JP2007527429A - 複素環式アミン類のイオン液体 - Google Patents
複素環式アミン類のイオン液体 Download PDFInfo
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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- H—ELECTRICITY
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- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
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Abstract
Description
本発明は、イオン液体とその調製法に関する。特に、本発明は、比較的低い温度で液体であるイオン液体に関する。本発明に従った化合物は、約100℃未満の温度で液体であり、好ましくは約60℃未満で液体であり、より好ましくは周囲温度又はその付近で液体である。
この必要性は本発明により充足される。目下のところ、アミン窒素あたりおよそ3モルのフッ化水素を使用して複素環式アミンから形成されたイオン液体は、亜鉛、スズ及び鉄のハロゲン化物の第四級塩より導電性が数桁大きいことを発見した。より具体的には、複素環式アミンをアミン窒素1モルあたり約2.8モル〜3.2モルのフッ化水素と混合すると、従来技術の欠点が解決されるだけでなく、低い融点をはじめとする望ましい塩様(salt-like)特性を有するイオン液体が得られることを発見した。また、本発明のイオン液体は、望ましいことに、低い、水のような粘性を有する。
実施例1− フッ化水素を伴うピリジン塩の形成
約60グラムの無水フッ化水素を、攪拌器付のオートクレーブ中に含有された約55グラムのピリジンにゆっくり添加し、ピリジン対HFのモル比を1:3とした。反応の熱がひき混合物が冷却されたら、115グラムの液体を含有するオートクレーブを、ピリジンより90℃高くフッ化水素より160℃高い、180℃にて沸騰させた。この液体は、各成分に分離することができなかった。この物質の分析により、イオン液体[ピリジン・H+][H2F3]−(又はピリジン・3HF)としての新規化合物の構造が確認された。純粋なイオン液体の導電率は、98mS/cmと測定された。この液体は、ガラスと反応するOlah試薬とは異なり、ホウケイ酸ガラスをエッチングしなかった。
実施例2− フッ化水素を伴うα−ピコリン塩の形成
約60グラムの無水フッ化水素を、攪拌器付のオートクレーブ中に含有された約69グラムのα−ピコリンにゆっくり添加し、ピコリン対HFのモル比を1:3とした。反応の熱がひき混合物が冷却されたら、129グラムの液体を含有するオートクレーブを、α−ピコリンより80℃高くフッ化水素より180℃高い、200℃にて沸騰させた。この液体は、各成分に分離することができなかった。この物質の分析により、イオン液体[α−ピコリン・H+][H2F3]−(又はα−ピコリン・3HF)としての新規化合物の構造が確認された。純粋なイオン液体の導電率は、73mS/cmと測定された。この液体は、ガラスと反応するOlah試薬とは異なり、ホウケイ酸ガラスをエッチングしなかった。
実施例3− 二酸化ケイ素のエッチング
実施例1のピリジン塩の溶液を種々の濃度でプロピレンカーボネート中に溶解した。MEMsデバイス製造に使用される二酸化ケイ素を被覆したケイ素ウェーハをその中に浸漬した。エッチング速度は非常に速く、この速度はプロピレンカーボネート中のピリジン塩濃度に比例していた。
Claims (20)
- 少なくとも1種の複素環式アミンと、アミン窒素1モルあたり約2.8モル〜約3.2モルの無水フッ化水素との反応により形成される、約100℃未満の融点を有するイオン液体。
- 約60℃未満の融点を有する、請求項1記載のイオン液体。
- 約25℃未満の融点を有する、請求項2記載のイオン液体。
- 1種の複素環式アミンイオン化合物からなる、請求項1記載のイオン液体。
- 2種又はそれより多い複素環式アミン化合物からなる、請求項1記載のイオン液体。
- 約1〜約600ミリジーメンス/cmの比導電率を有する、請求項1記載のイオン液体。
- 複素環式アミンが、5〜7個の環員を含有する単環式化合物であり、1〜3個の環員が、窒素、酸素及び硫黄からなる群から選択されるヘテロ原子であり、前記ヘテロ原子の少なくとも1個が窒素である、請求項1記載のイオン液体。
- 複素環式アミンが、置換及び非置換ピロール類、置換及び非置換ピラゾール類、置換及び非置換ピリジン類、置換及び非置換ピラジン類、置換及び非置換ピリミジン類、置換及び非置換ピリダジン類、置換及び非置換チアゾール類、置換及び非置換オキサゾール類、置換及び非置換トリアゾール類、置換及び非置換類ピロリジン類、置換及び非置換ピロリドン類、置換及び非置換ピペラジン類、置換及び非置換ピペリジン類、ならびに、置換及び非置換ピロリン類からなる群から選択される、請求項7記載のイオン液体。
- 複素環式アミンがピリジン又はピコリンである、請求項8記載のイオン液体。
- 複素環式アミンが、8〜14個の環員を含有する多環縮合環構造であり、1〜3個の環員が、窒素、酸素及び硫黄からなる群から選択されるヘテロ原子であり、前記ヘテロ原子の少なくとも1個が窒素である、請求項1記載のイオン液体。
- 複素環式アミンが、置換及び非置換イミダゾール類、置換及び非置換キノリン類、置換及び非置換キノキサリン類、置換及び非置換プリン類、ならびに、置換及び非置換イソキノリン類からなる群から選択される、請求項10記載のイオン液体。
- 正極及び負極を含み、その両方が、請求項1記載のイオン液体を含む非水電解液と導電接触している、電気化学デバイス。
- デバイスが、電気化学キャパシタ、光起電デバイス、バッテリー、又は燃料電池である、請求項12記載の電気化学デバイス。
- デバイスが、電位差又は電解電量による電気化学センサーである、請求項12記載の電気化学デバイス。
- デバイスが電着デバイスである、請求項12記載の電気化学デバイス。
- 少なくとも1種の無水溶媒中に溶解された有効量の請求項1記載のイオン液体を含む、酸化ケイ素を除去するための無水エッチング溶液。
- イオン液体が、約1250オングストローム/分までの速度で酸化ケイ素層を除去するのに有効な量で存在する、請求項16記載の無水エッチング溶液。
- プロピレンカーボネート中にピリジン・3HFを含む、請求項16記載の無水エッチング溶液。
- 半導体基板から酸化ケイ素層を除去するための方法であって、請求項16記載の無水エッチング溶液を半導体基板の表面上の酸化ケイ素層と該酸化ケイ素層の一部が除去されるまで接触させることを含む、前記方法。
- 半導体基板が、酸化ケイ素被覆層を有するアルミニウム構成要素を含む、請求項19記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US55047104P | 2004-03-05 | 2004-03-05 | |
US60/550,471 | 2004-03-05 | ||
PCT/US2005/006863 WO2005092859A1 (en) | 2004-03-05 | 2005-03-04 | Ionic liquids of heterocyclic amines |
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JP2007527429A true JP2007527429A (ja) | 2007-09-27 |
JP2007527429A5 JP2007527429A5 (ja) | 2007-12-13 |
JP4964119B2 JP4964119B2 (ja) | 2012-06-27 |
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JP2007501965A Expired - Fee Related JP4964119B2 (ja) | 2004-03-05 | 2005-03-04 | 複素環式アミン類のイオン液体 |
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US (1) | US8148533B2 (ja) |
EP (1) | EP1720834A1 (ja) |
JP (1) | JP4964119B2 (ja) |
KR (1) | KR101214059B1 (ja) |
CN (1) | CN1950338B (ja) |
TW (1) | TW200602323A (ja) |
WO (1) | WO2005092859A1 (ja) |
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- 2005-03-04 US US11/072,964 patent/US8148533B2/en not_active Expired - Fee Related
- 2005-03-04 EP EP05724410A patent/EP1720834A1/en not_active Withdrawn
- 2005-03-04 TW TW094106635A patent/TW200602323A/zh unknown
- 2005-03-04 CN CN2005800136941A patent/CN1950338B/zh not_active Expired - Fee Related
- 2005-03-04 JP JP2007501965A patent/JP4964119B2/ja not_active Expired - Fee Related
- 2005-03-04 WO PCT/US2005/006863 patent/WO2005092859A1/en active Application Filing
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JP2012529163A (ja) * | 2009-06-04 | 2012-11-15 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 二成分エッチング |
JP2013500350A (ja) * | 2009-07-24 | 2013-01-07 | インビスタ テクノロジーズ エス エイ アール エル | イオン性液体を用いた合成方法 |
Also Published As
Publication number | Publication date |
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CN1950338B (zh) | 2012-05-16 |
KR101214059B1 (ko) | 2012-12-20 |
JP4964119B2 (ja) | 2012-06-27 |
EP1720834A1 (en) | 2006-11-15 |
WO2005092859A1 (en) | 2005-10-06 |
KR20070011363A (ko) | 2007-01-24 |
TW200602323A (en) | 2006-01-16 |
US20050196671A1 (en) | 2005-09-08 |
US8148533B2 (en) | 2012-04-03 |
CN1950338A (zh) | 2007-04-18 |
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