JP2006503946A - ポリアルキレンカーボネートを製造するための方法 - Google Patents
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Abstract
Description
(i)孔径は、現在使用されているゼオライトよりも大きいものを実現することができ、
(ii)内部表面積は、現在使用されている有孔材料よりも大きいものであって、
(iii)孔径および/またはチャネル構造は、広い範囲に亘って調整することができ、
(iv)内部表面を形成する有機骨格成分は容易に官能化することができ、
(v)本発明による金属−有機骨格は、ホスト、溶剤または任意の他の付加的な物質が存在しない場合であっても安定であり、特に骨格は、その形状および寸法を圧潰および/または浸透および/または変更することはない。これは、本発明による材料が、触媒として使用されてもよい他の金属有機材料とは異なる点である。
本発明の好ましい実施態様
前記に示したように、金属有機骨格材料は、たとえばUS5748508、EP−A−0709253、M.O’Keeffeら、J.Sol.State Chem.,152(2000)第3〜20頁、H.Liら、Nature402(1999)第276頁以降、M.Eddaoudiら、Topics in Catalysis9(1999)第105〜111頁、B.Chenら、Science291(2001)第1021〜23頁に記載されている。前記材料を製造するための比較的廉価な方法は、DE10111230.0に記載されている。これらの刊行物の内容は、本発明の内容において十分反映されている。
i)1〜10個の炭素原子を有するアルキル基部分構造、
ii)1〜5個のフェニル環を有するアリール基部分構造、
iii)1〜10個の炭化水素を有するアルキル基または1〜5個のフェニル環を有するアリール基から成るアルキルまたはアリールアミン部分構造、
を有する化合物が挙げられ、その際、前記部分構造は、少なくとも二座の官能基“X”の少なくとも1種と結合し、この場合、“X”は前記化合物の部分構造と配位結合しており、その際Xは、以下の群から選択される:
a.1〜20個の炭素原子を有する直鎖、分枝、環式脂肪族基を含有する、アルキルアミンおよびこれらの相当するアルキルアンモニウム塩(およびこれらの相当する塩)、
b.1〜5個のフェニル環を有するアリールアミンおよびこれらの相当するアリールアンモニウム塩、
c.1〜20個の炭素原子を有する直鎖、分枝、または環式脂肪族基を含有する、アルキルホスホニウム塩、
d.1〜5個のフェニル環を有するアリールホスホニウム塩、
e.1〜20個の炭素原子を有する直鎖、分枝、または環式脂肪族基を含有する、アルキル有機酸および相当するアルキル有機アニオン(および塩)
f.1〜5個のフェニル環を有する、アリール有機酸およびこれらの相当するアリール有機アニオンおよび塩、
g.1〜20個の炭素原子を有する、直鎖、分枝または環式脂肪族基を含有する、脂肪族アルコール、
h.1〜5個のフェニル環を有するアリールアルコール、
i.以下の群からの無機アニオン:
硫酸イオン、硝酸イオン、亜硝酸イオン、亜硫酸イオン、重亜硫酸イオン、燐酸イオン、燐酸水素イオン、燐酸二水素イオン、二燐酸イオン、三燐酸イオン、亜燐酸イオン、塩化物イオン、塩素酸イオン、臭化物イオン、臭素酸イオン、ヨウ化物イオン、ヨウ素酸イオン、炭酸イオン、重炭酸イオンおよび前記無機アニオンの相当する酸および塩、
j.アンモニア、二酸化炭素、メタン、酸素、エチレン、ヘキサン、ベンゼン、トルエン、キシレン、クロロベンゼン、ニトロベンゼン、ナフタレン、チオフェン、ピリジン、アセトン、1−2−ジクロロエタン、メチレンクロライド、テトラヒドロフラン、エタノールアミン、トリエチルアミンおよびトリフルオロメチルスルホン酸。
NDC ナフタレンジカルボン酸
BDC ベンゼンジカルボン酸
ATC アダマンテートテトラカルボン酸
BTC ベンゼントリカルボン酸
BTB ベンゼントリベンゾエート
MTB メタンテトラベンゾエート
ATB アダマンテートテトラベンゾエート
ADB アダマンテートジベンゾエート
これら材料の合成例自体については、たとえばJ.Am.Chem.Soc.123(2001)第8241頁以降であるか、あるいはAcc.Chem.Res.31(1998)第474頁以降に記載されており、この場合、これらは十分に本発明の範囲内に包含されるものである。
例1:金属−有機骨格材料の製造
ビーカー中に、ジヒドロキシテレフタル酸2.43gおよび硝酸亜鉛四水和物 9.66gを、ジエチルホルミアミド 282.2g中に溶解し、かつ250ml容量の2種のテフロンコートされたオートクレーブに添加した。得られた溶液は黄緑色であった。これに、トリエチルアミン1.24gを滴加した(オートクレーブ当たり)。ゲル形状の白い物質が得られた。
種々のリガンドを用いての金属有機骨格材料は、以下の工程によって得ることができる:
反応フラスコ中に、3.67gのベンゼントリカルボン酸および19.26gの硝酸亜鉛四水和物を、ジエチルホルムアミド261.5g中に溶解した。混合物を130°に加熱すると同時に撹拌し、かつ前記温度を1.5時間に亘って維持し、結晶化を誘導した。
驚くべきことに、例1および例2の触媒は、二者択一的な共重合反応のための活性触媒であることが見出された。
Claims (6)
- 触媒の存在下で、二酸化炭素または二酸化炭素誘導物質ならびに酸化アルケンまたは酸化アルケン前駆体から、ポリアルキレンカーボネートを製造するための方法において、触媒が、孔および少なくとも1種の金属イオンならびに前記金属イオンと配位結合している少なくとも1種の少なくとも二座の有機化合物を含有する、金属−有機骨格材料を含むことを特徴とする、二酸化炭素または二酸化炭素誘導物質ならびに酸化アルケンまたは酸化アルケン前駆体から、ポリアルキレンカーボネートを製造するための方法。
- 金属−有機骨格触媒が、金属イオン成分としてZn2+を含有する、請求項2に記載の方法。
- 少なくとも二座の有機化合物が、少なくとも2個のカルボキシ基および/または少なくとも2個のカルボキシ基を有する1個または2個のフェニル環を有するアリール基を含む、アルキル基部分構造の群から選択される、請求項1に記載の方法。
- 少なくとも二座の有機化合物が、テレフタル酸または2,5−ジヒドロキシテレフタル酸から選択される、請求項4に記載の方法。
- 酸化アルケンが、エチレンオキシド、プロピレンオキシドおよびシクロヘキセンオキシドから成る群から選択される、請求項1から5までのいずれか1項に記載の方法。
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US10/279,940 US6617467B1 (en) | 2002-10-25 | 2002-10-25 | Process for producing polyalkylene carbonates |
PCT/EP2003/011704 WO2004037895A1 (en) | 2002-10-25 | 2003-10-22 | Process for producing polyalkylene carbonates |
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US (1) | US6617467B1 (ja) |
EP (1) | EP1558665B1 (ja) |
JP (1) | JP2006503946A (ja) |
CN (1) | CN1322026C (ja) |
AT (1) | ATE429458T1 (ja) |
AU (1) | AU2003276143A1 (ja) |
DE (1) | DE60327351D1 (ja) |
ES (1) | ES2324470T3 (ja) |
MY (1) | MY139209A (ja) |
TW (1) | TWI288148B (ja) |
WO (1) | WO2004037895A1 (ja) |
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JP2012503079A (ja) * | 2008-09-17 | 2012-02-02 | ノボマー, インコーポレイテッド | 脂肪族ポリカーボネートクエンチ方法 |
WO2015129685A1 (ja) * | 2014-02-26 | 2015-09-03 | 国立大学法人京都大学 | 多孔性配位高分子、及びその用途 |
US9732187B2 (en) | 2013-11-18 | 2017-08-15 | Lg Chem, Ltd. | Manufacturing method of polyalkylene carbonate resin |
US9751981B2 (en) | 2013-10-30 | 2017-09-05 | Lg Chem, Ltd. | Manufacturing method of organic zinc catalyst and manufacturing method of polyalkylene carbonate resin |
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US6617467B1 (en) * | 2002-10-25 | 2003-09-09 | Basf Aktiengesellschaft | Process for producing polyalkylene carbonates |
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Cited By (10)
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JP2008523181A (ja) * | 2004-12-10 | 2008-07-03 | ビーエーエスエフ ソシエタス・ヨーロピア | 超高分子量ポリカーボネートの製造および使用 |
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JP2012503079A (ja) * | 2008-09-17 | 2012-02-02 | ノボマー, インコーポレイテッド | 脂肪族ポリカーボネートクエンチ方法 |
US9751981B2 (en) | 2013-10-30 | 2017-09-05 | Lg Chem, Ltd. | Manufacturing method of organic zinc catalyst and manufacturing method of polyalkylene carbonate resin |
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US9732187B2 (en) | 2013-11-18 | 2017-08-15 | Lg Chem, Ltd. | Manufacturing method of polyalkylene carbonate resin |
WO2015129685A1 (ja) * | 2014-02-26 | 2015-09-03 | 国立大学法人京都大学 | 多孔性配位高分子、及びその用途 |
JPWO2015129685A1 (ja) * | 2014-02-26 | 2017-03-30 | 国立大学法人京都大学 | 多孔性配位高分子、及びその用途 |
US9670127B2 (en) | 2014-02-26 | 2017-06-06 | Kyoto University | Porous coordination polymer and application therefor |
US11219887B2 (en) | 2017-08-28 | 2022-01-11 | Lg Chem, Ltd. | Method for preparing organic zinc catalyst, organic zinc catalyst prepared by the method and method for preparing polyalkylene carbonate resin using the catalyst |
Also Published As
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AU2003276143A1 (en) | 2004-05-13 |
US6617467B1 (en) | 2003-09-09 |
CN1322026C (zh) | 2007-06-20 |
CN1708534A (zh) | 2005-12-14 |
TWI288148B (en) | 2007-10-11 |
EP1558665B1 (en) | 2009-04-22 |
AU2003276143A8 (en) | 2004-05-13 |
EP1558665A1 (en) | 2005-08-03 |
DE60327351D1 (de) | 2009-06-04 |
MY139209A (en) | 2009-08-28 |
ES2324470T3 (es) | 2009-08-07 |
TW200415176A (en) | 2004-08-16 |
WO2004037895A1 (en) | 2004-05-06 |
ATE429458T1 (de) | 2009-05-15 |
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