Dichloroacetaldehyde
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Dichloroacetaldehyde
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CAS No:
79-02-7
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Formula:
C2H2Cl2O
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Chemical Name:
Dichloroacetaldehyde
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Synonyms:
Acetaldehyde,2,2-dichloro-;Acetaldehyde,dichloro-;2,2-Dichloroacetaldehyde;Dichloroacetaldehyde;Chloroaldehyde;α,α-Dichloroacetaldehyde;NSC 5207
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CAS No:
Description
PHYSICAL DESCRIPTION: Colorless liquid with a penetrating pungent odor. (NTP, 1992)
Dichloroacetaldehyde is a colorless liquid with a penetrating pungent odor. (NTP, 1992)
Dichloroacetaldehyde is a colorless liquid with a penetrating pungent odor. (NTP, 1992)|2,2-Dichloroacetaldehyde is an organochlorine compound.
Dichloroacetaldehyde Basic Attributes
112.937
112.94
201-169-5
9GT3DHH725
5207
1993
DTXSID3021560
COLORLESS LIQ
Characteristics
17.1
0.98900
Dichloroacetaldehyde is a colorless liquid with a penetrating pungent odor. (NTP, 1992)
1.436 g/cm3 @ Temp: 25 °C
-37.6--37.4 °C
89.2 °C
60 DEG C CC
1.429
soluble in water and common organic solvents.
55.4 mm Hg @ 25 deg C
3.9 (NTP, 1992) (Relative to Air)
PENETRATING PUNGENT ODOR
2.30e-12 cm3/molecule*sec
WT/GAL 12.1 LB|Reacts with water and alcohols to form hydrates and hemi-acetals /From table/|Forms hydrate in water.|Crystalizes from water; melting point: 35-50 °C; boiling point: 85-95 °C; specific gravity: 1.53-1.54 at 20 °C/4 °C; vapor pressure: ca. 6.5 kPa @ 20 °C; ca. 25 kPa @ 50 °C; soluble in polar organic solvent, insoluble in nonpolar organic solvents. /Dichloroacetaldehyde monohydrate/|Forms a solid, colorless polymer on standing which depolymerizes if heated to 120 °C.
Highly flammable.
Aldehydes
Highly Flammable
DICHLOROACETALDEHYDE polymerizes on standing or in the presence of acid. This compound reacts with acids, oxidizers. (NTP, 1992)
Safety Information
III
3.2
UN 1992
P201, P202, P260, P261, P262, P264, P270, P271, P273, P280, P281, P284, P301+P310, P301+P330+P331, P302+P350, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P320, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501
H301
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
... It can react vigorously with oxidizing materials.
Ramel C et al; An Evaluation of the Genetic Toxicity of Dichlorvos; Mutat Res 76 (3): 297-309 (1980)
This compound is combustible. (NTP, 1992)
|Danger|H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501|Aggregated GHS information provided by 2 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P262, P264, P270, P271, P273, P280, P281, P284, P301+P310, P301+P330+P331, P302+P350, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P320, P321, P322, P330, P361, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this chemical in a freezer and away from all organic compounds. (NTP, 1992)
MINIMUM PROTECTIVE CLOTHING: When working with this chemical, you should wear an impervious full-body suit equipped with an air line respirator or a self-contained breathing apparatus. RECOMMENDED RESPIRATOR: When working with this chemical, wear a NIOSH-approved full face chemical cartridge respirator equipped with the appropriate organic vapor cartridges. If that is not available, a half face respirator similarly equipped plus airtight goggles can be substituted. However, please note that half face respirators provide a substantially lower level of protection than do full face respirators. RECOMMENDED GLOVE MATERIALS: Permeation data indicate that nitrile gloves may provide protection to contact with this compound. Nitrile over latex gloves is recommended. However, if this chemical makes contact with your gloves, or if a tear, hole or puncture develops, remove them at once. (NTP, 1992)
MODERATE FIRE HAZARD|Combustible
To fight fire, use water, foam, carbon dioxide, dry chemical.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
... Strong skin irritant.
Dichloroacetaldehyde is produced in pulp mill bleaching operations and has been identified in pulp mill effluents(1).
Toxicity
If chloroacetaldehydes are released during manufacture or use, they are probably released as air emissions and in discharged water. /Di- and tri-chloroacetaldehydes/|Dichloroacetaldehyde's production and use as a chemical intermediate(1) and its formation during the pulp bleaching process(2) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4.3(SRC), determined from a structure estimation method(2), indicates that dichloroacetaldehyde is expected to have very high mobility in soil(SRC). Volatilization of dichloroacetaldehyde from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.42X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The potential for volatilization of dichloroacetaldehyde from dry soil surfaces may exist(SRC) based upon its vapor pressure of 55.4 mm Hg(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4.3(SRC), determined from a structure estimation method(2), indicates that dichloroacetaldehyde would not be expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 8.42X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Volatilization half-lives for a model river and model lake are 4.7 and 38 days, respectively(SRC), using an estimation method(3). According to a classification scheme(5), an estimated BCF of 3.2(3,SRC), from an estimated log Kow(6,SRC) suggests the potential for bioconcentration in aquatic organisms is low(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dichloroacetaldehyde, which has a vapor pressure of 55.4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dichloroacetaldehyde is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is 7.0 days(SRC) from its rate constant of 2.3X10-12 cu cm/molecule-sec(3).
The rate constant for the vapor-phase reaction of dichloroacetaldehyde with photochemically-produced hydroxyl radicals is 2.3X10+12 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of 7.0 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(SRC). Dichloroacetaldehyde contains an alkyl chloride group which is potentially hydrolyzable(2). No information is available on its hydrolysis rate. Dichloroacetaldehyde is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum.
An estimated BCF of 3.2 was calculated for dichloroacetaldehyde(SRC), using an estimated log Kow of 0.27(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.
Using a structure estimation method based on molecular connectivity indices(1), the Koc for dichloroacetaldehyde can be estimated to be 4.3(SRC). According to a classification scheme(2), this estimated Koc value suggests that dichloroacetaldehyde is expected to have very high mobility in soil.
The Henry's Law constant for dichloroacetaldehyde is estimated as 8.42X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dichloroacetaldehyde is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 4.7 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 38 days(SRC). Dichloroacetaldehyde's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of dichloroacetaldehyde from dry soil surfaces may exist(SRC) based upon its vapor pressure of 55.4 mm Hg at 25 °C(3).
Dichloroacetaldehyde is toxic by ingestion or inhalation.
Drug Information
DICHLOROACETALDEHYDE IS A PRESUMED METABOLITE OF THE INSECTICIDES, DICHLORVOS & TRICHLORFON.|Mice were injected with dichloroacetaldehyde hydrate (8 mg, ipr). Analysis of the 24 hr urinary metabolites did not reveal any chlorinated compounds apart from traces of dichloroacetic acid. This acid was present as 1% of the applied dose.|In mammals, chloroacetaldehydes are rapidly reduced to chloroethanols and/or oxidized to chloroacetic acids. /Chloroacetaldehydes/|Dichloroacetaldehyde is a metabolite of vinylidene chloride.|cis- and trans-1,2-Dichloroethylene are metabolized, in part, to dichloroacetaldehyde.
Crude product contained: 4% CCl3CHO, 1% ClCH2CHO /From table/
SYMPTOMS: Symptoms of exposure to this compound include local irritation of eyes, nose, and mucous membranes. ACUTE/CHRONIC HAZARDS: Toxic. May cause irritation on contact. Hazardous decomposition products. Combustible liquid. (NTP, 1992)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Volatile chemicals have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
TOXIC BY INGESTION & INHALATION ...
dichloroacetaldehyde
Dichloroacetaldehyde Use and Manufacturing
By chlorination of acetaldehyde or paraldehyde /a trimer of acetaldehyde/ in the presence of a chlorination catalyst with subsequent distillation.|Reaction of acetaldehyde with chlorine at 70-80 °C|The most important industrial production process is the chlorination of acetaldehyde or paraldehyde. Hypochlorination of 1,2-dichloroethylene yields pure dichloroacetaldehyde.
In 1977, the estimated US production of dichloroacetaldehyde was between 10 million and 50 million lb. /From table/
Solid hydrate (minimum 82% anhydrous product); aqueous solution (minimum 65% anhydrous product)
Acetaldehyde, 2,2-dichloro-: ACTIVE|High yields are obtained in the chlorination of acetaldehyde or paraldehyde in the presence of antimony trichloride (83% yield) or phosphorous acid (>90%yield)
... Gas chromatographic methods for analysis of dichloroacetaldehyde.
Environmental transformation -> Pesticide transformation products (metabolite, successor)
Dichloroacetaldehyd is a known environmental transformation product of Dichlorvos.
Computed Properties
Molecular Weight:112.94
XLogP3:1.1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:111.9482701
Monoisotopic Mass:111.9482701
Topological Polar Surface Area:17.1
Heavy Atom Count:5
Complexity:34.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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