ChemicalBook > Product Catalog > Organic Chemistry > Hydrocarbons and derivatives > Aromatic hydrocarbons > Biphenyl
Basic information description Chemical Properties Reactions Uses Production Method Toxicity Limited use Safety Related Supplier
Biphenyl Chemical Properties
- 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)
- FEMA 3129 | BIPHENYL
- refractive index 1.475
- Flash point:113 °C
- storage temp. 0-6°C
- solubility Soluble in alcohol and ether
- form Crystalline Powder, Crystals or Flakes
- Specific Gravity0.992
- color White to faint yellow
- Odorpleasant odor
- explosive limit0.6%, 111°F
- Water Solubility insoluble
- Merck 14,3314
- JECFA Number1332
- BRN 1634058
- Henry's Law Constant2.92 at 25 °C (air stripping-GC, Destaillats and Charles, 2002)
- Exposure limitsNIOSH REL: TWA 0.2 ppm, IDLH 100 mg/m3; OSHA PEL: TWA 0.2 ppm; ACGIH TLV: TWA 0.2 ppm.
- Stability:Stable. Combustible. Incompatible with strong oxidising agents.
- CAS DataBase Reference92-52-4(CAS DataBase Reference)
- NIST Chemistry ReferenceBiphenyl(92-52-4)
- EPA Substance Registry SystemBiphenyl (92-52-4)
- 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
- RIDADR UN 3077 9/PG 3
- WGK Germany 2
- RTECS DU8050000
- Autoignition Temperature570 °C
- TSCA Yes
- HazardClass 9
- PackingGroup III
- HS Code 29029030
- Hazardous Substances Data92-52-4(Hazardous Substances Data)
- ToxicityLD50 orally in rats: 3280 mg/kg (Deichmann)
Biphenyl Usage And Synthesis
- descriptionBiphenyl 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 PropertiesBiphenyl 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.
- ReactionsBiphenyl 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.
- UsesBiphenyl 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 MethodBiphenyl 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].
- ToxicityADI 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 useFAO/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.
- DescriptionBiphenyl, 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 Properties1,1'-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 propertiesWhite scales with a pleasant but peculiar odor. Odor threshold concentration is 0.83 ppb (quoted, Amoore and Hautala, 1983).
- OccurrenceReported 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).
- UsesBiphenyl is used to prevent fungal attack on stored citrus fruit. It is impregnated into fruit wraps.
- UsesBiphenyl 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.
- UsesAs heat transfer agent; fungistat for oranges (applied to inside of shipping container or wrappers); in organic syntheses.
- DefinitionAn organic compound having a structure in which two phenyl groups are joined by a C–C bond.
- DefinitionChEBI: 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.
- PreparationBy thermal dehydrogenation of benzene.
- Aroma threshold valuesDetection: 0.5 ppb
- General DescriptionA 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 ReactionsInsoluble in water.
- Reactivity ProfileBiphenyl is incompatible with oxidizers.
- Health HazardExposures 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 HazardCombustible. Emits toxic fumes under fire conditions.
- Safety ProfilePoison 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 ExposureBiphenyl is a fungicide (pesticide). It is also used as a heat transfer agent, dye carrier, and as an intermediate in organic synthesis.
- SourcePresent 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 FateBiological. 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 pathwayBiphenyl 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.
- storage1,1’-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.
- ShippingUN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1—Poisonous materials, Technical Name Required.
- Purification MethodsCrystallise 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.]
- DegradationBiphenyl is not subject to hydrolysis.
- IncompatibilitiesMist 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 DisposalDissolve 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.
- PrecautionsOccupational workers should be careful during use and chemical management because the fi nely dispersed particles of 1,1’-biphenyl form explosive mixtures in air
Biphenyl Preparation Products And Raw materials
- Raw materialsEtanolSodiumBenzeneBromobenzeneCOAL TARPolishing oil
- Preparation ProductsNaphthalene6-BROMO-4-CHLOROQUINOLINEBromadiolone2-Methyl-3-biphenylmethanolfluorescent whitening agent ATS-X2-PhenylphenolEstradiol4-AMINOBIPHENYLα-phenyl-2-p-tolylethylamine2-Phenylindolep-Terphenyl6-bromoquinolin-4(3H)-one4-Biphenylcarboxylic acid4-Phenylphenol6-CHLORO-2-(CHLOROMETHYL)-3-OXIDO-4-PHENYL-QUINAZOLINEbrotianide 3-(4'-Bromo[1,1'-biphenyl]-4-yl)-1,2,3,4-tetrahydro-1-naphthalenol4-Bromobiphenyl2-(2-AMINO-4-BIPHENYL)PROPIONITRILEBitertanolpolyquinoxaline4-BENZYLBIPHENYLRaloxifene4-(chlorophenylmethyl)-1,1'-biphenyl 4-Acetylbiphenyl3-[1,1'-Biphenyl]-4-yl-1,2,3,4-tetrahydro-1-naphthol4-BIPHENYLSULFONYL CHLORIDE4,4'-BIS(BROMOMETHYL)BIPHENYL4,4'-Bis(chloromethyl)-1,1'-biphenyl4,4'-DiacetylbiphenylBifonazole4-BenzoylbiphenylFenbufen
- 2,2',3,5'-TETRACHLOROBIPHENYL Bromobenzene OCTYLPHENYLPOLYETHYLENE GLYCOL Phenylacetone Diphenyl carbonate 2-Phenylphenol Dichloromethylphenylsilane (FORMYLMETHYLENE)TRIPHENYLPHOSPHORANE Potassium hydrogen phthalate Bis(2-ethylhexyl) phthalate m-Phenylenediamine Phthalic acid Isophthalic acid 4-Methoxyphenylacetone 4-Nitrophenyl chloroformate Benzophenone 4-Biphenylcarboxylic acid Triphenylphosphine
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