动力学控制结晶法拆分1,1'-联二萘酚工艺研究

The Modified Resolution Process of 1,1'-Binaphthanol by Kinetic Control Crystallizing

对外消旋1,1'-联二萘酚(BINOL)的拆分进行了研究。采用动力学控制结晶的方法改进了(S)-2-吡咯烷酮-5-羧酰苯胺拆分BINOL的工艺,得到一种实用有效的获得光学纯BINOL的方法。采用该方法可以同时得到BINOL的R和S两种异构体,它们的ee值均大于99%。采用正交实验的方法研究了反应时间、拆分剂用量、溶剂组成以及溶剂体积在拆分过程中对(R)和(S)-BINOL的产率的影响。在最佳条件下,(R)-BINOL和(S)-BINOL的收率分别为18.0%和35.2%,外消旋BINOL的回收率为58.8%,拆分剂的回收率为68.6%。

The resolution process of racemic 1,1 ＇- binaphthol （BINOL） is studied in this article. An efficient and practical method to directly resolve racemic 1,1 ＇- binaphthol（BINOL） into optically pure BINOL has been developed by modification of a （ S ） - 2 - pyrrolidone - 5 - carboxyanilide resolution procedure. Both enantiomers （R and S） of BINOL can be easily obtained with this method and the ee value is more than 99.5%. And the effects of the reaction time, the quantity of chiral reagent, the composition and volume of solvent on the yield of each enantiomer were examined via orthogonal experiment. Under the optimal conditions, the yield of （ R ） - BINOL and （S） - BINOL are 18.0% and 35.2% respectively, recovery of rac - BI- NOL and （ S ） - 2 - pyrrolidone - 5 - carboxyanilide are 58.8% and 68.6% respectively.