| Revision as of 12:25, 4 August 2011 editLamro (talk | contribs)Autopatrolled, Extended confirmed users84,272 edits link← Previous edit |
Latest revision as of 13:28, 8 January 2024 edit undoBernardirfan (talk | contribs)Extended confirmed users10,991 edits Dead code |
| (35 intermediate revisions by 25 users not shown) |
| Line 1: |
Line 1: |
|
{{Chembox |
|
{{Chembox |
|
|
| Verifiedfields = changed |
| ⚫ |
| verifiedrevid = 402026561 |
|
|
|
| Watchedfields = changed |
|
⚫ |
| verifiedrevid = 443004403 |
|
| ImageFile = Methyl hydrogen sulfate.png |
|
| ImageFile = Methyl hydrogen sulfate.png |
|
| ImageSize = 150px |
|
| ImageSize = 150px |
|
|
| ImageAlt = Skeletal formula |
|
| IUPACName = |
|
|
|
| ImageFile1 = Methyl bisulfate-Molecule-3D-balls-by-AHRLS 2011.png |
| ⚫ |
| OtherNames = Methyl sulfate; Methylsulfuric acid; Methyl hydrogen sulfate; Monomethyl sulfate |
|
|
|
| ImageSize1 = 160 |
|
|
| ImageAlt1 = Ball-and-stick model |
|
|
| ImageCaption1 = {{legend|yellow|], S}}{{legend|red|], O}}{{legend|black|], C}}{{legend|white|], H}} |
|
|
| PIN = Methyl hydrogen sulfate |
|
|
| SystematicName = Methoxysulfonic acid |
|
⚫ |
| OtherNames = {{ubl|Methyl sulfate|Metilsulfate|Methylsulfuric acid|Monomethyl sulfate}} |
|
| Section1 = {{Chembox Identifiers |
|
| Section1 = {{Chembox Identifiers |
|
|
| CASNo_Ref = {{cascite|correct|??}} |
|
| CASNo = 75-93-4 |
|
| CASNo = 75-93-4 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
| ⚫ |
| PubChem = |
|
|
|
| UNII = R24I7CLU7K |
|
|
| ChEBI_Ref = {{ebicite|changed|EBI}} |
|
|
| ChEBI = 17760 |
|
|
| EINECS = 201-058-1 |
|
⚫ |
| PubChem = 6412 |
|
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|
|
| ChemSpiderID = 6172 |
|
|
| RTECS = |
|
|
| MeSHName = |
|
|
| KEGG_Ref = {{keggcite|changed|kegg}} |
|
|
| KEGG = C00200 |
|
| SMILES = OS(OC)(=O)=O |
|
| SMILES = OS(OC)(=O)=O |
|
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChI = 1S/CH4O4S/c1-5-6(2,3)4/h1H3,(H,2,3,4) |
|
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChIKey = JZMJDSHXVKJFKW-UHFFFAOYSA-N |
|
}} |
|
}} |
|
| Section2 = {{Chembox Properties |
|
| Section2 = {{Chembox Properties |
|
|
| Formula = {{chem2|(CH3)HSO4}} |
|
| C=1 | H=4 | O=4 | S=1 |
|
| C=1|H=4|O=4|S=1 |
|
| Appearance = |
|
| Appearance = |
|
| Density = |
|
| Density = |
| Line 17: |
Line 42: |
|
| BoilingPt = |
|
| BoilingPt = |
|
| Solubility = }} |
|
| Solubility = }} |
|
| Section3 = {{Chembox Hazards |
|
| Section7 = {{Chembox Hazards |
|
| MainHazards = |
|
| MainHazards = |
|
| FlashPt = |
|
| FlashPt = |
|
| Autoignition = }} |
|
| AutoignitionPt = }} |
|
}} |
|
}} |
|
|
|
|
|
'''Methyl bisulfate''' is a chemical compound with the molecular formula CH<sub>3</sub>OSO<sub>3</sub>H. This compound is the mono-] ] of ]. The significance of methyl bisulfate is that it is an intermediate in the hydrolysis of the important reagent ], (CH<sub>3</sub>)<sub>2</sub>SO<sub>4</sub>:<ref>{{cite journal | year=1966 | title=The Hydrolysis of Dimethyl Sulfate and Diethyl Sulfate in Water | journal=Canadian Journal of Chemistry | volume=44 | pages=1728–1730 | last1=Robertson | first1=R. E. | last2=Sugamon | first2=S.E. | doi=10.1139/v66-260 | issue=14}}</ref> |
|
'''Methyl bisulfate''' is a chemical compound with the molecular formula {{chem2|(CH3)HSO4}}. This compound is the mono-] ] of ]. Its structure is {{chem2|CH3\sO\sS(\dO)2\sOH}}. The significance of methyl bisulfate is that it is an intermediate in the hydrolysis of the important reagent ], {{chem2|(CH3)2SO4}}:<ref>{{cite journal | year=1966 | title=The Hydrolysis of Dimethyl Sulfate and Diethyl Sulfate in Water | journal=Canadian Journal of Chemistry | volume=44 | pages=1728–1730 | last1=Robertson | first1=R. E. | last2=Sugamon | first2=S.E. | doi=10.1139/v66-260 | issue=14| doi-access=free}}</ref> |
|
|
:{{chem2|(CH3)2SO4 + H2O → (CH3)HSO4 + ]}} |
|
:(CH<sub>3</sub>)<sub>2</sub>SO<sub>4</sub> + H<sub>2</sub>O → (CH<sub>3</sub>)HSO<sub>4</sub> + CH<sub>3</sub>OH |
|
|
|
|
|
|
Methyl bisulfate is an acid: |
|
Methyl bisulfate is a strong acid: |
|
|
:{{chem2|(CH3)HSO4 → (CH3)SO4− + ]}} |
|
:(CH<sub>3</sub>)HSO<sub>4</sub> → (CH<sub>3</sub>)SO<sub>4</sub><sup>-</sup> + H<sup>+</sup> |
|
|
|
|
|
|
Methyl bisulfate came into the public view in 1993 with the discovery that certain mercury compounds catalyze the conversion of methane to methylbisulfate in good yields with excellent selectivity in concentrated sulfuric acid.<ref>{{cite journal | title = A Mercury-Catalyzed, High-Yield System for the Oxidation of Methane to Methanol | journal = Science| year = 1993| volume =259 | issue = 5093| pages= 340–343 | last1 = Periana| first1 = R.A. | last2 = Taube | first2 = D.J. | last3 = Evitt | first3 = E.R. | pmid = 17832346 | last4 = Loffler| first4 = D.G. | last5 = Wentrcek | first5 = P.R. | last6 = Voss | first6 =G. | last7 =Masuda | first7 = T. | doi = 10.1126/science.280.5363.493f}}</ref> However, because of the toxicity and concerns with the use of mercury it wasn't until 1998 when platinum complexes were found that catalyze the reaction of ] by SO<sub>3</sub> and O<sub>2</sub> that it came into the limelight:<ref>{{cite journal | title = The Possible Role of SO<sub>3</sub> as an Oxidizing Agent in Methane Functionalization by the Catalytica Process. A Density Functional Theory Study | journal = Organometallics | year = 2003 | volume =22 | pages= 1668–1674 | last1 = Hristov | first1 = I. H. | last2 = Ziegler | first2 = T. | doi = 10.1021/om020774j | issue = 8}}</ref><ref>{{cite journal | title = High Yield Conversion of Methane to Methyl Bisulfate Catalyzed by Iodine Cations | journal = Chemical Communications | year = 2002 | pages = 2376–2377 | last1 = Periana | first1 = R. A. | last2 = Mirinov | first2 = O. | last3 = Taube | first3 = D. J. | last4 = Gamble | first4 = S | doi = 10.1039/b205366g | issue = 20}}</ref><ref>{{cite journal | author = Wolf, D. | title = High Yields of Methanol from Methane by C-H Bond Activation at Low Temperatures | journal = Angewandte Chemie, International Edition | year = 1999 | volume = 37 | pages = 3351–3353 | doi = 10.1002/(SICI)1521-3773(19981231)37:24<3351::AID-ANIE3351>3.0.CO;2-U | issue = 24}}</ref> |
|
Methyl bisulfate came into the public view in 1993 with the discovery that certain ] compounds ] the ] of ] to methylbisulfate in good yields with excellent selectivity in concentrated ].<ref>{{cite journal | title = A Mercury-Catalyzed, High-Yield System for the Oxidation of Methane to Methanol | journal = Science| year = 1993| volume =259 | issue = 5093| pages= 340–343 | last1 = Periana| first1 = R.A. | last2 = Taube | first2 = D.J. | last3 = Evitt | first3 = E.R. | pmid = 17832346 | last4 = Loffler| first4 = D.G. | last5 = Wentrcek | first5 = P.R. | last6 = Voss | first6 =G. | last7 =Masuda | first7 = T. | doi = 10.1126/SCIENCE.259.5093.340}}</ref> However, because of the toxicity and concerns with the use of mercury it wasn't until 1998 when platinum complexes were found that catalyze the reaction of ] by ] and ] that it came into the limelight:<ref>{{cite journal | title = The Possible Role of SO<sub>3</sub> as an Oxidizing Agent in Methane Functionalization by the Catalytica Process. A Density Functional Theory Study | journal = Organometallics | year = 2003 | volume =22 | pages= 1668–1674 | last1 = Hristov | first1 = I. H. | last2 = Ziegler | first2 = T. | doi = 10.1021/om020774j | issue = 8}}</ref><ref>{{cite journal | title = High Yield Conversion of Methane to Methyl Bisulfate Catalyzed by Iodine Cations | journal = Chemical Communications | year = 2002 | pages = 2376–2377 | last1 = Periana | first1 = R. A. | last2 = Mirinov | first2 = O. | last3 = Taube | first3 = D. J. | last4 = Gamble | first4 = S | doi = 10.1039/b205366g | issue = 20}}</ref><ref>{{cite journal | author = Wolf, D. | title = High Yields of Methanol from Methane by C-H Bond Activation at Low Temperatures | journal = Angewandte Chemie International Edition | year = 1999 | volume = 37 | pages = 3351–3353 | doi = 10.1002/(SICI)1521-3773(19981231)37:24<3351::AID-ANIE3351>3.0.CO;2-U | issue = 24}}</ref> |
|
|
|
|
|
|
:{{chem2|2 CH4 + 2 SO3 + O2 → 2 (CH3)HSO4}} |
|
:CH<sub>4</sub> + SO<sub>3</sub> + <sup>1</sup>/<sub>2</sub> O<sub>2</sub> → (CH<sub>3</sub>)HSO<sub>4</sub> |
|
|
This discovery pointed to a possible method for upgrading inexpensive and abundantly available methane (]) into ], which is both a more useful chemical and more easily shipped than methane. The process is proposed to proceed via an intermediate containing the Pt-CH<sub>3</sub> group.<ref>{{cite journal | title = Platinum Catalysts for the High-Yield Oxidation of Methane to a Methanol Derivative | journal = Science | year = 1998 | volume = 280 | pages = 560–564 | last1 = Periana | first1 = R. A. | last2 = Taube | first2 = D. J. | last3 = Gamble | first3 = S. | last4 = Taube | first4 = H. | last5 = Satoh | first5 = T. | last6 = Fujii | first6 = H. | doi = 10.1126/science.280.5363.560 | pmid = 9554841 | issue = 5363}}</ref> |
|
This discovery pointed to a possible method for upgrading inexpensive and abundantly available methane (]) into ], which is both a more useful chemical and more easily shipped than methane. The process is proposed to proceed via an intermediate containing the {{chem2|]\s]}} group.<ref>{{cite journal | title = Platinum Catalysts for the High-Yield Oxidation of Methane to a Methanol Derivative | journal = Science | year = 1998 | volume = 280 | pages = 560–564 | last1 = Periana | first1 = R. A. | last2 = Taube | first2 = D. J. | last3 = Gamble | first3 = S. | last4 = Taube | first4 = H. | last5 = Satoh | first5 = T. | last6 = Fujii | first6 = H. | doi = 10.1126/science.280.5363.560 | pmid = 9554841 | issue = 5363}}</ref> |
|
|
|
|
|
|
Methyl bisulfate's ] is used as a ] in the ] of some ]s, where it is typically referred to as '''metilsulfate'''.<ref>{{cite book | title = International nonproprietary names (INN) for pharmaceutical substances | publisher = ]}}</ref> |
|
Salts of (CH<sub>3</sub>)SO<sub>4</sub><sup>-</sup> are commercially available, e.g. tris(2-hydroxyethyl)methylammonium methylsulfate (CAS #29463-06-7). |
|
|
|
|
|
|
==References== |
|
==References== |
| Line 40: |
Line 65: |
|
|
|
|
|
] |
|
] |
|
] |
|
] |
|
|
] |
|
|
|
|
] |
|