- Fast aldol-Tishchenko reaction utilizing 1,3-diol monoalcoholates as the catalysts
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The aldol-Tishchenko reaction of enolizable aldehydes is a simple and effective way to prepare 1,3-diol monoesters, which are widely used as coalescing agents in the paint industry. The use of monoalcoholates of 1,3-diols as catalysts gives fast and clean reactions compared with the previous use of several inorganic catalysts. The use of the proper 1,3-diol moiety in the catalyst also reduces the amount of side products which are due to ester interchange between product esters and the catalyst. The rapid water-free method developed herein allows fast preparation of monoesters with excellent yield and minimized formation of side products.
- Toermaekangas, Olli P.,Koskinen, Ari M. P.
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- Trimerization of aldehydes with one α-hydrogen catalyzed by sodium hydroxide
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Trimerization of 2-methylpropanal (isobutyraldehyde) is a simple and effective method to synthesize 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate and 2,2,4-trimethyl-1,3-pentanediol-3-monoisobutyrate which are often used as film forming auxiliaries in paints. The use of solid sodium hydroxide as a catalyst provides an excellent yield of above 85 % after the optimization of the reaction time and the catalyst dosage. Furthermore, trimerization of four other aldehydes with one α-hydrogen catalyzed by solid sodium hydroxide can also take place and the yield of 1,3-diol monoesters reaches 50-70 %. Trimerization of aldehydes with one α-hydrogen can be explained by a three-step reaction mechanism: (i) aldol condensation of aldehyde; (ii) crossed Cannizzaro reaction; and (iii) esterification of carboxylic acid and alcohol.
- Li, Yu-Gang,Luo, Chen-Xi,Qian, Chao,Chen, Xin-Zhi
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p. 422 - 426
(2014/01/06)
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- A method to manufacture a mixture of aliphatic hydroxyesters, especially from isobutyric aldehyde
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A method to manufacture a mixture of aliphatic hydroxyesters, especially from isobutyric aldehyde, is characterized by that the isobutyric aldehyde condensation reaction is carried out in the presence of a mixture of sodium hydroxide and sodium isobutyrate as catalyst in a weight ratio of 3:1, first at 58-60% conversions of isobutyric aldehyde to 2,2,4-trimethyl-1,3-pentanediol isobutyrate at temperatures in the range 58-62°C during 8-12 minutes and then at 68-72% conversions of isobutyric aldehyde to 2,2,4-trimethyl-1,3-pentanediol isobutyrate at temperatures in the range 88-92°C during 3-7 minutes whereupon, from a mixture of 3-hydroxy-2,2,4-trimethylpentyl isobutyrate and 3-hydroxy-2,2-dimethyl-1-(1-methylethyl)propyl isobutyrate, an aqueous solution of the catalyst is separated by allowing to stand and elution from the organic phase of the mixture after the condensation reaction while the process of distillation of the remaining portion of the mixture after the condensation reaction is carried out in four steps.
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Page/Page column 3-5
(2012/04/17)
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- SELECTIVE TRIMERIZATION OF ALIPHATIC ALDEHYDES CATALYZED BY POLYNUCLEAR CARBONYLFERRATES
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Aliphatic aldehydes undergo a catalytic trimerization to give 1,3-diol monoesters upon treatment with Fe3(CO)12 in pyridine or with Fe3(CO)12-pyridine N-oxide in benzene.Polynuclear carbonylferrates serve as catalyst for this transformation.
- Ito, Keiji,Kamiyama, Nobuhiro,Nakanishi, Saburo,Otsuji, Yoshio
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p. 657 - 660
(2007/10/02)
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- Lithium Tungsten Dioxide Promoted Claisen-Tishchenko Condensation of Aromatic and Aliphatic Aldehydes
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Lithium tungsten dioxide, LiWO2, has been shown to be a useful catalyst for effecting the Claisen-Tishchenko condensation of aldehydes under heterogeneous conditions.
- Villacorta, Gilberto M.,Filippo, Joseph San
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p. 1151 - 1154
(2007/10/02)
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