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Sulfanilic acid (4-aminobenzenesulfonic acid) is an organic compound with the formula H3NC6H4SO3.
Sulfanilic acid is an off-white solid.
Sulfanilic acid is a zwitterion, which explains its high melting point.
Sulfanilic acid is a common building block in organic chemistry.
CAS Number: 121-57-3
EC Number: 204-482-5
IUPAC Name: 4-Aminobenzene-1-sulfonic acid
Chemical Formula: C6H7NO3S
Other names: 4-Aminobenzenesulfonic acid, 121-57-3, Sulphanilic acid, p-Aminobenzenesulfonic acid, Aniline-4-sulfonic acid, Sulfanilsaeure, Benzenesulfonic acid, 4-amino-, Aniline-p-sulfonic acid, Aniline-p-sulphonic acid, p-Aminophenylsulfonic acid, Kyselina sulfanilova, p-Anilinesulfonic acid, CHEBI:27500, NSC 7170, 4-aminobenzene-1-sulfonic acid, SUFANILIC ACID, UNII-434Z8C2635, P-SULFANILIC ACID, MFCD00007886, ANILINE P-SULFONIC ACID, CHEMBL1566888, 4-AMINOBENZENESULPHONIC ACID, Benzenesulfonic acid, 4-amino-, homopolymer, 434Z8C2635, Sulfanilic acid, ACS reagent, Amidosulfonic acid, Aminosulfonic acid, Sulphamic acid, Amidosulfuric acid, Imidosulfonic acid, Sulfamidic acid, Sulfaminic acid, Jumbo, Sulphamidic acid, Aminosulfuric acid, Kyselina sulfaminova, Kyselina amidosulfonova, sulfuramidic acid, NSC 1871, MFCD00011603, UNII-9NFU33906Q, amidohydroxidodioxidosulfur, H2NSO3H, CHEMBL68253, CHEBI:9330, [S(NH2)O2(OH)], 9NFU33906Q, Sulfanilic acid, 99%, DSSTox_CID_14005, DSSTox_RID_79107, DSSTox_GSID_34005, Caswell No. 809, Kyselina sulfaminova, CAS-5329-14-6, HSDB 795, Kyselina amidosulfonova, EINECS 226-218-8, UN2967, 4-amino benzenesulphonic acid, 4-Aminobenzenesulfonic acid, 4-aminobenzenesulfonic acid, 4-aminobenzenesulphonic acid, p-aminobenzenesulphonic acid, phanilic acid, Sulfanilic Acid, Sulfanilic acid, Sulfanilsäure, Sulphanilic acid, sulphanilic acid, Sulphanilic Acid, sulphanilic acid
Synthesis
Sulfanilic acid can be produced by sulfonation of aniline with concentrated sulfuric acid.
This proceeds via phenylsulfamic acid; a zwitterion with a N-S bond.
Eugen Bamberger originally proposed a mechanism involving a series of intramolecular rearrangements, with phenylsulfamic acid forming orthanilic acid, which rearranged to sulfanilic acid on heating.
Subsequent radiosulphur studies showed that the process is intermolecular, with the phenylsulfamic acid desulfating to generate sulfur trioxide, which then reacts with aniline at the para position in manner similar to a Bamberger rearrangement.
Sulfanilic acid appears as white powder with faint purple tinge.
Grayish-white flat crystals.
Low toxicity (used medicinally).
Sulfanilic acid is an aminobenzenesulfonic acid that is aniline sulfonated at the para-position.
Sulfanilic acid has a role as a xenobiotic metabolite, a xenobiotic, an environmental contaminant and an allergen.
Sulfanilic acid is a conjugate acid of a 4-aminobenzenesulfonate.
Sulfanilic acid is an organic compound with the formula H3NC6H4SO3.
Sulfanilic acid is an off-white solid.
Sulfanilic acid is a zwitterion, which explains its high melting point.
Sulfanilic acid is a common building block in organic chemistry.
As the compound readily forms diazo compounds, Sulfanilic acid is used to make dyes and sulfa drugs.
Sulfanilic acid is also used for the quantitative analysis of nitrate and nitrite ions by diazonium coupling reaction with N-(1-Naphthyl)ethylenediamine, resulting in an azo dye, and the concentration of nitrate or nitrite ions were deduced from the color intensity of the resulting red solution by colorimetry.
The diazonium salt of sulfanilic acid may be used in the preparation of azo dyes such as o-anisaldehyde, orange I and orange II.
Sulfanilic acid may also be used in the preparation of 2,6-dibromoaniline via bromination followed by desulfonation.
Reagent for the detection of histidine; intermediate for dyes and pharmaceuticalsSulfanilic acid is used as a reagent for chromatographic detection of histidine.
Sulfanilic acid is also used as a chemical intermediate in organic synthesis.
Sulfanilic acid is utilized in quantitative analysis of nitrate and nitrite ions.
Sulfanilic acid plays an essential role in the manufacturing of azo dyes and in synthesis of sulfa drugs.
Sulfanilic acid is used as a dopant for the chemical synthesis of polyaniline.
Sulfanilic acid is used to prepare 2,4-diamino-6-p-sulphoanilinopyrimidine by reacting with 6-chloro-pyrimidine-2,4-diamine.
Sulfanilic acid is a Tartrazine metabolite used for detection of nitrites.
Sulfanilic acid is used as Ehrlich's reagent for detection of nitrites.
Sulfanilic acid is also a metabolite of Tartrazine.
Sulfanilic acids chemical formula is C6H7NO3S, and this product is also known as p-aminobenzene sulphonic acid.
Sulphanilic Acid produced in Bondalti is a crystalline white solid, slightly water-soluble.
Sulphanilic Acid is industrially obtained from the hot reaction between aniline and sulphuric acid, subsequently purified, crystallised and, finally subject to drying and bagging.
Sulfanilic acid's supplied packaged in big-bags or in 25 kg bags.
From the modern uses of Sulphanilic Acid, the production of colourings for textile and food industry stands out, as well as optic whiteners for paper and detergents manufacture.
Sulfanilic acid is also at the basis of known sulphamides, important medications used from the early 20th century to treat streptococcal infections, having contributed to save countless lives.
Sulfanilic acid represents an important substance, which is frequently utilized in the industry of azo dyes as well as in drug development of antimicrobials (e.g. of sulfonamides).
Sulfanilic acid, of systematic name 4-aminobenzenesulfonic acid, is one of the most important organic compounds in chemistry and technology of azo dyes.
By reaction with an alkali nitrite in acid medium, sulfanilic acid provides diazonium salt that can easily couple as an electrophile with phenol in the alkaline medium or with aromatic amine in the acidic medium to form azo compounds.
Many of these substances are used in practice as synthetic azo dyes in textile and food industry.
The two well known dyes produced from sulfanilic acid are the acid-base indicator methyl orange and Orange II for textile colouring.
Sulfanilic acid is one of the most widely-used sulfonated aromatic amines in the production of azo dyes, dyeing auxiliaries, food coloring, pharmaceuticals perfumes and pesticides.
The resulting water contamination calls for the development of cost-effective treatment technologies.
Sulfanilic Acid Indicator Solution (Sulfanilic Acid Indicator Solution Solution or Solutions class is a product, and it is a adjusted solution used in laboratory and R&D studies, trials, experiments, etc.).
Sulfanilic acid is zwitterionic.
Sulfanilic acid is highly soluble in basic solutions, and moderately soluble in strongly acidic solutions.
Sulfanilic acids isoelectric point is 1.25, which would be the optimum pH for precipitating and recrystallizing it.
Sulfanilic acid crystallizes from water as a dihydrate, but can be dehydrated by heating.
Sulfanilic acid is a white solid when pure, but commercial and home made samples are usually off-white or even purple, due to contamination with trace amounts of strongly colored polyaniline compounds.
Sulfanilic acid (4-amino benzene sulfonic acid ) is an off-white crystalline solid which finds application in quantitative analysis of nitrate and nitrite ions.
Sulfanilic acid exists as a zwitterion, and has an unusually high melting point.
As the compound readily form diazo compounds, Sulfanilic acid is used to make dyes and sulpha drugs.
Sulfanilic acid is also used for the quantitative analysis of nitrate and nitrite ions by diazonium coupling reaction with N-(1-Naphthyl) ethylene diamine , resulting in an azo dye, and the concentration of nitrate or nitrite ions were deduced from the color intensity of the resulting red solution by colorimetry.
Sulfanilic acid is also used as a standard in combustion analysis.
The results of the research showed that the Sulfanilic acid derivatives can be used to formulate the wetting agent with properties comparable to the normal wetting agent.
Sulfanilic acid was modified by sulfation to yield Sulfanilic acid, which can be used as a wetting and dyeing agent and in cotton and linen finishings.
This review of the use of Sulfanilic acid in the chemical and polymer industries clearly demonstrates that Sulfanilic acid is a very valuable renewable resource.
Besides the direct use of this OH group functional Sulfanilic acid in many applications (e.g. for PU synthesis, a number of industrial procedures are well established to obtain a variety of different renewable platform chemicals).
In particular, the industrially available platform chemicals Sulfanilic acid and sebacic acid, in combination with the newly available α,o-bifunctional derivatives obtained via olefin metathesis, offer the potential to derive vast amounts of different polyesters and PAs with different application possibilities from Sulfanilic acid sustainable fashion.
Moreover, the various uses of Sulfanilic acid in polymer applications, described and highlighted in this additive, clearly demonstrate that Sulfanilic acid is and will be one of the most promising renewable raw materials for the chemical and polymer industries.
The production of wetting agent from Sulfanilic acid was carried out repeatedly.
Many desirable properties of Sulfanilic acid make it very useful in the wetting industry, so Sulfanilic acid can serve as a good substitute for synthetic wetting agent, traditional detergent bases.
Sulfanilic acid is also known as Sulphated Sulfanilic acid.
Sulfanilic acid is the only oil that will completely disperse in water.
Sulfanilic acid is expressed from the seed.
Sulfanilic acid is created by adding sulfuric acid to Sulfanilic acid and is considered the first synthetic detergent.
Sulfanilic acid has a distinctive and intense smell.
Sulfanilic acid is a surfactant and therefore makes a great base for Sulfanilic acid as it mixes well with water to form a milk bath.
Sulfanilic acid, also known as amidosulfonic acid, amidosulfuric acid, aminosulfonic acid, sulphamic acid and sulfamidic acid, is a molecular compound with the formula H3NSO3. This colourless, water-soluble compound finds many applications. Sulfanilic acid melts at 205 °C before decomposing at higher temperatures to water, sulfur trioxide, sulfur dioxide and nitrogen.[2]
The compound is well described by the formula H3NSO3, not the tautomer H2NSO2(OH). The relevant bond distances are 1.44 Å for the S=O and 1.77 Å for the S–N. The greater length of the S–N is consistent with a single bond.[5] Furthermore, a neutron diffraction study located the hydrogen atoms, all three of which are 1.03 Å distant from the nitrogen.[4] In the solid state, the molecule of Sulfanilic acid is well described by a zwitterionic form.
Aqueous solutions of Sulfanilic acid are unstable and slowly hydrolyse to ammonium bisulfate, but the crystalline solid is indefinitely stable under ordinary storage conditions.
Sulfanilic acids behaviour resembles that of urea, (H2N)2CO. Both feature amino groups linked to electron-withdrawing centres that can participate in delocalised bonding.
Sulfanilic acid is a moderately strong acid, Ka = 0.101 (pKa = 0.995).
Because the solid is not hygroscopic, it is used as a standard in acidimetry (quantitative assays of acid content).
Sulfanilic acid may be considered an intermediate compound between sulfuric acid (H2SO4), and sulfamide (H4N2SO2), effectively replacing a hydroxyl (–OH) group with an amine (–NH2) group at each step.
This pattern can extend no further in either direction without breaking down the sulfonyl (–SO2–) moiety.
Sulfanilic acids are derivatives of Sulfanilic acid.
Sulfanilic acid is mainly a precursor to sweet-tasting compounds.
Reaction with cyclohexylamine followed by addition of NaOH gives C6H11NHSO3Na, sodium cyclamate.
Related compounds are also sweeteners, such as acesulfame potassium.
Sulfanilic acids have been used in the design of many types of therapeutic agents such as antibiotics, nucleoside/nucleotide human immunodeficiency virus (HIV) reverse transcriptase inhibitors, HIV protease inhibitors (PIs), anticancer drugs (steroid sulfatase and carbonic anhydrase inhibitors), antiepileptic drugs, and weight loss drugs.
Sulfanilic acid is used as an acidic cleaning agent and descaling agent sometimes pure or as a component of proprietary mixtures, typically for metals and ceramics.
For cleaning purposes, there are different grades based on application such as GP Grade, SR Grade and TM Grade.
Sulfanilic acid is frequently used for removing rust and limescale, replacing the more volatile and irritating hydrochloric acid, which is cheaper.
Sulfanilic acid is often a component of household descalant, for example, Lime-A-Way Thick Gel contains up to 8% Sulfanilic acid and has pH 2.0–2.2, or detergents used for removal of limescale.
When compared to most of the common strong mineral acids, Sulfanilic acid has desirable water descaling properties, low volatility, and low toxicity.
Sulfanilic acid forms water-soluble salts of calcium and ferric iron.
Sulfanilic acid appears as a white crystalline solid.
Density 2.1 g / cm3.
Melting point 205°C. Combustible.
Irritates skin, eyes, and mucous membranes.
Low toxicity.
Used to make dyes and other chemicals.
Sulfanilic acid is the simplest of the Sulfanilic acids consisting of a single sulfur atom covalently bound by single bonds to hydroxy and amino groups and by double bonds to two oxygen atoms.
Sulfanilic acid is preferable to hydrochloric acid in household use, due to its intrinsic safety.
If erroneously mixed with hypochlorite based products such as bleach, Sulfanilic acid does not form chlorine gas, whereas the most common acids would; the reaction (neutralisation) with ammonia, produces a salt, as depicted in the section above.
Sulfanilic acid also finds applications in the industrial cleaning of dairy and brewhouse equipment.
Although Sulfanilic acid is considered less corrosive than hydrochloric acid, corrosion inhibitors are often added to the commercial cleansers of which Sulfanilic acid is a component.
Sulfanilic acid can be used as a descalant for descaling home coffee and espresso machines and in denture cleaners.
USES:
Used to make dyes and other organic chemicals
Also used as an analytical reagent (Ehrlich’s reagent and determination of nitrites) and antibacterial
Used in the paper
Pulp, board
polymer industries
Used as an additive to construction materials and foodstuffs
Catalyst for esterification process
Dye and pigment manufacturing
Herbicide
Descalant for scale removal
Coagulator for urea-formaldehyde resins
Ingredient in fire extinguishing media. Sulfanilic acid is the main raw material for ammonium sulfamate which is a widely used herbicide and fire retardant material for household products.
Pulp and paper industry as a chloride stabilizer
Synthesis of nitrous oxide by reaction with nitric acid
The deprotonated form (sulfamate) is a common counterion for nickel(II) in electroplating.
Used to separate nitrite ions from mixture of nitrite and nitrate ions( NO3−+ NO2−) during qualitative analysis of nitrate by Brown Ring test.
APPLICATIONS:
Food Colors like Sunset Yellow, Tartrazine,etc.D&C Yellow 6 Food Color，
Optical Brightener Agent
dyestuff intermediates like 1-(4-Sulphophenyl)-3-Carboxy-5-Pyrazolone，1-(4-Sulphophenyl)-3-Methyl-5-Pyrazolone.
