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Special Issue "Catalysis Applied to Biomass—Toward Sustainable Processes and Chemicals"

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Green Chemistry".

Deadline for manuscript submissions: closed (30 July 2016)

Special Issue Editor

Guest Editor
Prof. Dr. Christophe Len

Sorbonne Universités, Université de Technologie de Compiègne (UTC), Centre de Recherche Royallieu, CS 60319, F-60203 Compiègne Cedex, France
Website | E-Mail
Phone: +33 (0)3 44 23 88 28 / +33 (0)6 38 50 09 76
Fax: +33 (0)3 44 97 15 91
Interests: green chemistry; biomass, catalysis

Special Issue Information

Dear Colleagues,

We are pleased to announce the new Special Issue of the Catalysis Applied to Biomass – Toward sustainable processes and chemicals”– CABiomass 2016 (to be held in Compiègne, France). This event will provide a highly interactive platform for relevant experts from the French and international biomass and catalysis sectors to identify chemical and technological project ideas. This meeting also provides an excellent opportunity for experts to establish competitive consortia that can lead to collaborative projects, potential applications, and innovation in the biorefinery sector.

The conference will focus on the following key areas:

- novel catalytic reactions (homogeneous, heterogeneous and enzymatic as well as their combinations) applied to bio-based compounds or using bio-based reagents, either in a sequential way or in a one-pot combined synthesis

- novel catalytic reactions (homogeneous, heterogeneous and enzymatic as well as their combinations) using green solvents (e.g., water, ionic liquids, deep eutectic, critical fluids, etc.)

- new ambitious technologies using flow chemistry, enzymes, microwaves, microreactors, nanocatalysts and more remarkably novel combinations between these technologies

A Special Issue will be produced relating with CABiomass–2016. It is our pleasure to invite you to contribute an original research paper or a review article for this Special Issue. Papers can detail the work you present at CABiomass–2016. The due date for submissions will be June 30, 2016.

Thank you for your contribution.

Prof. Dr. Christophe Len
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • green chemistry
  • biomass
  • catalysis
  • process development

Published Papers (8 papers)

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Research

Open AccessArticle Biocatalytic Synthesis of Novel Partial Esters of a Bioactive Dihydroxy 4-Methylcoumarin by Rhizopus oryzae Lipase (ROL)
Molecules 2016, 21(11), 1499; doi:10.3390/molecules21111499
Received: 31 July 2016 / Revised: 24 October 2016 / Accepted: 2 November 2016 / Published: 9 November 2016
Cited by 1 | PDF Full-text (1413 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Highly regioselective acylation has been observed in 7,8-dihydroxy-4-methylcoumarin (DHMC) by the lipase from Rhizopus oryzae suspended in tetrahydrofuran (THF) at 45 °C using six different acid anhydrides as acylating agents. The acylation occurred regioselectively at one of the two hydroxy groups of the
[...] Read more.
Highly regioselective acylation has been observed in 7,8-dihydroxy-4-methylcoumarin (DHMC) by the lipase from Rhizopus oryzae suspended in tetrahydrofuran (THF) at 45 °C using six different acid anhydrides as acylating agents. The acylation occurred regioselectively at one of the two hydroxy groups of the coumarin moiety resulting in the formation of 8-acyloxy-7-hydroxy-4-methylcoumarins, which are important bioactive molecules for studying biotansformations in animals, and are otherwise very difficult to obtain by only chemical steps. Six monoacylated, monohydroxy 4-methylcoumarins have been biocatalytically synthesised and identified on the basis of their spectral data and X-ray crystal analysis. Full article
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Open AccessArticle Catalytic Synthesis of a New Series of Alkyl Uronates and Evaluation of Their Physicochemical Properties
Molecules 2016, 21(10), 1301; doi:10.3390/molecules21101301
Received: 27 July 2016 / Revised: 13 September 2016 / Accepted: 22 September 2016 / Published: 28 September 2016
PDF Full-text (2795 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Large quantities (>3 g) of a new series of alkyl uronates were synthesized in two steps from commercial methyl hexopyranosides. Firstly, several tens of grams of free methyl α-d-glucopyranoside were selectively and quantitatively oxidized into corresponding sodium uronate using 2,2,6,6-tetramethyl-1-piperidinyloxy free
[...] Read more.
Large quantities (>3 g) of a new series of alkyl uronates were synthesized in two steps from commercial methyl hexopyranosides. Firstly, several tens of grams of free methyl α-d-glucopyranoside were selectively and quantitatively oxidized into corresponding sodium uronate using 2,2,6,6-tetramethyl-1-piperidinyloxy free radical (TEMPO)-catalyzed oxidation. Hydrophobic chains of different length were then introduced by acid-mediated esterification with fatty alcohols (ethyl to lauryl alcohol) leading to the desired alkyl glucuronates with moderate to good yields (49%–72%). The methodology was successfully applied to methyl α-d-mannopyranoside and methyl β-d-galactopyranoside. Physicochemical properties, such as critical micelle concentration (CMC), equilibrium surface tension at CMC (γcmc), solubility, and Krafft temperature were measured, and the effect of structural modifications on surface active properties and micelle formation was discussed. Full article
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Open AccessArticle Synthesis of High-Molecular-Weight Multifunctional Glycerol Polyhydroxyurethanes PHUs
Molecules 2016, 21(9), 1220; doi:10.3390/molecules21091220
Received: 25 July 2016 / Revised: 8 September 2016 / Accepted: 8 September 2016 / Published: 11 September 2016
Cited by 2 | PDF Full-text (2974 KB) | HTML Full-text | XML Full-text
Abstract
Glycerol carbonate acrylate is a 5-membered cyclic carbonate synthesized from glycerol that is used as a chemical coupling agent and has proven highly suitable for use in the synthesis of multifunctional polyhydroxyurethanes (PHUs). The multifunctionality of the structure of PHUs is determined by
[...] Read more.
Glycerol carbonate acrylate is a 5-membered cyclic carbonate synthesized from glycerol that is used as a chemical coupling agent and has proven highly suitable for use in the synthesis of multifunctional polyhydroxyurethanes (PHUs). The multifunctionality of the structure of PHUs is determined by the density of the carbon-amine groups generated by the Aza-Michael reaction and that of the urethane groups and adjacent primary and secondary hydroxyl groups generated by aminolysis. Glycerol carbonate acrylate is polymerized with polyfunctional mono-, di-, tri, and tetra-amines, by type-AB polyaddition, either in bulk or in solution, through stepwise or one-pot reaction strategies in the absence of added catalysts. These approaches result in the generation of linear, interchain, and crosslinked structures, through the polyaddition of linear and branched amines to the ethylene and cyclic carbonate sites of glycerol carbonate acrylate. The resulting collection of organic molecules gives rise to polyethylene amino ester PHUs with a high molar mass, exceeding 20,000 g·mol−1, with uniform dispersity. Full article
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Open AccessArticle Keratin Protein-Catalyzed Nitroaldol (Henry) Reaction and Comparison with Other Biopolymers
Molecules 2016, 21(9), 1122; doi:10.3390/molecules21091122
Received: 15 July 2016 / Revised: 2 August 2016 / Accepted: 2 August 2016 / Published: 25 August 2016
Cited by 2 | PDF Full-text (1434 KB) | HTML Full-text | XML Full-text
Abstract
Here we describe a preliminary investigation on the ability of natural keratin to catalyze the nitroaldol (Henry) reaction between aldehydes and nitroalkanes. Both aromatic and heteroaromatic aldehydes bearing strong or moderate electron-withdrawing groups were converted into the corresponding β-nitroalcohol products in both DMSO
[...] Read more.
Here we describe a preliminary investigation on the ability of natural keratin to catalyze the nitroaldol (Henry) reaction between aldehydes and nitroalkanes. Both aromatic and heteroaromatic aldehydes bearing strong or moderate electron-withdrawing groups were converted into the corresponding β-nitroalcohol products in both DMSO and in water in the presence of tetrabutylammonium bromide (TBAB) as a phase transfer catalyst. Negligible background reactions (i.e., negative control experiment in the absence of keratin protein) were observed in these solvent systems. Aromatic aldehydes bearing electron-donating groups and aliphatic aldehydes showed poor or no conversion, respectively. In general, the reactions in water/TBAB required twice the amount of time than in DMSO to achieve similar conversions. Moreover, comparison of the kinetics of the keratin-mediated nitroaldol (Henry) reaction with other biopolymers revealed slower rates for the former and the possibility of fine-tuning the kinetics by appropriate selection of the biopolymer and solvent. Full article
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Open AccessArticle Furfural Production from d-Xylose and Xylan by Using Stable Nafion NR50 and NaCl in a Microwave-Assisted Biphasic Reaction
Molecules 2016, 21(8), 1102; doi:10.3390/molecules21081102
Received: 9 July 2016 / Revised: 5 August 2016 / Accepted: 10 August 2016 / Published: 22 August 2016
Cited by 8 | PDF Full-text (3406 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Pentose dehydration and direct transformation of xylan into furfural were performed in a water-cyclopentyl methyl ether (CPME) biphasic system under microwave irradiation. Heated up between 170 and 190 °C in the presence of Nafion NR50 and NaCl, d-xylose, l-arabinose and xylan
[...] Read more.
Pentose dehydration and direct transformation of xylan into furfural were performed in a water-cyclopentyl methyl ether (CPME) biphasic system under microwave irradiation. Heated up between 170 and 190 °C in the presence of Nafion NR50 and NaCl, d-xylose, l-arabinose and xylan gave furfural with maximum yields of 80%, 42% and 55%, respectively. The influence of temperature and reaction time on the reaction kinetics was discussed. This study was also completed by the survey of different reactant ratios, such as organic layer-water or catalyst-inorganic salt ratios. The exchange between proton and cation induced by an excess of NaCl was monitored, and a synergetic effect between the remaining protons and the released HCl was also discovered. Full article
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Open AccessArticle Efficient Enzyme-Free Biomimetic Sensors for Natural Phenol Detection
Molecules 2016, 21(8), 1060; doi:10.3390/molecules21081060
Received: 9 July 2016 / Revised: 4 August 2016 / Accepted: 9 August 2016 / Published: 13 August 2016
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Abstract
The development of sensors and biosensors based on copper enzymes and/or copper oxides for phenol sensing is disclosed in this work. The electrochemical properties were studied by cyclic and differential pulse voltammetry using standard solutions of potassium ferrocyanide, phosphate/acetate buffers and representative natural
[...] Read more.
The development of sensors and biosensors based on copper enzymes and/or copper oxides for phenol sensing is disclosed in this work. The electrochemical properties were studied by cyclic and differential pulse voltammetry using standard solutions of potassium ferrocyanide, phosphate/acetate buffers and representative natural phenols in a wide pH range (3.0 to 9.0). Among the natural phenols herein investigated, the highest sensitivity was observed for rutin, a powerful antioxidant widespread in functional foods and ubiquitous in the plant kingdom. The calibration curve for rutin performed at optimum pH (7.0) was linear in a broad concentration range, 1 to 120 µM (r = 0.99), showing detection limits of 0.4 µM. The optimized biomimetic sensor was also applied in total phenol determination in natural samples, exhibiting higher stability and sensitivity as well as distinct selectivity for antioxidant compounds. Full article
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Open AccessArticle Chemo-Enzymatic Synthesis of Oligoglycerol Derivatives
Molecules 2016, 21(8), 1038; doi:10.3390/molecules21081038
Received: 20 July 2016 / Revised: 4 August 2016 / Accepted: 5 August 2016 / Published: 9 August 2016
PDF Full-text (1448 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A cleaner and greener method has been developed and used to synthesize 14 different functionalized oligomer derivatives of glycerol in moderate 29%–39% yields over three steps. After successive regioselective enzymatic acylation of the primary hydroxyl groups, etherification or esterification of the secondary hydroxyl
[...] Read more.
A cleaner and greener method has been developed and used to synthesize 14 different functionalized oligomer derivatives of glycerol in moderate 29%–39% yields over three steps. After successive regioselective enzymatic acylation of the primary hydroxyl groups, etherification or esterification of the secondary hydroxyl groups and chemoselective enzymatic saponification, the target compounds can efficiently be used as versatile building blocks in organic and supramolecular chemistry. Full article
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Open AccessArticle Chemo-Enzymatic Synthesis of Chiral Epoxides Ethyl and Methyl (S)-3-(Oxiran-2-yl)propanoates from Renewable Levoglucosenone: An Access to Enantiopure (S)-Dairy Lactone
Molecules 2016, 21(8), 988; doi:10.3390/molecules21080988
Received: 28 June 2016 / Revised: 21 July 2016 / Accepted: 23 July 2016 / Published: 29 July 2016
PDF Full-text (1687 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Chiral epoxides—such as ethyl and methyl (S)-3-(oxiran-2-yl)propanoates ((S)-1a/1b)—are valuable precursors in many chemical syntheses. Until recently, these compounds were synthesized from glutamic acid in four steps (deamination, reduction, tosylation and epoxide formation) in low to
[...] Read more.
Chiral epoxides—such as ethyl and methyl (S)-3-(oxiran-2-yl)propanoates ((S)-1a/1b)—are valuable precursors in many chemical syntheses. Until recently, these compounds were synthesized from glutamic acid in four steps (deamination, reduction, tosylation and epoxide formation) in low to moderate overall yield (20%–50%). Moreover, this procedure requires some harmful reagents such as sodium nitrite ((eco)toxic) and borane (carcinogen). Herein, starting from levoglucosenone (LGO), a biobased chiral compound obtained through the flash pyrolysis of acidified cellulose, we propose a safer and more sustainable chemo-enzymatic synthetic pathway involving lipase-mediated Baeyer-Villiger oxidation, palladium-catalyzed hydrogenation, tosylation and treatment with sodium ethoxide/methoxide as key steps. This route afforded ethyl and methyl (S)-3-(oxiran-2-yl)propanoates in 57% overall yield, respectively. To demonstrate the potentiality of this new synthetic pathway from LGO, the synthesis of high value-added (S)-dairy lactone was undertaken from these epoxides and provided the target in 37% overall yield from LGO. Full article
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