Benzylchlorid Chemische Eigenschaften,Einsatz,Produktion Methoden
ERSCHEINUNGSBILD
FARBLOSE FLüSSIGKEIT MIT STECHENDEM GERUCH.
CHEMISCHE GEFAHREN
Polymerisiert unter Einfluss aller üblicherweise verwendeten Metalle mit Ausnahme von Nickel und Blei, unter Entwicklung ?tzender Rauche (Chlorwasserstoff - s. ICSC 0163). Feuer- und Explosionsgefahr. Beim Verbrennen Bildung giftiger und ?tzender Rauche (Chlorwasserstoff). Reagiert sehr heftig mit starken Oxidationsmitteln. Greift viele Metalle in Gegenwart von Wasser an .
ARBEITSPLATZGRENZWERTE
TLV: 1 ppm; (als TWA); Krebskategorie A3 (best?tigte krebserzeugende Wirkung beim Tier mit unbekannter Bedeutung für den Menschen); (ACGIH 2005).
MAK: ; Hautresorption; Krebserzeugend Kategorie 2; (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den K?rper durch Inhalation, über die Haut und durch Verschlucken.
INHALATIONSGEFAHREN
Beim Verdampfen bei 20 °C kann schnell eine gesundheitssch?dliche Kontamination der Luft eintreten; beim Versprühen sehr viel schneller.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION: Die Substanz ver?tzt die Augen. Die D?mpfe reizen die Augen, die Haut und die Atmungsorgane. Inhalation von D?mpfen oder Aerosolen kann zu Lungen?dem führen (s. Anm.). M?glich sind Auswirkungen auf das Zentralnervensystem mit nachfolgender Bewusstlosigkeit.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
M?glich sind Auswirkungen auf Leber und Nieren. Führt zu Gewebesch?den. M?glicherweise krebserzeugend für den Menschen. Tierversuche zeigen, dass die Substanz m?glicherweise fruchtbarkeitssch?digend oder entwicklungssch?digend wirken kann.
LECKAGE
Ausgelaufene Flüssigkeit in abgedeckten nichtmetallischen Beh?ltern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen. NICHT in die Umwelt gelangen lassen. Chemikalienschutzanzug mit umgebungsluftunabh?ngigem Atemschutzger?t.
R-S?tze Betriebsanweisung:
R45:Kann Krebs erzeugen.
R22:Gesundheitssch?dlich beim Verschlucken.
R23:Giftig beim Einatmen.
R37/38:Reizt die Atmungsorgane und die Haut.
R41:Gefahr ernster Augensch?den.
R48/22:Gesundheitssch?dlich: Gefahr ernster Gesundheitssch?den bei l?ngerer Exposition durch Verschlucken.
S-S?tze Betriebsanweisung:
S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).
Aussehen Eigenschaften
C7H7Cl; Chlortoluol, 1-Chlormethylbenzol, Chlorphenylmethan, Tolylchlorid; farblose, an feuchter Luft schwach rauchende Flüssigkeit mit stechendem, zu Tränen reizendem, unangenehmem Geruch.
Gefahren für Mensch und Umwelt
Heftige Reaktionen sind mit Alkalimetallen, Erdalkkalimetallen, Metallen, starken Oxidationsmitteln, Amiden, katalytisch wirkenden Substanzen und zahlreichen anorganischen und/oder organischen Verbindungen möglich.
Benzylchlorid ist brennbar. Bei Erhitzung in dampf-/gasförmigem Zustand ist es mit Luft explosionsfähig.
Benzylchlorid wirkt sehr stark reizend auf Schleimhäute und Augenbindehäute. Nach Inhalation höherer Konzentrationen ist mit Lungenödem und narkotischen Zuständen zu rechnen. Schleimhautreizende Konzentrationen können auch Störungen der Leberfunktion hervorrufen. Von der Flüssigkeit benetzte feuchteHaut schmerzt sehr stark und bildet typische Ätzschorfe.
Ein Verschlucken ist infolge der sehr starken Geruchswarnung kaum denkbar. Sie würde zu schwersten VVerätzungen der Schleimhäute führen.
Im Tierversuch hat sich Benzylchlorid als mutagen und koncerigen erwiesen.
Stark wassergefährdend.
Schutzma?nahmen und Verhaltensregeln
Nur im Abzug arbeiten.
Handschuhe aus Gummi (nur als kurzzeitiger Spritzschutz).
Verhalten im Gefahrfall
Mit flüssigkeitsbindendem Material (z.B. Sand, Kieselgur, Universalbinder) aufnehmen.
In gut verschließbaren Behältern als Sondermüll entsorgen.
Schaum, Pulverlöscher.
Erste Hilfe
Nach Hautkontakt: Bei Berührung mit der Haut sofort mit viel Waser und Seife abwaschen.
Nach Augenkontakt: Sofort mit viel Wasser mindestens 15 Minuten bei geöffnetem Lidspalt spülen. Augenarzt konsultieren.
Nach Einatmen: Frischluft. Arzt konsultieren.
Nach Verschlucken: Viel Wasser trinken lassen.
Den Betroffenen nur bei vollem Bewußtsein selbsttätig erbrechen lassen. Sofort Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminierte Kleidung sofort ausziehen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Als Sondermüll entsorgen.
Chemische Eigenschaften
Benzyl chloride is a colorless to s lightly yellow liquid with a strong, unpleasant, irritating odor. The Odor Threshold is 0.05 ppm.The stabilized form of benzyl chloride contains a fixed amount of a sodium carbonate solution or propylene oxide.
Physikalische Eigenschaften
Colorless to pale yellowish-brown liquid with a pungent, aromatic, irritating odor. Odor threshold concentration is 47 ppbv (Leonardos et al., 1969). Katz and Talbert (1930) reported an experimental detection odor threshold concentration of 210 μg/m3 (41 ppbv). The solubility of benzyl chloride in water is 0.33 g/L at 4°C, 0.49 g/L at 20°C, and 0.55 g/L at 30°C. It is freely soluble in chloroform, acetone, acetic acid esters, diethyl ether, and ethyl alcohol.
Verwenden
Benzyl chloride is used in the manufacture of benzyl Compounds, dyes, artificial resins, tanning agents, phar maceuticals, plasticizers, synthetic tannins, perfumes, lubricants, and quaternary ammonium compounds. It is also an intermediate in the preparation of phenylacetic acid (precursor to phamaceuticals).
Vorbereitung Methode
Benzyl chloride can be synthesized by chloromethylation of benzene in the presence of a catalyst (ZnCl2) or by treatment of benzyl alcohol with SO2Cl2. Commercially it is produced by chlorination of boiling toluene in the presence of light.
Application
Benzyl chloride is used mainly to produce plasticizers (e.g., benzyl butyl phthalate), benzyl alcohol, and phenylacetic acid via benzyl cyanide (used in the production of synthetic penicillin). On a smaller scale, it is used to produce quaternary ammonium salts (for disinfectants and phase-transfer catalysts), benzyl esters (benzyl benzoate and benzyl acetate for the flavors and perfumes industry), dyes of the triphenylmethane series, dibenzyl disulfide (antioxidant for lubricants), benzylphenol, and benzylamines.
Definition
ChEBI: Benzyl chloride is a member of the class of benzyl chlorides that is toluene substituted on the alpha-carbon with chlorine.
synthetische
Benzyl chloride is the starting material for a large number of industrial syntheses. The first preparation of it involved not the chlorination of toluene, however, but the reaction of benzyl alcohol with hydrochloric acid (S. Cannizzaro, 1853). Today, most side-chain chlorination of toluene to produce benzyl chloride. Dibenzyl ether is formed as a byproduct in the alkaline hydrolysis of benzyl chloride to benzyl alcohol. This ether can be re-converted to benzyl chloride by cleavage with hydrogen chloride at a temperature below 100°C.
Reaktionen
Benzyl chloride can be oxidized to benzoic acid or benzaldehyde, or substituted to give the halogenated, sulfonated or nitrated product.With NH3 it yields mono-, di- or tribenzyl amine. With alcohols in base the benzylalkyl ether is formed. With phenols either the phenolic or nuclear hydrogens can react to give benzylaryl ether or benzylated phenols. Reaction with NaCN gives benzyl cyanide (phenylacetonitrile); with aliphatic primary amines the product is the N-alkylbenzylamine, and with aromatic primary amines N-benzylaniline is formed. Benzyl chloride is converted to butyl benzyl phthalate plasticizer and other chemicals.
Allgemeine Beschreibung
Benzyl chloride appears as a colorless liquid with an irritating odor. Toxic by inhalation and skin absorption. Flash point 153°F. Slightly soluble in water. Corrosive to metals and tissue. A lachrymator. Density 9.2 lb /gal.
Air & Water Reaktionen
A lachrymator. Slightly soluble in water.
Reaktivit?t anzeigen
Halogenated aliphatic compounds, such as Benzyl chloride, are moderately or very reactive. Reactivity generally decreases with increased degree of substitution of halogen for hydrogen atoms. Materials in this group are incompatible with strong oxidizing and reducing agents. Also, they are incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.
Hazard
Highly toxic, intense eye and skin irritant. A
lachrymator. Upper respiratory tract irritant. Prob-
able carcinogen.
Health Hazard
Benzyl chloride is a corrosive liquid. Con tact with the eyes can cause corneal injury.Exposure to its vapors can produce intenseirritation of the eyes, nose, and throat. Highconcentrations may cause lung edema anddepression of the central nervous system.Flury and Zernik (1931) stated that exposureto 16 ppm for 1 minute was intolerable tohumans. The LC50 values for a 2-hour expo sure in mice and rats are 80 and 150 ppm,respectively. The subcutaneous LD50 valuein rats is 1000 mg/kg (NIOSH 1986).
Benzyl chloride tested positive to thehistidine reversion–Ames test for mutagenic ity. Subcutaneous administration of this com pound in laboratory animals caused tumors atthe site of application.
Auswirkungen auf die Gesundheit
A concentration of 16
ppm of benzyl chloride in air is reported to be
intolerable to humans within 1 min. The compound is a potent lachrymator, strongly irritating
to the eyes, nose, and throat and capable of
causing lung edema.
Brandgefahr
Benzyl chloride burns but does not ignite readily. Benzyl chloride may ignite combustibles. When heated to decomposition, Benzyl chloride emits toxic and corrosive fumes. Some organic chlorides decompose to yield phosgene. Incompatible with active metals such as copper, aluminum, magnesium, iron, zinc, and tin and keep from strong oxidizing agents. Avoid contact with acids or acid fumes. Keep separate from oxidizing materials. May become unstable at elevated temperatures and pressures; may react with water resulting in some nonviolent release of energy. Polymerizes with evolution of heat and hydrogen chloride when in contact with all common metals except nickel and lead.
Toxikologie
The acute oral toxicity (LD50) of benzyl chloride
in rats is 1231 mg/kg and in mice 1624 mg/kg. The subcutaneous LD50 (in rats) of benzyl
chloride in oil solution is 1000 mg/kg.
Exposure of rats and mice to benzyl chloride
concentrations of 100 –1000 mg/m3 for 2 h
caused irritation of the mucous membranes and
conjunctivitis, vol. 11. Benzyl chloride is a
strong skin-sensitizing agent for guinea pigs . Benzyl chloride acts weakly mutagenic
in validated test systems.
Subcutaneous injection of weekly doses of 80
mg/kg for 1 year followed by a post-observation
period resulted in local sarcomas with lung
metastases in rats. The mean induction time was
500 d. After dermal application of benzyl
chloride, skin carcinomas were observed in mice.
m?gliche Exposition
Used as an intermediate and as an irritant gas in chemical warfare. In contrast to phenyl halides, benzyl halides are very reactive. Benzyl chloride is used in production of benzal chloride, benzyl alcohol, and benzaldehyde. Industrial usage includes the manufacture of benzyl compounds, cosmetics, dyes, plastics, synthetic tannins, perfumes and resins. It is used in the manufacture of many pharmaceuticals. Suggested uses of benzyl chloride include: the vulcanization of fluororubbers and the benzylation of phenol and its derivatives for the production of possible disinfectants.
Carcinogenicity
Benzyl chloride caused genetic mutations
and chromosome-damaging effects in a wide
variety of in vitro assays; it was not mutagenic
in vivo in the mouse micronucleus assay
Environmental Fate
Biological. When incubated with raw sewage and raw sewage acclimated with hydrocarbons,
benzyl chloride degraded forming nonchlorinated products (Jacobson and Alexander, 1981).
Chemical/Physical. Anticipated products from the reaction of benzyl chloride with ozone or OH
radicals in the atmosphere are chloromethyl phenols, benzaldehyde and chlorine radicals (Cupitt,
1980).
Slowly hydrolyzes in water forming HCl and benzyl alcohol. The estimated hydrolysis half-life
in water at 25 °C and pH 7 is 15 h (Mabey and Mill, 1978). The hydrolysis rate constant for
benzyl chloride at pH 7 and 59.2 °C was determined to be 0.0204/min, resulting in a half-life of 34
min (Ellington et al., 1986).
May polymerize in contact with metals except nickel and lead (NIOSH, 1997).
When heated to decomposition, hydrogen chloride gas may be released (CHRIS, 1984).
Versand/Shipping
UN1738 Benzyl chloride, Hazard class: 6.1;
Labels: 6.1—Poisonous materials, 8—Corrosive material.
l?uterung methode
Dry it with MgSO4 or CaSO4, or reflux it with fresh Ca turnings, then fractionally distil it under reduced pressure, collecting the middle fraction and storing it over CaH2 or P2O5. It has also been purified by passage through a column of alumina. Alternatively it is dried over MgSO4 and distilled in a vacuum. The middle fraction is degassed by several freeze-thaw cycles and then fractionated in an 'isolated fractionating column' (which has been evacuated and sealed off at ~10-6 mm) over a steam bath. The middle fraction is retained. The final samples are distilled in a vacuum from this sample and again retaining the middle fraction. The purity is >99.9% (no other peaks are visible by GLC, and the NMR spectrum is consistent with the structure. [Mohammed & Kosower J Am Chem Soc 93 1709 1971, Beilstein 5 IV 809.] IRRITANT and strongly LACHRYMATORY.
Inkompatibilit?ten
May form explosive mixture with air.
Contact with water forms hydrogen chloride fumes. Strong
oxidizers may cause fire and explosions. Unstabilized benzyl
chloride undergoes polymerization with copper, aluminum,
iron, zinc, magnesium, tin, and other common metals
except lead and nickel, with the liberation of heat and
hydrogen chloride gas. May accumulate static electrical
charges, and may cause ignition of its vapors. Attacks some
plastics and rubber. Thermal decomposition and polymerization
reactions are inhibited, to a limited extent, by addition
of triethylamine, propylene oxide, or sodium carbonate.
Waste disposal
Incineration @ 816 C for
0.5 second minimum for primary combustion and 1204 C
for 12.0 second for secondary combustion. Elemental chlorine
formation may be alleviated by injection of steam or
methane into the combustion process.
Benzylchlorid Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte