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Extraction of Fullerenes in Organic Solvents and the Development of Superior Isolation Procedures

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Extraction of Fullerenes in Organic Solvents and the Development of Superior Isolation Procedures Indian Journal of Chemistry Vol 31 MD, May 1992, pp. F32-F35 Extraction of fullerenes in organic solvents and the development of superior isolation procedures R Dhamodaran, I Kaliappam, N Sivaraman, T G Srinivasan, P R Vasudeva Rao & C K Mathews" Indira Gandhi Centre for Atomic Research, Kalpakkam 603 102, Tamil Nadu, India Received 20 February 1992 Development of methods for the isolation of fullerenes depends to a great extent on the identifica- tion of suitable solvents. In the present work, extraction of fuUerenes from carbon soot by a number of aliphatic, alicyclic and aromatic solvents has been examined at a constant temperature of 60°C. The results indicate that the extraction power of aliphatic straight chain hydrocarbons increases with in- crease in carbon chain length. The aromatic solvents have superior extracting power as compared to the aliphatic solvents. The higher extraction power of the aromatic solvents is attributed to their better solubilising action. Based on the experimental data, it was possible to develop efficient procedures for the chromatographic separation of C60 and C70 employing cyclohexane and a normal paraffin hydro- carbon mixture with average carbon number of 12 as solvents. C60 and C70 could both be isolated completely in pure form in much smaller volumes of eluant than in the hexane system. The recent isolation of macroquannnes of C60 makes this separation procedure tedious, and and C70 bas led to a veritable explosion in scien- large volumes of solutions have to be handled. tific literature on the properties of these all-car- Further, the use of toluene means that for recycl- bon clusters called fullerenes. Superconductivity ing of the solvents, fractional distillation has to be resorted to. has been observed in alkali metal-doped C60, a number of chemical reactions involving C60 have It has been observed that by using aromatic sol- been reported, and "endohedral complexes" of vents with higher boiling points such as 1, 2, 3, the fullerness, where a metal atom is trapped in- 5-tetramethylbenzene, fullerenes with high carbon side the ball shaped cage of the fullerene mole- numbers (as high as 300) could be extracted from cule, have also been reported. These as well as soot6.8.However, in the absence of any systematic many other aspects of fullerenes are covered in data on the solubility of various fullerenes in dif- several reviews1- 3. ferent solvents as a function of temperature, it The major advancement that was responsible cannot be concluded whether the efficient extrac- for the developments mentioned above was the tion of higher fullerenes is due to the nature of the discovery of a procedure for the preparation and solvent used, or the higher boiling points of the isolation of the fullerenes in bulk quantities. Pre- solvents. paration of fullerenes is carried out by the "con- In the present work, the extraction of fullerenes tact arc" method" or "resistance heating" method", from carbon soot by a number of organic solvents the former being more popular. High yields (upto was studied at a constant temperature (60°C), 40% of the soot as soluble material) have been with the following objectives: (a) to examine the obtained by suitable modifications in the design relative solubilities of fullerenes in these solvents and operation of the arcing set Up6. and (b) to arrive at procedures for chromatogra- The procedure widely used for the isolation of phic separations based on single solvent systems. fullerenes involves the soxhlet extraction of the The results of our studies indicate trends in the soluble material in the soot (with toluene or ben- solubilities of fullerenes based on the nature of zene as solvent) followed by rotary evaporation to the solvent, and thus point to better chromatogra- obtain a mixture of fullerenes. From this mixture, phic procedures. Two new solvents for fullerene separation are also suggested. C60 is separated by chromatographic separation on neutral alumina'>'.C60 is eluted from the co- lumn by using hexane- 5% toluene as eluant. C'o is Materials and Methods eluted by using hexane containing - 25% toluene. Carbon soot obtained by the contact arc meth- The poor solubility of fullerenes in hexane od was subjected to toluene soxhlet extraction to DHAMODARAN et al: EXTRAcnON OF FULlERENES IN ORGANIC SOLVENTS F33 recover the fullerenes. The details of the appara- a sample of the solvent phase withdrawn for the tus and the separation methods are reported in an measurement of the absorption spectrum. earlier paper", UV-visible absorption spectra were measured The paraffin solvent (Normal Paraffin Hydro- using a Shimadzu model UV-2100 spectropho- carbon-NPH) used in the present work was a mix- tometer. ture of n-decane, n-undecane, n-dodecane, n- tridecane and n-tetradecane, with an average car- Results and Discussion bon number of 12 supplied by Mis Tamilnadu Figures 1 and 2 show the absorption spectra of Petroproducts Ltd., Madras. It contained less than the solutions obtained by equilibration of the soot 0.003% of aromatics, as confirmed by its absorp- with various solvents. The absorbance values at tion spectrum. The absorbance at 270 nm, usually appropriate wavelengths were taken to indicate considered as an indicator of the concentration of the extent of extraction. Fig. 1 shows the spectra aromatics, was measured to be 0.150 absorbance of the extracts in aliphatic solvents and Fig. 2 units. All other solvents used were either of shows the spectra of the extracts in some aromat- HPLC grade or AR grade. The NPH solvent, as ic solvents as well as cyclohexane and carbon te- well as n-hexane and n-octane were used without trachloride. The spectra in Figs 1 and 2 were re- any further purification. n-Decane, n-dodecane and corded with extract solutions as such without di- n-tetradecane, which were found to contain some aro- lution. Table 1 gives some data on absorbance va- matic impurities, were purified by passing through neu- lues measured from these spectra, for a more tral alumina to remove aromatic impurities in the sol- quantitative comparison. vent. The absence of aromatic impurities was con- Since the studies have been made on raw soot, firmed by measuring the Uv-visible absorption the absorption spectral information obtained indi- spectrum. cates the combined solubility of C60 and C70 (ig- In the experiments to study the extraction of noring the higher fullerenes which are formed in fullerenes from soot, approximately 10 g of soot much lower amounts). Still, the data reported here was homogenised and a 100 mg aliquot was su- bring out clearly the role of the chemical nature spended in 10 ml of the solvent taken in an equil- of the solvent in solubilising the fullerenes. ibration tube. This tube was kept in a water bath The spectra in Fig. 1 as well as the data in maintained at a constant temperature of Table 1 clearly show that the solubility of the full- 60 ± 0.1 °C by circulating water from a thermostat erenes in aliphatic straight chain hydrocarbons in- through a glass jacket surrounding the bath. The creases with chain length. It is seen that the ex- entire apparatus was kept on top of a magnetic traction power of n-dodecane is approximately six stirrer, and the contents of the glass equilibration times that of n-hexane. This trend is contrary to tube were mixed by using a teflon coated magne- that normally observed in the solubilities of or- tic stirring bar. The equilibration was continued ganic compounds. On the basis of the theory of for 4 hr, after which the tube was centrifuged, and regular solutions, the solubility is expected to dec- , n.Hexcne (SO) 2 n, Hexane (Quaiigens) 3 n. Octane 4 n, Oecane 5 n, Dodecane 6 n, Tetradecane w u Z <t III g2500 tfl III <t OOOO'----'-~~~ 300 400 500 600 700 WAVE LENGTH (n m) Fig. I-Absorption spectra of extracts obtained by equilibration of carbon soot with various aliphatic hydrocarbon solvents. F34 INDIAN JCHEM,SEC.A&B,MAY 1992 I Cyclohexane 2 Carbon tetrachloride 3 Toluene 4 Benzene 5 Xylen~ 6 Mesltylene w u z <t g:'2500 ~ LD <t 400 500 600 700 WAVE LENGTH(n m) Fig. 2-Absorption spectra of extracts obtained by equilibration of carbon soot with benzene. toluene, xylene, mesitylene, CCl4 and cyclohexane Fig. 2 and the absorbance data provided in Table l=-Absorbance values for fullerene extracts in various solvents at selected wavelengths Table 1 show that the extraction in the aromatic Solvent Wavelength (nm) solvents as well as carbon tetrachloride and cyclo- hexane is higher than that in the aliphatic hydro- 468 403 378 330 carbons. This higher solubility of the fullerenes n-Hexane (SD) 0.159 0.199 0.539 2.706 obviously results from better interaction of the n- Hexane (Qualigens) 0.235 0.282 0.691 3.287 fullerenes with these solvents. It is seen that ex- n-Octane 0.402 0.461 1.277 >5 traction by mesitylene is the highest amongst the n-Decane 0.909 0.931 2.700 >5 aromatic hydrocarbons studied. Since these stud- n-Dodecane 1.219 1.228 3.476 >5 n-Tetradecane 1.507 1.529 4.038 >5 ies were carried out at the same temperature Cyclohexane 1.042 1.058 2.775 >5 (60°C), the better extraction power of this solvent Carbontetrachloride 1.333 1.362 3.817 >5 can be attributed to its better solvation properties Toluene 1.409 1.785 4.516 >5 and not to the higher extraction temperature. Benzene 1.554 1.776 4.396 >5 Xylene 1.606 2.459 >5 >5 Fig. 1 also indicates a difference in the extrac- Mesitylene 1.761 4.245 >5 >5 tion power of n-hexane obtained from two differ- ent sources (MIs SD Fine Chemicals and Mis Glaxo).
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