Bis(chlormethyl)ether
Bezeichnung:Bis(chlormethyl)ether
CAS-Nr542-88-1
Englisch Name:BIS(CHLOROMETHYL)ETHER
CBNumberCB8120955
SummenformelC2H4Cl2O
Molgewicht114.96
MOL-Datei542-88-1.mol
Synonyma
Oxybis[chlormethan]
Bis(chlormethyl)ether
BCME
sym-Dichlormethylether
1,1'-Dichlordimethylether
Oxybis(chlormethan)
Chlor(chlormethoxy)methan
Bis(chlormethyl)ether physikalisch-chemischer Eigenschaften
Schmelzpunkt | 171℃ |
Siedepunkt | 106℃ |
Dichte | 1.267 |
Dampfdruck | 30 at 22 °C (Dreisbach, 1952) |
Brechungsindex | 1.44433 |
Flammpunkt | 75℃ |
storage temp. | -20°C Freezer |
Löslichkeit | Soluble in alcohol, ether (Weast, 1986), benzene (Hawley, 1981), and other solvents including acetone and chloroform. |
Aggregatzustand | Colorless liquid |
Farbe | Colorless liquid with a suffocating odor |
Expositionsgrenzwerte | TLV-TWA 0.0047 mg (0.001 ppm)/m3 (Hu man Carcinogen) (ACGIH); Human and Animal Carcinogen-Sufficient Evidence (IARC); Carcinogen (OSHA). |
IARC | 1 (Vol. 4, Sup 7, 100F) 2012 |
EPA chemische Informationen | Bis(chloromethyl) ether (542-88-1) |
Kennzeichnung gefährlicher | T+ |
R-Sätze: | 10-36/37/38-40-26-24-22-45 |
S-Sätze: | 26-36/37/39-45-53 |
RIDADR | 2249 |
HazardClass | 6.1(a) |
PackingGroup | I |
Giftige Stoffe Daten | 542-88-1(Hazardous Substances Data) |
Toxizität | Acute oral LD50 for rats is 210 mg/kg (quoted, RTECS, 1985). |
Gefahreninformationscode (GHS)
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Bildanzeige (GHS)
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Alarmwort
Achtung
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Gefahrenhinweise
H225:Flüssigkeit und Dampf leicht entzündbar.
H302:Gesundheitsschädlich bei Verschlucken.
H311:Giftig bei Hautkontakt.
H330:Lebensgefahr bei Einatmen.
H350:Kann Krebs verursachen.
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Sicherheit
P210:Von Hitze, heißen Oberflächen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.
P233:Behälter dicht verschlossen halten.
P240:Behälter und zu befüllende Anlage erden.
P241:Explosionsgeschützte [elektrische/Lüftungs-/ Beleuchtungs-/...] Geräte verwenden.
P242:Nur funkenfreies Werkzeug verwenden.
P243:Maßnahmen gegen elektrostatische Entladungen treffen.
P260:Dampf/Aerosol/Nebel nicht einatmen.
P264:Nach Gebrauch gründlich waschen.
P264:Nach Gebrauch gründlich waschen.
P270:Bei Gebrauch nicht essen, trinken oder rauchen.
P271:Nur im Freien oder in gut belüfteten Räumen verwenden.
P280:Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P284:Atemschutz tragen.
P301+P312:BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P302+P352:BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.
P303+P361+P353:BEI BERÜHRUNG MIT DER HAUT (oder dem Haar): Alle kontaminierten Kleidungsstücke sofort ausziehen. Haut mit Wasser abwaschen oder duschen.
P304+P340:BEI EINATMEN: Die Person an die frische Luft bringen und für ungehinderte Atmung sorgen.
P310:Sofort GIFTINFORMATIONSZENTRUM/Arzt/ anrufen.
P312:Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P320:Besondere Behandlung dringend erforderlich
P322:Gezielte Maßnahmen
P330:Mund ausspülen.
P361:Alle kontaminierten Kleidungsstücke sofort ausziehen.
P363:Kontaminierte Kleidung vor erneutem Tragen waschen.
P370+P378:Bei Brand: zum Löschen verwenden.
P403+P233:An einem gut belüfteten Ort aufbewahren. Behälter dicht verschlossen halten.
P403+P235:An einem gut belüfteten Ort aufbewahren. Kühl halten.
P405:Unter Verschluss aufbewahren.
P501:Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.
BIS(CHLOROMETHYL)ETHER Chemische Eigenschaften,Einsatz,Produktion Methoden
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ERSCHEINUNGSBILD
FARBLOSE FLüSSIGKEIT MIT STECHENDEM GERUCH. -
PHYSIKALISCHE GEFAHREN
Die Dämpfe mischen sich leicht mit Luft. Bildung explosionsfähiger Gemische. -
CHEMISCHE GEFAHREN
Zersetzung beim Erhitzen und bei Kontakt mit Wasser unter Bildung giftiger und ätzender Rauche mit Chlorwasserstoff (s. ICSC 0163), Formaldehyd. Greift viele Metalle, Kunststoffe und Harze an. -
ARBEITSPLATZGRENZWERTE
TLV: 0.001 ppm (als TWA); Krebskategorie A1(bestätigte krebserzeugende Wirkung beim Menschen); (ACGIH 2005).
MAK: Krebserzeugend Kategorie 1; (DFG 2005).
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AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation der Dämpfe, über die Haut und durch Verschlucken. -
INHALATIONSGEFAHREN
Beim Verdampfen bei 20°C kann sehr schnell eine gesundheitsschädliche Kontamination der Luft eintreten. -
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Die Substanz verätzt die Augen, die Haut und die Atemwege. ätzend beim Verschlucken. Inhalation hoher Konzentrationen kann zu Lungenödem führen (s.Anm.). Die Auswirkungen treten u.U. verzögert ein. Exposition kann zum Tod führen. -
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Krebserzeugend für den Menschen. -
LECKAGE
Gefahrenbereich verlassen! Fachmann zu Rate ziehen! Persönliche Schutzausrüstung: Vollschutzanzug mit umgebungsluftunabhängigem Atemschutzgerät. Ausgelaufene Flüssigkeit in abdichtbaren Behältern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen. -
R-Sätze Betriebsanweisung:
R10:Entzündlich.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R40:Verdacht auf krebserzeugende Wirkung.
R26:Sehr giftig beim Einatmen.
R24:Giftig bei Berührung mit der Haut.
R22:Gesundheitsschädlich beim Verschlucken.
R45:Kann Krebs erzeugen. -
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen. -
Aussehen Eigenschaften
C2H4Cl2O.
Farblose, lokal reizende Flüssigkeit mit chloroformartigem Geruch. -
Gefahren für Mensch und Umwelt
Wird mit Wasser langsam unter geringer Wärmeentwicklung zersetzt.
Sehr giftig bereits beim Einatmen geringer Mengen von Dämpfen. Schwache akute Reizwirkung auf Haut, Augen und Atemwege. In höheren Konzentrationen narkotisierende Wirkung. Verursacht Lungenschädigungen und bösartige Tumore. Allergien sind bekannt. Sehr stark krebsgefährdend. Ernste Gefahr irreversibler Schäden. -
Schutzmaßnahmen und Verhaltensregeln
Behälter und dunkle Glasflaschen dicht geschlossen halten und an gut belüfteten Ort aufbewahren. Berührung mit den Augen und der Haut vermeiden.
Alle Arbeiten im Abzug durchführen.
Neopren-Schutzhandschuhe (nur als kurzzeitiger Spritzschutz). -
Verhalten im Gefahrfall
Ausgelaufene oder verschüttete Lösung mit wässriger Ammoniaklösung versetzen.
CO2-, Pulverlöscher oder Wasser einsetzen. -
Erste Hilfe
Nach Hautkontakt: Abtupfen. Mit Wasser und Seife waschen. Schutz vor Infektion. Hautarzt!
Nach Augenkontakt: Mit viel Wasser mindestens 15 Minuten bei geöffnetem Lidspalt spülen. Augenarzt!
Nach Einatmen: Frischluft. Arzt!
Nach Verschlucken: Aktivkohle (2 Eßlöffel auf 1/2 ltr. Wasser) trinken. Arzt!
Nach Kleidungskontakt: Kontaminierte Kleidung entfernen und in verd. Ammoniaklösung legen.
Ersthelfer: siehe gesonderten Anschlag -
Sachgerechte Entsorgung
Als Sondermüll entsorgen. -
Beschreibung
Bis(chloromethyl) ether is a colorless, volatileliquid with a suffocating odor. Molecular weight=115.0.Specific gravity (H2O:1)=1.32 at 25℃; Boilingpoint=106.1℃; Freezing/Melting point=-42℃; Vaporpressure=30 mmHg at 25℃; Flash point=# 18.8℃.Hazard Identification (based on NFPA-704 M RatingSystem): Health 4, Flammability 3, Reactivity 1 .Insoluble in water (decomposes, creating hydrogenchloride). -
Chemische Eigenschaften
colorless liquid -
Chemische Eigenschaften
Bis(chloromethyl) ether is a clear liquid with a strong unpleasant odor. It does not occur naturally. It dissolves easily in water, but degrades rapidly and readily evaporates into air. During earlier years, bis(chloromethyl) was used to make several types of polymers, resins, and textiles, but its use is now highly restricted. Only small quantities of bis(chloromethyl) ether are produced in the United States. The small quantities produced are only used in enclosed systems to make other chemicals. However, small quantities of bis(chloromethyl) ether may be formed as an impurity during the production of chloromethyl methyl ether. Along with other chemicals, rain, and sunlight, it undergoes chemical reactions and breaks down as formaldehyde and hydrochloric acid -
Chemische Eigenschaften
Bis(chloromethyl)ether is a colorless, volatile liquid with a suffocating odor. -
Verwenden
Reagent used in the formation of ether linked dimers -
Verwenden
Bis(chloromethyl)ether (BCME) is used asan intermediate in anion-exchange quater nary resins. Its use as a chloromethylationreagent in industry is being discontinuedbecause of its high carcinogenic properties.Exposure risks associated with this com pound can arise during the use or productionof chloromethyl methyl ether when the lat ter compound comes in contact with tracesof water in the presence of hydrogen orhydroxyl ions. It may occur in trace amountsin chloromethyl methyl ether. -
Verwenden
Bis(chloromethyl) ether is a clear liquid with a strong unpleasant odour. It does not occur naturally. It dissolves easily in water but degrades rapidly and readily evaporates into air. During earlier years, bis(chloromethyl) was used to make several types of polymers, resins, and textiles, but its use is now highly restricted. Only small quantities of bis(chloromethyl) ether are produced in the United States. The small quantities that are produced are only used in enclosed systems to make other chemicals. -
Definition
ChEBI: Bis(chloromethyl) ether is an ether that is dimethyl ether in which one of the hydrogens attached to each of the methyl group has replaced by a chlorine. It has a role as a carcinogenic agent and an alkylating agent. It is an ether and an organochlorine compound. -
Allgemeine Beschreibung
A colorless volatile liquid with a chloroform-like odor. Toxic by inhalation, skin absorption and ingestion. Dangerous fire risk - flash point below 0°F. Vapors much denser than air. Insoluble in water and denser than water. Used to make paints and varnish, and as a solvent. -
Air & Water Reaktionen
Highly flammable. Insoluble in water. Reacts with water to form hydrochloric acid & formaldehyde. -
Reaktivität anzeigen
DICHLORODIMETHYL ETHER is incompatible with the following: Acids, water [Note: Reacts with water to form hydrochloric acid & formaldehyde.] . -
Hazard
A carcinogen. Toxic by ingestion. -
Health Hazard
Acute toxicity is high by ingestion, inhalation, and skin irritation. Small quantities may cause death or permanent injury after very short exposure. Chloromethyl ether is an alkylating agent which is a recognized human carcinogen. There is a strong association between industrial exposure and excess lung cancer. -
Health Hazard
BCME is a highly toxic and carcinogeniccompound. The inhalation toxicity and car cinogenicity of this compound are greatestamong the haloethers
Exposure to its vapors can cause irritationof the eyes, nose, and throat in humans. Theprimary target organ is the lungs. Inhalationof 100 ppm of this compound in air for afew minutes can cause death to humans.Irritation of the eyes can be moderate tosevere and conjunctival. The acute oral anddermal toxicity of this compound, however,is moderate and comparable to that of bis(2-chloroethyl)ether
LC50 value, inhalation (rats): 33 mg (7ppm)/m3/7 hr
LD50 value, oral (rats): 210 mg/kg (NIOSH1986)
Tests on animals have confirmed the car cinogenic action of BCME. It is carcinogenicby inhalation and by subcutaneous and skinapplications. In humans it can produce lungcancer — a fact that is now well established.Tests on rats indicate that exposure to 0.1-ppm concentrations in air for 6 hours per dayfor 6 months produced tumors in the noseand lungs. Subcutaneous and skin applicationsproduced tumors at the site of application. -
Health Hazard
Exposures to bis(chloromethyl) ether cause irritation to the skin, eyes, throat, and lungs, and in cases of severe exposures cause damage to the lungs (swelling and bleeding) and death. Breathing low concentrations will cause coughing and nose and throat irritation. -
Brandgefahr
Container may explode in heat of fire. When heated to decomposition, BIS(CHLOROMETHYL)ETHER emits very toxic fumes of chlorides. Decomposed by water to hydrochloric acid and formaldehyde. Avoid water: hydrolyzes very rapidly (half life 10-40 seconds) on contact with water. Avoid decomposing heat, powerful oxidizers, areas of high fire hazard and moist air. -
mögliche Exposition
Exposure to bis(chloromethyl)ether may occur in industry and in the laboratory. This substance can form spontaneously in warm moist air by the combination of formaldehyde and hydrogen chloride. This compound is used as an alkylating agent in the manufacture of polymers; as a solvent for polymerization reactions; in the preparation of ion exchange resins; and as an intermediate for organic synthesis. Haloethers, primarily α-chloromethyl ethers, represent a category of alkylating agents of increasing concern due to the establishment of a causal relationship between occupational exposure to two agents of this class and lung cancer in the United States and abroad. The cancers are mainly oat cell carcinomas. Potential sources of human exposure to BCME appear to exist primarily in areas including: (1) its use in chloromethylating (crosslinking) reaction mixtures in anion-exchange resin production; (2) segments of the textile industry using formaldehydecontaining reactants and resins in the finishing of fabric and as adhesive in the laminating and flocking of fabrics; and (3) the nonwoven industry which uses as binders, thermosetting acrylic emulsion polymers comprising methylol acrylamide, since a finite amount of formaldehyde is liberated on the drying and curing of these bonding agents. NIOSH has confirmed the spontaneous formation of BCME from the reaction of formaldehyde and hydrochloric acid in some textile plants and is now investigating the extent of possible worker exposure to the carcinogen. However, this finding has been disputed by industrial tests in which BCME was not formed in air by the reaction of textile systems employing hydrochloric acid and formaldehyde. -
Erste Hilfe
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 contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.Medical observation is recommended for 24 48 h afterbreathing overexposure, as pulmonary edema may bedelayed. As first aid for pulmonary edema, a doctor orauthorized paramedic may consider administering a corticosteroid spray. -
Carcinogenicity
Bis(chloromethyl) ether (BCME) is known to be human carcinogens based on sufficient evidence of carcinogenicity from studies in humans. -
Source
sym-Dichloromethyl ether may form as an intermediate by-product when form-aldehyde reacts with chloride ions under acidic conditions (Frankel et al., 1974; Tou and Kallos, 1974a; Travenius, 1982). Tou and Kallos (1974) reported that the reactants (formaldehyde and chloride ions) must be in concentrations of mg/L to form sym-dichloromethyl ether at concentrations of μg/L.
Chloromethyl methyl ether may contain 1 to 8% sym-dichloromethyl ether as an impurity (Environment Canada, 1993a). -
Environmental Fate
Chemical/Physical. Reacts rapidly with water forming HCl and formaldehyde (Fishbein, 1979; Tou et al., 1974). Tou et al. (1974) reported a hydrolysis half-life of 38 sec for sym-dichloromethyl ether at 20 °C.
Anticipated products from the reaction of sym-dichloromethyl ether with ozone or OH radicals in the atmosphere, excluding the decomposition products formaldehyde and HCl, are chloromethyl formate and formyl chloride (Cupitt, 1980). -
Lager
(1) Color Code—Red: Flammability Hazard:Store in a flammable liquid storage area or approved cabinet away from ignition sources and corrosive and reactivematerials. (2) Color Code—Blue: Health Hazard/Poison:Store in a secure poison location. Color Code—White:Corrosive or Contact Hazard; Store separately in a corrosion-resistant location. Color Code—Green: General storage may be used. Prior to working with this chemical youshould be trained on its proper handling and storage.Before entering confined space where this chemical maybe present, check to make sure that an explosive concentration does not exist. Store in airtight containers in a cool,dry, well-ventilated area. Metal containers involving thetransfer of this chemical should be grounded and bonded.Where possible, automatically pump liquid from drums orother storage containers to process containers. Drums mustbe equipped with self-closing valves, pressure vacuumbungs, and flame arresters. Use only nonsparking tools andequipment, especially when opening and closing containersof this chemical. Sources of ignition, such as smoking andopen flames, are prohibited where this chemical is used,handled, or stored in a manner that could create a potentialfire or explosion hazard. A regulated, marked area shouldbe established where this chemical is handled, used, orstored in compliance with OSHA Standard 1910.1045. -
Versand/Shipping
UN2249 Dichlorodimethyl ether, symmetrical, Hazard class: 6.1; Labels: 6.1—Poisonous materials, 3— Flammable liquid. -
Toxicity evaluation
No information is available on the transport and partitioning of BCME in the environment. Due to the relatively short half-life in both air and water, it is unlikely that significant partitioning between media or transport occurs. Primary process for BCME degradation in air is believed to be reaction with photochemically generated hydroxyl radicals to yield chloromethyl formate ClCHO, formaldehyde, and HCl. Atmospheric half-life due to reaction with hydroxyl radicals is estimated to be 1.36 h. Hydrolysis in the vapor phase is found to be slower with an estimated half-life of 25 h.
BCME is rapidly hydrolyzed in water to yield formaldehyde and HCl, and the hydrolysis rate constant is estimated to be 0.018 s-1at 20°C, which is equal to a half-life of ~35 s.
No information is available on the fate of BCME in soil. It is probable that BCME would rapidly degrade upon contact with moisture in soil. Due to its high volatile nature, it is not expected that BCME would persist in soil for significant periods. -
Inkompatibilitäten
May form explosive mixture with air. 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. Decomposes on contact with water, moist air, and heat, forming corrosive hydrochloric acid, hydrogen chloride, and formaldehyde vapors. May form shocksensitive compounds on contact with oxidizers, peroxides, and sunlight. Attacks many plastics. -
Waste disposal
Incineration, preferably after mixing with another combustible fuel. Care must be exercised to assure complete combustion to prevent the formation of phosgene. An acid scrubber is necessary to remove the halo acids produced.
BIS(CHLOROMETHYL)ETHER Upstream-Materialien And Downstream Produkte
Upstream-Materialien
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Downstream Produkte
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