72-55-9

Basic information

• Product Name: 4,4'-DDE
• Synonyms: Benzene,1,1'-(dichloroethenylidene)bis[4-chloro- (9CI); Ethylene,1,1-dichloro-2,2-bis(p-chlorophenyl)- (7CI,8CI);1,1-Bis(4-chlorophenyl)-2,2-dichloroethene;1,1-Bis(p-chlorophenyl)-2,2-dichloroethylene;1,1-Dichloro-2,2-bis(p-chlorophenyl)ethylene;1,1-Dichloro-2,2-di(p-chlorophenyl)ethylene;2,2-Bis(4-chlorophenyl)-1,1-dichloroethylene; 2,2-Dichloro-1,1-bis(4-chlorophenyl)ethylene;4,4'-DDE; 4,4'-Dichlorodiphenyldichloroethylene; DDE; NSC 1153; p,p'-DDE;p,p'-Dichlorodiphenyldichloroethylene
• CAS NO: 72-55-9
• Molecular Formula: C₁₄H₈Cl₄
• Molecular Weight: 318.02
• EINECS: 200-784-6
• Mol File: 72-55-9.mol
• Article Data: 36

Chemical Properties

• Melting Point: 87-90℃
• Appearance: /
• Water Solubility: 0.00000013 g/100 mL
• CAS DataBase Reference: 4,4'-DDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-DDE(72-55-9)
• EPA Substance Registry System: 4,4'-DDE(72-55-9)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R22:Harmful if swallowed.; R33:Danger of cummulative effects.
• Safety Statements: S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 72-55-9(Hazardous Substances Data)

Usage

General Description

4,4'-DDE, also known as Dichlorodiphenyldichloroethylene, is a chemical compound that is generated as a byproduct of DDT, a pesticide historically used to control mosquito populations. It is known for its long persistence in the environment due to its high resistance to degradation. This chemical has a tendency to bioaccumulate in animals, leading it to reach higher concentrations at higher levels of the food chain. Studies have indicated potential harmful effects on wildlife and human health, possibly disrupting endocrine function and potentially having carcinogenic effects.

InChI:InChI=1/C14H8Cl4/c15-11-5-1-9(2-6-11)13(14(17)18)10-3-7-12(16)8-4-10/h1-8H

Upstream product

• 50-29-3 p,p'-DDT 
• 62-53-3 aniline 
• 3567-18-8 4-chloro-α-(4-chlorophenyl)-α-dichloromethylbenzenemethanol 
• 3563-45-9 1,1,1,2-tetrachloro-2,2-bis-(4-chloro-phenyl)-ethane 
• 67-48-1 choline chloride 
• 56-23-5 tetrachloromethane 
• 91-22-5 quinoline 
• 110-86-1 pyridine 
• 108-91-8 cyclohexylamine 
• 75-64-9 tert-butylamine 
• 107-11-9 1-amino-2-propene 
• 107-10-8 propylamine 
• 109-89-7 diethylamine 
• 108-95-2 phenol 

Downstream Products

• 1022-22-6 1-chloro-2,2-bis(p-chlorophenyl)ethylene 
• 90-97-1 4,4'-dichlorobenzophenone 
• 2642-82-2 2,2-bis(p-chlorophenyl)ethanol 
• 83-05-6 bis(4'-chlorophenyl)acetic acid 
• 62938-16-3 4,4'-Dichlor-3-methansulfonyl-benzophenon 
• 2675-34-5 4,4'-dichloro-benzophenone-(2,4-dinitro-phenylhydrazone) 
• 80-06-8 chlorfenethol 
• 2642-81-1 1,1-bis(p-chlorophenyl)ethene 
• 77381-58-9 3,5-Bis-1,2,4-trithiolane 
• 77381-53-4 2-[Bis-(4-chloro-phenyl)-methylene]-[1,3]dithietane 
• 77381-48-7 C₁₆H₁₄Cl₂S₂ 
• 77381-54-5 Bis-(4-chloro-phenyl)-dithioacetic acid methyl ester 
• 97586-32-8 disodium benzophenone-4,4'-disulfonate 
• 97586-06-6 benzophenone-4,4'-disulfonamide 

Relevant articles and documents

-

-

Compounds and methods for the reduction of halogenated hydrocarbons

The present application relates to methods for the reduction of halogenated hydrocarbons using compounds of Formula (I): wherein the reduction of the halogenated compounds is carried out, for example, under ambient conditions without the need for a transition metal containing co-factor. The present application also relates to methods of recovering precious metals using compounds of Formula (I) that are absorbed onto a support material.

Electrochemical dechlorination of 4,4′-(2,2,2-trichloroethane-1,1-diyl)bis(chlorobenzene) (DDT) at silver cathodes

Cyclic voltammetry and controlled-potential (bulk) electrolysis have been employed to investigate the reduction of 4,4′-(2,2,2-trichloroethane-1,1-diyl)bis(chlorobenzene) (DDT) at silver cathodes in dimethylformamide (DMF) containing 0.050 M tetramethylammonium tetrafluoroborate (TMABF4). In addition, this work has been extended to the individual reductions of two degradation products, namely 4,4′-(2,2-dichloroethane-1,1-diyl)bis(chlorobenzene) (DDD) and 4,4′-(ethene-1,1-diyl)bis(chlorobenzene) (DDNU). At a scan rate of 100 mV s-1, cyclic voltammograms for irreversible reduction of DDT at a silver electrode exhibit four prominent cathodic peaks in DMF and CH3CN, and three prominent cathodic peaks in DMSO. On the other hand, reduction of DDD and DDNU at silver in DMF-0.050 M TMABF4displays four and two irreversible peaks, respectively. Carbon-chlorine bonds of the -CCl3moiety of DDT and of the -CHCl2moiety of DDD are reduced more easily at silver than at glassy carbon. Bulk electrolyses of DDT at a silver gauze cathode in DMF-0.050 M TMABF4afford a potential-dependent mixture of products that includes DDD, DDNU, 4,4′-(2,2-dichloroethene-1,1-diyl)bis(chlorobenzene) (DDE), 4,4′-(2-chloroethene-1,1-diyl)bis(chlorobenzene) (DDMU), 4,4′-(2-chloroethane-1,1-diyl)bis(chlorobenzene) (DDMS), 1-chloro-4-(1-phenylvinyl)benzene (PVB), 1,1′-diphenylethylene (DPE), and 1,1′-ethylidenebisbenzene (EBB). However, at more negative potentials, the principal products are completely dechlorinated DPE and EBB. Dechlorination of DDT at silver appears to proceed via a series of steps involving carbanion intermediates arising from direct reduction of alkyl and aryl carbon-chlorine bonds along with hydroxide-promoted E2 elimination of chloride. When DMF-d7was used as solvent, no evidence for deuterium atom incorporation into any product was seen, which indicates that radical intermediates do not play a significant role in the reduction of DDT.