The enzymatic reaction−distillation coupling process is a promising technology to realize the chiral resolution of (R/S)-1-phenylethanol with ethyl butyrate and ethanol as acyl donor and byproduct, respectively. In order to design such a coupling process, the vapor−liquid equilibrium (VLE) data are necessary. However, these data were incomplete in literatures. In this work, the isobaric VLE experiments were conducted at 101.3 kPa for the binary systems of 1-phenylethanol + ethyl butyrate, 1-phenylethanol + ethanol, 1-phenylethyl butyrate + ethyl butyrate, 1phenylethyl butyrate + ethanol, and 1-phenylethyl butyrate +1-pheny ethanol. Additionally, the saturated vapor pressure of 1-phenylethyl butyrate was measured in the temperature range 420−500 K and correlated with the Antoine equation. Both the Non-Random Two Liquid (NRTL) and Wilson models were used for the correlation of experimental VLE data. Both models showed satisfactory accuracy, although the Wilson model performed slightly better than the NRTL model. This work would provide important thermodynamic information for the design of enzymatic reaction−distillation coupling process to realize the chiral resolution of (R/S)-1-phenylethanol.

A rational multiscale method is proposed for selecting an economical and sustainable solvent for the direct hydration of cyclohexene. At the molecular scale, liquid-liquid phase equilibrium was estimated using group contribution methods to rapidly screen the potential solvent candidates from a range of organics using a novel evaluation index. At the reactor scale, these candidates were experimentally investigated to pick out the solvents that could significantly improve the conversion, without introducing side reactions and deactivating the catalyst. At the process scale, the total annual cost and CO2 emission were calculated to evaluate the eco-efficiency. Using this new multiscale method, acetophenone was selected as an eco-efficient solvent from over 100 organics, resulting in the reduction of TAC by 7.8% and CO2 emission by 16.9% in the production process. Also, acetophenone led to the increase of cyclohexanol yield from 12.3% to 27.6% without the occurrence of side reactions or catalyst deactivation.

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