Caprolactam from Renewable Resources: Catalytic Conversion of 5‐Hydroxymethylfurfural into Caprolactone

Buntara, Teddy; Noël, S.; Phua, Pim Huat; Melián‐Cabrera, Ignacio; Vries, Johannes G. de; Heeres, Hero Jan

doi:10.1002/ange.201102156

Cited by 126 publications

(74 citation statements)

References 33 publications

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“…The current industrial process is based on the Ni-catalysed hydrocyanation of 1,3-butadiene. In our novel process, the desired product is obtained by selective oxidation of 1,6-hexanediol which can be derived from biomass 36 as shown in Fig. 3, in the presence of aq.…”

Section: Resultsmentioning

confidence: 99%

Green synthesis of nitriles using non-noble metal oxides-based nanocatalysts

2014

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(Hetero)aromatic and aliphatic nitriles constitute major building blocks for organic synthesis and represent a versatile motif found in numerous medicinally and biologically important compounds. In general, these nitriles are synthesized by traditional cyanation procedures using toxic cyanides. With respect to green chemistry, the development of more sustainable and cost-efficient processes for the synthesis of advanced nitriles is highly desired. Here we report an environmentally benign synthesis of all kinds of structurally diverse aryl, heterocyclic, allylic and aliphatic nitriles from easily available alcohols applying aqueous ammonia and molecular oxygen. Key to success for this synthesis is the use of nitrogen-doped graphene-layered non-noble metal oxides as stable and durable nanocatalysts. As an example a renewable synthesis of adiponitrile, an industrially important bulk chemical is presented.

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Section: Resultsmentioning

confidence: 99%

Green synthesis of nitriles using non-noble metal oxides-based nanocatalysts

2014

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“…However, benzyl benzoate was isolated as the sole product as a result of an intermolecular condensation process; 1,5-pentanediol (Table 1, entry 7) was also dehydrogenated successfully to afford δ-valerolactone. Several research groups have previously reported homogeneous catalysts for the base-free oxidation of diols to lactones in the presence of a hydrogen acceptor, such as acetone (32)(33)(34)(35). However, reports related to the acceptorless conversion of the same are extremely rare in the literature (36)(37)(38)(39).…”

Section: Resultsmentioning

confidence: 99%

Reversible catalytic dehydrogenation of alcohols for energy storage

Bonitatibus

Chakraborty

Doherty

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

123

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Reversibility of a dehydrogenation/hydrogenation catalytic reaction has been an elusive target for homogeneous catalysis. In this report, reversible acceptorless dehydrogenation of secondary alcohols and diols on iron pincer complexes and reversible oxidative dehydrogenation of primary alcohols/reduction of aldehydes with separate transfer of protons and electrons on iridium complexes are shown. This reactivity suggests a strategy for the development of reversible fuel cell electrocatalysts for partial oxidation (dehydrogenation) of hydroxyl-containing fuels.

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“…For example, recently, caprolactam has been prepared in a four-step process from 5-hydroxymethylfurfural (5-HMF) and ammonia. [4] Inspired by such research, we wondered whether amino-sugars could be used as precursors to new Ncontaining platform chemicals. Our initial studies in this area are presented herein.…”

Section: Introductionmentioning

confidence: 99%