N-Butylpyrrolidinone as a dipolar aprotic solvent for organic synthesis

Green Chem., 2016, Advance Article
DOI: 10.1039/C6GC00932H, Paper
James Sherwood, Helen L. Parker, Kristof Moonen, Thomas J. Farmer, Andrew J. Hunt
N-Butylpyrrolidinone (NBP) has been demonstrated as a suitable safer replacement solvent for N-Methylpyrrolidinone (NMP) in selected organic syntheses.

N-Butylpyrrolidinone as a dipolar aprotic solvent for organic synthesis

*Corresponding authors
aGreen Chemistry Centre of Excellence, Department of Chemistry, University of York, UK
E-mail: andrew.hunt@york.ac.uk
bEastman Chemical Company, Pantserschipstraat 207 – B-9000, Gent, Belgium
Green Chem., 2016, Advance Article

DOI: 10.1039/C6GC00932H

Dipolar aprotic solvents such as N-methylpyrrolidinone (or 1-methyl-2-pyrrolidone (NMP)) are under increasing pressure from environmental regulation. NMP is a known reproductive toxin and has been placed on the EU “Substances of Very High Concern” list. Accordingly there is an urgent need for non-toxic alternatives to the dipolar aprotic solvents. N-Butylpyrrolidinone, although structurally similar to NMP, is not mutagenic or reprotoxic, yet retains many of the characteristics of a dipolar aprotic solvent. This work introduces N-butylpyrrolidinone as a new solvent for cross-coupling reactions and other syntheses typically requiring a conventional dipolar aprotic solvent.

 

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////N-Butylpyrrolidinone, dipolar aprotic solvent , organic synthesis

Organocatalytic 1,3-dipolar cycloaddition reactions of ketones and azides with water as a solvent

 

Green Chem., 2013, 15,2384-2388
DOI: 10.1039/C3GC41126E, Communication
*
Corresponding authors
a
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore
E-mail: chmwangj@nus.edu.sg ;
Fax: (+)65-6516-1691
b
HuBei Collaborative Innovation Center of Non-power Nuclear Technology, Hubei University of Science and Technology, Hubei Province, China

Received 12 Jun 2013, Accepted 19 Jul 2013
First published online 22 Jul 2013

We reported an enamine catalyzed strategy to fully promote a 1,3-dipolar cycloaddition to access a vast pool of substituted 1,2,3-triazoles in water.

Porous Organic Polymer Captures CO2

 

 

 

 

 

A moisture-stable porous organic polymer containing carboxy and triazole groups reversibly and selectively captures carbon dioxide

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Large-ring lactones from plant oils

 

Timo Witta and   Stefan Mecking*a  
Chair of Chemical Materials Science, University of Konstanz, Department of Chemistry, Universitätsstraße 10, 78457 Konstanz, Germany 
E-mail: stefan.mecking@uni-konstanz.de ;
Fax: +49 7531 885152 ;
Tel: +49 7531 882593
 
Green Chem., 2013, Advance Article

DOI: 10.1039/C3GC40905H
Received 15 May 2013, Accepted 11 Jul 2013
First published online 29 Jul 2013
A synthesis route for macrocyclic compounds such as lactones starting from common plant oils has been developed.
Large-ring lactones from plant oils

 
 
Large-ring lactones and lactams were prepared utilising the full fatty acid chain of common plant oils as a source of the macrocycle. Ring closure via acyloin condensation does not require large volumes of solvents for dilution. Nonadecalactone (NDL) and tricosalactone (TCL) can be converted to novel polyesters by ring opening.

Watermelon Juice Prevents Aching Muscles Food Chemistry: The amino acid L-citrulline found in the fruit could help athletes avoid muscle soreness after a hard workout

Photo of watermelon juice smoothie in tall glass

The Next Sports Drink?
Watermelon drinks, like this smoothie, could help cut down on muscle soreness after intense exercise.
Credit: Shutterstock
Before taking a long bike ride on a hot summer day, have some watermelon: The juicy fruit may ward off muscle pains. Researchers report that people who drank watermelon juice before exercising felt less sore the next day than those who drank a pink placebo beverage (J. Agric. Food Chem. 2013, DOI: 10.1021/jf400964r). They also found that cells absorb the presumed active ingredient, L-citrulline, more readily from unpasteurized watermelon juice than from plain water spiked with the compound, suggesting the natural source is the optimal delivery
medium.