First methoxycarbonylation of the renewable β-myrcene: high selectivity through reduced isomerisation

Behr, Arno; Johnen, Leif; Wintzer, Andreas; Willstumpf, Andreas; Dinges, Michael

doi:10.1039/c3cy20734j

Cited by 12 publications

(3 citation statements)

References 21 publications

(38 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It was observed that the most important side reaction is the isomerization of limonene 1 to its isomer isoterpinolene 4. The isomerization effect was already observed in the methoxycarbonylation of myrcene [32] which was performed under similar reaction conditions. Furthermore, the hydrogenation of the starting material to 3-menthene 5 was observed caused by the hydrogen in the reaction system.…”

Section: Resultsmentioning

confidence: 57%

Hydroaminomethylation of the Renewable Limonene with Ammonia in an Aqueous Biphasic Solvent System

Behr

Wintzer

2015

Chem Eng & Technol

Self Cite

View full text Add to dashboard Cite

With the hydroaminomethylation of the natural compound limonene with ammonia an atom-economic method for the synthesis of primary amines is described. This tandem reaction allows the direct conversion of the unfunctionalized monoterpene to a valuable amine product. For the first time, ammonia served as substrate to result in a maximum primary amine yield of 25 %. To overcome unwanted side reactions, a biphasic solvent system was used, consisting of an aqueous catalyst phase and an organic product phase. As catalyst the water-soluble transition metal complex [Rh(cod)Cl] 2 /triphenylphosphine trisulfonate was chosen. In combination with the surfactant hexadecyltrimethylammonium chloride it provided a good phase interaction and the possibility for easy phase separation after the reaction.

show abstract

Section: Resultsmentioning

confidence: 57%

Hydroaminomethylation of the Renewable Limonene with Ammonia in an Aqueous Biphasic Solvent System

Behr

Wintzer

2015

Chem Eng & Technol

Self Cite

View full text Add to dashboard Cite

show abstract

“…Besides the hydroamination and hydroaminomethylation, a couple of homogeneously catalyzed reactions of β ‐myrcene were developed in our group resulting in esters of different chain length with specialized applications, for instance, in flavors and fragrances. Branched C11‐esters were obtained in 61 % yields by palladium catalyzed methoxycarbonylation, as well as by ruthenium catalyzed cross metathesis with methyl acrylate . However, ruthenium catalyzed codimerization with methyl acrylate yields different C13‐esters (Figure ) …”

Section: C6 Molecules (Renewables)mentioning

confidence: 99%

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

et al. 2018

Self Cite

View full text Add to dashboard Cite

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.

show abstract

“…A frequently used starting material is butadiene which is mainly reacted with palladium and cobalt based catalysts. [38][39][40][41][42] Nevertheless, there are also other other dienes like the renewable diene myrcene [43] and also piperylene has already been subjected to hydroesterification. [ connected to an autosampler was used to detect individual components.…”

Section: Introductionmentioning

confidence: 99%

Three step auto-tandem catalysed hydroesterification: Access to linear fruity esters from piperylene

Neubert

Steffen

Behr

2015

Journal of Molecular Catalysis A: Chemical

Self Cite

View full text Add to dashboard Cite

First methoxycarbonylation of the renewable β-myrcene: high selectivity through reduced isomerisation

Cited by 12 publications

References 21 publications

Hydroaminomethylation of the Renewable Limonene with Ammonia in an Aqueous Biphasic Solvent System

Hydroaminomethylation of the Renewable Limonene with Ammonia in an Aqueous Biphasic Solvent System

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

Three step auto-tandem catalysed hydroesterification: Access to linear fruity esters from piperylene

Contact Info

Product

Resources

About