Benzolsulfonsäurechlorid Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R20/22:Gesundheitsschädlich beim Einatmen und Verschlucken.
R34:Verursacht Verätzungen.
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
R29:Entwickelt bei Berührung mit Wasser giftige Gase.
R22:Gesundheitsschädlich beim Verschlucken.
S-Sätze Betriebsanweisung:
S23:Gas/Rauch/Dampf/Aerosol nicht einatmen(geeignete Bezeichnung(en) vom Hersteller anzugeben).
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).
Aussehen Eigenschaften
C6H5ClO2S; Benzolsulfochlorid. Farblose Flüssigkeit mit stechendem Geruch.
Gefahren für Mensch und Umwelt
Gesundheitsschädlich beim Verschlucken. Verursacht Verätzungen. Nach Einatmen Atemnot und Husten.
LD
50 (oral, Ratte): 1950 mg/kg
Schutzmaßnahmen und Verhaltensregeln
Geeignete Schutzhandschuhe als kurzzeitiger Spritzschutz.
Verhalten im Gefahrfall
Dämpfe nicht einatmen.
Mit flüssigkeitsbindendem Material, z.B. Rench Rapid aufnehmen. Der Entsorgung zuführen. Nachreinigen.
Kohlendioxid, Wasser, Pulver.
Brennbar. Im Brandfall können Chlorwasserstoff und Schwefeldioxid freigesetzt werden.
Erste Hilfe
Nach Hautkontakt: Mit reichlich Wasser abwaschen. Abtupfen mit Polyethylenglycol 400.
Nach Augenkontakt: Mit reichlich Wasser bei geöffnetem Lidspalt mindestens 10 Minuten ausspülen. Sofort Arzt hinzuziehen.
Nach Einatmen: Frischluft. Arzt hinzuziehen.
Nach Verschlucken: Reichlich Wasser trinken lassen. Erbrechen vermeiden (Perforationsgefahr!). Sofort Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminierte Kleidung sofort entfernen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Als halogenhaltige, organische Lösemittelabfälle entsorgen.
Chemische Eigenschaften
Benzenesulfonyl chloride is a colorless oily liquid with a pungent odor. Insoluble in water, soluble in ethanol and ether. Can react with ammonia, amine and alcohol to produce benzenesulfonamide and benzene sulfonate respectively. It is toxic, irritates skin, eyes and mucous membranes, corrosive, and can cause burns. Oral LD50 1960mg/kg in rats.
Verwenden
Benzenesulfonyl chloride reacts with Grignard reagents to form oxindoles from N-unsubstituted indoles. It is widely used to check the assay of thiamine in different food products. It is involved in the synthesis of alpha-disulfones, sulfonamides and sulfoante esters as precursor. It is a derivatization reagent for the determination of various amines in waste water and surface water at the sub-ppb level by gas chromatography-mass spectrometry. It is common reagent used in Hinsberg test for detection and distinguishing the type of amines as primary, secondary and tertiary amines.
Vorbereitung Methode
The most convenient method for the production of benzenesulfonyl chlorides is the chlorosulfonation reaction of benzene or substituted benzene with chlorosulfuric acid. Sulfonation and formation of the sulfonyl chlo- ride take place in one reaction sequence:
Ar-H+Cl-SO
3H→ArSO
3H+HCl
ArSO
3H+Cl-SO
3H=ArSO
2Cl+H
2SO
4
Sulfone is formed in a side reaction of the chlorosulfonation. The amount of sulfone formation can be reduced by diluting with a solvent, by using a large excess of chlorosulfuric acid, or by adding sulfone-inhibiting substances, e.g., alkali metal and ammonium salts, acetic acid, phosphoric acid, dimethylformamide, or amidosulfuric acid.
For industrial chlorosulfonation the chlorosulfuric acid is introduced into a cast-steel or enameled steel vessel and 10 – 25 mol% of the aromatic compound is stirred in at 25 – 30 ℃, whereupon sulfonation of the aromatic compound and HCl formation occur. The formation of sulfonyl chloride is initiated by heating the reactants to 50 – 80 ℃. The reaction is exothermic. The sulfonyl chloride is isolated by draining the reaction mass onto water and simultaneous cooling. Excess chlorosulfuric acid is decomposed, and the sulfonyl chloride either precipitates or separates as an organic liquid phase. The quality of the chlorosulfuric acid affects the yield.
Other chlorinating agents, such as phosgene, thionyl chloride, sulfuryl chloride, or phosphorus pentachloride, can be used instead of chlorosulfu- ricacid. When thionyl chloride is used the sulfonyl chloride is obtained from the sulfonic acid in high yield and without formation of sulfuric acid.
Allgemeine Beschreibung
A colorless to slightly yellow solid that melts at approximately 40°F. Very irritating to skin, eyes and mucous membranes. May emit toxic fumes when heated to high temperatures. Used to make dyes and other chemicals.
Air & Water Reaktionen
Insoluble and stable in cold water [Merck]. Decomposes in hot water to produce corrosive and toxic hydrochloric acid and benzenesulfonic acid. Rate of reaction decreases as temperature decreases.
Reaktivität anzeigen
Benzenesulfonyl chloride is incompatible with strong oxidizing agents and bases, including amines. Corrodes metals in the presence of water due to slow formation of hydrochloric acid and benzenesulfonic acid [USCG, 1999]. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].
Health Hazard
May be fatal if inhaled, swallowed or absorbed through skin. Contact may cause skin and eye burns. Irritating to eyes, skin and mucous membranes. INGESTION: May cause abdominal spasm and vomiting.
Sicherheitsprofil
Poison by intraperitoneal route. Adangerous storage hazard. It may explode in a sealedbottle. Explosive reaction with dimethyl sulfoxide. Reactsvigorously with methyl formamide. When heated todecomposition it emits toxic fumes of Cl
- and SO
mögliche Exposition
It is used as a chemical intermediate
for benzenesulfonamides, thiophenol, glybuzole (hypoglycemic
agent), N-2-chloroehtylamides, benzonitrile; for its
esters-useful as insecticides, and miticides.
Versand/Shipping
UN2225 Benzene sulfonyl chloride, Hazard
class: 8; Labels: 8—Corrosive material.
läuterung methode
Distil the sulfonyl chloride, then treat it with 3mole % each of toluene and AlCl3, and allow it to stand overnight. The sulfonyl chloride is distilled off at 1mm pressure and then carefully fractionally distilled at 10mm in an all-glass column. [Adams & Marvel Org Synth Coll Vol I 84 1941, Jensen & Brown J Am Chem Soc 80 4042 1958, Beilstein 11 IV 49.] It is TOXIC.
Inkompatibilitäten
Violent reaction with strong oxidizers,
dimethyl sulfoxide, and methyl formamide. It is very reactive
with bases and many organic compounds. Incompatible
with ammonia, aliphatic amines. Water contact forms
hydrochloric and chlorosulfonic acids. Aqueous solutions
of this chemical are strong acids that react violently with
bases. Attacks metals in presence of moisture.
Benzolsulfonsäurechlorid Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
2-(2,3-DIHYDRO-1BENZENESULFONYL-PYRROLO[2,3-B]PYRIDIN-3-YL)ETHANAMINE
Salazosulfapyridin
2-Methyl-4-nitrobenzoldiazonium
(Trifluoromethyl)trimethylsilane
17-Hydroxypregna-4,9(11)-dien-3,20-dion
2-(2-CHLOROETHOXY)-BENZENESULFONAMIDE
N-(Phenylsulfonyl)benzolsulfonamid
Sulfachinoralin
Thiophenol
16alpha,17-epoxypregna-4,9(11)-diene-3,20-dione
Benzolsulfonamid
3-Nitro-o-toluidin
Benzolsulfonsäure-hydrazid
Natriumbenzolthiosulfonat
O-Ethyl-S,S-diphenyl-dithiophosphat
2,4-Dichlor-5-sulfamoylbenzoesure
dimethyl p-octadecyl phenylsulfonyl amino propyl ammoium propylsulfonate
Tosylchlorid
Acid Yellow 79
4-Nitro-o-toluidin
2-(2,3-DIHYDRO-1-BENZENESULFONYL-PYRROLO[2,3-B]PYRIDIN-3-YL)ACETONITRILE
Permanent Violet RL
Leuprorelin
Benzenesulfonylazide
1-(PHENYLSULFONYL)-1H-INDOLE-2-CARBALDEHYDE
Natriumbenzolsulfinat
Nitrotoluidin
2,5-Dichlorpyridin
