CA2149955A1 - Process for concentrating fullerenes having more than 70 carbon atoms - Google Patents
Process for concentrating fullerenes having more than 70 carbon atomsInfo
- Publication number
- CA2149955A1 CA2149955A1 CA002149955A CA2149955A CA2149955A1 CA 2149955 A1 CA2149955 A1 CA 2149955A1 CA 002149955 A CA002149955 A CA 002149955A CA 2149955 A CA2149955 A CA 2149955A CA 2149955 A1 CA2149955 A1 CA 2149955A1
- Authority
- CA
- Canada
- Prior art keywords
- fullerenes
- column
- carbon atoms
- preliminary
- preliminary column
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 229910003472 fullerene Inorganic materials 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims abstract description 16
- 230000008569 process Effects 0.000 title claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 title claims abstract description 8
- 238000000926 separation method Methods 0.000 claims abstract description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000284 extract Substances 0.000 claims abstract description 8
- 239000000571 coke Substances 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 7
- RHZUVFJBSILHOK-UHFFFAOYSA-N anthracen-1-ylmethanolate Chemical compound C1=CC=C2C=C3C(C[O-])=CC=CC3=CC2=C1 RHZUVFJBSILHOK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003830 anthracite Substances 0.000 claims abstract description 6
- 239000003849 aromatic solvent Substances 0.000 claims abstract description 6
- 229910002804 graphite Inorganic materials 0.000 claims abstract description 6
- 239000010439 graphite Substances 0.000 claims abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 5
- 238000005442 molecular electronic Methods 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000000287 crude extract Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- -1 C2-C4-alkylbenzene Chemical compound 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 229940076134 benzene Drugs 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000003575 carbonaceous material Substances 0.000 description 2
- 238000010891 electric arc Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- APWZAIZNWQFZBK-UHFFFAOYSA-N 1-ethoxynaphthalene Chemical compound C1=CC=C2C(OCC)=CC=CC2=C1 APWZAIZNWQFZBK-UHFFFAOYSA-N 0.000 description 1
- LUZDYPLAQQGJEA-UHFFFAOYSA-N 2-Methoxynaphthalene Chemical compound C1=CC=CC2=CC(OC)=CC=C21 LUZDYPLAQQGJEA-UHFFFAOYSA-N 0.000 description 1
- RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 244000090689 Rumex alpinus Species 0.000 description 1
- 241000872198 Serjania polyphylla Species 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000011300 coal pitch Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000011301 petroleum pitch Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/15—Nano-sized carbon materials
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/15—Nano-sized carbon materials
- C01B32/152—Fullerenes
- C01B32/156—After-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nanotechnology (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Composite Materials (AREA)
- Manufacturing & Machinery (AREA)
- Carbon And Carbon Compounds (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Abstract
The invention relates to a process for concentrating fullerenes having more than 70 carbon atoms, which comprises a) applying a solution of a crude fullerene extract to a separation system containing a preliminary column and a main column charged with coke, anthracite and/or graphite as support material, then b) decoupling the preliminary column from the separa-tion system and c) desorbing from the preliminary column the fullerenes having more than 70 carbon atoms which are absorbed on the preliminary column using a nonpolar aromatic solvent.
Description
21~99S~
HOECHST A~ SELLSCHAFT HOE 94/F 142 Dr.DK/pp Deecription Proceee for concentrating fullerene~ having more than 70 carbon atome The fullerene blacke ueually prepared by the electric arc or reei~tance heating proceee contain, in addition to C60 and C70, eo-called higher fullerenee having more than 70 carbon atome.
After extraction of the fullerene black with benzene or toluene, the crude extract usually containe only from about 1 to 2% by weight of a complex mixture of higher fullerenee.
Only the use of epecially prepared electrodee which are not commercially available has made it poeeible to increaee thie proportion for the firet time to about 10 %
(Bethune et al. US-A-5 275 705).
The preparation in pure form of higher fullerenes etarting from the crude extract hae been eucceesfully carried out by chromatographic eeparation (D. Herren, J. Chromatogr. 644(1), 188 to 192, 1993).
It i~ particularly interesting that etereoisomer~ of higher fullerenes can aleo be eeparated.
Thue, thie claee of subetancee offers the unique oppor-tunity of etudying enantiomeric and diaetereomeric form~
of the element carbon.
It ie therefore an object of the invention to develop an impro~ed proceee which can be used on a large ecale and which givee fullerenes having more than 70 carbon atome in relatively high yielde.
214995~
The invention provides a procees for concentrating fullerenes having more than 70 carbon atoms, which comprises a) applying a crude fullerene extract to a separa-tion system cont~;n;ng a preliminary column and a main col-~m~, preferably in a volume ratio of from 1:20 to 1:40, charged with coke, anthracite and/or graphite as support material, then b) decoupling the preliminary col~mn from the separation system and c) desorbing from the preliminary column the ful-lerenes having more than 70 carbon atoms which are absorbed on the preliminary col~ using a nonpolar aromatic solvent.
The crude fullerene extract is obtA;nAhle by solid/li~uid extraction of fullerene-contA;n;ng carbon black, obtained by the electric arc process, using a nonpolar organic solvent, as described in W0 92/04279.
The extraction is advantageously carried out using an aromatic solvent which is also suitable for the process of the invention. Examples of such a solvent which i~
also suitable for the process steps a) and c) are ben-zene, toluene, xylene, mesitylene, C2-C4-alkylbenzene, tetralin, naphthalene, 1- and/or 2- methylnaphthalene, C2-C4-alkylnaphthalene, anisole, phenetole, nerolin, ethoxynaphthalene and also fluoro-, chloro-, dichloro-, trichloro- and bromobenzene.
It is also possible to use homogeneous mixtures of the specified solvents with one another or homogeneous mixtures with non-aromatic solvents, with the aromatic solvent always having to be the main constituent.
Preference is given to using benzene or toluene, particu-larly preferably toluene, as solvent.
The crude fullerene extract is generally applied as a saturated solution contA;n;ng from 0.5 to 10% by weight, 214995~
-preferably from 1 to 2% by weight, of the fullerenes C70. The main components of the crude extract are C60 (about 80% by weight) and C70 (about 18% by weight). For the process of the invention, it iB advantageous if the volume of crude extract applied iB from S to 10 times, preferably from 7 to 8 times, greater than the volume of the preliminary column.
The support materials coke, anthracite and graphite are particularly suitable for the described separation of fullerenes owing to their microstructure, crystal modifi-cation and porosity.
The following carbon materials are suitable for this purpose:
I) Cokes based on petroleum pitch and coal pitch;
II) Cokes prepared via the meso phase;
III) Cokes based on carbon black;
IV) Anthracite;
V) Graphites based on I) to III);
VI) Mixtures from the above classifications.
The ash content of the support materials should, owing to possible interactions, be limited, for example to c 1 to 0.1% by weight, with it also being possible for higher values to be acceptable. Which values are acceptable can be determined in simple experiments without inventive effort.
The carbon materials have to be introduced in milled form; the milling should not be too coarse (insufficient sharpness of separation) and not too fine (resistance to flow iB too great). A suitable example iB preferably a 21499~5 particulate material having a mean particle diameter D (D 50 %) of from about 10 to 40 ~m with a poured density of from about 0.4 to 0.6 g/cm3 and a tamped density of from 0.8 to 1.1 g/cm3.
The support material generally has a BET surface area of from 3 to 15 m2/g, preferably from 6 to 8 m2/g.
The volume ratio of preliminary column to main coll~mn is preferably from 1:25 to 1:35.
Pre~nmin~ntly C60 and C70 fullerenes are concentrated on the main coll~mn. If necessary, they can be separated by the process described in WO g4/06715.
The process of the invention can be carried out in the low, intermediate or high pressure range in a temperature range from 10 to 50C. The process is preferably carried out in the low pressure range up to a maximum of about 2 bar at a temperature of from 15 to 25C.
A particular advantage of the process of the invention is that no solvent change is reguired for the individual process steps.
The process of the invention enables the successful preparation of an extract of fullerenes cont~;n~ng more than 50% by weight of fullerenes ~ C70. Using such a concentrate, further chromatographic separation steps for the preparation in pure form of higher fullerenes in relatively large amounts are much more effective.
Owing to their electrooptical and electromagnetic proper-ties, fullerenes ~ C70 can be used in the field of mole-cular electronics. Chiral fullerenes ~ C70 can also be used for the preparation of chiral separation columns for enantiomeric analysis.
214995~
Example 1:
A separation system consisting of a 5 l preliminary col~~mn and a 150 l main column was charged with a slurry in toluene of SIGRI graphite HR 70 (consisting of 2/3 anthracite and 1/3 petroleum graphite having a mean particle diameter of 38 ~m, a poured density of 0.52 g/cm3 and a tamped density of 0.89 g/cm3) and the coll~mn material was compacted at 0.5 bar.
37.5 l of a saturated crude fullerene extract in toluene were then applied to the separation system.
The preliminary and main columns were subsequently decoupled and further eluted individually using toluene.
After elution of the preliminary column with from 1 to 2 bed volumes of toluene, the typical orange-brown color of the C60/C70 mixture disappeared and a yellow-brown further fraction was obt~; ne~ .
Further elution was carried out with another 5 to 7 bed volumes of toluene and the fractions were evaporated.
According to HPLC analy~is, thi~ fraction contains 1.14 g of fullerene ~ C70 (57% of theory).
HOECHST A~ SELLSCHAFT HOE 94/F 142 Dr.DK/pp Deecription Proceee for concentrating fullerene~ having more than 70 carbon atome The fullerene blacke ueually prepared by the electric arc or reei~tance heating proceee contain, in addition to C60 and C70, eo-called higher fullerenee having more than 70 carbon atome.
After extraction of the fullerene black with benzene or toluene, the crude extract usually containe only from about 1 to 2% by weight of a complex mixture of higher fullerenee.
Only the use of epecially prepared electrodee which are not commercially available has made it poeeible to increaee thie proportion for the firet time to about 10 %
(Bethune et al. US-A-5 275 705).
The preparation in pure form of higher fullerenes etarting from the crude extract hae been eucceesfully carried out by chromatographic eeparation (D. Herren, J. Chromatogr. 644(1), 188 to 192, 1993).
It i~ particularly interesting that etereoisomer~ of higher fullerenes can aleo be eeparated.
Thue, thie claee of subetancee offers the unique oppor-tunity of etudying enantiomeric and diaetereomeric form~
of the element carbon.
It ie therefore an object of the invention to develop an impro~ed proceee which can be used on a large ecale and which givee fullerenes having more than 70 carbon atome in relatively high yielde.
214995~
The invention provides a procees for concentrating fullerenes having more than 70 carbon atoms, which comprises a) applying a crude fullerene extract to a separa-tion system cont~;n;ng a preliminary column and a main col-~m~, preferably in a volume ratio of from 1:20 to 1:40, charged with coke, anthracite and/or graphite as support material, then b) decoupling the preliminary col~mn from the separation system and c) desorbing from the preliminary column the ful-lerenes having more than 70 carbon atoms which are absorbed on the preliminary col~ using a nonpolar aromatic solvent.
The crude fullerene extract is obtA;nAhle by solid/li~uid extraction of fullerene-contA;n;ng carbon black, obtained by the electric arc process, using a nonpolar organic solvent, as described in W0 92/04279.
The extraction is advantageously carried out using an aromatic solvent which is also suitable for the process of the invention. Examples of such a solvent which i~
also suitable for the process steps a) and c) are ben-zene, toluene, xylene, mesitylene, C2-C4-alkylbenzene, tetralin, naphthalene, 1- and/or 2- methylnaphthalene, C2-C4-alkylnaphthalene, anisole, phenetole, nerolin, ethoxynaphthalene and also fluoro-, chloro-, dichloro-, trichloro- and bromobenzene.
It is also possible to use homogeneous mixtures of the specified solvents with one another or homogeneous mixtures with non-aromatic solvents, with the aromatic solvent always having to be the main constituent.
Preference is given to using benzene or toluene, particu-larly preferably toluene, as solvent.
The crude fullerene extract is generally applied as a saturated solution contA;n;ng from 0.5 to 10% by weight, 214995~
-preferably from 1 to 2% by weight, of the fullerenes C70. The main components of the crude extract are C60 (about 80% by weight) and C70 (about 18% by weight). For the process of the invention, it iB advantageous if the volume of crude extract applied iB from S to 10 times, preferably from 7 to 8 times, greater than the volume of the preliminary column.
The support materials coke, anthracite and graphite are particularly suitable for the described separation of fullerenes owing to their microstructure, crystal modifi-cation and porosity.
The following carbon materials are suitable for this purpose:
I) Cokes based on petroleum pitch and coal pitch;
II) Cokes prepared via the meso phase;
III) Cokes based on carbon black;
IV) Anthracite;
V) Graphites based on I) to III);
VI) Mixtures from the above classifications.
The ash content of the support materials should, owing to possible interactions, be limited, for example to c 1 to 0.1% by weight, with it also being possible for higher values to be acceptable. Which values are acceptable can be determined in simple experiments without inventive effort.
The carbon materials have to be introduced in milled form; the milling should not be too coarse (insufficient sharpness of separation) and not too fine (resistance to flow iB too great). A suitable example iB preferably a 21499~5 particulate material having a mean particle diameter D (D 50 %) of from about 10 to 40 ~m with a poured density of from about 0.4 to 0.6 g/cm3 and a tamped density of from 0.8 to 1.1 g/cm3.
The support material generally has a BET surface area of from 3 to 15 m2/g, preferably from 6 to 8 m2/g.
The volume ratio of preliminary column to main coll~mn is preferably from 1:25 to 1:35.
Pre~nmin~ntly C60 and C70 fullerenes are concentrated on the main coll~mn. If necessary, they can be separated by the process described in WO g4/06715.
The process of the invention can be carried out in the low, intermediate or high pressure range in a temperature range from 10 to 50C. The process is preferably carried out in the low pressure range up to a maximum of about 2 bar at a temperature of from 15 to 25C.
A particular advantage of the process of the invention is that no solvent change is reguired for the individual process steps.
The process of the invention enables the successful preparation of an extract of fullerenes cont~;n~ng more than 50% by weight of fullerenes ~ C70. Using such a concentrate, further chromatographic separation steps for the preparation in pure form of higher fullerenes in relatively large amounts are much more effective.
Owing to their electrooptical and electromagnetic proper-ties, fullerenes ~ C70 can be used in the field of mole-cular electronics. Chiral fullerenes ~ C70 can also be used for the preparation of chiral separation columns for enantiomeric analysis.
214995~
Example 1:
A separation system consisting of a 5 l preliminary col~~mn and a 150 l main column was charged with a slurry in toluene of SIGRI graphite HR 70 (consisting of 2/3 anthracite and 1/3 petroleum graphite having a mean particle diameter of 38 ~m, a poured density of 0.52 g/cm3 and a tamped density of 0.89 g/cm3) and the coll~mn material was compacted at 0.5 bar.
37.5 l of a saturated crude fullerene extract in toluene were then applied to the separation system.
The preliminary and main columns were subsequently decoupled and further eluted individually using toluene.
After elution of the preliminary column with from 1 to 2 bed volumes of toluene, the typical orange-brown color of the C60/C70 mixture disappeared and a yellow-brown further fraction was obt~; ne~ .
Further elution was carried out with another 5 to 7 bed volumes of toluene and the fractions were evaporated.
According to HPLC analy~is, thi~ fraction contains 1.14 g of fullerene ~ C70 (57% of theory).
Claims (5)
1. A process for concentrating fullerenes having more than 70 carbon atoms, which comprises a) applying a solution of a crude fullerene extract to a separation system containing a preliminary column and a main column charged with coke, anthracite and/or graphite as support material, then b) decoupling the preliminary column from the sepa-ration system and c) desorbing from the preliminary column the ful-lerenes having more than 70 carbon atoms which are absorbed on the preliminary column using a nonpolar aromatic solvent.
2. The process as claimed in claim 1, wherein the solvent used is benzene or toluene.
3. The process as claimed in claim 1 or 2, wherein the volume of the crude fullerene extract is from 5 to 10 times greater than the volume of the preliminary column.
4. The process as claimed in claim 1, wherein the volume ratio of preliminary column to main column is in the range from 1:20 to 1:40.
5. Use of fullerenes having more than 70 carbon atoms in molecular electronics.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4418099.3 | 1994-05-24 | ||
| DE4418099A DE4418099A1 (en) | 1994-05-24 | 1994-05-24 | Process for the enrichment of fullerenes with more than 70 carbon atoms |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2149955A1 true CA2149955A1 (en) | 1995-11-25 |
Family
ID=6518844
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002149955A Abandoned CA2149955A1 (en) | 1994-05-24 | 1995-05-23 | Process for concentrating fullerenes having more than 70 carbon atoms |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0685427A1 (en) |
| JP (1) | JPH07315824A (en) |
| CA (1) | CA2149955A1 (en) |
| DE (1) | DE4418099A1 (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7494638B1 (en) | 1990-08-30 | 2009-02-24 | Mitsubishi Corporation | Form of carbon |
| CA2144746A1 (en) | 1992-09-16 | 1994-03-31 | Wolfgang Muller | Process for separating fullerenes |
| US5275705A (en) | 1992-12-09 | 1994-01-04 | International Business Machines Corporation | Process for making fullerenes |
-
1994
- 1994-05-24 DE DE4418099A patent/DE4418099A1/en not_active Withdrawn
-
1995
- 1995-05-11 EP EP95107155A patent/EP0685427A1/en not_active Withdrawn
- 1995-05-23 CA CA002149955A patent/CA2149955A1/en not_active Abandoned
- 1995-05-24 JP JP7124938A patent/JPH07315824A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07315824A (en) | 1995-12-05 |
| EP0685427A1 (en) | 1995-12-06 |
| DE4418099A1 (en) | 1995-11-30 |
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