Phenyl boronic acid modified silica gel functional chromatographic filler, preparation method and applications thereof

A chromatographic filler and phenylboronic acid-functional technology, which is applied in the field of preparation of phenylboronic acid-modified silica gel functional chromatography fillers, and achieves the effects of novel structure, mild reaction conditions and development promotion.

Inactive Publication Date: 2017-09-05
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, phenylboronic acid-modified silica gel functional chromatography materials based on the mercapto-alkene click reaction have not been reported. The successful preparation of such chromatography materials will provide id

Method used

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  • Phenyl boronic acid modified silica gel functional chromatographic filler, preparation method and applications thereof
  • Phenyl boronic acid modified silica gel functional chromatographic filler, preparation method and applications thereof
  • Phenyl boronic acid modified silica gel functional chromatographic filler, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Weigh 5g of spherical silica gel (particle size 5μm, pore size Specific surface 300m 2 / g), placed in a 250mL three-necked flask, adding 80mL concentration of hydrochloric acid solution of 2mol / L, heated to reflux for 12 hours, cooled to room temperature, with 4 # Suction filter through a sand core funnel, wash with water until neutral, drain and dry in an oven at 80°C overnight to obtain activated silica gel. Under the condition of blowing dry nitrogen, add 50mL of dry toluene to the activated silica gel, stir evenly, then dropwise add 5.9mL of γ-triethoxypropylmercaptosilane, heat and reflux at 110°C for 24 hours, and use 4 # Suction filter the funnel with a sand core, wash it with toluene, acetone, water, and methanol in sequence, drain it and dry it in an oven at 80°C overnight to obtain mercaptosilica gel. Under the condition of passing dry nitrogen, weigh 5g of mercapto silica gel, add 50mL of anhydrous methanol, stir well, add 0.5g of 3-vinylphenylboronic aci...

Embodiment 2

[0053] Weigh 5g of spherical silica gel (particle size 5μm, pore size Specific surface 300m 2 / g), placed in a 250mL three-necked flask, adding 80mL concentration of hydrochloric acid solution of 2mol / L, heated to reflux for 12 hours, cooled to room temperature, with 4 # Suction filter through a sand core funnel, wash with water until neutral, drain and dry in an oven at 80°C overnight to obtain activated silica gel. Under the condition of blowing dry nitrogen, add 50mL of dry toluene to the activated silica gel, stir evenly, then dropwise add 2.6mL of vinyltrichlorosilane, heat and reflux at 50°C for 24 hours, and finish the reaction with 4 # Suction filter the funnel with a sand core, wash it with toluene, acetone, water, and methanol in sequence, drain it and dry it in an oven at 60°C overnight to obtain vinyl silica gel. Under the condition of passing dry nitrogen, weigh 5g of vinyl silica gel, add 50mL of anhydrous methanol, stir evenly, add 0.5g of 4-mercaptophenylbor...

Embodiment 3

[0055] Weigh 3g of the material phenylboronic acid modified filler II in Example 2, put it in a 250mL three-necked flask, add 50mL of anhydrous methanol, stir evenly, add 3g of cysteine ​​dissolved in 5mL of deionized water, stir evenly, add Dissolve 0.06g of 2,2-azobisisobutyronitrile in 5mL of anhydrous methanol, stir well, heat up to 65°C, heat to reflux for 48 hours, cool the reaction system to room temperature, 4 # The funnel with a sand core was subjected to suction filtration, washed with water and methanol in sequence, drained and dried overnight in an oven at 80°C to obtain phenylboronic acid-modified filler III, elemental analysis results: C5.96%, N0.77%, H1.38%, prepared Process such as image 3 shown.

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Abstract

The invention relates to a preparation method and applications of a phenyl boronic acid modified silica gel functional chromatographic filler, wherein Silica Gel is a silica gel, R1 is a phenyl boronic acid derivative, R2 is vinyl or mercapto, R3 is a co-modified modifying group, n is 0-4, and m is 0-3. The present invention provides the preparation method of the chromatographic filler, wherein vinyl or mercapto silane is bonded on the surface of a silica gel by using a modifying reagent such as a silylating agent to obtain an alkenyl or mercapto silica gel, and then the alkenyl or mercapto silica gel and a phenyl boronic acid derivative having mercapto or alkenyl are subjected to a mercapto-olefin click reaction to obtain the phenyl boronic acid modified silica gel functional chromatographic filler. According to the present invention, the preparation method has characteristics of high yield, good repeatability, mild reaction condition, and the like; and the prepared phenyl boronic acid modified silica gel functional chromatographic filler has characteristics of novel structure, a certain hydrophilicity, a certain hydrophobicity and a certain charge responsiveness, can be used as completely-new mixed mode chromatographic filler and the stationary phase, and can be widely used in the separation of various samples.

Description

technical field [0001] The invention relates to the field of chromatographic separation and analysis, in particular to a preparation method and application of a phenylboronic acid-modified silica gel functional chromatographic filler. Background technique [0002] Phenylboronic acid and its derivatives can form reversible five-membered or six-membered cyclic esters with polyols having 1,2- or 1,3-diol groups in alkaline aqueous solution, and this process is reversible [Springsteen G. et al, Tetrahedron, 2002, 58, 5291-5300]. There are a large number of polyhydroxy compounds in nature, such as polysaccharides and other substances, many of which exist in organisms and have an important impact on the life activities of organisms. Therefore, functional materials modified by phenylboronic acid and its derivatives have important research significance for the detection, separation and purification of these compounds in organisms [XuD.et al, Chem.Ind.Eng.Prog.2006,25,1045-1048 ]. ...

Claims

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Application Information

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IPC IPC(8): B01J20/286B01D15/38
CPCB01J20/286B01D15/3804B01J2220/86
Inventor 盛骞莹蓝闽波谭少骏王国华柯燕雄梁鑫淼
Owner EAST CHINA UNIV OF SCI & TECH
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