Phenol CAS 108-95-2

Introduction：Basic information about Phenol CAS 108-95-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Phenol Basic information

• Product Name: Phenol
• Synonyms: Phenol, water saturated, stabilized;hydroxybenzol;PHENOL, LOOSE CRYSTALS A.C.S. REAGENT;PHENOL - CRYSTALLINE PURE DAB, PH. EUR., USP;PHENOL USP;LIQUEFIEDPHENOL,LIQUEFIED,USP;PHENOL,FUSEDCRYSTAL,BIOTECHGRADE;PHENOL,FUSEDCRYSTAL,TECHNICAL
• CAS: 108-95-2
• MF: C6H6O
• MW: 94.11
• EINECS: 203-632-7
• Product Categories: Chemical Synthesis;Aromatics;Phenol;Aromatics Compounds;Chemistry;Electrophoresis Materials;Bioactive Small Molecules;Building Blocks;C6 to C8;Cell Biology;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Phenols;2000/60/EC;International Standards;NIOSH and OSHA Methods;OSHA 32: Analysis of Phenol in Indoor AirVolatiles/ Semivolatiles;PER - POLAMethod Specific;Alpha Sort;European Community: ISO and DIN;P;P-SAlphabetic;N-PAlphabetic;Molecular Biology;Alphabetical Listings;Flavors and Fragrances;O-P;alcohol;fine chemical;Acids and BasesMolecular Biology;Biochemicals and Reagents;Denaturation;DNA&RNA Purification;Plant Nucleic Acid Purification;Reagents;ReagentsPlant Molecular Biology;Pesticides&Metabolites;PER - POLAEPA;TO-8: Cresol And Phenol By HPLC-UV-EC-FIMethod Specific;EPA TO Methods;108-95-2
• Mol File: 108-95-2.mol

Phenol Chemical Properties

• Melting point: 40-42 °C(lit.)
• Boiling point: 182 °C(lit.)
• bulk density: 620kg/m3
• density: 1.071 g/mL at 25 °C(lit.)
• vapor density: 3.24 (vs air)
• vapor pressure: 0.09 psi ( 55 °C)
• FEMA: 3223 | PHENOL
• refractive index: n20/D 1.53
• Fp: 175 °F
• storage temp.: 2-8°C
• solubility: H₂O: 50 mg/mL at 20 °C, clear, colorless
• form: liquid
• pka: 9.89(at 20℃)
• Specific Gravity: 1.071
• color: faintly yellow
• Odor: Sweet, medicinal odor detectable at 0.06 ppm
• PH: 6.47(1 mM solution);5.99(10 mM solution);5.49(100 mM solution);
• Odor Threshold: 0.0056ppm
• Odor Type: phenolic
• biological source: synthetic
• explosive limit: 1.3-9.5%(V)
• Water Solubility: 8 g/100 mL
• FreezingPoint: 41℃
• Sensitive: Air & Light Sensitive
• Merck: 14,7241
• JECFA Number: 690
• BRN: 969616
• Henry's Law Constant: 1.09 at 5 °C (average derived from six field experiments, Lüttke and Levsen, 1997)
• Exposure limits: TLV-TWA skin 5 ppm (～19 mg/m³ )(ACGIH, MSHA, and OSHA); 10-hour TWA 5.2 ppm (～20 mg/m³ ) (NIOSH); ceiling60 mg (15 minutes) (NIOSH); IDLH 250ppm (NIOSH).
• Dielectric constant: 4.3（10℃）
• Stability: Hygroscopic
• Major Application: agriculture cleaning products cosmetics environmental food and beverages personal care
• Cosmetics Ingredients Functions: PRESERVATIVE ORAL CARE FRAGRANCE DENATURANT ANTIMICROBIAL DEODORANT
• InChI: 1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
• InChIKey: ISWSIDIOOBJBQZ-UHFFFAOYSA-N
• SMILES: Oc1ccccc1
• LogP: 1.47 at 30℃
• CAS DataBase Reference: 108-95-2(CAS DataBase Reference)
• IARC: 3 (Vol. 47, 71) 1999
• NIST Chemistry Reference: Phenol(108-95-2)
• EPA Substance Registry System: Phenol (108-95-2)
• Absorption: cut-off at 294nm in H2O at 0.5M

Safety Information

• 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
• OEB: A
• OEL: TWA: 5 ppm (19 mg/m3), Ceiling: 15.6 ppm (60 mg/m3) [15-minute] [skin]
• WGK Germany: 2
• RTECS: SJ3325000
• F: 8-23
• Autoignition Temperature: 715 °C
• TSCA: TSCA listed
• HazardClass: 6.1
• PackingGroup: II
• HS Code: 29071100
• Storage Class: 3 - Flammable liquids
• Hazard Classifications: Acute Tox. 4 Dermal Acute Tox. 4 Inhalation Acute Tox. 4 Oral Eye Irrit. 2 Flam. Liq. 2
• Hazardous Substances Data: 108-95-2(Hazardous Substances Data)
• Toxicity: LD50 orally in rats: 530 mg/kg (Deichmann, Witherup)
• IDLA: 250 ppm

Phenol Usage And Synthesis

Chemical Properties

Phenol is the simplest member of a class of organic compounds possessing a hydroxyl group attached to a benzene ring or to a more complex aromatic ring system.
Also known as carbolic acid or monohydroxybenzene, phenol is a colorless to white crystalline material of sweet odor, having the composition C6H5OH, obtained from the distillation of coal tar and as a by-product of coke ovens.
Phenol has broad biocidal properties, and dilute aqueous solutions have long been used as an antiseptic. At higher concentrations, it causes severe skin burns; it is a violent systemic poison. It is a valuable chemical raw material for the production of plastics, dyes, pharmaceuticals, syntans, and other products.

Phenol melts at about 43°C and boils at 183°C. The pure grades have melting point of 39°C, 39.5°C, and 40°C. The technical grades contain 82%-84% and 90%-92% phenol. The crystallization point is given as 40.41°C. The specific gravity is 1.066. It dissolves in most organic solvents. By melting the crystals and adding water, liquid phenol is produced, which remains liquid at ordinary temperatures. Phenol has the unusual property of penetrating living tissues and forming a valuable antiseptic. It is also used industrially in cutting oils and compounds and in tanneries. The value of other disinfectants and antiseptics is usually measured by comparison with phenol.

Uses

Phenol 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.

Production

Coal 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.
Cumene method:
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.

Sulfonation method:
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.

Toxicity

Phenol 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.

Description

Phenol is a stable chemical substance and appear as colourless/white crystals with acharacteristic, distinct aromatic/acrid odour. It is reactive and incompatible with strongoxidising agents, strong bases, strong acids, alkalis, and calcium hypochlorite. Phenol isflammable and may discolour in light.Phenol is used in the manufacture or production of explosives, fertiliser, coke, illuminatinggas, lampblack, paints, paint removers, rubber, perfumes, asbestos goods, woodpreservatives, synthetic resins, textiles, drugs, and pharmaceutical preparations. It is alsoextensively used as a disinfectant in the petroleum, leather, paper, soap, toy, tanning, dye,and agricultural industries.

Chemical Properties

Phenol, 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 Properties

Phenol 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 tofood is limited to a role as a flavoring ingredient in a few foods at a maximum level below 10 ppm.

Physical properties

Phenol is a colorless or white crystalline solid that is slightly soluble in water. Phenol is thesimplest of the large group of organic chemicals known as phenols, which consist of compoundswhere a carbon in the phenyl aromatic group (C6H5) is directly bonded to hydroxyl,OH.

Occurrence

It 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, cassialeaf, 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, truffleand Chinese quince.

History

Phenol’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 couldbe surgically treated.A broken bone piercing the skin, which today is a painful but notlife-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 beganto use antiseptic methods during routine surgery during the 1860s.

Uses

The 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.

Uses

Phenol 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).

Uses

phenol 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.

Definition

ChEBI: An organic hydroxy compound that consists of benzene bearing a single hydroxy substituent. The parent of the class of phenols.

Production Methods

Historically, phenol was produced by the distillation of coal tar.Today, phenol is prepared by one of several synthetic methods, suchas the fusion of sodium benzenesulfonate with sodium hydroxidefollowed by acidification; the hydrolysis of chlorobenzene by dilutesodium hydroxide at high temperature and pressure to give sodiumphenate, which on acidification liberates phenol (Dow process); orthe catalytic vapor-phase reaction of steam and chlorobenzene at500°C (Raschig process).

Definition

1. (carbolic acid,hydroxybenzene, C₆H₅OH) A white crystallinesolid used to make a variety of otherorganic compounds.
2. A type of organic compound in which atleast one hydroxyl group is bound directlyto one of the carbon atoms of an aromaticring. Phenols do not show the behaviortypical of alcohols. In particular they aremore acidic because of the electron-withdrawingeffect of the aromatic ring. Thepreparation of phenol itself is by fusing thesodium salt of the sulfonic acid withsodium hydroxide:
C₆H₅SO₂.ONa + 2NaOH → C₆H₅ONa
+ Na₂SO₃ + H₂O
The phenol is then liberated by sulfuricacid:
2C₆H₅ONa + H₂SO₄ → 2C₆H₅OH +Na₂SO₄
Reactions of phenol include:
1. Replacement of the hydroxyl group witha chlorine atom using phosphorus(V)chloride.
2. Reaction with acyl halides to form estersof carboxylic acids.3. Reaction with haloalkanes under alkalineconditions to give mixed alkyl–arylethers.
In addition phenol can undergo furthersubstitution on the benzene ring. The hydroxylgroup directs other substituentsinto the 2- and 4-positions.

Production Methods

Phenol 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.

Indications

Phenol in dilute solution (0.5% to 2%) decreases itch by anesthetizing the cutaneousnerve endings. Phenol should never be used on pregnant women or infants youngerthan 6 months of age.

Preparation

Phenol is formed in dry distillation of wood, peat and coal; coal tar is one of the commercial sources of phenol and itshomologues.

World Health Organization (WHO)

Phenol became widely used as an antiseptic followingdemonstration of its germicidal activity in 1867. It is an intensely corrosivesubstance and percutaneous absorption can produce serious systemic toxicity. Ithas been withdrawn from pharmaceutical preparations by at least one nationalregulatory authority. However, it is still used widely in concentrations of the orderof 1.4% in proprietary preparations for the relief of soreness of the mouth andthroat.

Aroma threshold values

Detection: 5.5 ppm. Aroma characteristics at 1.0%: medicinal, creosote, smoky, spicy, phenolic, leatherlikewith notes of fried meat and coffee.

Taste threshold values

Taste characteristics at 3 ppm: spicy, phenolic, tobacco, musty, woody, medicinal, smoky, tarlike andslightly 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 Description

A 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 Reactions

Decomposes slowly in air. Mixtures of 9-10% phenol in air are explosive. Soluble in water

Reactivity Profile

PHENOL 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 Hazard

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.
https://ehs.ucsc.edu/lab-safety-manual/specialty-chemicals/phenol.html

Fire Hazard

Flammable 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 Explosibility

Phenol is a combustible solid (NFPA rating = 2). When heated, phenol producesflammable vapors that are explosive at concentrations of 3 to 10% in air. Carbondioxide or dry chemical extinguishers should be used to fight phenol fires.

Pharmaceutical Applications

Phenol is used mainly as an antimicrobial preservative in parenteralpharmaceutical products. It has also been used in topicalpharmaceutical formulations and cosmetics;
Phenol is widely used as an antiseptic, disinfectant, andtherapeutic agent, although it should not be used to preservepreparations that are to be freeze-dried.

Industrial uses

Phenol 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.

Biochem/physiol Actions

Phenol?has the ability to denature protein, hence can lead to denervation. At lower concentration, it can serve as a local anaesthetic and can also act as a neurolytic agent in higher concentration. It is also linked with tissue damage at higher concentrations.

Safety

Phenol is highly corrosive and toxic, the main effects being on thecentral nervous system. The lethal human oral dose is estimated tobe 1 g for an adult.
Phenol is absorbed from the gastrointestinal tract, skin, andmucous membranes, and is metabolized to phenylglucuronide andphenyl sulfate, which are excreted in the urine.
Although there are a number of reports describing the toxiceffects of phenol, these largely concern instances of accidentalpoisoning or adverse reactions during its use as a therapeuticagent.Adverse reactions associated with phenol used as apreservative are less likely owing to the smaller quantities that areused; however, it has been suggested that the body burden of phenolshould not exceed 50 mg in a 10-hour period.This amount couldbe exceeded following administration of large volumes of phenolpreservedmedicines.
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 Exposure

Phenol 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.

Carcinogenicity

Phenol 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.

Source

Detected 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 fuelA (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 fromSwitzerland, 3 from Boston, MA). At 25 °C, phenol concentrations ranged from 63 to 130,000μg/L in gasoline and from 150 to 1,500 μg/L in water-soluble fractions. Average concentrationswere 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 fromGainesville, FL with individual fractions of three individual petroleum products at 24–25 °C for24 h. The aqueous phase was analyzed for organic compounds via U.S. EPA approved test method625. 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’swort, European pennyroyal, tomatoes, white mulberries, tobacco leaves, benneseed, sesame seeds,tamarind, white sandlewood, patchouli leaves, rue, slash pine, bayberries, Scotch pine, andtarragon (Duke, 1992).
A liquid swine manure sample collected from a waste storage basin contained phenol at aconcentration of 22.0 mg/L (Zahn et al., 1997).
Schauer et al. (2001) measured organic compound emission rates for volatile organiccompounds, gas-phase semi-volatile organic compounds, and particle phase organic compoundsfrom the residential (fireplace) combustion of pine, oak, and eucalyptus. The gas-phase emissionrates of phenol were 525 mg/kg of pine burned, 300 mg/kg of oak burned, and 434 mg/kg ofeucalyptus 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 20mg/L was recommended (U.S. EPA, 2000).

Environmental fate

Biological. Under methanogenic conditions, inocula from a municipal sewage treatment plantdigester degraded phenol to carbon dioxide and methane (Young and Rivera, 1985).Chloroperoxidase, a fungal enzyme isolated from Caldariomyces fumago, reacted with phenolforming 2- and 4-chlorophenol, the latter in a 25% yield (Wannstedt et al., 1990). In activatedsludge, 41.4% mineralized to carbon dioxide after 5 d (Freitag et al., 1985). When phenol wasstatically incubated in the dark at 25 °C with yeast extract and settled domestic wastewaterinoculum, significant biodegradation with rapid adaptation was observed. At concentrations of 5and 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 anaerobicconditions (Baker and Mayfield, 1980).
Soil. Loehr and Matthews (1992) studied the degradation of phenol in different soils underaerobic 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 usingkaolinite 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 inharbor 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 s