Kinetics of catalyzed acid/acid and acid/aldehyde condensation reactions to non-symmetric ketones

Hendren, Travis S.; Dooley, Kerry M.

doi:10.1016/s0920-5861(03)00399-7

Cited by 69 publications

(54 citation statements)

References 25 publications

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“…[62][63][64][65][66][67][68][69][70] Symmetrical ketones such as 3-pentanone, 6-undecanone, and 7-tridecanone have been obtained from ketonization of the appropriate acids. [62,65] This method was applied to the synthesis of nonsymmetrical ketones used as raw materials for pesticides and pharmaceutical products.…”

Section: Acid Condensationmentioning

confidence: 99%

“…[62,65] This method was applied to the synthesis of nonsymmetrical ketones used as raw materials for pesticides and pharmaceutical products. [66][67][68] For example, methylcyclopropylketone and methylnonylketone were produced by the condensation of acetic acid with cyclopropanecarboxilic acid and decanoic acid, respectively. [66] In the reaction of propanoic acid, the reactivity of the carboxylic acid slightly decreased as its chain length was increased, and branched acids were less reactive than linear ones.…”

Section: Acid Condensationmentioning

confidence: 99%

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Ceria‐Based Solid Catalysts for Organic Chemistry

Vivier¹,

Duprez²

2010

ChemSusChem

357

244

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Ceria has been the subject of thorough investigations, mainly because of its use as an active component of catalytic converters for the treatment of exhaust gases. However, ceria‐based catalysts have also been developed for different applications in organic chemistry. The redox and acid–base properties of ceria, either alone or in the presence of transition metals, are important parameters that allow to activate complex organic molecules and to selectively orient their transformation. Pure ceria is used in several organic reactions, such as the dehydration of alcohols, the alkylation of aromatic compounds, ketone formation, and aldolization, and in redox reactions. Ceria‐supported metal catalysts allow the hydrogenation of many unsaturated compounds. They can also be used for coupling or ring‐opening reactions. Cerium atoms can be added as dopants to catalytic system or impregnated onto zeolites and mesoporous catalyst materials to improve their performances. This Review demonstrates that the exceptional surface (and sometimes bulk) properties of ceria make cerium‐based catalysts very effective for a broad range of organic reactions.

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Section: Acid Condensationmentioning

confidence: 99%

Section: Acid Condensationmentioning

confidence: 99%

Ceria‐Based Solid Catalysts for Organic Chemistry

Vivier¹,

Duprez²

2010

ChemSusChem

357

244

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“…[51][52][53][54] Additionally, zeolites (ZSM-5) can be used to form CÀC bonds through alkylation reactions between carbohydrate-derived olefins, [34,55,56] and supported rare-earth oxides (CeO 2 /ZrO 2 ) can be used for CÀC bond formation through ketonization reactions between carbohydrate-derived organic acids. [35][36][37] In addition, we note that long-chain alkanes can be produced by a recently developed process that combines polyol reforming catalysis with Fischer-Tropsch catalysis in a single reactor and thus allows for the direct conversion of glycerol into liquid hydrocarbons that are suitable for diesel applications. [58,59] In this system, the heat necessary for the conversion of glycerol into synthesis gas is supplied by the FischerTropsch reaction, [58,59] thereby offering a less energy-intensive alternative to biomass gasification followed by Fischer-Tropsch and requiring fewer reactors and separations.…”

Section: Directions For Future Research: Process Integration By Catalmentioning

confidence: 99%

“…Another interesting strategy for achieving CÀC coupling between partially oxygenated species involves the ketonization reaction, wherein two acid molecules form a ketone, CO 2 , and H 2 O. [35][36][37] Figure 3 shows this scenario for the case of acetic acid coupling [Eq. (11)].…”

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confidence: 99%

Catalytic Strategies for Changing the Energy Content and Achieving CC Coupling in Biomass‐Derived Oxygenated Hydrocarbons

Simonetti

Dumesic

2008

ChemSusChem

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Fossil fuels are the primary source of energy for modern society. For example, Figure 1 shows the distribution of energy consumption by resource both globally and within the United States. [1][2][3] In 2006, the global energy consumption was 460 exajoules (1 EJ = 10 18 J), of which 87 % was derived from fossil fuel resources (36 % petroleum, 26 % coal, and 23 % natural gas). The US consumed close to 100 EJ, and 85 % of this energy was derived from fossil fuels. Currently, renewable resources account for only 7 % of total energy consumption (both globally and in the US), and nuclear electricity accounts for around 6-8 % of energy consumption. Figure 1 also shows the contribution of the different renewable energy sources to the total amount of renewable energy consumed in the US, with the primary sources being hydroelectricity (45 % of renewables) and traditional biomass (i.e., open combustion; 37 % of renewables). Solar, wind, geothermal, and new biomass contribute 1 %, 4 %, 5 %, and 10 % of the renewable energy, respectively.The distribution of energy consumption for residential, industrial, commercial, transportation, and electrical power sectors in the US is shown in Table 1, along with the distribution of energy consumption for each sector by fuel source.[3] (We focus on energy distributions in the US because these numbers are readily available, and the general trends in the US are similar to those globally.) Industry and transportation consume 30 % each of the total energy in the US, while the commercial and residential sectors consume 20 % each. Residential and commercial energy consumption is primarily in the form of electrical power (70 % and 78 % of the total energy for residential and commercial, respectively). Thus, these two sectors consume primarily coal and natural gas. Only 33 % of industrial energy consumption is in the form of electricity, and this sector consumes almost equivalent energy amounts of coal, natural gas, and oil. Electricity generation accounts for close to 40 % of the total energy consumption in the US. Coal and natural gas supply 40 % and 20 % of electricity, respectively, while oil supplies only 7 %. In contrast to the aforementioned energy sectors, transportation energy is derived almost exclusively from oil (96 %). Renewable energy supplies less than 10 % of the energy to any single sector.The distribution of energy sources amongst the different sectors is listed in Table 2.[3] The majority of coal is consumed by the electrical power sector. Transportation consumes 70 % of the energy provided by oil, while natural gas consumption is distributed amongst industrial, residential, and commerce sectors (primarily to supply heat). Interestingly, Table 2 shows that the use of non-fossil resources (i.e., nuclear, hydro, and other renewables) is concentrated within electricity generation. Similarly, use of solar energy is primarily in the residential sector, likely for heating purposes. Overall, the data in Tables 1 and 2 show that electrical power generation and transportation consume ...

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“…Recently Dooley and co-workers [36,37] reported extensive studies, including isotopic labeling experiments, of the cross-ketonization of acetic acid with decanoic acid and cyclopentane carboxylic acid on supported ceria catalysts. Their results provide strong support for a "ketene mechanism" of ketonization via a surface ketene intermediate.…”

Section: Introductionmentioning

confidence: 99%