Benzolsulfonsäure

Bezeichnung:Benzolsulfonsäure

CAS-Nr98-11-3

Englisch Name:Benzenesulfonic acid

CBNumberCB4668758

SummenformelC6H6O3S

Molgewicht158.18

MOL-Datei98-11-3.mol

Synonyma

Benzolsulfonsure

Benzolsulfonsäure

Benzolmonosulfons?ure

Benzolsulfonsäure physikalisch-chemischer Eigenschaften

Schmelzpunkt	30-60 °C
Siedepunkt	137℃
Dichte	1.32
Dampfdruck	69.8Pa at 20℃
Brechungsindex	1.5151 (estimate)
Flammpunkt	>230 °F
storage temp.	Store below +30°C.
Löslichkeit	H2O: soluble0.1g/10 mL, clear, colorless
Aggregatzustand	Damp Crystalline Solid or Fused Mass
pka	0.7(at 25℃)
Farbe	Yellow to light brown
PH	2 (H2O, 20℃)(saturated solution)
Wasserlöslichkeit	soluble
Sensitive	Hygroscopic
Merck	14,1070
BRN	742513
Stabilität	Stable. Incompatible with strong oxidizing agents, bases, many organic compounds.
InChIKey	SRSXLGNVWSONIS-UHFFFAOYSA-N
LogP	0.41 at 25℃
CAS Datenbank	98-11-3(CAS DataBase Reference)
NIST chemische Informationen	Benzenesulfonic acid(98-11-3)
EPA chemische Informationen	Benzenesulfonic acid (98-11-3)

Sicherheit

Kennzeichnung gefährlicher	C
R-Sätze:	22-34
S-Sätze:	26-36/37/39-45-36
RIDADR	UN 2583 8/PG 2
WGK Germany	1
RTECS-Nr.	DB4200000
TSCA	Yes
HazardClass	8
PackingGroup	III
HS Code	29041000
Giftige Stoffe Daten	98-11-3(Hazardous Substances Data)
Toxizität	LD50 orally in Rabbit: 1175 mg/kg

Gefahreninformationscode (GHS)

Benzenesulfonic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
GRAUE BIS GELBE HYGROSKOPISCHE KRISTALLE ODER FLOCKEN MIT STECHENDEM GERUCH.
CHEMISCHE GEFAHREN
Zersetzung beim Erhitzen unter Bildung giftiger und ätzender Rauche. Starke Säure in wässriger Lösung. Reagiert sehr heftig mit Basen. ätzend. Reagiert sehr heftig mit Oxidationsmitteln. Greift viele Metalle unter Bildung brennbarer/explosionsfähiger Gase an (z.B. Wasserstoff, ICSC-Nr. 0001).
ARBEITSPLATZGRENZWERTE
TLV nicht festgelegt (ACGIH 2005).
MAK nicht festgelegt (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation und durch Verschlucken.
INHALATIONSGEFAHREN
Eine gesundheitsschädliche Partikelkonzentration in der Luft kann beim Versprühen schnell erreicht werden.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Die Substanz verätzt die Augen, die Haut und die Atemwege. ätzend beim Verschlucken.
LECKAGE
Persönliche Schutzausrüstung: Atemschutzgerät, P2-Filter für schädliche Partikel. Gesichtsschutz benutzen. Chemikalienschutzanzug. Verschüttetes Material in Kunststoffbehältern sammeln. Reste mit viel Wasser wegspülen.
R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R34:Verursacht Verätzungen.
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).
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
Benzene sulfonic acid is an organo sulfur compound with the formula C₆H₅SO₃H. It is the simplest aromatic sulfonic acid. It forms colorless deliquescent sheet crystals or a white waxy solid that is soluble in water and ethanol, slightly soluble in benzene and insoluble in carbon disulfide and diethyl ether. It is often stored in the form of alkali metal salts. Its aqueous solution is strongly acidic.
Chemische Eigenschaften
green solid
History
Benzenesulfonic acid was first obtained, together with diphenyl sulfone, by E. M ITSCHERLICH in 1834 by heating benzene with fuming sulfuric acid. The industrially important reaction of benzenesulfonic acid with alkali hydroxide to form phenol (alkali fusion) was developed by A. W_URTZ and A. K_EKULé in 1867 and by P. O. D EGENER in 1878. Until the early 1960s benzenesulfonic acid was used chiefly in the manufacture of phenol. Other phenol syntheses are preferred now.
Verwenden
Benzenesulfonic acid is an aryl sulfonic acid that can be used to form an organic salt with 5,7-dimethyl-1,8-naphthyridine-2-amine, that can be a synthon for developing supramolecular structures. It can also act as a dopant for the polymerization of pyrrole to form poly(pyrrole), a conducting polymer useful in the development of flexible capacitors.
Verwenden
Benzenesulfonic acid is mainly consumed by conversion to other specialty chemicals. A variety of pharmaceutical drugs are prepared as salts of benzenesulfonic acid and are known as besylates or besilates. The alkali metal salt of benzenesulfonic acid was once widely used in the production of phenol. It acts as an acid catalyst for direct esterification of amino acids and peptides.
Application
The alkali metal salt of benzene sulfonic acid was once widely used in the production of phenol :
C₆H₅SO₃Na + 2 NaOH → C₆H₅ONa + Na₂SO₃
C₆H₅ONa + HCl → C₆H₅OH + NaCl
The process has been largely displaced by the Hock process, which generates less waste. Benzene sulfonic acid is mainly consumed by conversion to other specialty chemicals. A variety of pharmaceutical drugs are prepared as salts of benzene sulfonic acid and are known as besylates or besilates.
synthetische
Benzene sulfonic acid is prepared from the sulfonation of benzene using concentrated sulfuric acid :
This conversion illustrates aromatic sulfonation, which has been called "one of the most important reactions in industrial organic chemistry.".
Application
Benzenesulfonic acids are used chiefly as intermediates. They are employed in the manufacture of sulfonic acid amides, hydrazides, and esters; of sulfinic acids, sulfones, phenols, and thiophenols; and of other compounds. Sulfonic acids that are substituted with OH and/or NH 2 groups serve as intermediates in the manufacture of finishing agents, optical brighteners, pickling agents, dyes, tanning agents, water-soluble resins, insecticides, ion-exchange resins, wetting agents, pharmaceuticals, polymeric thickeners, plasticizers, etc. Benzenesulfonic acids are also used as such as acidic catalysts and standardizing agents in dye manufacture.
Definition
Benzenesulfonic acid is the simplest member of the class of benzenesulfonic acid, which consists of benzene carrying a single sulfur group. It is a colourless deliquescent solid made by sulfonation of benzene, C6H5SO2OH,m.p. 43–44°C, usually found as an oily liquid. It is made by treating benzene with concentrated sulphuric acid, and Its alkyl derivatives are used as detergents. Any further substitution onto the benzene ring is directed into the 3 position.
Reaktionen
Benzene sulfonic acid exhibits the reactions typical of other aromatic sulfonic acids, forming sulfonamides , sulfonyl chloride, and esters. The sulfonation is reversed above 220 °C. Dehydration with phosphorus pentoxide gives benzene sulfonic acid anhydride ((C₆H₅SO₂)₂O). Conversion to the corresponding benzene sulfonyl chloride (C₆H₅SO₂Cl) is effected with phosphorus penta chloride. It is a strong acid, being dissociated in water.
Synthesis Reference(s)
The Journal of Organic Chemistry, 61, p. 1530, 1996 DOI: 10.1021/jo9520710
Tetrahedron Letters, 19, p. 1211, 1978 DOI: 10.1016/S0040-4039(01)94501-0
Allgemeine Beschreibung
Deliquescent needles or large plates.
Air & Water Reaktionen
Slightly soluble in water.
Reaktivität anzeigen
Benzenesulfonic acid reacts with bases and many organic compounds. Benzenesulfonic acid has the characteristic reactions of a strong aromatic sulfonic acid. Acid hydrolysis at 175 ℃ splits it into benzene and sulfuricacid. Additional sulfonation with fuming sulfuric acid gives 1,3-benzenedisulfonic acid, which reacts further to 1,3,5-benzenetrisulfonic acid, and also diphenyl sulfone disulfonic acid.
Benzenesulfonic acid reacts with benzene to form diphenyl sulfone according to a Friedel – Crafts-type reaction.
Benzenesulfonic acid reacts with alkali metal hydroxide at 320 – 350 ℃ to form sodium phe- nolate. This reaction was used in the first industrial synthesis of phenol.
Brandgefahr
Flash point data for Benzenesulfonic acid are not available, however Benzenesulfonic acid is probably combustible.
Flammability and Explosibility
Non flammable
Sicherheitsprofil
Poison by ingestion, sbn contact, and probably inhalation. A severe skin and eye irritant. See also SULFATES and SULFONATES.
läuterung methode
Purify benzenesulfonic acid by dissolving it in a small volume of distilled H2O and stirring with slightly less than the theoretical amount of BaCO3. When effervescence is complete and the solution is still acidic, filter off the insoluble barium benzenesulfonate. The salt is collected and dried to constant weight in vacuo, then suspended in H2O and stirred with a little less than the equivalent (half mol.) of sulfuric acid. The insoluble BaSO4 (containing a little barium benzenesulfonate) is filtered off and the filtrate containing the free acid is evaporated in a high vacuum. The oily residue will eventually crystallise when completely anhydrous. A 32% commercial acid is allowed to fractionally crystallise at room temperature over P2O5 in a vacuum desiccator giving finally colourless deliquescent plates m 52.5o. The anhydrous crystalline acid is deliquescent and should be stored over anhydrous Na2SO4 in the dark and should be used in subdued sunlight as it darkens under sunlight. The main impurity is Fe which readily separates as the Fe salt in the early fractions [Taylor & Vincent J Chem Soc 3218 1952]. The S-benzylisothiuronium salt has m 148o (from EtOH/H2O). It is an IRRITANT to the skin and eyes. [See Adams & Marvel Org Synth Coll Vol I 84 1941, Michael & Adair Chem Ber 10 585 1877, Beilstein 11 IV 27.]
Waste disposal
Benzenesulfonic acid is biologically degradable. If the desired benzenesulfonic acid can be precipitated from sulfuric acid solution without salt being added, the spent acid can be upgraded in a sulfuric acid recovery plant. If the wastewater contains salts and nondegradable sulfonic acids, low-pressure wet oxidation is a possible method of treatment that subsequently allows effective degradation in wastewater treatment works.

Benzenesulfonic acid Upstream-Materialien And Downstream Produkte

Benzolsulfonsäure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

98-11-3, Benzenesulfonic acid Verwandte Suche:

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