Polydimethylsilane production process

FIELD: organosilicon polymers.

SUBSTANCE: polydimethylsilane is obtained by reaction of dimethyldichlorosilane with sodium at 150-170°C followed by decomposition of unreacted sodium with methyl alcohol, isolation of desired polymer, washing on filter with distilled water, drying on air and the in vacuum. Process is characterized by that sodium reagent is added as deposited on water-soluble solid, incombustible, inorganic substrate.

EFFECT: reduced fire risk of synthesis process and labor intensity of polymer isolation stage.

2 dwg, 1 tbl, 5 ex

 

The invention relates to organic chemistry, and in particular to methods of synthesis of polymer organosilanes General formula (SiR1R2)nwhere R1and R2alkyl, aryl, n>20. These compounds are used in the production of high-temperature products of silicon carbide, in the processes of microlithography as photoresists {[1]. R.West. Polysilane precursor to silicon carbide. In: Ultrastructure processing of ceramics glasses and composites. N.Y. Wiley. 1984. P.235-244; [2]. R.H.Baney. Some organometallic routes to ceramics. Ibid. P.245-255; [3] R.H.Baney. The conversion of some polyorganosilicon precursor to ceramics. In: Organosilicon and bioorganosilicon chemistry. Ed. H.Sakurai. N.Y.: Ellis Horwood Ltd., J.Wiley and Sons. 1985. P.269-274; [4] Amerlin, N.A. Popov. Ceramicbased organosilicon polymers - polycarbosilane. Overview niitekhim. Series: Organoelement compounds and their application. M: niitekhim. 1990. 58 C.; [5] M.Birot, J-P.Pillot, J.Dunogues. Comprehensive chemistry of polycarbosilanes, polysilazanes and polycarbosilazanes as precursors of ceramics // Chem. Rev. 1995. V.95. No. 5. S.1443-1477}, and in the manufacture of various modifications of silicon carbide fibers and silicon bonding, for which polydimethylsilane (PDMS) -(SiMe2n - is the basic source product. {[6] S.Yajima. Development of ceramics, especially silicon carbide fibers, from organosilicon polymers by heat treatment // Phil. Trans. R. Soc. London. A. 1980. V.294. P.419-426}.

Polydimethylsilane synthesized by the reaction of vyurts interaction clear Me2SiCl2with a dispersion of sodium in an organic dissolve the barely {[7] S.Yajima, Y.Hasegawa, J.Hayashi, .limura. Synthesis of continuous silicon carbide fibre with high tensile strength and high Young's modulus // J. Mater. Sci. 1978. V.13. P.2569-2576; [8] C.A.Burkhardt // J.Am. Chem. Soc. 1949. V.71, P.963}. As the latter is usually used toluene or xylene. Virtually unchanged this process is used until the present time for producing industrial quantities of polymer {[9] S.Yajima, T.Shishido, R.Okamura. SiC sintered Bodies with three-dimensional cross-linked polycarbosilane // Amer. Ceram. Soc. Bull. 1977. V.56. No. 12. P.1060-1063}. This method, being the closest, was selected as a prototype.

The disadvantages of this method are its high fire risk, due to a combination of finely dispersed sodium and an organic solvent, and a great complexity in the selection of the polymer is related to its swelling or dissolving in an organic solvent (In some ways instead of toluene or xylene is used by oil oil {[10] J.Heinike, R.Gobel, W.Uhlig, A.Tzschach, G.Reingold. Z.Chem. 1990. B.30. No. 5, S. 178-180}having a lower combustibility, but in this case remain the same disadvantages, namely: the swelling of the polymer, the difficulty of its extraction and purification. In addition, the petroleum oil is a combustible material). Therefore, the process of obtaining polydimethylsilane known manner, as a collection of separate, sequentially performed operations with reagents and solvents, leads to the complexity of the separation of the Oia polymer from the reaction mixture, due to its swelling in organic solvent, which affects the purity of the target product, and is associated with a high fire risk in the process.

The technical purpose of this invention is to reduce the fire risk of the process of synthesis of polymer organosilanes (polydimethylsilane), reducing the complexity of the stage of selection of the polymer while maintaining the purity of the target product.

According to the claimed invention the problem is solved by the proposed method, in which, instead of a dispersion of sodium in an organic solvent, the sodium is introduced into the reaction distributed on the surface of a solid inorganic carrier. According to the invention using anhydrous media, but has the property to dissolve in water. It is used for subsequent removal after receipt of polydimethylsilane. When using the proposed method there is no organic solvent, which reduces the Flammability of the process, facilitates the extraction of the polymer, prevents swelling or dissolving that, ultimately, gives the possibility of obtaining the target product is not contaminated by organic impurities.

The proposed method is as follows. The syntheses were carried out in a reactor equipped with a mechanical stirrer, addition funnel reverse the Odom, reflux and bubblers at the input and output. The medium was heated in an argon atmosphere to a temperature of 150-170°and was added in small portions sodium. After that, not cooling the reactor, with stirring, were added dimethyldichlorosilane (DMDCS). Despite the high temperature, condensation of the monomer in the reflux was observed. This testified to the rapid reaction. A small loss of monomer happened, according to gravimetric analysis, the output of polydimethylsilane and residual sodium (see table). After addition of the first portions of the clear mixture turns blue. Same thing, as you know {[11] R.E.Benfield, R.H.Cradd, R.G.Jones, A.C.Swain. Air-stable, alkali-metal colloids and the blue colour in Wurtz syntheses // Nature. 1991. V.353. 26 September), occurs when carrying out the reaction in organic solvents. Upon completion of addition, the clear reaction mixture was heated for 2-3 hours at 150-170°C, cooled to room temperature and was added initially methanol and then water. Salt has dissolved, the polymer was collected from the water surface, it was filtered, washed and dried.

The proposed method can be illustrated by the following examples.

Example 1. (Prototype). In a 1 liter round bottom flask equipped with a mechanical stirrer, reflux condenser and drip Raven is Oh, put 500 ml of xylene (distilled over sodium) and 82 g of sodium. The mixture was heated in a nitrogen atmosphere. Upon reaching the melting point of sodium included stirrer. The clear (200 ml) was added dropwise within 45 min, after which the mixture was heated under stirring for 10 hours, the Xylene was removed by suction through a filter formed from a blue-purple precipitate. Unreacted sodium was dissolved in methanol (600 ml). After adding 2 l of water was white powder. After 12 h, it was washed on the filter with water, with acetone, dried in air and then in vacuum for 6 h at 150°C. Received 85 g (88.7%) of polydimethylsilane in the form of a white powder, insoluble in the usual organic solvents. Found (%): 39.55; N, 9.21; Si 47.30. C2H6Si. Calculated (%): 41.32; N, 10.40; Si 48.29.

Example 2. Sodium chloride (200 g) was heated in vacuum for 3 hours at 150-200°C. In a stream of argon at 170-180°and With vigorous stirring was added in small portions 3.4 g (0.148 g-at) sodium cooled to room temperature and without stirring, was added dropwise 10 ml (10.7 g, 0.083 mol) DMDS. The mixture was painted in blue color was observed wetting of the solid phase unreacted clear, which led to difficulties in mixing. The flask was heated for 3 h at 100-120°With under reflux in an argon atmosphere, and then 5 h in vacuum at 180-200�B0; C. In a trap cooled with liquid nitrogen, gathered 0.53 ml (0.57 g, 0.0044 mole) of unreacted DMDS. The total weight of the mixture after the reaction 208.5 g, weight loss 5.6, To the reaction mass was added 5 ml of methanol, and then 500 ml of water. The polymer was washed on the filter with water until neutral, then with a small amount of methanol, dried in air and heated in a vacuum for 3 hours at 120-150°C. Obtained 2.2 g (46%) of polydimethylsilane in the form of a white hydrophobic powder. Processing of polymer toluene resulted in the separation of only small amounts (2.3%) oligomeric decylaniline (a thin layer of colorless viscous resin on the walls of the flask after removal of the toluene).

Example 3. To 5.0 g (0.22 g-at) sodium printed on 135 g of NaCl, was added dropwise in an argon atmosphere with vigorous stirring and 150-170°With 10.7 g (0.08 mole) DMDS. The mixture was painted in blue color. The stirring at 170-180°and was continued for 5 hours the Flask was heated in vacuum for 2 hours at 180°C, cooled, selected two samples (1.8-2.2 g)was dissolved into 5 ml of water and titrated with 0.1 N. H2SO4in the presence of phenolphthalein. According to the results of the two titrations determine the amount of unreacted sodium (0.057 g-at or 26% from taken in response). To the reaction mass was added 5 ml of methanol and then 500 ml of water. The polymer was filtered, washed with water, a small amount of methanol, was dried in ozdok and then in vacuum at 150° C. After drying, the polymer was treated with toluene to remove oligomeric desilylation. Obtained 4.2 g (87%) of polydimethylsilane in the form of a white hydrophobic powder. IR spectrum (liquid paraffin), (νcm-1): 1415 SL., 1250 O.S., 1075 CL., 1040 SL., 830 C., 750 O.S, 690 Wed, 625 cf. Found (%): 39.73; N, 9.35; Si 48.02. With2H6Si. Calculated (%): 41.32; N, 10.40; Si 48.29.

Example 4. Calcium chloride (115 g), pulverized in a porcelain mortar and dried in vacuum at 180-200°C, heated up to 150°and with vigorous stirring in a flow of argon was added in small portions 4.8 g (0.21 g-at) sodium, then, not cooling the flask, was added dropwise 10.7 g (0.083 mol) DMDS. Heating with stirring was continued for 3 hours, the Flask was cooled to room temperature, was added 5 ml of methanol and then 300 ml of water. The polymer was filtered, washed with water, methanol, dried in air and then in vacuum at 150°C. Obtained 4.7 g (81%) of polydimethylsilane in the form of a light gray powder.

Example 5. The reaction DMDS with sodium bicarbonate sodium.

(a) sodium Bicarbonate (103 g) was heated for 7 h in vacuum at 200 to 250°C. weight Loss through dehydration was 21, 82 g of anhydrous Na2CO3when 150-160°and With vigorous stirring in an argon atmosphere was added 8.0 g of sodium. The flask was cooled to room temperature and was added dropwise 20 ml DMDS. Nablyudenievane warming and the difficulty of mixing due to wetting of the media by the monomer. The subsequent temperature rise to 95°caused the beginning of a rapidly flowing reaction. The portion of the mixture was thrown out of the flask to the reflux condenser and a bubbler.

(b) sodium Bicarbonate (113 g), pulverized in a porcelain mortar and dried in vacuum at 270-300°C, heated up to 150°and with vigorous stirring in a flow of argon was added in small portions 3.0 g (0.13 g-at) sodium, then, not cooling the flask, was added dropwise 8.39 g (0,065 mol) DMDS. Heating at 130-140°and With intensive stirring was continued for 3 hours After cooling the flask to room temperature was added 5 ml of methanol and then 400 ml of water. The polymer was filtered, washed with water, methanol, dried, first in air, then 2 h in vacuum at 100-120°C. Received 3.69 g (98%) of polydimethylsilane in the form of a light brown powder.

(C) To 5 g of sodium deposited on 63 g of anhydrous Na2CO3was added dropwise with stirring and 150-160°With 11.3 g (0.087 mole) DMDS. The mixture was heated 2 hours at 160-170°and With stirring, then 5 hours at 180-200°without stirring in a vacuum. Condensation of volatile products in a trap cooled with liquid nitrogen was not observed. To the reaction mass was added 5 ml of methanol, and then 500 ml of water. The surface formed a viscous brown resin, the solution turned brown. The resin was washed large quantities of the m water until neutral wash water, then with acetone and dried in air. Treatment with toluene, the product was separated on a solid brown powder (1.31 g) and dark yellow baselinetobo mass (1.15 g), IR range (νcm-1): 2080 S. (Si-H), 1475 SL., 1460 SL., 1400 Wed, 1370 SL., 1250 O.S. (Si-CH3), 1070 S., 1025 O.S (Si-O-Si), 870 S., 830 O.S (Si-CH3), 750 O.S, 730 S., 690 Wed, 625 cf., 420 cf.

From the above examples it is seen that the output of polydimethylsilane was 74-87% (Examples 3, 4; table No. 2-4). The processing of toluene allows you to wash a small amount of soluble polymer, which, as can be seen from the data of IR spectroscopy (figure 1, curve 2), focus siloxane and silicon hydride groups. In polydimethylsilane they are practically absent (Fig 1, curve 1). Sodium bicarbonate was unsuccessful solid media. Obtained on the surface of the product contained a significant number of siloxane fragments (Example 5).

Data proving the effectiveness of the proposed method, shown in the table.

Table
The reaction clear with sodium on solid media
No.Taken in responseReceived
Na, g (g-at)TV. media gNa Content on the media %DMDS g (mol)Na DMDSTotal weight, gThe weight of the mixture after the reaction, gLoss weight, g(%)The polymer yield, g (%)Conversion of Na, %
13.4 (0.148)NaCl, 2001.710.7 (0.083)1.78214.1208.55.6 (2.6)2.2 (46)79
25.0 (0.220)NaCl, 1353.610.7 (0.083)2.65150.7148.22.5 (1.7)4.2 (87)73
34.8 (0.21)CaCl2, 1154.010.7 (0.083)2.53130.5125.84.7 (3.6)3.9 (81)a82
48.7 (0.378)CaCl2, 879.123.6 (0.183)2.07119.3103.515.8 (13.2)7.8 (74)b90
55.0 (0.22)Na2CO3, 637.411.3 (0.088)2.5079.374.25.1 (6.4)2.5 (49)c-
The content of the plants is oimoi faction: a15.4%;b17,9%,c53.3%.

The proposed method allows gravimetric and titrimetric control. The reaction mass after synthesis was weighed and samples were taken for acid-base titration (except holding synthesis with sodium on bicarbonate sodium, which has an alkaline nature). Knowing the mass of the initial products (solid media, sodium and clear), was determined by weight loss due to migration DMDS through the heated reactor. From the data of the titration was determined by the amount of unreacted sodium. The data are summarized in the table.

As can be seen from the obtained results, the application of the proposed method achieved the goal, namely to reduce the fire risk of the whole process is significantly simplified the procedure of selection of the target product and as a consequence obtained an additional effect is obtained polymer is not contaminated by-products of the reaction. Synthesized a way polydimethylsilane has high quality characteristics, which is confirmed by the data of elemental analysis (Example 3), IR spectroscopy (figure 1) and powder x-ray diffraction (figure 2).

The method of receiving polydimethylsilane, including a clear interaction with sodium at a temperature of 150-170°, caslogingenericsuccessview sodium methyl alcohol, the selection of the target product, washing the polymer on the filter with distilled water, drying in air and then in vacuum, characterized in that one of the reagents - sodium impose deposited on a solid non-combustible, inorganic media, soluble in water.



 

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