WO2004058784A1 - Compose element organique du groupe du platine de fullerenol et/ou d'ester d'hydrogene sulfate de fullerenol, utilisation et procede de production de ces produit - Google Patents

Compose element organique du groupe du platine de fullerenol et/ou d'ester d'hydrogene sulfate de fullerenol, utilisation et procede de production de ces produit Download PDF

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Publication number
WO2004058784A1
WO2004058784A1 PCT/JP2003/016204 JP0316204W WO2004058784A1 WO 2004058784 A1 WO2004058784 A1 WO 2004058784A1 JP 0316204 W JP0316204 W JP 0316204W WO 2004058784 A1 WO2004058784 A1 WO 2004058784A1
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Prior art keywords
fullerenol
group element
platinum
platinum group
hydrogen sulfate
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PCT/JP2003/016204
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English (en)
Japanese (ja)
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Gohei Yoshida
Kazutaka Ikeda
Fumio Chiba
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The Honjo Chemical Corporation
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Publication date
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Priority to AU2003296175A priority Critical patent/AU2003296175A1/en
Publication of WO2004058784A1 publication Critical patent/WO2004058784A1/fr

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/006—Palladium compounds
    • C07F15/0066—Palladium compounds without a metal-carbon linkage
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • H01B1/122—Ionic conductors
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/86—Inert electrodes with catalytic activity, e.g. for fuel cells
    • H01M4/90—Selection of catalytic material
    • H01M4/92—Metals of platinum group
    • H01M4/923—Compounds thereof with non-metallic elements
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/30—Hydrogen technology
    • Y02E60/50—Fuel cells

Definitions

  • the present invention relates to an organic platinum group element compound of fullerenol and / or fullerenol hydrogen sulfate, its use, and its production method.
  • the present invention relates to an organic platinum group element compound in which a platinum group element is bonded to a carbon atom of fullerenol and / or fullerenol hydrogen sulfate, a use thereof, and a method for producing the same.
  • Such an organic platinum group element compound is a compound in which a platinum group element is bonded to a carbon atom of a proton conductive carbon cluster, fullerenol and / or fullerenol hydrogen sulfate.
  • carbon clusters that is, aggregates of closed-shell molecules consisting of only carbon atoms such as fullerenes and carbon atoms consisting of tubular molecules such as carbon nanotubes, are representative materials in nanotechnology (ultra-fine technology). Therefore, it is expected to be applied to a wide range of fields such as electronic materials, medical uses, and mechanical uses.
  • an organic palladium compound is produced by the reaction of fullerene (C 60 ), one of such carbon clusters, with a palladium complex (H. Nagashima et al., J. Chem. Soc, Chem. Commun. , 1992, 377), and such an organic palladium compound of fullerene has been reported to be useful, for example, as a hydrogenation catalyst (H. Nagashima et al., Chemistry Letters, 1992, 1361). Similarly, it has been reported that organoplatinum compounds obtained by the reaction of fullerene (C 60 ) with a platinum complex are also useful as hydrogenation catalysts (H. Nagashima et al., Chemistry Letters, 1994, 1207).
  • the present invention has been made in view of the above-mentioned circumstances in an electrode of a fuel cell, and has a function of dispersing and carrying platinum at an atomic level. In the following, focusing on their properties, they may be referred to as “proton conductive carbon clusters”.) To provide an organic platinum group element compound and its use, particularly as a proton conductor and a method for producing the same. With the goal. Disclosure of the invention
  • an organic platinum group element compound wherein a platinum group element is bonded to a carbon atom of fullerenol and / or fullerenol hydrogen sulfate.
  • such an organic platinum group element compound can be obtained by reacting fullerenol and / or fullerenol hydrogen sulfate with a platinum group element zero-valent complex.
  • a proton conductor comprising the above-mentioned organic platinum group element compound.
  • the platinum group element is preferably platinum or palladium.
  • FIG. 2 is an F T-IR spectrum of fullerenol obtained in Reference Example 1.
  • FIG. 3 is an FT-IR spectrum of the fullerenol hydrogen sulfate obtained in Reference Example 2.
  • FIG. 4 is an FT-IR spectrum of the fullerene C 60 -platinum compound obtained in Reference Example 5.
  • FIG. 5 shows the radial distribution function (local structure) of the fullerene C 60 -platinum compound obtained in Reference Example 5.
  • FIG. 6 is an FT-IR spectrum of the fullerenol-platinum compound obtained in Example 1.
  • FIG. 7 shows a radial distribution function (local structure) of the fullerenol-platinum compound obtained in Example 1.
  • FIG. 8 is a FT-IR spectrum of the fullerenol hydrogensulfate monoplatinum compound obtained in Example 2.
  • FIG. 9 shows the radial distribution function (local structure) of the fullerenol hydrogensulfate monoplatinum compound obtained in Example 2.
  • FIG. 10 is an FT-IR spectrum of the fullerene C 60 —palladium compound obtained in Reference Example 6.
  • FIG. 11 shows the radial distribution function (local structure) of the fullerene C 60 -palladium compound obtained in Reference Example 6.
  • FIG. 12 is a FT-IR spectrum of the fullerenol-palladium compound obtained in Example 3.
  • FIG. 13 shows the radial distribution function (local structure) of the fullerenol-palladium compound obtained in Example 3.
  • FIG. 14 is an FT-IR spectrum of the fullerenol hydrogen sulfate mono-palladium compound obtained in Example 4.
  • FIG. 15 shows the radial distribution function (local structure) of the fullerenol hydrogensulfate monopalladium compound obtained in Example 4.
  • the proton conductive carbon cluster which is a starting material for obtaining fullerenol and z or a fullerenol hydrogen sulfate having a platinum group element bonded thereto is a hydroxyl group and z or a hydrogen sulfate group thereof.
  • Carbon cluster that has Nol and z or fullerenol hydrogen sulfate are preferably used.
  • such a proton-conductive carbon cluster does not need to have a single composition.
  • the number of carbon atoms forming the parent fullerene is the same as that of the parent fullerene. As long as it is an integer that can be formed, as is already known, when the parent fullerene is described as C n , n is, for example, 60, 70, 76, 78, 8 At least one selected from 0, 82, 84 and the like may be used. However, according to the present invention, particularly, as the parent fullerene, fullerene C 60 having 60 carbon atoms, fullerene C 70 having 70 carbon atoms, or a mixture thereof is preferably used.
  • the proton conductive carbon cluster may have only a hydroxyl group, may have only a hydrogen sulfate ester group, and may have both a hydroxyl group and a hydrogen sulfate ester group. You may.
  • the number of hydroxyl groups and Z or the hydrogen sulfate ester group thereof in such a proton conductive carbon cluster is not particularly limited as long as it is within the range of the number of carbon atoms constituting the fullerene molecule.
  • fullerene it is only necessary that one molecule has one or more hydroxyl groups, while the upper limit is less than half the number of carbon atoms constituting the parent fullerene skeleton It is preferable that In the case of fullerenol hydrogensulfate, fullerenol hydrogensulfate can be obtained by replacing the hydroxyl group of fullerenol with a hydrogensulfate ester group.
  • the upper limit is preferably not more than half the number of carbon atoms constituting the parent fullerene skeleton.
  • the fullerenol hydrogensulfate may or may not have a hydroxyl group together with the hydrogensulfate ester group.
  • fullerene having 60 or 70 carbon atoms or a mixture thereof is used as a starting material to obtain fullerenol / fullerenol hydrogensulfate, which is reacted with a platinum group element zero-valent complex.
  • a platinum group element compound in which a platinum group element is bonded to a carbon atom of fullerene, which is a parent of fullerenol-fullerenol hydrogen sulfate can be obtained.
  • fullerene having 60 or 70 carbon atoms or a mixture thereof is used as a starting material to obtain fullerenol / fullerenol hydrogensulfate, which is further added to an inert atmosphere such as nitrogen, helium, or argon. Under the reaction solvent, the platinum group element By doing so, the organic platinum group element compound according to the present invention can be obtained.
  • the number of hydroxyl groups of the fullerenol molecule is usually in the range of 1 to 30 and is preferably Is in the range of 5 to 20.
  • the number of hydrogensulfate groups in the fullerenol hydrogensulfate ester molecule is usually in the range of 1 to 30.
  • the total of the hydroxyl group and the hydrogen sulfate ester group in the molecule is preferably 30 or less.
  • the number of bisulfate groups in the fullerenol bisulfate molecule is preferably in the range of 2 to 20, and the total number of hydroxyl groups and bisulfate ester groups in the molecule Is preferably in the range of 5 to 20.
  • the fullerenol used as a starting material preferably has the general formula (III)
  • C n represents fullerene which is a parent
  • X is a number in the range of 1 to 30).
  • X is preferably in the range of 5 to 20. What is a number.
  • the fullerenol hydrogensulfate used as a starting material preferably has the general formula (IV)
  • C n represents fullerene as a parent
  • X is a number in the range of 0 to 29
  • y is a number in the range of 1 to 30.
  • x + y is a range of 1 to 30. Is the number.
  • X is a number ranging from 0 to 13
  • y is a number ranging from 2 to 20
  • x + y is a number ranging from 5 to 20. is there.
  • the platinum group element zero-valent complex is not particularly limited.
  • a platinum (0) complex / palladium (0) complex is preferably used.
  • the platinum (0) complex include bis (dibenzylideneacetone) platinum (0), bis (??-1,5-cyclooctadiene) platinum (0), bis (77-aryl) platinum (0) And the like.
  • the palladium (0) complex for example, tris (dibenzylideneacetone) dipalladium (0) and the like are preferably used.
  • Such a zero-valent platinum group element complex is usually used as a raw material for a proton-conductive carbon cluster 1 It is used in an amount of 1 to 5 parts by mol, based on the platinum group element, relative to the parts by mol. According to the present invention, by adjusting the amount of the platinum group element 0-valent complex to be used for the proton conductive carbon cluster, the platinum group element is added to the proton conductive carbon cluster in an amount of 0.5 to 1 mol part per 1 part by mole. An organic platinum group compound in 3 mole parts can be obtained.
  • the reaction solvent is particularly limited as long as it is inert to the reaction and uniformly disperses or dissolves the proton conductive carbon cluster and the platinum group element zero-valent complex.
  • water, ethanol, getyl ether, benzene, toluene, xylene and the like are used.
  • aromatic hydrocarbons such as toluene and benzene are preferably used.
  • the reaction temperature of the proton-conductive carbon cluster and the platinum group element zero-valent complex is usually in the range of room temperature (25 ° C.) to 120 ° C., preferably in the range of 50 to 100 ° C. However, it is not limited to these.
  • a precipitate is separated from the obtained reaction mixture by centrifugation, washed with, for example, toluene, dried under reduced pressure, and a target organic platinum group element compound of a proton conductive carbon cluster, that is, The proton conductive carbon clusters and the organoplatinum group element compounds can be obtained as a powder.
  • organic platinum group element compound of the proton conductive carbon cluster according to the present invention has at least one kind of proton conductive group selected from a hydroxyl group and a hydrogen sulfate ester group, and has a parent material, fullerene.
  • C n represents the fullerene is a matrix
  • M represents a platinum group element
  • X is the number of 1 to 3 0 range
  • z is a number from 0.5 to 3 range.
  • C n represents the fullerene is a matrix
  • M represents a platinum group element
  • the number of the range of X is 0 to 2 9
  • y is a number in the range of 1 to 3
  • z is 0.5
  • x + y is a number in the range of 1 to 30.
  • the organic platinum group element compound of the proton-conductive carbon cluster according to the present invention is a compound represented by the general formula (I), wherein X is a number in the range of 1 to 30, and z is a number in the range of 0.5 to 3.
  • X is a number in the range of 0 to 13
  • y is a number in the range of 2 to 20
  • fullerene as a parent is Although not particularly limited, it is preferably C 60 , C 70 or a mixture thereof, and the platinum group element is preferably platinum or palladium.
  • an organic platinum group element compound of fullerenol and / or fullerenol hydrogen sulfate can be obtained.
  • Such an organic platinum group element compound of the proton conductive carbon cluster has a platinum group element supported and dispersed on the molecule at an atomic level, and is useful as a proton conductor. It is useful as an electrode or an electrocatalyst in which the utilization of elements has been dramatically increased.
  • the above samples were subjected to local structure analysis of platinum element by the XAFS method (X-ray absorption spectroscopy). That is, the XAFS spectra of the platinum metal and the sample were measured, and the Fourier transform was performed on the spectra to determine the radial distribution function (local structure).
  • the peak of the Pt--Pt bond was observed at around 2.5 A.
  • the peak corresponding to the above Pt-Pt bond shifts to about 0.5 to 1.0 'person, shifts to the short distance side, and appears to about 1.5 to 2.OA, and this peak is observed. This is probably due to the Pt—C bond.
  • the proton conductivity of this sample determined in the same manner as in Reference Example 1 was 2.4 X 1 O-sZcm.
  • the FT-IR spectrum of the reaction product (sample) thus obtained showed a new absorption band in addition to the fullerenol-based absorption band. This new absorption band almost coincided with the absorption band of the fullerene C 60 -platinum compound obtained in Reference Example 5.
  • the above samples were subjected to local structure analysis of platinum element by the XAFS method (X-ray absorption spectroscopy). That is, the XAFS spectra of platinum metal and the above sample were measured, and the Fourier transform was performed on the spectra to determine the radial distribution function (local structure). As a result, as shown in FIG. 7, the peak of the Pt_Pt bond is found at around 2.5 A. In the above sample, the peak corresponding to the Pt—Pt bond was 0.5 to 0.5 A. The peak shifts to about 1.0 A, nearer to 1.5 to 2.OA, and this peak appears to be due to Pt—C bonds. Further, the proton conductivity of the above sample obtained in the same manner as in Reference Example 1 was 6.3 X 1 O.sSZcm.
  • the content of platinum calculated from this elemental analysis was almost the same as the amount of incombustible substances in the above-mentioned thermal analysis measurement.
  • the above samples were subjected to local structure analysis of platinum element by the XAFS method (X-ray absorption spectroscopy). That is, the XAFS spectra of platinum metal and the above sample were measured, and the Fourier transform was performed on the spectra to determine the radial distribution function (local structure). As a result, as shown in FIG. 9, the peak of the Pt—Pt bond is observed at around 2.5 A. In the above sample, the peak corresponding to the Pt—Pt bond was 0.5. It shifts to the short distance side by about 1.0 A, and is observed at about 1.5 to 2.OA, and this peak is considered to be due to the Pt—C bond.
  • the conductivity of the above sample obtained in the same manner as in Reference Example 1 was 3.2 ⁇ 10-4 SZcm.
  • the local structure analysis of the palladium element was performed on the sample by the XAFS method (X-ray absorption spectroscopy). That is, the XAFS spectra of the palladium metal and the sample were measured, and a Fourier transform was performed on the spectrum to obtain a radial distribution function (local structure).
  • the peak of the Pd—Pd bond is observed at around 2.5 A.
  • the peak corresponding to the Pd—Pd bond is the fullerene C 60 —
  • a new peak is observed at about 1.9A, and this peak is considered to be due to the Pd-C bond.
  • the proton conductivity of this sample determined in the same manner as in Reference Example 1 was 6.8 ⁇ 1 ⁇ -sSZcm.
  • the local structure analysis of the palladium element was performed on the sample by the XAFS method (X-ray absorption spectroscopy). That is, the XAFS spectra of the palladium metal and the sample were measured, and a Fourier transform was performed on the spectrum to obtain a radial distribution function (local structure).
  • the peak of the Pd—Pd bond was observed at around 2.5 A.
  • the peak corresponding to the Pd—Pd bond was the fullerene C As in the case of 60- palladium compound, it shifts to the short distance side, and a new peak is observed at about 1.5A. This peak is considered to be due to the Pd-C bond.
  • the proton conductivity were determined in the same manner as in Reference Example 1 7 was 1 X 10- 5 SZcm.
  • the FT-IR spectrum of the reaction product thus obtained showed a new absorption band in addition to the absorption band based on fullerenol hydrogensulfate.
  • X-ray fluorescence measurement confirmed that palladium was contained in the reaction product.
  • the content of palladium determined from this elemental analysis was about 8%.
  • the local structure analysis of the palladium element was performed on the sample by the XAFS method (X-ray absorption spectroscopy). That is, the XAFS spectra of the palladium metal and the sample were measured, and the spectrum was subjected to a Fourier transform to obtain a radial distribution function (local structure).
  • the peak of the Pd—Pd bond is found at around 2.5 A.
  • the peak corresponding to the Pd—Pd bond is the fullerene C 60 —
  • the peak shifts to the short distance side, and a new peak is observed at about 1.5 A. This peak is considered to be due to the Pd-C bond.
  • the organic platinum group element compound in which a platinum group element is bonded to a carbon atom of fullerenol and Z or fullerenol hydrogen sulfate according to the present invention is a proton conductive carbon cluster fullerenol and Z or fullerenol. Since the platinum group element is bonded to the carbon atom of the hydrogen sulfate, it is useful as an electrode, an electrode catalyst, a proton conductor, etc. in, for example, a fuel cell.

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  • Crystallography & Structural Chemistry (AREA)
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Abstract

L'invention concerne un composé élément du groupe du platine en tant que grappe de carbone à proton conducteur, comprenant du fullérénol et/ou un ester d'hydrogène sulfate de fullérénol et un élément du groupe platine lié à un atome de carbone du fullérénol et de l'ester. Le composé élément organique du groupe du platine, en tant que grappe de carbone à proton conducteur est utile en tant que proton conducteur. Le composé élément organique du groupe du platine, en tant que grappe de carbone à proton conducteur peut être obtenu par réaction d'un complexe d'élément du groupe du platine de valence zéro avec un fullérénol et/ou un ester d'hydrogène sulfate de fullérénol.
PCT/JP2003/016204 2002-12-24 2003-12-17 Compose element organique du groupe du platine de fullerenol et/ou d'ester d'hydrogene sulfate de fullerenol, utilisation et procede de production de ces produit WO2004058784A1 (fr)

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AU2003296175A AU2003296175A1 (en) 2002-12-24 2003-12-17 Organic platinum-group element compound of fullerenol and/or fullerenol hydrogen sulfate ester, utilization of the same, and process for producing the same

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008128644A1 (fr) * 2007-04-18 2008-10-30 W.C. Heraeus Gmbh Complexes de palladium(0) et de dibenzylidène-acétone

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08310805A (ja) * 1995-05-10 1996-11-26 Sumitomo Electric Ind Ltd 導電性フラ−レン固体とその製造方法
JP2000261016A (ja) * 1999-03-11 2000-09-22 Japan Science & Technology Corp 光合成型有機太陽電池
WO2001008164A1 (fr) * 1999-07-26 2001-02-01 The Trustees Of The University Of Pennsylvania Nanotubes a paroi simple avec lumens pleins et leur procede de fabrication

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08310805A (ja) * 1995-05-10 1996-11-26 Sumitomo Electric Ind Ltd 導電性フラ−レン固体とその製造方法
JP2000261016A (ja) * 1999-03-11 2000-09-22 Japan Science & Technology Corp 光合成型有機太陽電池
WO2001008164A1 (fr) * 1999-07-26 2001-02-01 The Trustees Of The University Of Pennsylvania Nanotubes a paroi simple avec lumens pleins et leur procede de fabrication

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008128644A1 (fr) * 2007-04-18 2008-10-30 W.C. Heraeus Gmbh Complexes de palladium(0) et de dibenzylidène-acétone
JP2010524870A (ja) * 2007-04-18 2010-07-22 ヴェー ツェー ヘレーウス ゲゼルシャフト ミット ベシュレンクテル ハフツング パラジウム（０）−ジベンジリデンアセトン錯体
US7999126B2 (en) 2007-04-18 2011-08-16 W.C. Heraeus Gmbh Palladium(0)-dibenzylidene acetone complexes
RU2470029C2 (ru) * 2007-04-18 2012-12-20 Хераеус Прешес Металс ГмбХ энд Ко. КГ Дибензилиденацетоновые комплексы палладия (0)

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