Benzolsulfons?ure 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 ?tzender Rauche. Starke S?ure in w?ssriger L?sung. Reagiert sehr heftig mit Basen. ?tzend. Reagiert sehr heftig mit Oxidationsmitteln. Greift viele Metalle unter Bildung brennbarer/explosionsf?higer Gase an (z.B. Wasserstoff, ICSC-Nr. 0001).
ARBEITSPLATZGRENZWERTE
TLV nicht festgelegt (ACGIH 2005).
MAK nicht festgelegt (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den K?rper durch Inhalation und durch Verschlucken.
INHALATIONSGEFAHREN
Eine gesundheitssch?dliche Partikelkonzentration in der Luft kann beim Versprühen schnell erreicht werden.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION: Die Substanz ver?tzt die Augen, die Haut und die Atemwege. ?tzend beim Verschlucken.
LECKAGE
Pers?nliche Schutzausrüstung: Atemschutzger?t, P2-Filter für sch?dliche Partikel. Gesichtsschutz benutzen. Chemikalienschutzanzug. Verschüttetes Material in Kunststoffbeh?ltern sammeln. Reste mit viel Wasser wegspülen.
R-S?tze Betriebsanweisung:
R22:Gesundheitssch?dlich beim Verschlucken.
R34:Verursacht Ver?tzungen.
S-S?tze 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 m?glich, dieses Etikett vorzeigen).
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
Benzene sulfonic acid is an organo sulfur compound with the formula C
6H
5SO
3H. 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 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 :
C
6H
5SO
3Na + 2 NaOH → C
6H
5ONa + Na
2SO
3 C
6H
5ONa + HCl → C
6H
5OH + 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.
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 ((C
6H
5SO
2)
2O). Conversion to the corresponding benzene sulfonyl chloride (C
6H
5SO
2Cl) is effected with phosphorus penta chloride. It is a strong acid, being dissociated in water.
Allgemeine Beschreibung
Deliquescent needles or large plates.
Air & Water Reaktionen
Slightly soluble in water.
Reaktivit?t 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.
Sicherheitsprofil
Poison by ingestion,
sbn contact, and probably inhalation. A
severe skin and eye irritant. See also
SULFATES and SULFONATES.
l?uterung 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.]
Benzolsulfons?ure Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
Tetranatrium-4,4'-bis[[4-[bis(2-hydroxyethyl)amino]-6-(4-sulfonatoanilino)-1,3,5-triazin-2-yl]amino]stilben-2,2'-disulfonat]
synthetic tanning agent No.29
Hydrogen[4-[4-(p-ethoxyanilino)-4'-[ethyl(m-sulfonatobenzyl)amino]benzhydrylen]cyclohexa-2,5-dien-1-yliden](ethyl)(m-sulfonatobenzyl)ammonium, Mononatriumsalz
9,10-Dihydro-9,9-dimethylacridin
3,8-Diamino-5-methyl-6-phenylphenanthridiniumbromid
Stearinsure
Dinatrium-6-hydroxy-5-[[4-[[4-(phenylamino)-3-sulfonatophenyl]azo]naphthyl]azo]naphthalin-2-sulfonat
(Z)-4-Decenal
Ethoxychin
LANASOLBLUE3R
N5-[Imino(phosphonoamino)methyl]L-ornithin
4,4'-Diamino-diphenyl-methan
Vanillin
Ammoniumhydrogencarbonat
N-Butylbenzolsulfonamid
diethyl 2,6-bis((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
AtracuriuM IMpurity D2 (cis-Quaternary Alcohol)
Diphenylsulfon
Trimethylsilylbenzolsulfonat
