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Frontier in Green Chemistry Approaches
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Frontier in Green Chemistry Approaches

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

Deadline for manuscript submissions: closed (30 May 2015) | Viewed by 129981

Special Issue Editor

Dr. Kei Saito

E-Mail Website
Guest Editor
School of Chemistry, Monash University, Clayton, VIC 3800, Australia
Interests: green chemistry; green organic synthesis; polymer chemistry; biomass; photo-responsive polymers
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

This Special Issue will highlight recent advances in green chemistry in general. To date, a wide variety of green chemistry approaches have been developed and used for organic reactions. We encourage submissions that explore novel green chemistry approaches that can impact society. Papers that focus on development of new green chemistry metrics are also encouraged.

We invite submissions of original research and review articles for this Special Issue of Molecules.

Dr. Kei Saito
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 submissions that pass pre-check are 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 semimonthly 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 2700 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 research
  • atom economical reactions
  • organic reactions in green solvents
  • multicomponent reactions
  • solid state reactions
  • reactions using renewable resources
  • photo-chemical reactions
  • sono chemistry
  • microwave assisted synthesis
  • biomass conversions
  • green catalysts including heterogeneous catalysts
  • green polymers
  • green chemistry metrics

Published Papers (14 papers)

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Editorial

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163 KiB  
Editorial
Renewable Green Platform Chemicals for Polymers
by Parijat Ray, Craig Smith, George P. Simon and Kei Saito
Molecules 2017, 22(3), 376; https://doi.org/10.3390/molecules22030376 - 28 Feb 2017
Cited by 16 | Viewed by 4117
Abstract
This Special Issue covered topics in the field of Green Chemistry.[...] Full article
(This article belongs to the Special Issue Frontier in Green Chemistry Approaches)

Research

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915 KiB  
Article
Poly(N-4-vinylbenzyl-1,4,7-triazacyclononane) Copper Complex Grafted Solid Catalyst for Oxidative Polymerization of 2,6-Dimethylphenol
by Kei Saito, Koji Miyamoto, Sepa Nanayakkara, Hirotaka Ihara and Milton T. W. Hearn
Molecules 2016, 21(2), 146; https://doi.org/10.3390/molecules21020146 - 26 Jan 2016
Cited by 2 | Viewed by 4897
Abstract
A new solid phase catalyst, poly(N-4-vinylbenzyl-1,4,7-triazacyclononane) copper(I) complex, grafted onto polystyrene particles, has been employed for the oxidative polymerization of 2,6-dimethylphenol using an aqueous biphasic (water/toluene) solvent system. The solid catalyst was synthesized by first grafting N-(4-vinylbenzyl)-1,4,7-triaza-cyclononane onto polystyrene particles [...] Read more.
A new solid phase catalyst, poly(N-4-vinylbenzyl-1,4,7-triazacyclononane) copper(I) complex, grafted onto polystyrene particles, has been employed for the oxidative polymerization of 2,6-dimethylphenol using an aqueous biphasic (water/toluene) solvent system. The solid catalyst was synthesized by first grafting N-(4-vinylbenzyl)-1,4,7-triaza-cyclononane onto polystyrene particles using a radical mediated polymerization method and next by creating the polymer-metal complex of copper-triazacyclononane with these modified particles. Poly(2,6-dimethyl-1,4-phenylene oxide) was successfully obtained from the polymerization of 2,6-dimethylphenol using this new metal-organic solid phase catalyst. Full article
(This article belongs to the Special Issue Frontier in Green Chemistry Approaches)
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1837 KiB  
Article
Green Synthesis of Novel Polyaniline Nanofibers: Application in pH Sensing
by Shivani Tanwar and Ja-an Annie Ho
Molecules 2015, 20(10), 18585-18596; https://doi.org/10.3390/molecules201018585 - 13 Oct 2015
Cited by 27 | Viewed by 7873
Abstract
An optically active polyaniline nanomaterial (PANI-Nap), doped with (S)-naproxen, was developed and evaluated as a potent pH sensor. We synthesized the material in one pot by the addition of the dopant, (S)-naproxen, prior to polymerization, followed by the addition [...] Read more.
An optically active polyaniline nanomaterial (PANI-Nap), doped with (S)-naproxen, was developed and evaluated as a potent pH sensor. We synthesized the material in one pot by the addition of the dopant, (S)-naproxen, prior to polymerization, followed by the addition of the oxidizing agent (ammonium persulfate) that causes polymerization of the aniline. This green chemistry approach allowed us to take only 1 h to produce a water-soluble and stable nanomaterial. UV-visible spectroscopy, fluorescence spectroscopy, FT-IR spectroscopy, Raman spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), and X-ray photoelectron spectroscopy (XPS) were used to characterize the designed nanomaterial. This nanomaterial exhibited excellent pH sensing properties and showed long term stability (up to one month) without loss of sensor performance. Full article
(This article belongs to the Special Issue Frontier in Green Chemistry Approaches)
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733 KiB  
Article
The Application of Template Selectophores for the Preparation of Molecularly Imprinted Polymers
by Basil Danylec, Lachlan J. Schwarz, Simon J. Harris, Reinhard I. Boysen and Milton T. W. Hearn
Molecules 2015, 20(9), 17601-17613; https://doi.org/10.3390/molecules200917601 - 23 Sep 2015
Cited by 13 | Viewed by 6859
Abstract
Molecularly imprinted polymers are versatile materials with wide application scope for the detection, capture and separation of specific compounds present in complex feed stocks. A major challenge associated with their preparation has been the need to sacrifice one mole equivalent of the template [...] Read more.
Molecularly imprinted polymers are versatile materials with wide application scope for the detection, capture and separation of specific compounds present in complex feed stocks. A major challenge associated with their preparation has been the need to sacrifice one mole equivalent of the template molecule to generate the complementary polymer cavities that selectively bind the target molecule. Moreover, template molecules can often be difficult to synthesise, expensive or lack stability. In this study, we describe a new approach, directed at the use of synthetic selectophores, chosen as readily prepared and low cost structural analogues with recognition groups in similar three-dimensional arrangements as found in the target molecule. To validate the approach, a comparative study of selectophores related to the polyphenolic compound (E)-resveratrol has been undertaken using traditional and green chemical synthetic approaches. These molecular mimic compounds were employed as polymer templates and also as binding analytes to interrogate the recognition sites associated with the molecularly imprinted polymers. Importantly, the study confirms that the use of selectophores has the potential to confer practical advantages, including access to more efficient methods for selection and preparation of suitable template molecules with a broader range of molecular diversity, as well as delivering imprinted polymers capable of recognizing the target compound and structurally related products. Full article
(This article belongs to the Special Issue Frontier in Green Chemistry Approaches)
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798 KiB  
Article
Addition of CFCl3 to Aromatic Aldehydes via in Situ Grignard Reaction
by Balaka Barkakaty, Bandana Talukdar and Bradley S. Lokitz
Molecules 2015, 20(8), 15098-15107; https://doi.org/10.3390/molecules200815098 - 18 Aug 2015
Cited by 1 | Viewed by 7548
Abstract
Synthetic modification of trichlorofluoromethane (CFCl3) to non-volatile and useful fluorinated precursors is a cost-effective and an environmentally benign strategy for the safe consumption/destruction of the ozone depleting potential of the reagent. In this report, we present a novel method for in [...] Read more.
Synthetic modification of trichlorofluoromethane (CFCl3) to non-volatile and useful fluorinated precursors is a cost-effective and an environmentally benign strategy for the safe consumption/destruction of the ozone depleting potential of the reagent. In this report, we present a novel method for in situ Grignard reaction using magnesium powder and CFCl3 for synthesis of dichlorofluoromethyl aromatic alcohols. Full article
(This article belongs to the Special Issue Frontier in Green Chemistry Approaches)
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1074 KiB  
Article
Iminoiodane- and Brønsted Base-Mediated Cross Dehydrogenative Coupling of Cyclic Ethers with 1,3-Dicarbonyl Compounds
by Ciputra Tejo, Xiao Rong Sim, Bo Ra Lee, Benjamin James Ayers, Chung-Hang Leung, Dik-Lung Ma and Philip Wai Hong Chan
Molecules 2015, 20(7), 13336-13353; https://doi.org/10.3390/molecules200713336 - 22 Jul 2015
Cited by 8 | Viewed by 9014
Abstract
A one-pot, two-step approach to prepare 2-tetrahydrofuran and -pyran substituted 1,3-dicarbonyl compounds by PhI=NTs-mediated amination/Brønsted base-catalyzed cross dehydrogenative coupling (CDC) reaction of the cyclic ether and 1,3-dicarbonyl derivative under mild conditions is reported. The reaction is compatible with a variety of cyclic ethers [...] Read more.
A one-pot, two-step approach to prepare 2-tetrahydrofuran and -pyran substituted 1,3-dicarbonyl compounds by PhI=NTs-mediated amination/Brønsted base-catalyzed cross dehydrogenative coupling (CDC) reaction of the cyclic ether and 1,3-dicarbonyl derivative under mild conditions is reported. The reaction is compatible with a variety of cyclic ethers and 1,3-dicarbonyl compounds, affording the corresponding coupled products in moderate to good yields of up to 80% over two steps. Full article
(This article belongs to the Special Issue Frontier in Green Chemistry Approaches)
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Graphical abstract

1492 KiB  
Article
Cu and Boron Doped Carbon Nitride for Highly Selective Oxidation of Toluene to Benzaldehyde
by Hongling Han, Guodong Ding, Tianbin Wu, Dexin Yang, Tao Jiang and Buxing Han
Molecules 2015, 20(7), 12686-12697; https://doi.org/10.3390/molecules200712686 - 13 Jul 2015
Cited by 36 | Viewed by 7865
Abstract
A novel Cu and boron doped graphitic carbon nitride catalyst (Cu-CNB) was synthesized using cheap precursors and systematically characterized. The selective oxidation of toluene proceeded very smoothly over the catalyst at 70 °C using tert-butyl hydroperoxide (TBHP) as the oxidant to exclusively afford [...] Read more.
A novel Cu and boron doped graphitic carbon nitride catalyst (Cu-CNB) was synthesized using cheap precursors and systematically characterized. The selective oxidation of toluene proceeded very smoothly over the catalyst at 70 °C using tert-butyl hydroperoxide (TBHP) as the oxidant to exclusively afford benzaldehyde. The catalyst can be used for at least five cycles without decrease in activity and selectivity. Full article
(This article belongs to the Special Issue Frontier in Green Chemistry Approaches)
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790 KiB  
Article
Synthesis of (E)-2-Styrylchromones and Flavones by Base-Catalyzed Cyclodehydration of the Appropriate β-Diketones Using Water as Solvent
by Joana Pinto, Vera L. M. Silva, Ana M. G. Silva and Artur M. S. Silva
Molecules 2015, 20(6), 11418-11431; https://doi.org/10.3390/molecules200611418 - 22 Jun 2015
Cited by 18 | Viewed by 7578
Abstract
A low cost, safe, clean and environmentally benign base-catalyzed cyclodehydration of appropriate β-diketones affording (E)-2-styrylchromones and flavones in good yields is disclosed. Water was used as solvent and the reactions were heated using classical and microwave heating methods, under open and [...] Read more.
A low cost, safe, clean and environmentally benign base-catalyzed cyclodehydration of appropriate β-diketones affording (E)-2-styrylchromones and flavones in good yields is disclosed. Water was used as solvent and the reactions were heated using classical and microwave heating methods, under open and closed vessel conditions. β-Diketones having electron-donating and withdrawing substituents were used to evaluate the reaction scope. The reaction products were isolated in high purity by simple filtration and recrystallization from ethanol, when using 800 mg of the starting diketone under classical reflux heating conditions. Full article
(This article belongs to the Special Issue Frontier in Green Chemistry Approaches)
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412 KiB  
Article
An Efficient Synthesis of 3,4-Dihydropyrimidin-2(1H)-Ones and Thiones Catalyzed by a Novel Brønsted Acidic Ionic Liquid under Solvent-Free Conditions
by Yonghong Zhang, Bin Wang, Xiaomei Zhang, Jianbin Huang and Chenjiang Liu
Molecules 2015, 20(3), 3811-3820; https://doi.org/10.3390/molecules20033811 - 26 Feb 2015
Cited by 73 | Viewed by 8525
Abstract
We report here an efficient and green method for Biginelli condensation reaction of aldehydes, β-ketoesters and urea or thiourea catalyzed by Brønsted acidic ionic liquid [Btto][p-TSA] under solvent-free conditions. Compared to the classical Biginelli reaction conditions, the present method has the [...] Read more.
We report here an efficient and green method for Biginelli condensation reaction of aldehydes, β-ketoesters and urea or thiourea catalyzed by Brønsted acidic ionic liquid [Btto][p-TSA] under solvent-free conditions. Compared to the classical Biginelli reaction conditions, the present method has the advantages of giving good yields, short reaction times, near room temperature conditions and the avoidance of the use of organic solvents and metal catalyst. Full article
(This article belongs to the Special Issue Frontier in Green Chemistry Approaches)
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1466 KiB  
Article
Selective C–C Coupling Reaction of Dimethylphenol to Tetramethyldiphenoquinone Using Molecular Oxygen Catalyzed by Cu Complexes Immobilized in Nanospaces of Structurally-Ordered Materials
by Zen Maeno, Takato Mitsudome, Tomoo Mizugaki, Koichiro Jitsukawa and Kiyotomi Kaneda
Molecules 2015, 20(2), 3089-3106; https://doi.org/10.3390/molecules20023089 - 12 Feb 2015
Cited by 8 | Viewed by 9690
Abstract
Two high-performance Cu catalysts were successfully developed by immobilization of Cu ions in the nanospaces of poly(propylene imine) (PPI) dendrimer and magadiite for the selective C–C coupling of 2,6-dimethylphenol (DMP) to 3,3',5,5'-tetramethyldiphenoquinone (DPQ) with O2 as a green oxidant. The PPI dendrimer [...] Read more.
Two high-performance Cu catalysts were successfully developed by immobilization of Cu ions in the nanospaces of poly(propylene imine) (PPI) dendrimer and magadiite for the selective C–C coupling of 2,6-dimethylphenol (DMP) to 3,3',5,5'-tetramethyldiphenoquinone (DPQ) with O2 as a green oxidant. The PPI dendrimer encapsulated Cu ions in the internal nanovoids to form adjacent Cu species, which exhibited significantly high catalytic activity for the regioselective coupling reaction of DMP compared to previously reported enzyme and metal complex catalysts. The magadiite-immobilized Cu complex acted as a selective heterogeneous catalyst for the oxidative C–C coupling of DMP to DPQ. This heterogeneous catalyst was recoverable from the reaction mixture by simple filtration, reusable without loss of efficiency, and applicable to a continuous flow reactor system. Detailed characterization using ultraviolet-visible (UV-vis), Fourier transform infrared (FTIR), electronic spin resonance (ESR), and X-ray absorption fine structure (XAFS) spectroscopies and the reaction mechanism investigation revealed that the high catalytic performances of these Cu catalysts were ascribed to the adjacent Cu species generated within the nanospaces of the PPI dendrimer and magadiite. Full article
(This article belongs to the Special Issue Frontier in Green Chemistry Approaches)
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Review

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1825 KiB  
Review
Recent Developments in Chemical Synthesis with Biocatalysts in Ionic Liquids
by Mahesh K. Potdar, Geoffrey F. Kelso, Lachlan Schwarz, Chunfang Zhang and Milton T. W. Hearn
Molecules 2015, 20(9), 16788-16816; https://doi.org/10.3390/molecules200916788 - 15 Sep 2015
Cited by 78 | Viewed by 12666
Abstract
Over the past decade, a variety of ionic liquids have emerged as greener solvents for use in the chemical manufacturing industries. Their unique properties have attracted the interest of chemists worldwide to employ them as replacement for conventional solvents in a diverse range [...] Read more.
Over the past decade, a variety of ionic liquids have emerged as greener solvents for use in the chemical manufacturing industries. Their unique properties have attracted the interest of chemists worldwide to employ them as replacement for conventional solvents in a diverse range of chemical transformations including biotransformations. Biocatalysts are often regarded as green catalysts compared to conventional chemical catalysts in organic synthesis owing to their properties of low toxicity, biodegradability, excellent selectivity and good catalytic performance under mild reaction conditions. Similarly, a selected number of specific ionic liquids can be considered as greener solvents superior to organic solvents owing to their negligible vapor pressure, low flammability, low toxicity and ability to dissolve a wide range of organic and biological substances, including proteins. A combination of biocatalysts and ionic liquids thus appears to be a logical and promising opportunity for industrial use as an alternative to conventional organic chemistry processes employing organic solvents. This article provides an overview of recent developments in this field with special emphasis on the application of more sustainable enzyme-catalyzed reactions and separation processes employing ionic liquids, driven by advances in fundamental knowledge, process optimization and industrial deployment. Full article
(This article belongs to the Special Issue Frontier in Green Chemistry Approaches)
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695 KiB  
Review
Non-Covalent Derivatives: Cocrystals and Eutectics
by Emily Stoler and John C. Warner
Molecules 2015, 20(8), 14833-14848; https://doi.org/10.3390/molecules200814833 - 14 Aug 2015
Cited by 77 | Viewed by 10866
Abstract
Non-covalent derivatives (NCDs) are formed by incorporating one (or more) coformer molecule(s) into the matrix of a parent molecule via non-covalent forces. These forces can include ionic forces, Van der Waals forces, hydrogen bonding, lipophilic-lipophilic interactions and pi-pi interactions. NCDs, in both cocrystal [...] Read more.
Non-covalent derivatives (NCDs) are formed by incorporating one (or more) coformer molecule(s) into the matrix of a parent molecule via non-covalent forces. These forces can include ionic forces, Van der Waals forces, hydrogen bonding, lipophilic-lipophilic interactions and pi-pi interactions. NCDs, in both cocrystal and eutectic forms, possess properties that are unique to their supramolecular matrix. These properties include critical product performance factors such as solubility, stability and bioavailability. NCDs have been used to tailor materials for a variety of applications and have the potential to be used in an even broader range of materials and processes. NCDs can be prepared using little or no solvent and none of the reagents typical to synthetic modifications. Thus, NCDs represent a powerfully versatile, environmentally-friendly and cost-effective opportunity. Full article
(This article belongs to the Special Issue Frontier in Green Chemistry Approaches)
4063 KiB  
Review
Graphene-Based Nanomaterials as Efficient Peroxidase Mimetic Catalysts for Biosensing Applications: An Overview
by Bhaskar Garg, Tanuja Bisht and Yong-Chien Ling
Molecules 2015, 20(8), 14155-14190; https://doi.org/10.3390/molecules200814155 - 04 Aug 2015
Cited by 126 | Viewed by 14116
Abstract
“Artificial enzymes”, a term coined by Breslow for enzyme mimics is an exciting and promising branch of biomimetic chemistry aiming to imitate the general and essential principles of natural enzymes using a variety of alternative materials including heterogeneous catalysts. Peroxidase enzymes represent a [...] Read more.
“Artificial enzymes”, a term coined by Breslow for enzyme mimics is an exciting and promising branch of biomimetic chemistry aiming to imitate the general and essential principles of natural enzymes using a variety of alternative materials including heterogeneous catalysts. Peroxidase enzymes represent a large family of oxidoreductases that typically catalyze biological reactions with high substrate affinity and specificity under relatively mild conditions and thus offer a wide range of practical applications in many areas of science. The increasing understanding of general principles as well as intrinsic drawbacks such as low operational stability, high cost, difficulty in purification and storage, and sensitivity of catalytic activity towards atmospheric conditions of peroxidases has triggered a dynamic field in nanotechnology, biochemical, and material science that aims at joining the better of three worlds by combining the concept adapted from nature with the processability of catalytically active graphene-based nanomaterials (G-NMs) as excellent peroxidase mimetic catalysts. This comprehensive review discusses an up-to-date synthesis, kinetics, mechanisms, and biosensing applications of a variety of G-NMs that have been explored as promising catalysts to mimic natural peroxidases. Full article
(This article belongs to the Special Issue Frontier in Green Chemistry Approaches)
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1263 KiB  
Review
Green Chemistry Metrics with Special Reference to Green Analytical Chemistry
by Marek Tobiszewski, Mariusz Marć, Agnieszka Gałuszka and Jacek Namieśnik
Molecules 2015, 20(6), 10928-10946; https://doi.org/10.3390/molecules200610928 - 12 Jun 2015
Cited by 334 | Viewed by 17548
Abstract
The concept of green chemistry is widely recognized in chemical laboratories. To properly measure an environmental impact of chemical processes, dedicated assessment tools are required. This paper summarizes the current state of knowledge in the field of development of green chemistry and green [...] Read more.
The concept of green chemistry is widely recognized in chemical laboratories. To properly measure an environmental impact of chemical processes, dedicated assessment tools are required. This paper summarizes the current state of knowledge in the field of development of green chemistry and green analytical chemistry metrics. The diverse methods used for evaluation of the greenness of organic synthesis, such as eco-footprint, E-Factor, EATOS, and Eco-Scale are described. Both the well-established and recently developed green analytical chemistry metrics, including NEMI labeling and analytical Eco-scale, are presented. Additionally, this paper focuses on the possibility of the use of multivariate statistics in evaluation of environmental impact of analytical procedures. All the above metrics are compared and discussed in terms of their advantages and disadvantages. The current needs and future perspectives in green chemistry metrics are also discussed. Full article
(This article belongs to the Special Issue Frontier in Green Chemistry Approaches)
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