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Home > Encyclopedia > 2,3′,4,4′,5,5′-Hexachlorobiphenyl

2,3′,4,4′,5,5′-Hexachlorobiphenyl

2,3′,4,4′,5,5′-Hexachlorobiphenyl structure

2,3′,4,4′,5,5′-Hexachlorobiphenyl 

structure
  • CAS No:

    52663-72-6

  • Formula:

    C12H4Cl6

  • Chemical Name:

    2,3′,4,4′,5,5′-Hexachlorobiphenyl

  • Synonyms:

    1,1′-Biphenyl,2,3′,4,4′,5,5′-hexachloro-;2,3′,4,4′,5,5′-Hexachloro-1,1′-biphenyl;2,4,5,3′,4′,5′-Hexachlorobiphenyl;2,3′,4,4′,5,5′-Hexachlorobiphenyl;2′,3,4,4′,5,5′-Hexachlorobiphenyl;PCB 167;CB 167;2,3′,4,4′,5,5′-HxCB

  • Categories:

    Analytical Chemistry  >  Food Safety

Description

2,3',4,4',5,5'-Hexachlorobiphenyl is a trichlorobenzene and a hexachlorobiphenyl.

2,3′,4,4′,5,5′-Hexachlorobiphenyl Basic Attributes

360.88

360.88

HD4MZI40CH

DTXSID7074165

2903999090

Characteristics

0

6.87

1.6±0.1 g/cm3

115.76°C (estimate)

416.0±40.0 °C at 760 mmHg

207.9±24.7 °C

1.627

6.17e-09 M|Solubility in water is extremely low. ... Soluble in oils and organic solvents.

PCB material should be stored in closed containers, in ventilated areas /SRP: With appropriate air pollution control equipment./

167.3 Ų [M-Cl+O]-

... The accuracy of a method based on capillary gas chromatography for estimating vapor pressure of nonpolar compounds was tested by comparing vapor pressures measured by gas chromatography with literature values for the subcooled liquid. Two 1.0 m long fused silica columns were used, a poly(dimethylsiloxane) bonded phase column (BP-1) and a WCOT hydrocarbon phase column (Apolane-87). Gas chromatography measurements were carried out by using n(no)-C18 and n-C20 hydrocarbons as vapor pressure reference compounds. ... The gas chromatography method was applied to 30 polychlorinated biphenyl isomerids containing 1-7 chlorines. The average vapor pressure decreased by a factor of 4.5 for each chlorine added to the biphenyl core, although large differences in vapor pressure were measured for isomers of a particular chlorination level. ...|A generator column technique was used to directly determine log Kow (1-octanol/water partition coefficient) values for 15 polychlorinated biphenyl (PCB) cogeners and biphenyl. The method circumvented many experimental difficulties encountered with the traditional shake-flask system. Log Kow values generated by this procedure were compared with data obtained from the shake-flask method, 2 chromatographic estimation techniques and the computational method of Hansch and Leo. ...

Safety Information

PCB's are chemically very inert and are stable to conditions of hydrolysis and oxidation in industrial use.

P260, P273, P314, P391, P501

H373

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|EXPERIMENTS ON THE COMBUSTION OF POLYCHLORINATED BIPHENYLS (PCB) IN 1 M-LONG TUBE FURNACE INDICATED THAT PCB CONTAINING APPROX 40% CL IS DESTROYED WITHIN 3-4 MIN AT 900-1000 °C USING 100% EXCESS AIR. TEMPERATURES GREATER THAN 1000 °C ARE REQUIRED TO DESTROY PCB CONTAINING APPROX 60% CL & DISTILLATION RESIDUES ARISING FROM PCB MFR. DOMESTIC WASTE INCINERATORS OPERATING AT 800-900 °C ARE UNLIKELY TO PROVE SUITABLE FOR INCINERATING WASTE CONTAINING TRACE AMT OF PCB. PYROLYSIS EXPERIMENTS AT 900 °C WITH NOMINAL RESIDENCE TIME OF 3.5 SEC GAVE 40-60% RECOVERY OF CL AS HCL FROM PCB.|POLYCHLORINATED BIPHENYLS CAN BE DESTROYED BY INCINERATION IF THE TRANSIT TIME IS LONG ENOUGH. DURING INCINERATION HEXACHLOROBENZENE IS FORMED; ITS RATE OF FORMATION INCR AT HIGH TEMP. IN ORDER FOR THE HEXACHLOROBENZENE TO BE DESTROYED, A TEMP OF 950 °C IS NEEDED. THIS RESULTS IN THE FORMATION OF A RESIDUE LESS THAN 100 MG OF HEXACHLOROBENZENE/KG. AT 800 °C & A TRANSIT TIME OF 2 SEC, A RESIDUE OF ABOUT 1200 MG/KG REMAINS.|Investigations were conducted of new and emerging technologies for the disposal of hazardous wastes, ... including molten salt combustion, fluidized bed incineration, high energy electron treatment of trace organic compounds in aqueous solution, the catalyzed wet oxidation of toxic chemicals, dehalogenation of compounds by treatment with ultraviolet (UV) light and hydrogen, UV/chlorinolysis of organics in aqueous solution, the catalytic hydrogenation-dechlorination of polychlorinated biphenyls (PCBs), and ultraviolet-ozone destruction. Theory, specific wastes treated, and economics are discussed. The major technologies investigated in detail were molten salt combustion, fluidized bed incineration, and ultraviolet/ozone destruction. Among wastes treated by emerging technologies are PCBs, various dioxins, pesticides and herbicides, chemical warfare agents, explosives and propellants, nitrobenzene, and hydrazine plus its derivatives.

Liquid chlorine reacts exothermically with polychlorinated biphenyl heat transfer liquid.

ALVARES AP ET AL; NATL RES COUNC CAN, (REP) NRCC/CNRC 18978, WORKSHOP COMB EFF XENOBIOTICS, 127-49 (1982). REVIEW ON ENZYME INDUCTIVE PROPERTIES OF PCBS. /POLYCHLORINATED BIPHENYLS/|TSCA CHIPs present a preliminary assessment of polychlorinated biphenyl's potential for injury to human health & the environment (available at EPA's TSCA Assistance Office: (202) 554-1404 or (800) 424-9065) /Polychlorinated biphenyls/

|Warning|H373 (100%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]|P260, P273, P314, P391, and P501|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

... Workers should be provided with suitable protective clothing: long-sleeved overalls, boots, overshoes, and bib-type aprons that cover the boot tops, and gloves. ... Safety glasses with side shields ... for eye protection. Respirators should be used in areas with PCB vapors and during installation and repair of containers and emergency activities. ...

Flame resistant.

... Dry sand or earth should be spread on the leak, or spill area. ...|Survey reports six case histories employing EPA's hazardous materials spills treatment trailer are reviewed. The trailer's ... treatment system has three mixed-media filters and three activated carbon columns to remove suspended, precipitated, and organic soluble materials. Spills of PCB, pentachlorophenol, kepone, termide (chlordane), heptachlor, aldrin, and dieldrin, toxaphene, and dinitrobutylphenol were treated by the EPA trailer, which was generally successful in mitigating environmental effects by filtering and carbon-adsorption. 90% removal was achieved for 21 of 23 compounds.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|Employees should wash their hands before eating, drinking and smoking ... and refrain from such activities in the polluted rooms. ...

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Irritating to skin and eyes.

NIOSH considers chlorodiphenyl containing 54% chlorine to be a potential occupational carcinogen. /Aroclor 1254/|NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concn. /Aroclor 1254/|Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 0.001 mg/cu m. /Aroclor 1254/

Toxicity

/SRP 1988: THIS PCB, BEING FOUND IN CLOPHEN A30, A40, A50, AND A60 BUT NOT IN AROCLORS/ ... FROM MANUFACTURING PLANTS, DURING DESTRUCTION OF MANUFACTURED ARTICLES CONTAINING PCBS IN MUNICIPAL & INDUSTRIAL WASTE-DISPOSAL BURNERS, THROUGH GRADUAL WEAR & WEATHERING OF PCB-CONTAINING PRODUCTS, & THROUGH LEACHING FROM LAND-FILL DUMPS.

Drug Information

DISPOSITION OF 37 PCB CONGENERS & ADIPOSE TISSUE-PLASMA PARTITION OF 28 PCB CONGENERS WERE STUDIED IN 26 PERSONS OCCUPATIONALLY EXPOSED TO VARIOUS PCBS (20-54% CL). CONCN OF PCBS IN ADIPOSE TISSUE & PLASMA WERE RELATED TO DURATION & INTENSITY OF EXPOSURE. PCB CONCN IN ADIPOSE TISSUE WAS PROPORTIONAL TO THAT IN PLASMA, WITH A PARTITION FOR TOTAL PCBS OF APPROX 190:1 INDICATED FROM REGRESSION ANALYSIS. PCB CONGENERS WITH CL IN BOTH 4-POSITIONS OF BIPHENYL RING WERE MAJOR COMPONENTS IN PLASMA & ADIPOSE TISSUE. CONGENERS WITH UNSUBSTITUTED 3,4-POSITIONS ON 1 OR BOTH OF BIPHENYL RINGS WERE OBSERVED AT LOWER CONCENTRATIONS. IN CONTRAST, THOSE COMPOUNDS WITH SUBSTITUENTS AT 2,4- & 3,4-POSITIONS ON BOTH RINGS WERE PRESENT IN MUCH HIGHER PROPORTIONS IN BLOOD OR ADIPOSE TISSUE THAN IN PCB MIXTURES USED. THESE COMPONENTS ALSO HAD HIGHER ADIPOSE TISSUE-PLASMA PARTITION THAN THOSE WITH UNSUBSTITUTED 3,4-POSITIONS, REGARDLESS OF DEGREE OF CHLORINATION.

A strain of Alcaligenes eutrophus, designated H850, that rapidly degrades a broad and unusual spectrum of polychlorinated biphenyls (PCBs) has been isolated and characterized. ... This strain was isolated from PCB-containing dredge spoils, grows well on biphenyl and 2-chlorobiphenyl but poorly on 3- and 4-chlorobiphenyl. Capillary gas-chromatographic analysis showed that biphenyl- grown resting cells of H850 degraded the components of 38 of the 41 largest peaks of Aroclor 1242 and 15 of the 44 largest peaks of Aroclor 1254, resulting in an overall reduction of PCBs by 81% for Aroclor 1242 (10 ppm) and 35% for Aroclor 1254 (10 ppm) in 2 days. H850 metabolized the predominantly ortho- substituted PCB congeners. ... The congener selectivity patterns indicate that a two-step process consisting of anaerobic dechlorination followed by oxidation by H850 can effectively degrade all of the congeners in Aroclor 1242 and possibly all those in Aroclor 1254.

269.15 Days|BIOLOGICAL HALF-LIFE OF 31 DICHLORO- TO DECHLOROBIPHENYL CONGENERS WERE MONITORED FOR 105 DAYS IN ADULT RAINBOW TROUT THAT WERE EXPOSED TO A SINGLE ORAL DOSE. IN WHOLE FISH, HALF-LIFE INCR FROM 5 DAYS TO NO APPARENT ELIMINATION AS THE NUMBER OF CHLORINES ON THE BIPHENYL INCR. THIS STRUCTURE-ACTIVITY RELATION WAS NOT AS EVIDENT IN MUSCLE WHERE HALF-LIFE RANGED FROM LESS THAN 5 DAYS TO 127 DAYS. DECLINE IN MUSCLE PCB MAY BE RELATED TO THE DECR IN LIPID LEVELS & REDISTRIBUTION OF CONGENERS WITHIN THE FISH. FROM STRUCTURE-ACTIVITY ANALYSIS OF HALF-LIFE IN WHOLE FISH, ELIMINATION IS ENHANCED FOR THOSE CONGENERS WITH LOWER CHLORINE CONTENT, WITH NO CHLORINE SUBSTITUTIONS IN THE ORTHO POSITIONS, & THOSE WITH 2 UNSUBSTITUTED CARBONS THAT ARE ADJACENT (VICINAL) ON THE BIPHENYL. A SIGNIFICANT DECLINE IN TOTAL PCB CONTENT IN WHOLE FISH, EQUIV TO HALF-LIFE OF 219 DAYS, WAS PARTLY DUE TO DECOMP OF THE PCB MIXTURE ADMIN, & SELECTIVE ELIMINATION OF LOWER CHLORINATED BIPHENYLS.

Nursing /by women exposed to PCB's/ ... should be discouraged because of the high amount of PCB's excreted with milk. ...|Food and Environmental Agents: Reported Sign or Symptom in Infant or Effect on Lactation: Polychlorinated biphenyls and polybrominated biphenyls: Lack of endurance, hypotonia, sullen, expressionless facies. /From Table 7/

2,3',4,4',5,5'-hexachlorobiphenyl

2,3′,4,4′,5,5′-Hexachlorobiphenyl Use and Manufacturing

Methods of Manufacturing

2,4,5-TRICHLOROANILINE IS COUPLED WITH 1,2,3-TRICHLOROBENZENE BY USING AN EXCESS OF THE LATTER REACTANT WHICH ALSO SERVES AS THE SOLVENT MEDIUM. THE COUPLING REACTION PROCEEDS SMOOTHLY AFTER THE ADDITION OF ISOAMYL NITRITE, AND THE PCB PRODUCT IS READILY ISOLATED AFTER A SERIES OF CHROMATOGRAPHIC PROCEDURES

Detected at trace levels in Clophen A50 and A60.

DOMESTIC /USA/ PRODUCTION OF POLYCHLORINATED BIPHENYLS WAS STOPPED IN OCTOBER 1977 /POLYCHLORINATED BIPHENYLS/

MASS FRAGMENTOGRAPHY WAS USED TO CONFIRM THE PRESENCE OF HEXACHLOROBIPHENYLS IN RIVER WATER.

Computed Properties

Molecular Weight:360.9
XLogP3:7.5
Rotatable Bond Count:1
Exact Mass:359.841466
Monoisotopic Mass:357.844416
Heavy Atom Count:18
Complexity:274
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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