Nanohybrid functional separation material based on modified metal nanoparticles and method for preparation thereof

FIELD: chemistry.

SUBSTANCE: method of nanohybrid sopbent for organic substances separation is claimed. The said method includes obtaining of the metal nanoparticles adsorbed on the carrier by the way of said particles mixing with carrier, following filtration and washing and their modification with sulphur-containing organic substances (thiols and bisulphides). The obtained sopbent contains the carrier with adsorbed metal nanoparticles and ligands based on sulphur-containing organic substances covalently fixed on the surface.

EFFECT: method provides reproducible obtaining of stable sorbents allowing separation of the wide range of organic substances; enhancing of the obtained sorbents selectivity.

4 cl, 4 dwg, 7 ex

 

The invention relates to the field of organic and analytical chemistry, and materials science and can be used in chromatography for the separation of racemates of optically active compounds, and to highlight individual isomers and control enantiomeric purity (for example, amino acids, pesticides and biologically active compounds).

Known functional separation material for separating racemic mixtures obtained by immobilization by adsorption on mineral medium hydrophobic derivatives of optically active amino acids (US 4851382, B01J 20/22, 1989). As media use SiO2. The modification occurs in the dynamic mode, sequentially derived amino acids, followed by coordination of the metal ion (copper) on the surface of the carrier. Maximum selectivity factor (α) was observed when the separation of a mixture of enantiomers of glutamic acid and amounted to 1.64.

However, these sorbents are unstable in aqueous-organic and organic mobile phases, and methods for their production is quite complicated.

The closest is nanohybrid functional separation material containing gold nanoparticles obtained on inorganic media after the reduction reaction of gold salts on the pre-modified salts of tin Seeley is agile (US 6277489, 08.21.2001). The obtained gold nanoparticles attached on silica gel, initially modified by organic ligands, which are further modified with other more complex organic molecules.

Lack of sorbents is their low stability due to the absence of the covalent bond between the carrier and chiral ligands. The latter is easily washed away from the chromatographic column with an organic solvent, and therefore the column can only be used in aqueous media and to separate only water-soluble racemate, which, in turn, indicates a relatively narrow field of application of the described materials. In addition, the synthesis of these materials is a multistage process.

The present invention is to develop a stable separation of the materials, allowing the separation of a wide range of compounds, increasing their selectivity and ensuring reproducible obtain and simplifying the technology.

The problem is solved by a method of obtaining nanohybrid sorbent for the separation of organic substances, including getting adsorbed on the carrier nanoparticles of metals and their modification of sulfur-containing organic compounds, characterized in that the nanoparticles of the metal is adsorbed on the Le by mixing the solution of the above-mentioned particles with the carrier, with subsequent filtering and washing, as sulfur-containing organic compounds using thiols and disulfides.

The most stable results it shows when the sulfur compounds it contains thiols and disulfides, as well as sulfur-containing amino acids such as cysteine, and derivatives thereof.

As a carrier it can contain as organic media, such as polystyrene, and an inorganic carrier such as silica or alumina.

The highest selectivity is manifested when used as nanoparticles metal nanoparticles of gold, silver, copper or palladium.

Another aspect of the invention is a method for nanohybrid functional separation of the material described above, including the production of series-connected media, nanoparticles of metal and ligands, the novelty of which consists in the fact that pre-metal nanoparticles adsorb on the media, and then to join him ligand, a modification of their sulfur-containing organic compounds.

The implementation of the above-described sequence of operations leads to the formation of covalent bonds between the organic sulfur-containing ligand and gold nanoparticles, which significantly increases the stability of the resulting materials. This nano is astitsy metal, pre-adsorbed on the surface of the carrier, are one of the centers of interaction of enantiomers (optical isomers) and the sorbent surface, which enhances the interaction of the analyte with nanohybrid material, and, consequently, increases the retention of compounds with each other.

The technical result obtained by carrying out the present invention are:

- stability of the sorbent (in the process, the sorbent does not lose its properties);

- ease of synthesis of the sorbent (sorbent obtained in two convenient preparative stage);

commercial availability of reagents for synthesis;

- increase their selectivity (average separation factor of 1.7) and ensuring reproducible receipt.

Figure 1 shows the General scheme of fixing low molecular weight selectors media (scheme for the proposed nanohybrid material based on modified metal nanoparticles adsorbed on the surface of the carrier).

1) the media;

2) media with adsorbed metal nanoparticles;

3) media with adsorbed metal nanoparticles, modified with low molecular weight selector.

2 shows the scheme of obtaining nanohybrid material based on modified gold nanoparticles adsorbed on top of the spine of silicon oxide (a), the image of the surface of silicon oxide with adsorbed gold nanoparticles obtained by the method of transmission electron microscopy (TEM) (b).

Figure 3 shows a chromatogram of racemic mixtures of fenoprofen. Column 100×4,6. Mobile phase: hexane/isopropanol (70/30). The flow rate of 2 ml/min, λ=254 nm.

Figure 4 shows the chromatogram of racemic mixtures of pindolol. Column 150×4,6. Mobile phase: acetonitrile/methanol/acetic acid/triethylamine (60/40/0,2/0,2). The flow rate of 2 ml/min, λ=230 nm.

The following examples illustrate, but do not exhaust the invention.

Example 1. The method of obtaining modified alumina

Receiving the modified alumina was carried out according to the scheme shown in figure 1. A portion of the alumina (2 g) (media) with a particle diameter of 10-40 μm suspension in 20 ml of a solution of gold nanoparticles with slow stirring (30-40 rpm) on a magnetic stirrer at room temperature. The mixture is stirred for 1 hour, filtered and washed successively with water and ethyl alcohol, and thus, the aluminum oxide with adsorbed gold nanoparticles. In another flask was placed a solution of sulfur-containing organic compounds, which is an amino acid belonging to the group of thiols, which was taken L-cysteine (10-3M,25 ml), in water and modify them obtained alumina with adsorbed gold nanoparticles, for which the mixture is stirred for 1 hour, filtered, washed with water and alcohol. The result of nanohybrid functional separation material containing as a carrier of aluminum oxide with adsorbed gold nanoparticles that are covalently attached ligands based on sulfur-containing organic compounds, which is an amino acid belonging to the group of thiols, - L-cysteine.

The obtained sorbent fill chromatographic column 4.6×150 mm under a pressure of 200-300 Bar. The separation of the sorbents modified received nanohybrid functional separation material is carried out in a nonaqueous mobile phases, i.e. in the normal phase and polar organic options chromatography. Thus, the authors were able to find a new and convenient way of surface modification of aluminum oxide, which is superior to previously described for ease of preparation, stability and commercial availability.

The pindolol enantiomers were separated on a column of aluminum oxide and 4.6×150 mm) in polar organic version HPLC using mobile phase acetonitrile/methanol and addition of acetic acid and triethylamine (60/40/0,2/0,2), flow rate 2 ml/min the retention Time of the first and the Omer t R1'=2,75, the second tR2'=3,32. The coefficient of the selectivity of separation α=1,21. The repetition of the analysis of the sorbent did not lose their chromatographic properties. Detection was performed by the spectrophotometric detector at a wavelength of 230 nm.

Example 2. The method of obtaining modified silicon oxide

Receiving the modified silica was carried out according to the scheme shown in figure 1. A portion of silicon oxide (2 g) with a particle diameter of 5 μm suspension in 20 ml of a solution of gold nanoparticles with slow stirring (30-40 rpm) on a magnetic stirrer at room temperature. The mixture is stirred for 1 hour, filtered and washed successively with water and ethyl alcohol. In another flask was placed a solution of sulfur-containing organic compounds, which is an amino acid belonging to the group of thiols, - L-cysteine (10-3M, 25 ml), water and a modified silicon oxide, the mixture is stirred for 1 hour, filtered, washed with water and alcohol. The result of nanohybrid functional separation material containing as a carrier silica with adsorbed gold nanoparticles that are covalently attached ligands based on sulfur-containing organic compounds, which is an amino acid belonging to the group of thiols, - L-cysteine (figure 2).

Obtained the sorbent fill chromatographic column 4.6×150 mm and 4.6×100 mm under a pressure of 200-300 Bar. The separation of the sorbents modified with low molecular weight selector is carried out in a nonaqueous mobile phases, i.e. in the normal phase and polar organic options chromatography (figure 3 and figure 4). The enantiomers of fenoprofen were separated on a column of 4.6×100 mm) with silica gel in normal-phase variant HPLC using a mobile phase of hexane/isopropanol (70/30), flow rate 2 ml/min the retention Time of the first isomer tR1'=1,05, the second tR2'=1,79. The coefficient of the selectivity of separation α=1,7. The repetition of the analysis of the sorbent did not lose their chromatographic properties. Detection was performed by the spectrophotometric detector at a wavelength of 254 nm. The pindolol enantiomers were separated on a column of silica gel (to 4.6×150 mm) in polar organic version HPLC using mobile phase acetonitrile/methanol and addition of acetic acid and triethylamine (60/40/0,2/0,2), flow rate 2 ml/min the retention Time of the first isomer tR1'=1,58, the second tR2'=1,82. The coefficient of the selectivity of separation α=1,15. The repetition of the analysis of the sorbent did not lose their chromatographic properties. Detection was performed by the spectrophotometric detector at a wavelength of 230 nm.

Example 3. The method of obtaining modified silicon oxide

Receiving the modified silicon oxide is carried out according to the scheme, presented in figure 1. A portion of silicon oxide (2 g) with a particle diameter of 5 μm suspension in 20 ml of a solution of copper nanoparticles with slow stirring (30-40 rpm) on a magnetic stirrer at room temperature. The mixture is stirred for 1 hour, filtered and washed successively with water and ethyl alcohol. In another flask was placed a solution of sulfur-containing organic compounds, which is an amino acid belonging to the group of thiols, - L-cysteine (10-3M, 25 ml), water and a modified silicon oxide, the mixture is stirred for 1 hour, filtered, washed with water and alcohol. The result of nanohybrid functional separation material containing as a carrier silica with adsorbed nanoparticles of copper, which is covalently attached ligands based on sulfur-containing organic compounds, which is an amino acid belonging to the group of thiols, - L-cysteine.

Example 4. The method of obtaining modified silicon oxide

Receiving the modified silica was carried out according to the scheme shown in figure 1. A portion of silicon oxide (2 g) with a particle diameter of 5 μm suspension in 20 ml of a solution of silver nanoparticles with slow stirring (30-40 rpm) on a magnetic stirrer at room temperature. The mixture is stirred for 1 hour, filtered and washed with n is therefore water and ethyl alcohol. In another flask was placed a solution of sulfur-containing organic compounds, which is an amino acid belonging to the group of thiols, - L-cysteine (10-3M, 25 ml), water and a modified silicon oxide, the mixture is stirred for 1 hour, filtered, washed with water and alcohol. The result of nanohybrid functional separation material containing as a carrier silica with adsorbed silver nanoparticles that are covalently attached ligands based on sulfur-containing organic compounds from the group of thiols, - L-cysteine.

Example 5. The method of obtaining modified silicon oxide

Receiving the modified silica was carried out according to the scheme shown in figure 1. A portion of silicon oxide (2 g) with a particle diameter of 5 μm suspension in 20 ml of a solution of palladium nanoparticles with slow stirring (30-40 rpm) on a magnetic stirrer at room temperature. The mixture is stirred for 1 hour, filtered and washed successively with water and ethyl alcohol. In another flask was placed a solution of sulfur-containing organic compounds, which is an amino acid belonging to the group of thiols, - L-cysteine (10-3M, 25 ml), water and a modified silicon oxide, the mixture is stirred for 1 hour, filtered, washed with water and alcohol. The result of nanohybrid F. the purpose ground receiving stations separation material, contains as a carrier silica with adsorbed palladium nanoparticles that are covalently attached ligands based on sulfur-containing organic compounds, which is an amino acid belonging to the group of thiols, - L-cysteine.

Similarly, were obtained nanohybrid functional separation materials containing as a carrier of aluminum oxide with adsorbed nanoparticles of silver, copper, palladium, which covalently attached ligands based on sulfur-containing organic compounds.

Example 6. The method of obtaining modified polystyrene

Receiving modified polystyrene was carried out according to the scheme shown in figure 1. A portion of the polystyrene (2 g) with a particle diameter of 5 μm suspension in 20 ml of a solution of gold nanoparticles with slow stirring (30-40 rpm) on a magnetic stirrer at room temperature. The mixture is stirred for 1 hour, filtered and washed successively with water and ethyl alcohol. The result of nanohybrid functional separation material containing as a carrier polystyrene with adsorbed gold nanoparticles that are covalently attached ligands based on sulfur-containing organic compounds, which is an amino acid belonging to the group of thiols, - L-cysteine.

Example 7. The method of obtaining modified silicon oxide

Receiving the modified silica was carried out according to the scheme shown in figure 1. A portion of silicon oxide (2 g) with a particle diameter of 5 μm suspension in 20 ml of a solution of gold nanoparticles with slow stirring (30-40 rpm) on a magnetic stirrer at room temperature. The mixture is stirred for 1 hour, filtered and washed successively with water and ethyl alcohol. In another flask was placed a solution of sulfur-containing organic compounds, which is an amino acid belonging to the group of thiols, - L-group probably facilitates (10-3M, 25 ml), water and a modified silicon oxide, the mixture is stirred for 1 hour, filtered, washed with water and alcohol. The result of nanohybrid functional separation material containing as a carrier silica with adsorbed gold nanoparticles that are covalently attached ligands based on sulfur-containing organic compounds from the group of disulfide - group probably facilitates.

Thus, a stable separation materials, allowing the separation of a wide range of compounds, including the separation of isomers of optically active compounds, in particular related to the class of N-hydroxypropylamino (β-blockers), profenov, widely used in f is rmacology and medicine.

Developed a method of producing sorbents to ensure its obtaining reproducible and simplification of the technology, allowing to greatly reduce the time and cost of synthesis of sorbents.

1. The method of obtaining nanohybrid sorbent for the separation of organic substances, including getting adsorbed on the carrier nanoparticles of metals and their modification of sulfur-containing organic compounds, characterized in that the metal nanoparticles adsorb on the media by mixing the solution of the above-mentioned particles with the carrier followed by filtration and washing, as sulfur-containing organic compounds using thiols and disulfides.

2. The method according to claim 1, wherein the carrier is selected from a range of: silicon oxide, aluminum oxide, polystyrene.

3. The method according to claim 1, characterized in that the nanoparticles are selected from a number of: gold, silver, copper.

4. Nanohybrid sorbent for the separation of organic substances containing media with adsorbed nanoparticles of metal and covalently attached to the nanoparticles sulfur-containing ligands, characterized in that it is obtained by the method described in claim 1.



 

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3 tbl

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