenylic hydrate 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.
Phenylic hydrate also has hemostatic and antiseptic qualities that make it ideal for this use.
Phenylic hydrate, usually at 1.4% phenol as an active ingredient, is used medically to treat sore throat.
Phenylic hydrate has been used to disinfect skin and to relieve itching.
Phenylic hydrate is also used as an oral analgesic or anesthetic in products such as Chloraseptic to treat pharyngitis.
Additionally, Phenylic hydrate and its related compounds are used in surgical ingrown toenail treatment, a process termed phenolization.
Research indicates that parental exposure to Phenylic hydrate and its related compounds are positively associated with spontaneous abortion.
During the second world war, Phenylic hydrate injections were used as a means of execution by the Nazis.
Phenylic hydrates are used to describe the solid forms that result from the phenol compound, which is also known as the carbolic acid.
Phenylic hydrate is an extremely volatile white crystalline solid that is mildly acidic.
Phenylic hydrate requires extremely careful handling because its structure can cause painful chemical burns.
Phenylic hydrate is used to describe the solid forms that result from the phenol compound, which is also known as the carbolic acid.
Phenylic hydrate is used in manufacture of Bisphenol- A which is precursor to polycarbonates and epoxide resins.
Phenylic hydrate is used in manufacture of phenolic resins like Bakelite In manufacture of cyclohexanone which is precursor to Nylon.
Phenylic hydrate is used as an intermediate to pharma drugs like aspirin, analgesics and herbicides In making industrial paint strippers, cosmetics and in surgical procedures In manufacture of laminates and foundry resins.
Phenylic hydrate is used in manufacture of agrochemical intermediates, surfactants and anti-oxidants.
Phenylic hydrate’s extracted from petroleum and mainly used as a synthetic building block to produce a wide range of pharmaceutical products and drugs such as aspirin and oral analgesics.
Phenylic hydrate is an antiseptic and disinfectant aromatic alcohol.
Phenylic hydrate is used as a germicidal agent and as an intermediate in chemical synthesis.
Phenylic hydrate, is a colourless crystalline solid with a sweet tarry odor that resembles a hospital smell.
Phenylic hydrate is commonly used as an antiseptic and disinfectant.
Phenylic hydrate is active against a wide range of micro-organisms including some fungi and viruses, but is only slowly effective against spores.
Phenylic hydrate has been used to disinfect skin and to relieve itching.
Phenylic hydrate is also used in the preparation of cosmetics including sunscreens, hair dyes, and skin lightening preparations.
Phenylic hydrate is also used in the production of drugs (it is the starting material in the industrial production of aspirin), weedkillers, and synthetic resins.
Phenylic hydrate is used as a precursor for cyclohexanone, plastics, nonionic detergents and pharmaceutical drugs like aspirin.
Phenylic hydrate acts as an anesthetic in chloraseptic.
Phenylic hydrate reacts with acetone to get bisphenol-A, which is used in the synthesis of poly carbonates and epoxide resins.
Phenylic hydrate is also used in the manufacture of synthetic resins, dyes, pharmaceuticals, synthetic tanning agents, perfumes, lubricating oils and solvents.
In molecular biology, Phenylic hydrate is used in the extraction of nucleic acid from tissues by using liquid/liquid phenol-chloroform extraction technique.
Phenylic hydrate is an active component of paint strippers, which is used for the removal of epoxy and polyurethane.
Phenylic hydrate is also used in the preparation of cosmetics, hair colorings and skin lightening preparations.
In the field of medicine, Phenylic hydrate’s spray is useful in helping sore throat.
Phenylic hydrate is popularly known as Carbolic Acid Liquid and acts as an antimicrobial agent and is used in a variety of pesticides, insecticides, and herbicides.
The major uses of Phenylic hydrate, 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 Phenylic hydrate, alkylphenols, or diphenols with formaldehyde gives phenolic resins, a famous example of which is Bakelite.
Partial hydrogenation of Phenylic hydrate gives cyclohexanone, a precursor to nylon.
Nonionic detergents are produced by alkylation of Phenylic hydrate to give the alkylphenols, e.g., nonylphenol, which are then subjected to ethoxylation.
Phenylic hydrate can be used during the dry summer or winter months.
Phenylic hydrate should be used at least once every three months to avoid a resurgence of pests and insects in the fields.
Spray Phenylic hydrate directly onto the soil early in the morning or late in the evening.
Phenylic hydrate should be added to a sprayer or mixing tank that is already filled with fresh water.
Medical uses:
Phenylic hydrate was widely used as an antiseptic, and it is used in the production of carbolic soap.
Concentrated Phenylic hydrates 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.
Since that time Phenylic hydrate has become the chemical of choice for chemical matrixectomies performed by podiatrists.
Crystal Works:
Phenylic hydrate works by protecting the plants and crops from insects, microbes, pests, and weeds.
Phenylic hydrate works by forming a layer on top of the soil and releasing substances that kill pests.
Recommended Usage:
For spraying, the recommended usage of Phenylic hydrate is 2% weight by volume.
Use 5–10 kg/acre for solid application of Phenylic hydrate.
Benefits of Phenylic Hydrate:
Phenylic hydrate is used in pesticides to ward off pests and pathogens from infecting the plants and to promote plant growth.
Phenylic hydrate deters pests and small insects from eating the plants and destroying the yields.
Phenylic hydrate helps in improving the productivity of crops by protecting them from microbes.
Phenylic hydrate is simple to administer during the planting season.
Phenylic hydrate does not get absorbed by the plants and is therefore safe for use on plants and crops.
Phenylic hydrate has a longer shelf life and is highly stable.
Occurrences of Phenylic Hydrate:
Phenylic hydrate 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 Phenylic hydrate and 4-methylphenol during musth.
Phenylic hydrate is also one of the chemical compounds found in castoreum.
Phenylic hydrate is ingested from the plants the beaver eats.
Phenylic hydrate 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 of Phenylic hydrate is different from and presumably higher than the amount in the distillate.
Biodegradation of Phenylic Hydrate:
Cryptanaerobacter phenolicus is a bacterium species that produces benzoate from Phenylic hydrate via 4-hydroxybenzoate.
Rhodococcus phenolicus is a bacterium species able to degrade Phenylic hydrate as sole carbon source.
Solubility of Phenylic Hydrate:
Phenylic hydrate is soluble in water, alcohol, chloroform, ether, benzene, glycerol, acetone, carbon disulfide and aqueous alkali hydroxides.
Properties of Phenylic Hydrate:
Phenylic hydrate is an organic compound appreciably soluble in water, with about 84.2 g dissolving in 1000 mL (0.895 M).
Homogeneous mixtures of Phenylic hydrate and water at phenol to water mass ratios of ~2.6 and higher are possible.
The sodium salt of Phenylic hydrate, sodium phenoxide, is far more water-soluble.
Phenylic hydrate is a combustible solid (NFPA rating = 2).
When heated, Phenylic hydrate 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 Phenylic hydrate fires.
Acidity:
Phenylic hydrate is a weak acid (pH 6.6).
In aqueous solution in the pH range ca. 8 – 12 it is in equilibrium with the phenolate anion C6H5O− (also called phenoxide or carbolate):
C6H5OH↽⇀C6H5O−+H+
Phenylic hydrate is more acidic than aliphatic alcohols.
Phenylic hydrate’s enhanced acidity is attributed to resonance stabilization of phenolate 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 Phenylic hydrate (pKa 10.0).
Thus, the greater number of resonance structures available to phenoxide compared to acetone enolate seems to contribute little to its stabilization.
However, the situation changes when solvation effects are excluded.
Hydrogen bonding:
In carbon tetrachloride and in alkane solvents, Phenylic hydrate 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.
Phenylic hydrate is classified as a hard acid.
Tautomerism of Phenylic Hydrate:
Phenylic hydrate 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.
Phenylic hydrate therefore exists essentially entirely in the enol form.
4, 4′ Substituted cyclohexadienone can undergo a dienone–Phenylic hydrate rearrangement in acid conditions and form stable 3,4‐disubstituted phenol.
For substituted Phenylic hydrates, 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 phenolate.
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”
Reactions of Phenylic Hydrate:
Phenylic hydrate 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.
Phenylic hydrate 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.
Phenylic hydrate 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.
Friedel Crafts alkylations of Phenylic hydrate 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, a bis(2-hydroxyphenyl) derivative, and a 4-cyclohexylphenols.
Alcohols and hydroperoxides alkylate Phenylic hydrates in the presence of solid acid catalysts (e.g. certain zeolite).
Cresols and cumyl Phenylic hydrates can be produced in that way.
Aqueous solutions of Phenylic hydrate are weakly acidic and turn blue litmus slightly to red.
Phenylic hydrate 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 Phenylic hydrate 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
Phenylic hydrate 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 Phenylic hydrate 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
Phenylic hydrate and its derivatives react with iron(III) chloride to give intensely colored solutions containing phenoxide complexes.
Production of Phenylic Hydrate:
Because of Phenylic hydrate’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.
It 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 Phenylic hydrate 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.
It is oxidized to a hydroperoxide, akin to the production of cumene hydroperoxide.
Via the Hock rearrangement, cyclohexylbenzene hydroperoxide cleaves to give Phenylic hydrate and cyclohexanone.
Cyclohexanone is an important precursor to some nylons.
Oxidation of benzene, toluene, cyclohexylbenzene:
The direct oxidation of benzene (C6H6) to Phenylic hydrate 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 Phenylic hydrate from benzene.
The oxidation of toluene, as developed by Dow Chemical, involves copper-catalyzed reaction of molten sodium benzoate with air:
C6H5CH3 + 2 O2 → C6H5OH + CO2 + H2O
The reaction is proposed to proceed via formation of benzyoylsalicylate.
Autoxidation of cyclohexylbenzene give the hydroperoxide.
Decomposition of this hydroperoxide affords cyclohexanone and Phenylic hydrate.
Older methods:
Early methods relied on extraction of Phenylic hydrate from coal derivatives or the hydrolysis of benzene derivatives.
Hydrolysis:
The original commercial route was developed by Bayer and Monsanto in the early 1900s, based on discoveries by Wurtz and Kekule.
The method involves the reaction of strong base with benzenesulfonic acid, proceeding by the reaction of hydroxide with sodium benzenesulfonate to give sodium phenoxide.
Acidification of the latter gives Phenylic hydrate.
The net conversion is:
C6H5SO3H + 2 NaOH → C6H5OH + Na2SO3 + H2O
Hydrolysis of chlorobenzene
Chlorobenzene can be hydrolyzed to Phenylic hydrate using base or steam:
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:
Phenylic hydrate 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 Phenylic hydrate.
The method is of no commercial interest since the precursor is expensive.
C6H5NH2 + HCl + NaNO2 → C6H5OH + N2 + H2O + NaCl
Salicylic acid decarboxylates to Phenylic hydrate.
History of Phenylic Hydrate:
Phenylic hydrate was discovered in 1834 by Friedlieb Ferdinand Runge, who extracted it (in impure form) from coal tar.
Runge called Phenylic hydrate “Karbolsäure” (coal-oil-acid, carbolic acid).
Coal tar remained the primary source until the development of the petrochemical industry.
French chemist Auguste Laurent extracted Phenylic hydrate 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 “Phenylic hydrate” and “phenyl”.
In 1843, French chemist Charles Gerhardt coined the name “phénol”.
The antiseptic properties of Phenylic hydrate 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 Phenylic hydrate.
The skin irritation caused by continual exposure to Phenylic hydrate 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
Handling and Storage of Phenylic Hydrate:
Handling:
Personal Protective Equipment (PPE):
Always wear appropriate PPE, including gloves, goggles, and lab coats.
It is corrosive and can cause burns on contact with skin.
Ventilation:
Use phenol in a well-ventilated area, preferably in a fume hood, to avoid inhaling fumes.
It vapors can be harmful if inhaled.
Avoidance of Contact:
Minimize contact with skin and eyes.
Use tools and equipment designed to handle corrosive chemicals safely.
Handling Spills:
In case of spills, evacuate the area and use appropriate spill containment measures.
It spills should be handled with care to avoid spreading or causing additional hazards.
Storage:
Container:
Store phenol in tightly closed, appropriately labeled containers.
Use containers made of materials compatible with It , such as glass or certain plastics.
Location:
Keep It in a cool, dry place away from sources of heat and direct sunlight.
Avoid storing it near incompatible substances like strong oxidizers or acids.
Ventilation:
Store It in a well-ventilated area to prevent the accumulation of vapors.
Segregation:
Store It away from food, drinks, and other consumables.
Ensure it is kept away from children and unauthorized individuals.
Stability and Reactivity of Phenylic Hydrate:
Stability:
Thermal Stability:
It is generally stable under normal conditions but can decompose at high temperatures or in the presence of strong oxidizing agents.
Light Sensitivity:
It can degrade under light, so it should be stored in dark containers or away from light sources.
Chemical Stability:
It is stable in neutral and slightly acidic conditions but should be kept away from strong acids and bases.
Reactivity:
Acidity:
It is more acidic than aliphatic alcohols due to resonance stabilization of the phenoxide ion.
It reacts with strong bases to form phenoxide salts.
Electrophilic Aromatic Substitution:
It is reactive towards electrophiles due to the electron-donating effect of the hydroxyl group, leading to various substitution reactions.
Oxidation:
It can be oxidized to form quinones using strong oxidizing agents.
Reaction with Bases and Reducing Agents:
It can form phenoxide salts with strong bases and can be reduced to cyclohexanol under specific conditions.
First Aid Measures of Phenylic Hydrate:
General advice
First aiders need to protect themselves.
Show this material safety data sheet to the doctor in attendance.
If inhaled:
After inhalation:
Fresh air.
Immediately call in physician.
In case of skin contact:
After contact with skin:
Rinse out with polyethylene glycol 400 or a mixture of polyethylene glycol 300/ethanol 2:1 and wash with plenty of water.
If neither is available wash with plenty of water.
Immediately take off contaminated clothing.
Call a physician immediately.
In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Immediately call in ophthalmologist.
Remove contact lenses.
If swallowed:
Give water to drink (two glasses at most).
Seek medical advice immediately.
Do not attempt to neutralise.
Indication of any immediate medical attention and special treatment needed:
No data available
Fire Fighting Measures of Phenylic Hydrate:
Suitable extinguishing media:
Water
Foam
Carbon dioxide (CO2)
Dry powder
Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.
Accidental Release Measures of Phenylic Hydrate:
Environmental precautions:
Do not let product enter drains.
Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up carefully.
Dispose of properly.
Clean up affected area.
Exposure Controls/Personal Protection of Phenylic Hydrate:
Personal protective equipment:
Eye/face protection:
Use equipment for eye protection.
Use tightly fitting safety goggles.
Skin protection:
Full contact:
Material: Viton
Minimum layer thickness: 0,7 mm
Break through time: 480 min
Splash contact:
Material: Viton
Minimum layer thickness: 0,7 mm
Break through time: 480 min
Body Protection:
Use flame retardant antistatic protective clothing.
Respiratory protection:
Recommended Filter type: Filter A-(P3)
Control of environmental exposure:
Do not let product enter drains.
Identifiers of Phenylic Hydrate:
CAS Number: 108-95-2
EC Number: 203-632-7
MDL Number: MFCD00002143
Molar Mass: 94.11 g/mol
Chemical Formula: C₆H₅OH
Hill Formula: C₆H₆O
CAS NO. : 108-95-2
Chemical Formula : C6H6O
Molecular Weight : 94.11
Other Trade Name : Carbolic acid/Phenylic acid
Appearance (Colour): White
Appearance (Form): Crystalline compound
Solubility: 5% aq.solution is clear & colourless
Assay (GC): min. 99.5%
Melting Point: 40 – 41°C
pH (5% aq. solution): 4.5 – 6.0
UN No. : 1671
MDL Number: MFCD00002143
InChI Key: ISWSIDIOOBJBQZ-UHFFFAOYSA-N
Molecular Weight: 94.11 g/mol
EC Number: 203-632-7
MDL Number: MFCD00002143
CAS Number: 108-95-2
EC Index Number: 604-001-00-2
EC Number: 203-632-7
Grade: Ph Eur, ChP, JP, USP
Hill Formula: C₆H₆O
Chemical Formula: C₆H₅OH
Molar Mass: 94.11 g/mol
HS Code: 2907 11 00
Density: 1.07 g/cm3 (at 20 °C)
Explosion Limit: 1.3 – 9.5% (by volume)
Flash Point: 79.0 °C
Ignition Temperature: 595 °C
Melting Point: 38 – 43 °C
pH Value: 5 (50 g/l in H₂O at 20 °C)
Vapor Pressure: 0.2 hPa (at 20 °C)
Bulk Density: 620 kg/m³
Solubility: 84 g/l
Properties of Phenylic Hydrate:
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 g/mol
Monoisotopic Mass: 94.041864811 g/mol
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
Molar Mass: 94.11 g/mol
Boiling Point: 181.7 °C
Density: 1.07 g/cm³
Melting Point: 40.5 °C
Solubility: Soluble in water
Physical State: Crystalline flakes
Odor: Stinging
Melting Point/Freezing Point: 40 – 42 °C (as per literature)
Initial Boiling Point and Boiling Range: 182 °C (as per literature)
Flash Point: 81 °C at approximately 1.013 hPa (closed cup, DIN 51758)
Autoignition Temperature: 715 °C at approximately 1.013 hPa
pH: Approximately 5 at 50 g/l at 20 °C
Viscosity: Dynamic viscosity is 3,437 Pas at 50.00 °C
Water Solubility: 87 g/l at 25 °C
Partition Coefficient (n-octanol/water): log Pow is 1.47 at 30 °C (ECHA),
indicating low bioaccumulation potential
Vapor Pressure: 0.53 hPa at 20.0 °C
Density: 1.071 g/mL at 25 °C (literature value)
Surface Tension: 38.2 mN/m at 50.0 °C
Relative Vapor Density: 3.2 at 20 °C (Air = 1.0)
Density: 1.07 g/cm³ at 20 °C
Explosion Limit: 1.3 – 9.5% (V)
Flash Point: 81 °C
Ignition Temperature: 595 °C
Melting Point: 38 – 43 °C
pH Value: 5 (50 g/l, H₂O, 20 °C)
Vapor Pressure: 0.2 hPa at 20 °C
Bulk Density: 620 kg/m³
Solubility: 84 g/l
Boiling Point (bp): 182 °C (literature value)
Melting Point (mp): 40 – 42 °C (literature value)
Transition Temperature: Solidification point is ≥ 40 °C
Density: 1.071 g/mL at 25 °C (literature value)
Suitability: In accordance with the appearance of the solution
CAS Number: 108-95-2
Empirical Formula: C6H5O