FIGURE CAPTIONS
FIGURE 1 Comparison of the overall atom economy and per pass yield of cyclohexanol/cyclohexanone of the current industrial processes and the novel cyclohexene esterification–hydrogenation process from benzene.
FIGURE 2 (A) Effects of reaction temperature and acetic acid/cyclohexene molar ratio on cyclohexene conversion in cyclohexene esterification, and (B) a plot of lnK against 1/T .
FIGURE 3 Influence of the acetic acid/cyclohexene molar ratio on the esterification rate of cyclohexene at various reaction temperatures. The curves are simulated by the LHHW-type kinetics model.
FIGURE 4 The chromatogram of the hydrogenation products of cyclohexyl acetate over the Cu1Zn1Si2La0.1catalyst.
FIGURE 5 (A) The XRD patterns of the Cu1Zn1Si2 and Cu1Zn1Si2La0.1catalysts, (B) the HRTEM image, (C) the TEM image and particle size distribution histogram, (D) the HAADF–STEM image and the corresponding EDS mappings of (E) Si, (F) Cu, (G) Zn, (H) La, and (I) the overlapping of these elements of the Cu1Zn1Si2La0.1catalyst.
FIGURE 6 (A) The long-term evolutions of the conversion of cyclohexene and the selectivity to cyclohexyl acetate in the esterification of cyclohexene with acetic acid on the pilot-scale reactive distillation reactor. Reaction conditions: reboiler duty of 1050 W, total reflux at ambient pressure, acetic acid feed at the top of the column at 2.59 kg h–1, cyclohexene feed at the middle of the catalytic section at 3.54 kg h–1, and total catalyst loading of 2.65 kg, and (B) the long-term evolutions of the conversion of cyclohexyl acetate and the selectivities to cyclohexanol and ethanol in the hydrogenation of cyclohexyl acetate on the pilot-scale fixed-bed reactor. Reaction conditions: temperature of 473 K, pressure of 6.2 MPa, H2 flow rate of 100 L min–1, cyclohexyl acetate feed rate of 870 g h–1, and catalyst loading of 1.0 kg.