JP5511427B2 - 抽出分離用吸着剤および極性化合物の分離法 - Google Patents
抽出分離用吸着剤および極性化合物の分離法 Download PDFInfo
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- JP5511427B2 JP5511427B2 JP2010031988A JP2010031988A JP5511427B2 JP 5511427 B2 JP5511427 B2 JP 5511427B2 JP 2010031988 A JP2010031988 A JP 2010031988A JP 2010031988 A JP2010031988 A JP 2010031988A JP 5511427 B2 JP5511427 B2 JP 5511427B2
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- adsorbent
- extraction
- hydrophilic
- separation
- zwitterionic polymer
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Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/30—Partition chromatography
- B01D15/305—Hydrophilic interaction chromatography [HILIC]
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/36—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving ionic interaction
- B01D15/361—Ion-exchange
- B01D15/364—Amphoteric or zwitterionic ion-exchanger
Description
固相抽出用カートリッジには、アセトニトリル、水、90%アセトニトリルの順で、例えば各10mLずつ通液し、コンディショニングを行う。必要に応じて、アセトニトリルの代わりにアセトンやテトラヒドロフランなど、水の代わりに、緩衝液や酸塩基などを用いても良い。
コンディショニング済みのカートリッジに予備抽出した試料溶液を、例えば20mLを通液し、測定対象の極性化合物を吸着剤10に捕捉し、濃縮させ、抽出する。
その後、測定対象の極性化合物が溶出しない範囲の水を含む水と混和する極性有機溶媒、例えば、アセトニトリル(必要に応じて、アセトンやテトラヒドロフランなど)を用いて、カートリッジ内の不要成分を洗浄する。
洗浄後、水(必要に応じて、緩衝液や酸塩基、極性有機溶媒を添加した溶液など)で極性化合物を溶出する。極性化合物を含む溶出液は、高速液体クロマトグラフィーや吸光光度法などを用いて溶液中の濃度を求める。
(1) 親水性基材Lの合成
親水性基材は、水系懸濁重合法により作製した。グリシジルメタクリレート160g、エチレンジメタクリレート40g、酢酸ブチル200gの混合溶液に2、2’−アゾビスイソブチロニトリル2gを溶解した混合物を、0.1%メチルセルロース水溶液1000mL中に加え、攪拌機を用いて攪拌羽根を400rpmで回転させ、油層を分散した。その後、分散液(懸濁液)を加温し、80℃で6時間重合反応を行った。生成した共重合体粒子を濾取し、水、メタノールの順で洗浄した。一日風乾後、分級を行い、45〜90μmの親水性基材L 75gを得た。この親水性基材Lの平均粒子径と分散度(d75/d25)をBeckman Coulter Multisizer 3 Coulter Counterで測定したところ、平均粒子径は64.5μm、分散度は1.26であった。また、比表面積と平均細孔径をBeckman Coulter SA3100 Surface Area Analyzerで測定したところ、比表面積は31m2/g、平均細孔径は20nmであった。
ジアリルアミン−マレイン酸共重合体(日東紡績製PSA−410C、濃度40%)50mLを、水250mL、2−プロパノール100mLの混合溶媒中に加え、均一な溶液とした後、実施例1の(1)で得られた親水性基材L 50gを加え、攪拌して均一なスラリーとした。さらに、5M NaOH 50mLを加えて、攪拌しながら60℃で20時間反応をさせた。反応終了後、2−プロパノール、水、メタノールの順で洗浄し、一晩風乾させ、両性イオン性高分子結合吸着剤Aを得た。導入された両性イオン性高分子の量を求めるため、Perkin Elmar 2400 Series II CHNS/O Elemental Analyzerで測定したところ、窒素量は0.64N%であった。
実施例1で得られた両性イオン性高分子結合吸着剤Aの内20gを、水200mLと5M NaOH 20mLの混合溶液中に分散し、均一なスラリーとした。その後、ソルビトールポリグリシジルエーテル(ナガセケムテック製、デナコールEX−611、平均分子量約630)1gを加え、攪拌しながら60℃で4時間反応をさせた。反応終了後、水、メタノールの順で洗浄し、一晩風乾させ、両性イオン性高分子結合吸着剤Bを得た。導入された両性イオン性高分子の量を求めるため、PerkinElmar 2400 Series II CHNS/O Elemental Analyzerで測定したところ、窒素量は0.67N%であり、両性イオン性高分子結合吸着剤Aからの両性イオン性高分子の脱離はなかった。
実施例1で得られた両性イオン性高分子結合吸着剤Aの内20gを、水200mLと5M NaOH 20mLの混合溶液中に分散し、均一なスラリーとした。その後、ジアリルアミン−マレイン酸共重合体(日東紡績製PSA−410C、濃度40%)50mLを加え、均一なスラリーとした。さらに、ソルビトールポリグリシジルエーテル(ナガセケムテック製、デナコールEX−611、平均分子量約630)1gを加え、攪拌しながら60℃で4時間反応をさせた。反応終了後、水、メタノールの順で洗浄し、一晩風乾させ、両性イオン性高分子結合吸着剤Cを得た。導入された両性イオン性高分子の量を求めるため、PerkinElmar 2400 Series II CHNS/O Elemental Analyzerで測定したところ、窒素量は0.92N%であり、両性イオン性高分子結合吸着剤Aに比べ両性イオン性高分子の結合量が、約50%増加していた。
比較例として、非特許文献5および非特許文献6に記載のスルホベタインゲルを合成した。合成方法は非特許文献5および非特許文献6を参考に行った。すなわち、グリシジルメタクリレート50g、N,N−ジメチルアクリルアミド10g、エチレンジメタクリレート40g、酢酸ブチル40g、2−メチルブタノール60gの混合溶液に2、2’−アゾビスイソブチロニトリル1gを溶解した混合物を、0.2%ポリビニルアルコール(重合度500)水溶液1、000mL中に加え、攪拌機を用いて攪拌羽根を250rpmで回転させ、油層を分散した。その後、分散液(懸濁液)を加温し、70℃で7時間重合反応を行った。生成した共重合体粒子を濾取し、水、メタノールの順で洗浄した。一日風乾後、分級を行い、45〜90μmの親水性基材M 35gを得た。この親水性基材Mの平均粒子径をBeckman Coulter Multisizer 3 Coulter Counterで測定したところ、平均粒子径は64μmであった。また、比表面積と平均細孔径をBeckman Coulter SA3100 Surface Area Analyzerで測定したところ、比表面積は84m2/g、平均細孔径は15.6nmであった。ついで、2−ブロモエタンスルホン酸ナトリウムの10重量%水溶液100mLに30%ジメチルアミン水溶液15mLを加え、室温で20時間反応させた。その後、陽イオン交換樹脂(Dowex AG50−X4)および陰イオン交換樹脂(Dowex AG1−X8)を充填したクロマト管に通液し、過剰のジメチルアミンなどの不純物を除去し、N,N−ジメチルエタンスルホン酸水溶液を得た。その後、再結晶により得られた結晶を40℃の真空乾燥機中で乾燥させた。親水性基材Mを0.1Mの塩酸でクロロヒドリン型に変換した基材1gに、上記方法により得られたN,N−ジメチルエタンスルホン酸1.5gおよび水酸化ナトリウム水溶液(pH12.5)20mLを加え、40℃で7時間攪拌しながら反応させた。反応終了後、水、メタノールの順で洗浄し、乾燥させ、比較対象のスルホベタイン型吸着剤を得た。
実施例1ないし実施例3で得られた3種の両性イオン性高分子結合吸着剤A、BおよびC 50mgをとり、下部に孔径20μmのフィルタを挿入した注射筒型固相抽出カートリッジに充填し、さらに上部にも孔径20μmのフィルタを挿入した。また、比較例により合成したスルホベタイン型吸着剤も同様の方法にカートリッジとした。このカートリッジに、アセトニトリル10mL、純水20mL、アセトニトリル−水(9:1)10mLを順に通液して、カートリッジのコンディショニングを行った。その後、表1に示す被検化合物をアセトニトリル−水(9:1)で溶解した溶液(濃度:1ppm)10mLを通液し、被検化合物を各吸着剤で抽出した。表1において、log Po/wはオクタノール/水分配係数であり、この値が小さいものほど水に分配しやすい化合物であることを意味する。その後、アセトニトリル5mLで洗浄後、純水10mLを用いて各吸着剤に抽出された被検化合物を溶出させた。各溶出液を、紫外可視分光光度計を用いて測定し、得られた吸光度と吸着処理を行わない被検試料標準溶液の吸光度から、各吸着剤における抽出回収率を求めた。表1に被検化合物とその溶解度と水−オクタノール分配比(log Po/w)を、式4−9に構造を示す。
(1) 親水性基材Nの合成
グリシジルメタクリレート80g、エチレンジメタクリレート120g、酢酸ブチル200gの混合溶液に2、2’−アゾビスイソブチロニトリル2gを溶解した混合物を、0.1%メチルセルロース水溶液1、000mL中に加え、ホモミキサーの高速回転により、油滴の中心径が約10μmになるように油層を分散した。その後、分散液(懸濁液)を加温し、80℃で6時間重合反応を行った。生成した共重合体粒子を濾取し、水、メタノールの順で洗浄した。一日風乾後、分級を行い、風力分級機を用いて平均粒子径約10μmの親水性基材N 80gを得た。この親水性基材Nの平均粒子径と分散度(d75/d25)をBeckman Coulter Multisizer 3 Coulter Counterで測定したところ、平均粒子径は10.1μm、分散度は1.16であった。また、比表面積と平均細孔径をBeckman Coulter SA3100 Surface Area Analyzerで測定したところ、比表面積は185m2/g、平均細孔径は12.9nmであった。
得られた親水性基材Nに、実施例1の(2)と同様の条件でジアリルアミン−マレイン酸共重合体(日東紡績製PSA−410C、濃度40%)を結合後、2−プロパノール、水、メタノールの順で洗浄し、一晩風乾させ、両性イオン性高分子結合吸着剤Dを得た。得られた両性イオン性高分子結合吸着剤Dを3等分し、その一つは、実施例2と同一の条件で、ソルビトールポリグリシジルエーテル(ナガセケムテック製、デナコールEX−611、平均分子量約630)で架橋反応を行い、両性イオン性高分子結合吸着剤Eを得た。さらに、実施例3と同様に、ジアリルアミン−マレイン酸共重合体(日東紡績製PSA−410C、濃度40%)を共存させた条件で、ソルビトールポリグリシジルエーテル(ナガセケムテック製、デナコールEX−611、平均分子量約630)で架橋反応を行い、両性イオン性高分子結合吸着剤Fを得た。
実施例5の(2)により得られた両性イオン性高分子結合吸着剤D、EおよびFを、内径4.6mm、長さ150mmのステンレス製クロマト管に充填し、親水性相互作用クロマトグラフィーによりの核酸塩基類の分離を行った。測定条件を以下に示す。
移動相:アセトニトリル−0.1M酢酸アンモニウム(95+5)
流量:1.0mL/min
カラム温度:40℃
検出:紫外吸収検出器(波長250nm)
試料:チミン、ウラシル、アデニン、シトシン、各10ppm
試料注入量:40μL
11:親水性基材
12:反応性官能基(結合部位)
13:両性イオン性高分子
14:架橋部位
20:シリンジ型固相抽出カートリッジ(カラム)
30:上部フリット
40:下部フリット
50:ルアー型固相抽出カートリッジ(カラム)
51:エンプティカラムボディ
52:エンプティカラムキャップ
53:上部接続部
54:下部接続部
Claims (6)
- 前記親水性基材は、イミノ基またはアミノ基と反応することが可能な反応性モノマーと架橋性モノマーとの共重合反応により得られる親水性の共重合体、または、イミノ基またはアミノ基と反応することが可能な官能基を導入可能な親水性の共重合体であることを特徴とする請求項1に記載の抽出分離用吸着剤。
- 親水性基材に両性イオン性高分子を結合した後、エポキシ化合物によって両性イオン性高分子を架橋したことを特徴とする請求項1または請求項2に記載の抽出分離用吸着剤。
- 前記エポキシ化合物による両性イオン性高分子の架橋を行う際に、エポキシ化合物と共に両性イオン性高分子を更に添加して架橋を行うことを特徴とする請求項3に記載の抽出分離用吸着剤。
- 請求項1ないし請求項4のいずれか1つに記載の抽出分離用吸着剤を充てんした分析用のカラムに、水と混和する極性有機溶媒で調整された被検溶液を通液して、測定対象の極性化合物を該吸着剤に捕捉し、濃縮させた後、測定対象の極性化合物が溶出しない範囲の水を含む水と混和する極性有機溶媒で該吸着剤を洗浄し、その後、水、緩衝液、酸塩基極性またはこれらに有機溶媒を添加した溶液により測定対象の極性化合物を該吸着剤から溶出させることを特徴とする極性化合物の抽出法。
- 請求項1ないし請求項4のいずれか1つに記載の抽出分離用吸着剤を液体クロマトグラフィー用のクロマト管に充てんしたカラムを液体クロマトグラフに装着し、水と混和する極性有機溶媒と水または緩衝液との混合溶媒を移動相として通液して、測定対象の極性化合物を該吸着剤でクロマトグラフィックに分離することを特徴とする極性化合物の分離法。
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