Synthesis of α-[2-(2, 4-Dichlorophenoxy) Propionyloxy] Alkyl Phosphonates

The synthesis of thirteen new compounds α - [2 - (2, 4 -dichlorophenoxy) propionyloxy] alkyl phosphonates was described. The structures of these compounds were characterized by IR, 1H-NMR and MS.

SYNTHESES OF HINDERED ALKYL PHOSPHONATES AND PHOSPHONIC & PHOSPHINIC ACIDS

A series of di-n-hexyl alkyl phosphonates with bulky substituent on phosphorus was synthesized by PTC P-alkylation using crown ether.Upon saponification of the resulting di-n-hexyl alkylphosphonates in the presence of crown ether or quaternary ammonium halide, corresponding mono-hexyl esters of alkyl phosphonic acids were prepared.Ultrasonic wave, as we found, can catalyze the reaction between dialkyl phosphite & metallic sodium and hydrolysis of dihexyl alkyl phosphonates.A series of di-t-alkyl phosphinic acids were synthesized by the reaction of Grignard reagent with PCl_3 followed by oxidation with 30% H_2O_2.It was found that the reaction between dibutyl phosphite and Grignard reagent of t-alkyl chloride is a new synthetic method for the preparation of mono-esters of highly hindered alkyl phosphonic acids.

Amberlyst-15 catalyzed synthesis of alkyl/aryl/heterocyclic phosphonates

A novel and efficient procedure for the synthesis of alkyl phosphonates through one pot condensation of alkyl halide and trialkyl /aryl phosphite in the presence of Amberlyst-15 as catalyst under solvent free conditions was applied.It demonstrated several advantages such as good yields of products,simple operation,convenient separation and inexpensive catalyst.

Lipophilicity determination of N-( benzothiazol-2-yl )-α-amino alkyl phosphonic diesters by RP-HPLC and RP-HPTLC

Using methanol-water mixtures as the mobile phase, the chromatographic retention parameters k' and Rf were determined by reversed-phase high-performance liquid chromatography (RP-HPLC) and reversed-phase high-performance thin-layer chromatography (RP-HPTLC) for N-(benzothiazol-2-yl)-α-amino alkyl phosphoric diesters and the correlation with lipophilicity parameter (Clog P) was established. Log Kw values obtained from RP-HPLC and Rm values obtained from RP-HPTLC can be used to evaluate the lipophilicity of this kind of compounds. Chromatographic method is a good alternative for lipophilicity measurement.

A metal-OH group modification strategy to prepare highly-hydrophobic MIL-53-Al for efficient acetone capture under humid conditions

A series of highly-hydrophobic MIL-53-Al(MIL = Materials of Institut Lavoisier) frameworks synthesized via decoration of the Al-OH groups by alkyl phosphonic acid were developed as adsorbents for removing acetone from humid gas streams.The newly prepared materials were characterized by X-ray diffraction(XRD), Fourier transform infrared spectroscopy(FTIR), scanning electron microscope(SEM), N_(2) adsorption-desorption and thermogravimetric analysis(TGA).Their adsorption behaviors toward acetone vapor under dry and wet conditions were studied subsequently.Results showed that alkyl phosphonic acid was successfully grafted into MIL-53-Al skeleton through coordinating interaction with Al3+generating MIL-53-Al@C_(x)(x = 12, 14, 18).The MIL-53-Al@C_(x) exhibited similar crystal structure and thermal stability to parent MIL-53-Al.Furthermore, the modified materials showed significantly enhanced hydrophobicity.The water vapor uptake of MIL-53-Al@C_(14) decreased by 72.55%at 75% relative humidity(RH).Dynamic adsorption experiments demonstrated that water vapor had almost no effect on the acetone adsorption performance of MIL-53-Al@C_(14).Under the condition of 90% RH, the acetone adsorption capacity of MIL-53-Al@C_(14) was 102.98% higher than that of MIL-53-Al.Notably, MIL-53-Al@C_(14) presented excellent adsorption reversibility and regeneration performance in 10 adsorption-desorption cycles.Taken together, the strategy of metal-OH group modification is an attractive way to improve the acetone adsorption performance over metal-organic frameworks(MOFs) under humid conditions.Besides, MIL-53-Al@C_(14) would be deemed as a promising candidate for capturing acetone in high moisture environment.