Preparation And Properties Of S-mandelic Acid Magnetic Imprinted Polymers With Dehydroabietic Acid Derivatives As Functional Monomers

Dehydroabietic acid is a kind of chiral resolution agent with excellent properties.The carboxyl group and benzene ring in the molecular structure of dehydroabioic acid interact with the enantiomer molecules to form hydrogen bonds,dipole-dipole,?-? and so on,so as to achieve the goal of chiral recognition.This paper used dehydroabietic acid or dehydroabietic amine as the raw material to synthesize a series of polymerizable chiral monomers through simple structural modification to prepare magnetic surface molecularly imprinted polymers of s-mandelic acid.The structure and adsorption properties of the polymers are investigated.The main research contents are as follows:(1)Dehydroabietylamine and 12,14-dinitrodehydroabietylamine were used as raw materials to react with acryloyl chloride to obtain N-dehydroabietic acrylamide(DA-FM-1)and N-12,14-dinitrodehydroabietic acrylamide(DA-FM-2).The purity and structure of the products were characterized by HPLC,FTIR and NMR.Dehydroabietic acid was used as raw material to react with 1,2-dibromoethane or 1,4-dibromobutane to obtain dehydroabietic acid-1-bromoethyl ester and dehydroabietic acid-l-bromobutyl ester.And then reacted with 1-vinyl imidazole to obtain brominated-l-vinyl-3-dehydroabietic acid ethyl ester imidazole(DA-FM-3)and brominated-l-ethylene-3-dehydroabietic acid butyl ester imidazole(DA-FM-4).The purity and structure of the product were characterized by TLC and NMR.(2)S-mandelic acid magnetic surface molecularly imprinted polymer(MSMIP)and magnetic non-imprinted polymer(MSNIP)were prepared with-mandelic acid as template molecule,DA-FM-2 as chiral monomer,EGDMA as crosslinking agent,vinyl modified ferroferric oxide as carrier,toluene as porogen.FTIR,XRD,TGA,VSM,SEM were used to characterize the functional structure,thermal stability and magnetic energy.The results show that:The imprinted polymer layer was successfully grafted to the surface of the carrier.MSMIP has hyperparamagnetism and the magnetic saturation intensity is 16.17 emu.g-1.(3)The adsorption properties of MSMIP and MSNIP were studied by HPLC.The results show that:MSMIP has a specific selective adsorption of S-mandelic acid.The adsorption process is more consistent with the multi-layer adsorption Freundlich equation.Scatchard equation indicates that two different binding sitesexist in MSMIP.MSMIP can be used for the separation of mandelic acid,and MSMIP has good recycling performance.