BENZENESULFONIC ACID – piaggiotopcom

EC / List no.: 202-638-7 CAS no.: 98-11-3 Mol. formula: C6H6O3S

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Benzenesulfonic acid (conjugate base benzenesulfonate) is an organosulfur compound with the formula C6H6O3S. Benzenesulfonic acidis the simplest aromatic sulfonic acid. Benzenesulfonic acidforms 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 acidis often stored in the form of alkali metal salts. Its aqueous solution is strongly acidic.

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”.

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 acidis 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.

Uses 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, it is also used as a polymer remover stripping agent.

This substance is used in the following products: pH regulators and water treatment products. Other release to the environment of this substance is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.

Release to the environment of this substance can occur from industrial use: as processing aid, as an intermediate step in further manufacturing of another substance (use of intermediates), for thermoplastic manufacture and in the production of articles.

Benzene sulfonic acid is an organo sulfur compound with the formula C6H5SO3H. Benzenesulfonic acidis the simplest aromatic sulfonic acid. Benzenesulfonic acidforms 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 acidis often stored in the form of alkali metal salts. Its aqueous solution is strongly acidic.

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 acidis a strong acid, being dissociated in water.

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). Benzenesulfonic acidis an IRRITANT to the skin and eyes.

Application 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 acidcan also act as a dopant for the polymerization of pyrrole to form poly(pyrrole), a conducting polymer useful in the development of flexible capacitors.

Household & Commercial/Institutional Products • Commercial / Institutional

Uses Pharmaceutical related Related to electrical work (such as wiring of a building), electric current insulation materials, or other electrical components Related to metals – manufacturing of metals, casting of metals, production of metals, surface treatment of metals, etc Substances used for preventing, destroying or mitigating pests Related to photography, film, photographic equipment, photographic laboraties, photochemicals, and developing of photographs Accelerators, activators, oxidation agents, reducing agents, etc

Industry Processing Sectors Computer and electronic product manufacturing Fabricated metal product manufacturing

Benzenesulfonic acid (conjugate base benzenesulfonate) is the simplest aromatic sulfonic acid, that is soluble in water and ethanol, slightly soluble in benzene and insoluble in nonpolar solvents like diethyl ether. Benzenesulfonic acid was first obtained, together with diphenyl sulfone, by E. MITSCHERLICH 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. WURTZ and A. KEKUL_e in 1867 and by P. O. DEGENER in 1878. Until the early 1960s benzenesulfonic acid was used chiefly in the manufacture of phenol. Benzenesulfonic acid has the characteristic reactions of a strong aromatic sulfonic acid. Acid hydrolysis at 175 C splits it into benzene and sulfuric acid. 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 is used as an acid catalyst. The sodium salt is used to standardize dyes. A variety of pharmaceutical drugs are prepared as benzenesulfonate salts and are known as besilates (INN) or besylates (USAN).

Benzenesulfonic acid is obtained from sulphonation of benzene. For this, benzene is heated with concentrated Sulfuric acid.

Benzenesulfonic acidis a colorless crystal solid. Its melting point is 65°C. Its water-containing crystals have a melting point of 47°C. Benzenesulfonic acidis more soluble in water.

hemical Properties 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

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

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. Benzenesulfonic acidacts as an acid catalyst for direct esterification of amino acids and peptides.

Benzenesulfonic acid is the simplest member of the class of a benzenesulfonic acids that consists of a benzene carrying a single sulfo group. It is a conjugate acid of a benzenesulfonate.

Environmental Fate/Exposure Summary Benzenesulfonic acid’s use as a reagent in the manufacture of phenol, resorcinol, and other organic syntheses and as a catalyst could result in its release to the environment through various waste streams. Benzenesulfonic acid is expected to have very high mobility in soil. Volatilization of benzenesulfonic acid is not expected from either moist or dry soils. In water, benzenesulfonic acid is expected to be essentially non-volatile. Adsorption to sediment, bioconcentration, and hydrolysis are not expected to be important fate processes in aquatic systems. Biodegradation of benzenesulfonic acid is likely to occur in both aquatic and soil media provided adequate acclimation by microorganisms occurs. Benzenesulfonic acid will exist in both the vapor and particulate phases in the ambient atmosphere. If released to the atmosphere, it will degrade by reaction with photochemically produced hydroxyl radicals with an estimated half-life of approximately 29 days. Removal of benzenesulfonic acid from the atmosphere can occur through wet and dry deposition(SRC). Exposure to benzenesulfonic acid can occur through dermal contact, inhalation, and ingestion. (SRC)

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

In Vitro Use Guide Biodegradation had been quantified in an aqueous medium and P. fluorescens in agitated flasks experiments without sand matrix. The concentration of the MCs was determined every day (t=6 d for phenol, salicylic acid, and benzenesulfonic acid). Batch experiments were conducted in wide-neck bottles (Vinner = 250 ml) with defined moisture contents. The moisture content (θ) is the ratio between the volume of water and the total volume of the sample. To prevent unwanted strains from being included, the empty bottles were sterilized for t=20 min (T=121 °C) and the experiments were done on a sterile bench. The sterilized bottles were filled with 40 g of sterilized sand (t = 20 min, T = 121 °C) each. The substrate solution was prepared by adding c0 (MC) = 0.5 mmol/l and nutrient solution to V = 1 l of deionized water. Each MC was investigated individually. In addition, the calculated volume of P. fluorescens solution was added. Five different moisture contents were used (θ = 5, 10, 24, 37 and 42%) by adding Vsubstrate = 1.3 to 12 ml (c0 (MC) = 0.5 mmol/l), inorganic medium and P. fluorescens (OD600=0.1, 7 × 107 cells/ml). The bottles were closed with a rubber stopper to prevent ambient air from entering and they were shaken slightly in the dark to obtain a fairly homogeneous substrate distribution. The temperature was kept at T = 22 ±1 °C. The oxygen concentration was measured by sensor spots fixed to the inner glass surface of the bottles. After defined time periods (t=6 d or 60 d), 50 ml of deionized water (Millipore) were added with a dispenser and was shaken for t=1 min. The supernatant was filtered (pore size 0.4 μm, polycarbonate) and prepared for analysis. Each bottle was “sacrificed” and each supernatant was analyzed once. For example, a triplicate experiment with five different moisture contents and a maximum reaction time of three days with daily control needed 45 bottles (3 × 5 × 3).

This substance is used in the following products: pH regulators and water treatment products, pharmaceuticals and polymers. This substance is used for the manufacture of: chemicals. Release to the environment of this substance can occur from industrial use: as processing aid, as an intermediate step in further manufacturing of another substance (use of intermediates), for thermoplastic manufacture and in the production of articles.

Benzenesulfonic acid Preparation Benzenesulfonic acid is obtained from sulphonation of benzene. For this, benzene is heated with concentrated Sulfuric acid.

C6H6 + H2SO4(concentrated) → C6H5SO3H + H2O

Laboratory Method 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. It contains barium carbonate. Unused sulfuric acid precipitates as barium sulfate. Filter it and separate it. 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 It is a colorless crystal solid. Its melting point is 65°C. Its water-containing crystals have a melting point of 47°C. It is more soluble in water. Chemical Properties 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: It is an acid. Its aqueous solution is strongly acidic. The acid strength of its aqueous solution is as high as sulphuric acid. It 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 its sodium or potassium salts with solid NaOH or KOH.

C6H5SO3Na + NaOH → C6H5OH + Na2SO3

Displacement by amines group: Aniline is obtained by melting its sodium or potassium salts with NaNH2 or KNH2.

C6H5SO3Na + NaNH2 → C6H5NH2 + Na2SO3

Displacement by cyano group: Cyano benzene is obtained by melting its sodium or potassium salts with NaCN.

C6H5SO3Na + NaCN → C6H5CN + Na2SO3

Displacement by carboxyle group: Its 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 its 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, it is also a deactivating group. This implies that its 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. Nitration: When heated with a mixture of concentrated NHO3 and concentrated H2SO4, it forms m nitrobenzene sulphonic acid.

sulphonation: when heated at 200°C with gentle sulphuric acid, it forms meta benzene di sulphonic acid.

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

IUPAC NAMES benzene sulfonic acid BENZENESULFONIC ACID Benzenesulfonic acid benzenesulfonic acid Benzenesulfonic Acid Anhydrous Benzenesulphonic Acid Benzenesulphonic acid benzenesulphonic acid Benzenesulphonic acid benzenesulphonic acid benzenesulphonic-acid Benzolsulfonsäure

SYNONYMS: 17-120a BL70 BENZENESULFONIC ACID 90% TECHNICAL GRADE BENZENE SULFONIC ACID TECHNICAL GRADE BENZOLSULFONSAEURE BENZENESULFONIC ACID SOLUTION 70% IN WA BENZENESULFONIC ACID, TECH., 90% BENZENESULFONIC ACID SOLUTION 30-35% BENZENESULFONIC ACID, 98+% BENZENESULFONIC ACID,PRACTICAL GRADE 90-95% BENZENESULFONIC ACID, MM(CRM STANDARD) BenzenesulfonicAcid99% Benzenesulphonicacid,94% Benzenesulfonic acid, 90%, tech. 1-Benzenesulfonic acid Benzolsulfonsure BENZENESULFONIC ACID: TECH., CA 75% W/W AQUEOUS SOLUTION Benzenesulfonic acid, tech. ca 75% w/w aq. soln. Benzenesulfonic Acid Anhydrous Benzenesulfonic acid, sesquihydrate,99% Benzenesulphonic acid 94% Benzenesulfonic acid, tech., 90% 1KG Benzenesulfonic acid, tech., 90% 5GR acidebenzenesulfonique Benzenemonosulfonic acid benzenemonosulfonicacid Benzenesulfonicacid(40%solu Besylic acid besylicacid Kyselina benzensulfonova kyselinabenzensulfonova BENZENESULPHONIC ACID BENZENESULFONIC ACID BENZENESULFONIC ACID FOR SYNTHESIS Benzenesulfonic acid 98.0% (T) Benzenesulfonic acid, 95%, 95% 1998/11/3 Benzensulfonic acid Zidovudine impurity K Benzenesulfonic acid technical, >=90% (T) benzenesulfonicaci Benzenesulfonic acid ISO 9001:2015 REACH

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