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

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

Uses

Used in Pesticide Industry:
4,4'-DDE is used as a byproduct in the production of DDT, a pesticide that was historically used for controlling mosquito populations. Its persistence in the environment and bioaccumulation in animals have raised concerns about its potential harmful effects on wildlife and human health.
Used in Environmental Research:
4,4'-DDE is used as a subject of study in environmental research to understand its persistence, bioaccumulation, and potential harmful effects on wildlife and human health. This research helps in developing strategies for mitigating the environmental impact of this chemical compound.
Used in Toxicology Studies:
4,4'-DDE is used as a test substance in toxicology studies to investigate its potential endocrine-disrupting effects and carcinogenic properties. These studies contribute to the understanding of the health risks associated with exposure to this chemical compound and inform regulatory decisions.

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

• 110-86-1 pyridine 
• 50-29-3 p,p'-DDT 
• 91-22-5 quinoline 
• 56-23-5 tetrachloromethane 
• 67-48-1 choline chloride 
• 3563-45-9 1,1,1,2-tetrachloro-2,2-bis-(4-chloro-phenyl)-ethane 
• 3567-18-8 4-chloro-α-(4-chlorophenyl)-α-dichloromethylbenzenemethanol 
• 62-53-3 aniline 
• 67-56-1 methanol 
• 91-66-7 N,N-diethylaniline 
• 57-09-0 cetyltrimethylammonim bromide 
• 112-02-7 cetyltrimethylammonium chloride 
• 505-86-2 cetyltrimethylammonium hydroxide 
• 1545-65-9 F-DDT 

Downstream Products

• 101-76-8 4,4'-dichlorodiphenylmethane 
• 83-05-6 bis(4'-chlorophenyl)acetic acid 
• 33406-61-0 bis(4-chloro-3,5-dinitrophenyl)methanone 
• 90-98-2 4,4'-Dichlorobenzophenone 
• 1022-22-6 1-chloro-2,2-bis(p-chlorophenyl)ethylene 
• 79082-91-0 1,2,3,4-Tetra-tert-butyl-tetraphosphetane 
• 61695-12-3 tri-tert-butylcyclotriphosphane 
• 90600-95-6 3--1,2-di-tert-butyl-1,2-diphosphiran 
• 62938-16-3 4,4'-Dichlor-3-methansulfonyl-benzophenon 
• 62938-14-1 1,1-dichloro-2-(4-chloro-2-methylsulfonylphenyl)-2-(4-chlorophenyl)ethylene 
• 62938-13-0 1,1-dichloro-2-(3-methylsulfonyl-4-chlorophenyl)-2-(4-chlorophenyl)ethene 
• 62938-15-2 C₁₆H₁₂Cl₄O₄S₂ 
• 1820-42-4 bis(4-chlorophenyl)acetylene 
• 530-48-3 1,1-Diphenylethylene 

Relevant articles and documents

Influence of n-Butyl and n-Hezil Alcohols in the Dehydrohalogenation of DDT in Cationic Micelles of N-Cetyl-N,N,N-trimethylammonium Bromide, Chloride, and Hydroxide

The incorporation of n-butyl and n-hexyl alcohols on cationic micelles of hexadecyltrimethylammonium bromide, chloride, and hydroxide (CTAB, CTAC, and CTAOH) decreases the rate of the basic dehydrohalogenation of DDT in simple cationic micelles.From the kinetic results and on the basis of the Berezin model the mean nolar volume of micellar pseudophase for simple micelles and surfactant/alcohol system has been evaluated.

Aerobic Electrochemical Transformations of DDT to Oxygen-Incorporated Products Catalyzed by a B12 Derivative

Electrochemical transformations of DDT into oxygen-incorporated products, amides and esters, catalyzed by a B12 derivative, heptamethyl cobyrinate perchlorate, have been developed under aerobic conditions. The dechlorinative oxygenation of DDT forms the acyl chloride as an intermediate for the synthesis of the amide and ester in the reaction with the amine and alcohol, respectively. This electrochemical method demonstrated with 20 oxygen-incorporated dechlorinated products up to 88% yields with 15 new compounds and was also successfully applied to the conversion of methoxychlor to an amide and ester.

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.

Kinetic and quantum chemical studies of the mechanism of dehydrochlorination of 2,2-diaryl-1,1,1-trichloroethanes with nitrite ions

The E2 mechanism has been proposed for the dehydrochlorination of 2,2-diaryl-1,1,1-trichloroethanes with nitrite ion, leading to 2,2-diaryl-1,1-dichloroethenes, on the basis of experimental kinetic study and quantum chemical simulation.

Design of a bimetallic Au/Ag system for dechlorination of organochlorides: Experimental and theoretical evidence for the role of the cluster effect

The experimental study of dechlorination activity of a Au/Ag bimetallic system has shown formation of a variety of chlorinated bimetallic Au/Ag clusters with well-defined Au:Ag ratios from 1:1 to 4:1. It is the formation of the Au/Ag cluster species that mediated C-Cl bond breakage, since neither Au nor Ag species alone exhibited a comparable activity. The nature of the products and the mechanism of dechlorination were investigated by ESI-MS, GC-MS, NMR, and quantum chemical calculations at the M06/6-311G(d)&SDD level of theory. It was revealed that formation of bimetallic clusters facilitated dechlorination activity due to the thermodynamic factor: C-Cl bond breakage by metal clusters was thermodynamically favored and resulted in the formation of chlorinated bimetallic species. An appropriate Au:Ag ratio for an efficient hydrodechlorination process was determined in a joint experimental and theoretical study carried out in the present work. This mechanistic finding was followed by synthesis of molecular bimetallic clusters, which were successfully involved in the hydrodechlorination of CCl4 as a low molecular weight environment pollutant and in the dechlorination of dichlorodiphenyltrichloroethane (DDT) as an eco-toxic insecticide. High activity of the designed bimetallic system made it possible to carry out a dechlorination process under mild conditions at room temperature.

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.

Synthesis, electrochemistry, spectroelectrochemistry and catalytic properties in DDT reductive dechlorinationin of iron(II) phthalocyanine, 2,3-and 3,4-tetrapyridinoporphyrazine complexes

Iron(II) 2,3-and 3,4-tetrapyridinoporphyrazine complexes (2,3-PyD and 3,4-PyD) were synthesized and characterized as to their electrochemistry, UV-visible spectroelectrochemistry and catalytic properties towards the reductive dechlorination of 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethane (p,p′-DDT) in pyridine, dimethyl sulfoxide (DMSO), N,N′- dimethylacetamide (DMA) and N,N′-dimethylformamide (DMF). These properties were compared with those of the unsubstituted iron(II) phthalocyanine ((Pc)Fe). Electrochemistry indicates that there are up to three reductions and one oxidation in the three investigated derivatives. The easiest reduction takes place for 3,4-PyD while the most difficult one occurs for (Pc)Fe in all of the solvents investigated. The first reduction is metal-centered corresponding to the formation of [P(-2)Fe(I)]- while the second and third reductions are ring-centered leading stepwise to the generation of [P(-3)Fe(I)] 2- · and [P(-4)Fe(I)]3-, where P = phthalocyanine or tetrapyridinoporphyrazine rings. Aggregation exists in the solutions of all three iron complexes and its extent depends upon the nature and concentration of the iron compounds and the binding property of each solvent. The order of the extent of aggregation for the three iron derivatives is 3,4-PyD > 2,3-PyD > (Pc)Fe. Stronger binding solvents such as pyridine and DMSO do not favor the aggregation. The singly and doubly reduced species of investigated complexes, [P(-2)Fe(I)]- and [P(-3)Fe(I)]2- ·, are active in DDT reductive dechlorination, the latter of which has better catalytic performance. As a result, three products, 1,1-bis(4-chlorophenyl)-2,2- dichloroethane (p,p′-DDD), 1,1-bis(4-chlorophenyl)-2,2-dichloroethylene (p,p′-DDE), and 1,1-bis(4-chlorophenyl)-2-chloroethylene (p,p′-DDMU), were obtained after the dechlorination of DDT catalyzed by each iron complex. The increasing order of catalytic performance is 3,4-PyD 2,3-PyD (Pc)Fe in pyridine, which is superior to DMSO and DMA for the DDT dechlorination reaction. An overall electrocatalytic mechanism is proposed for DDT reductive degradation based on the electrochemical and UV-visible spectroelectrochemical results.

Reductive dechlorination of DDT electrocatalyzed by synthetic cobalt porphyrins in N,N′-dimethylformamide

Two cobalt porphyrins, (OEP)CoII and (TPP)CoII, where OEP and TPP are the dianions of octaethylporphyrin and tetraphenylporphyrin, respectively, were examined as electrocatalysts for the reductive dechlorination of DDT (1,1-bis(4-chlorophenyl)-2,2,2-trichloroethane) in N,N′- dimethylformamide (DMF) containing 0.1 M tetra-n-butylammonium perchlorate (TBAP). No reaction is observed between DDT and the porphyrin in its Co(II) oxidation state but this is not the case for the reduced Co(I) forms of the porphyrins which electrocatalyze the dechlorination of DDT, giving initially DDD (1,1-bis(4-chlorophenyl)-2,2-dichloroethane), DDE (1,1-bis(4-chlorophenyl)-2, 2-dichloroethylene) and DDMU (1,1-bis(4-chlorophenyl)-2-chloroethylene) as determined by GC-MS analysis of the reaction products. A further dechlorination product, DDOH (2,2-bis(4-chlorophenyl)ethanol), is also formed on longer timescales when using (TPP)Co as the electroreduction catalyst. The effect of porphyrin structure and reaction time on the dechlorination products was examined by GC-MS, cyclic voltammetry, controlled potential electrolysis and UV-visible spectroelectrochemistry and a mechanism for the reductive dechlorination is proposed.

Enhanced reactivity of hydrophobic vitamin B12 towards the dechlorination of DDT in ionic liquid

The electrolytic reductive dechlorination of 1,1-bis(p-chlorophenyl)-2,2,2- trichloroethane (DDT) in the ionic liquid (IL) 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF4]) in the presence of a cobalamin derivative afforded 1,1′-(ethylidene)bis(4-chlorobenzene) (DDO) and 1,1′-(ethenylidene)bis(4-chlorobenzene) (DDNU) with 1,1′-(2- chloroethylidene)bis(4-chlorobenzene) (DDMS); the enhanced reactivity, as well as the recyclability of the cobalamin derivative catalyst in IL, makes the present system more efficient for the development of "green" technologies. The Royal Society of Chemistry.

Hydrophobic vitamin B12· part 19: Electroorganic reaction of DDT mediated by hydrophobic vitamin B12

The controlled-potential electrolysis of 1,1-bis(4-chlorophenyl)-2,2,2- trichloroethane (DDT) was carried out at -1.4 V vs. Ag-AgCl in the presence of a hydrophobic vitamin B12, heptamethyl cobyrinate perchlorate. DDT was dechlorinated to form 1,1-bis(4-chlorophenyl)-2,2-dichloroethane (DDD), 1,1-bis(4-chlorophenyl)-2,2-dichloroethylene (DDE), 1-chloro-2,2-bis(4- chlorophenyl)ethylene (DDMU) and 1,1,4,4-tetrakis(4-chlorophenyl)-2,3-dichloro- 2-butene (TTDB) (E/Z), and quantitative recovery of the catalyst after the electrolysis was confirmed by electronic spectroscopy. A photo-sensitive intermediate having a cobalt-carbon bond formed during the electrolysis was characterized by electronic spectroscopy. A mechanism for the formation of various dechlorinated products was investigated by using deuterium solvents and various spectroscopic measurements such as UV-VIS and the EPR spin-trapping technique.