JP2010527890A - 配位的に不飽和な金属部位を有する表面官能基化された多孔性有機無機ハイブリッド材料又はメソポーラス材料の製造及びその触媒的応用 - Google Patents
配位的に不飽和な金属部位を有する表面官能基化された多孔性有機無機ハイブリッド材料又はメソポーラス材料の製造及びその触媒的応用 Download PDFInfo
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- JP2010527890A JP2010527890A JP2010509261A JP2010509261A JP2010527890A JP 2010527890 A JP2010527890 A JP 2010527890A JP 2010509261 A JP2010509261 A JP 2010509261A JP 2010509261 A JP2010509261 A JP 2010509261A JP 2010527890 A JP2010527890 A JP 2010527890A
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- 238000000921 elemental analysis Methods 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- MWVFCEVNXHTDNF-UHFFFAOYSA-N hexane-2,3-dione Chemical compound CCCC(=O)C(C)=O MWVFCEVNXHTDNF-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
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- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
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- 229910052684 Cerium Inorganic materials 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- 229910008051 Si-OH Inorganic materials 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910006358 Si—OH Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- JVCSQUWRWAUUII-UHFFFAOYSA-N carboxy cyclohexyl carbonate Chemical compound OC(=O)OC(=O)OC1CCCCC1 JVCSQUWRWAUUII-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
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- GVXHLXUFBFUGKE-UHFFFAOYSA-N ethane-1,2-dithiol Chemical compound SCCS.SCCS GVXHLXUFBFUGKE-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 125000001905 inorganic group Chemical group 0.000 description 1
- 229920000592 inorganic polymer Polymers 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
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- 239000013259 porous coordination polymer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical group [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N trans-Stilbene Natural products C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000004841 transmission electron microscopy energy-dispersive X-ray spectroscopy Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
、アミド基(−CONH2)、スルホン酸基(−SO3H)、スルホン酸アニオン基(−SO3 −)、メタンジチオ酸基(−CS2H)、メタンジチオ酸アニオン基(−CS2 −)、ピリジン基又はピラジン基等が例示され得る。より安定した有機無機ハイブリッド材料を誘導するためには、キレート部位が二つ以上である、二座配位又は三座配位のような有機物が有利に用いられ得る。キレートされた有機物が配位結合できる部位を有する場合、ビピリジン、ピラジン等のような中性有機物、テレフタレート、ナフタレンジカルボキシレート、ベンゼントリカルボキシレート、グルタレート、サクシネート等のようなカルボン酸のアニオン等のアニオン性有機物及びカチオン性有機物を含むことができる。テレフタレートのような芳香族環を有するカルボン酸アニオン、ホルメートのような線形のカルボン酸のアニオン及びシクロヘキシルジカーボネートのように非芳香族環を有するアニオンがカルボン酸アニオンとして用いられ得る。脱水素化部位を有した有機物及び特定の反応条件において脱水素化された形態に変化され得る化合物が用いられ得る。即ち、テレフタル酸のような有機酸を用いても、反応後は、テレフタレートは、金属成分と結合することができる。使用できる有機物の代表的な例としては、ベンゼンジカルボン酸、ナフタレンジカルボン酸、ベンゼントリカルボン酸、ナフタレントリカルボン酸、ピリジンジカルボン酸、ビピリジルジカルボン酸、ギ酸、蓚酸、マロン酸、コハク酸、グルタル酸、ヘキサンジオン酸、ヘプタンジオン酸、シクロヘキシルジカルボン酸のような有機酸及びそれらのアニオン;ピリジン;及びピラジンを含むことができる。また、二つ以上の有機物を混合して用いることもできる。
赤外線分光法を利用して3200−3400cm−1領域でアミノ基(−NH2)が存在することを確認し、1150cm−1領域でS=O対称結合が存在することを確認した。
Claims (18)
- 不飽和金属部位を有する多孔性有機無機ハイブリッド材料又は多孔性有機無機メソポーラス材料と有機物、無機物、イオン性液体及び有機無機金属化合物を反応させて製造される、表面官能基化された多孔性有機無機ハイブリッド材料の製造方法。
- 前記多孔性有機無機ハイブリッド材料は、中心金属イオンが有機リガンドと結合して形成された結晶性高分子化合物であって、分子サイズ又はナノサイズの細孔構造を有するものであり、前記多孔性有機無機メソポーラス材料は、異種金属が置換されて不飽和金属部位を有する分子体である、請求項1に記載の方法。
- 前記多孔性有機無機ハイブリッド材料の中心金属イオンの前駆体は、Ti、Zr、Hf、V、Nb、Ta、Cr、Mo、W、Mn、Re、Fe、Ru、Os、Co、Rh、Ir、Ni、Pd、Pt、Cu、Ag、Au、Zn、Cd、Hg、Mg、Ca、Sr、Ba、Sc、Y、Al、Ga、In、Tl、Si、Ge、Sn、Pb、As、Sb及びBiのうちから選択される一つ以上の金属又はその金属化合物である、請求項2に記載の方法。
- 前記リガンドとして作用できる有機物は、カルボン酸基、カルボン酸アニオン基、アミノ基、イミノ基、アミド基、スルホン酸基、スルホン酸アニオン基、メタンジチオ酸基、メタンジチオ酸アニオン基、ピリジン基又はピラジン基から選択される一つ以上の官能基を有する化合物又はその混合物である、請求項2に記載の方法。
- 前記カルボン酸基を有する化合物は、ベンゼンジカルボン酸、ナフタレンジカルボン酸、ベンゼントリカルボン酸、ナフタレントリカルボン酸、ピリジンジカルボン酸、ビピリジルジカルボン酸、ギ酸、蓚酸、マロン酸、コハク酸、グルタル酸、ヘキサンジオン酸、ヘプタンジオン酸、又はシクロヘキシルジカルボン酸から選択されるいずれか一つ以上である、請求項4に記載の方法。
- 前記多孔性有機無機ハイブリッド材料は、薄膜構造又はメンブレイン構造を有するものである、請求項2に記載の方法。
- 前記有機物は、下記の化学式1乃至3で表される化合物から1種以上の化合物である、請求項1に記載の方法。
[化学式1]
H2N−M−R1
[化学式2]
HS−M−R2
[化学式3]
(OH)2OP−M−R3
(前記1〜3式において、Mは、不飽和炭化水素を含むか、又は含まないC1〜C20のアルキレン又はアラルキレン基であり、R1、R2 R3は、独立的に、ハロゲン、ビニル基(−C=CH2)、アミノ基(−NH2)、イミノ基(−NHR14)、メルカプト基(−SH)、ヒドロキシ基(−OH)、カルボン酸基(−COOH)、スルホン酸基(−SO3H)、アルコキシ基(−OR)又はホスホリック基(−PO(OH)2)から選択される一つ以上に置換されるか、又は置換されていない有機物質アルキレン又はアラルキレン基である。) - 前記ポリオキソメタレートは、ケギン構造(Keggin structure)のアニオン[(XM12O40)n−、n=1〜10;X=P、Si、H、Ga、Ge、V、Cr、Me又はFe;M=W、Mo、Coのうちから一つ以上]、リンドクビスト構造(Lindqvist structure)のアニオン[(M6O19)n−、n=1〜10;M=W、Mo、Ta、V又はW]、アンダーソン−エバンス構造(Anderson−Evans structure)のアニオン[(Mx(OH)6M6O18)n−、n=1〜10;Mx=Cr、Ni、Fe、Mn;M=Mo、W]又は[(M4(H2O)4(P2W15O56)2)n−、n=1〜10;M=Cu、Zn、Ni、Mn等から選択される1種以上の遷移金属又は遷移金属クラスタ]又はドーソン−ウェルズ構造(Dawson−Wells structure)の(P2W15O56)2から選択される1種以上である、請求項1に記載の方法。
- 前記イオン性液体は、アンモニウム(ammonium)、ホスホニウム(Phosphonium)、スルホニウム(Sulphonium)、ピロリジニウム(Pyrrolidinum)、イミダゾリウム(Imidazolium)、チアゾリウム(Thiazolium)、ピリジニウム(Pyridium)及びトリアゾリウム(Triazolium)から選択される1種以上の塩である、請求項1に記載の方法。
- 前記有機金属化合物は、下記の化学式4乃至11で表される化合物から選択される1種以上である、請求項1に記載の方法。
[化学式4]
Si(OR1)4−xRx(1≦x≦3)
[化学式5]
Si(OR3)4−(y+z)R2 yZz(1≦y+z≦3)
[化学式6]
Si(OR4)4−aR5 aSi(1≦a≦3)
[化学式7]
Z1 b(OR6)3−bSi−A−Si(OR7)3−CZ2 C(0≦b≦2、0≦c≦2)
[化学式8]
R8 eM1(OR9)4−e(1≦e≦3)
[化学式9]
R10 gM2Z3 f(OR11)4−(f+g)(1≦f+g≦3)
[化学式10]
M3(OR12)h(1≦h≦2)
[化学式11]
M4(OR13)iZ4 j(1≦i+j≦2)
(前記化学式4〜11において、Aは、不飽和炭化水素を含むか、又は含まないC1〜C20のアルキレン又はアラルキレン基であり、Z1乃至Z4は、独立的に、ハロゲン元素から選択され、M1及びM2は、独立的に、遷移金属、ランタン系列及びアクチニウム系列金属から選択された1種以上の元素であり、M3及びM4は、独立的に、アルカリ土類金属又はアルカリ金属から選択される1種以上の元素であり、RとR1乃至R13は、独立的に、ハロゲン元素、ビニル基(−C=CH2)、アミノ基(−NH2)、イミノ基(−NHR14)、メルカプト基(−SH)、ヒドロキシ基(−OH)又はカルボン酸基(COOH)から選択される一つ以上に置換されるか、又は置換されていないC1〜C20のアルキル(alkyl)基、アルケニル(alkenyl)基又はアルキニル(alkynyl)基であるか、又は、ビニル基(−C=CH)、アミノ基(−NH2)、イミノ基(−NHR14)、メルカプト基(−SH)、ヒドロキシ基(−OH)又はカルボン酸基(COOH)から選択され、前記R14は、ハロゲン、アミノ基、メルカプト基又はヒドロキシ基に置換されるか、又は置換されていないC1〜C10のアルキル基、アルケニル基又はアルキニル基である。) - 前記方法は、下記を更に含む請求項1に記載の方法:
表面官能基化された多孔性有機無機ハイブリッド材料を貴金属、遷移金属、典型金属又はランタン族金属と反応させて2次で担持させるステップ。 - 前記多孔性有機無機ハイブリッド材料は、電気オーブンヒーティング方式又はマイクロウエーブヒーティング方式で製造されたものである、請求項11に記載の方法。
- 前記表面官能基化された多孔性有機無機ハイブリッド材料に、貴金属、遷移金属、典型金属及びランタン族から選択される1種以上の金属又はその酸化物を担持するステップを更に含む、請求項1乃至12のいずれか1項に記載の方法。
- 前記多孔性有機無機ハイブリッド材料は、クロムテレフタレート、鉄テレフタレート又はバナジウムテレフタレート、アルミニウムテレフタレート、クロムベンゼントリカルボキシレート、鉄ベンゼントリカルボキシレート、バナジウムベンゼントリカルボキシレート又はアルミニウムベンゼントリカルボキシレートである、請求項13に記載の方法。
- 前記多孔性有機無機ハイブリッド材料は、MIL−101、MIL−100及びMOF−500構造を有するものである、請求項14に記載の方法。
- 請求項1乃至15のいずれか1項の方法で製造された、表面官能基化された多孔性有機無機ハイブリッド材料組成物。
- 請求項1乃至16のいずれか1項の製造方法で製造された、表面官能基化された多孔性有機無機ハイブリッド材料を含む触媒組成物。
- 酸塩基反応、水素化反応、脱水素化反応、炭素−炭素結合反応、又は酸素、空気、過酸化水素を利用した酸化反応に用いられる請求項17に記載の触媒組成物。
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Families Citing this family (87)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8779175B2 (en) * | 2004-10-25 | 2014-07-15 | Synthonics, Inc. | Coordination complexes, pharmaceutical solutions comprising coordination complexes, and methods of treating patients |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002530413A (ja) * | 1998-11-20 | 2002-09-17 | モンテル テクノロジー カンパニー ビーブイ | 橋架けメタロセン、製造法、触媒系での使用 |
JP2004285315A (ja) * | 2002-05-15 | 2004-10-14 | Nippon Shokubai Co Ltd | 多孔性配位不飽和金属錯体 |
WO2006002582A1 (en) * | 2004-07-07 | 2006-01-12 | The Hong Kong University Of Science And Technology | Catalytic material and method of production thereof |
JP2007022911A (ja) * | 2005-07-18 | 2007-02-01 | Korea Res Inst Of Chem Technol | 連続攪拌式反応器を利用した多孔性物質及び混合金属酸化物の連続的製造方法、並びに連続的製造装置 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100676215B1 (ko) * | 2002-05-15 | 2007-01-30 | 니폰 쇼쿠바이 컴파니 리미티드 | 다공성 배위불포화 금속착체 |
JP4496986B2 (ja) * | 2005-02-21 | 2010-07-07 | 住友化学株式会社 | 多孔性金属錯体細孔内での重合方法 |
CN101151091B (zh) * | 2005-04-07 | 2010-06-23 | 密歇根大学董事会 | 具有敞开的金属部位的微孔金属有机构架中的气体高吸附 |
DE102005060364A1 (de) | 2005-12-16 | 2007-06-21 | Basf Ag | Sauer funktionalisierte metallorganische Gerüstmaterialien |
DE102005060361A1 (de) | 2005-12-16 | 2007-06-21 | BSH Bosch und Siemens Hausgeräte GmbH | Kochgerät |
KR100680767B1 (ko) | 2006-02-07 | 2007-02-09 | 한국화학연구원 | 다공성 유무기혼성체의 제조방법 |
-
2007
- 2007-05-21 KR KR1020070049415A patent/KR100864313B1/ko active IP Right Grant
- 2007-12-11 US US12/600,997 patent/US8569193B2/en active Active
- 2007-12-11 WO PCT/KR2007/006431 patent/WO2008143385A1/en active Application Filing
- 2007-12-11 EP EP07851402.3A patent/EP2152414B1/en active Active
- 2007-12-11 JP JP2010509261A patent/JP5452478B2/ja active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002530413A (ja) * | 1998-11-20 | 2002-09-17 | モンテル テクノロジー カンパニー ビーブイ | 橋架けメタロセン、製造法、触媒系での使用 |
JP2004285315A (ja) * | 2002-05-15 | 2004-10-14 | Nippon Shokubai Co Ltd | 多孔性配位不飽和金属錯体 |
WO2006002582A1 (en) * | 2004-07-07 | 2006-01-12 | The Hong Kong University Of Science And Technology | Catalytic material and method of production thereof |
JP2007022911A (ja) * | 2005-07-18 | 2007-02-01 | Korea Res Inst Of Chem Technol | 連続攪拌式反応器を利用した多孔性物質及び混合金属酸化物の連続的製造方法、並びに連続的製造装置 |
Non-Patent Citations (4)
Title |
---|
JPN6012060045; Jesse L.C. ROWSELL et al.: 'Effects of functionalization, catenation, and variation of the metal oxide and organic linking units' Journal of the American Chemical Society 2006, Vol.128, No.4, pp.1304-1315 * |
JPN6012060047; Hoi Ri MOON et al.: 'Porous metal-organic framework with coordinatively unsaturated MnII sites: sorption properties for v' Inorganic Chemistry 2006, Vol.45, No.21, pp.8672-8676 * |
JPN6012060049; O.I. LEBEDEV et al.: Chemistry of Matterials 2005, Vol.17, No.26, pp.6525-6527 * |
JPN6012060051; Joseph T. HUPP et al.: Science 2005, Vol.309, pp.2008-2009 * |
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EP2152414B1 (en) | 2018-02-14 |
KR100864313B1 (ko) | 2008-10-20 |
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EP2152414A1 (en) | 2010-02-17 |
US8569193B2 (en) | 2013-10-29 |
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US20100273642A1 (en) | 2010-10-28 |
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