2,6-Dichlorbenzonitril Chemische Eigenschaften,Einsatz,Produktion Methoden
ERSCHEINUNGSBILD
WEISSE BIS CREMEFARBENE KRISTALLE MIT CHARAKTERISTISCHEM GERUCH.
CHEMISCHE GEFAHREN
Zersetzung beim Erhitzen unter Bildung giftiger und ätzender Rauche mit Chlorwasserstoff. Reagiert sehr heftig mit Oxidationsmitteln.
ARBEITSPLATZGRENZWERTE
TLV nicht festgelegt (ACGIH 2005).
MAK nicht festgelegt (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation, über die Haut und durch Verschlucken
INHALATIONSGEFAHREN
Eine gesundheitsschädliche Partikelkonzentration in der Luft kann beim Dispergieren schnell erreicht werden.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Möglich sind Auswirkungen auf die Haut mit nachfolgender Chlorakne.
LECKAGE
Persönliche Schutzausrüstung: Atemschutzgerät, P2-Filter für schädliche Partikel. NICHT in die Umwelt gelangen lassen. Verschüttetes Material in abdichtbaren Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Reste sorgfältig sammeln. An sicheren Ort bringen.
R-Sätze Betriebsanweisung:
R21:Gesundheitsschädlich bei Berührung mit der Haut.
R51/53:Giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
S-Sätze Betriebsanweisung:
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
Chemische Eigenschaften
2,6-Dichlorobenzonitrile [1194-65-6], 1- cyano-2,6-dichlorobenzene, Mr 172.02, mp 144.5 –146.5 ℃, is a colorless, crystalline substance. Its solubility in water is 10 ppm at 25℃. 2,6-Dichlorobenzonitrile is produced industrially by the ammoxidation of 2,6-dichlorotoluene. In addition the nitrile is obtained by oxidation or side-chain-chlorination of 2,6-dichlorotoluene via 2,6-dichlorobenzoic acid and 2,6-dichlorobenzaldehyde, respectively. 2,6-Dichlorobenzonitrile shows herbicidal activity (Casoron, Duphar) and is used in fruit and vine cultivation. It is also used as an intermediate in the production of 2,6-difluorobenzonitrile and of 2,6-dichlorothiobenzamide (Prefix, Shell) which shows herbicidal activity.
Verwenden
2,6-dichlorobenzonitrile in which Q-amino-G- chlorobenzonitrile is used as starting material. And it is used for the synthesis of diclofenac sodium oxacillin and guanabenz acetate.
Definition
ChEBI: A nitrile that is benzonitrile which is substituted by chlorines at positions 2 and 6. A cellulose synthesis inhibitor, it is used as a pre-emergent and early post-emergent herbicide.
Allgemeine Beschreibung
2,6-Dichlorobenzonitrile is a white solid dissolved or suspended in a water-emulsifiable liquid carrier. The primary hazard is the threat to the environment. Immediate steps should be taken to limit spread to the environment. Can easily penetrate the soil and contaminate groundwater and nearby streams. Can cause illness by inhalation, skin absorption and/or ingestion. Used as a herbicide.
Air & Water Reaktionen
Not soluble in water.
Reaktivität anzeigen
A halogenated nitrile. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.
Health Hazard
SOLID: Harmful if swallowed.
Brandgefahr
Not flammable.
Landwirtschaftliche Anwendung
Herbicide: Dichlobenil is a herbicide used on cranberry bogs,
dichondra, ornamentals, blackberry, raspberry, and blueberry
fields, apple, pear, filbert and cherry orchards,
vineyards, hybrid poplar-cottonwood plantations, and
rights-of-way to control weeds; and sewers to remove
roots. It acts on dandelion, prickly oxtongue (pre-emergence),
and tree roots. Not approved for use in EU countries.
Actively registered in the U.S.
Handelsname
BARRIER®; BH Prefix D®;
CARSORON®; CASORON® 133; CARSORON® G;
CARSORON® G4; CARSORON® G20-SR; CODE H
133®; DECABANE®; DU-SPREX®; DYCLOMEC®;
FYDULAN; FYDUMAS; FYDUSIT; H 133®; H 1313®;
NIA 5996®; NIAGARA® 5006; NIAGARA 5,996;
NOROSAC®; PREFIX D®
Stoffwechselwegen
Twelve metabolites are isolated from either urine or
bile from either rats (11 metabolites) or goats (seven
metabolites) given single oral doses of 14C-labeled
2,6-dichlorobenzonitrile (DCBN). Five of these
metabolites are also excreted in urine from rats dosed
orally with 2,6-dichlorothiobenzamide (DCTBA) which
is an acid amide analog. All metabolites from either DCBN or DCTBA are benzonitriles with the following
ring substituents: Cl2, OH (three isomers); Cl2, (OH)2;
Cl, (OH)2; Cl, OH, SH; Cl, OH, SCH3; SOCH3, OH;
Cl2, S-(N-acetyl)cysteine; Cl, S-(N-acetyl)cysteine; Cl,
OH, S-(N-acetyl)cysteine.
The thiobenzamide moiety of DCTBA is converted
to the nitrile in all extracted urinary metabolites. No
hydrolysis of the nitrile in DCBN to either amide or an
acid is detected. Urine is the major route for excretion;
however, enterohepatic circulation occurs.
läuterung methode
Crystallise the nitrile from acetone. [Beilstein 9 IV 1006.]
2,6-Dichlorbenzonitril Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
