A heteropoly acid catalyst and its convenient, recyclable application to liquid-phase cyclotrimerization of propionaldehyde

Sato, Satoshi; Sakurai, Chisato; Furuta, Hiromi; Sodesawa, Toshiaki; Nozaki, Fumio

doi:10.1039/c39910001327

Cited by 30 publications

(6 citation statements)

References 4 publications

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“…Keggin-type HPAs such as PMo, PW, and SiW catalyze the cyclotrimerization of aldehydes, such as ethanal, propanal, butanal, 2-methylpropanal, etc., to produce 2,4,6,-trialkyl-1,3,5-trioxanes in high yields (eq 17), as reported by Sato et al. , Catalyst turnover number is more than 10 000 for the propanal cyclotrimerization. At high conversions of aldehyde, the reaction mixture spontaneously separates into two phases, a product phase and a catalyst phase, which, depending on aldehyde can be solid or liquid.…”

Section: Other Reactionssupporting

confidence: 58%

Catalysis by Heteropoly Acids and Multicomponent Polyoxometalates in Liquid-Phase Reactions

1998

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ContentsI. Introduction 171 II. Acid Catalysis by Heteropoly Acids 172 A. HPA Catalysts 172 1. Structure 172 2. Acid Properties 173 3. Supported HPAs 175 4. Salts of HPAs 177 B. Homogeneous Reactions 177 1. Hydration of Olefins 178 2. Esterification and Related Reactions 179 3. Condensation 179 4. Miscellaneous Reactions 180 C. Biphasic Reactions 180 1. Polymerization of Tetrahydrofuran 180 2. Esterification 181 3. Other Reactions 181 D. Heterogeneously Catalyzed Liquid-Phase Reactions 181 1. Paraffin Alkylation 182 2. Friedel−Crafts and Related Reactions 182 3. Esterification, Hydrolysis, and Related Reactions 183 4. Miscellaneous Reactions 184 III. Multicomponent Polyoxometalates in Liquid-Phase Oxidation 184 A. Oxidation with Dioxygen 184 1. General Principles 184 2. Homogeneous Oxidation 185 3. Biphasic Oxidation 187 4. Heterogeneously Catalyzed Oxidation 188 5. Mechanism 189 B. Oxidation with Hydrogen Peroxide 191 1. Venturello−Ishii System 191 2. Other Polyoxometalate Systems 193 IV. Conclusion 194 V. Acknowledgments 195 VI. References 195 Ivan V. Kozhevnikov was born in Novosibirsk, Russia. He received his M.Sc. in chemistry from Novosibirsk University in 1969 and Ph.D. from Boreskov Institute of Catalysis (BIC) in 1972, where he studied with Professor E. S. Rudakov. After three years of postdoctoral studies at the Institute of Physicoorganic Chemistry in Donetsk, he returned to BIC and joined Professor K. I. Matveev group. In 1984 he received his D.Sc. degree and was promoted to Head of laboratory at BIC and appointed Professor at Novosibirsk University. He has held visiting positions at Lund University, Sweden (1990),

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Section: Other Reactionssupporting

confidence: 58%

Catalysis by Heteropoly Acids and Multicomponent Polyoxometalates in Liquid-Phase Reactions

1998

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“…In this communication, we report that H 3 PW 12 O 40 is unusually active and recyclable for this reaction in a biphasic system. Similar biphasic catalytic systems have been reported for cyclotrimerization of propionaldehyde catalysed by heteropoly acid 10 and for nitration of benzene by lanthanide triflates. 11 The reaction was performed at 433 K in a stainless steel autoclave (ca.…”

supporting

confidence: 61%

Synthesis of diphenylmethane from formalin and benzene in a biphasic system with 12-tungstophosphoric acid

Hou

Okuhara

2001

Chem. Commun.

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“…2 , at least 13 peaks in the FTIR spectrum of the film correspond to peaks in the spectrum of neat 2,4,6-triethyl-1,3,5-trioxane (including all six of the strongest peaks between 1500 and 900 cm −1 ). Furthermore, previous studies of 2,4,6-triethyl-1,3,5-trioxane report that it phase separates upon formation from propanal/catalyst solutions ( Sato et al, 1993 , 1991 ), consistent with our surface film formation.…”

Section: Resultssupporting

confidence: 92%

Complex chemical composition of colored surface films formed from reactions of propanal in sulfuric acid at upper troposphere/lower stratosphere aerosol acidities

et al. 2015

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Particles in the upper troposphere and lower stratosphere (UT/LS) consist mostly of concentrated sulfuric acid (40–80 wt %) in water. However, airborne measurements have shown that these particles also contain a significant fraction of organic compounds of unknown chemical composition. Acid-catalyzed reactions of carbonyl species are believed to be responsible for significant transfer of gas phase organic species into tropospheric aerosols and are potentially more important at the high acidities characteristic of UT/LS particles. In this study, experiments combining sulfuric acid (H2SO4) with propanal and with mixtures of propanal with glyoxal and/or methylglyoxal at acidities typical of UT/LS aerosols produced highly colored surface films (and solutions) that may have implications for aerosol properties. In order to identify the chemical processes responsible for the formation of the surface films, attenuated total reflectance–Fourier transform infrared (ATR-FTIR) and 1H nuclear magnetic resonance (NMR) spectroscopies were used to analyze the chemical composition of the films. Films formed from propanal were a complex mixture of aldol condensation products, acetals and propanal itself. The major aldol condensation products were the dimer (2-methyl-2-pentenal) and 1,3,5-trimethylbenzene that was formed by cyclization of the linear aldol condensation trimer. Additionally, the strong visible absorption of the films indicates that higher-order aldol condensation products must also be present as minor species. The major acetal species were 2,4,6-triethyl-1,3,5-trioxane and longer-chain linear polyacetals which are likely to separate from the aqueous phase. Films formed on mixtures of propanal with glyoxal and/or methylglyoxal also showed evidence of products of cross-reactions. Since cross-reactions would be more likely than self-reactions under atmospheric conditions, similar reactions of aldehydes like propanal with common aerosol organic species like glyoxal and methylglyoxal have the potential to produce significant organic aerosol mass and therefore could potentially impact chemical, optical and/or cloud-forming properties of aerosols, especially if the products partition to the aerosol surface.

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A heteropoly acid catalyst and its convenient, recyclable application to liquid-phase cyclotrimerization of propionaldehyde

Cited by 30 publications

References 4 publications

Catalysis by Heteropoly Acids and Multicomponent Polyoxometalates in Liquid-Phase Reactions

Catalysis by Heteropoly Acids and Multicomponent Polyoxometalates in Liquid-Phase Reactions

Synthesis of diphenylmethane from formalin and benzene in a biphasic system with 12-tungstophosphoric acid

Complex chemical composition of colored surface films formed from reactions of propanal in sulfuric acid at upper troposphere/lower stratosphere aerosol acidities

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