Sulfamic acid

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Sulfamic acid

Sulfamic acid, also known as amidosulfonic acid, amidosulfuric acid, aminosulfonic acid, and sulfamidic acid, is a molecular compound with the formula H₃NSO₃. This colorless, water-soluble compound finds many applications. although it can sometimes be in the form of a white crystalline solid.

Sulfamic acid (H₃NSO₃) may be considered an intermediate compound between sulfuric acid

Sulfuric acid

Sulfuric acid, hydrogen2sulfuroxygen4, is a strong mineral acid. It is soluble in water at all concentrations. Sulfuric acid has many applications, and is one of the top products of the chemical industry....
(H₂SO₄), and sulfamide

Sulfamide

Sulfamide is a chemical compound with the molecular structure H2NSO2NH2. Sulfamide is produced by the reaction of sulfuryl chloride with ammonia....
(H₄N₂SO₂), effectively - though see below - replacing an -OH group with an -NH₂ group at each step.

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Structure and reactivity

First, it should be noticed that the compound is well described by the formula H₃NSO₃, not the tautomer

Tautomer

Tautomers are isomers of organic compounds that readily interconvert by a chemical reaction called tautomerization. Commonly this reaction results in the formal migration of a hydrogen atom or proton, accompanied by a switch of a single bond and adjacent double bond....
H₂NSO₂(OH). The relevant bond distances are S=O, 1.44 and S-N 1.77 Å

Ångström

An ?ngstr?m or angstrom is an internationally recognized non-SI unit of length equal to 0.1 nanometre or 1 metres. It is sometimes used in expressing the sizes of atoms, lengths of chemical bonds and optical spectrum, and dimensions of parts of integrated circuits....
. The greater length of the S-N distance is consistent with a single bond. Furthermore, a neutron diffraction

Neutron diffraction

Neutron diffraction is a method for the determination of the atomic and/or magnetic structure of a material. It can be equally well applied to study crystalline solids , gasses, liquids or amorphous materials....
study located the hydrogen atoms, all three of which are 1.03 Å

Ångström

An ?ngstr?m or angstrom is an internationally recognized non-SI unit of length equal to 0.1 nanometre or 1 metres. It is sometimes used in expressing the sizes of atoms, lengths of chemical bonds and optical spectrum, and dimensions of parts of integrated circuits....
distant from nitrogen. The structures shown with this article are for the two main tautomer

Tautomer


Ball-and-stick model Ball-and-stick model Ball-and-stick models and space-filling models are three-dimensional space or spatial molecular models which serve to display the structure of chemical products and chemical substance or biomolecules.... of a sulfamic acid zwitterion in the crystal

Sulfamic acid is a moderately strong acid, K_a = 1.01 x 10⁻¹. Because the solid is non-hygroscopic, it is used as a standard in acidometry (quantitative assays of acid content). Double deprotonation can be effected in NH₃

Ammonia

Ammonia is a chemical compound with the chemical formula nitrogenhydrogen. It is normally encountered as a gas with a characteristic pungent odor....
solution to give [HNSO₃]²⁻.

Sulfamic acid melts at 205 °C before decomposing at higher temperatures to H₂O, SO₃, SO₂, and N₂.

Water solutions are unstable and slowly hydrolyze to ammonium bisulfate

Ammonium bisulfate

Ammonium bisulfate, also known as ammonium hydrogen sulfate, is a white, crystalline solid when it is completely pure, with chemical formula HSO4....
, but the crystalline solid is indefinitely stable under ordinary storage conditions.

With HNO₂

Nitrous acid

Nitrous acid is a weak and monobasic acid known only in solution and in the form of nitrite salts.Nitrous acid is used to make diazo from amines; this occurs by nucleophilic attack of the amine onto the nitrite, reprotonation by the surrounding solvent, and double-elimination of water....
, sulfamic acid reacts to give N₂

Nitrogen

Nitrogen is a chemical element that has the symbol N and atomic number 7 and atomic mass 14.00674?. Elemental nitrogen is a colorless, odorless, tasteless and mostly inert diatomic gas at standard conditions, constituting 78% by volume of Earth's atmosphere....
, while with HNO₃

Nitric acid

Nitric acid , also known as aqua fortis and spirit of nitre, is a highly corrosion and toxic strong acid that can cause severe burns....
, it affords N₂O

Nitrous oxide

Nitrous oxide, commonly known as "laughing gas", is a chemical compound with the chemical formula Nitrogen2Oxygen. At room temperature, it is a colorless Flammability gas, with a pleasant, slightly sweet odor and taste....
.

The behavior of H₃NSO₃ resembles that of urea

Urea

Urea is an organic compound with the chemical formula 2carbonoxygen.Urea is also known by the International Nonproprietary Name carbamide, as established by the World Health Organization....
, (H₂N)₂CO, in some ways. Both feature amino groups linked to electron-withdrawing centers that can participate in delocalized bonding. Both liberate ammonia

Ammonia

Ammonia is a chemical compound with the chemical formula nitrogenhydrogen. It is normally encountered as a gas with a characteristic pungent odor....
upon heating in water.

Applications

The most famous application of sulfamic acid is in the synthesis of compounds that taste sweet. Reaction with cyclohexylamine

Cyclohexylamine

Cyclohexylamine, also called hexahydroaniline, 1-aminocyclohexane, or aminohexahydrobenzene, is an organic chemical, an amine derived from cyclohexane....
followed by addition of NaOH

Sodium hydroxide

Sodium hydroxide , also known as lye, caustic soda and sodium hydrate, is a caustic metallic Base . Sodium hydroxide forms a strong alkaline solution when dissolved in a solvent such as water, however, only the hydroxide ion is basic....
gives C₆H₁₁NHSO₃Na, sodium cyclamate. Related compounds are also sweetener

Sweetener

A sweetener is a food additive which adds the basic taste of sweetness to a food; artificial sweeteners are sugar substitutes....
s, see acesulfame potassium

Acesulfame potassium

Acesulfame potassium is a calorie-free artificial sweetener, also known as Acesulfame K or Ace K , and marketed under the trade names Sunett and Sweet One....
.

Sulfamates (O-substituted-, N-substituted-, or di-/tri-substituted derivatives of sulfamic acid) have been used in the design of many types of therapeutic agents such as antibiotic

Antibiotic

In common usage, an antibiotic is a substance or compound that kills or inhibits the growth of bacteria. Antibiotics belong to the group of antimicrobial compounds used to treat infections caused by microorganisms, including fungus and protozoa....
s, nucleoside/nucleotide human immunodeficiency virus (HIV) reverse transcriptase inhibitor

Reverse transcriptase inhibitor

Reverse transcriptase inhibitors are a class of antiretroviral drug used to treat HIV infection, tumors, and cancer. RTIs inhibit activity of reverse transcriptase, a viral DNA polymerase enzyme that retroviruses need to reproduce....
s, HIV protease inhibitors (PIs), anti-cancer drugs (steroid sulfatase

Steroid sulfatase

Steroid sulfatase is an sulfatase enzyme involved in the metabolism of steroids. It is encoded by the STS gene....
and carbonic anhydrase

Carbonic anhydrase

The carbonic anhydrases form a family of enzymes that catalyst the rapid conversion of carbon dioxide to bicarbonate and Hydronium ions, a reaction that occurs rather slowly in the absence of a catalyst....
inhibitors), anti-epileptic

Epilepsy

Epilepsy is a common chronic neurological disorder characterized by recurrent unprovoked seizure s. These seizures are transient signs and/or symptoms of abnormal, excessive or synchronous neuronal activity in the brain....
drugs, and weight loss drugs.

Sulfamic acid is used as an acidic cleaning agent, typically for metal

Metal

In chemistry, a metal is a chemical element whose atoms readily lose electrons to form positive ions , and form metallic bonds between other metal atoms and ionic bonds between nonmetal atoms....
s and ceramic

Ceramic

File:Bridge from dental porcelain.jpgFile:Qing vase p1070256.jpgA ceramic is an inorganic, nonmetal solid prepared by the action of heat and subsequent cooling....
s. It is a replacement for hydrochloric acid

Hydrochloric acid

Hydrochloric acid is the solution of hydrogen chloride in water. It is a highly corrosive, strong acid mineral acid and has major industrial uses....
for the removal of rust

Rust

Rust is a general term for a series of iron oxides, usually red oxides, formed by the reaction of iron and oxygen in the presence of water or air moisture....
. In households, it is often found as a descaling agent

Descaling agent

An anti-scaling agent is also known as descaling agent, anti-limestone, anti-limescale, anti-lime or anti-scale. This is chemicals for preventing or removing build up of fouling or scales....
in detergent

Detergent

A detergent is a material intended to assist cleaning. The term is sometimes used to differentiate between soap and other surfactants used for cleaning....
s used for removal of limescale

Limescale

Limescale is the hard, off-white, chalky deposit found in kettles, hot-water boilers and the inside of inadequately maintained hot-water central heating systems....
. From all acid, Sulfamic acid has the best water descaling property, thus also its application in cleaning dairy farm equipment and beer brewery. Although it is considered less corrosive than hydrochloric acid

Hydrochloric acid

Hydrochloric acid is the solution of hydrogen chloride in water. It is a highly corrosive, strong acid mineral acid and has major industrial uses....
, in its application as acid cleaning, it is very common to find user adding corrosion inhibitor.

Sulfamic acid is used in the S.C. Johnson & Sons, Inc. "Scrubbing Bubbles Fizz-Its Toilet Tablets."

Catalyst for esterification
Esterification

Esterification is the general name for a chemical reaction in which two reactants form an ester as the product . Esters are common in organic chemistry and biological materials, and often have a characteristic pleasant, fruity odor....
process
Dye
Dye

A dye can generally be described as a colored substance that has an Chemical affinity to the Wiktionary:substrate to which it is being applied....
and pigment
Pigment

A pigment is a material that changes the color of light it Reflection as the result of selective color absorption. This physical process differs from fluorescence, phosphorescence, and other forms of luminescence, in which the material itself emits light....
manufacturing
Herbicide
Herbicide

A herbicide is used to kill unwanted plants. Selective herbicides kill specific targets while leaving the desired crop relatively unharmed. Some of these act by interfering with the growth of the weed and are often synthetic "imitations" of plant hormones....
Ingredient in Denture Tablets
Coagulator for urea-formaldehyde resins
Ingredient in fire extinguishing media
Fire retardant

A fire retardant is a substance that helps delay or prevent combustion. Fire retardants are commonly used in fire fighting. Water is the most commonly used fire retardant, but the phrase typically refers to chemical retardants, including fire-fighting foams and fire-retardant gels....
. Sulfamic acid is the main raw material for Ammonium sulfamate which is a widely used herbicide and fire retardant material for household product.
Pulp and paper industry as a chloride stabilizer
Synthesis of nitrous oxide
Nitrous oxide

Nitrous oxide, commonly known as "laughing gas", is a chemical compound with the chemical formula Nitrogen2Oxygen. At room temperature, it is a colorless Flammability gas, with a pleasant, slightly sweet odor and taste....
by reaction with nitric acid
In household cleaning chemical products such as Cameo.

Sulfamic acid

Structure and reactivity

Applications

External links