Synthesis Of1-fatty Acid-3-chloropropanol Esters And Preliminary Detection Of Chloropropanol Esters Of High Performance Liquid Chromatography-fluorescence

1-fatty acid-3-chloropropanol esters were synthesized with epichlorohydrinand fatty acids catalyzed by chromium（III） acetate in2-methoxyethyl ether．Thestructures of the synthetic products were determined by Fourier transform infraredspectroscopy （FTIR）， High performance liquid chromatography （HPLC），Electrospray ionization mass spectrometry（ESI-MS）．1-fatty acid-3-chloropropanolesters of high purification which could be used as standards in the following studywere obtained by ODS column chromatography． Because of the complexity ofoperation and high cost of the purification by column chromatography， newzeolite-encapsulated catalysts have been studied． The formed zeolite catalystsadded with chromium showed good catalytic effect and was easy to seperate．Doping Cr ions on HZSM-5zeolite by ion exchange，so the addition reaction ofepichlorohydrin with fatty acids to produce1-fatty acid-3-chloropropanol esterscould be of high selectivity．The existing methods such as Gas chromatography-mass spectrometry （GC-MS）， liquid chromatography-time of flight massspectrometry（LC-TOFMS） and other methods of the fatty acid chloropropanolesters detection need more expensive equipment， higher usage and maintenancecosts．Thus，the method of fatty acid chloropropanol esters detection by liquidchromatography only was studied． The affecting factors of hydrolysis andextraction influencing factors of3-MPCDE were studied．Finally,the hydrolyzedand extracted3-MPCD was detected by High performance liquid chromatography-fluorescence（HPLC-FLD）．The main contents of this paper are as follows：（１）1-fatty acid-3-chloropropanol esters were synthesized by palmitic acid，lauric acid，stearic acid，myristic acid，oleic acid，linoleic acid，n-octanoic acid，n-decanoic acid with epichlorohydrin， chromium acetate （III） catalyzed ringopening of epichlorohydrin． Detection onditions of liquid chromatography wereoptimized． Reaction temperature，reaction time，catalyst amount，palmitic acid /epichlorohydrin molar ratio of synthesis reaction were optimized． The optimalreaction conditions as follows：reaction temperature80℃，reaction time30h，theamount of catalyst8mmol/L，palmitic acid/epichlorohydrin molar ratio of1：1.2．（２） The synthesied1-fatty acid-3-chloropropanol esters eluting withmethanol and water were isolated and purified by ODS column．Structures of thepurified1-fatty acid-3-chloropropanol esters were determined by Fouriertransform infrared scanning，Liquid chromatography electrospray ionization massspectrometry．（３）Doped with other metal ions，new catalysts were formed by ion exchangingon HZSM-5zeolite． Catalytic properties and reusability on1-fattyacid-3-chloropropanol esters synthesis reaction of new catalysts were investigated．Optimal conditions of doped zeolites: zeolite load Cr ions, sintering temperature500℃，optimum amount of catalyst was1.0g/30mL reaction solution，zeolitereactivation with soaking solution of5%H2SO4, sintering temperature500℃.（４）Factors that affect3-MPCDE hydrolysis and extraction in indirect methodwere studied．Effects of extraction solvent，concentration of NaCl，concentrationof acetate（the reaction ends solvent）after alkaline hydrolysis were studied．Todetermine the optimum conditions：n-heptane as extraction solvent， concentrationof NaCl was0.01g/mL， concentration of acetic acid is100μL/(30mLNaClsolution)．The effects of the salt ions，pH，impact of direct extraction and drynitrogen on HPLC detection after acid hydrolysis were examined． The resultsshowed that the hydrolysis was stopped after the pH was adjusted to neutral，driedwith nitrogen and then to go through the sample extraction，the aqueous phase wasextracted with water． Fatty acid chloropropanol esters in several commerciallyavailable vegetable oil were determined preliminarily by high performance liquidchromatography-fluorescence(HPLC-FLD)．...