BENZENESULFONIC ACID
BENZENESULFONIC ACID
CAS Number: 98-11-3
EC Number: 202-638-7
Linear Formula: C6H5SO3H
Molecular Weight: 158.18
Benzenesulfonic acid (conjugate base benzenesulfonate) is an organosulfur compound with the formula C6H6O3S.
Benzenesulfonic acid is the simplest aromatic sulfonic acid.
Benzenesulfonic acid forms white deliquescent sheet crystals or a white waxy solid that is soluble in water and ethanol, slightly soluble in benzene and insoluble in nonpolar solvents like diethyl ether.
Benzenesulfonic acid is often stored in the form of alkali metal salts.
Benzenesulfonic acids aqueous solution is strongly acidic.
Benzenesulfonic acid is a colorless crystalline acid C6H5SO3H made by sulfonating benzene and used in organic synthesis, in the form of its besylate in pharmacology, and in the form of derivatives as detergents
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.
Benzenesulfonic acid 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.
Uses of Benzenesulfonic acid
Salts of Benzenesulfonic acid such as Sodium benzenesulfonate (Ludigol) and Monoethanolamine benzenesulfonate are used as surfactants in laundry detergent.
A variety of pharmaceutical drugs are prepared as benzenesulfonate salts and are known as besilates (INN) or besylates (USAN).
In a diluted form, Benzenesulfonic acid is also used as a polymer remover stripping agent.
Benzenesulfonic acid Uses:
-In the manufacture of dyes
-Sulpha drugs are prominent in the manufacture of drugs.
-In manufacture of saccharine
-In the manufacture of detergents
Preparation
Benzenesulfonic 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”.
Preferred IUPAC name
Benzenesulfonic acid
Other names
Benzene sulphonic acid; Benzenesulphonic acid; Phenylsulfonic acid; Phenylsulphonic acid; Besylic acid
Benzenesulfonic acid is used for surfactant enhanced oil recovery (SEOR), also known as surfactant flushing.
Surfactant use allows for enhanced recovery of large volumes of LNAPL (petroleum hydrocarbons).
In a typical application, multiple injection wells are installed, as well as multiple hydraulic control wells and multiple recovery wells.
Design involves groundwater flow modeling, tracer testing, and establishment of a constant forced-gradient flow field through the NAPL smear zone.
A polymer solution (guar gum or xanthum gum) is injected to create a viscous plug flow behind the surfactant for the purpose of improving sweep efficiency and accelerating the recovery of NAPL and surfactant.
Benzenesulfonic acid is biodegradable and does not degrade into benzene (the benzene ring breaks down first).
The surfactant is low in toxicity (LD50 >2000 mg/kg).
USEPA has determined that Benzenesulfonic Acid is a Safer Chemical Ingredient for Surfactant use and meets the criteria of the Design for the Environment.
Benzenesulfonic acid can cause irritation to skin and lungs so use of proper PPE is important when handling the material.
Chemical formula: C6H6O3S
Molar mass: 158.17 g·mol−1
Appearance: Colorless crystalline solid
Density: 1.32 g/cm3 (47 °C)
Melting point:
44 °C (hydrate)
51 °C (anhydrous)
Boiling point: 190 °C (374 °F; 463 K)
Solubility in water: Soluble
Solubility in other solvents: Soluble in alcohol, insoluble in non-polar solvents
Acidity (pKa): −2.8
Reactions
Benzenesulfonic 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 benzenesulfonic acid anhydride ((C6H5SO2)2O).
Conversion to the corresponding benzenesulfonyl chloride (C6H5SO2Cl) is effected with phosphorus pentachloride.
Benzenesulfonic acid is a strong acid, being almost fully dissociated in water.
Benzenesulfonic acid and related compounds undergo desulfonation when heated in water near 200 °C.
The temperature of desulfonation correlates with the ease of the sulfonation:
C6H5SO3H + H2O → C6H6 + H2SO4
Because of that, sulfonic acids are usually used as a protecting group, or as a meta director in electrophilic aromatic substitution.
The alkali metal salt of benzenesulfonic acid was once used in the industrial production of phenol.
The process, sometimes called alkaline fusion, initially affords the phenoxide salt:
C6H5SO3Na + 2 NaOH → C6H5ONa + Na2SO3
C6H5ONa + HCl → C6H5OH + NaCl
The process has been largely displaced by the Hock process, which generates less waste.
Synonyms: Benzenesulfonic acid
Linear Formula: C6H5SO3H
CAS Number: 98-11-3
Molecular Weight: 158.18
CAS Number: 98-11-3
CHEBI:64455
ChEMBL: ChEMBL1422641
ChemSpider: 7093
ECHA InfoCard: 100.002.399
EC Number: 202-638-7
PubChem CID: 7371
RTECS number: DB4200000
UNII: 685928Z18A
UN number: 2583, 2585, 1803
CompTox Dashboard (EPA): DTXSID9024568
Benzenesulfonic acid is obtained from sulphonation of benzene.
For this, benzene is heated with concentrated Sulfuric acid.
To make Benzenesulfonic acid in the laboratory, take a mixture of one part banzene and two parts concentrated sulfuric acid in a round bottom flask.
Attaches a reflux condenser to the flask.
Heat the flask at 80 -100°C for about two hours by placing it on a water heater.
After this, the mixture is cooled and put in water.
Benzenesulfonic acid contains barium carbonate.
Unused sulfuric acid precipitates as barium sulfate.
Filter it and separate Benzenesulfonic acid.
Berium salt of Benzenesulfonic acid is filtered due to dissolution in water.
On cooling after filtration, the cristal of Benzenesulfonic acid’s berium salt is obtained, separating these crystals and adding appropriate amounts of sulphuric acid.
Berium sulfate precipitates and Benzenesulfonic acid is released.
The precipitates of berium sulfate are filtered and separated.
Water containing crystals of Benzenesulfonic acid are obtained after cooling the filtrate.
Anhydrous Benzenesulphonic(C6H5SO3H.3/2H2O) Acid is obtained after being isolated and heated.
Physical Properties
Benzenesulfonic acid is a colorless crystal solid.
Benzenesulfonic acids melting point is 65°C.
Benzenesulfonic acids water-containing crystals have a melting point of 47°C.
Benzenesulfonic acid is more soluble in water.
CAS Number: 98-11-3
Molecular Formula: C6H6O3S
Molecular Weight: 158.170 g/mol
InChI Key: SRSXLGNVWSONIS-UHFFFAOYSA-N
LogP: -0.495
Synonyms:
Benzenesulfonic acid
98-11-3
4-11-00-00027
acide benzenesulfonique
acido bencenosulfonico
Benzenemonosulfonic acid
benzenesulphonic acid
Benzensulfonic acid
BENZOLSULFONSAEURE
Benzolsulfonsaure
Besylic acid
Phenylsulfonic acid
PHENYLSULPHONIC ACID
Benzene sulphonic acid
BRN 0742513
EINECS 202-638-7
Kyselina benzensulfonova
UNII-685928Z18A
Blu-gard snitizing teat dip
Synonym(s): Phenylsulfonic acid
Linear Formula: C6H5SO3H
CAS Number: 98-11-3
Molecular Weight: 158.18
Beilstein/REAXYS Number: 742513
EC Number: 202-638-7
MDL number: MFCD00011689
PubChem Substance ID: 57647013
NACRES: NA.22
Description
Benzene sulfonic acid is an organo sulfur compound with the formula C6H5SO3H.
Benzenesulfonic acid is the simplest aromatic sulfonic acid.
Benzenesulfonic acid 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.
Benzenesulfonic acid is often stored in the form of alkali metal salts.
Benzenesulfonic acids 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.
Benzenesulfonic acid is made by treating benzenewith concentrated sulphuricacid.
Benzenesulfonic acids 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.
Benzenesulfonic acid is a strong acid, being dissociated in water.
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.
Its chemical reactions can be divided into three parts.
Reactions in which the -OH group of the -SO3H group participates.
Reactions in which the –SO3H group is displaced.
Replacement reactions of nuclei
Reactions in which the -OH group of the -SO3H group participates.
Acidic symptoms: Benzenesulfonic acid is an acid.
Benzenesulfonic acids aqueous solution is strongly acidic.
The acid strength of Benzenesulfonic acids aqueous solution is as high as sulphuric acid.
Benzenesulfonic acid reacts with bases to form salts.
example:
C6H5SO3H + NaOH → C6H5SO3Na + H2O
Reaction with Phosphorus pentachloride: In the reaction of Benzenesulfonic acid and phosphorus pentachloride, the -OH group of -SO3H group is displaced by the chlorine atom.
C6H5SO3H + PCl5 → C6H5SO2Cl + POCl3 + HCl
Reaction with alcohols: Like other acids it reacts with alcohols to form ester.
C6H5SO3H + C2H5OH → C6H5 – SO2 –O – C2H5 + H2O
Reactions in which the –SO3H group is displaced.
Displacement by hydrogen atom: On decomposition of benzene sulphonic acid with superheated steam or heating with dilute HCl or dilute H2SO4, its water decomposition occurs and benzene is obtained.
C6H5SO3H + H2O → C6H6 + H2SO4
Displacement by Hydroxyl Group: Phenol is obtained by melting Benzenesulfonic acids sodium or potassium salts with solid NaOH or KOH.
C6H5SO3Na + NaOH → C6H5OH + Na2SO3
Displacement by amines group: Aniline is obtained by melting Benzenesulfonic acids sodium or potassium salts with NaNH2 or KNH2.
C6H5SO3Na + NaNH2 → C6H5NH2 + Na2SO3
Displacement by cyano group: Cyano benzene is obtained by melting Benzenesulfonic acids sodium or potassium salts with NaCN.
C6H5SO3Na + NaCN → C6H5CN + Na2SO3
Displacement by carboxyle group: Benzenesulfonic acids sodium or potassium salts are smelted with sodium phomate to obtain benzoic acid.
C6H5SO3Na + HCOONa → C6H5COOH + Na2SO3
Displacement by -SN group: thaophenol is obtained by melting Benzenesulfonic acids sodium or potassium salts with KSH.
C6H5SO3K + KSH → C6H5SH + K2SO3
Replacement reactions of nuclei
The sulphonic acid group is a meta director group.
Hence meta products are obtained from its halogenation, nitration and sulphonation.
Like all other meta director groups, Benzenesulfonic acid is also a deactivating group.
This implies that Benzenesulfonic acids substitution reactions occur at a lower intensity than benzene.
Following are its major nuclear substitution reactions.
Halogenation: When replicated with chlorine in the presence of halogen carrier, it forms meta chlorobenzene sulphonic acid.
meta-chlorobenzene-sulphonic-acid
Nitration: When heated with a mixture of concentrated NHO3 and concentrated H2SO4, it forms m nitrobenzene sulphonic acid.
Nitrobenzene-sulphoric-acid
sulphonation: when heated at 200°C with gentle sulphuric acid, it forms meta benzene di sulphonic acid.
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 Benzenesulfonic acid 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.
The S-benzylisothiuronium salt has m 148o (from EtOH/H2O).
Benzenesulfonic acid is an IRRITANT to the skin and eyes.
Quality Level: 200
assay: 98.0% (T)
impurities: ≤1.0% water
SMILES string: OS(=O)(=O)c1ccccc1
InChI: 1S/C6H6O3S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H,7,8,9)
InChI key: SRSXLGNVWSONIS-UHFFFAOYSA-N
BENZENESULFONIC ACID
98-11-3
Benzenesulphonic acid
Phenylsulfonic acid
Besylic acid
Benzene sulphonic acid
Benzenemonosulfonic acid
Benzene sulfonic acid
benzensulfonic acid
Kyselina benzensulfonova
UNII-685928Z18A
MFCD00011689
CHEBI:64455
685928Z18A
DSSTox_CID_4568
DSSTox_RID_77453
DSSTox_GSID_24568
Benzenesulfonic acid, 90%, technical
CAS-98-11-3
CCRIS 4595
Kyselina benzensulfonova [Czech]
HSDB 2642
EINECS 202-638-7
Blu-gard snitizing teat dip
BRN 0742513
AI3-15297
Blu-shield (teat dip) solution
benzenesulphonicacid
17-120A
phenyl sulfonic acid
benzolsulfonsäure
Ph-SO3H
EC 202-638-7
SCHEMBL2509
C6H6SO3
4-11-00-00027 (Beilstein Handbook Reference)
$l^{1}-oxidanylsulfonylbenzene
CHEMBL1422641
DTXSID9024568
Chemical Nature Mixture of salt of Naphthalene Sulphonic Acid and Phenol Sulphonic Acid condensation product.
Color Brownish
Physical Appearance Powder
Solubility (10% solution in water) Should be clear
pH (10% solution in water) 6.5 – 7.5
Active Content (U.V. method) 75 % min.
Phenylsulfonic Acid, Besylic Acid
AMY20768
BCP30635
CS-D1398
STR07703
ZINC1555312
Benzenesulfonic acid, 98.0% (T)
Tox21_201960
Tox21_303131
7662AF
ANW-43958
STL280343
AKOS015856636
LS10672
MCULE-3169739755
NCGC00091687-01
NCGC00091687-02
NCGC00256989-01
NCGC00259509-01
Benzenesulfonic acid, technical grade, 90%
B0030
B3408
FT-0622648
Formula: C6H6O3S
Molecular mass: 158.2
Boiling point: 190°C
Melting point: 51°C
Relative density (water = 1): 1.3 (47°C)
Solubility in water, g/100ml at 20°C: 93
Relative vapour density (air = 1): 5.5
Flash point: 113°C
Octanol/water partition coefficient as log Pow: -1.2
Benzenesulfonic acid is used in chemical synthesis, in the personal-domestic use industry, and as a detergent (after neutralization).
Benzenesulfonic acid is used to make linear alkylbenzene sulfonate (LAS) surfactants.
Benzenesulfonic acid is used as an active (disinfectant-antimicrobial and wood preservative) and inert (residential and agricultural end-use products) component in pesticide products.
Benzenesulfonic acid is used in hydraulic fluids, lubricants-greases, and metalworking fluids.
Benzenesulfonic acid, technical, >=90% (T)
11030-EP2269610A2
11030-EP2269986A1
11030-EP2269988A2
11030-EP2269989A1
11030-EP2269990A1
11030-EP2270008A1
11030-EP2270505A1
11030-EP2272537A2
11030-EP2272822A1
11030-EP2275401A1
11030-EP2275411A2
11030-EP2275413A1
11030-EP2275418A1
11030-EP2275424A1
11030-EP2277848A1
11030-EP2277858A1
11030-EP2280009A1
11030-EP2280012A2
11030-EP2281563A1
11030-EP2281817A1
Melting Point: 59°C
Color: White-Yellow
UN Number: 2585
Formula Weight: 158.17
Physical Form: Crystal-Powder at 20°C
Percent Purity: ≥98.0% (T)
Chemical Name or Material: Benzenesulfonic Acid Anhydrous
11030-EP2281819A1
11030-EP2281823A2
11030-EP2284174A1
11030-EP2287147A2
11030-EP2287152A2
11030-EP2287153A1
11030-EP2287155A1
11030-EP2287156A1
11030-EP2287160A1
11030-EP2289510A1
11030-EP2289518A1
11030-EP2289890A1
11030-EP2289894A2
11030-EP2292231A1
11030-EP2292234A1
11030-EP2292611A1
11030-EP2292617A1
11030-EP2292619A1
11030-EP2295406A1
11030-EP2295416A2
11030-EP2298731A1
11030-EP2298742A1
11030-EP2298747A1
11030-EP2298748A2
11030-EP2298755A1
11030-EP2298763A1
11030-EP2298768A1
11030-EP2298772A1
11030-EP2301544A1
11030-EP2301918A1
11030-EP2305219A1
11030-EP2305633A1
Benzenesulfonic Acid and its Impurities
An organosulfur compound , Benzenesulfonic acid is used for preparation of benzenesulfonate salts or bensilates from which various pharmaceutical drugs are preparaed.
Benzenesulfonic acid is prepared by sulfonation of benzene ring.
Reference standards of Benzenesulfonic Acid API, and its pharmacopeial, non pharmacopeial impurities, and stable isotopes are listed below.
Flash Point: >100°C
Melting Point: 45.0°C to 50.0°C
Color: Yellow to Brown
Infrared Spectrum: Authentic
Packaging: Glass bottle
CAS Min %: 88.0
CAS Max %: 100.0
Assay Percent Range: 90%
Linear Formula: C6H5SO3H
General tips
For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.
Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day.
However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃.
In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
11030-EP2305641A1
11030-EP2305646A1
11030-EP2305647A1
11030-EP2305649A1
11030-EP2305651A1
11030-EP2305659A1
11030-EP2305672A1
11030-EP2305673A1
11030-EP2305685A1
11030-EP2305686A1
11030-EP2308839A1
11030-EP2308854A1
11030-EP2308857A1
11030-EP2308869A1
11030-EP2311801A1
11030-EP2311802A1
11030-EP2311803A1
11030-EP2311804A2
11030-EP2311807A1
11030-EP2311809A1
11030-EP2311810A1
BENZENESULPHONIC ACID
These corrosion data are mainly based on results of general corrosion laboratory tests, carried out with pure chemicals and water solutions nearly saturated with air (the corrosion rate can be quite different if the solution is free from oxygen).
All concentrations are given in weight-% and the solvent is water if nothing else is shown.
The corrosion data apply to annealed materials with normal microstructure and clean surfaces, throughout.
Use Summary: Alkyl (C8’C24) benzenesulfonic acid and its ammonium, calcium, magnesium, potassium, sodium, and zinc salts are surfactants with a wide variety of manufacturing uses.
As inert ingredients, alkyl (C8-C24) benzenesulfonic acid and its ammonium, calcium, magnesium, potassium, sodium, and zinc salts are used as surfactants and related adjuvants of surfactants in pesticide formulations applied to growing crops and raw agricultural commodities, and as surfactants and emulsifiers in pesticide formulations applied to animals.
Chemical NameBenzenesulfonic Acid-13C6
Synonyms17-120A-13C6; BSA-13C6; Benzenemonosulfonic Acid-13C6; Benzenesulfonic Acid-13C6 (surfactant); Besylic Acid-13C6; Phenylsulfonic Acid-13C6
Alternate CAS #Unlabelled: 98-11-3; Unlabelled Monohydrate: 2615
Molecular Formula¹³C₆H₆O₃S
Molecular Weight164.13
CategoryBuilding Blocks; Isotopic Labeled Analogues;
ApplicationsBenzenesulfonic Acid-13C6 is the isotope labelled analog of Benzenesulfonic Acid (B189700, Monohydrate); a compound used in the synthesis of HER2/EFGR dual inhibitors in the treatment of cancers and displaying potency towards anti-tumor activity.
11030-EP2311818A1
11030-EP2311842A2
11030-EP2314575A1
11030-EP2316457A1
11030-EP2316458A1
11030-EP2316459A1
11030-EP2316825A1
11030-EP2316826A1
11030-EP2316827A1
11030-EP2316828A1
11030-EP2316831A1
11030-EP2371814A1
74485-EP2284160A1
74485-EP2305647A1
74485-EP2308857A1
74485-EP2377847A1
98736-EP2270002A1
98736-EP2295433A2
98736-EP2301928A1
98736-EP2301940A1
Q421494
SR-01000944759
J-519685
SR-01000944759-1
Phenylsulfonic acid;Besylic acid;Kyselina benzensulfonova
Benzenesulfonic acid, PharmaGrade, manufactured under appropriate GMP controls for pharma or biopharmaceutical production
Undecylbenzenesulphonic acid
4-UNDECYLBENZENESULFONIC ACID
Benzenesulfonic acid, undecyl-
Alkyl(C11)benzenesulfonic acid
n-undecylbenzenesulfonic acid
UNDECYLBENZENESULFONIC ACID
p-Undecylbenzenesulfonic acid
4-undecylbenzene-1-sulfonic acid
39156-49-5
EINECS 256-805-4
undecyl-benzenesulfonic acid
4-undecylbenzenesulphonic acid
4-Undecyl-Benzenesulfonic acid
SCHEMBL4534627
Benzenesulfonic acid, 4-undecyl-
CHEBI:141538