Magnesium monoperoxyphthalate

Last updated
Magnesium monoperoxyphthalate
Magnesium monoperoxyphthalate.svg
Names
Preferred IUPAC name
Magnesium bis(2-carbonoperoxoylbenzoate)
Other names
H48; MMPP
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.071.808 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 279-013-0
PubChem CID
UNII
  • [Mg++].OOC(=O)C1=CC=CC=C1C([O-])=O.OOC(=O)C1=CC=CC=C1C([O-])=O
Properties
C16H10MgO10
Molar mass 386.551 g·mol−1
Hazards
Flash point 173.4 °C (344.1 °F; 446.5 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Magnesium monoperoxyphthalate (MMPP) is a water-soluble peroxy acid used as an oxidant in organic synthesis. Its main areas of use are the conversion of ketones to esters (Baeyer-Villiger oxidation), epoxidation of alkenes (Prilezhaev reaction), oxidation of sulfides to sulfoxides and sulfones, oxidation of amines to produce amine oxides, and in the oxidative cleavage of hydrazones. [1]

Due to its insolubility in non-polar solvents MMPP has seen less use than the more widely used meta-chloroperoxybenzoic acid (mCPBA). Although work up procedures are more simply handled in polar solvents, usage of MMPP to oxidize nonpolar substrates in biphasic media combined with a phase transfer catalyst have been inefficient. [1] Despite this MMPP has certain advantages over mCPBA including a lower cost of production and increased stability. [1]

MMPP is also used as the active ingredient in certain surface disinfectants such as Dismozon Pur. [2] As a surface disinfectant MMPP exhibits a broad spectrum biocidal effect including inactivation of endospores. [3] Its wide surface compatibility enables its use on sensitive materials, such as plastic and rubber equipment used in hospitals. Additionally MMPP has been investigated as a potential antibacterial agent for mouthwashes and toothpaste. [4]

Related Research Articles

<span class="mw-page-title-main">Dichloromethane</span> Chemical compound

Dichloromethane is an organochlorine compound with the formula CH2Cl2. This colorless, volatile liquid with a chloroform-like, sweet odor is widely used as a solvent. Although it is not miscible with water, it is slightly polar, and miscible with many organic solvents.

<span class="mw-page-title-main">Epoxide</span> Organic compounds with a carbon-carbon-oxygen ring

In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and nonpolar, and often volatile.

<span class="mw-page-title-main">Hydrogen peroxide - urea</span> Chemical compound

Hydrogen peroxide - urea is a white crystalline solid chemical compound composed of equal amounts of hydrogen peroxide and urea. It contains solid and water-free hydrogen peroxide, which offers a higher stability and better controllability than liquid hydrogen peroxide when used as an oxidizing agent. Often called carbamide peroxide in dentistry, it is used as a source of hydrogen peroxide when dissolved in water for bleaching, disinfection and oxidation.

<span class="mw-page-title-main">Quaternary ammonium cation</span> Polyatomic ions of the form N(–R)₄ (charge +1)

In organic chemistry, quaternary ammonium cations, also known as quats, are positively-charged polyatomic ions of the structure [NR4]+, where R is an alkyl group, an aryl group or organyl group. Unlike the ammonium ion and the primary, secondary, or tertiary ammonium cations, the quaternary ammonium cations are permanently charged, independent of the pH of their solution. Quaternary ammonium salts or quaternary ammonium compounds are salts of quaternary ammonium cations. Polyquats are a variety of engineered polymer forms which provide multiple quat molecules within a larger molecule.

<span class="mw-page-title-main">Magnesium nitrate</span> Chemical compound

Magnesium nitrate refers to inorganic compounds with the formula Mg(NO3)2(H2O)x, where x = 6, 2, and 0. All are white solids. The anhydrous material is hygroscopic, quickly forming the hexahydrate upon standing in air. All of the salts are very soluble in both water and ethanol.

meta-Chloroperoxybenzoic acid is a peroxycarboxylic acid. It is a white solid often used widely as an oxidant in organic synthesis. mCPBA is often preferred to other peroxy acids because of its relative ease of handling. mCPBA is a strong oxidizing agent that may cause fire upon contact with flammable material.

<span class="mw-page-title-main">Potassium peroxymonosulfate</span> Chemical compound

Potassium peroxymonosulfate is widely used as an oxidizing agent, for example, in pools and spas. It is the potassium salt of peroxymonosulfuric acid. Usually potassium peroxymonosulfate is available as the triple salt 2KHSO5·KHSO4·K2SO4, known as Oxone.

<span class="mw-page-title-main">Liquid–liquid extraction</span> Method to separate compounds or metal complexes

Liquid–liquid extraction, also known as solvent extraction and partitioning, is a method to separate compounds or metal complexes, based on their relative solubilities in two different immiscible liquids, usually water (polar) and an organic solvent (non-polar). There is a net transfer of one or more species from one liquid into another liquid phase, generally from aqueous to organic. The transfer is driven by chemical potential, i.e. once the transfer is complete, the overall system of chemical components that make up the solutes and the solvents are in a more stable configuration. The solvent that is enriched in solute(s) is called extract. The feed solution that is depleted in solute(s) is called the raffinate. Liquid-liquid extraction is a basic technique in chemical laboratories, where it is performed using a variety of apparatus, from separatory funnels to countercurrent distribution equipment called as mixer settlers. This type of process is commonly performed after a chemical reaction as part of the work-up, often including an acidic work-up.

<span class="mw-page-title-main">Phosphotungstic acid</span> Chemical compound

Phosphotungstic acid (PTA) or tungstophosphoric acid (TPA), is a heteropoly acid with the chemical formula H3PW12O40]. It forms hydrates H3[PW12O40nH2O. It is normally isolated as the n = 24 hydrate but can be desiccated to the hexahydrate (n = 6). EPTA is the name of ethanolic phosphotungstic acid, its alcohol solution used in biology. It has the appearance of small, colorless-grayish or slightly yellow-green crystals, with melting point 89 °C (24 H2O hydrate). It is odorless and soluble in water (200 g/100 ml). It is not especially toxic, but is a mild acidic irritant. The compound is known by a variety of names and acronyms (see 'other names' section of infobox).

<span class="mw-page-title-main">Amine oxide</span> Chemical compound containing the functional group R3N→O

In chemistry, an amine oxide, also known as an amine N-oxide or simply N-oxide, is a chemical compound that has the chemical formula R3N+−O. It contains a nitrogen-oxygen coordinate covalent bond with three additional hydrogen and/or substituent-groups attached to nitrogen. Sometimes it is written as R3N→O or, alternatively, as R3N=O.

Peracetic acid (also known as peroxyacetic acid, or PAA) is an organic compound with the formula CH3CO3H. This peroxy acid is a colorless liquid with a characteristic acrid odor reminiscent of acetic acid. It can be highly corrosive.

In electrochemistry, electrosynthesis is the synthesis of chemical compounds in an electrochemical cell. Compared to ordinary redox reactions, electrosynthesis sometimes offers improved selectivity and yields. Electrosynthesis is actively studied as a science and also has industrial applications. Electrooxidation has potential for wastewater treatment as well.

Aqueous normal-phase chromatography (ANP) is a chromatographic technique that involves the mobile phase compositions and polarities between reversed-phase chromatography (RP) and normal-phase chromatography (NP), while the stationary phases are polar.

<span class="mw-page-title-main">Prilezhaev reaction</span> Chemical reaction

The Prilezhaev reaction, also known as the Prileschajew reaction or Prilezhaev epoxidation, is the chemical reaction of an alkene with a peroxy acid to form epoxides. It is named after Nikolai Prilezhaev, who first reported this reaction in 1909. A widely used peroxy acid for this reaction is meta-chloroperoxybenzoic acid (m-CPBA), due to its stability and good solubility in most organic solvents. The reaction is performed in inert solvents (C6H14, C6H6, CH2Cl2, CHCl3, CCl4) between -10 and 60 °C with the yield of 60-80%.

The Fleming–Tamao oxidation, or Tamao–Kumada–Fleming oxidation, converts a carbon–silicon bond to a carbon–oxygen bond with a peroxy acid or hydrogen peroxide. Fleming–Tamao oxidation refers to two slightly different conditions developed concurrently in the early 1980s by the Kohei Tamao and Ian Fleming research groups.

<span class="mw-page-title-main">Oxaziridine</span> Chemical compound

An oxaziridine is an organic molecule that features a three-membered heterocycle containing oxygen, nitrogen, and carbon. In their largest application, oxaziridines are intermediates in the industrial production of hydrazine. Oxaziridine derivatives are also used as specialized reagents in organic chemistry for a variety of oxidations, including alpha hydroxylation of enolates, epoxidation and aziridination of olefins, and other heteroatom transfer reactions. Oxaziridines also serve as precursors to amides and participate in [3+2] cycloadditions with various heterocumulenes to form substituted five-membered heterocycles. Chiral oxaziridine derivatives effect asymmetric oxygen transfer to prochiral enolates as well as other substrates. Some oxaziridines also have the property of a high barrier to inversion of the nitrogen, allowing for the possibility of chirality at the nitrogen center.

<span class="mw-page-title-main">Vanadyl acetylacetonate</span> Chemical compound

Vanadyl acetylacetonate is the chemical compound with the formula VO(acac)2, where acac is the conjugate base of acetylacetone. It is a blue-green solid that dissolves in polar organic solvents. The coordination complex consists of the vanadyl group, VO2+, bound to two acac ligands via the two oxygen atoms on each. Like other charge-neutral acetylacetonate complexes, it is not soluble in water.

<span class="mw-page-title-main">Cerium nitrates</span> Chemical compound

Cerium nitrate refers to a family of nitrates of cerium in the +3 or +4 oxidation state. Often these compounds contain water, hydroxide, or hydronium ions in addition to cerium and nitrate. Double nitrates of cerium also exist.

<span class="mw-page-title-main">Yttrium(III) nitrate</span> Chemical compound

Yttrium(III) nitrate is an inorganic compound, a salt with the formula Y(NO3)3. The hexahydrate is the most common form commercially available.

<span class="mw-page-title-main">Epoxidation of allylic alcohols</span>

The epoxidation of allylic alcohols is a class of epoxidation reactions in organic chemistry. One implementation of this reaction is the Sharpless epoxidation. Early work showed that allylic alcohols give facial selectivity when using meta-chloroperoxybenzoic acid (m-CPBA) as an oxidant. This selectivity was reversed when the allylic alcohol was acetylated. This finding leads to the conclusion that hydrogen bonding played a key role in selectivity and the following model was proposed.

References

  1. 1 2 3 Carvalho, João F.S.; Silva, M. Manuel Cruz; Sá e Melo, M. Luisa (2009). "Highly efficient epoxidation of unsaturated steroids using magnesium bis(monoperoxyphthalate) hexahydrate". Tetrahedron. 65 (14): 2773–81. doi:10.1016/j.tet.2009.01.100.
  2. "Magnesium Monoperoxyphthalate". ndrugs. Retrieved 19 December 2013.
  3. Baldry, M.G.C. (1984). "The antimicrobial properties of magnesium monoperoxyphthalate hexahydrate". Journal of Applied Bacteriology. 57 (3): 499–503. doi:10.1111/j.1365-2672.1984.tb01416.x. PMID   6397460.
  4. Scully, Crispian; El-Kabir, Mohamed; Greenman, John; Porter, Stephen R.; Mutlu, Serdar; Barton, Ian; Adair, Richard (1999). "The effects of mouth rinses and dentifrice-containing magnesium monoperoxyphthalate (mmpp) on oral microflora, plaque reduction, and mucosa". Journal of Clinical Periodontology. 26 (4): 234–8. doi:10.1034/j.1600-051X.1999.260406.x. PMID   10223394.