Crotonaldehyde

Fernández, Jorge Eduardo Chira; Solomons, T. W. Graham

doi:10.1021/cr60219a005

Cited by 10 publications

(5 citation statements)

References 55 publications

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“…Ni is known to be active in both of these hydrogenation reactions, and total hydrogenation process of crotonaldehyde to 1-butanol over Ni catalyst was well established 17) . The vapor pressure of furfural is high enough to apply gas-phase hydrogenation.…”

Section: Ni Catalystsmentioning

confidence: 99%

Supported Metal Catalysts for Total Hydrogenation of Furfural and 5-Hydroxymethylfurfural

Nakagawa

Tamura

Tomishige

2017

J. Jpn. Petrol. Inst.

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Total hydrogenation of furfural and 5-hydroxymethylfurfural (HMF), both of which are important platform chemicals from biomass, produces tetrahydrofurfuryl alcohol (THFA) and 2,5-bis(hydroxymethyl)tetrahydrofuran (BHTHF), respectively, and these products can be used as solvent or raw material of resin. Ni catalysts can give good yields in these reactions; however the low activity and stability are problems. Supported monometallic Pd and Ru catalysts have been reported to be also active in hydrogenation, although the selectivity for total hydrogenation tends to be lower. Other monometallic catalysts such as Cu and Pt generally have low activity in furan ring hydrogenation of furfuryl alcohol (FOL) and 2,5-bis(hydroxymethyl)furan intermediates. We explored various multicomponent catalysts and found that Ni _ Pd/SiO2, Pd _ Ir/SiO2 and Rh _ Ir _ ReOx/SiO2 give good yield of THFA or BHTHF with much higher activity than the mixture of each component supported on SiO2.

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Section: Ni Catalystsmentioning

confidence: 99%

Supported Metal Catalysts for Total Hydrogenation of Furfural and 5-Hydroxymethylfurfural

Nakagawa

Tamura

Tomishige

2017

J. Jpn. Petrol. Inst.

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“…In the present work, the chemical route leading from acetaldehyde to crotonaldehyde (CA) is studied. Crotonaldehyde is an intermediate in many chemical value-added chains and used for producing chemicals like sorbic acid and crotonic acid …”

Section: Introductionmentioning

confidence: 99%

“…1 In the present work, the chemical route leading from acetaldehyde to crotonaldehyde (CA) is studied. Crotonaldehyde is an intermediate in many chemical value-added chains 2 and used for producing chemicals like sorbic acid and crotonic acid. 3 The established production process for obtaining crotonaldehyde from acetaldehyde is described in some detail in ref 3.…”

Section: ■ Introductionmentioning

confidence: 99%

NMR Spectroscopic Study of the Aldoxane Formation in Aqueous Acetaldehyde Solutions

Scheithauer¹,

Grützner

Rijksen

et al. 2014

Ind. Eng. Chem. Res.

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Crotonaldehyde is an interesting intermediate in the chemical industry. It is usually produced from aqueous acetaldehyde in a two step process in which the first step is carried out under basic and the second step under acidic conditions. It is commonly assumed that acetaldehyde is converted in the first step to acetaldol and that acetaldol is subsequently dehydrated in the second step to crotonaldehyde. We demonstrate by 1 H and 13 C NMR spectroscopic studies that acetaldol is hardly present in the reacting solutions at lower temperatures and that the key intermediate is aldoxane (2,6-dimethyl-1,3-dioxane-4-ol). For the first time, data on the chemical equilibrium of the aldoxane formation in aqueous acetaldehyde solutions is provided. Furthermore, preliminary information on the kinetics of that reaction is presented.

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“…The deconjugated isomer is expected to be formed photochemically from the cis-isomer rather than from the trans-isomer for precedent is available for this preference in the ketone series (8). The ready isomerization of 1 in acid accounts for its absence in normal methods for preparation of crotonaldehyde (15) and for the lack of detection by Blacet et al (1). By extrapolation citral and other naturally occurring a,P-unsaturated aldehydes can be expected to isolnerize thermally and with acid.…”

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confidence: 99%

cis-Crotonaldehyde and related compounds

McGreer¹,

Page²

1969

Can. J. Chem.

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Replacement of the hydrochloric acid by acetic acid (1) for making the details of the procedure for the gabe a 74.5 % yield of 1 and no 7, re~lacelnent of synthesis of 1 available to us before publication. the hydrochloric acid by fornlic acid gave a 67 % yield of 1 and a 5 % yield of 7. cis-Crotonaldehyde (1) has been prepared as a mixture with trans-crotonaldehyde (2) by irradiation of 2 with 3000 light. The thermodynamic equilibrium value for 1 to 2 was determined to be 1 :50. Conditions for attaining this equilibrium and the structural factors contributing to its position are discussed.

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Crotonaldehyde

Cited by 10 publications

References 55 publications

Supported Metal Catalysts for Total Hydrogenation of Furfural and 5-Hydroxymethylfurfural

Supported Metal Catalysts for Total Hydrogenation of Furfural and 5-Hydroxymethylfurfural

NMR Spectroscopic Study of the Aldoxane Formation in Aqueous Acetaldehyde Solutions

cis-Crotonaldehyde and related compounds

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