Dichlorodiphenyldichloroethane: Difference between revisions

| verifiedrevid = 414419606

| ImageSize = 200px

| IUPACName = 1-chloro-4-[2,2-dichloro-1-(4-</br>chlorophenyl)ethyl]benzene

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| Formula = [[Carbon|C]]₁₄[[Hydrogen|H]]₁₀[[Chlorine|Cl]]₄

| MolarMass = 320.04

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| MeltingPt = 109.5°[[Celsius|C]]

| Melting_notes = 229.1°[[Fahrenheit|F]]

| BoilingPt = 350°C

| Boiling_notes = 662°F

| LogP = 6.02 ([[octanol]]-water)

| HenryConstant = 6.6×10⁻⁶ [[Atmosphere (unit)|atm]] ∙ m³/[[Mole (unit)|mol]]

| AtmosphericOHRateConstant = 4.34×10⁻¹² cm³/[[molecule]] ∙ [[Second|s]]

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| Section5 = {{Chembox Pharmacology

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| HalfLife = 4 days in air; 160 days in anaerobic soil; when in water ([[hydrolysis]]), depends on various factors (one or more decades in rivers and lakes, 190 years at 27°C and [[pH]] 3–5)<ref name="HSDB">“DDD.” ''Hazardous Substances Data Bank''. United States National Library of Medicine. 25 Apr. 2007 <http://toxmap.nlm.nih.gov/toxmap/main/chemPage.jsp?chem=4,4-DICHLORODIPHENYLDICHLOROETHANE then click “Env. Fate / Exposure”>.</ref>

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| Section6 = {{Chembox Explosive

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| Section7 = {{Chembox Hazards

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| OtherCpds = [[Dichlorodiphenyldichloroethylene|DDE]], [[DDT]], [[mitotane]], [[perthane]]}}

'''Dichlorodiphenyldichloroethane''' (DDD) is an [[Organochloride|organochlorine]] [[insecticide]] that is slightly irritating to the skin.<ref name="Merck">Merck Index, 11th ed, p482</ref> DDD is a [[Metabolomics|metabolite]] of [[DDT]].<ref name="EPA">“p,p'-Dichlorodiphenyl dichloroethane (DDD) (CASRN 72-54-8).” ''Integrated Risk Information System''. 25 Jan. 2007. United States Environmental Protection Agency. 23 Apr. 2007 <http://www.epa.gov/iris/subst/0347.htm>.</ref> DDD is colorless and crystalline<ref name="WebsterNinthNewCollege">Mish, Frederick C., Editor in Chief. “DDD.” ''Webster’s Ninth New Collegiate Dictionary''. 9^th ed. Springfield, MA: Merriam-Webster Inc., 1985.</ref>; it is closely related chemically and is similar in properties to DDT, but it is considered to be less toxic to animals than is DDT.<ref name="WebsterNewWorldSecondCollege">Guralnik, David B., Editor in Chief. “DDD.” ''Webster’s New World Dictionary of the American Language''. Second College Edition. New York, NY: Prentice Hall Press, 1986.</ref> The molecular formula for DDD is (ClC₆H₄)₂CHCHCl₂ or C₁₄H₁₀Cl₄, whereas the formula for DDT is (ClC₆H₄)₂CHCCl₃ or C₁₄H₉Cl₅.

DDD is in the “[[List of IARC Group 2B carcinogens|Group B2]]” classification, meaning that it is a probable [[human]] [[carcinogen]]. This is based on an increased incidence of [[Lung cancer|lung tumors]] in male and female [[Mouse|mice]], [[Liver cancer|liver tumors]] in male mice, and [[Thyroid cancer|thyroid tumors]] in male [[rat]]s. Further basis is that DDD is so similar to and is a metabolite of DDT, another probable human carcinogen.<ref name="EPA">“p,p'-Dichlorodiphenyl dichloroethane (DDD) (CASRN 72-54-8).” ''Integrated Risk Information System''. 25 Jan. 2007. United States Environmental Protection Agency. 23 Apr. 2007 <http://www.epa.gov/iris/subst/0347.htm>.</ref>

DDD is no longer registered for agricultural use in the [[United States]], but the general population continues to be exposed to it due to its long persistence time. The primary source of exposure is oral ingestion of food.<ref name="HSDB">“DDD.” ''Hazardous Substances Data Bank''. United States National Library of Medicine. 25 Apr. 2007 <http://toxmap.nlm.nih.gov/toxmap/main/chemPage.jsp?chem=4,4-DICHLORODIPHENYLDICHLOROETHANE then click “Env. Fate / Exposure”>.</ref>

1946 is the date of the earliest recorded use in English of the abbreviation “DDD” to stand for dichlorodiphenyldichloroethane, as far as could be determined.<ref name="WebsterNinthNewCollege">Mish, Frederick C., Editor in Chief. “DDD.” ''Webster’s Ninth New Collegiate Dictionary''. 9^th ed. Springfield, MA: Merriam-Webster Inc., 1985.</ref>

| Benzene, 1,1'-(2,2-</br>dichloroethylidene)</br>bis(4-chloro- (9CI)

| 1,1'-(2,2-Dichloroethylidene)bis</br>(4-chlorobenzene)

| Ethane, 1,1-</br>dichloro-2,2-bis(p-</br>chlorophenyl)-

| Benzene, 1,1'-(2,2-</br>dichloroethylidene)bis(4-chloro-

| 1,1-Bis(4-chlorophenyl)-2,2-</br>dichloroethane

| 1,1-Bis(p-chlorophenyl)-2,2-</br>dichloroethane

| 1,1-Dichlor-2,2-bis(4-chlor-</br>phenyl)-aethan ([[German language|German]])

| 1,1-Dichloro-2,2-bis(4-</br>chlorophenyl)-ethane ([[French language|French]])

| 1,1-Dichloro-2,2-bis(4-</br>chlorophenyl)ethane

| 1,1-Dichloro-2,2-bis(p-</br>chlorophenyl)ethane

| 1,1-Dichloro-2,2-bis</br>(parachlorophenyl)ethane

| 1,1-Dichloro-2,2-di(4-</br>chlorophenyl)ethane

| 1,1-Dicloro-2,2-bis(4-cloro-fenil)-</br>etano ([[Italian language|Italian]])

| 2,2-Bis(4-chlorophenyl)-1,1-</br>dichloroethane

| 2,2-Bis(p-chlorophenyl)-1,1-</br>dichloroethane

| 4,4'-</br>Dichlorodiphenyldichloroethane

| Benzene, 1,1'-(2,2-</br>dichloroethylidene)bis[4-chloro-

| Ethane, 1,1-dichloro-2,2-bis(p-</br>chlorophenyl)-

| para,para'-</br>Dichlorodiphenyldichloroethane

*“Chemicals: Dichlorodiphenyldichloroethane.” ''The Comparative Toxicogenomics Database''. [[Mount Desert Island Biological Laboratory]], 11 Apr. 2007 <http://ctd.mdibl.org/detail.go?type=chem&acc=D003632>.

*“Data From SRC PhysProp Database.” ''SRC PhysProp Database''. Syracuse Research Corporation. 11 Apr. 2007 <http://esc.syrres.com/interkow/webprop.exe?CAS=72-54-8>.

*“DDD.” ''Hazardous Substances Data Bank''. [[United States National Library of Medicine]]. 25 Apr. 2007 <http://toxmap.nlm.nih.gov/toxmap/main/chemPage.jsp?chem=4,4-DICHLORODIPHENYLDICHLOROETHANE then click “Env. Fate / Exposure”>.

*“DDD—RN: 72-54-8.” ''ChemIDplus Lite Record''. 9 Sept. 2004. United States National Library of Medicine Specialized Information Services. 11 Apr. 2007 <http://chem2.sis.nlm.nih.gov/chemidplus/direct.jsp?regno=72-54-8>.

*Guralnik, David B., Editor in Chief. “DDD.” ''[[Webster's New World Dictionary|Webster’s New World Dictionary of the American Language]]''. Second College Edition. New York, NY: [[Prentice Hall|Prentice Hall Press]], 1986. ISBN 0-671-41809-2 (indexed), ISBN 0-671-41807-6 (plain edge), ISBN 0-671-41811-4 (pbk.), and ISBN 0-671-47035-3 (LeatherKraft).

*Mish, Frederick C., Editor in Chief. “DDD.” ''[[Webster's Dictionary#The Collegiate Dictionary|Webster’s Ninth New Collegiate Dictionary]]''. 9^th ed. Springfield, MA: [[Merriam-Webster]] Inc., 1985. ISBN 0-87779-508-8, ISBN 0-87779-509-6 (indexed), and ISBN 0-87779-510-X (deluxe).

*“p,p'-DDD.” ''Substance Registry System''. 1 Feb. 2006. [[United States Environmental Protection Agency]]. 11 Apr. 2007 <http://iaspub.epa.gov/srs/srs_proc_qry.navigate?P_SUB_ID=4937>.

*[http://toxmap.nlm.nih.gov/toxmap/main/chemPage.jsp?chem=4,4-DICHLORODIPHENYLDICHLOROETHANE TOXMAP Chemical Page for DDD]

*[http://ptcl.chem.ox.ac.uk/MSDS/RH/rhothane.html MSDS for rhothane (DDD)] provided by the [[Physical and Theoretical Chemistry Laboratory]] of the [[University of Oxford]]

[[Category:Persistent organic pollutants]]

[[Category:Aromatic compounds]]

[[de:Dichlordiphenyldichlorethan]]

[[fr:Dichlorodiphényldichloroéthane]]

[[zh:2,2-双(对氯苯基)-1,1-二氯乙烷]]