Valorization of Madagascar’s CNSL via the synthesis of one advanced intermediate (3-Pentadecylcyclohexanone)

Rahobinirina, Andrianarivo Irène; Rakotondramanga, Maonja Finaritra; Berlioz‐Barbier, Alexandra; Métay, Estelle; Ramanandraibe, Voahangy; Lemaire, Marc

doi:10.1016/j.tetlet.2017.04.093

Cited by 13 publications

(10 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For the direct separation of 2 from 3 in technical scale, a fractionated distillation would clearly be cheaper and more sustainable. Experiments at temperatures above 50°C to accelerate the hydrogenation resulted contradictory to recent investigations (Rahobinirina et al, ) in an increased formation of 3 at the expense of 2 . In our experience, the selective hydrogenation of cardanol to 2 is highly temperature‐dependent.…”

Section: Resultsmentioning

confidence: 59%

“…According to entries 1–4, the ketone 2 was oxidized successfully with performic acid to the lactones 5a and 5b in moderate and good yields. In contrast, the oxidation with peracetic acid was reported to be less effective because of a comparatively poor yield of 39% (Rahobinirina et al, ). For all experiments compiled in Table , a complete conversion of 2 was observed.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of novel chemicals from cardanol as a product of cashew nutshell processing

Deutsch

Köckritz

2020

Food Science & Nutrition

View full text Add to dashboard Cite

The conversion of the worldwide chemical production from fossil to sustainable resources is currently one of the most urgent tasks for the chemical industry. Based on this approach cardanol, a mixture of phenols with C15‐chains as substituents is produced in some countries of the tropical zone from the processing of cashew nutshells. The paper reports the specific transformation of the aromatic moiety in this cheap material, and thus, the development of a novel route to potential useful green bifunctional chemicals in gram scale. Accordingly, cardanol was converted successfully in three steps into hexane‐1,6‐diols. The evaluation of appropriate synthesis methods and suitable conditions for each of these reaction steps is presented as an essential topic of these investigations. The target compounds synthesized in the reaction sequence are potential building blocks for future biomass‐based chemicals and monomers for green polymeric materials, surfactants, and lubricants.

show abstract

Section: Resultsmentioning

confidence: 59%

Section: Resultsmentioning

confidence: 99%

Synthesis of novel chemicals from cardanol as a product of cashew nutshell processing

Deutsch

Köckritz

2020

Food Science & Nutrition

View full text Add to dashboard Cite

show abstract

“…Currently, the most promising products from cardanol are epoxy monomers, acrylate, PVC-plasticizers and emulsion surfactants. But very interesting development gain attention, such as the work of Lemaire et al who succeeded in the synthesis of 3-pentadecylcyclohexanone, which has structural similarity with the cyclohexanone, a very important building block of the petro-based chemical industry [101]. Thus, we could consider that CNSL-based products would find widespread applications especially for the production of polymers with a unique combination of properties.…”

Section: Discussionmentioning

confidence: 99%

Cardanol: A promising building block for biobased polymers and additives

Caillol

2018

Current Opinion in Green and Sustainable Chemistry

View full text Add to dashboard Cite

Among the renewable resource materials, cashew nut shell liquid (CNSL) is considered as an important starting material due to its unique structural features, abundant availability and low cost. A large number of chemicals and products have been developed starting from CNSL by taking advantage of the three reactive sites, namely, phenolic hydroxyl, aromatic ring and unsaturation(s) in the alkenyl side chain. Increasing attention is paid to promising cardanol-based products that could be have potential interest in industry, such as epoxy and acrylic monomers, plasticizers and surfactants.

show abstract

“…Cardanol is constituted of a mixture of at least four constituents differing in the unsaturated side chain, namely saturated (5–8%), monoene (48–49%), diene (l6–17%), and triene (29–30%) as illustrated in Figure . Its phenolic group can be functionalized by etherification, esterification . whereas various additions and epoxidations can be performed on the double bond of the alkyl side chain .…”

Section: Introductionmentioning

confidence: 99%

“…Its phenolic group can be functionalized by etherification, esterification. [15][16][17][18] whereas various additions and epoxidations can be performed on the double bond of the alkyl side chain. [19,20] It was demonstrated that the addition of cardanol in phenol-formaldehyde formulations affects the mechanical properties.…”

Section: Introductionmentioning

confidence: 99%

Cardanol‐Based and Formaldehyde‐Free Flexible Phenolic Networks

Briou

Caillol

Robin

et al. 2018

Euro J Lipid Sci & Tech

View full text Add to dashboard Cite

Commercial novolac‐type phenolic thermosets are mainly synthesized from highly toxic precursors such as phenol and formaldehyde. Herein, the phenolic chemistry is renewed with bio‐based and non‐toxic precursors such as cardanol and nonanal to elaborate flexible phenolic thermosets. The two‐step novolac strategy involves the synthesis of a cardanol nonanal pre‐polymer (PCN) prior to its cross‐linking in presence of a supplementary amount of nonanal hardener. The curing process is optimized by rheology measurement and thermogravimetry analysis. The alkyl chains of this phenolic network induces soft mechanical properties acting as internal plasticizers. The softening of the resulting networks do not induce a loss of thermal stability. Showing a good compromise between softness and high thermal resistance, cardanol‐nonanal networks (RCN) seem to be relevant examples of an innovative and biobased approach for phenolic chemistry to design bio‐sourced materials without any petro‐based or hazardous molecules. Practical Applications: Various practical applications where smooth and soft coatings are employed can be considered. Novolac chemistry for bio‐based and notoxic resources: cardanol and nonanal. Softness and high thermal resistance phenolic resins are elaborated. These materials are based on internal plasticized cross‐linked materials.

show abstract

Valorization of Madagascar’s CNSL via the synthesis of one advanced intermediate (3-Pentadecylcyclohexanone)

Cited by 13 publications

References 36 publications

Synthesis of novel chemicals from cardanol as a product of cashew nutshell processing

Synthesis of novel chemicals from cardanol as a product of cashew nutshell processing

Cardanol: A promising building block for biobased polymers and additives

Cardanol‐Based and Formaldehyde‐Free Flexible Phenolic Networks

Contact Info

Product

Resources

About