o-Xylol

Bezeichnung:o-Xylol

CAS-Nr95-47-6

Englisch Name:o-Xylene

CBNumberCB1854693

SummenformelC8H10

Molgewicht106.17

MOL-Datei95-47-6.mol

Synonyma

o-Xylol

1,2-Dimethylbenzol

o-Xylen

o-Xylol physikalisch-chemischer Eigenschaften

Schmelzpunkt	-26--23 °C (lit.)
Siedepunkt	143-145 °C (lit.)
Dichte	0.879 g/mL at 20 °C (lit.)
Dampfdichte	3.7 (vs air)
Dampfdruck	<0.1 atm ( 21.1 °C)
Brechungsindex	n20/D 1.505(lit.)
Flammpunkt	90 °F
storage temp.	Store below +30°C.
Löslichkeit	water: partially soluble0.1705 g/L at 25°C
Aggregatzustand	Solid or Crystalline Powder
pka	>15 (Christensen et al., 1975)
Farbe	Yellow to beige
Geruch (Odor)	Benzene-like; characteristic aromatic.
Explosionsgrenze	1.0-7.6%(V)
Odor Threshold	0.38ppm
Wasserlöslichkeit	Sparingly soluble in water. (0.2g/L)
maximale Wellenlänge (λmax)	λ: 288 nm Amax: 1.00 λ: 300 nm Amax: 0.40 λ: 325 nm Amax: 0.05 λ: 350-400 nm Amax: 0.01
Merck	14,10081
BRN	1815558
Henry's Law Constant	14.0 at 45.00 °C, 16.4 at 50.00 °C, 19.0 at 55.00 °C, 21.3 at 60.00 °C, 26.3 at 70.00 °C (static headspace-GC, Park et al., 2004)
Expositionsgrenzwerte	NIOSH REL: 100 ppm (435 mg/m³), STEL 150 ppm (655 mg/m³), IDLH 900 ppm; OSHA PEL: TWA 100 ppm; ACGIH TLV: TWA 100 ppm, STEL 150 ppm (adopted).
Dielectric constant	2.5699999999999998
Stabilität	Stable. Incompatible with oxidizing agents. Flammable. Hygroscopic.
InChIKey	CTQNGGLPUBDAKN-UHFFFAOYSA-N
LogP	3.16 at 20℃
CAS Datenbank	95-47-6(CAS DataBase Reference)
NIST chemische Informationen	Benzene, 1,2-dimethyl-(95-47-6)
EPA chemische Informationen	o-Xylene (95-47-6)

Sicherheit

Kennzeichnung gefährlicher	Xn,T,F
R-Sätze:	10-20/21-38-39/23/24/25-23/24/25-11
S-Sätze:	25-45-36/37-16-7
RIDADR	UN 1307 3/PG 3
WGK Germany	2
RTECS-Nr.	ZE2450000
Selbstentzündungstemperatur	867 °F
TSCA	Yes
HazardClass	3
PackingGroup	II
HS Code	29024100
Giftige Stoffe Daten	95-47-6(Hazardous Substances Data)
Toxizität	Acute oral LD50 in rats is approximately 5 g/kg (quoted, RTECS, 1992).
IDLA	900 ppm

Gefahreninformationscode (GHS)

o-Xylene Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
FARBLOSE FLüSSIGKEIT MIT CHARAKTERISTISCHEM GERUCH.
PHYSIKALISCHE GEFAHREN
Fließen, Schütten o.ä. kann zu elektrostatischer Aufladung führen.
CHEMISCHE GEFAHREN
Reagiert mit starken Säurenund starken Oxidationsmitteln.
ARBEITSPLATZGRENZWERTE
TLV: 100 ppm (als TWA); 150 ppm (als STEL); Krebskategorie A4 (nicht klassifizierbar als krebserzeugend für den Menschen); BEI vorhanden; (ACGIH 2005).
MAK: (alle Isomeren) 100 ppm, 440 mg/m? Spitzenbegrenzung: überschreitungsfaktor II(2); Hautresorption; Schwangerschaft: Gruppe D; (DFG 2008).
EG Arbeitsplatz-Richtgrenzwerte: 50 ppm (als TWA); 100 ppm (als STEL); Hautresorption; (EU 2004).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation, über die Haut und durch Verschlucken.
INHALATIONSGEFAHREN
Beim Verdampfen bei 20 °C tritt langsam eine gesundheitsschädliche Kontamination der Luft ein.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Die Flüssigkeit reizt die Augen und die Haut. Möglich sind Auswirkungen auf das Zentralnervensystem. Verschlucken kann zur Aufnahme in der Lunge führen; Gefahr der Aspirationspneumonie.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Die Flüssigkeit entfettet die Haut. Möglich sind Auswirkungen auf das Zentralnervensystem.Exposition gegenüber der Substanz kann durch Lärmeinwirkung verursachte Hörschäden verstärken. Tierversuche zeigen, dass die Substanz möglicherweise fruchtbarkeitsschädigend oder entwicklungsschädigend wirken kann.
LECKAGE
Belüftung. Zündquellen entfernen. Ausgelaufene Flüssigkeit möglichst in abdichtbaren Behältern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen. NICHT in die Umwelt gelangen lassen. Persönliche Schutzausrüstung: Atemschutzfilter für organische Gase und Dämpfe.
R-Sätze Betriebsanweisung:
R10:Entzündlich.
R20/21:Gesundheitsschädlich beim Einatmen und bei Berührung mit der Haut.
R38:Reizt die Haut.
R39/23/24/25:Giftig: ernste Gefahr irreversiblen Schadens durch Einatmen, Berührung mit der Haut und durch Verschlucken.
R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
R11:Leichtentzündlich.
S-Sätze Betriebsanweisung:
S25:Berührung mit den Augen vermeiden.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S16:Von Zündquellen fernhalten - Nicht rauchen.
S7:Behälter dicht geschlossen halten.
Aussehen Eigenschaften
C8H10; (1,2-Dimethylbenzol). Farblose , stark lichtbrechende Flüssigkeit mit charakteristischem Geruch.
Gefahren für Mensch und Umwelt
o-Xylol ist leicht entzündlich und kann mit starken Oxidationsmitteln oder Leichtmetallen heftige bis explosionsartige Reaktionen eingehen.
Die Dämpfe von o-Xylol reizen die Augen, Schleimhäute, Atemwege und können Lungenödeme hervorufen. Der Hautkontakt kann Blasenbildung und Dermatitis verursachen. Gefahr der Hautresorption. Längere Exposition füht zu Schädigungen des ZNS, was mit Kopfschmerzen, Schwindel, Erregung, Krämpfen und unterUmständen mit Narkose einhergeht. Eine fruchtschädigende Wirkung kann nicht ausgeschlossen werden.
Wassergefährdender Stoff (WGK 1).
Schutzmaßnahmen und Verhaltensregeln
Schutzhandschuhe aus Gummi nur als kurzzeitiger Spritzschutz.
Im Abzug arbeiten und Exposition vermeiden.
Verhalten im Gefahrfall
Mit flüssigkeitsbindendem Material (z.B. Rench Rapid oder Chemizorb) aufnehmen und als Sondrmüll entsorgen. Kleinstmengen verdampfen lassen.
Kohlendioxid, Schaum, Pulver.
Erste Hilfe
Nach Hautkontakt: Mit reichlich Wasser und Seife abwaschen.
Nach Augenkontakt: Bei geöffnetem Lidspalt mit reichlich Wasser mind. 10 Minuten spülen.
Nach Einatmen: Frischluft.
Nach Verschlucken: Erbrechen vermeiden! Nachgabe von Aktivkohle (20-40g in 10%iger Aufschlämmnung). Arzt konsultieren.
Nach Kleidungskontakt: Kontaminierte Kleider sofort ausziehen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Als Sondermüll entsorgen.
Chemische Eigenschaften
colourless liquid
Physikalische Eigenschaften
Clear, colorless liquid with an aromatic odor. An odor threshold concentration of 380 ppb_v was reported by Nagata and Takeuchi (1990).
Verwenden
o-Xylene is largely used in the production of phthalic anhydride, and is generally extracted by distillation from a mixed Xylene stream in a plant primarily designed for p-Xylene production.
Verwenden
Preparation of phthalic acid, phthalic anhydride, terephthalic acid, isophthalic acid; solvent for alkyd resins, lacquers, enamels, rubber cements; manufacture of dyes, pharmaceuticals, and insecticides; motor fuels.
Verwenden
Xylene, xylenes, and total xylenes are used interchangeably since xylene usually exists as a mixture of three isomers: 1,2-dimethylbenzene, 1,3-dimethylbenzene, and 1,4-dimethylbenzene, i.e., o-, m-, and p-xylene, and is usually used as a mixture of the three forms. The mixture often also contains ethylbenzene. It is a high volume industrial chemical used in the synthetic fiber, chemical and plastics industries and as a solvent, cleaning agent and thinner for paints and varnishes.
Definition
ChEBI: A xylene substituted by methyl groups at positions 1 and 3.
Synthesis Reference(s)
Journal of the American Chemical Society, 97, p. 7262, 1975 DOI: 10.1021/ja00858a011
The Journal of Organic Chemistry, 44, p. 2185, 1979 DOI: 10.1021/jo01327a032
Allgemeine Beschreibung
A colorless watery liquid with a sweet odor. Less dense than water. Insoluble in water. Irritating vapor.
Air & Water Reaktionen
Highly flammable. Insoluble in water.
Reaktivität anzeigen
1,2-Dimethylbenzene may react with oxidizing materials. .
Health Hazard
Vapors cause headache and dizziness. Liquid irritates eyes and skin. If taken into lungs, causes severe coughing, distress, and rapidly developing pulmonary edema. If ingested, causes nausea, vomiting, cramps, headache, and coma. Can be fatal. Kidney and liver damage can occur.
Brandgefahr
Behavior in Fire: Vapor is heavier than air and may travel considerable distance to a source of ignition and flash back.
Flammability and Explosibility
Flammable
Chemische Reaktivität
Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Sicherheitsprofil
Moderately toxic bj7 intraperitoneal route. Mldly toxic by ingestion and inhalation. An experimental teratogen. A common air contaminant. A very dangerous fire hazard when exposed to heat or flame. Explosive in the form of vapor when exposed to heat or flame. To fight fire, use foam, CO2, dry chemical. Incompatible with oxidzing materials. When heated to decomposition it emits acrid smoke and irritating fumes. Emitted from modern building materials (CENEAR 69,22,91). See also other xylene entries.
Source
Detected in distilled water-soluble fractions of 87 octane gasoline (3.83 mg/L), 94 octane gasoline (11.4 mg/L), Gasohol (8.49 mg/L), No. 2 fuel oil (1.73 mg/L), jet fuel A (0.87 mg/L), diesel fuel (1.75 mg/L), military jet fuel JP-4 (1.99 mg/L) (Potter, 1996), new motor oil (16.2 to 17.5 μg/L), and used motor oil (294 to 308 μg/L) (Chen et al., 1994). The average volume percent and estimated mole fraction in American Petroleum Institute PS-6 gasoline are 2.088 and 0.01959, respectively (Poulsen et al., 1992). Schauer et al. (1999) reported o-xylene in a diesel-powered medium-duty truck exhaust at an emission rate of 830 μg/km. Diesel fuel obtained from a service station in Schlieren, Switzerland contained o-xylene at a concentration of 223 mg/L (Schluep et al., 2001).
California Phase II reformulated gasoline contained o-xylene at a concentration of 19.7 g/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were 5.41 and 562 mg/km, respectively (Schauer et al., 2002).
Thomas and Delfino (1991) equilibrated contaminant-free groundwater collected from Gainesville, FL with individual fractions of three individual petroleum products at 24–25 °C for 24 h. The aqueous phase was analyzed for organic compounds via U.S. EPA approved test method 602. Average m+p-xylene concentrations reported in water-soluble fractions of unleaded gasoline, kerosene, and diesel fuel were 8.611, 0.658, and 0.228 mg/L, respectively. When the authors analyzed the aqueous-phase via U.S. EPA approved test method 610, average m+p-xylene concentrations in water-soluble fractions of unleaded gasoline, kerosene, and diesel fuel were lower, i.e., 6.068, 0.360, and 0.222 mg/L, respectively. Based on laboratory analysis of 7 coal tar samples, o-xylene concentrations ranged from 2 to 2,000 ppm (EPRI, 1990). A high-temperature coal tar contained o-xylene at an average concentration of 0.04 wt % (McNeil, 1983).
Schauer et al. (2001) measured organic compound emission rates for volatile organic compounds, gas-phase semi-volatile organic compounds, and particle-phase organic compounds from the residential (fireplace) combustion of pine, oak, and eucalyptus. The gas-phase emission rate of o-xylene was 18.1 mg/kg of pine burned. Emission rates of o-xylene were not measured during the combustion of oak and eucalyptus.
Drinking water standard (final): For all xylenes, the MCLG and MCL are both 10 mg/L. In addition, a DWEL of 70 mg/L was recommended (U.S. EPA, 2000).
Environmental Fate
Biological. Reported biodegradation products of the commercial product containing xylene include α-hydroxy-p-toluic acid, p-methylbenzyl alcohol, benzyl alcohol, 4-methylcatechol, mand p-toluic acids (Fishbein, 1985). o-Xylene was also cometabolized resulting in the formation of o-toluic acid (Pitter and Chudoba, 1990). In anoxic groundwater near Bemidji, MI, o-xylene anaerobically biodegraded to the intermediate o-toluic acid (Cozzarelli et al., 1990). In gasolinecontaminated groundwater, methylbenzylsuccinic acid was identified as the first intermediate during the anaerobic degradation of xylenes (Reusser and Field, 2002).
Photolytic. Cox et al. (1980) reported a rate constant of 1.33 x 10^-11 cm³/molecule?sec for the reaction of gaseous o-xylene with OH radicals based on a value of 8 x 10^-12 cm³/molecule?sec for the reaction of ethylene with OH radicals.
Surface Water. The evaporation half-life of o-xylene in surface water (1 m depth) at 25 °C is estimated to be 5.18 h (Mackay and Leinonen, 1975).
Groundwater. Nielsen et al. (1996) studied the degradation of o-xylene in a shallow, glaciofluvial, unconfined sandy aquifer in Jutland, Denmark. As part of the in situ microcosm study, a cylinder that was open at the bottom and screened at the top was installed through a cased borehole approximately 5 m below grade. Five liters of water was aerated with atmospheric air to ensure aerobic conditions were maintained. Groundwater was analyzed weekly for approximately 3 months to determine o-xylene concentrations with time. The experimentally determined firstorder biodegradation rate constant and corresponding half-life following a 7-d lag phase were 0.1/d and 6.93 d, respectively.
Photolytic. When synthetic air containing gaseous nitrous acid and o-xylene was exposed to artificial sunlight (λ = 300–450 nm) biacetyl, peroxyacetal nitrate, and methyl nitrate formed as products (Cox et al., 1980). A n-hexane solution containing o-xylene and spread as a thin film (4 mm) on cold water (10 °C) was irradiated by a mercury medium pressure lamp. In 3 h, 13.6% of the o-xylene photooxidized into o-methylbenzaldehyde, o-benzyl alcohol, o-benzoic acid, and omethylacetophenone (Moza and Feicht, 1989). Irradiation of o-xylene at ≈ 2537 ? at 35 °C and 6 mmHg isomerizes to m-xylene (Calvert and Pitts, 1966). Glyoxal, methylglyoxal, and biacetyl were produced from the photooxidation of o-xylene by OH radicals in air at 25 °C (Tuazon et al., 1986a).
Chemical/Physical. Under atmospheric conditions, the gas-phase reaction of o-xylene with OH radicals and nitrogen oxides resulted in the formation of o-tolualdehyde, o-methylbenzyl nitrate, nitro-o-xylenes, 2,3-and 3,4-dimethylphenol (Atkinson, 1990). Kanno et al. (1982) studied the aqueous reaction of o-xylene and other aromatic hydrocarbons (benzene, toluene, m- and p-xylene, and naphthalene) with hypochlorous acid in the presence of ammonium ion. They reported that the aromatic ring was not chlorinated as expected but was cleaved by chloramine forming cyanogen chloride. The amount of cyanogen chloride formed increased at lower pHs (Kanno et al., 1982). In the gas phase, o-xylene reacted with nitrate radicals in purified air forming the following products: 5-nitro-2-methyltoluene and 6-nitro-2-methyltoluene, o-methylbenzaldehyde, and an aryl nitrate (Chiodini et al., 1993).
läuterung methode
o-Xylene (4.4Kg) is sulfonated by stirring for 4hours with 2.5L of conc H2SO4 at 95o. After cooling, and separating the unsulfonated material, the product is diluted with 3L of water and neutralised with 40% NaOH. On cooling, sodium o-xylene sulfonate separates and is recrystallised from half its weight of water. [A further crop of crystals is obtained by concentrating the mother liquor to one-third of its volume.] The salt is dissolved in the minimum amount of cold water, then mixed with the same amount of cold water, and with the same volume of conc H2SO4 and heated to 110o. o-Xylene is regenerated and steam distils. The distillate is saturated with NaCl, the organic layer is separated, dried and redistilled. [Beilstein 5 H 362, 5 I 179, 5 II 281, 5 III 807, 5 IV 917.]

o-Xylene Upstream-Materialien And Downstream Produkte

o-Xylol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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