Liang–Barsky algorithm: Difference between revisions

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{{chembox
38 year-old Engineering Specialists Greg Chavous from La Malbaie, has hobbies for example r/c cars, new launch property singapore and ornithology.  that covered taking a trip to National History Park – Citadel.<br><br>Feel free to surf to my blog post - [http://stage.meclub.com/content/singapore-govt-condominium The Skywoods condo video]
| verifiedrevid = 476994839
| Name = Sulfamic acid
| ImageFile = Zwitterion Structural Formulae V.1.svg
| ImageSize = 220px
| ImageName = Tautomerism of sulfamic acid
| ImageFileL1 = Sulfamic_acid.png
| ImageSizeL1 = 110px
| ImageNameL1 = Ball-and-stick model of the canonical neutral form
| ImageFileR1 = Sulfamic acid zwitterion stick ball.png
| ImageSizeR1 = 110px
| ImageNameR1 = Ball-and-stick model of the zwitterionic form
| ImageFile2 = Sample of sulfamic acid.jpg
| ImageSize2 = 250px
| IUPACName = Sulfamic acid
| Section1 = {{Chembox Identifiers
|  ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5767
| PubChem = 5987
| InChI = 1/H3NO3S/c1-5(2,3)4/h(H3,1,2,3,4)
| InChIKey = IIACRCGMVDHOTQ-UHFFFAOYAK
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 9330
| SMILES = O=S(=O)(O)N
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 68253
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/H3NO3S/c1-5(2,3)4/h(H3,1,2,3,4)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IIACRCGMVDHOTQ-UHFFFAOYSA-N
| CASNo = 5329-14-6
|    CASNo_Ref = {{cascite|correct|CAS}}
|  UNNumber = 2967
|  EINECS = 226-218-8
|  RTECS = WO5950000
  }}
| Section2 = {{Chembox Properties
|  Formula = H<sub>3</sub>NSO<sub>3</sub>
|  MolarMass = 97.10 g/mol
|  Appearance = white crystals
|  MeltingPt = 205 °C decomp.
|  Density = 2.15 g/cm<sup>3</sup>
|  Solubility = moderate, with slow hydrolysis
|  pKa = 1.0<ref>{{cite doi|10.1039/JR9600004236}}</ref>
  }}
| Section7 = {{Chembox Hazards
|  ExternalMSDS = [http://www.inchem.org/documents/icsc/icsc/eics0328.htm ICSC 0328]
|  EUIndex = 016-026-00-0
|  EUClass = Irritant ('''Xi''')
|  RPhrases = {{R36/38}} {{R52/53}}
|  SPhrases = {{S2}} {{S26}} {{S28}} {{S61}}
|  NFPA-H =
|  NFPA-F =
|  NFPA-R =
|  NFPA-O =
|  FlashPt =
  }}
| Section8 = {{Chembox Related
|  OtherAnions =
|  OtherCations = [[Ammonium sulfamate]]
|  OtherFunctn =
|    Function =
|  OtherCpds =
  }}
}}
 
'''Sulfamic acid''', also known as '''amidosulfonic acid''', '''amidosulfuric acid''', '''aminosulfonic acid''', and '''sulfamidic acid''', is a molecular compound with the formula H<sub>3</sub>NSO<sub>3</sub>. This colorless, water-soluble compound finds many applications. Sulfamic acid melts at 205 °C before decomposing at higher temperatures to H<sub>2</sub>O, SO<sub>3</sub>, SO<sub>2</sub>, and N<sub>2</sub>.<ref name ="kirk-othmer">{{cite doi|10.1002/0471238961.1921120625151908.a01}}</ref>
 
Sulfamic acid (H<sub>3</sub>NSO<sub>3</sub>) may be considered an intermediate compound between [[sulfuric acid]] (H<sub>2</sub>SO<sub>4</sub>), and [[sulfamide]] (H<sub>4</sub>N<sub>2</sub>SO<sub>2</sub>), effectively - though see [[#Structure and reactivity|below]] - replacing an -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> group.  '''Sulfamates''' are derivatives of sulfamic acid.
 
==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(NH<sub>2</sub>)<sub>2</sub>  +  SO<sub>3</sub>  →  OC(NH<sub>2</sub>)(NHSO<sub>3</sub>H)
: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>
 
In this way, approximately 96,000 tons were produced in 1995.<ref>A. Metzger "Sulfamic Acid" in Ullmann's Encyclopedia of Industrial Chemistry, 2012, Wily-VCH, Weinheim. {{DOI|10.1002/14356007.a25_439}}</ref>
 
==Structure and reactivity==
The compound is well described by the formula H<sub>3</sub>NSO<sub>3</sub>, not the [[tautomer]] H<sub>2</sub>NSO<sub>2</sub>(OH). The relevant bond distances are S=O, 1.44 and S-N 1.77 [[Ångström|Å]]. The greater length of the S-N distance is consistent with a single bond.<ref>{{cite doi|10.1107/S0567740877002568}}</ref> Furthermore, a [[neutron diffraction]] study located the hydrogen atoms, all three of which are 1.03 [[Ångström|Å]] distant from nitrogen.<ref name="Sass">{{cite doi|10.1107/S0365110X60000789}}</ref> In the solid state, the molecule of sulfamic acid is well described by a [[zwitterion]]ic form :
 
{|align="center" class="wikitable"
|<center>[[File:Sulfamic-acid-from-xtal-3D-balls.png|150px]]</center>
|-
|<center>[[Ball-and-stick model]] of a sulfamic<br>acid zwitterion in the crystal<ref name="Sass" /></center>
|}
 
Water solutions are unstable and slowly hydrolyze to [[ammonium bisulfate]], but the crystalline solid is indefinitely stable under ordinary storage conditions. Its behavior resembles that of [[urea]], (H<sub>2</sub>N)<sub>2</sub>CO. Both feature [[amino group]]s linked to electron-withdrawing centers that can participate in [[delocalized bond]]ing. Both liberate [[ammonia]] upon heating in water.
 
===Acid-base reactions===
Sulfamic acid is a moderately strong acid, ''K''<sub>a</sub> = 1.01 x 10<sup>&minus;1</sup>. Because the solid is non-[[hygroscopic]], it is used as a standard in [[acidimetry]] (quantitative assays of acid content).
 
:H<sub>3</sub>NSO<sub>3</sub> + NaOH → NaH<sub>2</sub>NSO<sub>3</sub> + H<sub>2</sub>O
 
Double deprotonation can be effected in [[ammonia|NH<sub>3</sub>]] solution to give [HNSO<sub>3</sub>]<sup>2&minus;</sup>.<ref name ="L.B. Clapp">{{cite doi|10.1021/ed020p189}}</ref>
 
:H<sub>3</sub>NSO<sub>3</sub> + 2 NH<sub>3</sub> → [HNSO<sub>3</sub>]<sup>2&minus;</sup> + 2 [NH<sub>4</sub>]<sup>+</sup>
 
===Reaction with nitric and nitrous acids===
With [[nitrous acid|HNO<sub>2</sub>]], sulfamic acid reacts to give [[nitrogen|N<sub>2</sub>]], while with [[nitric acid|HNO<sub>3</sub>]], it affords [[nitrous oxide|N<sub>2</sub>O]].
 
: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
: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
 
===Reaction with hypochlorite===
The reaction of excess [[hypochlorite]] with sulfamic acid or a sulfamate salt gives rise reversibly to both N-chlorosulfamate and N,N-dichlorosulfamate.<ref>{{cite patent|US|3328294}}</ref><ref>{{cite patent|FR|2087248}}</ref><ref>{{cite doi|10.1021/cr60324a002}}</ref>
 
:HClO + H<sub>2</sub>NSO<sub>3</sub>H → ClNHSO<sub>3</sub>H + H<sub>2</sub>O
:HClO + ClNHSO<sub>3</sub>H <math>\rightleftarrows</math> Cl<sub>2</sub>NSO<sub>3</sub>H + H<sub>2</sub>O
 
Consequently sulfamic acid is used as hypochlorite scavenger in the oxidation of [[aldehydes]] with [[chlorite]] such as the [[Pinnick oxidation]].
 
==Applications==
Sulfamic acid is mainly a precursor to sweet-tasting compounds. Reaction with [[cyclohexylamine]] followed by addition of [[sodium hydroxide|NaOH]] gives C<sub>6</sub>H<sub>11</sub>NHSO<sub>3</sub>Na, [[sodium cyclamate]]. Related compounds are also [[sweetener]]s, see [[acesulfame potassium]].
 
Sulfamates have been used in the design of many types of therapeutic agents such as [[antibiotic]]s, nucleoside/nucleotide [[human immunodeficiency virus]] (HIV) [[reverse transcriptase inhibitor]]s, [[HIV protease inhibitor]]s (PIs), anti-cancer drugs ([[steroid sulfatase]] and [[carbonic anhydrase]] inhibitors), anti-[[epilepsy|epileptic]] drugs, and [[weight loss drug]]s.<ref>{{cite doi|10.1002/med.20021}}</ref>
 
===Cleaning agent===
Sulfamic acid is used as an acidic [[cleaning agent]], sometimes pure or as a component of proprietary mixtures, typically for [[metal]]s and [[ceramic]]s. It is frequently used for removing [[rust]] and [[limescale]], replacing the more volatile and irritating [[hydrochloric acid]], which is however cheaper.  It is often a component of household [[descaling agent]]s, for example, Lime-A-Way Thick Gel contains up to 8% sulfamic acid and pH 2 - 2.2,<ref>{{cite web |url= http://www.hardwarestore.com/media/msds/125835.pdf|title= Material Safety Data Sheet - Lime-A-Way Lime, Calcium and Rust Cleaner (Trigger Spray)|last=Benckiser |first=Reckitt|work= hardwarestore.com|accessdate= 17 November 2011}}</ref> or [[detergent]]s used for removal of [[limescale]]. When compared to most of the common strong mineral acids, sulfamic acid has desirable water descaling properties, low volatility, low toxicity.  It forms water-soluble salts of calcium and ferric iron.
 
Importantly, sulfamic acid is preferable to use in household in comparison to hydrochloric acid for its intrinsic safety. If erroneously mixed with hypochlorite based products such as [[bleach]], it does not form [[chlorine]] gas, where the most common acids would; the reaction ([[Neutralization (chemistry)|neutralization]]) with [[ammonia|NH<sub>3</sub>]], produces a salt as depicted in the section above.
 
Its also finds applications in the industrial cleaning of dairy and brew-house equipment. Although it is considered less corrosive than [[hydrochloric acid]], [[corrosion inhibitor]]s are often added to commercial cleansers of which it is a component.  Some of its domestic use, e.g. [[Easy-Off]], for descaling include  home coffee and espresso equipment and in denture cleaners.
 
===Other uses===
* [[Catalyst]] for [[esterification]] process
* [[Dye]] and [[pigment]] manufacturing
* [[Herbicide]]
* Coagulator for [[urea-formaldehyde resin]]s
* Ingredient in [[fire retardant|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 product.
* 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]].
 
===Silver polishing===
According to the label on the consumer product, the liquid silver cleaning product ''TarnX ''contains [[thiourea]], a [[detergent]], and sulfamic acid.
 
==References==
{{reflist}}
 
==External links==
* {{cite web |url= http://www.osha.gov/dts/chemicalsampling/data/CH_268428.html|title= Chemical Sampling Information - Sulfamic Acid|first= |last= |author= |authorlink= |coauthors= |date= 6 May 1997|work= |publisher= Occupational Health & Safety Administration|accessdate= 17 November 2011}}
* {{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}}
* {{Greenwood&Earnshaw}}
 
{{Commons category|Sulfamic acid}}
 
{{Hydrogen compounds}}
 
{{DEFAULTSORT:Sulfamic Acid}}
[[Category:Hydrogen compounds]]
[[Category:Sulfur oxoacids]]
[[Category:Household chemicals]]
[[Category:Cleaning product components]]
[[Category:Sulfamates]]

Latest revision as of 11:46, 9 September 2014

38 year-old Engineering Specialists Greg Chavous from La Malbaie, has hobbies for example r/c cars, new launch property singapore and ornithology. that covered taking a trip to National History Park – Citadel.

Feel free to surf to my blog post - The Skywoods condo video