Catalytic synthesis of propionic acid by carboxylation of ethylene with carbon dioxide

Лапидус, А. Л.; Pirozhkov, S. D.; Koryakin, A. A.

doi:10.1007/bf00941114

Cited by 41 publications

(22 citation statements)

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“…Indeed, the use of 5 as the substrate also gave 2 in 71 % yield at 95 % conversion under the standard conditions. Consequently, alcohols can also be used efficiently as substrates: the conversion and product distribution were almost identical to those observed with comparably substituted alkenes ( Table 2, entries [12][13][14][15]. This extension to alcohol substrates widens the potential synthetic scope of the transformations significantly.…”

mentioning

confidence: 71%

“…[9] Furthermore, some examples were reported in which coupling reactions between CO 2 and alkenes, [10] dienes, [11] allenes, [12] or alkynes [13] in the presence of Pd, Ni, or Fe catalysts and superstoichiometric amounts of organometallic reducing agents, such as ZnR 2 , AlR 3 , Grignard reagents, and silanes, gave carboxylic acids after aqueous work up. Most notably, as early as 1978, the formation of propionic acid (38 % yield) from ethene and CO 2 was reported to occur under very drastic conditions (p = 700 bar, T = 180 8C) in the presence of [RhCl-(PPh 3 ) 3 ] and HBr, [14] but details of this transformation remain unknown.…”

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confidence: 99%

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Carbon Dioxide as a C₁ Building Block for the Formation of Carboxylic Acids by Formal Catalytic Hydrocarboxylation

et al. 2013

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Doppelrolle für Rhodium: Für die direkte Synthese von Carbonsäuren aus nicht‐aktivierten Olefinen oder Alkoholen, CO2 und H2 wurde ein effektives katalytisches System gefunden. Detaillierte Analysen und Markierungsstudien ergaben, dass der Gesamtprozess der Hydrocarboxylierung einfacher Olefine aus einer Kombination der umgekehrten Wassergasreaktion (rWGS) mit einem Hydroxycarbonylierungsschritt resultiert, die beide jeweils durch einen Rh‐Katalysator vermittelt werden.

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confidence: 71%

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confidence: 99%

Carbon Dioxide as a C₁ Building Block for the Formation of Carboxylic Acids by Formal Catalytic Hydrocarboxylation

et al. 2013

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“…12) [72]. Notably, as the authors have stated, the methodology had already been disclosed for the hydrocarboxylation of ethylene as early as 1978 under very harsh reaction conditions (700 bar, 180 C) using heterogeneous palladium or rhodium catalysts or [Rh(PPh 3 ) 3 Cl] in the presence of HBr, but without further discussion of the details of this interesting reaction [77]. In Leitner's procedure, the presence of the promoter n-hexyl iodide, an acidic additive such as TsOH, and high reaction temperature (180 C) was required for the conversion of various terminal and internal olefins into the corresponding carboxylic acids in good yields.…”

Section: Reactions With Miscellaneous Transition Metalsmentioning

confidence: 92%

Transition Metal-Catalyzed Carboxylation of Organic Substrates with Carbon Dioxide

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Cazin

et al. 2015

Topics in Organometallic Chemistry

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The development of sustainable chemical processes is a long-standing challenge. Carbon dioxide represents a renewable C1 building block for organic synthesis and industrial applications as an alternative to other common feedstocks which are based on natural gas, petroleum oil, or coal. Apart from the advantages associated with the nontoxicity and abundance of CO 2 , its utilization further enables the reduction in its atmospheric content, which contributes significantly to the greenhouse effect. Although widespread application of CO 2 in organic synthesis -even on an industrial scale -will not be able to fully compensate for the steadily increasing atmospheric quantities produced (mainly by the combustion of fuels), ecological and economical factors make its usage highly desirable. Therefore, tremendous efforts toward activation and utilization of CO 2 have been made by the scientific community over the last 30 years, and, as a result, the number of highly efficient transition metal-catalyzed CO 2 -incorporative reactions has increased dramatically, especially within the last decade. The achievements in the development of sustainable and economic chemical processes for the carboxylation of organic molecules with CO 2 are presented in detail in this chapter.

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“…Although this review is focused on carboxylation processes involving Ni and Fe complexes, it is worth mentioning that the first report dealing with a catalytic hydrocarboxylation of alkenes was reported in 1978 by Lapidus et al [75]. The reaction involved homogeneous and heterogeneous Rh and Pd catalysts, which were capable to carboxylate ethylene with CO 2 under high pressure and temperature (700 atm and 180°C) in the presence of mineral acids.…”

Section: Catalytic Reductive Carboxylation Of Alkenes With Comentioning

confidence: 98%

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

et al. 2016

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The sustainable utilization of available feedstock materials for preparing valuable compounds holds great promise to revolutionize approaches in organic synthesis. In this regard, the implementation of abundant and inexpensive carbon dioxide (CO2) as a C1 building block has recently attracted considerable attention. Among the different alternatives in CO2 fixation, the preparation of carboxylic acids, relevant motifs in pharmaceuticals and agrochemicals, is particularly appealing, thus providing a rapid and unconventional entry to building blocks that are typically prepared via waste-producing protocols. While significant advances have been realized, the utilization of simple unsaturated hydrocarbons as coupling partners in carboxylation events is undoubtedly of utmost academic and industrial relevance, as two available feedstock materials can be combined in a catalytic fashion. This review article aims to describe the main achievements on the direct carboxylation of unsaturated hydrocarbons with CO2 by using cheap and available Ni or Fe catalytic species.

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Catalytic synthesis of propionic acid by carboxylation of ethylene with carbon dioxide

Cited by 41 publications

References 1 publication

Carbon Dioxide as a C₁ Building Block for the Formation of Carboxylic Acids by Formal Catalytic Hydrocarboxylation

Carbon Dioxide as a C₁ Building Block for the Formation of Carboxylic Acids by Formal Catalytic Hydrocarboxylation

Transition Metal-Catalyzed Carboxylation of Organic Substrates with Carbon Dioxide

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

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Catalytic synthesis of propionic acid by carboxylation of ethylene with carbon dioxide

Cited by 41 publications

References 1 publication

Carbon Dioxide as a C1 Building Block for the Formation of Carboxylic Acids by Formal Catalytic Hydrocarboxylation

Carbon Dioxide as a C1 Building Block for the Formation of Carboxylic Acids by Formal Catalytic Hydrocarboxylation

Transition Metal-Catalyzed Carboxylation of Organic Substrates with Carbon Dioxide

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

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Carbon Dioxide as a C₁ Building Block for the Formation of Carboxylic Acids by Formal Catalytic Hydrocarboxylation

Carbon Dioxide as a C₁ Building Block for the Formation of Carboxylic Acids by Formal Catalytic Hydrocarboxylation