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Trichloracetaldehyd
2,2,2-trichloroacetaldehyde · TRICHLOROACETALDEHYDE · Anhydrous chloral · metachloral · CCl3CHO · Trichloroethanal · 2,2,2-Trichloroethanal · Grasex
Identifikatoren & physikalische Daten
| CAS No. | 75-87-6 |
|---|---|
| Summenformel | C2HCl3O |
| Durchschnittliche Molmasse | 147,38 g/mol |
| Monoisotopische Masse | 145,90929769 g/mol |
| SMILES | O=CC(Cl)(Cl)Cl |
| InChIKey | HFFLGKNGCAIQMO-UHFFFAOYSA-N |
| PubChem CID | 6407 |
| ChEMBL | CHEMBL27551 |
| ChEBI | CHEBI:48814 |
| EC No. | 200-911-5 |
| DTXSID | DTXSID7024744 |
| Lokaler Name | Trichloracetaldehyd |
Chemische & physikalische Eigenschaften
| XLogP | 1,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 17,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 6 |
| Formalladung | 0 |
| Komplexität | 54,3 |
| Stoffklassen | Other Classes -> AldehydesFlammable agents - 2nd degree |
| Arzneimittel | DEA NFLIS-Drug Category -> Depressants and TranquilizersPharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Boiling point |
| Geruch | Pungent, irritating odor |
| Dichte | 1.51 at 68 °F (NTP, 1992) - Denser than waterwill sink1.510 at 20 °C/4 °C1.404 at 25 °C/4 °C1.512 @ 20°C1.51 g/mL at 20 °C(lit.) |
| Color/Form | Colorless, mobile, oily liquid |
| Löslichkeit | Reaction (NTP, 1992)Freely soluble in water forming chloral hydrateSoluble in ethanol, etherSoluble in chloroformIn water, 8.3X10+6 mg/L at 25 °CChloroform (Sparingly), DMSO (Sparingly), Ethyl Acetate (Slightly) |
| Flammpunkt | 167 °F (NTP, 1992)75 °C75°C |
| Siedepunkt | 208 °F at 760 mmHg (NTP, 1992)97.8 °C at 760 mm Hg97.8 °C @760 [mm Hg]94-98 °C |
| Schmelzpunkt | -71.5 °F (NTP, 1992)-57.5 °C-57.5°C |
| Dampfdichte | 5.1 (Air = 1) |
| Polymerization | POLYMERIZES UNDER INFLUENCE OF LIGHT & IN PRESENCE OF SULFURIC ACID FORMING WHITE SOLID TRIMER CALLED METACHLORAL. |
| Brechungsindex | n20/D 1.456 |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 10.04(at 25℃) |
| Farbe | Off-White |
| Spezifische Wärmekapazität | Cp(liquid): 1.02 J/(g·K), at 25℃ |
| Merck | 13,9699 |
| Henry-Konstante | 3.4×103 mol/(m3Pa) at 25℃, Burkholder et al. (2019) |
| Dielektrizitätskonstante | 6.7(Ambient) |
| Stabilität | Stable. Flammable. Incompatible with strong oxidizing agents. |
| CAS Datenbank | 75-87-6(CAS DataBase Reference) |
| NIST chemische Informationen | Acetaldehyde, trichloro-(75-87-6) |
| EPA chemische Informationen | Chloral (75-87-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302 (92.3%): Harmful if swallowed [Warning Acute toxicity, oral]P260, P261, P264, P264+P265, P270, P271, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 52 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H350: May cause cancer [Danger Carcinogenicity] |
|---|---|
| Regulatorische Informationen | Hazard Traits - CarcinogenicityAcetaldehyde, 2,2,2-trichloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetaldehyde, 2,2,2-trichloro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 05-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/17495Acetaldehyde, trichloro-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| Weitere Sicherheitsinformationen | IMAP assessments - Acetaldehyde, trichloro-: Environment tier I assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Special Hazards of Combustion Products: Contain toxic and irritating gases including phosgene.· Combustible material: may burn but does not ignite readily. |
| Gesundheitsgefahren | INHALATION: Sore throat, shortness of breath, drowsiness, irritation of respiratory tract, unconsciousness. EYES: Redness, pain and blurred vision. SKIN: Redness and pain. INGESTION: Dizziness, drowsiness, nausea, and unconsciousness. Acute hazard: Poison may be fatal if inhaled, swallowed, or absorbed through skin. (USCG, 1999)· TOXIC and/or CORROSIVEinhalation, ingestion or skin contact with material may cause severe injury or death. |
| Gefahrenübersicht | A skin, eye, and mucous membrane irritantToxic by inhalation, ingestion, and skin contact[CAMEO] A corrosive substance that can cause injury to the skin, eyes, and respiratory tractHypnotic and CNS depressantEffects in high-dose animal studies include acute pulmonary edemaCan be habit forming with effects similar to alcohol. [MSDSonline] |
| DOT-Nummer und Handbuch | 2075 153 |
| Reaktive Gruppe | Aldehydes |
| Special Reports | European Chemicals BureauIUCLID Dataset, Trichloroacetaldehyde (75-87-6), 42 pp. (2000 CD-ROM edition). Available from the Database Query page at: http://ecb.jrc.it/esis/esis.php as of July 18, 2008.TSCA CHIPs present a preliminary assessment of chloral's potential for injury to human health & the environment (available at EPA's TSCA Assistance Office: (202) 554-1404 or (800) 424-9065) |
| RCRA-Anforderungen | U034As stipulated in 40 CFR 261.33, when chloral, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5). |
| TSCA-Anforderungen | Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Chloral is included on this list. Effective date 9/30/91Sunset date 6/30/98. |
| Reactivity Alerts | Polymerizable |
| Brandbekämpfung | Fire Extinguishing Agents: Small fires: Dry chemical, carbon dioxide, water spray or foam. Large fires: Water spray, fog or foam. (USCG, 1999) |
| Freisetungsmaßnahmen | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| Erste Hilfe | 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.General First Aid: |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Brandbekämpfungsverfahren | This chemical is a combustible liquid. Poisonous gases are produced in fireincluding hydrogen chloride. Use dry chemical, carbon dioxide, or foam extinguishers. Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined area may explode in fire. Storage containers and parts of containers may rocket great distances, in many directions. If materials or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. If employees are expected to fight fires, they must be trained and equipped.If material on fire or involved in fire: Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. Apply water from as far a distance as possible. Keep run-off water out of sewers and water sources. /Chloral, anhydrous, stabilized/ |
| Lagerbedingungen | Prior to working with Chloroal you should be trained on its proper handling and storage. Protect from light, moisture, air and acids. DEA regulations require storage in a locked storage area. Store in tightly closed containers in a cool, well-ventialted area. Metal containers involving the transfer of 5 gallons or more of ethylene oxide should be grounded and bonded. Drums must be equipped with self-closing valves, pressure vacuum bungs, and flame arresters. Use only non-sparking tools and equipment, especially when opening and closing containers of this chemical. Sources of ignition such as smoking and open flames are prohibited where ethlyene oxides is handled, used, or stored in a manner that could create a potential fire or explosion hazard. |
| Reinigungsverfahren | Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Wntilate area of spill or leak. Absorb liquids in vermiculite, dry sand, earth, or a similar non-organic materials and deposit in sealed containers. May also be covered with weak reducing agentsresulting sludge neutralized and flushed to sewer. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area of spill or leak after clean-up is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean-up spills, they must be properly trained and equipped.Absorb the spills with rags or other available absorbing materials. |
| Freisetung ohne Brand | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Entsorgungsverfahren | [40 CFR 240-280, 300-306, 702-799 (7/1/2006)] Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U034, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.Incineration after mixing with another combustible fuelcare must be taken to assure complete combustion to prevent phosgene formationan acid scrubber is necessary to remove the halo acids produced.A potential candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.TO REMOVE CHLORAL FROM WASTE WATER, A STOICHIOMETRIC AMT OF SODIUM HYDROXIDE OR CALCIUM HYDROXIDE WAS ADDED, AND THE WASTE WATER WAS THEN AERATED 60 MIN AT 40 °C. |
| Preventive Measures | Wear protective gloves and clothing to prevent any reasonable probability of skin contact. Safety equipment suppliers/manufacturers can provide recommendations on the most protective glove/clothing material for your operation. All protective clothing (suits, gloves, footwear, headgear) should be clean, available each day, and put on before work. Contact lenses should not be worn when working with this chemical. Wear splash-proof chemical goggles and face shield unless full facepiece respiratory protection is worn. Employees should wash immediately with soap when skin is wet or contaminated. Provide emergency showers and eyewash.SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. /Chloral, anhydrous, stabilized/Personnel protection: Keep upwind. Avoid breathing vapors. ... Do not handle broken packages unless wearing appropriate personal protective equipment. /Chloral, anhydrous, stabilized/SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place. |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:Immediate precautionary measure |
| Protective Action Criteria (PAC) | 0.65 [mg/m3]7.2 [mg/m3]43 [mg/m3] |
| Wechselwirkungen | THE CONCURRENT INGESTION OF CHLORAL HYDRATE AND ALCOHOL CAUSES TWO CLINICALLY IMPORTANT INTERACTIONS. ONE IS AN ALLEGED ENHANCEMENT OF THE CNS DEPRESSANT EFFECTS OF CHLORAL HYDRATE & ALCOHOLTHE OTHER IS A PROFOUND VASODILATION. /CHLORAL HYDRATE/ |
| Ökotoxizitätswerte | LD50 Agelaius phoeniceus (Red-winged blackbird) oral (by gavage) 100 mg/kg bwEC50Species: Daphnia magna (Water flea, <24 hr neonate)Conditions: freshwater, static, 20 °CConcentration: 170000 ug/L for 1 hrEffect: decreased enzyme activityConcentration: 246000 ug/L for 24 hrEffect: intoxication, immobilizationConcentration: 112000 ug/L for 48 hr |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 0.68(SRC), determined from a water solubility of 8.3X10+6 mg/L(2) and a regression-derived equation(3), indicates that chloral is expected to have very high mobility in soil(SRC). Volatilization of chloral from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 2.9X10-9 atm-cu m/mole(4). Chloral is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 50 mm Hg(5). The compound reached 8% of its theoretical BOD in the Japanese MITI test(2), indicating that biodegradation is not an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 0.68(SRC), determined from a water solubility of 8.3X10+6 mg/L(2) and a regression-derived equation(3), indicates that chloral is not expected to adsorb to suspended solids and sediment(SRC). Chloral reacts exothermically with water to form chloral hydrate(4), with which it is in equilibrium. Since the equilibrium constant of chloral to chloral hydrate reaction is 3.6X10-5, very little chloral will remain in solution(5). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 2.91X10-9 atm-cu m/mole(6). According to a classification scheme(7), an estimated BCF of 5(SRC), from an estimated log Kow of 1.2(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The compound reached 8% of its theoretical BOD in four weeks using an activated sludge inoculum in the Japanese MITI test(2), indicating that biodegradation is not likely to be an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chloral, which has a vapor pressure of 50 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase chloral is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 13 days(SRC), calculated from its rate constant of 1.60X10-12 cu cm/molec-sec(3). Chloral exhibited a photodissociation rate of 4.61 to 6.11X10-5/sec, corresponding to photolysis lifetime of 4.5 to 6 hours under conditions of solar flux in summer months(4) and therefore is susceptible to direct photolysis by sunlight(SRC). |
| Unerwünschte Wirkungen | Neurotoxin - Other CNS neurotoxin |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=75-87-6] |
| Effluent Concentrations | Chloral was reported in the spent chlorination liquor from bleaching of sulfite pulp at high lignin content and pulp at normal lignin content after oxygen treatment (approximate concentrations of < 0.1-0.5 g/ton pulp)(1,2). |
| Medical Surveillance | Lung function tests. Serum trichloroethanol level. |
| Soil Adsorption/Mobility | The Koc of chloral is estimated as 0.68(SRC), using a water solubility of 8.3X10+6 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that chloral is expected to have very high mobility in soil. |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ It is corrosive to tissue./OTHER TOXICITY INFORMATION/ The causative interrelationship between long-term, low level exposure to chlorinated volatile organic solvents (VOSs) and neurodegenerative diseases (polyneuropathy, encephalopathy) are still an issue of controversial debate. Endogeneously formed chlorinated tetrahydro-beta-carbolines found by Bringmann 1995 (TaClo hypothesis) may contribute, in particular, to the development of (idiopathic) Parkinson's disease (PD) in the presence of the sufficient amount of trichloroacetaldehyde, an intermediate in metabolism of trichloroethylene (TRI). Long-term storage of specific VOSs over years, evident frrom exhalation pattern during the postexposure period, may serve as a promoting factor to form continuously TaClo non-enzymatically from tryptamine and trichloroacetaldehyde. Thus, the induction of TaClo-mediated neurotoxic processes extends over years. The onset of Parkinson's disease in three chronic TRI-exposed individuals during the postexposure period could be associated with the presence of TaClo in ng-range. Consequently, determination of TaClo and its derivatives in blood of humans exposed to chlorinated VOSs may serve as a marker of risk indicating either causative or supportive processes of neurodegeneration that may lead to manifestation of PD after many years. |
| Artificial Pollution Sources | Chloral's production and use in the manufacture of chloral hydrate and DDT(1) may result in its release to the environment through various waste streams(SRC). Trichloroacetaldehyde has been found at low concentrations in spent chlorination liquor from bleaching of various sulphite pulps. Effluents from wood processing plants, therefore, may be a source of trichloroacetaldehyde release to the environment(2). It has been suggested that trichloroacetaldehyde is formed during chlorination by the reaction of chlorine with residual organic compounds in the water(3) and trichloroacetaldehyde was identified as a reaction product of soil humus and aqueous chlorine(4). Chloral was formed as a result of chlorination of soil humic material using samples from the Ao horizon of a forest at Gifu City, Japan, forested predominantly with Chemaecyparis obtusa (Hinko) and Pinus densiflora (Pine wood)(4). The humic substances contained 34.0% carbon, 4.0% hydrogen, 4.1% nitrogen, and 11.6% ash with a C/N ratio of 8.3(4). |
| Environmental Biodegradation | AEROBIC: Chloral, present at 100 mg/L, reached 8% of its theoretical BOD in four weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(1). |
| Carcinogen Classification | ChloralGroup 2A: Probably carcinogenic to humansVolume 63: (1995) Dry Cleaning, Some Chlorinated Solvents and Other Industrial Chemicals20142012 |
| CERCLA-Meldepflichtmengen | Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5,000 lb or 2,270 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b). |
| F | 1-8-9-13 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2075 (CHLORAL, ANHYDROUS, STABILIZED) |
| Zollcode | 29130000 |
| RTECS-Nr. | FM7870000 |
| R-Sätze (R) | 23-36/37/38-22 |
| Gefahrensymbole | T,Xn |
| Sicherheitshinweise (S) | 26-36/37-45-7/9-28 |
| Gefahrenklasse | 6.1 |
| Verpackungsgruppe | II |
| Gefahrstoffdaten | 75-87-6(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
manufacture of chloral hydrate, DDT.