1680-31-5Relevant academic research and scientific papers
Influence of the functionalization degree of acidic ion-exchange resins on ethyl octyl ether formation
Guilera, Jordi,Hanková, Libuse,Jerabek, Karel,Ramírez, Eliana,Tejero, Javier
, p. 14 - 22 (2014)
Ethyl octyl ether (EOE) can be obtained by the ethylation of 1-octanol by means of ethanol or diethyl carbonate over acidic ion-exchange resins. However, EOE formation has to compete with the less steric demanding formation of diethyl ether, by-product obtained from ethanol dehydration or diethyl carbonate decomposition. In the present work, the influence of the resin functionalization degree on EOE formation has been evaluated. A series of partially sulfonated resins (0.87-4.31 mmol H+/g) were prepared by the sulfonation of a macroreticular styrene-divinylbenzene copolymer. The catalysts were characterized, and subsequently, tested in a batch reactor (T = 150 C, P = 25 bar). Amberlyst 15 and 46 were also tested for comparison purposes. Catalytic runs revealed that EOE formation occurred mainly in the firstly sulfonated domain of the polymer skeleton, the least crosslinked; while diethyl ether was formed in the whole polymer bead. Accordingly, the functionalization of the least accessible polymer domain, as a result of increasing the sulfonation temperature or by using a pre-swelling solvent, is not suitable to produce long chain ethers such as EOE; which are preferred as diesel fuels.
Bisimidazolium Tungstate Ionic Liquids: Highly Efficient Catalysts for the Synthesis of Linear Organic Carbonates by the Reaction of Ethylene Carbonate with Alcohols
Huang, Jie,Tao, Huilin,Wang, Yingting,Wu, Shi,Yu, Zhongliang,Zhang, Yongfan
, (2022/03/08)
A series of bisimidazolium tungstate ionic liquids were synthesized and applied to catalyze the reaction of ethylene carbonate (EC) with alcohols. A detailed investigation was carried out on the relationship between catalyst structures and catalytic activities. The result showed that 1-butyl-3-methyl-bisimidazolium tungstate ([Bmim]2WO4) containing double C2–H in bisimidazolium and WO42? had more effectively catalytic performance than other bisimidazolium tungstate and conventional imidazolium salt (OAc?, Cl?, Br?). Under the optimized conditions of 1:15 molar ratio of EC and ethanol, 5?mol% [Bmim]2WO4, 85?°C and 0.5?h, the yield of diethyl carbonate (DEC) was nearly 100%. The detailed DFT calculations and NMR spectroscopy indicated that the high catalytic activity of [Bmim]2WO4 was not only because the strong nucleophilic ability of WO42? could activate ethanol, but also the special structure of double C2–H in bisimidazolium could cooperatively activate EC. The reaction was catalyzed by synergistic effect in double C2–H and WO42? of [Bmim]2WO4. In addition, [Bmim]2WO4 could be used seven times without significant loss of catalytic activity. Graphical Abstract: [Figure not available: see fulltext.]
Method for synthesizing organic carbonate from carbon dioxide, alcohol and brominated alkane under mild conditions
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Paragraph 0016-0017; 0018-0020; 0023-0024, (2020/06/02)
The invention discloses a method for synthesizing organic carbonate from carbon dioxide, alcohol and brominated alkane under mild conditions, belonging to the field of chemical synthesis. According tothe method, carbon dioxide, alcohol and brominated alkane are used as raw materials, 1,8-diazabicycloundec-7-ene (DBU) is used as an activating agent, and acetonitrile is used as a solvent to preparethe organic carbonate. The target product, namely the organic carbonate with excellent yield can be obtained under optimized reaction conditions. The method is mild in reaction conditions, simple andconvenient to operate and high in yield, and is an excellent system for preparing the organic carbonate.
Room temperature and normal pressure preparation method of organic carbonate
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Paragraph 0109-0111, (2020/07/15)
The invention relates to the technical field of organic synthesis, and provides a room temperature and normal pressure preparation method of organic carbonate. The method comprises the following steps: introducing carbon dioxide into an imidazole ionic liquid to obtain a mixture; mixing the obtained mixture with alcohol and halogenated hydrocarbon, and carrying out addition-substitution reactionsto obtain organic carbonate. The whole reaction process is carried out at a room temperature under a normal pressure. The activation energy of the reaction is reduced by using imidazole ionic liquid and halogenated hydrocarbon, and finally, organic carbonate is prepared from CO2 at a room temperature under a normal pressure.
Method of manufacturing Dialkyl carbonate using carbon dioxide
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Paragraph 0073-0079; 0088; 0149-0151, (2019/08/12)
In the embodiment of the present invention consists of a carbon dioxide using the d alkyl car this [thu [thu] which it sees a manufacturing method is provided other [...] number one, alcohol, imidazolium cation and bicarbonate mixing negative catalyst and bases the solvent to form a mixture, said mixture by mixing said reactants including injecting carbon dioxide for generating an agitating the manufacturing method characterized in that the d alkyl car this [thu [thu] which it sees a number [...] substrate. (by machine translation)
Method for preparing dialkyl carbonate by alcoholysis of urea
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Paragraph 0050, (2018/09/08)
The invention relates to a method for preparing dialkyl carbonate by alcoholysis of urea, belonging to the field of chemical synthesis. More specifically, the invention relates to preparation of dialkyl carbonate. The method comprises the following step: subjecting urea and alkyl monohydric alcohol to a reflux reaction under stirring for 6 to 30 hours under the condition of normal pressure or reduced pressure at a reaction temperature of 70 to 150 DEG C by using one or more selected from the group consisting of metal magnesium, calcium, aluminum, chromium, manganese, iron, cobalt, nickel, copper or zinc as a main catalyst and one or more compounds containing donor atom nitrogen, phosphorus, oxygen or sulfur as an auxiliary catalyst so as to prepare the dialkyl carbonate. The preparation method provided by the invention has the following advantages: the dialkyl carbonate is prepared with high selectivity and high yield at a low reaction temperature under the condition of normal pressureor reduced pressure; simple operation, high safety and low cost are achieved in the processing process; and good industrial application prospects are obtained.
Organic carbonate synthesis from CO2 and alcohol over CeO 2 with 2-cyanopyridine: Scope and mechanistic studies
Honda, Masayoshi,Tamura, Masazumi,Nakagawa, Yoshinao,Nakao, Kenji,Suzuki, Kimihito,Tomishige, Keiichi
, p. 95 - 107 (2014/09/17)
The combination system of CeO2-catalyzed carboxylation and 2-cyanopyridine hydration (CeO2 + 2-cyanopyridine system) is effective for the direct synthesis of organic carbonates from CO2 and alcohols. This catalyst system can be applied to various alcohols to afford the corresponding carbonates in high alcohol-based yields. The hydration of 2-cyanopyridine over CeO2 rapidly proceeds under the low concentration of water, which can remove the water from the reaction media. Since the reaction is limited by the chemical equilibrium, the removal of water remarkably shifts the chemical equilibrium to the carbonate side, leading to high carbonate yields. In addition, 2-picolinamide that is produced by hydration of 2-cyanopyridine forms an intramolecular hydrogen bonding between H atom of the amide group and N atom of the pyridine ring, which weakens the adsorption of 2-picolinamide on CeO2 by reduction of the acidity. The reaction mechanism of DMC formation in CeO2 + 2-cyanopyridine system is also proposed.
Mild and efficient capture and functionalisation of CO2 using silver(i) oxide and application to 13C-labelled dialkyl carbonates
Tunbridge, Gemma A.,Baruchello, Riccardo,Caggiano, Lorenzo
, p. 4613 - 4621 (2013/05/08)
A high yielding three-component reaction between β-iodo ethylamine derivatives, MeOH and gaseous CO2 at ambient temperatures and pressures is reported using silver(i) oxide. Unfunctionalised alkyl iodides were also found to be effective in this transformation and their optimisation is also described. To highlight the ease and control with which gaseous CO 2 can be captured and functionalised under mild conditions, the reaction was performed using 13C-enriched CO2 to afford specifically 13C-carbonyl-labelled dialkyl carbonates with exquisite control of the isotopic purity in good yields and without the need for specialised equipment.
Graphite oxide activated zeolite NaY: Applications in alcohol dehydration
Todd, Alexander D.,Bielawski, Christopher W.
, p. 135 - 139 (2013/03/29)
A mixture of graphite oxide (GO) and the zeolite NaY (Si/Al = 5.1) was used to dehydrate various alcohols to their respective olefinic products. Using conditions optimized for 4-heptanol (15 wt% GO-NaY (1 : 1 wt/wt), 150°C, 30 min), a series of secondary and tertiary aliphatic alcohols were cleanly dehydrated in moderate to excellent conversions (27.5-97.2%). Several primary alcohols were also dehydrated, although higher catalyst loadings (200 wt% GO-NaY (1 : 1) and longer reaction times (3 h) were required. The enhanced dehydration activity was attributed to the ability of GO to convert NaY to an acidic form and without the need for ammonium cation exchange and/or high temperature calcination. The Royal Society of Chemistry 2013.
Synthesis of carbonates directly from 1 atm CO2 and alcohols using CH2Cl2
Yamazaki, Yusuke,Kakuma, Kasumi,Du, Ya,Saito, Susumu
experimental part, p. 9675 - 9680 (2011/02/24)
We introduced here a new one-pot, general procedure for the preparation of dialkyl carbonates from alcohols in a straightforward fashion under 1 atm pressure of CO2 using Cs2CO3 and CH 2Cl2 as key reagents.
