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Author: search.filters.author.Resasco, Daniel E.Subject: search.filters.subject.Aldol condensation

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    Condensation reactions of propanal over CexZr 1-xO2 mixed oxide catalysts
    (2010-09-15)
    Gangadharan, Anirudhan
    ;
    Shen, Min
    ;
    Sooknoi, Tawan
    ;
    Resasco, Daniel E.
    ;
    Mallinson, Richard G.
    Vapor phase condensation reactions of propanal were investigated over Ce<inf>x</inf>Zr<inf>1-x</inf>O<inf>2</inf> mixed oxides as a model reaction to produce gasoline range molecules from short aldehydes found in bio-oil mixtures. Several operating parameters were investigated. These included the type of carrier gas used (H<inf>2</inf> or He) and the incorporation of acids and water in the feed. Propanal is converted to higher carbon chain oxygenates on Ce <inf>x</inf>Zr<inf>1-x</inf>O<inf>2</inf> by two pathways, aldol condensation and ketonization. The major products of these condensation reactions include 3-pentanone, 2-methyl-2-pentenal, 2-methylpentanal, 3-heptanone and 4-methyl-3-heptanone. It is proposed that the primary intermediate for the ketonization path is a surface carboxylate. The presence of acids in the feed inhibits the aldol condensation pathway by competitive adsorption that reduces the aldehyde conversion. Water also promotes ketonization and inhibits aldol condensation by increasing the concentration of surface hydroxyl groups that enhance the formation of surface carboxylates with the aldehyde. Hydrogen enhances cracking and production of light oxygenates and hydrocarbons. The light oxygenates may in turn be reincorporated into the reaction path, giving secondary products. However, the hydrocarbons do not react further. Analysis of the fresh and spent catalysts by XPS showed varying degrees of reduction of the oxide under different operating conditions that were consistent with the reaction results. Changing the proportion of the parent oxides showed that increased Zr favored formation of aldol products while increased Ce favored ketonization. This occurs by shifting the balance of the acid-base properties of the active sites. © 2010 Elsevier B.V.
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    A comparison of the reactivities of propanal and propylene on HZSM-5
    (2010-05-04)
    Hoang, Trung Q.
    ;
    Zhu, Xinli
    ;
    Sooknoi, Tawan
    ;
    Resasco, Daniel E.
    ;
    Mallinson, Richard G.
    The reactivities of propanal and propylene have been compared over HSZM-5 zeolites (Si/Al = 45 and 25). Propanal is found to be much more reactive than propylene and to form mostly 2-methyl-2-pentenal and C<inf>9</inf> aromatics as early products in the reaction network. Propylene, in contrast, requires more severe conditions to form C<inf>6</inf> and C<inf>7</inf> aromatics. It is proposed that propanal undergoes acid-catalyzed aldol condensation to form 2-methyl-2-pentenal. This dimer undergoes further condensation to form the aldol trimer, which subsequently dehydrates and cyclizes into C<inf>9</inf> aromatics. In contrast, it is well known that propylene, like other olefins, undergoes aromatization via oligomerization and formation of a hydrocarbon pool. While in the conversion of propanal, propylene is also produced, it appears that it does not play a major role in the formation of aromatics under conditions of shorter space times and lower temperatures, at which propanal produces aromatics in significant amounts. © 2010 Elsevier Inc. All rights reserved.
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    Oligomerization of propionaldehyde on novel basic catalysts
    (2008-12-01)
    Amen, Q. V.
    ;
    Sooknoi, T.
    ;
    Lobban, L. L.
    ;
    Mallinson, R. G.
    ;
    Resasco, Daniel E.
    Vapor-phase oligomerization of propanal to 2-methyl-2-pentenal and 2-ethyl-3,5-dimethylcyclo-2-pentenone over basic zeolite catalysts (NaX, KNaX, KX, and CsNaX), as well as more traditional solid basic catalysts (MgO and MgO-Al2O3 hydrotalcites), was studied in an integral flow reactor at atmospheric pressure. Conversion and carbon yield based on catalyst properties (basicity, acidity) are reported. The highest stable activity was over KX, with the highest selectivity to the primary product, 2-methyl-2-pentenal (dehydrated aldol dimer of propanal) and the second highest selectivity to the secondary product, 2-ethyl-3,5-dimethylcyclo-2-pentenone (a non-aromatic cyclic trimer), with essentially no other products. Promotion of Zeolite X with various alkali metals also affected the acid and base site strengths, which had an effect on the conversion and selectivity.