72-54-8

Basic information

• Product Name: 1,1-Bis(4-chlorophenyl)-2,2-dichloroethane
• Synonyms: Ethane,1,1-dichloro-2,2-bis(p-chlorophenyl)- (8CI);1,1-Bis(4-chlorophenyl)-2,2-dichloroethane; 1,1-Bis(p-chlorophenyl)-2,2-dichloroethane;1,1-Dichloro-2,2-bis(4-chlorophenyl)ethane;1,1-Dichloro-2,2-bis(p-chlorophenyl)ethane;2,2-Bis(4-chlorophenyl)-1,1-dichloroethane;2,2-Bis(p-chlorophenyl)-1,1-dichloroethane; 4,4'-DDD;4,4'-Dichlorodiphenyldichloroethane; 4,4'-TDE; DDD;Dichlorodiphenyldichloroethane; Dilene; ME 1700; NSC 8941; Rhothane; TDE;p,p'-DDD; p,p'-Dichlorodiphenyldichloroethane; p,p'-Dichlorodiphenylethylenedichloride; p,p'-TDE
• CAS NO: 72-54-8
• Molecular Formula: C₁₄H₁₀Cl₄
• Molecular Weight: 320.04
• EINECS: 200-783-0
• Mol File: 72-54-8.mol

Chemical Properties

• Melting Point: 109-111℃
• Boiling Point: 193 C
• Appearance: colourless to off-white crystals
• Density: 1.385 g/cm3
• CAS DataBase Reference: 1,1-Bis(4-chlorophenyl)-2,2-dichloroethane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-Bis(4-chlorophenyl)-2,2-dichloroethane(72-54-8)
• EPA Substance Registry System: 1,1-Bis(4-chlorophenyl)-2,2-dichloroethane(72-54-8)

Safety Data

• Hazard Codes: T:Toxic
• Statements: R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
• Safety Statements: S23:Do not inhale gas/fumes/vapour/spray.; S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 72-54-8(Hazardous Substances Data)

Usage

Uses

Used in Pest Control Applications:
DDT is used as an insecticide for its ability to disrupt the nervous systems of insects, making it an effective tool for controlling pests such as mosquitoes and agricultural pests. Its effectiveness in pest control has historically been significant in protecting crops and reducing the spread of vector-borne diseases.
Used in Public Health:
In some regions, DDT is still used as a public health measure for the control of malaria-carrying mosquitoes. Despite its environmental persistence and potential ecological impact, the need to combat malaria in certain areas has led to its continued use in specific vector control programs.
Used in Historical Agricultural Practices:
DDT was once widely used in agriculture as a means to protect crops from various pests. Its effectiveness in this context contributed to increased crop yields and reduced losses due to insect damage. However, due to its persistence in the environment and the accumulation of its residues in the food chain, leading to harmful effects on wildlife, its use in agriculture has been largely discontinued in many countries.

InChI:InChI=1/C14H10Cl4/c15-11-5-1-9(2-6-11)13(14(17)18)10-3-7-12(16)8-4-10/h1-8,13-14H

Upstream product

• 60-29-7 diethyl ether 
• 50-29-3 p,p'-DDT 
• 64-17-5 ethanol 
• 619-33-0 dichloroacetaldehyde diethyl acetal 
• 108-90-7 chlorobenzene 
• 79-02-7 2,2-dichloroacetaldehyde 
• 41521-04-4 2,2-dichloro-1-(4-chlorophenyl)ethanol 
• 35166-78-0 cyclohexylmethyl magnesium bromide 
• 2387-16-8 1,1-dichloro-2,2-diphenylethane 
• 7647-01-0 hydrogenchloride 
• 67-56-1 methanol 
• 5157-57-3 2,2-dichloro-1-(4-chlorophenyl)ethanone 
• 15226-74-1 dicobalt octacarbonyl 
• 109-89-7 diethylamine 

Downstream Products

• 1022-22-6 1-chloro-2,2-bis(p-chlorophenyl)ethylene 
• 3547-04-4 1,1-bis(4-chlorophenyl)ethane 
• 5121-74-4 4,4'-dichlorostylbene 
• 1820-42-4 bis(4-chlorophenyl)acetylene 
• 16740-47-9 meso-4.4'.α.α'-tetrachloro-bibenzyl 
• 183430-89-9 2,2-dichloro-1,1-bis(4-chloro-3-nitrophenyl)ethane 
• 33406-60-9 1,1-dichloro-2,2-bis-(4-chloro-3,5-dinitro-phenyl)-ethane 
• 24337-12-0 2-(4,4'-dichloro-benzhydryl)-[1,3]dioxolane 
• 101-76-8 4,4'-dichlorodiphenylmethane 
• 2510-74-9 (E)-1,2-di(4-chlorophenyl)ethene 
• 76905-73-2 (E)-4,4'-(1-chloroethene-1,2-diyl)bis(chlorobenzene) 
• 92907-89-6 1,1-Di-(4-chlor-phenyl)-2-(2-hydroxy-ethyoxy)-ethylen 
• 83-05-6 bis(4'-chlorophenyl)acetic acid 
• 90-97-1 4,4'-dichlorobenzophenone 

Relevant articles and documents

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.

Photosensitizing catalysis of the B12 complex without an additional photosensitizer

A cobalamin derivative, heptamethyl cobyrinate perchlorate, was activated by UV light irradiation to form a Co(i) species in the presence of triethanolamine and used for a dechlorination reaction, and this photochemical reaction was accelerated in an ionic liquid.

A polymerized ionic liquid-supported B12 catalyst with a ruthenium trisbipyridine photosensitizer for photocatalytic dechlorination in ionic liquids

By immobilizing a B12 complex and a Ru(ii) trisbipyridine photosensitizer in a polymerized ionic liquid (PIL), a visible light-driven photocatalyst was developed. The synthesized copolymer was characterized by GPC and DLS, and using UV-vis absorption spectra and luminescence spectra. The Ru(ii) trisbipyridine photosensitizer in the copolymer showed an enhanced emission compared to that of the monomer in the ionic liquid, 1-butyl-4-methylimidazolium bis(trifluoromethanesulfonyl)amide ([C 4mim][NTf2]). Formation of the Co(i) species of the B 12 complex in the copolymer was confirmed by the UV-vis spectral change in [C4mim][NTf2] containing a sacrificial reductant (triethanolamine) under irradiation with visible light. The copolymer showed a high photocatalytic activity in various ionic liquids for 1,1-bis(4- chlorophenyl)-2,2,2-trichloroethane (DDT) dechlorination with ～99% conversion after visible light irradiation for 2 h. Furthermore, both the B 12 catalyst and photosensitizer in the polymer were easily recycled for use with the ionic liquid solvent without any loss of catalytic activity.

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.

Synthesis of a B12-BODIPY dyad for B12-inspired photochemical transformations of a trichloromethylated organic compound

A B12complex-BODIPY dyad was synthesized by peripheral modification of cobalamin derivatives. The photophysical properties of the dyad were investigated by UV-vis, PL, and transient absorption spectroscopy. A visible light-driven dechlorination reaction of a trichlorinated organic compound, DDT, was reported. The dyad showed efficient catalysis for dechlorination under N2with turnover numbers of over 220 for the reaction. One-pot syntheses of an ester and amide from DDT and benzotrichloride were also achieved using the dyad under air.

Enhanced photocatalytic activity of a B12-based catalyst co-photosensitized by TiO2 and Ru(II) towards dechlorination

A novel hybrid photocatalyst denoted as B12-TiO2-Ru(ii) was prepared by co-immobilizing a B12 derivative and trisbipyridine ruthenium (Ru(bpy)32+) on the surface of a mesoporous anatase TiO2 microspheres and was characterized by DRS, XRD, SEM and BET et al. By using the hybrid photocatalyst, DDT was completely didechlorinated and a small part of tridechlorinated product was also detected in the presence of TEOA only after 30 min of visible light irradiation. Under simulated sunlight, the hybrid exhibited a significantly enhanced photocatalytic activity for dechlorination compared with B12-TiO2 under the same condition or itself under visible light irradiation due to the additivity in the contribution of UV and visible part of the sunlight to the electron transfer. In addition, this hybrid catalyst can be easily reused without loss of catalytic efficiency. This is the first report on a B12-based photocatalyst co-sensitized by two photosensitizers with wide spectral response.

Significant enhancement of visible light photocatalytic activity of the hybrid B12-PIL/rGO in the presence of Ru(bpy)32+ for DDT dehalogenation

A new B12-PIL/rGO hybrid was prepared successfully through immobilizing a B12 derivative on the surface of poly(ionic liquid) (PIL)-modified reduced graphene oxide (rGO) by electrostatic attraction and π-π stacking attraction among the different components. The hybrid catalyst showed an enhanced photocatalytic activity in the presence of Ru(bpy)32+ for 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethane (DDT) dechlorination with ～100% conversion. Especially, the yield of didechlorinated products could reach 78% after 1 h of visible light irradiation, which should be attributed to a synergistic effect of B12, rGO and PIL in B12-PIL/rGO, including their respective catalytic performance, the excellent electron transport of rGO and the concentration of DDT and 1,1-bis(4-chlorophenyl)-2,2-dichloroethane (DDD) on the surface of B12-PIL/rGO. Furthermore, the hybrid catalyst was easily recycled for use without obvious loss of catalytic activity.

Photocatalytic function of the B12 complex with the cyclometalated iridium(III) complex as a photosensitizer under visible light irradiation

A visible light induced three-component catalytic system with the cobalamin derivative (B12) as a catalyst, the cyclometalated iridium(iii) complex (Irdfppy, Irppy, Irpbt and [Ir{dF(CF3)ppy}2(dtbpy)]PF6) as a photosensitizer and triethanolamine as an electron source under N2 was developed. This catalytic system showed a much higher catalytic efficiency than the previous catalytic system using [Ru(ii)(bpy)3]Cl2 as the photosensitizer for the dechlorination reaction of 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethane (DDT). Noteworthy is the fact that the remarkable high turnover number (over ten thousand) based on B12, which ranks at the top among the reported studies, was obtained when Irdfppy was used as a photosensitizer. This photocatalytic system was also successfully applied to the B12 enzyme-mimic reaction, i.e., the 1,2-migration of the phenyl group of 2-bromomethyl-2-phenylmalonate. The plausible reaction mechanism was proposed, which involved two quenching pathways, an oxidative quenching pathway and a reductive quenching pathway, to be responsible for the initial electron transfer of the excited-state photosensitizers during the DDT dechlorination reaction. Transient photoluminescence experiments revealed that the oxidative quenching of the photosensitizer dominated over the reductive quenching pathway.

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.

Supramolecular system composed of B12 model complex and organic photosensitizer: Impact of the corrin framework of B12 on the visible-light-driven dechlorination without the use of noble metals

The visible-light-driven dechlorination system without the use of a noble metal has been developed. We screened the combination of cobalt catalysts having square-planar monoanionic ligands (hydrophobic B12 model complex 1/imine-oxime type complex 2) and typical red dyes (Rose Bengal 3/Rhodamine B 4/Nile Red 5) for the construction of a dehalogenation system via a noble-metal-free and visible-light-driven process. The combination of the hydrophobic B12 model complex 1 and Rose Bengal 3 exhibited the highest catalytic activity to 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethane (DDT) to form the monodechlorinated compound, 1,1-bis(4-chlorophenyl)-2,2-dichloroethane, as the major product. The prolonged photocatalysis of DDT by the B12-Rose Bengal system afforded the tri-dechlorinated compound, trans-4,4′-dichlorostilbene, as the major product. Furthermore, we investigated the mechanism of the dehalogenation cycle using various methods such as UV-vis spectroscopy and laser flash photolysis. Finally, we clarified the advantage of using the hydrophobic B12 model complex 1 as an electron acceptor as well as a cobalt catalyst in the organic dye-involved photocatalysis.