SULFAMIC ACID

CAS No.: 5329-14-6
EC No.: 226-218-8

Synonyms:
SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; SULFAMIC ACID; 5329-14-6; Amidosulfonic acid; Aminosulfonic acid; Sulphamic acid; Amidosulfuric acid; Imidosulfonic acid; Sulfamidic acid; Sulfaminic acid; Jumbo; Sulphamidic acid; Aminosulfuric acid; Kyselina sulfaminova; Kyselina amidosulfonova; Caswell No. 809; sulfuramidic acid; NSC 1871; MFCD00011603; Kyselina sulfaminova [Czech]; UNII-9NFU33906Q; HSDB 795; Kyselina amidosulfonova [Czech]; amidohydroxidodioxidosulfur; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; EINECS 226-218-8; H2NSO3H; UN2967; EPA Pesticide Chemical Code 078101; CHEMBL68253; AI3-15024; CHEBI:9330; [S(NH2)O2(OH)]; 9NFU33906Q; Sulfamic acid [UN2967] [Corrosive]; Sulfamic acid, 99%; DSSTox_CID_14005; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; DSSTox_RID_79107; DSSTox_GSID_34005; CAS-5329-14-6; SULFAMIC ACID, ACS; 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Amidosulfonicacid; Aminosulfuric acid; Imidosulfonic acid; Kyselina amidosulfonova [Czech]; Kyselina sulfaminova [Czech]; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; SO2 [Formula]; Sulfamic acid [UN2967] [Corrosive]; Sulfamic acid, acs; Sulfamic acid, ACS grade; Sulfamic acid, reag; Sulfamidsaeure; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; Sulfaminic acid; SULFITE ION; sulfuramidic acid; SULPHAMIC ACID; Sulphamic-acid-; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; Sulphamidic acid; UN 2967; WLN: ZSWQ; 氨基磺酸 [Chinese]; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; SULFAMIC ACID; 5329-14-6; Amidosulfonic acid; Aminosulfonic acid; Sulphamic acid; Amidosulfuric acid; Imidosulfonic acid; Sulfamidic acid; Sulfaminic acid; Jumbo; Sulphamidic acid; Aminosulfuric acid; Kyselina sulfaminova; Kyselina amidosulfonova; Caswell No. 809; sulfuramidic acid; NSC 1871; MFCD00011603; Kyselina sulfaminova [Czech]; UNII-9NFU33906Q; HSDB 795; Kyselina amidosulfonova [Czech]; amidohydroxidodioxidosulfur; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; EINECS 226-218-8; H2NSO3H; UN2967; EPA Pesticide Chemical Code 078101; CHEMBL68253; AI3-15024; CHEBI:9330; [S(NH2)O2(OH)]; 9NFU33906Q; Sulfamic acid [UN2967] [Corrosive]; Sulfamic acid, 99%; DSSTox_CID_14005; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; DSSTox_RID_79107; DSSTox_GSID_34005; CAS-5329-14-6; SULFAMIC ACID, ACS; SULFAMIC ACID, REAG; sulfoamine; Sulfamidsaeure; Sulphamic-acid-; Amidoschwefelsaeure; amidosulphuric acid; sulfamic acid group; WLN: ZSWQ; sulfuric acid amide group; NH2SO3H; Sulfamic acid, ACS grade; ACMC-20a47z; NH3SO3; EC 226-218-8; NCIOpen2_000675; KSC269M4H; ARONIS25155; Molybdenum, Quant Test Strips; DTXSID6034005; BDBM26994; CTK1G9643; NSC1871; Sulfamic acid, p.a., 99.5%; Sulfamic acid, analytical standard; [N]S(O)(=O)=O; NS([O])(=O)=O; KS-000000UE; NSC-1871; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; Sulfamic acid, reagent grade, 98%; Tox21_201905; Tox21_303482; 8894AF; ANW-56397; STL282725; 7773-06-0 (mono-ammonium salt); AKOS005287325; Sulfamic acid, ACS reagent, 99.3%; ZINC238809066; MCULE-8047713803; UN 2967; KS-0000472G; NCGC00090927-01; NCGC00090927-02; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; NCGC00257489-01; NCGC00259454-01; Sulfamic acid [UN2967] [Corrosive]; Sulfamic acid, ReagentPlus(R), >=99%; Sulfamic acid, >=99.5% (alkalimetric); SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; LS-147664; FT-0688102; Sulfamic acid, 99.999% trace metals basis; Sulfamic acid, SAJ first grade, >=99.0%; Sulfamic acid, JIS special grade, >=99.5%; Q412304; W-105754; Sulfamic acid, analytical standard (for acidimetry), ACS reagent; 226-218-8 [EINECS]; 5329-14-6 [RN]; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; Acide sulfamique [French] [ACD/IUPAC Name]; amidosulfonic acid; Amidosulfuric acid; aminosulfonic acid; Imidosulfuric acid [ACD/Index Name]; Kyselina amidosulfonova [Czech]; Kyselina sulfaminova [Czech]; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; MFCD00011603 [MDL number]; Sulfamic acid [ACD/Index Name] [ACD/IUPAC Name]; sulfamidic acid; Sulfamidsäure [German] [ACD/IUPAC Name]; [5329-14-6]; 7773-06-0 (Mono-ammonium salt); 99.99% (metals basis); amidohydroxidodioxidosulfur; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; Amidoschwefelsaeure; Amidosulfonicacid; Aminosulfuric acid; Imidosulfonic acid; Kyselina amidosulfonova [Czech]; Kyselina sulfaminova [Czech]; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; SO2 [Formula]; Sulfamic acid [UN2967] [Corrosive]; Sulfamic acid, acs; Sulfamic acid, ACS grade; Sulfamic acid, reag; Sulfamidsaeure; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; Sulfaminic acid; SULFITE ION; sulfuramidic acid; SULPHAMIC ACID; Sulphamic-acid-; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit; Sulphamidic acid; UN 2967; WLN: ZSWQ; 氨基磺酸 [Chinese]; SULFAMIC ACID; sulfamic acid; SÜLFAMİK ASİT; sülfamik asit

SULFAMIC ACID

Sulfamic acid
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Sulfamic acid
Tautomerism of sulfamic acid
Ball-and-stick model of the canonical neutral form
Ball-and-stick model of the zwitterionic form
Sample of sulfamic acid.jpg
Names
IUPAC name
Sulfamic acid
Identifiers
CAS Number    
5329-14-6 check
3D model (JSmol)    
Interactive image
zwitterion: Interactive image
ChEBI    
CHEBI:9330 check
ChEMBL    
ChEMBL68253 check
ChemSpider    
5767 check
ECHA InfoCard    100.023.835 Edit this at Wikidata
EC Number    
226-218-8
PubChem CID    
5987
RTECS number    
WO5950000
UNII    
9NFU33906Q check
UN number    2967
CompTox Dashboard (EPA)    
DTXSID6034005 Edit this at Wikidata
InChI[show]
SMILES[show]
Properties
Chemical formula    H3NSO3
Molar mass    97.10 g/mol
Appearance    white crystals
Density    2.15 g/cm3
Melting point    205 °C (401 °F; 478 K) decomposes
Solubility in water    Moderate, with slow hydrolysis
Solubility    
Moderately soluble in DMF
Slightly soluble in MeOH
Insoluble in hydrocarbons
Acidity (pKa)    1.0[1]
Hazards
Safety data sheet    ICSC 0328
EU classification (DSD) (outdated)    Irritant (Xi)
R-phrases (outdated)    R36/38 R52/53
S-phrases (outdated)    (S2) S26 S28 S61
Related compounds
Other cations    Ammonium sulfamate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Sulfamic acid, also known as amidosulfonic acid, amidosulfuric acid, aminosulfonic acid, and sulfamidic acid, is a molecular compound with the formula H3NSO3. This colourless, water-soluble compound finds many applications. Sulfamic acid melts at 205 °C before decomposing at higher temperatures to water, sulfur trioxide, sulfur dioxide and nitrogen.[2]

Sulfamic acid (H3NSO3) 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. Sulfamates are derivatives of sulfamic acid.

Contents
1    Production
2    Structure and reactivity
2.1    Acid–base reactions
2.2    Reaction with nitric and nitrous acids
2.3    Reaction with hypochlorite
2.4    Reaction with alcohol
3    Applications
3.1    Cleaning agent
3.2    Other uses
3.3    Silver polishing
4    References
5    Further reading
Production
Sulfamic acid is produced industrially by treating urea with a mixture of sulfur trioxide and sulfuric acid (or oleum). The conversion is conducted in two stages:

OC(NH2)2 + SO3 → OC(NH2)(NHSO3H)
OC(NH2)(NHSO3H) + H2SO4 → CO2 + 2 H3NSO3
In this way, approximately 96,000 tonnes were produced in 1995.[3]

Structure and reactivity

Ball-and-stick model of a sulfamic acid zwitterion as it occurs in the crystal state.[4]
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 sulfamic acid is well described by a zwitterionic form.

Aqueous solutions of sulfamic acid are unstable and slowly hydrolyse to ammonium bisulfate, but the crystalline solid is indefinitely stable under ordinary storage conditions. Its behaviour resembles that of urea, (H2N)2CO. Both feature amino groups linked to electron-withdrawing centres that can participate in delocalised bonding. Both liberate ammonia upon heating in water ; however, the sulfamic acid reverts back to sulfuric acid , in place of the CO2 that urea would release , according to the following reaction :

H3NSO3 + H2O → H2SO4 + NH3
Acid–base reactions
Sulfamic 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).

H3NSO3 + NaOH → NaH2NSO3 + H2O
Double deprotonation can be effected in ammonia solution to give the anion HNSO2−
3.[6]

H3NSO3 + 2 NH3 → HNSO2−
3 + 2 NH+
4
Reaction with nitric and nitrous acids
With nitrous acid, sulfamic acid reacts to give nitrogen:

HNO2 + H3NSO3 → H2SO4 + N2 + H2O
while with nitric acid, it affords nitrous oxide:[7]

HNO3 + H3NSO3 → H2SO4 + N2O + H2O
Reaction with hypochlorite
The reaction of excess hypochlorite ions with sulfamic acid or a sulfamate salt gives rise reversibly to both N-chlorosulfamate and N,N-dichlorosulfamate ions.[8][9][10]

HClO + H2NSO3H → ClNHSO3H + H2O
HClO + ClNHSO3H ⇌ Cl2NSO3H + H2O
Consequently, sulfamic acid is used as hypochlorite scavenger in the oxidation of aldehydes with chlorite such as the Pinnick oxidation.

Reaction with alcohol
Upon heating sulfamic acid will react with alcohols to form the corresponding organosulfates. It is more expensive than other reagents for doing this, such as chlorosulfonic acid or oleum, but is also significantly milder and will not sulfonate aromatic rings. Products are produced as their ammonium salts. Such reactions can be catalyzed by the presence of urea.[10]

ROH + H2NSO3H → ROS(O)2O− + NH+
4
Without the presence of any catalysts , sulfamic acid will not react with ethanol at temperatures below 100 °C .

Applications
Sulfamic 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.

Sulfamates 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.[11]

Cleaning agent
Sulfamic acid is used as an acidic cleaning agent, sometimes pure or as a component of proprietary mixtures, typically for metals and ceramics. It is frequently used for removing rust and limescale, replacing the more volatile and irritating hydrochloric acid, which is cheaper. It is often a component of household descaling agents, for example, Lime-A-Way Thick Gel contains up to 8% sulfamic acid and has pH 2.0–2.2,[12] or detergents used for removal of limescale. When compared to most of the common strong mineral acids, sulfamic acid has desirable water descaling properties, low volatility, and low toxicity. It forms water-soluble salts of calcium and ferric iron.

Sulfamic acid is preferable to hydrochloric acid in household use, due to its intrinsic safety. If erroneously mixed with hypochlorite based products such as bleach, it 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.

It also finds applications in the industrial cleaning of dairy and brewhouse equipment. Although it is considered less corrosive than hydrochloric acid, corrosion inhibitors are often added to the commercial cleansers of which it is a component. It can be used for descaling home coffee and espresso machines and in denture cleaners.

Other uses
Catalyst for esterification process
Dye and pigment manufacturing
Herbicide
Coagulator for urea-formaldehyde resins
Ingredient in fire extinguishing media. Sulfamic 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.
Silver polishing
According to the label on the consumer product, the liquid silver cleaning product TarnX contains thiourea, a detergent, and sulfamic acid.

Description
General description
Sulfamic acid (H2NSO3H) is widely used inorganic compound. It exists in zwitterionic form and neutral forms. Zwitterionic form has been reported to be is more stable than neutral form. Its industrial applications have been reported.[11] It has various organic synthesis applications.[1]

Sulfamic acid is a strong inorganic acid. It is a hypochlorite scavenger.[6] The ability of sulfamic acid to reduce nitrate to nitrogen gas under acidic condition has been utilized to denitrify nitrate-rich wastewater along with zinc powder.[2]

Application
Sulfamic acid (H2NSO3H) may be used in the following studies:
• As catalyst in the synthesis of aryl-14H-dibenzo[a.j]xanthenes.[12]
• As green catalyst for the preparation of amide from ketoxime.[13]
• As ammonia equivalent in the regioselective synthesis of primary allylic amines, via allylic substitution reactions.[1]
• Synthesis of polysubstituted quinolones.[14]
Sulfamic acid may be used in the following processes:
• As a titrant in the determination of the burette injection volume and chemical calibration factor.[3]
• To neutralize excess nitrous acid in the colorimetric paracetamol assay by modified Glynn and Kendal colorimetric method.[4]
• To prevent endogenous mercury (Hg) loss during the urine Hg measurement by inductively coupled plasma mass spectrometry (ICP-MS) method.[5]
• As an acid catalyst and a hypochlorite scavenger in the chlorite oxidation of dialdehyde cellulose (DAC).[6]
• As a heterogeneous catalyst in the synthesis of polyhydroquinoline derivatives by Hantzsch condensation reaction.[7]
• As catalyst in the degradation of bamboo fiber to 5-hydroxymethylfurfural (HMF).[8]
• As an acid reagent in the determination of silicates in water samples based on centrifugal microfluidics.[9]
• As catalyst in the synthesis of deazaoxaflavin at room temperature.[10]

2.06.3.9 Sulfamic Acid and Derivatives Thereof: R1NHSO3R2, R12NSO3R2
The general synthetic methods used for the preparation of sulfamic acids were reviewed in COFGT (1995) <1995COFGT(2)333>.

2.06.3.9.1 Sulfamic acids: R12NSO3H
Ring opening of cyclic sulfamidates by acylamines or thiols results in the formation of sulfamic acid salts (Equation (39)) <2003OL811>. This process has been used in a synthesis of thiomorpholine and piperazine derivatives. Antibacterial agents <2000T5571> and oligosaccharide derivatives <2003OBC2253> are among recently described biologically active compounds containing sulfamic acids.

Bicyclic sulfamate 83 readily reacts with lithium diphenylphosphide to generate sulfamic acid 84 in excellent yields (Scheme 8). Hydrolysis of this reaction intermediate under oxygen free conditions eventually leads to the formation phosphine ligand 85.120 Compound 83 undergoes a similar reaction in the presence of lithiated benzene derivatives. Acidic hydrolysis of sulfamic acid intermediates at high temperature furnishes substituted 2-benzyl pyrrolidines 87 in a stereocontrolled fashion (Scheme 8).44 Ring-opening of bicyclic sulfamates can also be achieved by treatment with the sodium salt of 2-chloro-5-hydroxypyridine to form racemic pyridyl ethers.43

N-sulfoglucosamine (CHEBI:21794) has functional parent sulfamic acid (CHEBI:9330)
N-sulfotyrosine (CHEBI:90373) has functional parent sulfamic acid (CHEBI:9330)
cyclohexylsulfamic acid (CHEBI:15964) has functional parent sulfamic acid (CHEBI:9330)
phaseolotoxin (CHEBI:8047) has functional parent sulfamic acid (CHEBI:9330)
sulfamate ester (CHEBI:48199) has functional parent sulfamic acid (CHEBI:9330)
sulfamoyl group (CHEBI:48266) is substituent group from sulfamic acid (CHEBI:9330)