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

3,3′,4,4′,5,5′-Hexachlorobiphenyl

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

3,3′,4,4′,5,5′-Hexachlorobiphenyl 

structure
  • CAS No:

    32774-16-6

  • Formula:

    C12H4Cl6

  • Chemical Name:

    3,3′,4,4′,5,5′-Hexachlorobiphenyl

  • Synonyms:

    1,1′-Biphenyl,3,3′,4,4′,5,5′-hexachloro-;Biphenyl,3,3′,4,4′,5,5′-hexachloro-;3,3′,4,4′,5,5′-Hexachloro-1,1′-biphenyl;3,3′,4,4′,5,5′-Hexachlorobiphenyl;3,4,5,3′,4′,5′-Hexachlorobiphenyl;PCB 169;CB 169;HxCB 169;H 6CB 169

  • Categories:

    Analytical Chemistry  >  Food Safety

Description

Polychlorinated biphenyls are mixtures of up to 209 individual chlorinated compounds (known as congeners). There are no known natural sources of PCBs. PCBs are either oily liquids or solids that are colorless to light yellow. Some PCBs can exist as a vapor in air. PCBs have no known smell or taste. Many commercial PCB mixtures are known in the U.S. by the trade name Aroclor.PCBs have been used as coolants and lubricants in transformers, capacitors, and other electrical equipment because they don't burn easily and are good insulators. The manufacture of PCBs was stopped in the U.S. in 1977 because of evidence they build up in the environment and can cause harmful health effects. Products made before 1977 that may contain PCBs include old fluorescent lighting fixtures and electrical devices containing PCB capacitors, and old microscope and hydraulic oils.|3,4,5,3',4',5'-Hexachlorobiphenyl is a trichlorobenzene and a hexachlorobiphenyl.|Polychlorinated biphenyls (PCBs) are a group of chemicals that contain 209 individual compounds (known as congeners) with varying harmful effects. Information on specific congener toxicity is very limited. Most toxicity testing has been done on specific commercial mixtures; however, PCB mixtures found in the environment will differ in composition from the commercial mixtures because of partitioning, biotransformation, and bioaccumulation. The U.S. Environmental Protection Agency (EPA) treats all PCBs as being potentially hazardous based on results from some formulations. However, this can have large uncertainty for any given mixture situation. PCBs are no longer produced or used in the United States today; the major source of exposure to PCBs today is the redistribution of PCBs already present in soil and water. Chronic (long-term) exposure to some PCB formulations by inhalation in humans results in respiratory tract symptoms, gastrointestinal effects, mild liver effects, and effects on the skin and eyes such as chloracne, skin rashes, and eye irritation. Epidemiological studies indicate an association between dietary PCB exposures and developmental effects. Human studies provide inconclusive, yet suggestive, evidence of an association between PCBs exposure and cancer. Animal studies have reported an increase in liver tumors in rats and mice exposed orally to all tested PCB formulations. EPA has classified PCBs as a Group B2, probable human carcinogen.

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

360.88

360.88

215-648-1

T2P1WH546D

DTXSID2038314

2903999090

Characteristics

0

6.90

1.6±0.1 g/cm3

198 °C

436.6±40.0 °C at 760 mmHg

223.1±24.7 °C

1.627

1.41e-09 M

PCB material should be stored in closed containers, in ventilated areas PCB's should be handled in isolated areas of the plant, where efficient ventilation systems remove airborne PCB's.

169.4 Ų [M-Cl+O]-

Safety Information

PCB's are chemically very inert and are stable to conditions of hydrolysis and oxidation in industrial use. Photochemical degradation may be one route of their breakdown in the environment.

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. /Polychlorinated biphenyl/

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.|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)

|Warning|H373 **: Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]|P260, P273, P314, P391, and P501|H373 (100%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]|Aggregated GHS information provided by 148 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Aggregated GHS information provided by 49 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H373: Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P308+P313, P312, P314, P322, P330, P361, P363, P403+P233, P405, and P501

... 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.|/In a confined space: The worker/ should wear appropriate protective equipment and be connected by a lifeline harness to an outside worker.|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/

Polychlorinated biphenyls are mixtures of up to 209 individual chlorinated compounds (known as congeners). There are no known natural sources of PCBs. PCBs are either oily liquids or solids that are colorless to light yellow. Some PCBs can exist as a vapor in air. PCBs have no known smell or taste. Many commercial PCB mixtures are known in the U.S. by the trade name Aroclor.PCBs have been used as coolants and lubricants in transformers, capacitors, and other electrical equipment because they don't burn easily and are good insulators. The manufacture of PCBs was stopped in the U.S. in 1977 because of evidence they build up in the environment and can cause harmful health effects. Products made before 1977 that may contain PCBs include old fluorescent lighting fixtures and electrical devices containing PCB capacitors, and old microscope and hydraulic oils.|Polychlorinated biphenyls (PCBs) are a group of chemicals that contain 209 individual compounds (known as congeners) with varying harmful effects. Information on specific congener toxicity is very limited. Most toxicity testing has been done on specific commercial mixtures; however, PCB mixtures found in the environment will differ in composition from the commercial mixtures because of partitioning, biotransformation, and bioaccumulation. The U.S. Environmental Protection Agency (EPA) treats all PCBs as being potentially hazardous based on results from some formulations. However, this can have large uncertainty for any given mixture situation. PCBs are no longer produced or used in the United States today; the major source of exposure to PCBs today is the redistribution of PCBs already present in soil and water. Chronic (long-term) exposure to some PCB formulations by inhalation in humans results in respiratory tract symptoms, gastrointestinal effects, mild liver effects, and effects on the skin and eyes such as chloracne, skin rashes, and eye irritation. Epidemiological studies indicate an association between dietary PCB exposures and developmental effects. Human studies provide inconclusive, yet suggestive, evidence of an association between PCBs exposure and cancer. Animal studies have reported an increase in liver tumors in rats and mice exposed orally to all tested PCB formulations. EPA has classified PCBs as a Group B2, probable human carcinogen.

Toxicity

LD50 Mouse (C57B1/6J) male oral 19 mg/kg/28 day

/SRP 1988: THIS POLYCHLORINATED BIPHENYL HAS ENTERED THE ENVIRONMENT BY APPLICATIONS OF AROCLOR 1248 AND 1254/ ... 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. /POLYCHLORINATED BIPHENYLS/

9.33e+05

Drug Information

FOLLOWING ORAL ADMIN TO LACTATING COW, LEVELS OF 3,3',4,4',5,5'-HEXACHLOROBIPHENYL REACHED PEAK CONCENTRATIONS IN MILK BETWEEN THE 2ND & 3RD DAY, & RAPIDLY DECLINED THEREAFTER.|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.

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 ELIM 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, ELIM 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 ELIM OF LOWER CHLORINATED BIPHENYLS.

... In a human population occupationally exposed /to polychlorinated biphenyls (PCBs), including 3,4,5,3',4',5'-hexachlorobiphenyl/, an increase of urinary porphyrins has been noted, one of which is significantly linked with the rise of an enzymatic induction marker, urinary D-glucaric acid, but no correlat ion can be made with PCB blood level. The rise in urinary porphyrins seems to be an early rather specific reflection of the biological impact of polychlorinated biphenyls, which justifies the search for it in the biological surveillance of exposed workers.|Aryl hydrocarbon hydroxylase-inducing potency of toxic polychlorinated aromatic hydrocarbons such as polychlorinated dibenzofuran isomers, 3,4,5,3',4',5'-hexachlorobiphenyl and 2,3,7,8-tetrachlorodibenzo-p-dioxin was investigated in human lymphoblastoid cell lines with different aryl hydrocarbon hydroxylase inducibility for 3-methylcholanthrene obtained from healthy subjects. Each of the cell lines was treated with eight individual polychlorinated dibenzofuran isomers, 2,3,7,8-tetrachlorodibenzo-p-dioxin, and 3,4,5,3',4',5'-hexachlorobophenyl at doses of 1.9-15 ng/ml of culture medium, 1.9-7.5 ng/ml, respectively. ... 3,4,5,3',4',5'-Hexachlorobiphenyl at a dose of 95 ng/ml, did not induce aryl hydrocarbon hydroxylase activity. ...|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/

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

Immunological (Immune System), Neurological (Nervous System)

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

Methods of Manufacturing

3,4,5-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|ANALYSIS OF AROCLOR 1254 & 1248 FOR POLYCHLORINATED BIPHENYL (PCB) LACKING 2,2'-CL SUBSTITUTION REVEALED PRESENCE OF 3,4,4'-TRICHLOROBIPHENYL, 3,3'4,4'-TETRACHLOROBIPHENYL & 3,3',4,5,5'-PENTACHLOROBIPHENYL.

1,1'-Biphenyl, chloro derivs.: ACTIVE|R - indicates a substance that is the subject of a TSCA section 6 risk management rule.

Chemical Classes -> Dioxins, Furans, PCBs (contain phenyl rings of carbon atoms), Pesticides (chemicals used for killing pests, such as rodents, insects, or plants)|Hazardous Air Pollutants (HAPs)|Food Contaminant -> CONTAMINANT; -> JECFA Functional Classes

Food Contaminant -> CONTAMINANT;

Computed Properties

Molecular Weight:360.9
XLogP3:7.4
Rotatable Bond Count:1
Exact Mass:359.841466
Monoisotopic Mass:357.844416
Heavy Atom Count:18
Complexity:234
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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