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Symposium report: Transitioning into Green Chemistry
28 May 2009
Read the report by Tyson Miller and colleagues on the 7th American Chemical Society Graduate Student Symposium - Transitioning into Green Chemistry.
Fighting MRSA with ionic liquids
06 March 2009
Hospital cleaners may one day use ionic liquids to clean wards
Contents list for Green Chemistry, issue 6, 2009
Front cover
Green Chem., 2009, 11, 741
DOI: 10.1039/b910365c
Inside front cover
Green Chem., 2009, 11, 742
DOI: 10.1039/b910366j
Contents and Chemical Technology
Green Chem., 2009, 11, 743
DOI: 10.1039/b910367h
Communications
An efficient synthesis of glyceryl ethers: catalyst-free hydrolysis of glycidyl ethers in water media
Akira Saito, Takeshi Shirasawa, Shinichiro Tanahashi, Mitsuru Uno, Nobuhiro Tatsumi and Tomohito Kitsuki,
Green Chem., 2009, 11, 753
DOI: 10.1039/b821881a
Hydrolysis of hydrophobic glycidyl ethers in pressurized water media afforded the corresponding glycidyl ethers in good to excellent selectivity within several minutes without catalyst.
A green and efficient oxidation of alcohols by supported gold catalysts using aqueous H2O2 under organic solvent-free conditions
Ji Ni, Wen-Jian Yu, Lin He, Hao Sun, Yong Cao, He-Yong He and Kang-Nian Fan,
Green Chem., 2009, 11, 756
DOI: 10.1039/b820197h
The use of supported gold nanoparticles as an efficient, green and reusable catalyst for the oxidation of various alcohols to the corresponding carbonyl compounds using aqueous hydrogen peroxide as an environmentally benign oxidant is presented.
Synthesis of novel 6-[N,N-bis(2-hydroxyethyl)amino]purine nucleosides under microwave irradiation in neat water
Gui-Rong Qu, Jing Wu, Yan-Yan Wu, Feng Zhang and Hai-Ming Guo,
Green Chem., 2009, 11, 760
DOI: 10.1039/b902025j
Novel 6-[N,N-bis(2-hydroxyethyl)amino]purine nucleosides were prepared in one step by nucleophilic substitution reaction of 6-choloropurine nucleosides with diethanolamine. Shorter reaction times and higher yields were achieved under microwave irradiation conditions in neat water.
Highly-selective and high-speed Claisen rearrangement induced with subcritical water microreaction in the absence of catalyst
Masahiro Sato, Nobuhiro Otabe, Tomoya Tuji, Keiichiro Matsushima, Hajime Kawanami, Maya Chatterjee, Toshiro Yokoyama, Yutaka Ikushima and Toshishige Maro Suzuki,
Green Chem., 2009, 11, 763
DOI: 10.1039/b819106a
Highly-selective, high-speed Claisen rearrangement was shown to give the corresponding product in a excellent yield over 90% induced by subcritical water microreaction in the absence of catalyst.
Highly enantioselective hydrogenation of quinolines under solvent-free or highly concentrated conditions
Zhi-Jian Wang, Hai-Feng Zhou, Tian-Li Wang, Yan-Mei He and Qing-Hua Fan,
Green Chem., 2009, 11, 767
DOI: 10.1039/b822822a
The phosphine-free chiral cationic Ru(OTf)(TsDPEN)(
6-cymene) complex was found to be an efficient catalyst for the enantioselective hydrogenation of quinolines under more environmentally friendly solvent-free or highly concentrated conditions with excellent yields and high enantioselectivities (up to 97% ee) at only 0.02–0.10 mol% catalyst loading.
General MW-assisted grafting of MCM-41: Study of the dependence on time dielectric heating and solvent
Antonio Procopio, Giuseppina De Luca, Monica Nardi, Manuela Oliverio and Rosina Paonessa,
Green Chem., 2009, 11, 770
DOI: 10.1039/b820417a
A fast and versatile MW-assisted method for the post-calcination functionalization of MCM-41 is proposed. The efficiency of the grafting is improved in the absence of solvent and depends on the MW-heating time.
Microwave-promoted mono-N-alkylation of aromatic amines in water: a new efficient and green method for an old and problematic reaction
Giovanni Marzaro, Adriano Guiotto and Adriana Chilin,
Green Chem., 2009, 11, 774
DOI: 10.1039/b900750d
A greener improvement to direct mono-N-alkylation of aromatic amines by alkyl halides was achieved using microwave irradiation in water without any catalyst.
Lipase-catalysed direct Mannich reaction in water: utilization of biocatalytic promiscuity for C–C bond formation in a 
one-pot
synthesis
Kun Li, Ting He, Chao Li, Xing-Wen Feng, Na Wang and Xiao-Qi Yu,
Green Chem., 2009, 11, 777
DOI: 10.1039/b817524a
Lipase-catalysed direct Mannich reaction, which is the first example of three-component biocatalytic promiscuity for C–C bond formation. Aromatic aldehyde, aniline and acetone reacted in one-pot to form 
-amino-ketone compounds in water with high yield.
Papers
Phase behaviour of trihexyl(tetradecyl)phosphonium chloride, nonane and water
Kris Anderson, Héctor Rodríguez and Kenneth R. Seddon,
Green Chem., 2009, 11, 780
DOI: 10.1039/b821925g
The mixture of trihexyl(tetradecyl)phosphonium chloride, water and nonane can form a stable three-phase system in equilibrium, in which the upper phase is virtually pure nonane, and the lower phase is virtually pure water.
Activity and thermal stability of lysozyme in alkylammonium formate ionic liquids—influence of cation modification
Jason P. Mann, Adam McCluskey and Rob Atkin,
Green Chem., 2009, 11, 785
DOI: 10.1039/b900021f
Variation in the cation molecular structure of protic room temperature ionic liquids produces remarkable differences in the thermal stability and activity of lysozyme. Results suggest specific interactions between the cation and enzyme.
Supported gold nanoparticles as a reusable catalyst for synthesis of lactones from diols using molecular oxygen as an oxidant under mild conditions
Takato Mitsudome, Akifumi Noujima, Tomoo Mizugaki, Koichiro Jitsukawa and Kiyotomi Kaneda,
Green Chem., 2009, 11, 793
DOI: 10.1039/b900576e
Hydrotalcite-supported Au nanoparticles acted as a highly efficient heterogeneous catalyst for the oxidative lactonization of various diols using molecular oxygen as a primary oxidant under mild reaction conditions. The solid Au catalyst was readily reusable without any loss of its activity and selectivity.
Cross-linked polymer coated Pd nanocatalysts on SiO2 support: very selective and stable catalysts for hydrogenation in supercritical CO2
Tianbin Wu, Tao Jiang, Baoji Hu, Buxing Han, Jinling He and Xiaosi Zhou,
Green Chem., 2009, 11, 798
DOI: 10.1039/b822930a
Cross-linked polystyrene-coated Pd(0) nanoparticle catalysts on the surface of silica were prepared, which were very selective and stable for the selective hydrogenation of 2,4-dimethyl-1,3-pentadiene to produce 2, 4-dimethyl-2-pentene and ally alcohol to produce 1-propanol; supercritical CO2 can enhance the reaction rate significantly.
N-alkylation of N-heterocyclic ionic liquid precursors in ionic liquids
Thomas Rüther, Tamsyn Ross, Emily J. Mensforth and Anthony Frank Hollenkamp,
Green Chem., 2009, 11, 804
DOI: 10.1039/b817526h
Room temperature ionic liquids [BMIM][PF6] and [P14][Tf2N] in conjunction with KOH are superior reaction media for the alkylation of the secondary amine 3-azabicyclo[3.2.2]nonane under mild conditions.
Deep oxidative desulfurization of fuels in redox ionic liquids based on iron chloride
Huaming Li, Wenshuai Zhu, Yan Wang, Jingtong Zhang, Jidong Lu and Yongsheng Yan,
Green Chem., 2009, 11, 810
DOI: 10.1039/b901127g
Redox ionic liquids based on iron chloride were employed in extraction coupled with an oxidative desulfurization system for removal of dibenzothiophene in a model oil.
Catalytic aerobic oxidation of allylic alcohols to carbonyl compounds under mild conditions
Lucia Tonucci, Marco Nicastro, Nicola d'Alessandro, Mario Bressan, Primiano D'Ambrosio and Antonino Morvillo,
Green Chem., 2009, 11, 816
DOI: 10.1039/b813019a
A new catalytic aerobic oxidation of alcohols to aldehydes under green conditions.
Further investigation of the biodegradability of imidazolium ionic liquids
Jitendra R. Harjani, Jeff Farrell, M. Teresa Garcia, Robert D. Singer and Peter J. Scammells,
Green Chem., 2009, 11, 821
DOI: 10.1039/b900787c
The structure–biodegradability relationships of a variety of imidazolium ionic liquids was investigated using the CO2 headspace test (ISO 14593, OECD 310).
An efficient copper-catalytic system for performing intramolecular O-arylation reactions in aqueous media. New synthesis of xanthones
Nekane Barbero, Raul SanMartin and Esther Domínguez,
Green Chem., 2009, 11, 830
DOI: 10.1039/b900931k
A safe, efficient and scalable protocol for the copper-catalysed intramolecular O-arylation of 2-halobenzophenones on water to afford the valuable xanthone framework is reported.
Designing systems for one-way trans to cis photoisomerization for solar reactions
Yao-Peng Zhao, Lan-Ying Yang and Robert S. H. Liu,
Green Chem., 2009, 11, 837
DOI: 10.1039/b819207c
One-way trans to cis isomerizations were achieved under selective triplet sensitization for several derivatives of hindered isomers of stilbene, styrene, diene and triene. The reaction conditions were particularly suitable for preparation of the hindered cis isomers under solar irradiation, using in our case a kick-board reactor.
Solvent-free synthesis of unsaturated ketones by the Saucy–Marbet reaction using simple ammonium ionic liquid as a catalyst
Congmin Wang, Wenjia Zhao, Haoran Li and Liping Guo,
Green Chem., 2009, 11, 843
DOI: 10.1039/b900042a
Simple ammonium ionic liquids are used as highly efficient catalysts for Saucy–Marbet reactions to synthesize unsaturated ketones from unsaturated alcohols and unsaturated ethers, eliminating the need for volatile organic solvents.
Organic reactions in low melting mixtures based on carbohydrates and L-carnitine—a comparison
Florian Ilgen and Burkhard König,
Green Chem., 2009, 11, 848
DOI: 10.1039/b816551c
An L-carnitine/urea melt was developed and compared to previously reported sugar and sugar alcohol melts using several organic reactions for benchmarking.
Regioselective enzymatic acylation of pharmacologically interesting nucleosides in 2-methyltetrahydrofuran, a greener substitute for THF
Yolanda Simeó, José Vicente Sinisterra and Andrés R. Alcántara,
Green Chem., 2009, 11, 855
DOI: 10.1039/b818992g
Generally, reactions proceeded in short reaction times with excellent yield and regioselectivity. For ara-U and uridine, MeTHF (environmentally friendlier than THF) was successfully used. This application for this green solvent is a proof-of-concept opening the use of MeTHF in biotransformations.
Solvent-free condensations of ketones with malononitrile catalysed by methanesulfonic acid/morpholine system
M. Góra, B. Kozik, K. Jamro
y, M. K. 
uczy
ski, P. Brzuzan and M. Wo
ny,
Green Chem., 2009, 11, 863
DOI: 10.1039/b820901d
The new, alternative and greener route for Knoevenagel condensations of ketones with malononitrile without the need for organic solvents is described.
An efficient, practical and cost-effective polymer-supported catalyst for the transesterification of methyl methacrylate by 1-butanol
Gaëlle Baquey, Marie-Hélène Alvès, Magalie Graullier, Alain Riondel, Jean-Michel Paul, Marc Birot and Hervé Deleuze,
Green Chem., 2009, 11, 868
DOI: 10.1039/b820704f
Cheap and efficient polymer-supported titanium alkoxide catalyst with a very low metal leaching under continuous use as alternative of a homogeneous industrial transesterification process.
Direct conversion of inulin to 5-hydroxymethylfurfural in biorenewable ionic liquids
Suqin Hu, Zhaofu Zhang, Yinxi Zhou, Jinliang Song, Honglei Fan and Buxing Han,
Green Chem., 2009, 11, 873
DOI: 10.1039/b822328a
The non digestible inulin stored in many plants can be directly converted to 5-hydroxymethylfurfural (HMF) in acidic biorenewable ionic liquids (ILs) with a good yield. The IL can be recycled easily with high activity.
Catalyst-free, step and pot economic, efficient mercaptoacetylative cyclisation in H2O: synthesis of 3-mercaptocoumarins
Lal Dhar S. Yadav, Santosh Singh and Vijai K. Rai,
Green Chem., 2009, 11, 878
DOI: 10.1039/b904655k
An environmentally friendly, tandem Knoevenagel condensation and mercaptoacetylative cyclisation procedure is reported. The reaction between 2-methyl-2-phenyl-1,3-oxathiolan-5-one and a variety of salicylaldehydes was carried out in water to afford 3-mercaptocoumarins in excellent yields (82–97%).
Desulfurization of dibenzothiophene by chemical oxidation and solvent extraction with Me3NCH2C6H5Cl·2ZnCl2 ionic liquid
Fa-tang Li, Rui-hong Liu, Jin-hua Wen, Di-shun Zhao, Zhi-min Sun and Ying Liu,
Green Chem., 2009, 11, 883
DOI: 10.1039/b815575e
The Me3NCH2C6H5Cl·2ZnCl2 ionic liquid was prepared and found to be a highly efficient extractant for oxidative desulfurization of dibenzothiophene. The sulfur removal could reach 94% within 30 min in the presence of H2O2 and AcOH.
Exploring fungal activity in the presence of ionic liquids
M. Petkovic, J. Ferguson, A. Bohn, J. Trindade, I. Martins, M. B. Carvalho, M. C. Leitão, C. Rodrigues, H. Garcia, R. Ferreira, K. R. Seddon, L. P. N. Rebelo and C. Silva Pereira,
Green Chem., 2009, 11, 889
DOI: 10.1039/b823225c
The toxicological assessment towards filamentous fungi (Penicillium sp.) as model eukaryotic organisms of sixteen ionic liquids is presented; the metabolic footprint, as investigated by mass spectrometry, revealed that fungal cultures respond to specific ionic liquids by changing their cell biochemistry.
Back cover
Green Chem., 2009, 11, 895
DOI: 10.1039/b910369b
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