Inclusion complex of elemental sulfur with cyclodextrin

FIELD: chemical technology.

SUBSTANCE: invention relates to the inclusion complex of cyclodextrins with elemental sulfur. Complex can be prepared using different homologues of cyclodextrins, for example, beta- and gamma-cyclodextrins and hydroxypropylated forms of gamma- and beta-cyclodextrins. Proposed complex can be used as a biologically active compound for medicinal, veterinary and agricultural designation. Invention provides the possibility for further preparing true solutions of elemental sulfur in water in the concentration up to 250-300 mg/l.

EFFECT: improved preparing method, valuable properties of complex.

7 cl, 7 ex

 

The invention relates to the development of biologically active compounds of medical, veterinary and agricultural purposes. In particular, the invention relates to the development of a complex of cyclodextrin with elemental sulfur.

The biological activity of elemental sulfur are well known and this substance is used in medicine for the treatment of skin diseases, as antiparasitic and microbicide funds and as distributed, stimulating metabolism [1]. Elemental sulfur is also used in agriculture as a means of protection of plants, as a fungicide and acaricide [2].

Elemental sulfur is practically insoluble in water, even boiling, but, nevertheless, its distinct physiological effects on living systems is manifested in the result of the impact of trace amounts of a substance that still fall into the surrounding aqueous solution when in contact with particles of sulfur. Thus, even very low concentrations of elemental sulfur effect on living cells and organisms of the target.

When using sulfur as a means of microbicide use various forms of dispersed sulfur, such as sulfur ground. In agricultural practice is also used colloidal sulfur in the form of specially prepared preparative forms containing surface is active and wetting agents, when the preparation is diluted with water. In medical practice are used sulfuric color, purified sulphur and sulphuric milk (colloidal sulphur) [1].

Suspension of sulfur to obtain colloidal solutions stabilize various additives, such as inorganic calcium polysulfides, polyalcohol (ethylene glycol, glycerol, pentaerythritol) and nonionic surface-active polymers [3]. Obtained by the use of polysulfides suspensions or colloidal solutions of elemental sulfur in water have a high alkalinity, which excludes the possibility of their application in medical and veterinary purposes. Despite the fact that the discussed form of sulfur is indicated by "water-soluble form of elemental sulfur", the composition is only stable colloidal solution of sulfur in the water, not true, that is detected by the Tyndall effect.

The task, which was sent to the claimed invention was to develop complexes of cyclodextrins with elemental sulfur, presumably with the true solubility in water.

The task was solved by the synthesis of previously unknown molecular inclusion complexes of type "guest-host" between elemental sulfur and cyclodextrins. Synthesis of new cyclodextrins complexes are widely used for Uwe is icene true solubility of hydrophobic organic substances in water. However, from literature it is known that cyclodextrins are not well suited for obtaining complexes with inorganic compounds [4]. As exceptions to this rule can be called only the inclusion complexes of cyclodextrins with some inorganic acids (HCl, HJ, HBr, H2PO4) [5], cations of some metals (Cu, Ag) [6], as well as a number of elements of the periodic table: metal iodine [7], gaseous krypton, xenon [7] and radon [8]. The inclusion complexes of cyclodextrins with other elements, and in particular with elemental sulfur, still no one described.

Unexpectedly found that elemental sulfur forms a stable crystalline inclusion complexes with cyclodextrins. Not wishing to be bound by any theory, the authors, however, believe that as a result of interaction with a hydrophobic cyclodextrin molecules of elemental sulfur latter penetrate into the cavity of the molecules of cyclic oligosaccharides. When the polar solvent is surrounded by hydrophobic molecules sulfur shielded carbohydrate ring of residues α-D-glucopyranose residues. In the complexation does not occur chemical (ionic and covalent) bond between the molecule-guest (elemental sulfur) and molecule-master (cyclodextrin), and the resulting clathrate, being rastvorennye suspended in water, easily gives "enabled connection, transferring it into the solution, and then the object of biological effects (cell, organism). Thus, the biological properties of the complex, which clathrate cyclodextrin derivative and sulfur are determined primarily by the properties of elemental sulfur.

The technical result, which can be obtained by carrying out the invention lies in the possibility of inclusion complexes of cyclodextrins with elemental sulfur in a stable powdered crystalline or amorphous products, partially or completely soluble in water.

Embodiments of the present invention are as follows.

The inclusion complex of elemental sulfur with cyclodextrin or its derivatives, including elemental sulfur and the cyclodextrin or cyclodextrin derivative, and the molar ratio of sulfur to the cyclodextrin or cyclodextrin derivative in the complex is the ratio of 1:0.5 to÷20.

Elemental sulfur, above, presented allotropic modifications of sulfur with the number 6 or 8 sulfur atoms in the molecule.

Cyclodextrin mentioned above, selected from the group consisting of beta-cyclodextrin and gamma-cyclodextrin.

Derivatives of cyclodextrin mentioned above, selected from the group consisting of hydroxypropyl-beta-Cyclades is Rina and hydroxypropyl-gamma-cyclodextrin.

The technical result that can be achieved by carrying out the invention, is the ability to obtain a crystalline sulfur complexes with cyclodextrins, which allows to prepare the true solution of elemental sulfur in the water.

To explain the present invention presents the following examples, but it is assumed that they do not limit the scope of the claims of the present invention.

Example 1. Obtaining a crystal of a complex of sulfur in the solution of beta-cyclodextrin and sodium thiosulfate in the formation of elemental sulfur in it in the decay of sodium thiosulfate occurring from exposure to hydrochloric acid.

A portion of 7.5 g of crystalline beta-cyclodextrin and a portion 15 g of sodium thiosulfate pentahydrate is dissolved in 500 ml of distilled water. In the resulting solution for 15 to 20 minutes evenly contribute to 10.5 ml of 10%hydrochloric acid, portions 250-500 µl, with active stirring. The formation of the inclusion complex of sulfur with beta-cyclodextrin shows the formation of crystalline brick-red precipitate.

The reaction mixture is neutralized ˜6 ml of 10%sodium hydroxide until neutral pH and kept in the refrigerator at +5-10°With five or six hours.

The precipitate of complex inclusions of elemental sulfur with beta-cyclodextrin is separated filtered is eat or centrifugation, rinse with acetone and dried in air at 50°With within 24 hours.

The output of the complex is 6.68 grams.

Method elemental microanalysis shows that the mass percentage of the elements in the complex (S):():(H):()=14,44:37,08:5,66:42,82, which corresponds to the empirical formula of the complex (beta-cyclodextrin)*S6*H2O. the Molar ratio of sulfur to the cyclodextrin complex is equal to 1:1.

Example 2. Obtaining crystalline complex in the solution of gamma-cyclodextrin in the formation of elemental sulfur in it, originating in the decay of sodium thiosulfate from exposure to hydrochloric acid.

The portion 15 g of crystalline gamma-cyclodextrin and a portion of 30 g of sodium thiosulfate pentahydrate is dissolved in 500 ml of distilled water. In the resulting solution for 15 to 20 minutes evenly contribute to 21.4 ml of 10%hydrochloric acid, portions of 500 ál with active stirring. The formation of the inclusion complex of sulfur with gamma-cyclodextrin shows the appearance of a white crystalline precipitate, suspended in the suspension. The reaction mixture is neutralized ˜6 ml of 10%sodium hydroxide solution to a normal pH and kept in the refrigerator at +5-10°With five or six hours.

The precipitate obtained complex of elemental sulfur with gamma-cyclodextrin is separated f is trovanjem or centrifugation, rinse with acetone, dried in air at 50°within 24 hours, and then weighed. The mass of the obtained complex include approximately 10.2 grams.

Method elemental microanalysis shows that the weight percentage of the elements in the complex (S):():(H):()=14,07:31,62:6,08:48,24, which corresponds to the empirical formula of the complex (gamma-CD)*S8*H2O. the Molar ratio of sulfur to the cyclodextrin complex is equal to 1:1.

Example 3. Obtaining crystalline complex of beta-cyclodextrin and elemental sulfur added in the form of an acetone solution.

A portion of 5 g of crystalline beta-cyclodextrin is dissolved in 500 ml of distilled water. In the resulting solution for 15 to 20 minutes to evenly make ˜100 ml solution of elemental sulfur in boiling acetone with a concentration of ˜0.2 wt.%. The formation of the inclusion complex of sulfur with beta-cyclodextrin shows the appearance of a white crystalline precipitate, suspended in the suspension, which is filtered or separated by centrifugation, and then dried at 50°C. the Weight of the obtained complex is 2.4 grams

The weight percentage of the elements in the complex, certain methods of weight microanalysis: (S):():(H):()=7,81:40,98:5,73:45,47, which corresponds to the empirical formula of the complex [2*beta-CD]*[S6/sub> ]. The molar ratio of sulfur to the cyclodextrin complex is equal to 1:0.5 in.

Example 4. Obtaining crystalline complex in the solution of gamma-cyclodextrin by adding elemental sulfur dissolved in acetone.

A portion of 10 g of crystalline gamma-cyclodextrin are dissolved in 500 ml of distilled water. In the resulting solution for 15 to 20 minutes to evenly make ˜150 ml of a solution of elemental sulfur in boiling acetone (˜0.2 wt.%). The inclusion complex of sulfur with gamma-cyclodextrin is formed in the form of a white crystalline precipitate, suspended in the suspension, which is separated by filtration or centrifugation, and then dried at 50°C. the Weight of the obtained complex is ˜1.61 grams.

The weight percentage of the elements in the complex, certain methods of weight microanalysis: (S):():(H):()=17,47:35,42:5,45:41,66, which corresponds to the empirical formula of the complex [gamma-CD]*[S8]. The molar ratio of sulfur to the cyclodextrin complex is equal to 1:1.

Example 5. Obtaining water-soluble dry complex of elemental sulfur with hydroxypropyl beta-cyclodextrin.

To 100 ml of a solution containing 4.0 g hydroxypropyl beta-cyclodextrin with a degree of substitution 5.5 add 4 ml of aqueous suspension containing 40 mg of sulfur, and stirred for 2 hours at room is temperature, then the obtained clear solution is freeze-dried. The mass of the obtained product, completely soluble in 100 ml of water containing 0.1 wt.% elemental sulfur in complex with hydroxypropyl beta-cyclodextrin is Android 4.04 grams. The molar ratio of elemental sulfur to hydroxypropylamino derived cyclodextrin in the resulting complex is the value of ˜1:20.

Example 6. Illustrates the possibility of obtaining complex gamma-cyclodextrin and elemental sulfur in the reaction mechanochemical transformations.

The hinge 10 grams gamma-cyclodextrin pound in a mortar with 0.2 grams of crystalline sulfur. The mixture is transferred into the chamber of the vibration of the colloid mill, moistened with 0.5 ml of water and subjected to homogenization in 24-48 hours, after dried in the air. In the process of mechanochemical reactions of gamma-cyclodextrin with crystal grey color of the mixture changed from yellow to almost white. The sulfur content in the resulting complex is ˜2 wt.% The molar ratio of elemental sulfur to gamma cyclodextrin complex is the value of ˜1:10. The molar ratio of elemental sulfur to gamma cyclodextrin complex is the value of ˜1:10.

Example 7. Illustrates the possibility of obtaining complex hydroxypropyl gamma-cyclodextrin with a degree Zam the assumptions 3.5 and sulfur in the reaction ultrasonic processing.

The hinge 5 grams of hydroxypropyl gamma-cyclodextrin with a degree of substitution 3.5 dissolved in 50 ml water and make up to the same 50 mg drug fine sulfur suspended in 5 ml of water. The resulting mixture was subjected to ultrasonic treatment at room temperature to obtain a clear solution, which is freeze-dried.

The molar ratio of elemental sulfur to gamma cyclodextrin complex is the value of ˜1:20.

Bibliography

1. Chemical encyclopedia. Article Sulfur. - M.: Soviet encyclopedia, 1990, volume 4, page 319.

2. Iveren, Nmodern, Raguenaud etc. Handbook for the protection of forests from pests disease. - M.: Forest industry, 1980, 376 S.

3. Preparative form water-soluble elemental sulfur to protect cultivated plants from pests. Patent of Russia №2142908 IPC SW 17/43.

4. Jozef Szeitli. Cyclodextrin Technology, ed. Kluwer Acad Publishers, 450 p.

5. The method of obtaining inclusion complexes of cyclodextrins. Patent USSR SU # 1269738 (A3), IPC SW 37/16.

6. Fcrmer. Connections include, trans. from German, M. Publishing house of foreign literature, 1958, 169 S.

7. F.Cramer, F.M.Heng Lein. "Chemische Berichte", v.90, p.2572, 1957.

8. Radon concentrate. Patent of Russia №2051689, IPC AC 51/02.

1. The inclusion complex of elemental sulfur with cyclodextrin or cyclodextrin derivatives containing elemental sulfur is a cyclodextrin or cyclodextrin derivative, moreover, the molar ratio of sulfur to the cyclodextrin or cyclodextrin derivative in the complex is in the range of 1:0.5 to÷20.

2. The complex of elemental sulfur with a cyclodextrin according to claim 1, where the specified elemental sulfur presents allotropic modifications to the number of sulfur atoms in the molecule in the range of from six to eight.

3. The complex of elemental sulfur with a cyclodextrin according to claim 1 or 2 where the specified elemental sulfur is preferably presents allotropic modification of S8.

4. The complex of elemental sulfur with a cyclodextrin according to claim 1, where the specified cyclodextrin beta-cyclodextrin.

5. The complex of elemental sulfur with a cyclodextrin according to claim 1, where the specified cyclodextrin represented by gamma-cyclodextrin.

6. The sulfur complex with cyclodextrin or cyclodextrin derivatives according to claim 1, where the specified cyclodextrin derivative represented by hydroxypropyl-beta-cyclodextrin.

7. The sulfur complex with cyclodextrin or cyclodextrin derivatives according to claim 1, where the specified cyclodextrin derivative represented hydroxypropyl-gamma-cyclodextrin.



 

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