| Revision as of 12:33, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 473697840 of page Sulfamic_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 13:28, 13 December 2024 edit DMacks (talk | contribs)Edit filter managers, Autopatrolled, Administrators186,458 edits Moving from Category:Hydrogen compounds to Category:Oxoacids using Cat-a-lot |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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|Watchedfields = changed |
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| verifiedrevid = 417637524 |
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|verifiedrevid = 476994839 |
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|ImageFile = Zwitterion Structural Formulae V.1.svg |
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| Name = Sulfamic acid |
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|ImageName = Tautomerism of sulfamic acid |
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| ImageFile = Zwitterion Structural Formulae V.1.svg |
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|ImageFileL1 = Sulfamic_acid.png |
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| ImageSize = 220px |
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|ImageNameL1 = Ball-and-stick model of the canonical neutral form |
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| ImageName = Tautomerism of sulfamic acid |
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| ImageFileL1 = Sulfamic-acid-3D-balls.png |
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|ImageFileR1 = Sulfamic acid zwitterion stick ball.png |
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|ImageNameR1 = Ball-and-stick model of the zwitterionic form |
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| ImageSizeL1 = 110px |
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|ImageFile2 = Sample of sulfamic acid.jpg |
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| ImageNameL1 = Ball-and-stick model of the canonical neutral form |
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| ImageFileR1 = Sulfamic-acid-zwitterion-3D-balls.png |
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|IUPACName = Sulfamic acid |
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|Section1={{Chembox Identifiers |
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| ImageSizeR1 = 110px |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ImageNameR1 = Ball-and-stick model of the zwitterionic form |
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|ChemSpiderID = 5767 |
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| IUPACName = Sulfamic acid |
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|Gmelin = 25628 |
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| Section1 = {{Chembox Identifiers |
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|PubChem = 5987 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|InChI = 1/H3NO3S/c1-5(2,3)4/h(H3,1,2,3,4) |
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| ChemSpiderID = 5767 |
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|InChIKey = IIACRCGMVDHOTQ-UHFFFAOYAK |
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| PubChem = 5987 |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| InChI = 1/H3NO3S/c1-5(2,3)4/h(H3,1,2,3,4) |
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|ChEBI = 9330 |
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| InChIKey = IIACRCGMVDHOTQ-UHFFFAOYAK |
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|SMILES = O=S(=O)(O)N |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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|SMILES1 = O=(=O)() |
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| ChEBI = 9330 |
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|SMILES1_Comment = ] |
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| SMILES = O=S(=O)(O)N |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 68253 |
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|ChEMBL = 68253 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/H3NO3S/c1-5(2,3)4/h(H3,1,2,3,4) |
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|StdInChI = 1S/H3NO3S/c1-5(2,3)4/h(H3,1,2,3,4) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = IIACRCGMVDHOTQ-UHFFFAOYSA-N |
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|StdInChIKey = IIACRCGMVDHOTQ-UHFFFAOYSA-N |
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| CASNo = 5329-14-6 |
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|CASNo = 5329-14-6 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| UNNumber = 2967 |
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|UNII = 9NFU33906Q |
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| EINECS = 226-218-8 |
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|UNNumber = 2967 |
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| RTECS = WO5950000 |
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|EINECS = 226-218-8 |
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}} |
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|RTECS = WO5950000 |
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| Section2 = {{Chembox Properties |
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| Formula = H<sub>3</sub>NSO<sub>3</sub> |
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| MolarMass = 97.10 g/mol |
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| MeltingPt = 205 °C decomp. |
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| Density = 2.15 g/cm<sup>3</sup> |
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| Solubility = moderate, with slow hydrolysis |
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| pKa = 1.0<ref>{{cite doi|10.1039/JR9600004236}}</ref> |
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}} |
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| Section7 = {{Chembox Hazards |
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| ExternalMSDS = |
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| EUIndex = 016-026-00-0 |
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| EUClass = Irritant ('''Xi''') |
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| RPhrases = {{R36/38}} {{R52/53}} |
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| SPhrases = {{S2}} {{S26}} {{S28}} {{S61}} |
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| NFPA-H = |
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| NFPA-F = |
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| NFPA-R = |
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| NFPA-O = |
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| FlashPt = |
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}} |
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| Section8 = {{Chembox Related |
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| OtherAnions = |
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| OtherCations = ] |
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| OtherFunctn = |
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| Function = |
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| OtherCpds = |
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}} |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|Formula = H<sub>3</sub>NSO<sub>3</sub> |
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|MolarMass = 97.10 g/mol |
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|Appearance = white crystals |
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|MeltingPtC = 205 |
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|MeltingPt_notes = decomposes |
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|Density = 2.15 g/cm<sup>3</sup> |
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|Solubility = Moderate, with slow hydrolysis |
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|SolubleOther = {{unbulleted list|Moderately soluble in ]|Slightly soluble in ]|Insoluble in hydrocarbons}} |
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|pKa = 1.0<ref>{{Cite journal | last1 = Candlin | first1 = J. P. | last2 = Wilkins | first2 = R. G. | doi = 10.1039/JR9600004236 | title = 828. Sulphur–nitrogen compounds. Part I. The hydrolysis of sulphamate ion in perchloric acid |journal = Journal of the Chemical Society (Resumed) | pages = 4236–4241 | year = 1960 }}</ref> |
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}} |
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|Section3={{Chembox Hazards |
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|ExternalSDS = |
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|GHSPictograms = {{GHS07}} |
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|GHSSignalWord = Warning |
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|HPhrases = {{H-phrases|315|319|412}} |
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|PPhrases = {{P-phrases|264|273|280|302+352|305+351+338|321|332+313|337+313|362|501}} |
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}} |
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|Section4={{Chembox Related |
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|OtherCations = ] |
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}} |
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}} |
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'''Sulfamic acid''', also known as '''amidosulfonic acid''', '''amidosulfuric acid''', '''aminosulfonic acid''', '''sulphamic acid''' and '''sulfamidic acid''', is a molecular compound with the formula H<sub>3</sub>NSO<sub>3</sub>. This colourless, water-soluble compound finds many applications. Sulfamic acid melts at 205 °C before decomposing at higher temperatures to ], ], ] and ].<ref name ="kirk-othmer">{{Cite book | last1 = Yoshikubo | first1 = K. | last2 = Suzuki | first2 = M. | doi = 10.1002/0471238961.1921120625151908.a01 | chapter = Sulfamic Acid and Sulfamates | title = Kirk-Othmer Encyclopedia of Chemical Technology | year = 2000 | isbn = 0471238961 }}</ref> |
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Sulfamic acid (H<sub>3</sub>NSO<sub>3</sub>) may be considered an intermediate compound between ] (H<sub>2</sub>SO<sub>4</sub>), and ] (H<sub>4</sub>N<sub>2</sub>SO<sub>2</sub>), effectively replacing a ] (–OH) group with an ] (–NH<sub>2</sub>) group at each step. This pattern can extend no further in either direction without breaking down the ] (–SO<sub>2</sub>–) moiety. '''Sulfamates''' are derivatives of sulfamic acid. |
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==Production== |
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Sulfamic acid is produced industrially by treating ] with a mixture of ] and ] (or ]). The conversion is conducted in two stages, the first being ]: |
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:OC(NH<sub>2</sub>)<sub>2</sub> + SO<sub>3</sub> → OC(NH<sub>2</sub>)(NHSO<sub>3</sub>H) |
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:OC(NH<sub>2</sub>)(NHSO<sub>3</sub>H) + H<sub>2</sub>SO<sub>4</sub> → CO<sub>2</sub> + 2 H<sub>3</sub>NSO<sub>3</sub> |
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In this way, approximately 96,000 tonnes were produced in 1995.<ref>{{Ullmann|first=A.|last=Metzger|title=Sulfamic Acid|doi=10.1002/14356007.a25_439}}</ref> |
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==Structure and reactivity== |
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] of a sulfamic acid ] as it occurs in the crystal state.<ref name="Sass" />]] |
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The compound is well described by the formula H<sub>3</sub>NSO<sub>3</sub>, not the ] H<sub>2</sub>NSO<sub>2</sub>(OH). The relevant bond distances are 1.44 ] 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.<ref>{{Cite journal | last1 = Bats | first1 = J. W. | last2 = Coppens | first2 = P. | last3 = Koetzle | first3 = T. F. | title = The experimental charge density in sulfur-containing molecules. A study of the deformation electron density in sulfamic acid at 78 K by X-ray and neutron diffraction | doi = 10.1107/S0567740877002568 | journal = Acta Crystallographica Section B | volume = 33 | pages = 37–45 | year = 1977| issue = 1 | bibcode = 1977AcCrB..33...37B }}</ref> Furthermore, a ] study located the hydrogen atoms, all three of which are 1.03 ] distant from the nitrogen.<ref name="Sass">{{Cite journal | last1 = Sass | first1 = R. L. | title = A neutron diffraction study on the crystal structure of sulfamic acid | doi = 10.1107/S0365110X60000789 | journal = Acta Crystallographica | volume = 13 | issue = 4 | pages = 320–324 | year = 1960 | doi-access = free| bibcode = 1960AcCry..13..320S }}</ref> In the solid state, the molecule of sulfamic acid is well described by a ] form. |
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===Hydrolysis=== |
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The crystalline solid is indefinitely stable under ordinary storage conditions, however, aqueous solutions of sulfamic acid slowly hydrolyse to ], according to the following reaction: |
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:H<sub>3</sub>NSO<sub>3</sub> + H<sub>2</sub>O → <sup>+</sup><sup>−</sup> |
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Its behaviour resembles that of ], (H<sub>2</sub>N)<sub>2</sub>CO. Both feature ]s linked to electron-withdrawing centres that can participate in ]. Both liberate ] upon heating in water, with urea releasing CO<sub>2</sub> while sulfamic acid releases ]. |
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===Acid–base reactions=== |
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Sulfamic acid is a moderately strong acid, ''K''<sub>a</sub> = 0.101 (p''K''<sub>a</sub> = 0.995). Because the solid is not ], it is used as a standard in ] (quantitative assays of acid content). |
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:H<sub>3</sub>NSO<sub>3</sub> + NaOH → NaH<sub>2</sub>NSO<sub>3</sub> + H<sub>2</sub>O |
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Double deprotonation can be effected in liquid ] to give the anion {{chem|HNSO|3|2−}}.<ref name ="L.B. Clapp">{{Cite journal| last1 = Clapp | first1 = L. B. | title = Sulfamic acid and its uses | doi = 10.1021/ed020p189 | journal = Journal of Chemical Education | volume = 20 | issue = 4 | pages = 189–346 | year = 1943 | bibcode = 1943JChEd..20..189C}}</ref> |
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:H<sub>3</sub>NSO<sub>3</sub> + 2 NH<sub>3</sub> → {{chem|HNSO|3|2−}} + 2 {{chem|NH|4|+}} |
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===Reaction with nitric and nitrous acids=== |
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With ], sulfamic acid reacts to give ]: |
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:HNO<sub>2</sub> + H<sub>3</sub>NSO<sub>3</sub> → H<sub>2</sub>SO<sub>4</sub> + N<sub>2</sub> + H<sub>2</sub>O |
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while with concentrated ], it affords ]:<ref>{{cite journal |
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| last1 = Dzelzkalns |
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| first1 = Laila |
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| last2 = Bonner |
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| first2 = Francis |
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| title = Reaction between nitric and sulfamic acids in aqueous solution |
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| journal = Inorganic Chemistry |
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| volume = 17 |
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| issue = 12 |
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| pages = 3710–3711 |
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| doi = 10.1021/ic50190a080 |
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| date = 1978}}</ref> |
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:HNO<sub>3</sub> + H<sub>3</sub>NSO<sub>3</sub> → H<sub>2</sub>SO<sub>4</sub> + N<sub>2</sub>O + H<sub>2</sub>O |
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===Reaction with hypochlorite=== |
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The reaction of excess ] ions with sulfamic acid or a sulfamate salt gives rise reversibly to both ''N''-chlorosulfamate and ''N'',''N''-dichlorosulfamate ions.<ref>{{cite patent|country=US|number=3328294|title=Process for control of micro-organisms in process streams|pubdate=1967-06-27|assign=]|inventor1-last=Self|inventor1-first= Richard W.|inventor2-last=Watkins Jr. |inventor2-first=Joseph C.|inventor3-last=Sullins |inventor3-first=John K.}}</ref><ref>{{cite patent|country=FR|number=2087248|title=Systèmes aqueux stables contenant un composé N-hydrogéné et un hypohalogénite |pubdate=1971-12-31|assign=]|inventor1-last=|inventor1-first=}}</ref><ref name=1980rev>{{cite journal|last1=Benson|first1=G. Anthony|last2=Spillane|first2=William J.|title=Sulfamic acid and its ''N''-substituted derivatives|journal=Chemical Reviews|volume=80|issue=2|year=1980|pages=151–186|issn=0009-2665|doi=10.1021/cr60324a002}}</ref> |
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:HClO + H<sub>2</sub>NSO<sub>3</sub>H → ClNHSO<sub>3</sub>H + H<sub>2</sub>O |
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:HClO + ClNHSO<sub>3</sub>H {{eqm}} Cl<sub>2</sub>NSO<sub>3</sub>H + H<sub>2</sub>O |
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Consequently, sulfamic acid is used as hypochlorite ] in the oxidation of ] with ] such as the ]. |
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===Reaction with alcohols=== |
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Upon heating sulfamic acid will react with alcohols to form the corresponding ]s. It is more expensive than other reagents for doing this, such as ] or ], but is also significantly milder and will not sulfonate aromatic rings. Products are produced as their ] salts. Such reactions can be catalyzed by the presence of ].<ref name=1980rev /> Without the presence of any catalysts, sulfamic acid will not react with ethanol at temperatures below 100 °C. |
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:ROH + H<sub>2</sub>NSO<sub>3</sub>H → ROS(O)<sub>2</sub>O<sup>−</sup> + {{chem|NH|4|+}} |
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An example of this reaction is the production 2-ethylhexyl sulfate, a wetting agent used in the ] of cotton, by combining sulfamic acid with ]. |
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==Applications== |
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Sulfamic acid is mainly a precursor to sweet-tasting compounds. Reaction with ] followed by addition of ] gives C<sub>6</sub>H<sub>11</sub>NHSO<sub>3</sub>Na, ]. Related compounds are also ]s, such as ]. |
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Sulfamates have been used in the design of many types of therapeutic agents such as ]s, nucleoside/nucleotide ] (HIV) ]s, ]s (PIs), anticancer drugs (] and ] inhibitors), ] drugs, and ]s.<ref>{{Cite journal | last1 = Winum | first1 = J. Y. | last2 = Scozzafava | first2 = A. | last3 = Montero | first3 = J. L. | last4 = Supuran | first4 = C. T. | title = Sulfamates and their therapeutic potential | doi = 10.1002/med.20021 | journal = Medicinal Research Reviews | volume = 25 | issue = 2 | pages = 186–228 | year = 2005 | pmid = 15478125| s2cid = 1361433 | doi-access = free }}</ref> |
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===Cleaning agent=== |
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Sulfamic acid is used as an acidic ] and descaling agent sometimes pure or as a component of proprietary mixtures, typically for ]s and ]s. For cleaning purposes, there are different grades based on application such as GP Grade, SR Grade and TM Grade. It is frequently used for removing ] and ], replacing the more volatile and irritating ], which is cheaper. It is often a component of household descalant, for example, Lime-A-Way Thick Gel contains up to 8% sulfamic acid and has pH 2.0–2.2,<ref>{{cite web |url= http://www.hardwarestore.com/media/msds/125835.pdf|archive-url= https://web.archive.org/web/20110717011955/http://www.hardwarestore.com/media/msds/125835.pdf|url-status= dead|archive-date= 17 July 2011|title= Material Safety Data Sheet – Lime-A-Way Lime, Calcium and Rust Cleaner (Trigger Spray)|last=Benckiser |first=Reckitt|work= hardwarestore.com|access-date= 17 November 2011}}</ref> or ]s used for removal of ]. When compared to most of the common strong ], sulfamic acid has desirable water descaling properties, low volatility, and low toxicity. It forms water-soluble salts of calcium, nickel, and ferric iron. |
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Sulfamic acid is preferable to hydrochloric acid in household use, due to its intrinsic safety. If inadvertently mixed with hypochlorite based products such as ], it does not form ] gas, whereas the most common acids would; the reaction (]) with ], produces a salt, as depicted in the section above. |
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It also finds applications in the industrial cleaning of dairy and brewhouse equipment. Although it is considered less corrosive than ], ]s are often added to the commercial cleansers of which it is a component. It can be used as a descalant for descaling home coffee and espresso machines and in denture cleaners. |
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===Other uses=== |
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* ] for ] process |
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* ] and ] manufacturing |
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* ], as ] |
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* Descalant for scale removal |
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* Coagulator for ]s |
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* Ingredient in ]. Sulfamic acid is the main raw material for ] which is a widely used herbicide and fire retardant material for household products. |
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* Pulp and paper industry as a chloride stabilizer |
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* Synthesis of ] by reaction with nitric acid |
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* The deprotonated form (sulfamate) is a common counterion for nickel(II) in ]. |
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*Used to separate nitrite ions from mixture of nitrite and nitrate ions( NO<sub>3</sub><sup>−</sup>+ NO<sub>2</sub><sup>−</sup>) during qualitative analysis of nitrate by ]. |
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* Obtaining ]s with ]<ref>Kazachenko, Aleksandr S.; Issaoui, Noureddine; Medimagh, Mouna; Yu. Fetisova, Olga; Berezhnaya, Yaroslava D.; Elsuf'ev, Evgeniy V.; Al-Dossary, Omar M.; Wojcik, Marek J.; Xiang, Zhouyang; Bousiakou, Leda G. "Experimental and theoretical study of the sulfamic acid-urea deep eutectic solvent" (2022) Journal of Molecular Liquids, 363, art. no. 119859 DOI: 10.1016/j.molliq.2022.119859</ref> |
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===Silver polishing=== |
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According to the label on the consumer product, the silver cleaning product TarnX contains ], a ], and sulfamic acid. |
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==References== |
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{{Reflist|30em}} |
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==Further reading== |
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* {{cite web |url= http://www.osha.gov/dts/chemicalsampling/data/CH_268428.html|title= Chemical Sampling Information – Sulfamic Acid|date= 6 May 1997|publisher= Occupational Health & Safety Administration|access-date= 17 November 2011}} |
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* {{cite book |last1= Cremlyn|first1= R. J.|title= An Introduction to Organosulfur Chemistry|year= 1996|publisher= John Wiley and Sons|location= Chichester|isbn= 978-0-471-95512-2}} |
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* {{Greenwood&Earnshaw}} |
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{{Commons category|Sulfamic acid}} |
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{{Hydrogen compounds}} |
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] |
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] |
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] |
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] |
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] |