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{{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 =
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| 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==
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Latest revision as of 13:28, 8 January 2024

Methyl bisulfate
Skeletal formula
Ball-and-stick model
  Sulfur, S  Oxygen, O  Carbon, C  Hydrogen, H
Names
Preferred IUPAC name Methyl hydrogen sulfate
Systematic IUPAC name Methoxysulfonic acid
Other names
  • Methyl sulfate
  • Metilsulfate
  • Methylsulfuric acid
  • Monomethyl sulfate
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.000.834 Edit this at Wikidata
EC Number
  • 201-058-1
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/CH4O4S/c1-5-6(2,3)4/h1H3,(H,2,3,4)Key: JZMJDSHXVKJFKW-UHFFFAOYSA-N
SMILES
  • OS(OC)(=O)=O
Properties
Chemical formula (CH3)HSO4
Molar mass 112.10 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Methyl bisulfate is a chemical compound with the molecular formula (CH3)HSO4. This compound is the mono-methyl ester of sulfuric acid. Its structure is CH3−O−S(=O)2−OH. The significance of methyl bisulfate is that it is an intermediate in the hydrolysis of the important reagent dimethyl sulfate, (CH3)2SO4:

(CH3)2SO4 + H2O → (CH3)HSO4 + CH3OH

Methyl bisulfate is a strong acid:

(CH3)HSO4 → (CH3)SO−4 + H

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. 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 CH4 by SO3 and O2 that it came into the limelight:

2 CH4 + 2 SO3 + O2 → 2 (CH3)HSO4

This discovery pointed to a possible method for upgrading inexpensive and abundantly available methane (natural gas) into methanol, 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−CH3 group.

Methyl bisulfate's conjugate base is used as a counterion in the formulation of some pharmaceutical drugs, where it is typically referred to as metilsulfate.

References

  1. Robertson, R. E.; Sugamon, S.E. (1966). "The Hydrolysis of Dimethyl Sulfate and Diethyl Sulfate in Water". Canadian Journal of Chemistry. 44 (14): 1728–1730. doi:10.1139/v66-260.
  2. Periana, R.A.; Taube, D.J.; Evitt, E.R.; Loffler, D.G.; Wentrcek, P.R.; Voss, G.; Masuda, T. (1993). "A Mercury-Catalyzed, High-Yield System for the Oxidation of Methane to Methanol". Science. 259 (5093): 340–343. doi:10.1126/SCIENCE.259.5093.340. PMID 17832346.
  3. Hristov, I. H.; Ziegler, T. (2003). "The Possible Role of SO3 as an Oxidizing Agent in Methane Functionalization by the Catalytica Process. A Density Functional Theory Study". Organometallics. 22 (8): 1668–1674. doi:10.1021/om020774j.
  4. Periana, R. A.; Mirinov, O.; Taube, D. J.; Gamble, S (2002). "High Yield Conversion of Methane to Methyl Bisulfate Catalyzed by Iodine Cations". Chemical Communications (20): 2376–2377. doi:10.1039/b205366g.
  5. Wolf, D. (1999). "High Yields of Methanol from Methane by C-H Bond Activation at Low Temperatures". Angewandte Chemie International Edition. 37 (24): 3351–3353. doi:10.1002/(SICI)1521-3773(19981231)37:24<3351::AID-ANIE3351>3.0.CO;2-U.
  6. Periana, R. A.; Taube, D. J.; Gamble, S.; Taube, H.; Satoh, T.; Fujii, H. (1998). "Platinum Catalysts for the High-Yield Oxidation of Methane to a Methanol Derivative". Science. 280 (5363): 560–564. doi:10.1126/science.280.5363.560. PMID 9554841.
  7. International nonproprietary names (INN) for pharmaceutical substances. World Health Organization.
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