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Non-interpenetrating chiral MOF stationary phase, its preparation method and application in enantiomer separation in HPLC

A stationary phase, chiral technology, applied in the fields of metal organic compounds, analytical chemistry, and material synthesis, to achieve the effects of mild conditions, simple synthesis process, and easy availability of raw materials

Inactive Publication Date: 2013-10-02
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, for a certain type of chiral column, only one or several chiral compounds have chiral resolution ability, and there is no such thing as reversed-phase C18 column, which has a wide range of universality for many separation samples.
In addition, there are still challenges in the preparation of chiral zeolite molecular sieve stationary phases with high specific surface area, uniform pore structure and size, and the selectivity of resolution depends on the pore size of the stationary phase and the molecular size of the resolved molecules.

Method used

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  • Non-interpenetrating chiral MOF stationary phase, its preparation method and application in enantiomer separation in HPLC
  • Non-interpenetrating chiral MOF stationary phase, its preparation method and application in enantiomer separation in HPLC
  • Non-interpenetrating chiral MOF stationary phase, its preparation method and application in enantiomer separation in HPLC

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]Add 1.0 g of L-leucine, 0.5 g of sodium carbonate, 1.0 g of 4-formylpyridine and 5 mL of methanol to 30 mL of water in sequence, stir at room temperature for 1 h; cool in an ice bath, then slowly add 5 g of sodium borohydride aqueous solution , continue to stir for 0.5h; acidify with hydrobromic acid to pH 3, continue to stir for 1h; then, distill under reduced pressure to a solid state; extract 3 times with 10mL of methanol, filter, and rotate the filtrate to obtain the chiral ligand 1 -HL; the sodium borohydride aqueous solution, the mass fraction of sodium borohydride is 7%.

[0035] Add 0.4g of the synthesized chiral ligand l-HL and 0.25g of zinc acetate to 10mL of secondary ionized water, place it in a small beaker, and put the small beaker into a large beaker containing 50mL of methanol, seal it , diffused at room temperature for 2.5 days, filtered the crystallized mixed solution in a small beaker, and washed the filtered crystals with 7.5 mL of methanol aqueous so...

Embodiment 2

[0037] Add 1.5g of L-leucine, 1.0g of sodium carbonate, 2.0g of 4-formylpyridine and 10mL of methanol to 40mL of water in sequence, stir at room temperature for 2h; cool in an ice bath, then slowly add 10g of sodium borohydride aqueous solution , continue to stir for 1 h; acidify with hydrobromic acid to pH 4.5, continue to stir for 2 h; then, distill under reduced pressure to solid state; extract 3 times with 20 mL of methanol respectively, filter, and rotate the filtrate to obtain the chiral ligand l- HL; the sodium borohydride aqueous solution, the mass fraction of sodium borohydride is 11%.

[0038] Add 0.4g of the synthesized chiral ligand l-HL and 0.25g of zinc acetate to 10mL of secondary ionized water, place it in a small beaker, and put the small beaker into a large beaker containing 50mL of methanol, seal it , diffused at room temperature for 2.5 days, filtered the crystallized mixed solution in a small beaker, and washed the filtered crystals with 7.5 mL of methanol...

Embodiment 3

[0040] Add 3.0g of L-leucine, 1.5g of sodium carbonate, 3.0g of 4-formylpyridine and 15mL of methanol to 50mL of water in sequence, stir at room temperature for 3h; cool in an ice bath, then slowly add 15g of sodium borohydride aqueous solution , continue to stir for 1.5h; acidify with hydrobromic acid to pH 6, continue to stir for 3h; then, distill under reduced pressure to a solid state; extract 3 times with 30mL of methanol, filter, and rotate the filtrate to obtain the chiral ligand 1 -HL; the sodium borohydride aqueous solution, the mass fraction of sodium borohydride is 15%.

[0041] Add 0.4g of the synthesized chiral ligand l-HL and 0.25g of zinc acetate to 10mL of secondary ionized water, place it in a small beaker, and put the small beaker into a large beaker containing 50mL of methanol, seal it , diffused at room temperature for 2.5 days, filtered the crystallized mixed solution in a small beaker, and washed the filtered crystals with 7.5 mL of methanol aqueous solut...

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Abstract

The invention relates to a non-interpenetrating chiral MOF (metal organic framework) stationary phase, its preparation method and application in enantiomer separation in HPLC (high-performance liquid chromatography). The stationary phase is a non-interpenetrating chiral three-dimensional porous framework complex with a structural formula as {[ZnL].H2O}n. An asymmetric structural unit {[ZnL].H2O} of the complex is composed of a Zn<2+>, an L ligand and a guest water molecule. The L ligand is -NH- containing chiral pyridine carboxylic acid, its chemical composition is [(N-(4-pyridylmethyl)-L-leucine.HBr)], and its molecular formula is C12H19BrN2O2. Chiral amino acid and 4-pyridylaldehyde are selected as raw materials to synthesize the-NH- containing pyridine carboxylic acid chiral ligand by a one-step process. The ligand and zinc acetate are adopted as raw materials to undergo room temperature diffusion so as to obtain the MOF stationary phase. The material provided in the invention has uniform chiral helical channel, uniform aperture and orifice, and can be used for separation of chiral drugs and other enantiomers. The separation is selectively dependent on the size of a separated enantiomer molecular size, but is not dependent on the functional group of the separated enantiomer. Thus, the non-interpenetrating chiral MOF stationary phase has the characteristics of traditional zeolite molecular sieve separation.

Description

technical field [0001] The invention relates to an optical homochiral metal-organic framework (MOF) stationary phase, a preparation method thereof, and an application in splitting enantiomers, belonging to the technical fields of metal-organic compounds, material synthesis, and analytical chemistry. Background technique [0002] Enantiomers refer to two stereoisomers that are real objects and mirror images, but cannot completely overlap, referred to as enantiomers, also known as optical isomers or mirror images. The corresponding molecules are called chiral molecules and the corresponding compounds are called chiral compounds. [0003] Enantiomers have significant performance differences in biological activity, pharmacology and toxicology, such as enantiomers of chiral drugs, usually exhibit different physiological activities, one of which has a response characteristic of stimulating or inhibiting a certain function, And the other has no or weak or has the opposite response...

Claims

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Application Information

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IPC IPC(8): B01J20/29B01J20/30C07B57/00C07C57/30C07C51/47C07C49/83C07C45/79C07C33/22C07C29/74C07C209/88C07C211/27C07F3/06
Inventor 唐波马瑜匡轩苏浩
Owner SHANDONG NORMAL UNIV
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