Direct Synthesis of Diallyl Carbonate Via Urea Transesterification with Allyl Alcohol Over Metal Chlorides
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Direct Synthesis of Diallyl Carbonate Via Urea Transesterification with Allyl Alcohol Over Metal Chlorides Dengfeng Wang1 · Xuelan Zhang1 · Hainan Luo1 · Shuwei Wei1 · Xueying Zhao1 Received: 12 October 2018 / Accepted: 26 January 2019 / Published online: 11 February 2019 © Springer Science+Business Media, LLC, part of Springer Nature 2019
Abstract A promising technique was studied towards diallyl carbonate (DAC) manufacture via urea transesterification with allyl alcohol over several metallic chlorides. It was revealed that the intermediate allyl carbamate (AC) was first generated via urea monoalcoholysis with high yield, and subsequently AC further reacted with another allyl alcohol molecule to produce DAC. All the metal halides were evaluated for the overall reaction and the reaction of AC and allyl alcohol, respectively. This work found that the catalytic ability of catalysts originated from metal ions. Importantly, the highest yield of DAC could be achieved using LaCl3 as catalyst. In addition, the activation patterns of reactants were investigated using in situ FT-IR measurement. Based on the characterization results of X-ray power diffraction and elemental analysis of the lanthanum species, separated from the reaction conduced over LaCl3, a possible reaction mechanism was speculated. Graphical Abstract Without catalyst
57.9% yield
O
OH +
H2N
O
NH2
O
O
+ NH3
: LaCl3 +
CO2
Keywords Dially carbonate · Urea · Allyl alcohol · LaCl3
1 Introduction Recently, owing to the continuous depletion of fossil based resources and increasing CO2 concentration in the atmosphere, it is highly desirable to explore a novel strategy to produce more renewable fuels and chemicals [1–3]. In this aspect, organic carbonates that could be synthesized using * Dengfeng Wang [email protected] * Xuelan Zhang [email protected] 1
College of Chemistry, Chemical Engineering and Materials Science, Zaozhuang University, Zaozhuang 277160, People’s Republic of China
CO2 as starting feedstock, have attracted increasing attention from researchers [4, 5]. To date, several methodologies for the synthesis of organic carbonates have been proposed. As the oldest method, the process based on the use of phosgene was phased out owing to high toxicity of phosgene [6]. Oxidative carbonylation of alcohol [7] and transesterification alcohol with alkyl carbonate [8–10] were well known routes with high selectivity to the target product. However, they were limited severely by corresponding disadvantages such as hash reaction conditions or high investment cost which inhibit their expansion of production to desired scale. Currently, an attractive method that synthesis of organic carbonates using C O2 as carbonylation agent is investigated widely because that CO2 is a readily available and environmentally acceptable material with low-price [11]. Nevertheless, this process was far from industrial application owing
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to its poor thermodynamics because of highly stable structure of CO2 [2]. In order to avoid such nega
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