ChemicalBook >  Product Catalog >  Organic Chemistry >  Carboxylic acids and derivatives >  Carboxylic acid derivatives >  Benzenesulfonic acid

Benzenesulfonic acid

Basic information Safety Related Supplier

Benzenesulfonic acid Basic information

Product Name:
Benzenesulfonic acid
CAS:
98-11-3
MF:
C6H6O3S
MW:
158.18
EINECS:
202-638-7
Mol File:
98-11-3.mol
More
Less

Benzenesulfonic acid Chemical Properties

Melting point:
30-60 °C
Boiling point:
137℃
Density 
1.32
refractive index 
1.5151 (estimate)
Flash point:
>230 °F
storage temp. 
Store below +30°C.
solubility 
H2O: soluble0.1g/10 mL, clear, colorless
pka
0.7(at 25℃)
form 
Damp Crystalline Solid or Fused Mass
color 
Yellow to light brown
PH
2 (H2O, 20℃)(saturated solution)
Water Solubility 
soluble
Sensitive 
Hygroscopic
Merck 
14,1070
BRN 
742513
Stability:
Stable. Incompatible with strong oxidizing agents, bases, many organic compounds.
InChIKey
SRSXLGNVWSONIS-UHFFFAOYSA-N
CAS DataBase Reference
98-11-3(CAS DataBase Reference)
NIST Chemistry Reference
Benzenesulfonic acid(98-11-3)
EPA Substance Registry System
Benzenesulfonic acid (98-11-3)
More
Less

Safety Information

Hazard Codes 
C
Risk Statements 
22-34
Safety Statements 
26-36/37/39-45-36
RIDADR 
UN 2583 8/PG 2
WGK Germany 
1
RTECS 
DB4200000
TSCA 
Yes
HazardClass 
8
PackingGroup 
III
HS Code 
29041000
Hazardous Substances Data
98-11-3(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 1175 mg/kg

MSDS

More
Less

Benzenesulfonic acid Usage And Synthesis

Description

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.

Chemical Properties

green solid

Definition

ChEBI: The simplest member of the class of a benzenesulfonic acids that consists of a benzene carrying a single sulfo group.

Definition

A white crystalline acid made by sulfonation of benzene. Any further substitution onto the benzene ring is directed into the 3 position.

Definition

benzenesulphonic acid: A colourlessdeliquescent solid, C6H5SO2OH,m.p. 43–44°C, usually found as anoily liquid. It is made by treating benzenewith concentrated sulphuricacid. Its alkyl derivatives are used asdetergents.

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.

Preparation

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.".

Reactions

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

General Description

Deliquescent needles or large plates.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

Benzenesulfonic acid reacts with bases and many organic compounds.

Fire Hazard

Flash point data for Benzenesulfonic acid are not available, however Benzenesulfonic acid is probably combustible.

Safety Profile

Poison by ingestion, sbn contact, and probably inhalation. A severe skin and eye irritant. See also SULFATES and SULFONATES.

Purification Methods

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.]

More
Less

Benzenesulfonic acidSupplierMore

Nanjing Datang Chemical Co., Ltd Gold
Tel:
+86-25-85431992
Email:
vip@chemdatang.com
TCI (Shanghai) Development Co., Ltd. Gold
Tel:
021-67121386 / 800-988-0390
Email:
Sales-CN@TCIchemicals.com
Beijing dtftchem Technology Co., Ltd. Gold
Tel:
13031183356 010-60275820-
Email:
elainezt@sina.com
卡托研究化学公司 Gold
Tel:
4000-868-328 020-81215950-
Email:
customer@uwalab.com;customer@uwalab.com
J & K SCIENTIFIC LTD.
Tel:
400-666-7788 010-82848833-
Email:
jkinfo@jkchemical.com;market6@jkchemical.com
Basic information Safety Related Supplier