The method of obtaining salts triarylmethyl cations with organoboron anion

 

(57) Abstract:

The invention relates to a method for producing salts consisting of a bulky organic cation and bulk organic anion, specifically salts triarylmethyl cations with organoboron anion. These compounds are widely used as components of highly efficient catalytic systems for obtaining polyolefins, including in large-tonnage production. Describes how to obtain salts triarylmethyl cations with organoboron anion of General formula [Ar3S][BAr4], where Ar is aryl organic radicals, the interaction of triarylmethane with alkaline salts boron anions, which are used in the form of solid substances and the process is carried out by mechanical treatment of the mixture of reagents, taken in stoichiometric amounts, in the absence of solvent, followed by separation of the target product. The technical result is the ability to use readily available source reagents, highly effective, safe and fast to process with a high yield of the target product.

The invention relates to a method for producing salts consisting of voluminous, organic imennyh in the aryl radicals derived from tetraarylborates anions, in particular fluorinated tetraarylborates anions, such as tetrakis(pentafluorophenyl)borate.

These compounds are widely used as components of highly efficient catalytic systems for obtaining polyolefins, including in large-tonnage production of [European patent 0277003, 1988. European patent 0277004, 1988. Yang X., Stern, S. L., Marks T., J. J. Am. Chem. Soc. 1991. 113. 3623. European patent 0427697, 1991].

These compounds get the exchange interaction solutions tailored salts triarylmethyl cation and a boron-containing anion in organic solvents. A special selection of original substances, solvents, increasing the duration of the reaction and holding it at the boiling temperature of the solvent is possible to shift the reaction towards formation of the target product. After the process is complete, the product is separated and purified by recrystallization from a suitable solvent [Bahr S. R., P. Boudjouk Journal of Organic Chemistry. 1992. 57(20). 5545-5547. Brauer D. J., Burger H. et al. Zeitschrift fur anorganische und allgemeine Chemic. 2001. 627(4). 679-686. Frohn N. J., Franke N. et al. Journal of Organometallic Chemistry. 2000. 598(1). 127-135].

Methods of synthesis of performerov were first systematized by Massey and Park [Massey, A. G., Park, A. J. Journal of Organometallic Ch triphenylmethylchloride(pentafluorobenzoate), RH3ST(C6F5)4[King R. C. Organometallic Synthesis, 1986. V. 3].

The most frequently synthesis through advanced education pentafluoroaniline alkali metal salts by reaction alkylate or Grignard reagent with pentafluorobenzyl, the subsequent exchange reaction with trichlorophenol in diethyl ether and further prolonged boiling with triphenylmethanol environment aliphatic solvents [Chien, J. C. W., Tsai, W. M., Rausch, M. D. J. Am. Chem. Soc. 1991. 113. 8570. U.S. patent 5493056, 1996. U.S. patent 6096928, 2000. U.S. patent 6231790, 2001. European patent 505972, 1992. European patent 604961, 1994. International patent WO 9400459, 1994]. After the process is finished, the product contained in the sludge separates and is recrystallized from a mixture of methylene chloride-hexane.

It should be noted the General disadvantages of methods of synthesis in solvents on these schemes. It is noted that operations solution LiC6F5required when the temperature is S. But at this temperature they are unsafe, because the reaction mixture is often unpredictable exploded [Chen Y.-H., Metz, M. V., Li, L., Stern, C. L., Marks T. J. J. Am. Chem. Soc. 1998. 120. 6287]. Reactions in solvents is a multistage process, the first stage of which is a long, zavershennosti each stage does not have clear criteria. Also essential is the complexity of selection and low yields of the target product.

Closest to the proposed method is a synthesis of Ph3CB(C6F5)4boiling LiB(C6F5)4with an excess of RH3CCl in hexane for 12 hours, followed by the separation of sludge and recrystallization him from a mixture of methylene chloride - hexane. Output Ph3CB(C6F5)4was 64% [Chien, J. C. W., Tsai, W. M., Rausch, M. D. J. Am.Chem.Soc. 1991. 113. 8570] - (prototype).

This method has the following disadvantages: large duration of the process, the necessity of using large amounts of different solvents, which, among other things, affects the environmental performance of the process.

The task of the invention is the synthesis of salts triarylmethyl cations with organoboron anion of General formula [AG3S][bar’4], where Ar is aryl organic radicals, such as phenyl, pentafluorophenyl.

The problem is solved in the proposed method, the interaction of triarylmethane with alkaline salts boron anions. The process is carried out by mechanical treatment of a mixture of solid source reagents, taken in stagione is similar reagents are taken in stoichiometric quantity. The process is carried out without solvent under mechanical activation of the reaction mixture. Control over the course of the reaction is carried out by changing the color of the reaction mixture (from white to orange). The mixture may contain ballast substances, such as halides of alkali metals, which do not interfere with the reaction, but can be contained within the original substances from which they are difficult to separate.

In the present invention, the reaction mixture is subjected to mechanical processing. As a device for machining can be used vibratory mill with grinding media balls, or a planetary mill, or a special device for grinding, in which the reactor describes a complicated trajectory, type “drunken barrel” [K. G. Myakishev, centuries wolves. Vibratory mill-activator of mechanochemical reactions. Preprint No. 89-12 Institute of inorganic chemistry, USSR Academy of Sciences, Novosibirsk. 1989; E. G. Avvakumov. Mechanical methods of activation of chemical processes. Novosibirsk. “Science”. 1979].

The method of obtaining salts triarylmethyl cations with organoboron anion set forth in the examples below. In the examples, the inventive method was carried out by conducting the reaction in a metal hermetically allicance balls as a trigger nozzle (grinding media). The reaction mixture was subjected to mechanical stress vibration ball mill (vibration with a frequency of 12 Hz and an amplitude of 11 mm) for 1-2 hours. After machining, the reaction mixture consisted of a bright orange powder (educt - white) and consisted of a halide of an alkali metal (according to x-ray phase analysis) and the target product. The target product was recovered by treating the reaction mixture with a suitable solvent (methylene chloride, acetonitrile). The solution was filtered, concentrated to a small volume of hexane was added and left for a few hours (usually at night) for crystallization of the desired product. The resulting borate crystals were separated, washed with hexane and dried in vacuum. All loading operations of the reactor and the separation of the product were carried out in an inert atmosphere.

Claimed in the invention the solid phase, without solvent, mechanochemical method of obtaining salts triarylmethyl cations with organoboron anion allows the use of readily available source reagents, highly effective, safe and fast to process with a high yield of the target product.

Thus, the analysis is degenova technical solution meets the criteria of novelty and inventive step.

The inventive method of obtaining salts triarylmethyl cations with organoboron anion illustrated in the following examples.

Examples

Synthesis of the starting compounds.

RH3CCl and Ph3CBr was obtained by conventional methods [Agronomos A. E., Zapryagaev Y. C. Laboratory work in organic workshop. Ed. 2-E. M.: Chemistry. 1974. S. 176. General workshop on organic chemistry (Organikum). M: Peace. 1965. S. 303].

Getting alkaline salts of borate anions

The mixture LiB(C6F5)4+ 3LiCI was obtained by interaction of n-utility with the stoichiometric quantity C6F5Br in hexane, followed by processing a mixture of chloride of boron at-80C [Massey, A. G., Park, A. J. Journal of Organometallic Chemistry. 1964. 2. 245]:

C4H9Li+C6F5BrC6F5Li+C4H9VG

4C6F5Li+l3LiB(C6F5)4+3LiCl.

The precipitate was separated and used in the reactions.

NaB(C6F5)4received by the Grignard reaction of C6F5Br, magnesium and readily available non-volatile boron reagent - tetrafluoroborate sodium [Bahr S. R., P. Boudjouk Journal of Organic Chemistry. 1992. 57 (20). 5545-5547]:

C6FKB(C6F5)4was obtained by precipitation from aqueous lithium or sodium salt of the anion B(C6F5)-4the action of an aqueous solution of potassium chloride:

NaB(C6F5)4+lKB(C6F5)4+NaCl

NaB(C6H5)4- commercial product (VEB JENAPHARM-LABORCHEMIE APOLDA, “analytical grade”) is used without further purification.

According to our proposed method uses the available source materials - commercial or easily synthesized triphenylmethane or triphenylmethane and alkali metal salts of the anion VG-4. Note that is well suited for this reaction, potassium salt, which is stable, nephroscopy and obtained from other salts by precipitation from aqueous solutions of potassium ion. Deposition of tetraphenylborate potassium from aqueous solutions is a quantitative analytical response to potassium, as derived from fluorinated aryl radicals even more stable.

Example 1 (on prototype, conducting the reaction in solution [Chien, J. C. W., Tsai, W. M., Rausch, M. D. J. Am.Chem.Soc. 1991. 113. 8570]).

A mixture of 2.6 g LiB(C6F5)4(3,79 mmole) and 1.8 g of RH3CCl (6,46 mmole) was boiled in 200 ml of hexane for 12 hours. Postmenopausal hexane (2 x 20 ml) and dried in vacuum. The resulting product was recrystallized from a mixture of methylene chloride - hexane. Received RH3ST(C6F5)4in the form of orange crystals. Yield 1.7 g(47%). (48,6%).

Example 2 (for comparison, claimed in the invention method with the method of the prototype in Example 1).

The mixture of solids (LiB(C6F5)4+3LiCl) containing 1,03 g LiB(C6F5)4(1.50 mmol), 0,42 g RH3Cl (1.50 mmol) and 20 steel balls with a diameter of 7.3 mm (total weight ~150 g) were loaded into steel hermetic reactor volume of ~80 cm3. The reactor was mounted on a vibration ball mill and the reaction mixture was subjected to mechanical stress (vibration with a frequency of 12 Hz and an amplitude of 11 mm) for 1 hour. After termination of the machining reaction mixture is original white substances turned into a bright orange powder. The powder was transferred into a vessel Slanka. The reactor and steel balls washed with methylene chloride (3 times 20 ml). The resulting solution was transferred into a vessel Slence with powder products of the reaction. The solution was filtered through a thick glass filter. The filtrate was concentrated to a volume of ~5 ml To the obtained concentrated solution of the desired product in chloride m is high and the crystals RH3ST(C6F5)4was separated from the solution by filtration, dried in vacuum. Output RH3ST(C6F5)40.85 g (61%).

Analysis.

Found, %: N 1,72; 53,48; F 41,29.

Calculated for RH3ST(C6F5)4, %: N 1,64; 55,99; F 41,19.

Thus, the proposed method is possible using the reaction mixture containing ballast substances (LiCl).

Example 3 (for comparison claimed in the invention method with the method of the prototype in Example 1 and the possibility of using other starting substances for comparison with Example 2).

The reaction was conducted and the product was isolated as described in example 2. Mechanical treatment within 2 hours was subjected to a mixture KB(C6F5)4(1.20 g, 1,67 mmole) and RH3CCl (0,47 g, was 1.69 mmol). After extraction and crystallization got to 1.15 g of RH3ST(C6F5)4in the form of orange crystals. A yield of 75%.

Thus, in the solid-phase reaction, in contrast to the prototype can be used as the initial substance potassium salt borate anion. Comparison with Example 2 shows that as the source reagent may be used potassium salt of the prototype in Example 1 and the possibility of using other starting substances for comparison with Examples 2, 3).

The reaction was conducted and the product was isolated as described in example 2. Mechanical treatment for 1 hour and subjected the mixture KV(C6F5)4(0,91 g of 1.27 mmole) and RH3CSAs (0,41 g of 1.27 mmol). After extraction of the reaction mixture and crystallization of the product was obtained 0.95 g of RH3ST(C6F5)4. Yield 81%.

This example shows the possibility of using as a source not of chloride and bromide triphenylmethane.

Example 5 (comparison claimed in the invention method with the method of the prototype in Example 1 and the possibility of using non-fluorinated borate anions for comparison with Examples 1-4).

The reaction was carried out as described in example 2. Mechanical treatment for 1 hour and subjected to a mixture of white original substances NaBPh4(1.10 g, is 3.21 mmol) and RH3CCl (0,90 g of 3.23 mmol). Received red-brown free-flowing powder composed of a mixture of RH3Ph4and NaCl. Individual products from the mixture obtained was not allocated because when dissolved they quickly decompose and discolor.

This example shows the possibility of applying the proposed method to obtain triarylmethane derivatives neftali solid phase, without solvent, mechanochemical method of obtaining salts triarylmethyl cations with organoboron anion allows the use of readily available source reagents, highly effective, safe and fast to process with a high yield of the target product.

The method of obtaining salts triarylmethyl cations with organoboron anion of General formula [AG3With][Vah4], where Ar is aryl organic radicals, the interaction of triarylmethane with the alkaline salts of organoboron anion, characterized in that the starting reagents used in the form of solids and the process is carried out by mechanical treatment of the mixture of reagents, taken in stoichiometric amounts, in the absence of solvent, followed by separation of the target product.

 

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