JPH0430378B2 - - Google Patents
Info
- Publication number
- JPH0430378B2 JPH0430378B2 JP59044943A JP4494384A JPH0430378B2 JP H0430378 B2 JPH0430378 B2 JP H0430378B2 JP 59044943 A JP59044943 A JP 59044943A JP 4494384 A JP4494384 A JP 4494384A JP H0430378 B2 JPH0430378 B2 JP H0430378B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- halogen atom
- packing material
- alkoxyl group
- 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 - Lifetime
Links
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 238000012856 packing Methods 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 150000001491 aromatic compounds Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000001282 organosilanes Chemical class 0.000 claims description 6
- 238000004811 liquid chromatography Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000004458 analytical method Methods 0.000 claims 1
- 239000000945 filler Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- NNOHXABAQAGKRZ-UHFFFAOYSA-N 3,5-dinitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(C(Cl)=O)=CC([N+]([O-])=O)=C1 NNOHXABAQAGKRZ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- -1 3,5-dinitrobenzoylamino group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 2
- UAQVHNZEONHPQG-ZETCQYMHSA-N N-benzoyl-L-alanine Chemical compound OC(=O)[C@H](C)NC(=O)C1=CC=CC=C1 UAQVHNZEONHPQG-ZETCQYMHSA-N 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- YKAKNMHEIJUKEX-UHFFFAOYSA-N m-methylhippuric acid Chemical compound CC1=CC=CC(C(=O)NCC(O)=O)=C1 YKAKNMHEIJUKEX-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- YOEBAVRJHRCKRE-UHFFFAOYSA-N o-methylhippuric acid Chemical compound CC1=CC=CC=C1C(=O)NCC(O)=O YOEBAVRJHRCKRE-UHFFFAOYSA-N 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
Classifications
-
- 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
- B01J20/281—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
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/10—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate
- B01J20/103—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate comprising silica
-
- 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
- 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
- B01J20/28014—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 form
- B01J20/28016—Particle form
- B01J20/28019—Spherical, ellipsoidal or cylindrical
-
- 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
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3202—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the carrier, support or substrate used for impregnation or coating
- B01J20/3204—Inorganic carriers, supports or substrates
-
- 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
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- 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
- B01J20/3219—Resulting in a chemical bond between the coating or impregnating layer and the carrier, support or substrate, e.g. a covalent bond involving a particular spacer or linking group, e.g. for attaching an active group
-
- 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
- B01J20/30—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
-
- 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
- B01J20/30—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
- B01J20/3259—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
- 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
- B01J20/30—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
-
- 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
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/50—Aspects relating to the use of sorbent or filter aid materials
- B01J2220/54—Sorbents specially adapted for analytical or investigative chromatography
Landscapes
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Treatment Of Liquids With Adsorbents In General (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】
本発明は３，５−ジニトロベンゾイルアミノ基
を有するオルガノシランをグラフトしたクロマト
グラフで充填剤およびそれを用いて芳香族化合物
の混合物を液体クロマトグラフイーにより分離
し、分析する方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention uses a chromatograph grafted with an organosilane having a 3,5-dinitrobenzoylamino group as a filler and uses the filler to separate and analyze a mixture of aromatic compounds by liquid chromatography. It's about how to do it.
液体クロマトグラフイーにより、芳香族化合物
の混合物特に位置異性体混合物を直接分離するこ
とは一般的には困難である。最近、庄野、新苗等
によるシクロデキストリンをグラフトした充填剤
により包接作用を利用する方法が試みられつつあ
るが、移動相として使用可能な溶媒は水に限られ
る等の欠点があり、分析方法としては充分ではな
い。 It is generally difficult to directly separate mixtures of aromatic compounds, particularly mixtures of positional isomers, by liquid chromatography. Recently, attempts have been made to utilize the inclusion effect using a cyclodextrin-grafted packing material by Shono and Shinnae et al., but this method has drawbacks such as the fact that the solvent that can be used as a mobile phase is limited to water. It's not enough.
本発明者らはかかる状況のもとで芳香族化合物
混合物の直接分離に特異的な性能を有し、製造が
比較的容易でしかも化学的に安定で実用的なグラ
フトした充填剤の開発を目標に鋭意検討を続けて
来た結果、一般式〔〕
〔式中、R1、R2およびR3は同一または相異なり、
アルキル基、アルコキシル基、ヒドロキシル基ま
たはハロゲン原子を表わし、少なくともその一つ
はアルコキシル基またはハロゲン原子である。〕
で示されるオルガノシランがヒドロキシル基をそ
の表面に持つ無機担体にグラフトされているクロ
マトグラフ充填剤が芳香族化合物の分離に優れた
効果を示すののみらず、通常の化学反応で容易に
製造しうる上、化学的にも安定であるなど極めて
有用な充填剤であることを見出し、本発明に至つ
たものである。 Under such circumstances, the present inventors aimed to develop a grafted filler that has specific performance for direct separation of aromatic compound mixtures, is relatively easy to manufacture, and is chemically stable and practical. As a result of continued careful consideration, the general formula [] [In the formula, R 1 , R 2 and R 3 are the same or different,
It represents an alkyl group, an alkoxyl group, a hydroxyl group, or a halogen atom, at least one of which is an alkoxyl group or a halogen atom. ] The chromatographic packing material in which the organosilane shown in the figure is grafted onto an inorganic support having hydroxyl groups on its surface not only shows excellent effects in separating aromatic compounds, but also can be easily produced by ordinary chemical reactions. The present inventors have discovered that it is an extremely useful filler, as it is chemically stable as well as chemically stable.
以下、本発明について詳細に説明する。 The present invention will be explained in detail below.
上記一般式〔〕において、アミノアルキルシ
ラン成分としてはω−アミノアルキルアルコキシ
シランまたはω−アミノアルキルハロゲノシラン
が好ましく、例えばω−アミノプロピルトリエト
キシシラン、ω−アミノプロピルトリクロロシラ
ンなどを挙げることができる。 In the above general formula [], the aminoalkylsilane component is preferably ω-aminoalkylalkoxysilane or ω-aminoalkylhalogenosilane, such as ω-aminopropyltriethoxysilane, ω-aminopropyltrichlorosilane, etc. .
本発明において、ヒドロキシル基をその表面に
持つ無機担体としては例えばシリカゲルなどのシ
リカ含有担体が好ましく、担体の形状は球状、破
枠状などいずれの形状でも差支えないが、高効率
のクロマトグラフ用カラムを得るためにできるだ
け粒径の揃つた微細な粒子が好ましい。 In the present invention, the inorganic carrier having a hydroxyl group on its surface is preferably a silica-containing carrier such as silica gel, and the shape of the carrier may be any shape such as a spherical shape or a broken frame shape. In order to obtain this, it is preferable to use fine particles with as uniform a particle size as possible.
本発明のクロマトグラフ充填剤を調整するには
種々のグラフト方法が採用でき、例えば以下のよ
うな方法が挙げられる。 Various grafting methods can be employed to prepare the chromatographic packing material of the present invention, including the following methods.
その表面にヒドロキシル基を有する無機担体
に、アミノアルキルシランを反応させ、無機担
体の表面にアミノアルキルシリル残基を導入
し、これに３，５−ジニトロ安息香酸クロリド
を反応させる方法。 A method in which an inorganic support having a hydroxyl group on its surface is reacted with an aminoalkylsilane, an aminoalkylsilyl residue is introduced onto the surface of the inorganic support, and this is reacted with 3,5-dinitrobenzoic acid chloride.
具体的には、その表面にヒドロキシル基を有
する無機担体に一般式〔〕
〔式中、R1、R2、R3およびｎは前述と同じ意
味を有する。〕
で示されるアミノアルキルシランを既知の方法
により反応させ、無機担体の表面にアミノアル
キル残基を導入し、次いでこれに式〔〕
で示される３，５−ジニトロ安息香酸クロリド
を反応させることにより、目的の充填剤が得ら
れる。 Specifically, an inorganic carrier having a hydroxyl group on its surface has the general formula [] [In the formula, R 1 , R 2 , R 3 and n have the same meanings as above. ] The aminoalkylsilane represented by the formula [] is reacted by a known method to introduce an aminoalkyl residue onto the surface of the inorganic carrier, and then the aminoalkyl residue of the formula [] The desired filler can be obtained by reacting 3,5-dinitrobenzoic acid chloride represented by
３，５−ジニトロ安息香酸クロリドに、上記
一般式〔〕で示されるオルガノシランを反応
させた後、その表面にフドロキシル基を有する
無機担体にグラフトする方法。 A method in which 3,5-dinitrobenzoic acid chloride is reacted with an organosilane represented by the above general formula [], and then grafted onto an inorganic carrier having a fluoroxyl group on the surface thereof.
具体的には、３，５−ジニトロ安息香酸クロ
リドに一般式〔〕で示されるアミノアルキル
シランを反応させて得られる前記一般式〔〕
で示されるオルガノシランをシリカゲル等の無
機担体にグラフトすることにより、目的の充填
剤が得られる。 Specifically, the above general formula [] obtained by reacting 3,5-dinitrobenzoic acid chloride with an aminoalkylsilane represented by the general formula []
The desired filler can be obtained by grafting the organosilane shown by onto an inorganic carrier such as silica gel.
本発明によつて得られた３，５−ジニトロベン
ゾイルアミノ基を有する充填剤は常法に従つてク
ロマトグラフ用のカラムに充填され、液体クロマ
トグラフイーの固定相として使用される。 The packing material having a 3,5-dinitrobenzoylamino group obtained according to the present invention is packed into a chromatography column according to a conventional method and used as a stationary phase in liquid chromatography.
本固定相を用いる液体クロマトグラフイーにお
いて、適当な溶離条件特に通常よく用いられる順
相分配または逆相分配の条件を選ぶことにより、
芳香族化合物混合物の分離、分析を分離能よく、
かつ短時間で行うことができる。 In liquid chromatography using this stationary phase, by selecting appropriate elution conditions, especially commonly used normal phase distribution or reversed phase distribution conditions,
Separates and analyzes aromatic compound mixtures with high resolution.
And it can be done in a short time.
次に実施例によりさらに詳細に説明する。 Next, a more detailed explanation will be given with reference to examples.
実施例 １
シリカゲル（平均粒径10μｍ、平均孔径60Å、
表面積500m2／ｇ）10ｇを減圧、130℃で４時間乾
燥したのち、３−アミノプロピルトリエトキシシ
ラン20ｇを200mlの脱水トルエンに溶かした液に
加え、60℃にて６時間撹拌する。反応物をろ過
し、残留物をアセトン100mlで洗い、乾燥して３
−アミノプロピルシリル化シリルカゲル（以下
APSと略す）を得た。このものの元素分析値は
Ｎ：1.37％、Ｃ：3.87％であり、これはこのもは
やもの１ｇに対し、３−アミノプロピル基が約
1.0mmolグラフトされたことに相当する。Example 1 Silica gel (average particle size 10 μm, average pore size 60 Å,
After drying 10 g (surface area: 500 m 2 /g) under reduced pressure at 130°C for 4 hours, it was added to a solution of 20 g of 3-aminopropyltriethoxysilane dissolved in 200 ml of dehydrated toluene, and the mixture was stirred at 60°C for 6 hours. The reaction product was filtered, the residue was washed with 100 ml of acetone, and dried.
-Aminopropylsilylated silylka gel (hereinafter referred to as
(abbreviated as APS). The elemental analysis values of this product are N: 1.37% and C: 3.87%, which means that 3-aminopropyl group is about
This corresponds to 1.0 mmol grafted.
次に３，５−ジニトロ安息香酸クロリド2.62ｇ
をとり、脱水テトラヒドロフラン20mlに溶かす。
これに前記APS2.5ｇを加えて懸濁させ、減圧下
で十分脱気したのち、室温で緩やかに５時間撹拌
する。反応物を内径８mmのカラムに移し、テトラ
ヒドロフラン100ml、メタノール250mlおよびクロ
ロホルム100mlをカラム内に流して充填剤を洗つ
たのち、カラムから充填剤を取り出し、エチルエ
ーテル30mlで２回洗い乾燥して３，５−ジニトロ
安息香酸をグラフトした目的の充填剤を得た。こ
のものの元素分析はＮ：2.64％、Ｃ：7.61％であ
り、これはこもの１ｇに対し、３，５−ジニトロ
安息香酸が約0.63mmolグラフトされたことを示
す。このようにして得られた充填剤を内径４mm長
さ25cmのステンレス管にスラリー充填し、次の条
件でメチル馬尿酸のｏ−、ｍ−、ｐ−各異製体お
よび馬尿酸の混合試料を分析し、図−１のクロマ
トグラムを得た。 Next, 2.62 g of 3,5-dinitrobenzoic acid chloride
and dissolve it in 20ml of dehydrated tetrahydrofuran.
2.5 g of the above-mentioned APS is added to this, suspended, thoroughly degassed under reduced pressure, and then gently stirred at room temperature for 5 hours. The reaction product was transferred to a column with an inner diameter of 8 mm, and 100 ml of tetrahydrofuran, 250 ml of methanol, and 100 ml of chloroform were poured into the column to wash the packing material.The packing material was taken out from the column, washed twice with 30 ml of ethyl ether, and dried. A desired filler grafted with 5-dinitrobenzoic acid was obtained. Elemental analysis of this product showed that N: 2.64% and C: 7.61%, which indicates that about 0.63 mmol of 3,5-dinitrobenzoic acid was grafted to 1 g of the material. A slurry of the filler thus obtained was filled into a stainless steel tube with an inner diameter of 4 mm and a length of 25 cm, and a mixed sample of o-, m-, and p-isoforms of methylhippuric acid and hippuric acid was prepared under the following conditions. It was analyzed and the chromatogram shown in Figure 1 was obtained.
温度：室温
移動相：メタノール、水、酢酸混液（95：５：
1.5）
流量：１ml／min
検出器：紫外吸光光度計（波長254nm）
図中−１中、ピーク番号(1)はｏ−メチル馬尿
酸、(2)は馬尿酸、(3)はｍ−メチル馬尿酸、(4)はｐ
−メチル馬尿酸の各ピークである。(4)のピークが
溶出するまでに要する時間は約24分、分離係数
は、(1)と(2)は27.8、(2)と(3)は1.30、(3)と(4)は1.24
であつた。 Temperature: Room temperature Mobile phase: Methanol, water, acetic acid mixture (95:5:
1.5) Flow rate: 1 ml/min Detector: Ultraviolet absorption photometer (wavelength 254 nm) In figure 1, peak number (1) is o-methyl hippuric acid, (2) is hippuric acid, and (3) is m-methyl hippuric acid. Hippuric acid, (4) is p
- Each peak of methyl hippuric acid. The time required for peak (4) to elute is approximately 24 minutes, and the separation coefficients are 27.8 for (1) and (2), 1.30 for (2) and (3), and 1.24 for (3) and (4).
It was hot.
図−１は実施例１において得られたクロマトグ
ラムであり、縦軸は強度を表わし、横軸は保時時
間を表わす。
FIG. 1 is a chromatogram obtained in Example 1, in which the vertical axis represents intensity and the horizontal axis represents retention time.
Claims (1)
アルキル基、アルコキシル基、ヒドロキシル基ま
たはハロゲン原子を表わし、少なくともその一つ
はアルコキシル基またはハロゲン原子である。ｎ
は２、３または４を表わす。〕 で示されるオルガノシランがヒドロキシル基をそ
の表面に持つ無機担体にグラフトされているクロ
マトグラフ充填剤。 ２ 一般式 〔式中、R1、R2およびR3は同一または相異なり、
アルキル基、アルコキシル基、ヒドロキシル基ま
たはハロゲン原子を表わし、少なくともその一つ
はアルコキシル基またはハロゲン原子である。ｎ
は２、３または４を表わす。〕 で示されるオルガノシランがヒドロキシル基をそ
の表面に持つ無機担体にグラフトされているクロ
マトグラフ充填剤を用いて、芳香族化合物混合物
を分離することを特徴とする液体クロマトグラフ
イー分析法。[Claims] 1. General formula [In the formula, R 1 , R 2 and R 3 are the same or different,
It represents an alkyl group, an alkoxyl group, a hydroxyl group, or a halogen atom, at least one of which is an alkoxyl group or a halogen atom. n
represents 2, 3 or 4. ] A chromatographic packing material in which an organosilane represented by the following is grafted onto an inorganic carrier having hydroxyl groups on its surface. 2 General formula [In the formula, R 1 , R 2 and R 3 are the same or different,
It represents an alkyl group, an alkoxyl group, a hydroxyl group, or a halogen atom, at least one of which is an alkoxyl group or a halogen atom. n
represents 2, 3 or 4. ] A liquid chromatography analysis method characterized in that an aromatic compound mixture is separated using a chromatographic packing material in which an organosilane represented by the formula is grafted onto an inorganic carrier having hydroxyl groups on its surface.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59044943A JPS60188843A (en) | 1984-03-08 | 1984-03-08 | Chromatograph packing material and separation of aromatic compound mixture using said material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59044943A JPS60188843A (en) | 1984-03-08 | 1984-03-08 | Chromatograph packing material and separation of aromatic compound mixture using said material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60188843A JPS60188843A (en) | 1985-09-26 |
| JPH0430378B2 true JPH0430378B2 (en) | 1992-05-21 |
Family
ID=12705563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59044943A Granted JPS60188843A (en) | 1984-03-08 | 1984-03-08 | Chromatograph packing material and separation of aromatic compound mixture using said material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60188843A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012240983A (en) * | 2011-05-23 | 2012-12-10 | National Institute Of Advanced Industrial Science & Technology | Surface modification material for immobilizing protein |
-
1984
- 1984-03-08 JP JP59044943A patent/JPS60188843A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012240983A (en) * | 2011-05-23 | 2012-12-10 | National Institute Of Advanced Industrial Science & Technology | Surface modification material for immobilizing protein |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60188843A (en) | 1985-09-26 |
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