Biphenyl Property

Melting point:

68-70 °C (lit.)

Boiling point:

255 °C (lit.)

Density 

0.992

vapor density 

5.31 (vs air)

vapor pressure 

9.46 mm Hg ( 115 °C)

refractive index 

1.475

FEMA 

3129 | BIPHENYL

Flash point:

113 °C

storage temp. 

Store below +30°C.

solubility 

Soluble in alcohol and ether

form 

Crystalline Powder, Crystals or Flakes

color 

White to faint yellow

Specific Gravity

0.992

Odor

pleasant odor

Odor Type

green

explosive limit

0.6%, 111°F

Water Solubility 

insoluble

JECFA Number

1332

Merck 

14,3314

BRN 

1634058

Henry's Law Constant

2.92 at 25 °C (air stripping-GC, Destaillats and Charles, 2002)

Exposure limits

NIOSH REL: TWA 0.2 ppm, IDLH 100 mg/m3; OSHA PEL: TWA 0.2 ppm; ACGIH TLV: TWA 0.2 ppm.

Dielectric constant

20.0（Ambient）

Stability:

Stable. Combustible. Incompatible with strong oxidising agents.

InChIKey

ZUOUZKKEUPVFJK-UHFFFAOYSA-N

LogP

4.008 at 25℃

CAS DataBase Reference

92-52-4(CAS DataBase Reference)

NIST Chemistry Reference

Biphenyl(92-52-4)

EPA Substance Registry System

Biphenyl (92-52-4)

Safety

Hazard Codes 

Xi,N,Xn,F,T

Risk Statements 

36/37/38-50/53-67-65-62-48/20-11-39/23/24/25-23/24/25-52/53

Safety Statements 

23-60-61-62-36/37-33-29-16-9-45

OEB

C

OEL

TWA: 1 mg/m3 (0.2 ppm)

RIDADR 

UN 3077 9/PG 3

WGK Germany 

2

RTECS 

DU8050000

Autoignition Temperature

570 °C

TSCA 

Yes

HazardClass 

9

PackingGroup 

III

HS Code 

29029030

Hazardous Substances Data

92-52-4(Hazardous Substances Data)

Toxicity

LD50 orally in rats: 3280 mg/kg (Deichmann)

IDLA

100 mg/m3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P273Avoid release to the environment.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Biphenyl Chemical Properties,Usage,Production

description

Biphenyl is also called phenyl benzene, it is formed by two connected phenyl compounds, is white or colorless to light yellow crystal plate, industrial products is slightly yellow with special fragrance. The melting temperature is 69.2 ℃, boiling point is 69.2 ℃. Insoluble in water, but soluble in organic solvents. Commonly used for organic synthesis precursor, is one of the key components of the organic high temperature heating medium. Its derivatives include benzidine, diphenyl ether, eight bromine diphenyl ether, polychlorinated biphenyls, etc.

Natural biphenyl exists in coal tar, crude oil and natural gas, the mass fraction is 0.20% to 0.20% in coal tar, current preparation methods of biphenyl include coal tar extraction and chemical synthesis.
The chemical bond in the middle of biphenyls can rotate freely, but if there were bulky groups in the four orthos, restricts rotation and would produce resistance isomer. This type of compounds (such as BINAP) can be used as a chiral ligands. substituted biphenyl by Suzuki reaction and Ullmann coupling reactions.
Biphenyl is a kind of important organic raw materials, widely used in medicine, pesticides, dyes, liquid crystal materials, etc. Can be used in the synthesis of plasticizer, preservatives, can also be used to make fuel, engineering plastic and high energy fuel.

Chemical Properties

Biphenyl is a white or slightly yellow scaly crystal, has a unique fragrance. Insoluble in water, acid and alkali, soluble in alcohol, ether, benzene and other organic solvents.

Reactions

Biphenyl is a neutral molecule and fairly non-reactive due to lack of functional group. However, biphenyl participates in many of the reactions that are typical for benzene, for example, substitution reactions upon treatment with halogens in the presence of a Lewis acid. Also, it is required to convert biphenyls into the structural analogs containing the active groups in order for it to be able to use for synthetic intermediate for the production of a host of other organic compounds such as emulsifiers, optical brighteners, crop protection products, plastics and pharmaceuticals (Johansson and Olsen, 2008). For this, it is important to consider the o,p-directing and/or mdirecting effect, especially when substitution at a specific position is desired i.e. mono, di-, tri- or tetra- substitutions. It is possible to acetylate the carboxylic part, also various other biphenyl derivative synthesis are possible by carrying out the amination, halogenation, sulphonation, alkylation, hydroxylation, metal complexation etc.

Uses

Biphenyl is used in organic syntheses, heat transfer fluids, dye carriers, food preservatives, as an intermediate for polychlorinated biphenyls, and as a fungistat in the packaging of citrus fruits.
Biphenyl with high thermal stability and low vapor pressure, long often alone or with diphenyl ether and blend to used as heating medium. Component of biphenyl and terphenyl (including Biphenyl 13%, terphenyl 61%) can effectively absorb radiation, can be used as a heating medium for nuclear power plant. And three terphenyl([91-94-4]) is the byproduct of benzene pyrolysis to produce Biphenyl, according to the different reaction conditions, the proportion of the reaction product of biphenyl and terphenyl within a certain range of change, in general, Biphenyl: terphenyl=78:1. Biphenyl is used as a carrier, and its derivatives of ethyl biphenyl, diethyl biphenyl and triethyl biphenyl senior can be used as solvents, used in pressure sensitive dye solvent of carbon paper.

Production Method

Biphenyl occurs naturally in coal tar, crude oil, and natural gas and can be isolated from these sources via distillation. It can also be synthesized synthetically by using a Grignard reagent such as phenylmagnesium bromide and reacting it with bromobenzene, reacting fluorobenzene with phenyl lithium or reacting benzyne with phenyl lithium as follows.
Ullmann et al. (1904), discovered that heating iodobenzene with a copper powder catalyst leads to the formation of biphenyl with high purity. Meanwhile, this reaction has become a textbook case and it is widely used in synthetic chemistry due to its versatility in the association of substituted phenyls to complex biphenyl derivatives.
The synthesis of biphenyl out of iodobenzene on copper essentially consists of three steps: dissociation of iodobenzene (C6H5I) to phenyl (C6H5) and iodine, diffusion of phenyl to find another phenyl as a reaction partner, and association to form biphenyl (C12H10). The dissociation of iodobenzene by thermal activation takes place at 180 K and biphenyl is formed at 210 K for multilayer (Weiss et al., 1998) and 300 K for submonolayer iodobenzene on Cu(III) [Yang et al., 1995; Xi and Bent, 1992].

Toxicity

Biphenyls are low toxic and irritating to humans. Its steam can stimulate eyes, nose and trachea, cause loss of appetite and vomiting, and has certain toxicity to the nervous system, digestive system and kidney. The oral LD50 of rats was 3.28g/kg. The maximum allowable concentration in the workplace is > 1mg / m3 (coexisting with diphenyl ether). It can stimulate, damage the heart, liver and kidney, and have toxic effects on the reproductive system of humans and other animals. This product has stimulating effect and damages myocardium, liver and kidney. LD50: 3280mg / kg in rats (25% olive oil solution) and 240mg / kg in rabbits. It exists in flue-cured tobacco, oriental tobacco and flue gas.

Toxicity

ADI 0~0.05 mg/kg (under some conditions 0.05~0.25 mg/kg FAO/WHO, 2001).
LD50 3.28~5.04 g/kg (mice, through the mouth).

Limited use

FAO/WHO, the United States and Canada regulations, its residual ≤110 mg/kg or less; Japan, France, Germany, the Netherlands, rules ≤70 mg/kg or less.

Preparation

High temperature coal tar contains about 3.0% biphenyl, which can be recovered from washing oil fraction. In 1926, Dow Chemical Company of the United States began to produce biphenyl by pyrolysis of benzene. Another source of biphenyl is the by-product of thermal dealkylation of toluene to benzene. With the development of this process, the byproduct biphenyl of this process has gradually become the main source of biphenyl. In the laboratory, the diazonium salt obtained by diazotization of aniline is added to benzene, and then the mixture is slowly added to sodium hydroxide solution, stirred for reaction, and the temperature slowly rises from below 5 ℃ to 30-35 ℃. Biphenyl is formed after reaction for 8 hours.

Description

Biphenyl is an organic compound with chemical formula of C12H10. It is a white crystalline powder, insoluble in water, soluble in ether, ethanol, carbon tetrachloride, dioxane, aromatic hydrocarbons, etc. it is mainly used as solvent, heat transfer agent, fruit mildew inhibitor and organic synthesis.

Description

Biphenyl, also called diphenyl, consists of two benzene rings joined by a single bond. It exists as colorless to yellowish crystals, has a distinctive odor, and occurs naturally in oil, natural gas, and coal tar.

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 fluids.

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).

Uses

Biphenyl is used to prevent fungal attack on stored citrus fruit. It is impregnated into fruit wraps.

Uses

As heat transfer agent; fungistat for oranges (applied to inside of shipping container or wrappers); in organic syntheses.

Uses

Biphenyl is used as an antifungal agent to preserve citrus fruit, in citrus wrappers to retard mold growth, in heat transfer fluids, in dye carriers for textiles and copying paper, as a solvent in pharmaceutical production, in optical brighteners, and as an intermediate for the production of a wide range of organic compounds.

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.

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.

Preparation

By thermal dehydrogenation of benzene.

Aroma threshold values

Detection: 0.5 ppb

Synthesis Reference(s)

Journal of the American Chemical Society, 83, p. 1251, 1961 DOI: 10.1021/ja01466a056
Tetrahedron Letters, 25, p. 391, 1984 DOI: 10.1016/S0040-4039(00)99891-5

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.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Biphenyl is incompatible with oxidizers.

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

Fire Hazard

Combustible. Emits toxic fumes under fire conditions.

Flammability and Explosibility

Non flammable

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

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.

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least 15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Do not induce vomiting.

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.

storage

1,1’-Biphenyl should be kept stored in tightly closed containers in a cool, dry, isolated, and properly ventilated area, away from heat, sources of ignition, incompatibles, and contact with strong oxidizers.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1—Poisonous materials, Technical Name Required.

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.

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.

Precautions

Occupational workers should be careful during use and chemical management because the fi nely dispersed particles of 1,1’-biphenyl form explosive mixtures in air