Chemical Properties
1,1’-Biphenyl is a clear colorless liquid with a pleasant odor and stable organic compound.
It is combustible at high temperatures, producing carbon dioxide and water when combustion is complete. Partial combustion produces carbon monoxide, smoke, soot, and low molecular weight hydrocarbons. It is used extensively in the production of heat-transfer
fl uids, for example, as an intermediate for polychlorinated biphenyls, and dye carriers for
textile dyeing. It is also used as a mold retardant in citrus fruit wrappers, in the formation
of plastics, optical brighteners, and hydraulic fl ui
General Description
A clear colorless liquid with a pleasant odor. Flash point 180°F. Insoluble in water. Vapors are heavier than air. Used to manufacture other chemicals and as a fungicide.
Reactivity Profile
BIPHENYL(92-52-4) is incompatible with oxidizers.
Air & Water Reactions
Insoluble in water.
Health Hazard
CALL FOR MEDICAL AID. VAPOR, MIST OR DUST: Irritating to eyes, nose, throat and skin. Flush affected area with plenty of water. IF IN EYES, hold eyelids open and flush with plenty of water. SOLID OR LIQUID: Irritating to skin and eyes, nose and throat. Remove contaminated clothing and shoes. Flush affected areas with plenty water. IF IN EYES, hold eyelids open and flush with plenty of water. If swallowed, do not induce vomiting. Harmful if inhaled or swallowed. Causes irritation to eyes, skin and mucous membrane and upper respiratory tract. Causes central nervous system depression, paralysis and convulsion in animals. May cause headache, diffuse gastrointestinal pain, nausea, indigestion, numbness and aching of limbs, and general fatigue. Liver function test may show abnormalities. Chronic exposure is mostly characterized by central nervous system symptoms, fatigue, headache, tremor, insomnia, sensory impairment, and mood changes. Such symptoms are rare however.
Health Hazard
Exposures to 1,1’-biphenyl cause acute effects with symptoms that include, but are not
limited to, polyuria, accelerated breathing, lacrimation, anorexia, weight loss, muscular
weakness, coma, fatty liver cell degeneration, and severe nephrotic lesions. Exposure to
biphenyl fumes for short periods of time causes nausea, vomiting, irritation of the eyes
and respiratory tract, and bronchitis. Breathing small amounts of 1,1’-biphenyl over long
periods of time causes damage to the liver and the nervous system of exposed workers.
Breathing the mists, vapors, or fumes may irritate the nose, throat, and lungs. Depending
on the concentration and duration of exposure, the symptoms include, but are not limited
to, sore throat, coughing, labored breathing, sneezing, a burning sensation, and the effects
of CNS depression. Symptoms may include headache, excitation, euphoria, dizziness,
incoordination, drowsiness, light-headedness, blurred vision, fatigue, tremors, convulsions, loss of consciousness, coma, respiratory arrest, and death, depending on the concentration and duration of exposure
Potential Exposure
Biphenyl is a fungicide (pesticide). It
is also used as a heat transfer agent, dye carrier, and as an
intermediate in organic synthesis.
Fire Hazard
Combustible. Emits toxic fumes under fire conditions.
First aid
Move victim to fresh air. Call 911 or emergency
medical service. Give artificial respiration if victim is not
breathing. Do not use mouth-to-mouth method if victim
ingested or inhaled the substance; give artificial respiration
with the aid of a pocket mask equipped with a one-way valve
or other proper respiratory medical device. Administer oxygen
if breathing is difficult. Remove and isolate contaminated
clothing and shoes. In case of contact with substance,
immediately flush skin or eyes with running water for at
least 20 minutes. For minor skin contact, avoid spreading
material on unaffected skin. Keep victim warm and quiet.
Effects of exposure (inhalation, ingestion or skin contact) to
substance may be delayed. Ensure that medical personnel
are aware of the material(s) involved and take precautions to
protect themselves. Medical observation is recommended
for 24 to 48 hours after breathing overexposure, as pulmonary
edema may be delayed. As first aid for pulmonary
edema, a doctor or authorized paramedic may consider
administering a drug or other inhalation therapy.
Shipping
UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1—Poisonous materials, Technical
Name Required.
Incompatibilities
Mist may form explosive mixture with
air. 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.
Waste Disposal
Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator
equipped with an afterburner and scrubber. All federal, state,
and local environmental regulations must be observed.
Physical properties
White scales with a pleasant but peculiar odor. Odor threshold concentration is 0.83 ppb (quoted,
Amoore and Hautala, 1983).
Occurrence
Reported found in coal tar, bilberry, carrots, peas, potato, bell pepper, rum, cocoa, tomato, coffee, roasted
peanuts, olive (Olea europae), buckwheat and tamarind (Tamarindus indica L).
Application
Biphenyl is an important organic raw material, which is widely used in medicine, pesticide, dye, liquid crystal materials and other fields. It can be used to synthesize plasticizers and preservatives, and can also be used to manufacture fuels, engineering plastics and high-energy fuels. Biphenyls are found in coal tar, crude oil and natural gas. The preparation methods of biphenyl include chemical synthesis of biphenyl by pyrolysis of benzene and separation and extraction of biphenyl from various coal tar oil fractions. The mass fraction of biphenyl in coal tar is 0.20% - 0.40%. Coal tar extraction and chemical synthesis coexist. Biphenyl is combustible. In case of high temperature, open fire and oxidant, it is dangerous to burn. It should be stored in a cool and ventilated warehouse away from kindling and heat source. It should be stored separately from oxidants and strong acids. It should be loaded and unloaded gently to keep the package intact. Biphenyl is used as heat exchanger and impregnator of fruit packaging paper. Biphenyl can be used in organic synthesis. Biphenyl is the raw material of engineering plastics polysulfone. It is used to prepare Trichlorobenzene and pentachlorophenyl. Biphenyl is used as heat carrier, preservative, dye and so on. Biphenyl is used as a reference material for chromatographic analysis. Biphenyl is the intermediate of rodenticides rodenticide modek and bromadine, and it is an organic carrier with good performance.
Definition
An organic compound having a structure
in which two phenyl groups are joined by a
C–C bond.
Definition
ChEBI: A benzenoid aromatic compound that consists of two benzene rings connected by a single covalent bond. Biphenyl occurs naturally in coal tar, crude oil, and natural gas. Formerly used as a fungicide for citrus crops.
Preparation
By thermal dehydrogenation of benzene.
Aroma threshold values
Detection: 0.5 ppb
Flammability and Explosibility
Nonflammable
Safety Profile
Poison by intravenous route.Moderately toxic by ingestion. A powerful irritant byinhalation in humans. Human systemic effects byinhalation of very small amounts: flaccid paralysis, nauseaor vomiting, and other unspecified gastrointestinal effects.Que
Source
Present in coal tar at a concentration of 2.72 mg/g (Lao et al., 1975). Detected in woodpreserving
creosotes at a concentration of 2.1 wt % (Nestler, 1974). Typical concentration of
biphenyl in a heavy pyrolysis oil is 2.3 wt % (Chevron Phillips, May 2003).
Environmental Fate
Biological. Reported biodegradation products include 2,3-dihydro-2,3-dihydroxybi phenyl, 2,3-dihydroxybiphenyl, 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate, 2-hydroxy-
3-phenyl-6-oxohexa-2,4-dienoate, 2-oxopenta-4-enoate, phenylpyruvic acid (Verschueren,
1983), 2-hydroxybiphenyl, 4-hydroxybiphenyl and 4,4′-hydroxybiphenyl (Smith and
Rosazza, 1974). Under aerobic conditions, Beijerinckia sp. degraded biphenyl to cis-2,3-
dihydro-2,3-dihydroxybiphenyl. In addition, Oscillatoria sp. and Pseudomonas putida
degraded biphenyl to 4-hydroxybiphenyl and benzoic acid, respectively (Kobayashi and
Rittman, 1982). The microbe Candida lipolytica degraded biphenyl into the following
products: 2-, 3- and 4-hydroxybiphenyl, 4,4′-dihydroxybiphenyl and 3-methoxy-4-hydrox ybiphenyl (Cerniglia and Crow, 1981). With the exception of 3-methoxy-4-hydroxybiphe nyl, these products were also identified as metabolites by Cunninghanella elegans (Dodge
et al., 1979). In activated sludge, 15.2% mineralized to carbon dioxide after 5 days (Freitag
et al., 1985).
Photolytic. A carbon dioxide yield of 9.5% was achieved when biphenyl adsorbed on
silica gel was irradiated with light (λ >290 nm) for 17 hours. Irradiation of biphenyl (λ >300 nm) in the presence of nitrogen monoxide resulted in the formation of
Chemical/Physical. The aqueous chlorination of biphenyl at 40°C over a pH range of
6.2 to 9.0 yielded o-chlorobiphenyl and m-chlorobiphenyl (Snider and Alley, 1979). In an
acidic aqueous solution (pH 4.5) containing bromide ions and a chlorinatin
Biphenyl will not hydrolyze since it has no hydrolyzable functional group.
Metabolic pathway
Biphenyl is a stable compound. It has a restricted use as a fungistat
applied to citrus packing material. This has generated studies on its
toxicity and metabolism in mammals and residue studies in stored fruit.
Only limited information on its environmental fate has been published.
Purification Methods
Crystallise biphenyl from EtOH, MeOH, aqueous MeOH, pet ether (b 40-60o) or glacial acetic acid. Free it from polar impurities by passage through an alumina column in *benzene, followed by evaporation. The residue has been purified by distillation in a vacuum and by zone refining. Treatment with maleic anhydride removes anthracene-like impurities. It has been recrystallised from EtOH followed by repeated vacuum sublimation and passage through a zone refiner. [Taliani & Bree J Phys Chem 88 2351 1984, Beilstein 5 H 576, 5 I 271, 5 II 479, 5 III 1726, 5 IV 1807.]
Degradation
Biphenyl is not subject to hydrolysis.
