Perspectives on Alkyl Carbonates in Organic Synthesis

Parrish, Jay P.; Salvatore, Ralph Nicholas; Jung, Kyung Woon

doi:10.1016/s0040-4020(00)00671-2

Cited by 205 publications

(115 citation statements)

References 167 publications

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“…A promising and wellknown representative of this compound class is propylene carbonate (PC). Owing to its large liquid temperature range, low price, and high polarity, PC can be used as a solvent in natural gas processing and catalysis, as an electrolyte in lithium batteries, and as a synthetic building block (Parrish et al 2000).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of lignin polyols via oxyalkylation with propylene carbonate

Kühnel

Podschun²,

Saake³

et al. 2014

Holzforschung

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An efficient, nontoxic, and solvent-free oxyalkylation of European beech wood organosolv lignin (OL) has been developed. Two approaches were studied: a direct reaction of lignin with propylene carbonate (PC) and a two-step reaction of lignin with maleic anhydride (MA) followed by oxyalkylation with PC. The structural analysis of lignin polyols was performed by 1 H NMR, 13 C NMR, 31 P NMR, and FTIR spectroscopy. It was demonstrated that PC was able to almost completely oxypropylate aliphatic and phenolic OH groups. Moreover, the carboxylic acid groups of maleated OL were fully oxypropylated by PC. This modification strongly facilitates the generation of a uniform lignin polyol applicable as a biobased component in polyurethanes and polyesters based on cyclic organic carbonates.

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Section: Introductionmentioning

confidence: 99%

Synthesis of lignin polyols via oxyalkylation with propylene carbonate

Kühnel

Podschun²,

Saake³

et al. 2014

Holzforschung

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“…From the viewpoint of environmental protection and resource utilization, it is important to transform CO 2 into useful chemicals efficiently, not only in academia but also for industrial applications. Cyclic carbonates have widely been used for various purposes, such as polar aprotic solvents, intermediates in organic synthesis, monomers for synthesizing polycarbonate, agricultural chemical, alkylating agents, electrolytic elements of lithium secondary batteries and chemical ingredients for preparing medicines [8][9][10][11]. As cycloaddition of CO 2 with epoxides are 100% atom-economical reactions, the synthesis of cyclic carbonates has received increasing attention [3,12,13].…”

Section: Introductionmentioning

confidence: 99%

Ionic Liquids: The Synergistic Catalytic Effect in the Synthesis of Cyclic Carbonates

Cheng

Wang

et al. 2013

Catalysts

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This review presents the synergistic effect in the catalytic system of ionic liquids (ILs) for the synthesis of cyclic carbonate from carbon dioxide and epoxide. The emphasis of this review is on three aspects: the catalytic system of metal-based ionic liquids, the catalytic system of hydrogen bond-promoted ionic liquids and supported ionic liquids. Metal and ionic liquids show a synergistic effect on the cycloaddition reactions of epoxides. The cations and anions of ionic liquids show a synergistic effect on the cycloaddition reactions. The functional groups in cations or supports combined with the anions have a synergistic effect on the cycloaddition reactions. Synergistic catalytic effects of ILs play an important role of promoting the cycloaddition reactions of epoxides. The design of catalytic system of ionic liquids will be possible if the synergistic effect on a molecular level is understood.

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“…Various synthetic methods of organic carbonates by the phosgenation technique using COCl 2 , the oxidative carbonylation of alcohols using CO and transition metals, the reaction of urea with alcohols, the reaction of oxiranes and CO 2 , the reaction of chloroformates, the use of metal carbonate and the organic carbonate interchange reaction have been reported. [1][2][3]9,12,13 However, the main disadvantages of these methods are the use of toxic, gaseous and/or expensive chemicals and requirement for specific additives. The alkoxycarbonylation using organic carbonate and base be also accompanied by the undesired side reaction.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Organic Carbonates with Alkyl/aryl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylates and ROH/AlCl₃under Ambient Condition

Sung¹,

Kim²,

Ryu³

et al. 2014

Bulletin of the Korean Chemical Society

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We demonstrated the synthesis of organic carbonates using alkyl/aryl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylates and alcohol in the presence of aluminum chloride. Alkyl/aryl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylates were reacted with alcohol in the presence of AlCl 3 in toluene at room temperature to afford the corresponding unsymmetric and symmetric organic carbonates in good to excellent yields. These are efficient and convenient processes. Alkyl/aryl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylates are solid, stable and non-toxic CO 2 /CO 2 R(Ar) source. It is noteworthy that the reaction is carry out under an ambient and acidic conditions, the easy-to prepare and readily available starting materials and the quantitative isolation of reusable 4,5-dichloropyridazin-3(2H)-one.

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Perspectives on Alkyl Carbonates in Organic Synthesis

Cited by 205 publications

References 167 publications

Synthesis of lignin polyols via oxyalkylation with propylene carbonate

Synthesis of lignin polyols via oxyalkylation with propylene carbonate

Ionic Liquids: The Synergistic Catalytic Effect in the Synthesis of Cyclic Carbonates

Synthesis of Organic Carbonates with Alkyl/aryl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylates and ROH/AlCl₃under Ambient Condition

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Perspectives on Alkyl Carbonates in Organic Synthesis

Cited by 205 publications

References 167 publications

Synthesis of lignin polyols via oxyalkylation with propylene carbonate

Synthesis of lignin polyols via oxyalkylation with propylene carbonate

Ionic Liquids: The Synergistic Catalytic Effect in the Synthesis of Cyclic Carbonates

Synthesis of Organic Carbonates with Alkyl/aryl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylates and ROH/AlCl3under Ambient Condition

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Synthesis of Organic Carbonates with Alkyl/aryl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylates and ROH/AlCl₃under Ambient Condition