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Materials 2019, 12, 350 12 of 22 Fu et al. [182] explored manganese-catalyzed Guerbet-type transformation of ethanol to butanol. This process proceeded selectively to butanol (79%) with the conversion of 12.6% ethanol in the presence of a well-defined manganese pincer complex at 160 ◦C. This was the first report showing the usefulness of non-noble-metal-catalysts for upgrading ethanol into higher alcohol in homogeneous phase. Kulkarni et al. [183] confirmed the excellent catalytic properties of manganese pincer complexes of the type [(RPNP)-MnBr(CO)2] (R = iPr, Cy, tBu, Ph or Ad) for upgrading ethanol to n-butanol. A review by Wu et al. [184] provides a detailed list of heterogeneous and homogenous catalysts used in the processes of valorization of ethanol to butanol, and a summary of the proposed reaction mechanisms for these systems. In particular, catalytic processes running in liquid phase [185] are of great interest to the chemical industry, because of their lower energy requirements and consumption of gas materials. Despite the progress made, however, efficient transformation of bioethanol to butanol in the liquid phase remains a challenge. A particularly stubborn problem is the separation of products from mixtures obtained from industrial installations [186]. One-Step Continuous Process for the Production of Butanol by Catalytic Conversion of Bioethanol in the Sub-/Supercritical State Fluids in the sub-/supercritical state have properties advantageous for many reactions. This is due to their higher diffusion, lower viscosity and increased solubility reaction components event of diversified properties in supercritical media. This very special phase for ethanol is achieved when the pressure and temperature are increased to near or above their respective critical points, 240.7 ◦C and 60.60 atm. [187]. Ghazi Askar and Xu [188] describe a continuous process for the coupling of absolute ethanol (>99%) on a bed of solid catalyst in a pressurized microreactor. The reaction was performed over Ni/Al2O3 (8–27 wt.% Ni) catalysts and on bifunctional catalysts: (Mn2O3/Al2O3 + 27% Ni/Al2O3) and (Mn2O3 + 27% Ni/Al2O3). The rate of conversion and the composition of the products obtained were strongly dependent on the reaction conditions (operating temperature/pressure) and the amount of nickel supported on the catalysts. Generally, higher temperatures/pressures promoted the conversion and production selectivity of butanol. However, if the temperature exceeded 300 ◦C, then more unwanted gaseous products were formed. The most active of the teste catalysts was 8% Ni/Al2O3. The highest selectivity (61.7%), yield of 1-butanol (21.6%) and rate of ethanol conversion (35%) were achieved using a continuous flow fixed-bed reactor and 8%Ni/Al2O3 catalysts with a WHSV of 6.4 h-1 at 250 ◦C under 173.3 atm. Using a self-manufactured flow system, Dziugan et al. [189] investigated the activity of 8–20% Ni/Al2O3 catalysts and a mechanical mixture of 5% Pd-8% Fe/Al2O3 + 8%Ni/Al2O3, in a continuous process for the coupling of raw spirit (83% of ethanol), rectified alcohol (96% of ethanol) and absolute alcohol (>99% of ethanol) into butanol. Although most studies on the continuous production of butanol use absolute alcohol as the substrate, raw spirit and rectified alcohol can also be used. The results showed that the amount of nickel used in the catalysts was not the key factor determining the catalytic performance of such systems. Only a slight increase in butanol yield was observed in systems with higher amounts of nickel. However, X-ray powder diffraction (XRD), scanning electron microscopy-energy dispersive X-ray spectroscopy (SEM-EDS) and total organic carbon (TOC) studies performed before and after the reaction step (after 200 h of ethanol coupling) showed greater stability in the system with the highest amount of nickel (20% Ni/Al2O3). Other tests have been conducted using a two-zone reactor. In a study by Dziugan et al. [189,190], the first zone of the reactor was filled with 8%Ni/Al2O3 and the second with 5%Pd–8%Fe/Al2O3. Metals such as Ni and Pd can act as hydrogen transfer catalysts, promoting both the dehydrogenation of ethanol to aldehydes and hydrogenation of the acetaldehyde condensates to heavier alcohols [191]. Metal oxides supporting Ni and Pd are dehydration catalysts [192]. Separate studies have used bimetallic palladium-iron catalyst, because of its particularly high activity in hydrogen transfer reactions [193–195]. The use of a two-zone reactor contributed to improve the H/C ratio in the liquid fuel biocomponent. The reaction is summarized in Figure 4.PDF Image | Butanol Synthesis Routes for Biofuel Production
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