2404-73-1Relevant academic research and scientific papers
Microwave-assisted ionic liquid-catalyzed selective monoesterification of alkylphosphonic acids—an experimental and a theoretical study
Harsági, Nikoletta,Henyecz, Réka,ábrányi-Balogh, Péter,Drahos, László,Keglevich, Gy?rgy
, (2021/09/07)
It is well-known that the P-acids including phosphonic acids resist undergoing direct es-terification. However, it was found that a series of alkylphoshonic acids could be involved in mo-noesterification with C2–C4 alcohols under microwave (MW) irradiation in the presence of [bmim][BF4] as an additive. The selectivity amounted to 80–98%, while the isolated yields fell in the range of 61–79%. The method developed is a green method for P-acid esterification. DFT calculations at the M062X/6–311+G (d,p) level of theory (performed considering the solvent effect of the corresponding alcohol) explored the three-step mechanism, and justified a higher enthalpy of activation (160.6–194.1 kJ·mol–1) that may be overcome only by MW irradiation. The major role of the [bmim][BF4] additive is to increase the absorption of MW energy. The specific chemical role of the [BF4] anion of the ionic liquid in an alternative mechanism was also raised by the computations.
RESORCINOL DERIVATIVES FOR THEIR COSMETIC USE
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Page/Page column 17; 18, (2018/12/13)
The invention relates to resorcinol derivatives of formula (I) and also the salts thereof, the solvates thereof and the optical and/or geometrical isomers thereof, including enantiomers and diastereoisomers, and the racemic mixtures thereof, alone or as a mixture. The invention also relates to a cosmetic process for depigmenting, lightening and/or bleaching keratin materials, especially the skin, using these compounds (I).
Polymer-supported sulfonated magnetic resin: An efficient reagent for esterification of O-alkyl alkylphosphonic-and carboxylic-acids
Purohit, Ajay Kumar,Kumar, Ajeet,Singh, Varoon,Goud D, Raghavender,Jain, Rajiv,Dubey
supporting information, p. 6844 - 6846 (2015/01/09)
A mild and efficient synthetic method has been developed for the esterification of O-alkyl alkylphosphonic-and carboxylic-acids using polymer-supported sulfonated magnetic resins. Polymer-supported resins are recovered using an external magnet and reused several times.
A convenient method to access long-chain and functionalised mixed methylphosphonate esters and their application in the synthesis of ionic liquids
Sachnov, Swetlana J.,Schulz, Peter S.,Wasserscheid, Peter
supporting information; body text, p. 11234 - 11236 (2011/12/05)
A new method to synthesise long-chain and functionalised methylphosphonate esters and the corresponding ionic liquids is reported. The synthesis comprises the formation of dialkyl methylphosphonate esters in a SN2 reaction followed by the use of these esters as alkylating agents to form the corresponding, new alkyl methylphosphonate ILs.
The Michaelis-Becker reaction in phosphonium and imidazolium ionic liquids
Vu, Anh P.,Shaffer, Erika A.,Byington Congiardo, Laura K.,Knight, D. Andrew
scheme or table, p. 1845 - 1849 (2010/11/02)
The Michaelis-Becker reaction was performed in imidazolium ionic liquids using sodium hydroxide as base or sodium dialkylphosphites with good yield and selectivities. The analogous reaction performed in phosphonium ionic liquids resulted in decomposition to phosphine oxides. Copyright
P-Toluenesulfonic acid-Celite as a reagent for synthesis of esters of alkylphosphonic acids under solvent-free conditions
Gupta, Arvind K.,Kumar, Rajesh,Dubey, Devendra K.,Kaushik
, p. 328 - 331 (2008/02/10)
The coupling reaction of alkylphosphonic acids and alcohols on the surface of p-toluenesulfonic acid-Celite under mild and solvent-free conditions gave the corresponding phosphonates in excellent yields. This method provides a useful rapid synthesis of phosphonates for use in the unambiguous identification of chemical warfare agents.
An efficient method for the esterification of phosphonic and phosphoric acids using silica chloride
Sathe, Manisha,Gupta, Arvind K.,Kaushik
, p. 3107 - 3109 (2007/10/03)
Silica chloride is used as an effective heterogeneous catalyst for the rapid esterification of alkyl/aryl phosphonic/phosphoric acids to their corresponding alkyl/aryl phosphonates/phosphates under mild conditions with quantitative yields.
Phase-transfer-catalyzed Michaelis-Becker synthesis of dialkyl methyl phosphonates
Fakhraian, Hossein,Mirzaei, Akbar
, p. 511 - 518 (2007/10/03)
A liquid-liquid phase-transfer-catalyzed (PTC) Michaelis-Becker reaction was adopted in the preparation of dialkyl methyl phosphonate (R=Me, iPr; nBu, and iBu). This was performed by the reaction of an appropriate dialkyl hydrogen phosphonate with methyl iodide in the presence of benzyl triethyl ammonium chloride and sodium hydroxide as PTC and base, respectively. A liquid-liquid two-phase system (H2O/CH2Cl2) introduced a suitable situation for the preparation of dialkyl methyl phosphonates with bulky alkyl groups (R=iPr, nBu, and iBu), but with R=Me, the hydrolysis of dimethyl hydrogen phosphonate (reagent) reduced the yield to 22%. In this case, a solid-liquid PTC-free system was successfully applied and yield of over 80% was obtained. Copyright Taylor & Francis Group, LLC.
Surface-mediated solid phase reactions: A simple, efficient and base-free synthesis of phosphonates and phosphates on Al2O3
Acharya, Jyotiranjan,Shakya, Purushottam D.,Pardasani, Deepak,Palit, Meehir,Dubey, Devendra K.,Gupta, Arvind K.
, p. 194 - 196 (2007/10/03)
Al2O3-supported solvent free condensation of alkylphosphonic dichlorides with alcohols at room temperature yielded phosphorus esters in excellent yields.
