Latest News

Efficient Eucalyptus chemistry
02 November 2009
Eucalyptus leaves can be used as a greener way to produce a valuable chemical used in fragrances and pharmaceuticals

Ionic liquids share ions for the common good
28 October 2009
Scientists in Italy have made ionic liquids more useful for electrochemistry.

The 3rd International Congress on Ionic Liquids
15 October 2009
Read the report by members of QUILL, The Queen's University of Belfast, on this conference held recently in Cairns, Australia
Green Chemistry News Archive
Contents list for Green Chemistry, issue 11, 2009
Front cover
Green Chem., 2009, 11, 1705
DOI: 10.1039/b921707j

Contents and Highlights in Chemical Technology
Green Chem., 2009, 11, 1707
DOI: 10.1039/b921709f
Tutorial Review
Organic syntheses catalyzed by superacidic metal oxides: sulfated zirconia and related compounds
Kazushi Arata,
Green Chem., 2009, 11, 1719
DOI: 10.1039/b822795k

Recent studies on organic syntheses catalyzed by solid superacids, sulfate-supported metal oxides and tungsten- or molybdenum-supported metal oxides, are reviewed, offering new opportunities for developing environmentally benign and friendly processes.
Communications
Solvent free base catalysis and transesterification over basic functionalised Metal-Organic Frameworks
Marie Savonnet, Sonia Aguado, Ugo Ravon, Delphine Bazer-Bachi, Vincent Lecocq, Nicolas Bats, Catherine Pinel and David Farrusseng,
Green Chem., 2009, 11, 1729
DOI: 10.1039/b915291c

Metal-Organic Frameworks (post-)functionalised with nitrogen containing moieties undergo solvent free aza-Michael condensation and transesterification, surpassing functionalised MCM-type catalysts.
Solkane® 365mfc is an environmentally benign alternative solvent for trifluoromethylation reactions
Akihiro Kusuda, Hiroyuki Kawai, Shuichi Nakamura and Norio Shibata,
Green Chem., 2009, 11, 1733
DOI: 10.1039/b913984b

Solkane 365mfc is introduced for the first time as a new, environmentally benign alternative solvent for nucleophilic trifluoromethylation reactions.
An efficient aqueous microwave-assisted Suzuki–Miyaura cross-coupling reaction in the thiazole series
Anita Cohen, Maxime D. Crozet, Pascal Rathelot and Patrice Vanelle,
Green Chem., 2009, 11, 1736
DOI: 10.1039/b916123f

A new simple, rapid and high yielding synthesis of various 5-substituted thiazoles by Suzuki–Miyaura cross-coupling reaction is described using microwave irradiation in aqueous medium without organic co-solvent in the presence of tetrabutylammonium bromide.
Efficient and highly regioselective acylation of andrographolide catalyzed by lipase in acetone
Zhi Gang Chen, Ren Xiang Tan and Lin Cao,
Green Chem., 2009, 11, 1743
DOI: 10.1039/b915093e

Regioselective enzymatic acylation of andrographolide with vinyl acetate in acetone was successfully carried out for the first time. Novozym 435 was the most efficient biocatalyst and 14-acetylandrographolide was formed exclusively.
Efficient conversion of glucose into 5-hydroxymethylfurfural catalyzed by a common Lewis acid SnCl4 in an ionic liquid
Suqin Hu, Zhaofu Zhang, Jinliang Song, Yinxi Zhou and Buxing Han,
Green Chem., 2009, 11, 1746
DOI: 10.1039/b914601f

The common Lewis acid SnCl4 was an efficient catalyst for conversion of glucose into 5-hydroxymethylfurfural in [EMim]BF4. The catalytic system is also very effective for the conversion of sucrose, cellobiose and starch.
Enantioselective aldol reaction of cyclic ketones with aryl aldehydes catalyzed by a cyclohexanediamine derived salt in the presence of water
Jin-Hong Lin, Cheng-Pan Zhang and Ji-Chang Xiao,
Green Chem., 2009, 11, 1750
DOI: 10.1039/b916583e

Water was found to be a suitable reaction medium for the direct asymmetric aldol reaction of various cyclic ketones with aryl aldehydes catalyzed by a primary-tertiary diamine-Brønsted acid.
Selective production of cyclic carbonate over polycarbonate using a double metal cyanide–quaternary ammonium salt catalyst system
Manju Mamparambath Dharman, Jeong-In Yu, Ji-Yeon Ahn and Dae-Won Park,
Green Chem., 2009, 11, 1754
DOI: 10.1039/b916875n

A new catalyst system comprising a double metal cyanide complex with quaternary ammonium salts is derived for the cycloaddition of CO2 to epoxide.
Bionanocomposites formed by in situ charged chitosan with clay
Yury Shchipunov, Nadya Ivanova and Vladimir Silant'ev,
Green Chem., 2009, 11, 1758
DOI: 10.1039/b914548f

Bionanocomposites are formed through the electrostatic interactions of exfoliated clay nanoparticles with chitosan macromolecules that are gradually charged in the course of a progressive pH decrease by chemical acidulating agent.
Perdeuterated pyridinium molten salt (ionic liquid) for direct dissolution and NMR analysis of plant cell walls
Nan Jiang, Yunqiao Pu, Reichel Samuel and Arthur J. Ragauskas,
Green Chem., 2009, 11, 1762
DOI: 10.1039/b913609f

A bi-solvent system consisting of a perdeuterated pyridinium molten salt and DMSO-d6 has been developed for direct dissolution and NMR analysis of plant cell walls.
Papers
Glycerol as a promoting medium for electrophilic activation of aldehydes: catalyst-free synthesis of di(indolyl)methanes, xanthene-1,8(2H)-diones and 1-oxo-hexahydroxanthenes
Fei He, Peng Li, Yanlong Gu and Guangxing Li,
Green Chem., 2009, 11, 1767
DOI: 10.1039/b916015a

The first use of glycerol as an effective promoting medium for activation of aldehydes, leading to a catalyst-free synthesis of di(indolyl)methanes, xanthene diones and oxo-hexahydroxanthenes.
Boron trifluoride catalyzed ring-opening polymerization of epoxidized soybean oil in liquid carbon dioxide
Zengshe Liu, Kenneth M. Doll and Ronald A. Holser,
Green Chem., 2009, 11, 1774
DOI: 10.1039/b915742p

Epoxidized soybean oil was polymerized in liquid carbon dioxide at room temperature. BF3·OEt2 was used as initiator. The resulting polymers were characterized by 1H and 13C NMR, and size exclusion chromatography. These new biodegradable polymers from a
green
processing method are highly desirable: they may be used as ingredients in personal care, health care and controlled release drugs after chemical modifications.
Stabilisation of Pd(0) on surface functionalised Fe3O4 nanoparticles: magnetically recoverable and stable recyclable catalyst for hydrogenation and Suzuki–Miyaura reactions
Arlin Jose Amali and Rohit Kumar Rana,
Green Chem., 2009, 11, 1781
DOI: 10.1039/b916261p

Highly branched polyethylenimine functionalisation on the surface of Fe3O4 nanoparticles enables stabilisation of Pd nanoparticles leading to a magnetically separable, efficient and recyclable catalyst for hydrogenation and ligand-free Suzuki–Miyaura reactions.
Strategies for cleaner oxidations using photochemically generated singlet oxygen in supercritical carbon dioxide
Xue Han, Richard A. Bourne, Martyn Poliakoff and Michael W. George,
Green Chem., 2009, 11, 1787
DOI: 10.1039/b914074c

Singlet oxygen has been reacted with four substrates in scCO2 using a variety of different coloured photosensitisers in combination with fluorous surfactants and a co-solvent to extend the applicability of photo-oxidation in scCO2.
Ionic liquid-coated immobilized lipase for the synthesis of methylglucose fatty acid esters
Julien Mutschler, Thierry Rausis, Jean-Marc Bourgeois, Christèle Bastian, Daniel Zufferey, Isabelle Vanessa Mohrenz and Fabian Fischer,
Green Chem., 2009, 11, 1793
DOI: 10.1039/b916016g

Ionic liquid film coated lipase beads for solvent free sustainable biotransformation of methylglucose with fatty acids.
Deep oxidative desulfurization of fuels by Fenton-like reagent in ionic liquids
Jingtong Zhang, Wenshuai Zhu, Huaming Li, Wei Jiang, Yunqing Jiang, Wangli Huang and Yongsheng Yan,
Green Chem., 2009, 11, 1801
DOI: 10.1039/b914130h

The Fenton-like desulfurization system containing anhydrous FeCl3, H2O2 and [bmim]BF4 could achieve deep desulfurization, which was superior to extractive desulfurization with [bmim]BF4 or oxidative desulfurization without [bmim]BF4.
Enzymatic-mediated production of cellulose nanocrystals from recycled pulp
Paul B. Filson, Benjamin E. Dawson-Andoh and Diane Schwegler-Berry,
Green Chem., 2009, 11, 1808
DOI: 10.1039/b915746h

Endoglucanase was used to hydrolyze recycled pulp using microwave and conventional heating to produce cellulose nanocrystals with dimensions, widths (30–80 nm) and lengths (100 nm to 1.8
m).
Organic–inorganic hybrid silica materials containing imidazolium and dihydroimidazolium salts as recyclable organocatalysts for Knoevenagel condensations
Montserrat Trilla, Roser Pleixats, Michel Wong Chi Man and Catherine Bied,
Green Chem., 2009, 11, 1815
DOI: 10.1039/b916767f

Organic–inorganic hybrid silicas containing dihydroimidazolium salts are efficient reusable organocatalysts for the Knoevenagel condensation of aromatic aldehydes with malononitrile and ethyl cyanoacetate under solvent-free conditions.
Solvent-free Sonogashira coupling reaction via high speed ball milling
Dennis A. Fulmer, William C. Shearouse, Shareika T. Medonza and James Mack,
Green Chem., 2009, 11, 1821
DOI: 10.1039/b915669k

Herein, we report on the solvent-free Sonogashira reaction utilizing high speed ball milling. When the reaction is conducted in a copper vial in lieu of copper iodide, the reaction gives the coupling product in high yields. This demonstrates the first report on the use of the vial and ball material as a catalyst in a ball milled chemical reaction.
Bridging data gaps in environmental assessments: Modeling impacts of fine and basic chemical production
Gregor Wernet, Stavros Papadokonstantakis, Stefanie Hellweg and Konrad Hungerbühler,
Green Chem., 2009, 11, 1826
DOI: 10.1039/b905558d

Models to predict the environmental impacts of chemical production from a life cycle perspective have been created. The models use only the molecular structure as input while still being adequate for many purposes.
Low catalyst loading ligand-free palladium-catalyzed direct arylation of furans: an economically and environmentally attractive access to 5-arylfurans
Jia Jia Dong, Julien Roger, Franc Po
gan and Henri Doucet,
Green Chem., 2009, 11, 1832
DOI: 10.1039/b915290n

The direct 5-arylation of furans at very low catalyst loading using Pd(OAc)2 as catalyst without added ligand proceed in high yields. Turnover numbers up to 10000 have been obtained for the coupling of several activated aryl bromides. A wide range of functions on the furan or aryl bromide is tolerated.
Study on selectivity of
-myrcene hydrogenation in high-pressure carbon dioxide catalysed by noble metal catalysts
E. Bogel-
ukasik, M. Gomes da Silva, I. D. Nogueira, R. Bogel-
ukasik and M. Nunes da Ponte,
Green Chem., 2009, 11, 1847
DOI: 10.1039/b916017p

Selective hydrogenation of a three double bond terpene (
-myrcene) in supercritical carbon dioxide catalysed by noble metal catalysts is presented.
Metal free oxidation of alkyl substituted aromatics with aqueous tert-butyl hydroperoxide under microwave irradiation
Hao He, Bao-Jian Pei and Albert W. M. Lee,
Green Chem., 2009, 11, 1857
DOI: 10.1039/b916265h

70% aqueous TBHP (tert-butyl hydroperoxide) with microwave irradiation is a green oxidation protocol for alkyl substituted aromatics to ketones and carboxylic acids without the use of metal based reagent or catalyst.
Preparation of Na doped SiO2 solid catalysts by the sol-gel method for the production of biodiesel from jatropha oil
Emil Akbar, Narayanan Binitha, Zahira Yaakob, Siti Kartom Kamarudin and Jumat Salimon,
Green Chem., 2009, 11, 1862
DOI: 10.1039/b916263c

Biodiesel production is performed by transesterification of jatropha oil over solid catalysts, Na/SiO2, to form fatty acid methyl esters with very high yield under mild conditions of operation.
Green photochemistry: photo-Friedel–Crafts acylations of 1,4-naphthoquinone in room temperature ionic liquids
Brian Murphy, Peter Goodrich, Christopher Hardacre and Michael Oelgemöller,
Green Chem., 2009, 11, 1867
DOI: 10.1039/b913252j

The photo-Friedel–Crafts acylation of 1,4-naphthoquinone with aldehydes was investigated in ionic liquids. High conversions and selectivities were achieved in [C2mim]+-based ionic liquids. The procedure allowed for a replacement of the hazardous solvent benzene.
Diethyl carbonate as a solvent for ruthenium catalysed C–H bond functionalisation
Percia Arockiam, Valentin Poirier, Cédric Fischmeister, Christian Bruneau and Pierre H. Dixneuf,
Green Chem., 2009, 11, 1871
DOI: 10.1039/b913115a

The present article describes efficient ruthenium-based catalysts for the functionalisation of sp2 C–H bonds with aryl chlorides. These catalysts were employed in diethyl carbonate, an eco-friendly solvent.
Silica-supported aminopyridinium halides for catalytic transformations of epoxides to cyclic carbonates under atmospheric pressure of carbon dioxide
Ken Motokura, Shintaro Itagaki, Yasuhiro Iwasawa, Akimitsu Miyaji and Toshihide Baba,
Green Chem., 2009, 11, 1876
DOI: 10.1039/b916764c

Silica-supported 4-pyrrolidinopyridinium iodide showed excellent catalytic performance for transformations of various epoxides to cyclic carbonates under atmospheric pressure of carbon dioxide.
Microwave-assisted synthesis of quinazolinone derivatives by efficient and rapid iron-catalyzed cyclization in water
Xiaodong Zhang, Deju Ye, Haifeng Sun, Diliang Guo, Jiang Wang, He Huang, Xu Zhang, Hualiang Jiang and Hong Liu,
Green Chem., 2009, 11, 1881
DOI: 10.1039/b916124b

A green, rapid, and efficient method was developed for synthesizing quinazolinone derivatives from substituted 2-halobenzoic acids and amidines via microwave-assisted iron-catalyzed cyclization in water without ligand.
Green photocatalytic synthesis of stable Au and Ag nanoparticles
Pedro Quaresma, Leonor Soares, Lívia Contar, Adelaide Miranda, Inês Osório, Patrícia A. Carvalho, Ricardo Franco and Eulália Pereira,
Green Chem., 2009, 11, 1889
DOI: 10.1039/b917203n

Stable Au and Ag nanoparticles were synthesized using a novel green photocatalytic method.
Energetic assessment of the Suzuki–Miyaura reaction: a curtate life cycle assessment as an easily understandable and applicable tool for reaction optimization
Franziska Schneider, Tony Szuppa, Achim Stolle, Bernd Ondruschka and Henning Hopf,
Green Chem., 2009, 11, 1894
DOI: 10.1039/b915744c

Solvent-free KF–Al2O3-assisted Suzuki–Miyaura coupling was used as an example reaction to assess different reaction technologies for greener synthetic procedures.
Vegetables as biocatalysts in stereoselective hydrolysis of labile organic compounds
Björn Bohman, L. R. Cavonius and C. Rikard Unelius,
Green Chem., 2009, 11, 1900
DOI: 10.1039/b913936b

A general unprecedented method for the mild and stereoselective hydrolysis of secondary
-alkoxy- and
-aryloxyketones in aqueous solution, mediated by whole plant tissue from eight vegetables, is presented.
Water as the medium of choice for the 1,3-dipolar cycloaddition reactions of hydrophobic nitrones
Evdoxia Coutouli-Argyropoulou, Prodromos Sarridis and Petros Gkizis,
Green Chem., 2009, 11, 1906
DOI: 10.1039/b916765j

1,3-Dipolar cycloadditions of hydrophobic nitrones with acrylates in water suspensions showed great rate accelerations over homogenous solutions. Small changes were also observed to the stereoselectivities of the reactions. Hydrophobic interactions are invoked for the observed behaviour.
Back cover
Green Chem., 2009, 11, 1915
DOI: 10.1039/b921708h




