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Environmental-Friendly Synthesis of Alkyl Carbamates from Urea and Alcohols with Silica Gel Supported Catalysts

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Environmental-Friendly Synthesis of Alkyl Carbamates from Urea and Alcohols with Silica Gel Supported Catalysts catalysts Article Environmental-Friendly Synthesis of Alkyl Carbamates from Urea and Alcohols with Silica Gel Supported Catalysts Yubo Ma 1,2 , Lei Wang 1,3,*, Xiaodong Yang 4,* and Ronghui Zhang 5 1 School of Chemical Engineering, Chongqing Chemical Industry Vocational College, Chongqing 401220, China; [email protected] 2 Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China 3 Department of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830011, China 4 Institute of Resources and Environment Science, Xinjiang University, Urumqi 830011, China 5 Guangdong Key Laboratory of Intelligent Transportation System, School of Engineering, Sun Yat-sen University, Guangzhou 510275, China; [email protected] * Correspondence: [email protected] (L.W.); [email protected] (X.Y.) Received: 7 October 2018; Accepted: 19 November 2018; Published: 23 November 2018 Abstract: TiO2/SiO2, Cr2O3-NiO/SiO2, and TiO2-Cr2O3/SiO2 were prepared by the impregnation method for alkyl carbamate synthesis using urea as the carbonyl source. Up to 97.5% methyl carbamate yield, 97% ethyl carbamate yield, and 96% butyl carbamate yield could be achieved, respectively. The catalysts were characterized by ICP-AES, BET, XRD, XPS, NH3-TPD, and EPMA. Catalytic activity investigation revealed that TiO2/SiO2, Cr2O3-NiO/SiO2, and TiO2-Cr2O3/SiO2 were effective catalysts for methyl carbamate (MC), ethyl carbamate (EC), and butyl carbamate (BC), respectively. The recycling tests suggested that these silica gel supported catalyst system is active, stable, and reusable. A total of 96–97% alkyl carbamate (methyl, ethyl, and butyl) could be obtained in a 2 L autoclave, and these data suggested that our catalyst system is relatively easy to scale up. Keywords: alkyl carbamate; TiO2/SiO2; TiO2-Cr2O3/SiO2; Cr2O3-NiO/SiO2; urea; alcohol 1. Introduction Alkyl carbamates are important intermediates and end products in the synthesis of a variety of organic compounds [1–3]. For example, it is extensively used for the synthesis of melamine derivatives, polyethylene amine, alkanediol dicarbamates, textile crease-proofing agents [4–8], and itself is also a promising “tranquilizing” drug [9–12]. In the meantime, alkyl carbamates could be used as feedstocks for the synthesis of corresponding organic carbonates such as dimethyl carbonate, diethyl carbonate, dibutyl carbonate, and so on. Significantly, the alkyl carbamate could be used as carbonyl source to replace phosgene for the synthesis of isocyanates [13–16]. Since more than 85% phosgene was consumed in isocyanate industry, this could be the promising usage of carbamates in the future [17]. Various systems have been reported for carbamate synthesis [18–28]. One of the typical methods was the reaction of alcohol and phosgene; however, large amounts of chloroformate ester would be formed during the reaction. Recently, the reaction of alcohol with urea has been more attractive because the ammonia emitted in this process could be easily recycled for synthesis of urea. As well known, urea production is the only way for large scale chemical fixation of carbon dioxide. Thus, carbon dioxide is indirectly used as carbonyl source in the whole process for carbamates synthesis with urea as the carbonyl sources. So, the green and cheap carbonyl source, carbon dioxide, could be successfully used for large-scale industrial process and the green-house gas emission could be reduced. Catalysts 2018, 8, 579; doi:10.3390/catal8120579 www.mdpi.com/journal/catalysts Catalysts 2018, 8, x FOR PEER REVIEW 2 of 18 Catalysts 2018, 8, 579 2 of 16 sources. So, the green and cheap carbonyl source, carbon dioxide, could be successfully used for large-scale industrial process and the green-house gas emission could be reduced. Since the end of the last century, different kinds of solid acidic and basic catalysts such such as as ZnO, MgO, CaO CaO,, and transition metal metal oxides oxides have have been been used used for for the the synthesis synthesis of of carbamates carbamates [4,5, [4,5 ,2121––2828]].. Unfortunately, the low yield towards the desireddesired products and the reusability of the catalyst have been significantsignificant problems problem untils until now. now. In viewIn view of the of practical the practical application, application, the development the development of catalysts, of whichcatalyst shoulds, which be should simple, be active, simple, and active easily, reusable,and easily for reusable, the synthesis for the of synthesis alkyl carbamates of alkyl fromcarbamates urea is highlyfrom urea desirable. is highly desirable. Higher than 80% O O-substituted-substituted carbamate could be achieved M Moreover,oreover, a 10% difference of yield was observedobserved inin differentdifferent autoclaves autoclaves in in our our lab, lab, which which motivated motivated us us to studyto study the the possible possible reason reason for thisfor reaction;this reaction; the composites the composites of autoclave of autoclave were 1Cr9Ni18Ti, were 1Cr9Ni18Ti, which may which beplayed may be a keyplayed for ureaa key conversion for urea andconversion alkyl carbamate and alkyl yield. carbamate Therefore, yield. a seriesTherefore, of catalysts a series containing of catalysts Ti, Cr,containing Ni was preparedTi, Cr, Ni by was the impregnationprepared by the method impregnatio and usedn formethod synthesis and of used alkyl for carbamates. synthesis Theof alkyl catalytic carbamates. performance The of catalytic catalyst forperformance MC synthesis of catalyst is little for effect, MC synthesis while an is obviously little effect, effect while were an observedobviously for effect BC were and ECobserved synthesis. for ThreeBC and different EC synthesis. catalysts Three were different selected catalysts by screening were selected the catalysts by screening containing the catalyst Ti, Cr,s and containing Ni. Three Ti, differentCr, and Ni. catalysts Three different were obtained catalysts for were MC, EC,obtained and BC for synthesis, MC, EC, respectively.and BC synthesis, respectively. More thanthan 98.7%98.7% MCMC yieldyield could could be be achieved achieved in in Ref. ref [27,27], EC EC and and BC BC was was not not studied; studied; the the catalyst catalyst of [2829] was a nano metal oxide and R3N, which was a mixed catalyst, and R3N was dissolved in the reaction system. Therefore, this kind kind of of reaction reaction was was studied studied in in this this work work over over supported supported catalysts catalysts containing containing Ti, Ti,Cr, Cr,and and Ni. Ni. Here, Here, we we report report our our results results about about the the preparation, preparation, characterization characterization and and usage usage of TiO22/SiO22, ,Cr Cr22OO3-3NiO/-NiO/SiOSiO2, 2and, and TiO TiO2-2Cr-Cr2O2O3/SiO3/SiO2 catalysts2 catalysts for for synthesis synthesis of of methyl methyl carbamate carbamate (MC), (MC), ethyl carbamate (EC),(EC), and butyl carbamate (BC) (Scheme(Scheme1 1).). MeOH MeOH H2NCONH2 H2NCO2Me MeOCO2Me 1 2 EtOH EtOH H2NCONH2 H2NCOOEt EtOCO2Et 3 4 BuOH BuOH H2NCONH2 H2NCO2Bu BuOCO2Bu 5 6 SchemeScheme 1.1. Synthesis of methyl, ethyl,ethyl, butylbutyl carbamate/dimethyl,carbamate/dimethyl, diethyl diethyl,, and dibutyl carbonate carbonate.. 2.2. Results and Discussion 2.1. Characterization of Catalysts 2.1. Characterization of Catalysts The catalysts were characterized by ICP-AES, BET, XPS, XRD, TPR, and EPMA. All the catalysts The catalysts were characterized by ICP-AES, BET, XPS, XRD, TPR, and EPMA. All the catalysts prepared and characterized in this work are shown in Table1. prepared and characterized in this work are shown in Table 1. Table 1. Typical physicochemical properties of TiO2/SiO2, Cr2O3-NiO/SiO2, and TiO2-Cr2O3/SiO2 Table 1. Typical physicochemical properties of TiO2/SiO2, Cr2O3-NiO/SiO2, and TiO2-Cr2O3/SiO2 catalysts with different composition. catalysts with different composition. M/Si Surface Pore volume B. E. M/Si atm% Catalyst M/Si 2 Pore3 atom% Bulk Area/mSurface/g /cm /g B./eV E. M/SiSurface atm% Catalyst atom% volume SiO2 Area601/m2/g 0.74 /eV Surface 2.2 wt% TiO2/SiO2-500 Bulk /cm3/g 2.9 wt% TiO2/SiO2-500 Ti/Si 3.8 554 0.69 Ti 2p3/2 459.1 Ti/Si 3.0 2 3.6 wt% TiOSiO2/SiO 2-500 601 0.74 2.23.5 wt wt%% TiO Cr2O23/SiO-8.0 wt%2-500 NiO/SiO2-500 2.97.1 wt wt%% TiO Cr O2/SiO-6.3 wt%2-500 Cr/SiTi/Si 10 3.8 554 0.69 TiCr 2p 2p 3/2 459.1577.6 CrTi/Si /Si 12.6 3.0 2 3 370 0.47 3/2 3.6 wtNiO/SiO% TiO22/SiO-500 2-500 Ni/Si 7.9 Ni 2p3/2 856.6 Ni/Si 7.8 3.5 wt% Cr2O3-8.0 wt% NiO/SiO2-500 Catalysts 2018, 8, x FOR PEER REVIEW 3 of 18 7.1 wt% Cr2O3-6.3 wt% Cr/Si 10 Cr 2p3/2 577.6 Cr /Si 12.6 370 0.47 NiO/SiO2-500 Ni/Si 7.9 Ni 2p3/2 856.6 Ni/Si 7.8 Catalysts 2018, 8, 579 3 of 16 9.0 wt% Cr2O3-3.6 wt% NiO/SiO2-500 1.7 wt% TiO2-4.9 wt% Table 1. Cont. 2 3 2 Cr O /SiO -500 M/Si Surface Pore volume B. E. M/Si atm% Catalyst 1.4 wt% TiO2-6.1 wt% atom%Ti/Si Bulk 2.0 Area/m2/g /cm3/g Ti 2p/eV3/2 458.7 SurfaceTi/Si 2.4 434 0.49 9.0 wt%Cr2O Cr32/SiOO3-3.62-500 wt% Cr/Si 7.9 Cr 2p3/2 577.2 Cr/Si 8.6 NiO/SiO -500 1.0 wt% TiO2 2-8.5 wt% 1.7 wt% TiO2-4.9 wt% CrCr2O2O3/SiO3/SiO2-5002-500 1.4 wt% TiO -6.1 wt% Ti/Si 2.0 Ti 2p 458.7 Ti/Si 2.4 2 434 0.49 3/2 Cr2O3/SiO2-500 Cr/Si 7.9 Cr 2p3/2 577.2 Cr/Si 8.6 2 BET1.0 wt% surface TiO2-8.5 areas wt% and pore volumes of the catalysts are lower than that of pure SiO .
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