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PubMed2005

Field assessment of treatment efficacy by three methods of phosphoric acid application in lead-contaminated urban soil.

In situ soil treatment using phosphoric acid (H(3)PO(4)) may be an effective remedial technology for immobilizing soil Pb and reducing Pb risk to human health and ecosystem. The treatment efficacy of three H(3)PO(4) application methods was assessed in a smelter-contaminated urban soil located in the Jasper County Superfund Site, Missouri. Soil, with an average of 3529 mg Pb kg(-1) and in the 2- by 4-m plot size, was treated with H(3)PO(4) at a rate of 10 g P kg(-1) in four replicates by each of three methods: rototilling; surface application; pressure injection. Three soil cores, 2.5-cm diameter and 30-cm long, were taken from each plot before and 90 days after treatment and analyzed for soluble P, bioaccessible Pb and solid-Pb speciation. Applications of H(3)PO(4) induced the heterogeneity of soluble P in soil, with the highest concentrations in the surface. Three application methods mixed the H(3)PO(4) more effectively in the horizontals than the verticals of treated soil zone. The H(3)PO(4) applications significantly reduced Pb bioaccessibility in the soil, which was influenced by the concentrations of soil soluble P and solid-Pb species. The risk reductions of soil Pb were achieved by formation of pyromorphites or pyromorphite-like minerals. The rototilling appears to be the most effective treatment method in context of the homogeneity of soluble P and the reduction of Pb bioaccessibility in treated soil.

Cities↗
PubMed1988

Neutralizing phosphoric acid in the acid etch resin technique.

The use of an alkaline wetting agent, used to neutralize phosphoric acid in the acid etch technique, was investigated with respect to improving the bond strength and microleakage behaviour of composite resin. The alkaline wetting agent has been shown to prevent the accumulation of calcium biphosphates, as a result of secondary recrystallization of hydroxyapatite, within the depths of etched enamel. To examine the influence of the alkaline wetting agent on bond strength, composite cylinders were prepared on enamel surfaces of extracted third molar teeth and tested for shear bond strength. Microleakage behaviour was observed on class V oval preparations in the cervical thirds of extracted third molars using a dye penetration technique. No significant improvement in shear bond strength was demonstrated with the alkaline wetting agent over conventional acid etching. In addition, the microleakage observed following the use of the alkaline wetting was characteristic of that for conventional acid etching.

Acid Etching, Dental↗
PubMed2005

Determination of phosphoric acid triesters in human plasma using solid-phase microextraction and gas chromatography coupled to inductively coupled plasma mass spectrometry.

A simple and sensitive method for determination of phosphoric acid triesters at trace levels in human plasma sample is described. In this work, solid-phase microextraction (SPME) is employed as a sample preparation procedure for extraction and pre-concentration of alkyl and aryl phosphates followed by gas chromatography coupled to inductively coupled plasma mass spectrometry (GC-ICP-MS) for phosphorus-specific and very sensitive determination of these compounds in human plasma. The detection limits from blood plasma were 50 ngL(-1) (tripropyl phosphate), 17 ngL(-1) (tributyl phosphate), 240 ngL(-1) (tris(2-chloroethyl) phosphate) and 24 ngL(-1) (triphenyl phosphate). Sample preparation involves plasma deproteinization followed by direct immersion SPME with 65 microm poly(dimethylsiloxane/divinylbenzene) fiber. Extraction was performed at 40 degrees C for 30 min and at pH 7.0 in 10 mM sodium carbonate buffer. The reported method, to our knowledge, describes the first application of SPME with element-specific detection for analysis of phosphoric acid esters. Application of the method to the plasma samples, previously stored in poly(vinyl chloride) plasma bags revealed the presence of triphenyl phosphate, which was further confirmed by SPME GC time-of-flight high-resolution mass spectrometry.

Chemical Fractionation↗
PubMed2006

Determination of phosphoric acid mono- and diesters in municipal wastewater by solid-phase extraction and ion-pair liquid chromatography-tandem mass spectrometry.

The first analytical method for the determination of 13 phosphoric acid mono- and diesters from aqueous samples is presented. The method consists of solid-phase extraction (SPE) and ion-pair liquid chromatographic separation with tri-n-butylamine coupled to electrospray ionization tandem mass spectrometry in the negative ion mode. Due to a lack of pure standards, only 3 of the 13 esters could be quantified. SPE recoveries ranged from 71 to 112% for di-n-butyl phosphate, diphenyl phosphate, and di-(2-ethylhexyl) phosphate (DEHP) with limits of quantification from 7 to 14 ng/L for 100-mL samples. At analyte concentrations >or=1 microg/L, aqueous samples can be analyzed by direct injection without extraction. In municipal wastewater, six diesters and one monoester were unambiguously identified by comparison with synthesized reference material. DEHP showed highest concentrations of 60 and 5 microg/L in raw and treated wastewater, respectively. The detection of monoethylhexyl phosphate was confirmed by LC-Q-TOF-MS analysis, and it was found at a concentration level comparable to DEHP. Laboratory degradation tests show that phosphoric acid diesters can be formed as intermediates in the microbial degradation of trialkyl phosphates that are being used as flame retardants and plasticizers.

Journal Article↗
PubMed2005

Selective synthesis of phosphate monoesters by dehydrative condensation of phosphoric acid and alcohols promoted by nucleophilic bases.

Phosphate monoesters are synthesized from a mixture of phosphoric acid (1 or 2 equiv) and alcohols (1 equiv) in the presence of tributylamine. The reaction is promoted by nucleophilic bases such as N-alkylimidazole and 4-(N,N-dialkylamino)pyridine. 2',3'-O-Isopropylidene ribonucleosides are selectively converted to their 5'-monophosphates without the protection of amino groups in nucleobases.

Alcohols↗
PubMed1994

Brushing-induced effects with and without a non-fluoride abrasive dentifrice on remineralization of enamel surfaces etched with phosphoric acid.

The remineralization of acid-etched enamel after brushing with and without a non-fluoride abrasive dentifrice was investigated using scanning electron microscopy after sodium hypochlorite (NaOCl) or ethylenediamine tetra-acetic acid treatment, of the specimens. Ground enamel pieces were etched with 30% phosphoric acid for 60 s and attached to resin plates. They were exposed to the oral environment of 4 subjects for 8 weeks and brushed for 1 min daily. Paste and brushing caused the acid-etched enamel to erode selectively, i.e., deep grooves were formed in the prism peripheral regions, while projections of the prism bodies showing a relatively low density of crystallites were retained. Brushing without dentifrice, on the other hand, caused about 0.5 micron thick pellicle with tag-like structures to cover the etched enamel. Fine mineral granules, presumably derived from saliva and minute fragments of etched crystallites, were precipitated on the enamel surface as a thin layer with the pellicle. These results indicate that daily brushing without dentifrice induces the remineralization of acid-etched enamel by depositing salivary components, while paste brushing will lead to abrasion of the weakened enamel.

Acid Etching, Dental↗
PubMed2004

Spectrophotometric determination of deacetylation degree of chitinous materials dissolved in phosphoric acid.

A simple spectrophotometric method is proposed for determining deacetylation degrees (DD) of chitinous materials using phosphoric acid as the UV-transparent solvent system. Calibrating by the extinction coefficients (A(210)) of D-glucosamine and N-acetyl-D-glucosamine, DD values (24-88%) were computed numerically. The results correlated well (R(2) = 0.9805, n = 50) with those obtained by solid-state (13)C NMR. Comparison of the results obtained by the proposed UV method and solid-state (13)C NMR.

Acetylation↗
PubMed2006

Aqueous phosphoric acid as a mild reagent for deprotection of tert-butyl carbamates, esters, and ethers.

Aqueous phosphoric acid (85 wt %) is an effective, environmentally benign reagent for the deprotection of tert-butyl carbamates, tert-butyl esters, and tert-butyl ethers. The reaction conditions are mild and offer good selectivity in the presence of other acid-sensitive groups, including CBZ carbamates, azetidine, benzyl and methyl esters, TBDMS, and methyl phenyl ethers. The mildness of the reaction is further demonstrated in the synthesis of clarithromycin derivative, in which a tert-butyl ester is removed in the presence of cyclic carbamate, lactone, ketal, acetate ester, and epimerizable methyl ketone functionalities. The reaction preserves the stereochemical integrity of the substrates. The reactions are high yielding, and the workup is convenient.

Carbamates↗
PubMed1996

pH-Zone refining counter-current chromatography of polar catecholamines using di-(2-ethylhexyl)phosphoric acid as a ligand.

The use of di-(2-ethylhexyl)phosphoric acid (DEHPA) as a ligand in the stationary phase effectively increased the partition coefficient of polar catecholamines. pH-Zone refining counter-current chromatography of six components, i.e. five catecholamines and one amino acid (DOPA), was successfully performed using a two-phase solvent system composed of methyl tert.-butyl ether and water by adding DEHPA (20%) and ammonium acetate (200 mM) to the organic phase and HCl (50 mM) to the aqueous mobile phase. DOPA was eluted first as a normal peak followed by the five catecholamines which formed a succession of highly concentrated rectangular peaks associated with sharp impurity peaks at their borders (UV tracing at 280 nm). Both pH and standard partition coefficient of collected fractions indicated minimum overlap between the main peaks. Each component was identified by NMR analysis.

Catecholamines↗
PubMed2003

Polarised vibrational spectra of betaine ortho-phosphoric acid complex. Part II. Phase transitions studies.

Polarised infrared transmission and Raman spectra of betaine ortho-phosphoric acid crystal in temperature ranges 13-393 and 13-300 K, respectively are reported and discussed in relation to phase transitions: antiferrodistortive at T(c1) = 365 K and antiferroelectric at T(c3) = 81 K. The spectra are consistent with unit cell doubling below T(c3). The participation of all hydrogen bonds apparent in the crystal in the antiferroelectric phase transition was shown. Quite large freedom of -N(CH(3))(3) groups reorientation in the antiferroelectric phase was detected. No changes were found in the transmission spectra taken in the vicinity of the antiferrodistortive phase transition temperature.

Betaine↗
PubMed2001

Effects of phosphoric acid and glutaraldehyde-HEMA on dentin collagen.

The purpose of this study was to evaluate the effects of phosphoric acid (PA) and a proprietary glutaraldehyde-HEMA aqueous solution (Gluma Desensitizer; GD) on dentin collagen. Specimens of demineralized bovine dentin collagen were treated with either 37% or 50% PA for 1 or 5 min. An additional set of specimens was treated with 37% PA for 1 min followed by GD for 1 min. All specimens were washed with distilled water, lyophilized. reduced with standardized NaB3H4, hydrolyzed with 6 M HCl and subjected to amino acid and cross-link analyses. The results demonstrated that the treatment of demineralized dentin with PA under the conditions tested did not significantly alter the collagen cross-links. The GD-treated samples showed reduction of free lysine (Lys) and hydroxylysine (Hyl) residues, as well as a decrease in the levels of collagen reducible cross-links. In addition, unidentified reducible compounds were detected by high-performance liquid chromatography (HPLC) analysis. These compounds may be derived from cross-links formed between GD-derived aldehyde and Lys/Hyl of collagen. The findings indicate that PA treatment does not significantly affect dentin collagen amino acid and cross-link composition, and that GD treatment affects dentin collagen amino acid and cross-link composition.

Amino Acids↗
PubMed2006

V-shaped crystalline structures of di-n-alkyl esters of phosphoric acid.

We prepared crystals of di-n-alkyl esters of phosphoric acid with chain lengths of n = 10, 12, 14, 16, and 18. These were characterized by single-crystal X-ray analysis and differential scanning calorimetry (DSC). It was found that the alkyl chains are in an extended all-trans conformation and aligned close to perpendicular, forming V-shaped molecules. This is in strong contrast to the typical arrangement of the alkyl chains of phospholipids where the two alkyl chains are arranged parallel in the same direction (e.g., tuning fork configuration in bilayers). Additionally, it was found that the arrangement of the V-shaped molecules of the di-n-alkyl esters in neighboring stacks of the lamellar crystals is antiparallel for short chain lengths (n = 10 and 12) and parallel for the longer (n = 14 and 16). DSC reveals that the melting of the crystals increases systematically with increasing chain lengths from 48 to 82 degrees C. The contribution of each methylene group to the melting enthalpy (70-133 kJ/mol) is independent of the chain length (3.9 kJ per mol CH2).

Journal Article↗
PubMed1988

Behaviour of plasmalogens during high-performance liquid chromatography on a silica column with a mobile phase containing phosphoric acid.

Silica high-performance liquid chromatographic separation of phospho- and sphingolipids of biological origin using a mobile phase containing phosphoric acid leads to gradual hydrolysis of plasmalogens during their passage through the column. The resulting 2-acyl lyso analogues give rise to peaks that tail in the direction of the parent intact plasmalogen. Tailing can be prevented by previous complete acid hydrolysis of plasmalogens. Direct high-performance liquid chromatographic profiling of phospholipids, their plasmalogens (as 2-acyl lyso analogues) and sphingolipids is probably the method of choice for the diagnosis of patients with deficient plasmalogen biosynthesis caused by peroxisomal abnormalities.

Chromatography, High Pressure Liquid↗
PubMed1990

An alternative hypothesis to the cause of pulpal inflammation in teeth treated with phosphoric acid on the dentin.

This paper explores the possibility that the inflammatory response in pulpal tissues noted in some early studies when dentin was treated with phosphoric acid was not caused by the acid. It suggests that the inflammatory response was caused by the prolonged exposure to zinc oxide-eugenol and documents many reports that show ZOE to be a relatively toxic material. The paper also suggests that biocompatibility studies as performed today may be inappropriate.

Acid Etching, Dental↗
PubMed1999

[Comparative study of the reactability of phosphoric acid residues in tRNA(Ser) and tRNA(Leu) from Thermus thermophilus].

The reactivity of phosphates in the Thermus thermophilus tRNA(Ser) (GCU) and tRNA(Leu) (CAG) was studied using the ethylnitrosourea modification. It was shown that phosphates of nucleotides 58-60 (T loop), 20-22 (D loop), and 48 (at the junction of the variable and T stems) were poorly modified in both tRNAs. The most pronounced differences in the reactivity were observed for phosphates at the junctions of the variable stem with T-stem (47q, 49) and anticodon stem (45). This indicates differences in orientations of the long variable arm relative to the backbone in the tRNAs studied.

Anticodon↗