ChemicalBook > Product Catalog > API > Synthetic Anti-infective Drugs > Antiseptics & Disinfectants Drugs > Phenol
Phenol Chemical Properties
- Melting point:40-42 °C(lit.)
- Boiling point:182 °C(lit.)
- Density 1.071 g/mL at 25 °C(lit.)
- vapor density 3.24 (vs air)
- vapor pressure 0.09 psi ( 55 °C)
- refractive index n
- FEMA 3223 | PHENOL
- Flash point:175 °F
- storage temp. 2-8°C
- solubility H2O: 50 mg/mL at 20 °C, clear, colorless
- form liquid
- pka9.89(at 20℃)
- Specific Gravity1.071
- color faintly yellow
- PH3.0-6.0 (25℃, 0.5M in H2O)
- OdorSweet, medicinal odor detectable at 0.06 ppm
- Odor Threshold0.0056ppm
- explosive limit1.3-9.5%(V)
- Water Solubility 8 g/100 mL
- FreezingPoint 41℃
- Sensitive Air & Light Sensitive
- Merck 14,7241
- JECFA Number690
- BRN 969616
- Henry's Law Constant1.09 at 5 °C (average derived from six field experiments, Lüttke and Levsen, 1997)
- Exposure limitsTLV-TWA skin 5 ppm (～19 mg/m3 ) (ACGIH, MSHA, and OSHA); 10-hour TWA 5.2 ppm (～20 mg/m3 ) (NIOSH); ceiling 60 mg (15 minutes) (NIOSH); IDLH 250 ppm (NIOSH).
- CAS DataBase Reference108-95-2(CAS DataBase Reference)
- NIST Chemistry ReferencePhenol(108-95-2)
- IARC3 (Vol. 47, 71) 1999
- EPA Substance Registry SystemPhenol (108-95-2)
- Hazard Codes T,C,F,Xn
- Risk Statements 23/24/25-34-48/20/21/22-68-40-39/23/24/25-11-36-20/21/22-24/25
- Safety Statements 26-36/37/39-45-36/37-28A-28-24/25-1/2-36-16-7
- RIDADR UN 2821 6.1/PG 2
- WGK Germany 2
- RTECS SJ3325000
- F 8-23
- Autoignition Temperature715 °C
- TSCA Yes
- HazardClass 6.1
- PackingGroup II
- HS Code 29071100
- Hazardous Substances Data108-95-2(Hazardous Substances Data)
- ToxicityLD50 orally in rats: 530 mg/kg (Deichmann, Witherup)
Phenol Usage And Synthesis
- Chemical PropertiesPhenol is commonly known as carbolic acid. The chemical properties of phenol are very active, and it turns to reddish crystals in the air or in contact with any impurities. It absorbs the moisture in the air and gradually liquefies in the air. Phenol is slightly soluble in water, soluble in benzene, alkaline solution and organic solvents such as ethanol, ether, chloroform, glycerol, etc. Phenol is weakly acidic and reacts with base to form salt. It appears blue when being dissolved in ferric chloride solution.
- UsesPhenol is an important organic chemical raw material, widely used in the production of phenolic resin and bisphenol A, in which bisphenol A is important raw material for polycarbonate, epoxy resin, polysulfone resin and other plastics. In some cases the phenol is used to produce iso-octylphenol, isononylphenol, or isododecylphenol through addition reaction with long-chain olefins such as diisobutylene, tripropylene, tetra-polypropylene and the like, which are used in production of nonionic surfactants. In addition, it can also be used as an important raw material for caprolactam, adipic acid, dyes, medicines, pesticides and plastic additives and rubber auxiliaries.
- ProductionCoal tar was once the main source of phenol, and was extracted from sodium hydroxide solution. In earlier time, people use sulfonation method to produce phenol: react sodium benzene sulfonate with sodium hydroxide to generate the sodium salt of phenol, and then treat it with acid to obtain phenol. In recent years, hydrolyzing chlorobenzene or oxidizing cumene has become the major production method. The by-product acetone in latter method is also an important industrial raw material, so oxidizing cumene is more economic industrially thus widely applied.
This method generates cumene from propylene and benzene in the presence of aluminum trichloride. It oxidizes to cumene hydroperoxide and then decomposes with cation exchange resin to give phenol and acetone. For each ton of phenol produced, 0.62 tons of acetone can be produced.
se sulfuric acid to sulfonate benzene to generate benzene sulfonic acid, neutralize it with sodium sulfite, and then undergo acidification and vacuum distillation in caustic soda solution.
Hydrogen benzene hydrolysis method: hydrogen benzene is hydrolyzed in caustic soda solution with high temperature and high pressure to generate phenol sodium, which is then neutralized to give phenol.
- ToxicityPhenol is highly corrosive and toxic. It mainly affects the central nervous system. The oral lethal dose for adults is 1 g. It can be irritating, numbing or necrotizing to the skin. It is toxic to skin contact, swallowing or inhalation of phenol. Misuse of a small amount of phenol can cause nausea, vomiting, shock, coma and even death in case of respiratory failure. Very few amounts are used as a preservative, so that adverse reactions are rarely found.
Due to its high toxicity, it has been replaced by more effective and less toxic phenolic derivatives.
- DescriptionPhenol is a stable chemical substance and appear as colourless/white crystals with a characteristic, distinct aromatic/acrid odour. It is reactive and incompatible with strong oxidising agents, strong bases, strong acids, alkalis, and calcium hypochlorite. Phenol is flammable and may discolour in light. Phenol is used in the manufacture or production of explosives, fertiliser, coke, illuminating gas, lampblack, paints, paint removers, rubber, perfumes, asbestos goods, wood preservatives, synthetic resins, textiles, drugs, and pharmaceutical preparations. It is also extensively used as a disinfectant in the petroleum, leather, paper, soap, toy, tanning, dye, and agricultural industries.
- Chemical PropertiesPhenol, C6H5OH, also known as carbolic acid and phenylic acid, is a white poisonous crystalline solid that melts at 43 °C (110 OF) and boils at 182°C (360 OF). Phenol has a sharp burning taste,a distinctive odor, and it irritates tissue. It is toxic not only by ingestion or inhalation, but also by skin absorption. Phenol is soluble in water,alcohol,and ether. It is used in the production of resins,germicides,weedkillers,pharmaceuticals, and as a solvent in the refining of lubricating oils.
- Chemical PropertiesPhenol is a stable chemical substance of colorless/white crystals with a characteristically distinct aromatic/acrid odor. It is reactive and incompatible with strong oxidizing agents, strong bases, strong acids, alkalis, and calcium hypochlorite. It is flammable and discolors in light. Phenol is used in the manufacture or production of explosives, fertilizer, coke, illuminating gas, lampblack, paints, paint removers, rubber, perfumes, asbestos goods, wood preservatives, synthetic resins, textiles, drugs, and pharmaceutical preparations. It is also used extensively as a disinfectant in the petroleum, leather, paper, soap, toy, tanning, dye, and agricultural industries. Phenol is a systemic poison and constitutes a serious health hazard. The risks of using it in the laboratory must be fully assessed before work begins. Typical MEL 2 ppm; typical OEL 1 ppm.
- Chemical PropertiesPhenol is a colorless to light-pink, crystalline solid. Sweet, acrid odor. Phenol liquefies by mixing with about 8% water. The Odor Threshold in air is 0.04 ppm and in water is 7.9 ppm.
- Chemical PropertiesPhenol occurs as colorless to light pink, caustic, deliquescent needleshaped crystals or crystalline masses with a characteristic odor. When heated gently phenol melts to form a highly refractive liquid. The USP 32 permits the addition of a suitable stabilizer; the name and amount of substance used for this purpose must be clearly stated on the label.
- Chemical PropertiesPhenol has a strong odor that is sickeningly sweet and irritating. Phenol has powerful disinfectant and sanitizing qualities. It has been used as a topical anesthetic and antiseptic preservative, reagent and chemical reactant. Its use for direct addition to food is limited to a role as a flavoring ingredient in a few foods at a maximum level below 10 ppm.
- Physical propertiesPhenol is a colorless or white crystalline solid that is slightly soluble in water. Phenol is the simplest of the large group of organic chemicals known as phenols, which consist of compounds where a carbon in the phenyl aromatic group (C6H5) is directly bonded to hydroxyl, OH.
- OccurrenceIt is reported found in over 150 natural products including apricot, sour cherry, black currant, bilberry, cranberry, other berries, grapes, guava fruit, peach, pineapple, asparagus, onion, cooked potato, tomato, cinnamon bark, cassia leaf, ginger, pennyroyal oil, many cheeses, butter, milk, milk powder, boiled egg, fish and fish oil, cooked and cured meats, beer, wheaten bread, crisp bread, cognac, rose wine, cocoa, coffee, tea, whiskies, roasted filbert, roasted peanut, soybean, pecans, honey, avocado, Arctic bramble, passion fruit, beans, mushrooms, burley tobacco, cooked beef and chicken, fermented soy sauce, trassi, roasted almonds, sesame seed, fenugreek, mango, tamarind, Brazil nut, rice, rhubarb, licorice, buckwheat, watercress, malt, wort, dried bonito, loquat, myrtle berry, rosemary, Tahiti and Bourbon vanilla, endive, shrimp, crab, crayfish, clam, squid, truffle and Chinese quince.
- HistoryPhenol’s first prominent use was by Joseph Lister (1827–1912) as an antiseptic. Throughout human history,infection often resulted in death,even when the wound could be surgically treated.A broken bone piercing the skin, which today is a painful but not life-threatening injury,historically resulted in infection and possible amputation or death. Lister was inspired by Louis Pasteur’s (1822–1895) germ theory of disease,and he began to use antiseptic methods during routine surgery during the 1860s.
- UsesPhenol is used in the manufacture of variousphenolic resins; as an intermediate in the production of many dyes and pharmaceuticals;as a disinfectant for toilets, floors, and drains;as a topical antiseptic; and as a reagentin chemical analysis. It has been detectedin cigarette smoke and automobile exhaust.Smoke emitted from a burning mosquito coil(a mosquito repellent) has been found to con-tain submicron particles coated with phenoland other substances; a lengthy exposure canbe hazardous to health (Liu et al. 1987).
- UsesPurified for molecular genetics applications
- Usesphenol is frequently used for medical chemical face peels. It may trap free radicals and can act as a preservative. Phenol, however, is an extremely caustic chemical with a toxicity potential. It is considered undesirable for use in cosmetics. even at low concentrations, it frequently causes skin irritation, swelling, and rashes.
- UsesBase raw material for Alkyl Phenols, Phenol-Formaldehyde Resins, Epoxy Resins and Lube & Fuel Additives
- UsesThe predominant use of phenol today is for phenolic resins.it is a powerful bactericide,phenol can be found in numerous consumer products includingmouthwashes,antiseptic ointments,throat lozenges,air fresheners,eardrops,and lipbalms.
Phenol continues to be a primary chemical used to make thermoset resins.These resinsare made by combining phenol with aldehydes such as formaldehyde.More than 4 billionpounds of phenolic resins are used annually in the United States.Phenolic resins findtheir widest use in the construction industry.They are used as binding agents and fillers inwood products such as plywood,particleboard,furniture, and paneling.Phenolic resins areimpregnated into paper,which,after hardening,produces sheets that can be glued togetherto form laminates for use in wall paneling and countertops.Decking in boats and docksare made from phenolic resin composites.Phenolic resins are used as sealing agents andfor insulation. Because phenolic resins have high heat resistance and are good insulators,they are used in cookware handles.Because they are also good electrical insulators,they areused in electrical switches,wall plates, and for various other electrical applications.In theautomotive industry,phenolic resins are used for parts such as drive pulleys,water pumphousings, brakes,and body parts.
In addition to the construction industry,phenol has many other applications.It isused in pharmaceuticals,in herbicides and pesticides,and as a germicide in paints.It can beused to produce caprolactam,which is the monomer used in the production of nylon 6.Another important industrial compound produced from phenol is bisphenol A,which ismade from phenol and acetone.Bisphenol A is used in the manufacture of polycarbonateresins.Polycarbonate resins are manufactured into structural parts used in the manufactureof various products such as automobile parts,electrical products,and consumer appliances.Items such as compact discs, reading glasses,sunglasses,and water bottles are made frompolycarbonates.
- PreparationPhenol is formed in dry distillation of wood, peat and coal; coal tar is one of the commercial sources of phenol and its homologues.
- IndicationsPhenol in dilute solution (0.5% to 2%) decreases itch by anesthetizing the cutaneous nerve endings. Phenol should never be used on pregnant women or infants younger than 6 months of age.
- DefinitionChEBI: An organic hydroxy compound that consists of benzene bearing a single hydroxy substituent. The parent of the class of phenols.
- Production MethodsPhenol was prepared before World War I through the distillation of coal tar. The firstsynthetic process involved the sulfonation of benzene followed by desulfonation with abase.
The most common current method of phenol production is from the cumene hydroperoxiderearrangement process.In this process,benzene reacts with propylene to produce cumene.Cumene is oxidized to cumene hydroperoxide.When cumene hydroperoxide is treated withdilute sulfuric acid,it rearranges and splits into phenol and acetone. Because the reactants areinexpensive and the process is simple,the acidic oxidation of cumene is used to produce morethan 95% of the world’s supply of phenol.
- Definition1. (carbolic acid,
hydroxybenzene, C6H5OH) A white crystalline
solid used to make a variety of other
2. A type of organic compound in which at least one hydroxyl group is bound directly to one of the carbon atoms of an aromatic ring. Phenols do not show the behavior typical of alcohols. In particular they are more acidic because of the electron-withdrawing effect of the aromatic ring. The preparation of phenol itself is by fusing the sodium salt of the sulfonic acid with sodium hydroxide:
C6H5SO2.ONa + 2NaOH → C6H5ONa
+ Na2SO3 + H2O
The phenol is then liberated by sulfuric acid:
2C6H5ONa + H2SO4 → 2C6H5OH + Na2SO4
Reactions of phenol include:
1. Replacement of the hydroxyl group with a chlorine atom using phosphorus(V) chloride.
2. Reaction with acyl halides to form esters of carboxylic acids. 3. Reaction with haloalkanes under alkaline conditions to give mixed alkyl–aryl ethers.
In addition phenol can undergo further substitution on the benzene ring. The hydroxyl group directs other substituents into the 2- and 4-positions.
- Production MethodsHistorically, phenol was produced by the distillation of coal tar. Today, phenol is prepared by one of several synthetic methods, such as the fusion of sodium benzenesulfonate with sodium hydroxide followed by acidification; the hydrolysis of chlorobenzene by dilute sodium hydroxide at high temperature and pressure to give sodium phenate, which on acidification liberates phenol (Dow process); or the catalytic vapor-phase reaction of steam and chlorobenzene at 500°C (Raschig process).
- brand name3p maid;Agre-gola;Anbesol;Apralan;Benamine;Carbolic acid;Cepastat;Chloraseptic dm;Derma cas;Ego psoryl;Egomycol;Epivetol;Fenicado;Hydroxybenzene;Izal germicide;Merastat;Monophenol;Pao sole;Pernomol;Phenylic acid;Poscle;Pregine;Protaphane hm insulin;Sarna;Sedaural;Vaopin.
- World Health Organization (WHO)Phenol became widely used as an antiseptic following demonstration of its germicidal activity in 1867. It is an intensely corrosive substance and percutaneous absorption can produce serious systemic toxicity. It has been withdrawn from pharmaceutical preparations by at least one national regulatory authority. However, it is still used widely in concentrations of the order of 1.4% in proprietary preparations for the relief of soreness of the mouth and throat.
- Aroma threshold valuesDetection: 5.5 ppm. Aroma characteristics at 1.0%: medicinal, creosote, smoky, spicy, phenolic, leatherlike with notes of fried meat and coffee.
- Taste threshold valuesTaste characteristics at 3 ppm: spicy, phenolic, tobacco, musty, woody, medicinal, smoky, tarlike and slightly spicy clovelike.
- Synthesis Reference(s)Journal of the American Chemical Society, 107, p. 2153, 1985 DOI: 10.1021/ja00293a054
Synthetic Communications, 19, p. 453, 1989 DOI: 10.1080/00397918908050686
- General DescriptionA solid melting at 110°F. Colorless if pure, otherwise pink or red. Flash point 175°F. Density 9.9 lb / gal. Vapors are heavier than air Corrosive to the skin (turning skin white) but because of its anesthetic quality numbs rather than burn. Lethal amounts can be absorbed through the skin. Used to make plastics and adhesives.
- Air & Water ReactionsDecomposes slowly in air. Mixtures of 9-10% phenol in air are explosive. Soluble in water
- Reactivity ProfilePHENOL is a weak acid. Reacts exothermically with bases. Reacts with strong oxidizing agents. Emits acrid smoke and irritating fumes when heated to decomposition. Undergoes, in the presence of aluminum chloride, potentially explosive reactions with nitromethane, butadiene, formaldehyde, peroxodisulfuric acid, peroxosulfuric acid, and sodium nitrite . Reacts violently with sodium nitrate in the presence of trifluoroacetic acid [Bretherick, 5th ed., 1995, p. 770]. May corrode lead, aluminum and its alloys, certain plastics, and rubber. Phenol may explode in contact with peroxodisulfuric acid (Dns, J. Ber., 1910, 43, 1880; Z. Anorg. Chem., 1911, 73, 1911.) or peroxomonosulfuric acid. (Sidgwick, 1950, 939)
- Health HazardToxic hazard rating is very toxic: probable oral lethal dose (human) is 50-500 mg/kg. Ingestion of 1 gram has been lethal to humans. Lethal amounts may be absorbed through skin or inhaled. Industrial contact can cause chronic poisoning with kidney and liver damage. Persons affected with hepatic or kidney diseases are at a greater risk.
- Health HazardExposures to phenol cause adverse health effects and poisoning. Phenol is absorbed very rapidly through surfaces of the skin, lungs, and stomach. The symptoms of prolonged exposures and poisoning include, but are not limited to, vomiting, diffi culty in swallowing, diarrhea, lack of appetite, headache, fainting, dizziness, mental disturbances, and skin rash. Direct contact with phenol causes burning of the mouth, irritation to the eyes, nose, and dermatitis, discoloration of the skin, and damage to the liver and kidneys. Exposure to phenol in different concentrations is known to cause mental disturbances, depression of the CNS, and coma.
- Health HazardPhenol is a corrosive substance with mod-erate to high toxicity. The acute poisoning effects are high in most animals. In humans,ingestion of 5–10 g of solid can cause death.The toxic symptoms include nausea, vomiting, weakness, muscular pain, dark urine,cyanosis, tremor, convulsions, and kidneyand liver damage. In addition, it is an irritant to the eyes, nose, and throat and cancause skin burn and dermatitis. Inhalation ofits vapors or absorption of the solid solutionor vapor through skin can produce similartoxic effects. Phenol vapors can readily beabsorbed through the skin.
Absorption of phenol through intact skin,as determined from the blood phenol levelsin the test animals, depended on the surfacearea of applications rather than its concentrations in the test solutions (Pullin 1978). Theanimals (swines) showed the signs of twitching and tremors within a few minutes ofapplications, which were followed by salivation, nasal discharge, and labored breathing.
LD50 value, oral (mice): 270 mg/kg
LC50 value, inhalation (mice): 177 mg/kg
Krajnovic-Ozretic and Ozretic (1988)investigated the effects of water pollutionby phenol on fish. An 8-day exposure to7.5 mg/L of phenol produced damage tothe gills, gallbladder, liver, and kidney ingray mullet. A higher concentration, above10 mg/L, was lethal in several hours, while alower level of 0.5 mg/L was nontoxic duringan 8-day exposure.
Snails (Indoplanorbis exustus) secretedmucus and developed hemorrhage in a highlyconcentrated phenol environment. A 96-hourmedian lethal concentration was determinedas 125.75 mg/L (Agrawal 1987).
Suppiah and Perry (2005) have reporteda case history of phenol-induced hepatitisin a male patient. The patient was admittedwith jaundice six days after phenol-injectionschlerotherapy for haemorrhoids.
- Health HazardPhenol is a corrosive and moderately toxic substance that affects the central nervous system and can cause damage to the liver and kidneys. Phenol is irritating to the skin but has a local anesthetic effect, so that no pain may be felt on initial contact. A whitening of the area of contact generally occurs, and later severe burns may develop. Phenol is rapidly absorbed through the skin, and toxic or even fatal amounts can be absorbed through relatively small areas. Exposure to phenol vapor can cause severe irritation of the eyes, nose, throat, and respiratory tract. Acute overexposure by any route may lead to nausea, vomiting, muscle weakness, and coma. Contact of phenol with the eyes may cause severe damage and possibly blindness. Ingestion of phenol leads to burning of the mouth and throat and rapid development of digestive disturbances and the systemic effects described above. As little as 1 g can be fatal to humans. Phenol is regarded as a substance with good warning properties.
Chronic exposure to phenol may cause vomiting, diarrhea, dizziness, difficulty in swallowing, headache, skin discoloration, and injury to the liver. Phenol has not been shown to be a carcinogen in humans. There is some evidence from animal studies that phenol may be a reproductive toxin.
- Fire HazardPhenol is a combustible solid (NFPA rating = 2). When heated, phenol produces flammable vapors that are explosive at concentrations of 3 to 10% in air. Carbon dioxide or dry chemical extinguishers should be used to fight phenol fires.
- Fire HazardFlammable vapors when heated. Runoff from fire control water may give off poisonous gases and cause pollution. Mixtures of 9-10% phenol in air are explosive. Avoid aluminum chloride/nitrobenzene mixture, peroxodisulfuric acid, peroxomonosulfuric acid and strong oxidizing agents. Decomposes slowly on air contact. Avoid contact with strong oxidizing agents.
- Flammability and ExplosibilityPhenol is a combustible solid (NFPA rating = 2). When heated, phenol produces flammable vapors that are explosive at concentrations of 3 to 10% in air. Carbon dioxide or dry chemical extinguishers should be used to fight phenol fires.
- Pharmaceutical ApplicationsPhenol is used mainly as an antimicrobial preservative in parenteral
pharmaceutical products. It has also been used in topical
pharmaceutical formulations and cosmetics;
Phenol is widely used as an antiseptic, disinfectant, and therapeutic agent, although it should not be used to preserve preparations that are to be freeze-dried.
- Industrial usesPhenol is the simplest member of a class oforganic compounds possessing a hydroxylgroup attached to a benzene ring or to a morecomplex aromatic ring system.
Also known as carbolic acid or monohydroxybenzene,phenol is a colorless to whitecrystalline material of sweet odor, having thecomposition C6H5OH, obtained from the distillationof coal tar and as a by-product ofcoke ovens.
Phenol has broad biocidal properties, anddilute aqueous solutions have long been usedas an antiseptic. At higher concentrations itcauses severe skin burns; it is a violent systemicpoison. It is a valuable chemical raw materialfor the production of plastics, dyes, pharmaceuticals,syntans, and other products.
Phenol is one of the most versatile industrialorganic chemicals. It is the starting point formany diverse products used in the home andindustry. A partial list includes nylon, epoxyresins, surface active agents, synthetic detergents,plasticizers, antioxidants, lube oil additives,phenolic resins (with formaldehyde, furfural,and so on), cyclohexanol, adipic acid,polyurethanes, aspirin, dyes, wood preservatives,herbicides, drugs, fungicides, gasolineadditives, inhibitors, explosives, and pesticides.
- Safety ProfileHuman poison by ingestion. An experimental poison by ingestion, subcutaneous, intravenous, parenteral, and intraperitoneal routes. Moderately toxic by skin contact. A severe eye and skin irritant. Questionable carcinogen with experimental carcinogenic and neoplastigenic data. Mutation data reported. An experimental teratogen. Absorption of phenolic solutions through the skin may be very rapid, and can cause death within 30 minutes to several hours by exposure of as little as 64 square inches of skin. Lesser exposures can cause damage to the ladneys, liver, pancreas, and spleen, and edema of the lungs. Ingestion can cause corrosion of the lips, mouth, throat, esophagus, and stomach, and gangrene. Ingestion of 1.5 g has lulled. Chronic exposures can cause death from liver and kidney damage. Dermatitis resulting from contact with phenol or phenol-containing products is fairly common in industry. A common air contaminant.Combustible when exposed to heat, flame or oxidizers. Potentially explosive reaction with aluminum chloride + nitromethane (at 1 10°C/lOO bar), formaldehyde, perijxydisulfuric acid, peroxymonosulfuric acid, sodium nitrite + heat. Violent reaction with aluminum chloride + nitrobenzene (at 120℃), sodium nitrate + trifluoroacetic acid, butadiene. Can react with oxidizing materials. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.
- SafetyPhenol is highly corrosive and toxic, the main effects being on the
central nervous system. The lethal human oral dose is estimated to
be 1 g for an adult.
Phenol is absorbed from the gastrointestinal tract, skin, and mucous membranes, and is metabolized to phenylglucuronide and phenyl sulfate, which are excreted in the urine.
Although there are a number of reports describing the toxic effects of phenol, these largely concern instances of accidental poisoning or adverse reactions during its use as a therapeutic agent.Adverse reactions associated with phenol used as a preservative are less likely owing to the smaller quantities that are used; however, it has been suggested that the body burden of phenol should not exceed 50 mg in a 10-hour period.This amount could be exceeded following administration of large volumes of phenolpreserved medicines.
LD50 (mouse, IV): 0.11 g/kg
LD50 (mouse, oral): 0.3 g/kg
LD50 (rabbit, skin): 0.85 g/kg
LD50 (rat, skin): 0.67 g/kg
LD50 (rat, oral): 0.32 g/kg
LD50 (rat, SC): 0.46 g/kg
- Potential ExposurePhenol is used as a pharmaceutical, in the production of fertilizer; coke, illuminating gas; lampblack, paints, paint removers; rubber, asbestos goods; wood preservatives; synthetic resins; textiles, drugs, pharmaceutical preparations; perfumes, bakelite, and other plastics (phenolformaldehyde resins); polymer intermediates (caprolactam, bisphenol-A and adipic acid). Phenol also finds wide use as a disinfectant and veterinary drug.
- CarcinogenicityPhenol had been investigated for carcinogenicity in animals by the oral and dermal routes. IARC and IRIS determined that animal human evidence for carcinogenicity was inadequate.
- SourceDetected in distilled water-soluble fractions of 87 octane unleaded gasoline (1.53 mg/L),
94 octane unleaded gasoline (0.19 mg/L), Gasohol (0.33 mg/L), No. 2 fuel oil (0.09 mg/L), jet fuel
A (0.09 mg/L), diesel fuel (0.07 mg/L), and military jet fuel JP-4 (0.22 mg/L) (Potter, 1996).
Phenol was also detected in 80% of 65 gasoline (unleaded regular and premium) samples (62 from
Switzerland, 3 from Boston, MA). At 25 °C, phenol concentrations ranged from 63 to 130,000
μg/L in gasoline and from 150 to 1,500 μg/L in water-soluble fractions. Average concentrations
were 26 mg/L in gasoline and 6.1 mg/L in water-soluble fractions (Schmidt et al., 2002).
Thomas and Delfino (1991) equilibrated contaminant-free groundwater collected from Gainesville, FL with individual fractions of three individual petroleum products at 24–25 °C for 24 h. The aqueous phase was analyzed for organic compounds via U.S. EPA approved test method 625. Average phenol concentrations reported in water-soluble fractions of unleaded gasoline, kerosene, and diesel fuel were 20, 8, and 19 μg/L, respectively.
A high-temperature coal tar contained phenol at an average concentration of 0.61 wt % (McNeil, 1983).
Phenol occurs naturally in many plants including blueberries (10 to 60 ppb), marjoram (1,431– 8,204 ppm), sweetflag, safflower buds (40 ppb), mud plantain, capillary wormwood, asparagus shoots, tea leaves, petitgrain, cinnamon, cassia, licorice, witch hazel, Japanese privet, St. John’s wort, European pennyroyal, tomatoes, white mulberries, tobacco leaves, benneseed, sesame seeds, tamarind, white sandlewood, patchouli leaves, rue, slash pine, bayberries, Scotch pine, and tarragon (Duke, 1992).
A liquid swine manure sample collected from a waste storage basin contained phenol at a concentration of 22.0 mg/L (Zahn et al., 1997).
Schauer et al. (2001) measured organic compound emission rates for volatile organic compounds, gas-phase semi-volatile organic compounds, and particle phase organic compounds from the residential (fireplace) combustion of pine, oak, and eucalyptus. The gas-phase emission rates of phenol were 525 mg/kg of pine burned, 300 mg/kg of oak burned, and 434 mg/kg of eucalyptus burned.
Releases toxic and noxious fumes when heated at temperatures greater than its boiling point.
Drinking water standard: No MCLGs or MCLs have been proposed, however, a DWEL of 20 mg/L was recommended (U.S. EPA, 2000).
- Environmental FateBiological. Under methanogenic conditions, inocula from a municipal sewage treatment plant
digester degraded phenol to carbon dioxide and methane (Young and Rivera, 1985).
Chloroperoxidase, a fungal enzyme isolated from Caldariomyces fumago, reacted with phenol
forming 2- and 4-chlorophenol, the latter in a 25% yield (Wannstedt et al., 1990). In activated
sludge, 41.4% mineralized to carbon dioxide after 5 d (Freitag et al., 1985). When phenol was
statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater
inoculum, significant biodegradation with rapid adaptation was observed. At concentrations of 5
and 10 mg/L, 96 and 97% biodegradation, respectively, were observed after 7 d (Tabak et al.,
1981). Phenol is rapidly degraded in aerobically incubated soil but is much slower under anaerobic
conditions (Baker and Mayfield, 1980).
Soil. Loehr and Matthews (1992) studied the degradation of phenol in different soils under aerobic conditions. In a slightly basic sandy loam (3.25% organic matter) and in acidic clay soil (<1.0% organic matter), the resultant degradation half-lives were 4.1 and 23 d, respectively. Soil sorption distribution coefficients (Kd) were determined from centrifuge column tests using kaolinite as the absorbent (Celorie et al., 1989). Values for Kd ranged from 0.010 to 0.054 L/g.
Surface Water. Vaishnav and Babeu (1987) reported a half-life of 11 d in river waters and 3 d in harbor waters.
Groundwater. Nielsen et al. (1996) studied the degradation of phenol in a shallow, glaciofluvial, unconfined sandy aquifer in Jutland, Denmark. As part of the in situ microcosm study, a cylinder that was open at the bottom and screened at the top was installed through a cased borehole approximately 5 m below grade. Five liters of water was aerated with atmospheric air to ensure aerobic conditions were maintained. Groundwater was analyzed weekly for approximately 3 months to determine phenol concentrations with time. The experimentally determined first-order biodegradation rate constant and corresponding half-life were 0.5/d and 33.4 h, respectively. Vaishnav and Babeu (1987) reported a biodegradation rate constant of 0.035/d and a half-life of 20 d in groundwater.
Photolytic. Absorbs UV light at a maximum wavelength of 269 nm (Dohnal and Fenclová, 1995). In an aqueous, oxygenated solution exposed to artificial light (λ = 234 nm), phenol was photolyzed to hydroquinone, catechol, 2,2 -, 2,4 - and 4,4 -dihydroxybiphenyl (Callahan et al., 1979). When an aqueous solution containing potassium nitrate (10 mM) and phenol (1 mM) was irradiated with UV light (λ = 290–350 nm) up to a conversion of 10%, the following products formed: hydroxyhydroquinone, hydroquinone, resorcinol, hydroxybenzoquinone, benzoquinone, catechol, nitrosophenol, 4-nitrocatechol, nitrohydroquinone, 2- and 4-nitrophenol. Catechnol and hydroquinone were the major and minor products, respectively (Niessen et al., 1988). Titanium dioxide suspended in an aqueous solution and irradiated with UV light (λ = 365 nm) converted phenol to carbon dioxide at a significant rate (Matthews, 1986).
Chemical/Physical. In an environmental chamber, nitrogen trioxide (10,000 ppb) reacted quickly with phenol (concentration 200 ppb to 1.4 ppm) to form phenoxy radicals and nitric acid (Carter et al., 1981). The phenoxy radicals may react with oxygen and nitrogen dioxide to form quinones and nitrohydroxy derivatives, respectively (Nielsen et al., 1983).
- storageWhen exposed to air and light, phenol turns a red or brown color, the color being influenced by the presence of metallic impurities. Oxidizing agents also hasten the color change. Aqueous solutions of phenol are stable. Oily solutions for injection may be sterilized in hermetically sealed containers by dry heat. The bulk material should be stored in a well-closed, light-resistant container at a temperature not exceeding 15°C.
- storageBecause of its corrosivity and ability to penetrate the skin, all work with phenol and its solutions should be conducted while wearing impermeable gloves, appropriate protective clothing, and splash goggles. Operations with the potential to produce dusts or aerosols of phenol or its solutions should be carried out in a fume hood.
- ShippingUN1671 Phenol, solid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN2312 Molten phenol, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN2821 Phenol solutions, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
- Purification MethodsSteam is passed through a boiling solution containing 1mole of phenol and 1.5-2.0moles of NaOH in 5L of H2O until all non-acidic material has distilled. The residue is cooled, acidified with 20% (v/v) H2SO4, and the phenol is separated, dried with CaSO4 and fractionally distilled under reduced pressure. It is then fractionally crystallised several times from its melt [Andon et al. J Chem Soc 5246 1960]. Purification via the benzoate has been used by Berliner, Berliner and Nelidow [J Am Chem Soc 76 507 1954]. The benzoate,(m 70o, b 314o/760mm), is crystallised from 95% EtOH, then hydrolysed to the free phenol by refluxing with two equivalents of KOH in aqueous EtOH until the solution becomes homogeneous. It is acidified with HCl and extracted with diethyl ether. The ether layer is freed from benzoic acid by thorough extraction with aqueous NaHCO3, and, after drying and removing the ether, the phenol is distilled. Phenol has also been crystallised from a 75% w/w solution in water by cooling to 11o and seeding with a crystal of the hydrate. The crystals are centrifuged off, rinsed with cold water (0-2o), saturated with phenol, and dried. It can be crystallised from pet ether [Berasconi & Paschalis J Am Chem Soc 108 2969 1986]. Draper and Pollard [Science 109 448 1949] added 12% water, 0.1% aluminium (can also use zinc) and 0.05% NaHCO3 to phenol, and distilled it at atmospheric pressure until the azeotrope was removed, The phenol was then distilled at 25mm. Phenol has also been dried by distillation from the *benzene solution to remove the water/*benzene azeotrope and the excess *benzene, followed by distillation of the phenol at reduced pressure under nitrogen. Processes such as this are probably adequate for analytical grade phenol which has as its main impurity water. Phenol has also been crystallised from pet ether/*benzene or pet ether (b 40-60o). The purified material is stored in a vacuum desiccator over P2O5 or CaSO4. [Beilstein 6 IV 531.]
- IncompatibilitiesVapors may form explosive mixture with air. The aqueous solution is a weak acid. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, calcium hypochlorite; aluminum chloride. acids. Reacts with metals.
- IncompatibilitiesPhenol undergoes a number of chemical reactions characteristic of
alcohols; however, it possesses a tautomeric enol structure that is
weakly acidic. It will form salts with sodium hydroxide or
potassium hydroxide, but not with their carbonates or bicarbonates.
Phenol is a reducing agent and is capable of reacting with ferric salts in neutral to acidic solutions to form a greenish-colored complex. Phenol decolorizes dilute iodine solutions, forming hydrogen iodide and iodophenol; stronger solutions of iodine react with phenol to form the insoluble 2,4,6-triiodophenol.
Phenol is incompatible with albumin and gelatin as they are precipitated. It forms a liquid or soft mass when triturated with compounds such as camphor, menthol, thymol, acetaminophen, phenacetin, chloral hydrate, phenazone, ethyl aminobenzoate, methenamine, phenyl salicylate, resorcinol, terpin hydrate, sodium phosphate, or other eutectic formers. Phenol also softens cocoa butter in suppository mixtures.
- Waste DisposalConsult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Incineration.
- PrecautionsAcute poisoning of phenol by ingestion, inhalation or skin contact may lead to death. Phenol is readily absorbed through the skin. It is highly toxic by inhalation. It is corrosive and causes burns and severe irritation effects. During use and handling of phenol, occupational workers should be very careful. Workers should use protective clothing, rubber boots, and goggles to protect the eyes from vapors and spillage.
- Regulatory StatusIncluded in the FDA Inactive Ingredients Database (injections). Included in medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.
Phenol Preparation Products And Raw materials
- Preparation ProductsOctadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate2,4,6-Trichlorophenol6-PHENOXYNICOTINONITRILEBISPHENOL A DIMETHACRYLATE4-NITROPHENYL PHENYL ETHERFenpropathrin4-Hydroxycinnamic acidTetrabromophenol BlueDIPHENYL PHTHALATEXanthene3-PHENOXYANILINE4'-PhenoxyacetophenoneTris(2,4-ditert-butylphenyl) phosphiteDL-4-HYDROXYMANDELIC ACID MONOHYDRATEHigh temperature levelling agent BOFSeratrodast2-Phenoxypropionic acid4-ChromanoneDispersing agent SSodium pentachlorophenolate2-Methyl-4-chlorophenoxyacetic acidNITROFEN2,4-Di-tert-butylphenol3-CHLORO-4-PHENOXYANILINEALKYLPHENOL DISULFIDEsynthetic tanning agent No.283-AMINO-1-PHENOXY-2-PROPANOL HYDROCHLORIDE4-Hydroxyvalerophenone3-Phenoxypropionic acidSODIUM PHENOLATE TRIHYDRATE4-Phenoxybutanoic acid2,4,6-Tri-tert-butylphenolAdhesive 706Acid Red 111Roxatidine acetateAntioxidant T502Sulphur Indanthrene Blue RNXBisacodylTri(4-isopropylphenyl) phosphate
- Raw materialsSodium hydroxideSulfuric acid PETROLEUM ETHERSodium sulfateBenzeneSodium sulfiteSulfur dioxidePROPYLENESulfur trioxideCOAL TARFiber Glass WoolIsoproturonBenzenesulfonic acid sodium saltLiquefied petroleum gesPhenol crudeCUMENECumyl hydroperoxide4-Isopropylaniline
- Hydroquinone Sodium benzenolate Benzene 4-Chloro-3-nitroanisole N-(5-Methoxy-2-phenoxyphenyl)methanesulfonamide Iguratimod Impurity 10 Iguratimod N-(4-(2-aminoacetyl)-5-methoxy-2-phenoxyphenyl)methanesulfonamide hydrochloride MethanesulfonaMide, N-[4-[2-(forMylaMino)acetyl]-5-hydroxy-2-phenoxyphenyl]- Iguratimod Impurity 11 Iguratimod Impurity 2 Phenyl methanesulfonate MethanesulfonaMide, N-[4-[2-(forMylaMino)acetyl]-5-Methoxy-2-phenoxyphenyl]- Iguratimod Impurity Iguratimod Impurity 14 Iguratimod Impurity 5 Iguratimod 2-Chloro-5-methoxyaniline
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