| Product Name: | ENDRIN | | Synonyms: | (1aalpha,2beta,2abeta,3alpha,6alpha,6abeta,7beta,7aalpha)-3,4,5,6,9,9-hexachlo;3,4,5,6,9,9-hexachloro-[1aalpha,2beta,2abeta,3alpha,6alpha,6abeta,7;3,4,5,6,9,9-Hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphth(2,3-b)oxirene;4:5,8-Dimethanonaphthalene,1,2,3,4,10,10-hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-,endo,e1;5,6,9,9-hexachloro-1aalpha,2beta,2abeta,3alpha,6alpha,6abeta,7beta,7aalpha-4;beta,7aalpha]octahydro-2,7:3,6-dimethanonaph[2,3-b]oxirene;Cmpd. 269;Compd. 269 | | CAS: | 72-20-8 | | MF: | C12H8Cl6O | | MW: | 380.91 | | EINECS: | 200-775-7 | | Product Categories: | Oeko-Tex Standard 100;Pesticides;Pesticides&Metabolites;PesticidesMethod Specific;EA - EOInternational Standards;NIOSH 5519: Analysis of Endrin in Indoor AirMethod Specific;NIOSH and OSHA Methods;CyclodienesAlphabetic;2000/60/EC;2000/60/ECMore...Close...;Alpha sort;AvicidesPesticides;CyclodienesPesticides&Metabolites;E;EA - EOMethod Specific;E-GAlphabetic;European Community: ISO and DIN;Insecticides;Baby Food Directives 13/2003 EC&14/2003 ECPesticides;AvicidesMethod Specific | | Mol File: | 72-20-8.mol |  |
| | ENDRIN Chemical Properties |
| Melting point | 245℃ (Decomposition) | | Boiling point | 496.11°C (rough estimate) | | density | 1.7 g/cm3 | | vapor pressure | 2 x 10-7 mmHg at 25 °C (ACGIH, 1986) | | refractive index | 1.5550 (estimate) | | Fp | 11 °C | | storage temp. | APPROX 4°C | | Water Solubility | 0.25mg/L(25 ºC) | | Merck | 13,3612 | | Henry's Law Constant | 1.78 at 5 °C, 2.96 at 15 °C, 4.54 at 20 °C, 5.63 at 25 °C, 8.68 at 35 °C:in 3% NaCl solution: 5.13
at 5 °C, 9.47 at 15 °C, 18.8 at 25 °C, 19.7 at 35 °C (gas stripping-GC, Cetin et al., 2006) | | Exposure limits | NIOSH REL: TWA 0.1 mg/m3, IDLH 2 mg/m3; OSHA PEL: TWA 0.1
mg/m3; ACGIH TLV: TWA 0.1 mg/m3. | | Stability: | Stable. Incompatible with strong acids, strong oxidizers. Corrodes some metals. | | IARC | 3 (Vol. 5, Sup 7) 1987 | | EPA Substance Registry System | Endrin (72-20-8) |
| | ENDRIN Usage And Synthesis |
| Chemical Properties | Endrin is the common name of one member
of the cyclodiene group of pesticides. It is a cyclic hydrocarbon having a chlorine-substituted, methano-bridge structure. Endrin is a white, crystalline solid | | Chemical Properties | Endrin is an organochlorine compound. Endrin appears as a stable, white or beige crystalline
solid. It is incompatible with strong acids and strong oxidizers and corrodes some
metals.Endrin decomposes on heating above 245°C producing hydrogen chloride, phosgene. In
fact, the US EPA has sharply restricted the availability and uses of many organochlorine
groups of pesticides. These include DDT, aldrin, dieldrin, endrin, heptachlor, mirex, chlordecone,
and chlordane, while many other organochlorines, however, remain the active
ingredients of various home and garden products and some agricultural, structural, and
environmental pest control products. | | Chemical Properties | Endrin is an organochlorine compound. Endrin appears as a white or beige crystalline solid and is stable. It is incompatible with strong acids and strong oxidisers and corrodes some metals. Endrin decomposes on heating above 245°C, producing hydrogen chloride and phosgene. Endrin is incompatible with strong oxidisers, strong acids, and parathion and emits hydrogen chloride and phosgene when heated or burned. | | Physical properties | White, crystalline solid when pure; light tan color with faint chemical odor for technical grades.
Odor threshold concentrations in air ranged from 18 to 41 ppb (quoted, Keith and Walters, 1992).
Robeck et al. (1965) reported an odor threshold concentration of 9 ppb. | | Uses | All uses of endrin in the United States
were canceled by the manufacturer in 1986;
formerly used as an insecticide, avicide, and
rodenticide | | Uses | Formerly as insecticide. | | Definition | A stereoisomer of dieldrin which is the endo, exo
isomer. | | General Description | ENDRIN is a white crystalline, odorless solid dissolved in a liquid carrier. ENDRIN is water emulsifiable. ENDRIN is toxic by inhalation, skin absorption, and/or ingestion. When heated or burned ENDRIN may emit toxic hydrogen chloride and phosgene. ENDRIN is used as a pesticide. | | Reactivity Profile | While a mixture of parathion and ENDRIN was being blended into a petroleum solvent, an exothermic reaction occurred that caused some of the petroleum solvent to vaporize. The solvent-vapor-air mixture exploded. The mechanical agitation possibly initiated the exothermic reaction, Doyle(1973). Toxic hydrogen chloride and phosgene may be generated when solution burns. Avoid strong oxidizers, strong acids and parathion. [EPA, 1998]. | | Hazard | Toxic by inhalation and skin absorption,
use may be restricted. Headache, liver damage, and
central nervous system impairment. Questionable
carcinogen. | | Health Hazard | Extremely toxic to experimental animals byall routes of exposure; also, highly toxic tohumans and animals by ingestion or skinabsorption; toxic effects similar to those ofaldrin and dieldrin; symptoms — headache,dizziness, nausea, vomiting, abdominal pain,insomnia, confusion, stupor, convulsions,tremors, rise in blood pressure, fever, frothing of mouth, deafness, coma, and respiratoryfailure; stimulant to central nervous system;ingestion of 50–60 mg can produce toxicsymptoms in human; can produce adversereproductive effects; a teratogenic substance;evidence of carcinogenicity in experimental animals and humans inadequate; oralLD50 value (mice): ～13 mg/kg, (guinea pig):16 mg/kg; U.S. EPA listed extremely hazardous substance; exposure limit: PEL/TLV TWA(skin) 0.1 mg/kg (OSHA, ACGIH). | | Health Hazard | Exposures to endrin cause toxicity and adverse health effects. Endrin is highly toxic to
humans and species of animal. The symptoms of poisoning include, but are not limited
to, headache, dizziness, nausea, vomiting, incoordination, tremor, mental confusion, and
hyperexcitable state. Exposures to very high concentrations of endrin and in severe cases
of poisoning, symptoms include convulsions, seizures, coma, and respiratory depression.
In severe organochlorine compound poisoning, symptoms include myoclonic jerking
movements, generalized tonic-clonic convulsions, respiratory depression following the
seizures, and coma. | | Health Hazard | ENDRIN is extremely toxic. It is rapidly absorbed through the skin. Symptoms appear between 20 minutes and 12 hours after exposure. There is evidence that ENDRIN may cause chromosomal damage. Doses of 1 mg/kg can cause symptoms. It is a suspected carcinogen. Also, it is a central nervous system depressant and hepatotoxin. Pregnant women are considered to be at special risk. | | Fire Hazard | Toxic hydrogen chloride and phosgene may be generated when solution burns. Avoid strong oxidizers, strong acids and parathion. | | Agricultural Uses | Insecticide, Avicide: Not approved for use in EU countries. A U.S.
EPA restricted Use Pesticide (RUP). It is a persistent and
acutely toxic insecticide. Endrin is an insecticide which
has been used to control insects, rodents, and birds, mainly
on field crops such as cotton, maize, sugarcane, rice, cereals,
ornamentals, and other crops. It has also been used
for grasshoppers in non-cropland and to control voles and
mice in orchards. Once widely used in the U.S., most uses
were canceled in 1980 and it has not been produced nor
sold in the U.S. since 1986. It is not easily dissolved in
water and can remain in the soil for more than 14 years. | | Trade name | COMPOUND 269®; EN 57®;
ENDREX®; ENDRICOL®; ENDRIN CHLORINATED
HYDROCARBON INSECTICIDE®; HEXADRIN®;
MENDRIN®; NENDRIN®; OKTANEX® | | Safety Profile | Poison by ingestion,
skin contact, and intravenous routes.
Experimental teratogenic and reproductive
effects. Questionable carcinogen. Mutation
data reported. A central nervous system
stimulant. Highly toxic to birds, fish, and
humans. Many cases of fatal poisoning have
been attributed to it. Does not accumulate
in human tissue. In humans, ingestion of 1
mg/kg has caused symptoms. A dangerous
fire hazard. Mixtures with parahon dlssolve
very exothermically in petroleum solvents
and may cause an air-vapor explosion. See
also ALDFUN. | | Potential Exposure | A potential danger to those involved in
manufacture, formulation and field application of this insecticide, avicide, and rodenticide. Pesticide not in use; TRI and/
or IUR indicates importers or manufacturers are unlikely. | | First aid | If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contactsthe skin, remove contaminated clothing and wash immediately with soap and water. Speed in removing materialfrom skin is of extreme importance. Shampoo hairpromptly if contaminated. Seek medical attention immediately. If this chemical has been inhaled, remove fromexposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing hasstopped and CPR if heart action has stopped. Transferpromptly to a medical facility. When this chemical hasbeen swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit | | Environmental Fate | Biological. In four successive 7-day incubation periods, endrin (5 and 10 mg/L) was
recalcitrant to degradation in a settled domestic wastewater inoculum (Tabak et al., 1981).
Soil. Microbial degradation of endrin in soil formed several ketones and aldehydes of
which keto-endrin was the only metabolite identified (Kearney and Kaufman, 1976). In
eight Indian rice soils, endrin degraded rapidly to low concentrations after 55 days.
Degradation was highest in a pokkali soil and lowest in a sandy soil (Gowda and Sethunathan,
1976).
Under laboratory conditions, endrin degraded to other compounds in a variety of soils
maintained at 45°C. Except for Rutledge sand, endrin disappeared or was transformed in
the following soils after 24 hours: Lynchburg loamy sand, Magnolia sandy loam, Magnolia
sandy clay loam, Greenville sandy clay and Susquehanna sandy clay. No products were
identified (Bowman et al., 1965).
The disappearance half-lives for endrin in field soils under flooded and nonflooded
conditions were 130 and 468 days, respectively (Guenzi et al., 1971). The average disappearance
half-life in flooded soils under laboratory conditions was 31 days (Gowda and
Sethunathan, 1976, 1977).
The percentage of endrin remaining in a Congaree sandy loam soil after 14 years was
41% (Nash and Woolson, 1967).
Groundwater. According to the U.S. EPA (1986) endrin has a high potential to leach
to groundwater.
Plant. In plants, endrin is converted to the corresponding sulfate (Hartley and Kidd,
1987).
Surface Water. Algae isolated from a stagnant fish pond degraded 24.4% of the applied
endrin to ketoendrin (Patil et al., 1972).
Photolytic. Photolysis of thin films of solid endrin using UV light (l = 254 nm)
produced d-ketoendrin, endrin aldehyde and other compounds (Rosen et al., 1966). Endrin
exposed to a hot California sun for 17 days completely isomerized to d-ketoendrin or 1,8-
exo-9,10,11,11-hexachlorocyclo[6.2.1.13,6.02,7.04,10]dodecan-5-one (Burton and Pollard,
1974). Irradiation of endrin by UV light (l = 253.7 nm and 300 nm) or by natural sunlight
in cyclohexane and n-hexane solution resulted in an 80% yield of 1,8-exo-9,11,11-pentachloropentacyclo[
6.2.1.13,6.02,7.04,10]dodecan-5-one (Zabik et al., 1971). When an aqueous
solution containing endrin was photooxidized by UV light at 90–95°C, 25, 50 and
75% degraded to carbon dioxide after 15.0, 41.0 and 172.0 hours, respectively (Knoevenagel
and Himmelreich, 1976).
Chemical/Physical. At 230°C, endrin isomerizes to an aldehyde and a ketone. When
heated to decomposition, hydrogen chloride and phosgene may be released (NIOSH, 1994)
but residues containing an aldehyde (15–20%), a ketone (55–60%), a caged alcohol (5%),
and other volatile products (15–20%) were reported (Phillips et al., 1962).
In water, endrin will undergo nucleophilic attack at the epoxide moiety forming endrin
diol (Kollig, 1993).
At 50°C, endrin was not unaffected by the oxidants chlorine, permanganate and
persulfate (Leigh, 1969). | | Solubility in organics | At 25 °C: acetone (170 g/L), benzene (138 g/L), carbon tetrachloride (33 g/L), hexane (71 g/L), xylene (183 g/L)
(Windholz et al., 1983). Soluble in aromatic hydrocarbons, esters, and ketones (ITII, 1986). | | Solubility in water | At 25 °C: acetone (170 g/L), benzene (138 g/L), carbon tetrachloride (33 g/L), hexane (71 g/L), xylene (183 g/L)
(Windholz et al., 1983). Soluble in aromatic hydrocarbons, esters, and ketones (ITII, 1986). | | Shipping | UN2761 Organochlorine pesticides, solid, toxic,
Hazard Class: 6.1; Labels: 6.1-Poisonous materials | | Toxicity evaluation | Endrin (40) is 1,2,3,4,10,10-hexachloro-
1,4,4a,5,8,8a-hexahydro-6,7-epoxy-1,4-endo,endo-
5,8-dimethanonaphthalene (mp 245 dec, vp 0.022 mPa at
25 ?C) and is soluble in water to 23 μg/L. This compound is
the endo,endo isomer of dieldrin, which is less stable and
more toxic than dieldrin with rat LD50 values of 17.8 and
7.5 (oral) and 15 (dermal) mg/kg. It was used as a cotton
insecticide, but because of its high toxicity to fish, its use
was restricted. | | Incompatibilities | Incompatible with strong 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 (forms explosive vapors),
oxoacids, epoxides, and parathion. Slightly corrosive to
metal | | Waste Disposal | A disposal procedure recommended by the manufacturer consists of absorption, if
necessary, and burial at least 18 in deep; preferably in
sandy soil in a flat or depressed location away from
wells, livestock, children, wildlife, etc. Incineration is the
recommended method. Consult with environmental
regulatory agencies for guidance on acceptable disposal
practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations
governing storage, transportation, treatment, and waste
disposal. 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. | | Precautions | Students and occupational workers should be careful during handling of endrin. Workers
should not wash away the chemical waste into the sewer, but sweep spilled chemical substance
into sealable containers. Workers should use extra personal protection, face shield
and eye protection, a chemical protection suit, and self-contained breathing apparatus.
Exposures to endrin cause effects on the CNS leading |
| | ENDRIN Preparation Products And Raw materials |
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