Method of production of the bromine derivatives of the fullerene c60

FIELD: chemical industry; methods of production of the bromine derivatives of fullerene С60.

SUBSTANCE: the invention is pertaining to the method of production of the bromine derivatives of fullerene С60. The process consists in the interaction of the bromoform and the tetra bromomethane with fullerene С60 at presence of the rhodium-containing catalyst - Wilkinson's complex [RhCl(PPh3)3] at the temperature of 100°С within 10-20 hours, at the molar ratio of [Rh]:[C60]:[CHBr3 or CBr4]= 1:100:100-500. The technical result of the invention is the increased output of the product, the reduced amount of the wastes, the insignificant consumption of the catalyst.

EFFECT: the invention ensures the increased output of the product, the reduced amount of the wastes, the insignificant consumption of the catalyst.

3 ex, 1 tbl

 

The invention relates to the field of organic synthesis, in particular the chemistry of bromine derivatives of fullerene C60.

Fullerene is one of the allotropic modifications of carbon and is a polyhedral (spherical) cluster consisting of 60 or more carbon atoms. [1. Whishaw, Ivemania: USP. chemistry. 62(5), (1993)].

Derivatives of fullerene widely used as superconductors, solid carbon films, materials for nonlinear optics, and useful properties often exhibit a fullerene derivative obtained on the basis of chemical reactions With60with metals, volatile organic molecules. For this reason, globally deployed extensive studies of chemical reactions of fullerenes (Whishaw, Ivemania: USP. chemistry. 62(5), (1993)).

Reactivity of fullerenes is very unusual. The behavior of fullerenes appear in the most simple chemical reactions: hydrogenation, galogenirovannyie, oxidation, etc.

Due to the presence in the molecule of a large number of double bonds (hence, reaction centers), the interaction of fullerene With60with many reagents is very tricky and leads to the formation of a mixture of isomers. This property of fullerene evident in the synthesis galoidoproizvodnykh, in particular, bromine derivatives of fullerene

In 1991-1992, it was found that the fullerene C60interacts with liquid bromine, giving a complex mixture of products joining With60Brn. Further, these studies have not been great development because of the difficulty of allocating individual compounds and monitoring the process of halogenation [2. Engkaulah, Ehimare. USP. chemistry. 62(5), (1993)].

In order to obtain the brominated products with low content of bromine, the reaction was carried out at the ratio of bromine to the fullerene 1÷3:1. However, bromination at a concentration of reagents is not. [3. R.Taylor, A.G.Avent, P.R.Birkeu, T.J.S.Dennis, J.P.Hare et al. Pure and Appl. Chem. Vol. 65, No. 1, p.135, 1993]. And only by using a substantial excess of bromine fullerenes With60/S70(a mixture of 85:15) or clean With a60are bromirovanii liquid bromine at 20°s and 50°With up With60Brn(n=2-4)with the IR spectrum, the absorption at 515-545 cm-1characteristic of the C-Br. [4. G.Olah, J.Bucsi, C.Lambert, R.Aniszfeld, N.J.Trivedi et al. J. Am. Chem. Soc., V.113, p.9385, 1991].

The outputs of the products obtained and the conversion of the original fullerene60/S70in the work not specified.

Fullerene C60it is soluble in CS2and holding the synthesized excess of liquid bromine in a solvent leads to the formation of dark brown crystals with a yield of 80%. Coz the ACLs data of x-ray analysis of this compound is 1, 3, 6, 11, 13, 18, 28, 31-octabromodiphenyl-C60. Bromination of fullerene C60in benzene or CCl4gives red crystals in the form of plates, the structure of which is defined as 1, 6, 9, 12, 15, 18-hexabromobenzene-C60. This same product was obtained when carrying out the reaction in chloroform [5. F.N.Tebbe, R.L.Harlow, D.B.Chase, D.L.Thorn, G.C.Campbell et al. Science V.256, p.882, 1992; 6. P.P.Birkett, P.B.Hitchcock, H.W.Kroto, R.Taylor, D.R.M.Walton. Nature V.357, p.479, 1992].

Processing of fullerene C60liquid bromine is completed by formation of the product composition With60Br24in the form of crystals yellow-orange color. The reaction of the synthesized reversible. Polybromide fullerene easily helps eliminate bromine, turning into dibromide (C60Br2and tetrabromide (C60Br4) [5].

Disadvantages of the method:

1. Method of ethnological, inconvenient and difficult to instrument design.

2. Bromine is corrosive, poisonous compound, especially at elevated temperatures; acts on the respiratory organs, the skin.

3. Low selectivity.

4. High consumption brainwashes agent.

The authors of this application has proposed a method of obtaining bromine derivatives of fullerene C60that does not have these disadvantages.

The method consists in the interaction of bromoform (CHBr3) and tetrabromomethane (CBr4with fullerene C60in prisutstvie and homogeneous metal complex registeruser catalyst - complex Wilkinson [RhCl(PPh3)3] at a temperature of 100°C for 10-20 hours. The reaction CHBr3(or CBr4with fullerene C60formed hydrobromide (or bromo derivatives) fullerene with a content of from 1 to 6 bromine atoms in the molecule With60and the number of bromine atoms in the resulting product is determined by the reaction conditions

Special experiments were optimal molar ratio of catalyst and reagents:[Rh]:[C60]:[CHBr3or CBr4]=1:100:100 to 500, preferably 1:100:300. The reaction can be performed in two ways:

1) upon prolonged heating at 100°20 hours;

2) at 100°10 hours with an activated form of the catalyst, which had been pre-heated solution of catalyst [RhCl(PPh3)3] CHBr3(or CBr4) in 1 ml of toluene at 180°C for 0.5-1 hours

The advantages of the proposed method.

1. High output bromo derivatives of fullerene C60(70-81%).

2. Availability pomeroyi and hydrobromide reagents.

3. The simplicity of instrumentation.

4. The versatility of ways depending on the reaction conditions to selectively receive bromo derivatives of fullerene with 1-6 halogen atoms.

5. Minor consumption of catalyst.

6. Reducing waste.

7. Reducing labor and energy costs and environmental safety.

The method is illustrated by examples.

Example 1. In a glass ampoule (V=20 ml), or in mikroavtobus stainless steel (V=20 ml) (the results of parallel experiments do not differ) under argon was placed 0.1 mmole RhCl(PPh3)3added 10 mmol of fullerene C60, 10-50 mmol tetrabromomethane (CBr4) in 5 ml of toluene. The ampoule was sealed (autoclave was closed and heated at 100°C for 20 hours with constant stirring. After the reaction, the ampoule (autoclave) was cooled to 20°C, dissected, the resulting reaction mass was filtered through a layer of alumina (eluent - chloroform), and then the solvent was evaporated in vacuum. To remove traces of the solvent the residue was kept under vacuum at 50°C for 5 hours

The reaction mass was analyzed by high performance liquid chromatography (C18 column, eluent: toluene-chloroform).

The purified product is a crystal dark brown color. IR range (νcm-1, 525, 575 (C-Br).

According to elemental analysis dibromopropane fullerene has the following composition. Found: C, 81.74%; Br, 18.26%. With60Br2.

Elemental analysis data of other bromine derivatives are listed below:

With60Br4: C, 68.99%; Br, 31.01%

(Calculated, %: C, 59.93; Br, 30.75)

With60Br6: C, 59.93%; Br, 40.07%

(Calculated, %: C, at 60.05; Br, 39.95)

Example 2. Activation of the catalyst: in a glass ampoule under argon was placed 0.1 mmole RhCl(PPh3)3, 10 mmol CBr4in 1 ml of toluene, the ampoule was sealed and heated at 180°With 1 hour. After cooling, the ampoule was opened, was added 10 mol fullerene in 4 ml of toluene, sealed ampoule was heated for 10 h at 100°C. Upon completion of the reaction, the treatment of the reaction mixture and isolation of the reaction products as in example 1.

Example 3. In a glass ampoule (autoclave) under argon was placed 0.1 mmol RhCl(PPh3)3added 10 mmol of fullerene, 10-50 mmol of bromoform (CHBr3) in 5 ml of toluene. Ampoule (autoclave) was heated at 100°C for 20 hours with constant stirring. Upon completion of the reaction, the treatment of the reaction mixture and isolation of the reaction products as in example 1.

Found, %: C, 89.73; H 0.12; Br, 10.15. C60HBr.

Calculated, %: C, 89.90; N, 0.13; Br, 9.97

Elemental analysis data of other bromine derivatives of fullerene to the following:

With60H2Br2: C, 81.58%; N, 0.22%; 18.20%

(Calculated, %: C, at 81.66; N, 0.23; Br, 18.11)

With60H3Br3: C, 74.85%; N, 0.29%; Br, at 24.86%

(Calculated, %: C, 74.80; H, 0.31; Br, 24.89)

The results of the experiments are shown in the table.

td align="center"> 10
Table 1
The results of experiments on bromirovanii and hydrobromination fullerene C60using CBr4and CHBr3under the action of RhCl(PPh3)3(solvent - toluene)
№ № Booking agentThe molar ratio of [Rh]:[C60]:[CBr4or CHBr3]Temperature, °CPro-have-tel-ness, hCon-version60, %The composition of the reaction products, %
With60Br2With60Br4With60Br6
1.CBr41:100:1001001025--100
2.-"--"--"-2031--100
3.-"-1:100:300-"--"-58--100
4 *-"--"--"-1061101575
5.*-"- 1:100:500-"-108151778
6.-"--"--"-2079--100
With60HBrWith60(HBr)2With60(HBr)3
7.CHBr31:100:1001001035--100
8.-"--"--"-2040--100
9.-"-1:100:300-"--"-555392
10.*-"--"--"-1062252352
11.-"-1:100:500-"-2070-595
12.*-"--"--"-10801080
Note:

Experiments 4, 5, 10, 12 carried out with an activated form of the catalyst.

The method of obtaining bromine derivatives of fullerene C60, characterized in that as pomeroyi agents use tetrabromomethane CBr4or bromoform CHBr3that react with fullerene C60in the presence of registeruser catalyst complex Wilkinson [RhCl(PPh3)3], and the molar ratio of the catalyst, fullerene and brainwashes agent is 1:100:100÷500, the reaction is carried out at a temperature of 100°C for 10-20 hours



 

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