JPS60188843A - Chromatograph packing material and separation of aromatic compound mixture using said material - Google Patents
Chromatograph packing material and separation of aromatic compound mixture using said materialInfo
- Publication number
- JPS60188843A JPS60188843A JP59044943A JP4494384A JPS60188843A JP S60188843 A JPS60188843 A JP S60188843A JP 59044943 A JP59044943 A JP 59044943A JP 4494384 A JP4494384 A JP 4494384A JP S60188843 A JPS60188843 A JP S60188843A
- Authority
- JP
- Japan
- Prior art keywords
- packing material
- carrier
- formula
- hydroxyl group
- aromatic compound
- 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.)
- Granted
Links
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)
Abstract
PURPOSE:To enable direct sepn. of an arom. compd. mixture by forming a packing material in such a way that the organosilane expressed by the specific formula is grafted to an inorg. carrier having a hydroxyl group on the surface. CONSTITUTION:The organosilane expressed by the formula is grafted to an inorg. carrier having a hydroxyl group on the surface to form a chromatograph packing material. omega-Aminoalkyl alkoxysilane or omega-aminoalkyl hologenosilane is preferable as the aminoalkyl silane component in the formula and a silica gel- contg. carrier such as silica gel is preferable as the inorg. carrier having the hydroxyl group on the surface. The shape of the carrier may be either spherical or fragmental and the particles having a uniform grain size are preferable to obtain high efficiency.
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
トグラフィーにより分難し、分析する方法に関するもの
である。Detailed Description of the Invention The present invention provides a chromatographic packing material grafted with an organosilane having a 3,5-dinitrobenzoylamino group, and a method for separating and analyzing a mixture of aromatic compounds by liquid chromatography using the packing material. It is about the method.
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 of reacting this with 3,5-dinitrobenzoic acid chloride.
１く８
〔式中・Ｒ１，Ｒ２，Ｒ８およびｎは前述と同じ意味を
有する。〕
アルキル残基を導入し、次いでこれに式（’ＩＩＩ）で
示される３、５−ジニロ安息香酸クロリドリドに一般式
（Ｕ〕で示されるアミノアルキ力
ブ
イ
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。1ku8 [In the formula, R1, R2, R8 and n have the same meanings as above. ] An alkyl residue is introduced into the 3,5-dinylobenzoic acid chloride represented by the formula ('III), and then an aromatic compound mixture is separated and analyzed using an aminoalkyl force buoy represented by the general formula (U). Good 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, the present invention will be explained in more detail with reference to Examples.
実施例１
シリカゲル（平均粒径１０μｍ１平均孔径６０Ａ１表面
積５００ｍ／ｆ ）１０ （／を減圧、１３０°Ｃで４
時間乾燥したのち、８−アミノプロピルトリエトキシシ
ラン２０９を２００１１１ｔの脱水トルエンに溶かした
液に加え、６０°Ｃにて６時間攪拌する。反応物をろ過
し残留物をアセトン１００−で洗い、乾燥して８−アミ
ノプロピルシリル化シリカゲル（以下ＡＰＳと略す）を
得た。このものの元素分析値はＮ・１．３７％、Ｃ：８
．８７％であり、これはこのもの１ｇに対し、３−アミ
ノプロピル基が約１．０ ｍｍｏ ｌ グラフトされた
ことに相当する。Example 1 Silica gel (average particle size 10 μm 1 average pore size 60A 1 surface area 500 m/f) 10
After drying for an hour, 8-aminopropyltriethoxysilane 209 was dissolved in 200111t of dehydrated toluene and stirred at 60°C for 6 hours. The reaction product was filtered, and the residue was washed with 100% acetone and dried to obtain 8-aminopropyl silylated silica gel (hereinafter abbreviated as APS). The elemental analysis value of this product is N・1.37%, C:8
．． 87%, which corresponds to about 1.0 mmol of 3-aminopropyl group grafted to 1 g of this product.
次に８．５−ジニトロ安息香酸クロリド２、６２ ＩＩ
をとり、脱水テトラヒドロフラン２０−に溶かす。これ
に前記ＡＰＳ２．５ｆ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時間攪拌する。反応物
を内径８ｍのカラムに移し、テトラヒドロフラン１００
−、メタノール２５０ｄおよびクロロホルム１００−を
カラム内に流して充填剤を洗ったのち、カラムから充填
剤を取り出し、エチルエーテルｆｌｌＯｄ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１１に対し、３
．５−ジニトロ安息香Ｏが約０．６３ ｍｍｏｌ グラ
フトされたことを示す。Then 8,5-dinitrobenzoic acid chloride 2,62 II
and dissolve it in 20% of dehydrated tetrahydrofuran. The above APS 2.5f 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 m, and tetrahydrofuran 100
-, 250 d of methanol and 100 d of chloroform were flowed into the column to wash the packing material, and then the packing material was taken out from the column, washed twice with ethyl ether fullOd, and dried to obtain the desired material grafted with 3,5-dinitrobenzoic acid. A filler was obtained. The elemental analysis of this is N: 2.64%.
C: 7.61%, which is 3% compared to 11% for Komono.
．． It shows that about 0.63 mmol of 5-dinitrobenzoic acid O was grafted.
このようにして得られた充填剤を内径４＋ｓｍ長さ２５
ｃｒｎ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 −各異性体および
馬尿酸の混合試料を分析し、（４）はｐ−メチル馬尿酸
の各ピークである。The filler obtained in this way has an inner diameter of 4 + sm and a length of 25
The slurry was filled into a CRN stainless steel tube, and a mixed sample of o-, m-, and p-isomers of methylhippuric acid and hippuric acid was analyzed under the following conditions. It is the peak.
（４）のピークが溶出するまでに要する時間は約２４分
、分配係数は、＋１）と（２）は２．７８ 、（２）と
（８）は１．８０ 、 （８）と（４）は１．２４であ
った。The time required for peak (4) to elute is approximately 24 minutes, and the distribution coefficients are 2.78 for +1) and (2), 1.80 for (2) and (8), and 1.80 for (8) and (4). ) was 1.24.
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１１１＋は強度を表わし、横軸は保時時間を表わ
す。
図−１
（４）
０ １０ ２０ ３０ （ｍｉｎ）FIG. 1 is a chromatogram obtained in Example 1, where the vertical axis 111+ represents intensity and the horizontal axis represents retention time. Figure-1 (4) 0 10 20 30 (min)
Claims (2)
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
表わすっ〕 でボ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。(1) General formula [wherein R1, R2 and R8 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 formula is grafted onto an inorganic support having hydroxyl groups on its surface.
す、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ィー分析法。(2) General formula [wherein Rr, R2 and R8 represent the same or different alkyl group, alkoxyl group, hydroxyl group or 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 following 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 true JPS60188843A (en) | 1985-09-26 |
| JPH0430378B2 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) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5717138B2 (en) * | 2011-05-23 | 2015-05-13 | 独立行政法人産業技術総合研究所 | Protein immobilization surface modification material |
-
1984
- 1984-03-08 JP JP59044943A patent/JPS60188843A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0430378B2 (en) | 1992-05-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |