Dialdehydes by hydroformylation of conjugated dienes

Fell, Bernhard; Rupilius, Wolfgang

doi:10.1016/s0040-4039(01)88252-6

Cited by 46 publications

(28 citation statements)

References 4 publications

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“…Many research groups investigated hydroformylation of butadiene experimentally. In recent decades, however, the selectivity for adipic aldehyde has been low, which has led to further research . The highest reported selectivities to adipaldehyde in butadiene hydroformylation so far is 50 % .…”

Section: C4 Moleculesmentioning

confidence: 99%

“…However, by using 1,3-dienes, such as butadiene, various very interesting products can be formed under typical hydroformylation reaction conditions. (E/Z)-3pentenal and 4-pentenal [44][45][46][47][48][49][50] are attractive intermediates for the production of valuable C6 compounds such as adipic acid, hexamethylenediamine and 1,6-hexanediol via the selective conversion of 1,6-hexanedial (adipaldehyde) as a central intermediate ( Figure 19). [51][52][53] Many research groups investigated hydroformylation of butadiene experimentally.…”

Section: 2 Carbonylationmentioning

confidence: 99%

“…In recent decades, however, the selectivity for adipic aldehyde has been low, which has led to further research. [45][46][47][48][49][50][51][52][53][54][55] The highest reported selectivities to adipaldehyde in butadiene hydroformylation so far is 50 %. [56] The use of chelating bisphosphite ligands, as congeners of the bisphosphine triptyphos (TTP), and rhodium-based catalysts shows high n-selectivity in reactions of 1-alkenes.…”

Section: 2 Carbonylationmentioning

confidence: 99%

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Homogeneously Catalyzed 1,3‐Diene Functionalization – A Success Story from Laboratory to Miniplant Scale

et al. 2018

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For many years, the efficient use of resources has been a major and permanent challenge for the chemical industry. The implementation of alternative resources such as renewables and carbon dioxide has been a subject of considerable discussion, but also the more efficient use of long known bulk chemicals is of great interest. Among them, 1,3‐dienes such as 1,3‐butadiene from the C4 cut of the naphtha cracker as well as isoprene, piperylene and cyclopentadiene from the corresponding C5 section are important substrates. These dienes are presently employed in various markets, with the greatest importance being in the production of polymers and copolymers. However, homogeneous transition metal catalysis has proven to be a versatile tool to functionalize these important 1,3‐dienes to low molecular weight fine chemicals by introducing, for example, nitrogen, oxygen or silicon. Hence, an upgraded use of the corresponding products as agrochemicals, pharmaceuticals, fragrances or special detergents is close at hand. The main approaches in the topic of homogeneous functionalization reactions of the industrially relevant 1,3‐dienes will be summarized and discussed within the present article. Besides that, novel applications including renewable 1,3‐dienes, for example β‐myrcene and β‐farnesene, as well as the application of CO2 in telomerization, will be critically discussed.

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Section: C4 Moleculesmentioning

confidence: 99%

Section: 2 Carbonylationmentioning

confidence: 99%

Section: 2 Carbonylationmentioning

confidence: 99%

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Homogeneously Catalyzed 1,3‐Diene Functionalization – A Success Story from Laboratory to Miniplant Scale

et al. 2018

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“…4 Over the course of investigation, rhodium has turned out to be the most active and commonly used catalyst metal for the majority of hydroformylation reactions. [5][6][7][8] Conjugated dienes may form an intermediate η 3 -complex with the metal centre instead of the desired η 1 -complex, which is nonreactive in hydroformylation. [5][6][7][8] Conjugated dienes may form an intermediate η 3 -complex with the metal centre instead of the desired η 1 -complex, which is nonreactive in hydroformylation.…”

Section: Introductionmentioning

confidence: 99%

“…5,20 As usual, the use of cobalt as the metal catalyst needs severe conditions, as it does in piperylene hydroformylation (200 bar synthesis gas, 150°C). Its application, if any, has been to serve as a model compound during the investigation of other dienes.…”

Section: Introductionmentioning

confidence: 99%

Hydroformylation of piperylene and efficient catalyst recycling in propylene carbonate

2015

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In contrast to monoolefins, diene hydroformylation is still a demanding task. Some dienes like butadiene and isoprene have been investigated more intensively, however, 1,3-pentadiene ( piperylene) has been rarely investigated. Here, we present a systematic investigation of the hydroformylation of piperylene, using Rh(CO) 2 acac/Xantphos as an active catalyst which can be easily recycled in the green solvent propylene carbonate. Under the chosen conditions aldehyde yields of up to 82% have been obtained, while catalyst recycling was possible for up to six runs.Scheme 1 Hydroformylation of a terminal olefin.

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Sodium Tetracarbonylcobaltate

Kerr

2001

Encyclopedia of Reagents for Organic Synthesis

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Dialdehydes by hydroformylation of conjugated dienes

Cited by 46 publications

References 4 publications

Homogeneously Catalyzed 1,3‐Diene Functionalization – A Success Story from Laboratory to Miniplant Scale

Homogeneously Catalyzed 1,3‐Diene Functionalization – A Success Story from Laboratory to Miniplant Scale

Hydroformylation of piperylene and efficient catalyst recycling in propylene carbonate

Sodium Tetracarbonylcobaltate

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