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
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 |