| Identification | More | [Name]
P,P'-DDD | [CAS]
72-54-8 | [Synonyms]
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'-DDE
4,4'-DICHLORODIPHENYLDICHLOROETHANE
4,4'-TDE
DICHLORODIPHENYL DICHLOROETHANE
'LGC' (1127)
P,P'-DDD
P,P'-TDE
ROTHANE(R)
TDE
1,1’-(2,2-dichloroethylidene)bis(4-chloro-benzen
1,1’-(2,2-dichloroethylidene)bis(4-chloro-Benzene
1,1’-(2,2-dichloroethylidene)bis(4-chlorobenzene)
1,1-Dichloor-2,2-bis(4-chloor fenyl)-ethaan | [EINECS(EC#)]
200-783-0 | [Molecular Formula]
C14H10Cl4 | [MDL Number]
MFCD00000851 | [Molecular Weight]
320.04 | [MOL File]
72-54-8.mol |
| Chemical Properties | Back Directory | [Appearance]
TDE is a colorless, combustible, crystalline compound. | [Melting point ]
94-96 °C | [Boiling point ]
405.59°C (rough estimate) | [density ]
1.385 g/cm3 | [vapor density ]
11 | [vapor pressure ]
8.25, 12.2 at 25 °C (subcooled liquid vapor pressure calculated from GC retention time data,Hinckley et al., 1990) | [refractive index ]
1.6000 (estimate) | [Fp ]
11 °C | [storage temp. ]
APPROX 4°C
| [solubility ]
Chloroform: Slightly Soluble | [form ]
neat | [color ]
Crystalline white solid | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [Water Solubility ]
90ug/L(25 ºC) | [Merck ]
3061 | [BRN ]
1914072 | [Henry's Law Constant]
3.27 at 5 °C, 5.63 at 15 °C, 7.30 at 20 °C, 9.47 at 25 °C, 20.7 at 35 °C:in 3% NaCl solution: 3.95
at 5 °C, 7.70 at 15 °C, 15.8 at 25 °C, 27.6 at 35 °C (gas stripping-GC, Cetin et al., 2006) | [Major Application]
agriculture
environmental | [InChI]
1S/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 | [InChIKey]
AHJKRLASYNVKDZ-UHFFFAOYSA-N | [SMILES]
ClC(Cl)C(c1ccc(Cl)cc1)c2ccc(Cl)cc2 | [CAS DataBase Reference]
72-54-8(CAS DataBase Reference) | [EPA Substance Registry System]
p,p'-DDD (72-54-8) |
| Safety Data | Back Directory | [Hazard Codes ]
T,N,F | [Risk Statements ]
R21:Harmful in contact with skin.
R25:Toxic if swallowed.
R40:Limited evidence of a carcinogenic effect.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R11:Highly Flammable.
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S16:Keep away from sources of ignition-No smoking .
S7:Keep container tightly closed . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
KI0700000
| [HS Code ]
2903.99.8001 | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Oral
Acute Tox. 4 Dermal
Aquatic Acute 1
Aquatic Chronic 1
Carc. 2 | [Hazardous Substances Data]
72-54-8(Hazardous Substances Data) | [Toxicity]
EC50 (96-hour) for catfish <2.6 mg/L; LC50 (24-hour) for brown shrimp 6.8
μg/L (salt water); acute oral LD50 for rats 3,400 mg/kg (Verschueren, 1983), 113 mg/kg
(RTECS, 1985). |
| Hazard Information | Back Directory | [General Description]
A colorless crystalline solid. Insoluble in water and sinks in water. Toxic by inhalation, skin absorption or ingestion. Used as a pesticide. | [Reactivity Profile]
TDE is a halogenated hydrocarbon. Compounds in this group may react with acids, bases, and oxidizing and reducing agents. They are incompatible with alkali, and strong oxidizers, in particular. | [Air & Water Reactions]
Insoluble in water. | [Potential Exposure]
A potential danger to those involved in the manufacture, formulation and application of this insecticide. In an action of March 18, 1971, EPA cancelled all pesticide uses of this product which is a metabolite of DDT. Hence it is no longer manufactured commercially. | [Fire Hazard]
Special Hazards of Combustion Products: Irritating hydrogen chloride fumes may form in fires. | [First aid]
Skin Contact: Flood all areas of the body that have contacted the substance with water. Don’t wait to remove contaminated clothing; do it under the water stream. Use soap to help assure removal. Isolate contaminated clothing when removed to prevent contact by others. Eye Contact: Remove any contact lenses at once. Flush eyes well with copious quantities of water or normal saline for at least 20-30 minutes. Seek medical attention. Inhalation: Leave contaminated area immediately; breathe fresh air. Proper respiratory protection must be supplied to any rescuers. If coughing, difficult breathing or any other symptoms develop, seek medical attention at once, even if symptoms develop many hours after exposure. Ingestion: If convulsions are not present, give a glass or two of water or milk to dilute the substance. Assure that the person’s airway is unobstructed and contact a hospital or poison center immediately for advice on whether or not to induce vomiting. Medical observation is recommended following acute overexposure. | [Shipping]
UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN2761 Organochlorine pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. | [Incompatibilities]
Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. | [Description]
DDD is a banned and obsolete insecticide that is also a metabolite of DDT. It is practically insoluble in water and is not highly volatile. It is, like DDT, very environmentally persistent in both soils and water. It is toxic to humans through ingestion, inhalation and via skin absorption and has been linked with cancer, is mutagenic and various negative reproduction/fertility effects. It is also an endocrine disrupter. It is toxic to most animal species but data is not abundant. | [Chemical Properties]
colourless to off-white crystals | [Chemical Properties]
TDE is a colorless, combustible, crystalline compound. | [Waste Disposal]
Incineration in a unit operating above 850℃ equipped with HCl scrubber. Incineration above 1200℃ for 1-2 seconds is recommended. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office. | [Uses]
4,4'-Dichlorodiphenyldichloroethane is a synthetic organochlorine insecticide. 4,4'-Dichlorodiphenyldichloroethane is a metabolite of 4,4'-Dichlorodiphenyltrichloroethane (D434195). 4,4'-Dichlorodiphenyldichloroethane is a probable carcinogen (Group B2). | [Uses]
Contact control of leaf rollers and other insects on vegetables and tobacco | [Definition]
ChEBI: A chlorophenylethane that is 2,2-bis(p-chlorophenyl)ethane substituted by two chloro groups at position 1. It is a metabolite of the organochlorine insecticide, DDT. | [Production Methods]
The commercial production of DDD typically involves the reduction of DDT under controlled chemical conditions. This process uses metallic reducing agents such as zinc dust in an acidic medium, often acetic acid or hydrochloric acid, to remove one chlorine atom from the trichloromethyl group of DDT, converting it into the dichloromethyl group found in DDD. The reaction is carried out under reflux to ensure complete conversion, followed by purification steps like distillation or recrystallisation to isolate the DDD compound. | [Hazard]
Toxic by ingestion, inhalation, and skin
absorption; use restricted in some states. Questionable
carcinogen. | [Health Hazard]
A derivative of DDT; toxic properties similar to DDT; systemic effects from ingestion include headache, anesthesia, cardiacarrhythmias, nausea, vomiting, sweating,and convulsions; oral lethal dose in mice600 mg/kg; also moderately toxic by skinabsorption; susceptible to accumulation infat; sufficient evidence of carcinogenicity inexperimental animals.
LD50 oral (rat): 113 mg/kg
LD50 skin (rabbit): 1200 mg/kg. | [Mechanism of action]
Non-systemic stomach and contact action. Sodium ion channel blocker | [Safety Profile]
Confirmed carcinogen withexperimental carcinogenic, neoplastigenic, andtumorigenic data. Poison by ingestion. Moderately toxicby skin contact. Mutation data reported. An insecticide.When heated to decomposition it emits toxic fumes ofCl-. | [Environmental Fate]
Biological. It was reported that p,p′-DDD, a major biodegradation product of p,p′-
DDT, was degraded by Aerobacter aerogenes under aerobic conditions to yield 1-chloro-
2,2-bis(p-chlorophenyl)ethylene, 1-chloro-2,2-bis-(p-chlorophenyl)ethane and 1,1-bis(pchlorophenyl)ethylene. Under anaerobic conditions, however, four additional compounds
were identified: bis(p-chlorophenyl)acetic acid, p,p′-dichlorodiphenylmethane, p,p′-
dichlorobenzhydrol and p,p′-dichlorobenzophenone (Fries, 1972). Under reducing conditions, indigenous microbes in Lake Michigan sediments degraded DDD to 2,2-bis(pchlorophenyl)ethane and 2,2-bis(p-chlorophenyl)ethanol (Leland et al., 1973). Incubation
of p,p′-DDD with hematin and ammonia gave 4,4′-dichlorobenzophenone, 1-chloro-2,2-
bis-(p-chlorophenyl)ethylene and bis(p-chlorophenyl)acetic acid methyl ester (Quirke et
al., 1979). Using settled domestic wastewater inoculum, p,p′-DDD (5 and 10 mg/L) did
not degrade after 28 days of incubation at 25°C (Tabak et al., 1981).
Chemical/Physical. The hydrolysis rate constant for p,p′-DDD at pH 7 and 25°C was
determined to be 2.8 × 10–6/hour, resulting in a half-life of 28.2 years (Ellington et al.,
1987). 2,2-Bis(4-chlorophenyl)-1-chloroethene and hydrochloric acid were | [Purification Methods]
Crystallise DDD from EtOH and dry it in vacuo. The purity is checked by TLC. [Beilstein 5 III 1830.] TOXIC INSECTICIDE. | [Toxics Screening Level]
The initial risk screening level (IRSL) is 0.01 μg/m3 with an annual averaging time. | [Pesticide Type]
Insecticide; Metabolite |
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J & K SCIENTIFIC LTD.
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Spectrum Chemical Manufacturing Corp.
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