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JP2841546B2 - 液体クロマトグラフィー用充填剤 - Google Patents

液体クロマトグラフィー用充填剤

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Publication number
JP2841546B2
JP2841546B2 JP1246444A JP24644489A JP2841546B2 JP 2841546 B2 JP2841546 B2 JP 2841546B2 JP 1246444 A JP1246444 A JP 1246444A JP 24644489 A JP24644489 A JP 24644489A JP 2841546 B2 JP2841546 B2 JP 2841546B2
Authority
JP
Japan
Prior art keywords
dicarboxylic acid
optically active
bianthryl
liquid chromatography
packing material
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
JP1246444A
Other languages
English (en)
Other versions
JPH03110464A (ja
Inventor
壮太郎 宮野
秀一 大井
雅之 四條
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Tosoh Corp
Original Assignee
Tosoh Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Tosoh Corp filed Critical Tosoh Corp
Priority to JP1246444A priority Critical patent/JP2841546B2/ja
Priority to EP90118330A priority patent/EP0420115B1/en
Priority to DE9090118330T priority patent/DE69000572T2/de
Priority to US07/587,942 priority patent/US5051176A/en
Publication of JPH03110464A publication Critical patent/JPH03110464A/ja
Application granted granted Critical
Publication of JP2841546B2 publication Critical patent/JP2841546B2/ja
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
    • B01J20/286—Phases chemically bonded to a substrate, e.g. to silica or to polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28002—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their physical properties
    • B01J20/28004—Sorbent size or size distribution, e.g. particle size
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B01J20/3092—Packing of a container, e.g. packing a cartridge or column
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    • B01J20/30—Processes for preparing, regenerating, or reactivating
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    • B01J20/3214—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the method for obtaining this coating or impregnating
    • B01J20/3217—Resulting in a chemical bond between the coating or impregnating layer and the carrier, support or substrate, e.g. a covalent bond
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    • B01J20/3217—Resulting in a chemical bond between the coating or impregnating layer and the carrier, support or substrate, e.g. a covalent bond
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    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
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    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
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    • B01J20/3259—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one of the heteroatoms nitrogen, oxygen or sulfur together with at least one silicon atom, these atoms not being part of the carrier as such comprising at least two different types of heteroatoms selected from nitrogen, oxygen or sulfur with at least one silicon atom
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
    • B01J20/3244—Non-macromolecular compounds
    • B01J20/3246—Non-macromolecular compounds having a well defined chemical structure
    • B01J20/3257—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one of the heteroatoms nitrogen, oxygen or sulfur together with at least one silicon atom, these atoms not being part of the carrier as such
    • B01J20/3261—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one of the heteroatoms nitrogen, oxygen or sulfur together with at least one silicon atom, these atoms not being part of the carrier as such comprising a cyclic structure not containing any of the heteroatoms nitrogen, oxygen or sulfur, e.g. aromatic structures
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    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
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    • B01J20/3263—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one of the heteroatoms nitrogen, oxygen or sulfur together with at least one silicon atom, these atoms not being part of the carrier as such comprising a cyclic structure containing at least one of the heteroatoms nitrogen, oxygen or sulfur, e.g. an heterocyclic or heteroaromatic structure
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    • B01J2220/58—Use in a single column

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  • Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

【発明の詳細な説明】 ［産業上の利用分野］ 本発明は種々の化合物の分離、特に異性体、さらには
従来分離が困難であったラセミ体の光学分割、特に（d
1）−アルコール修飾体の分割に有能な液体クロマトグ
ラフィー用充填剤である。
［産業上の技術］ 従来、種々の光学活性固定相によるラセミ体の直接分
割が知られている。例えば Y.Oamoto,CHEMTECH,1987,176;W.H.Pirkle,T.C.Pochapsk
y,G.S.Mahler,D.E.Corey,D.S.Reno,and D.M.Alessi,J.
Org.Chem.,51,4991（1986）等に詳しく記載されてい
る。これまで、種々の光学活性化合物を用いる固定相が
知られている。例えば、（Ｌ）−アミン酸、光学活性ア
ミド、又は光学活性カルボン酸がある。具体的に化合物
を示すと、（Ｌ）−バリン、（Ｌ）−ロイシン、（Ｌ）
−イソロイシン、（Ｌ）−フェニルグリシン誘導体、
（Ｓ）−１−（１−ナフチル）エチルアミン誘導体、
（Ｓ）−又は（Ｒ）−1,1′−ビナフチル−2,2′−ジカ
ルボン酸、又はキク酸などである。それらの光学活性化
合物を固定相とするために、一般的には、シリカゲルな
どの粒子表面にグラフトしたアミノアルキル基と光学活
性化合物のカルボキシル基との間のイオン結合、又は共
有結合を形成させ成立する。又は、シリカゲルなどの粒
子表面にグラフトしたカルボキシメチル基と光学活性ア
ミノ化合物との間に先と同様の結合様式により成立す
る。
これら光学活性固定相のラセミ体識別は一般に、に、
アミノ結合とラセミ体のアミド結合、エステル結合、水
酸基との間の水素結合およびπ−π相互作用などによ
り、固定相にラセミ体が保持される際に、ｄ体１体間の
保持は立体的に微少な環境の差によって、保持能に差が
生じることによって、達成されるというものである。ま
た、その場合の溶離液としては、一般にヘキサン−アル
コール系が使用される。
［発明が解決しようとする課題］ 上述の作用により、種々のラセミ体が分離されてきた
が、これまで、dl−アルコール修飾体の分離、特に脂肪
族（dl）−アルコール修飾体の簡便な分割に有効な固定
相は見出されていなかった。
［課題を解決するための手段及び作用］ 本発明者らは、前述したような、（dl）−アルコール
修飾体の光学分割に広く使用出来る固定相を見出すべく
鋭意検討した結果。（Ｓ）−又は（Ｒ）−1,1′−ビア
ントリル−2,2′−ジカルボン酸を固定相とすることに
より優れた充填剤が得られることを見出し本発明を完成
させた。
すなわち、本発明は、（Ｓ）−又は（Ｒ）−1,1′−
ビアントリル−2,2′−ジカルボン酸を固定相として用
いる液体クロマトグラフィー用充填剤を提供するもので
ある。
［作用］ 以下更に本発明を詳細に説明する。
本発明の光学活性化合物（Ｓ）−又は（Ｒ）−1,1′
−ビアントリル−2,2′−シカルボン酸は公知の方法つ
まり（dl）−1,1′−ビアントリル−2,2′−ジカルボン
酸をキニジンなどのアルカロイドを用い光学分離するこ
とによって得ることが出来る。
即ち、（dl）−1,1′−ビアントリル−2,2′−ジカル
ボン酸キニジン塩を加熱還流エタノールに溶解させ冷時
析出する結晶をろ別しさらにエタノールに懸濁させ加熱
還流により溶解させ放冷後、ろ別し（Ｒ）−ジカルボン
酸キニジン塩を得る。
ろ液を減圧留去し得られた粗結晶を同様の処理をする
ことにより（Ｓ）−ジカルボン酸キニジン塩を得ること
ができる。
各々の塩を塩酸処理することにより光学活性（Ｓ）−
又は（Ｒ）−1,1′−ビアントリル−2,2′−ジカルボン
酸をそれぞれ得ることが出来る。
本発明光学活性化合物を固定相とする充填剤を用いる
場合、その基材としては、シリカゲル、ガラスビーズ、
ケイソウ土等の多孔性担体が用いられ、球状でも破砕状
でも良いが、好ましくは球状が良い。粒径は、0.1−100
0μｍで細孔径が、10〜1000Åのもの、好ましくは粒径
１〜100μｍ、細孔径50〜500Åが良い。該光学活性化合
物を固定化する方法としては、基材担体に、吸着させる
方法、イオン結合により固定化する方法、アミド結合な
どの共有結合により固定化する方法などがあげられる。
液体クロマトグラフィーとしての条件を考慮すると、ア
ミド結合又はイオン結合により固定化するのが好まし
い。アミド結合又はイオン結合を形成させるには基材担
体表面にアミノ基含有のオイガノシラン処理剤を溶媒中
で反応させ、基材担体表面にアミノ基を導入する。この
アミノ基の導入料は、感想担体ペースで2.0meq./gまで
が好ましい。このようにして得られたアミノ基含有担体
に、ペプチド合成時の縮合剤、例えば、ジシクロヘキシ
ルカルボジイミド、Ｎ−エトキシカルボニル−２−エト
キシ−1,3−ジヒドロキノリン、１−エチル−３−（３
−ジメチルアミノプロピル）−カルボジイミドなどの存
在下、前述した光学活性1,1′−ビアントリル−2,2′−
ジカルボン酸を作用させ固定化する。又は縮合剤を添加
せずイオン結合により固定化することもできる。もちろ
ん両結合が存在することも可能である。
本発明充填剤のカラムへの充填方法は公知の常法によ
り行なうことが出来る。
［実施例］ 以下、本発明を実施例によりさらに説明するが、本発
明はこれに限定されるものではない。
実施例１ （１）（アミノアルキルグラフトシリカゲルの調製） シリカゲル（150℃、１×10-4ttorで約６時間乾燥し
たもの）50.24gの無水トルエン300mlの懸濁液に３−ア
ミノプロピルトリエトキシシラン100g（0.45mol）を加
え、N2下、穏やかに40時間加熱還流する。反応懸濁液を
冷却後G4のガラスフィルターでシリカをろ別し、トルエ
ン、MeOH、アセトン、エーテルで順次洗浄した後、乾燥
しアミノプロピル基グラフトシリカゲルを得た。
収量 59.66g,元素分析値:C％,8,10;H％,2.07;N％,1.4
2.アミノ基導入量:1.01mmol/g（Ｎ−元素分析値より） （２）（dl−1,1′−ビアントリル−2,2′−ジカルボン
酸の光学分割） dl−1,1′−ビアントリル−2,2′−ジカルボン酸2.6g
（5.65mmol）をエタノール125mlに懸濁後、加熱還流溶
解させキニジン4.25g（13.84mmol）を溶解後再び30分加
熱還流した後放冷し析出する結晶をろ別後、結晶をエタ
ノール50mlで再結晶を行い（Ｒ）−1,1′−ビアントリ
ル−2,2′−ジカルボン酸のキニジン塩2.47gを得る。
塩は2N−HCl中で拡販後、酢酸エチルで抽出し（Ｒ）
−1,1′−ビアントリル−2,2′−ジカルボン酸−2,2′
−ジカルボン酸0.93g（収率74.4％）を得る。
得られた光学活性体の光学純度はジアゾメタンでメチ
ルエステルとしPirkle型の光学分割用カラムの分析によ
り光学純度100％であることを確認した。
ろ液を減圧留去後同様の再結晶を繰り返し、得られた
塩を同様に塩酸処理することにより（Ｓ）−体を得る事
ができた。
（３）（Ｒ）−1,1′−ビアントリル−2,2′−ジカルボ
ン酸による光学活性固定相担体の合成 （Ｒ）−1,1′−ビアントリル−2,2′−ジカルボン酸
0.92g（2.08mmol）とＮ−エトキシカルボニル−２−エ
トキシ−1,3−ジヒドロキノン1.03g（4.06mmol）のDHF
溶液に（１）で合成したアミノプロピル基結合シリカ3.
00gを懸濁させ、N2下で超音波を８時間照射する。次に
反応懸濁液をG4のガラスフィルターを用いてシリカ125
℃の恒温浴中をろ別し、そのシリカをTHF,メタノール，
アセトン，エーテルで順次洗浄後減圧乾燥した。秋涼は
3.44gであった。
［応用例］ 実施例で得られた光学活性液体クロマトグラフィー用
充填剤をスラリー法によりカラムへ充填し、下記の測定
条件でラセミ体試料の分離を行い、保持係数（Ｋ′），
分離係数（α）を求めた。得られた結果を表１に示し
た。また、比較として、（Ｓ）−1,1′−ビナフチル−
2,2′−ジカルボン酸を固定相として測定した得られた
結果を表１に示した。
測定条件：カラム 4.6mmI.D.X25.0cmL.ステンレスカラ
ム 検出器 UV−8010（東ソ−製） ポンプ CCPO （東ソ−製） 温 度 25℃ 流 速 1.0ml/min. 移動相 ヘキサン−アルコール系（割合は表
１に示す） ［発明の効果］ 以上、説明したように、本発明光学活性化合物固定相
は、これまで分割が困難であったdl−アルコール類の分
割に非常に有効であり、その合成も容易であり、極めて
優れた充填剤である。
【図面の簡単な説明】
第１図は、本発明充填剤を用いた（dl）−２−Butyl−
3,5−dinitorophrnyl−carbamate分割のクロマトを示す
図である。
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.6，ＤＢ名) G01N 30/88 ＣＡＳ ＯＮＬＩＮＥ

Claims (1)

    (57)【特許請求の範囲】
  1. 【請求項１】（Ｓ）−又は（Ｒ）−1,1′−ビアントリ
    ル−2,2′−ジカルボン酸を固定相として用いることを
    特徴とする液体クロマトグラフィー用充填剤。
JP1246444A 1989-09-25 1989-09-25 液体クロマトグラフィー用充填剤 Expired - Fee Related JP2841546B2 (ja)

Priority Applications (4)

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JP1246444A JP2841546B2 (ja) 1989-09-25 1989-09-25 液体クロマトグラフィー用充填剤
EP90118330A EP0420115B1 (en) 1989-09-25 1990-09-24 Packing material for liquid chromatography
DE9090118330T DE69000572T2 (de) 1989-09-25 1990-09-24 Packungsmaterial fuer fluessigkeitschromatographie.
US07/587,942 US5051176A (en) 1989-09-25 1990-09-25 Packing material for liquid chromatography

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FR2687154B1 (fr) * 1992-02-07 1995-05-12 Rhone Poulenc Rorer Sa Nouveau derive de l'isoindolinone, sa preparation et les compositions pharmaceutiques qui le contiennent.
US5338529A (en) * 1992-04-27 1994-08-16 Research Corporation Technologies, Inc. Recognition and separation of carbon clusters
US5290440A (en) * 1992-06-23 1994-03-01 Research Corporation Technologies, Inc. High performance chiral selector
JPH07260762A (ja) * 1994-03-17 1995-10-13 Daicel Chem Ind Ltd 高速液体クロマトグラフィー用充填剤及びその製造法
JP4850335B2 (ja) * 2000-10-27 2012-01-11 キヤノン株式会社 画像形成装置
AU2002364803A1 (en) * 2002-11-29 2004-06-23 Pascal Aznar Pre-filled columns for flash chromatography and for solid-phase extraction with higher separating efficiency
US8137548B2 (en) * 2003-10-17 2012-03-20 Zirchrom Separations, Inc. Chelator-modified inorganic oxide particles
DE102005042647A1 (de) * 2005-09-08 2007-03-15 Noske-Kaeser Gmbh Filterwerkstoff gegen chemische Kampfstoffe
US9116150B2 (en) * 2007-11-19 2015-08-25 Emd Millipore Corporation Method of and device for packing a chromatography column

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US4324681A (en) * 1980-06-12 1982-04-13 Uop Inc. Chiral supports for resolution of racemates
JPS58202043A (ja) * 1982-05-19 1983-11-25 Sumitomo Chem Co Ltd グラフトしたクロマトグラフ充填剤およびそれを用いる鏡像体混合物の分析法
CA1204720A (en) * 1982-09-30 1986-05-20 Hajimu Kitahara Packing materials for chromatographic use and a method for analysis of an enantiomer mixture using the same
JPS59166502A (ja) * 1983-03-10 1984-09-19 Daicel Chem Ind Ltd 分離剤
JPS60161928A (ja) * 1984-01-31 1985-08-23 Daicel Chem Ind Ltd セルロースの硝酸エステルを含有する分離剤
JPS60226829A (ja) * 1984-03-29 1985-11-12 Daicel Chem Ind Ltd 多糖誘導体より成る分離剤
JPS60226830A (ja) * 1984-03-30 1985-11-12 Daicel Chem Ind Ltd １，３−グルカンより成る分離剤
JPS60226833A (ja) * 1984-04-05 1985-11-12 Daicel Chem Ind Ltd 多糖の芳香族エステル誘導体より成る分離剤
JPS60226832A (ja) * 1984-04-02 1985-11-12 Daicel Chem Ind Ltd 多糖の脂肪族エステルを含む分離剤
US4782040A (en) * 1984-04-09 1988-11-01 Dow Corning Corporation Porous materials having a dual surface
JPH0833380B2 (ja) * 1986-12-03 1996-03-29 東ソー株式会社 液体クロマトグラフイ−用充てん剤
JPS6420445A (en) * 1987-07-15 1989-01-24 Sumitomo Chemical Co Chromatograph packing agent and analysis of enantiomer using said agent
US4919803A (en) * 1988-12-09 1990-04-24 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services Liquid chromatographic chiral stationary phase

Also Published As

Publication number Publication date
EP0420115B1 (en) 1992-12-09
DE69000572D1 (de) 1993-01-21
JPH03110464A (ja) 1991-05-10
DE69000572T2 (de) 1993-04-15
EP0420115A1 (en) 1991-04-03
US5051176A (en) 1991-09-24

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