Hydroformylation of Conjugated Dienes

Adkins, Homer; Williams, J. L. R.

doi:10.1021/jo50007a012

Cited by 48 publications

(18 citation statements)

References 7 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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“…Mehrfach ungesattigte Verbindungen mit isolierten, aber nahe beieinanderliegenden Doppelbindungen, wie sie in den mehrfach ungesattigten Fettstoffen vorliegen, ergeben bei der cobaltkatalysierten Hydroformylierung nur Monoaldehyde [22,231. Mehrfach ungesattigte Verbindungen mit isolierten, aber nahe beieinanderliegenden Doppelbindungen, wie sie in den mehrfach ungesattigten Fettstoffen vorliegen, ergeben bei der cobaltkatalysierten Hydroformylierung nur Monoaldehyde [22,231.…”

Section: Hydroformylierung Von 61- Linol-und Linolensauremethylesterunclassified

Hydroformylierung einfach und mehrfach ungesättigter Fettstoffe mit heterogenisierten Cobaltcarbonyl‐ und R

1996

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Mit Hilfe von heterogenen Cobaltcarbonyl‐ und Rhodiumcarbonyl‐Festphasenphosphan‐Katalysatorsystemen können einfach und mehrfach ungesättigte Fettstoffe in chemisch‐technisch einfacher und befriedigender Weise zu industriell interessanten Zwischenprodukten hydroformyliert werden. Die eingesetzten, festen tert. Phosphan‐Komplexliganden haben ein silikatisches Grundgerüst und sind deshalb auch für die bei höheren Temperaturen verlaufende, cobaltkatalysierte Hydroformylierung geeignet. Die cobaltkatalysierte Reaktion führt wegen der Doppelbindungsisomerisierung auch bei mehrfach ungesättigten Fettstoffen zu nur monofunktionalisierten Fettsäureketten. Die rhodiumkatalysierte Reaktion dagegen liefert aus Linol‐ und Linolensäurederivaten von Mono‐ und Diformylderivaten dieser Fettstoffe bestehende uneinheitliche Gemische, so daß die Rhodiumcarbonyl‐Festphasenphosphane eher für die Hydroformylierung einfach ungesättigter Verbindungen geeignet erscheinen. Dies gilt auch für die ebenfalls untersuchten Rhodiumcarbonyl‐supported aqueous phase‐Katalysatoren, die sich bei der Hydroformylierung mehrfach ungesättigter Fettstoffe ähnlich wie das Rhodium‐Festphasenphosphan‐System verhalten. Richtige Reaktionsführung vorausgesetzt, d.h. batch‐Arbeitsweise und vollständiger Olefinumsatz, sind die Metallverluste vernachlässigbar gering.

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“…in 1952: hence, cyclopentane carbaldehyde was obtained as a main product in cobalt-catalyzed hydroformylation with 37% yield at 145-155 • C and 255 bar synthesis gas [18].…”

Section: Introductionmentioning

confidence: 99%