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Wednesday, 21 August 2013

Direct synthesis of hydrogen peroxide in water in a continuous trickle bed reactor optimized to maximize productivity



Hydrogen peroxide direct synthesis was studied in continuous mode over a 5% wt Pd/C commercial catalyst in a Trickle Bed Reactor. The target of the study was to maximize the hydrogen peroxide production. The catalyst was uniformly diluted in quartz sand at different concentrations to investigate their effects on the direct synthesis.
The amount of catalyst and the distribution of the catalyst along the bed were optimized to obtain the highest possible yield. The distribution of the catalyst along the bed gave the possibility to significantly improve the selectivity and production of hydrogen peroxide (up to 0.5% under selected conditions). Higher production rate and selectivity were found when the catalyst concentration was decreased along the bed from the top to the bottom as compared to the uniformly dispersed catalyst.
The H2/Pd ratio was found to be an important parameter that has to be investigated in the hydrogen peroxide direct synthesis. The effect of a pretreatment of the catalyst with a solution of sodium bromide and phosphoric acid was studied; the results showed how a catalyst pretreatment can lead to a real green hydrogen peroxide synthesis in water. Some optimization guidelines are also provided.
Green Chem., 2013, 15,2502-2513
DOI: 10.1039/C3GC40811F, Paper


*
Corresponding authors
a
Department of Chemical Engineering, Åbo Akademi University, Turku/Åbo, Finland
E-mail: bpierdom@abo.fi ;
Fax: +358 2 215 4479 ;
Tel: +358 2 215 4555
b
Department of Chemical Engineering and Environmental Technology, University of Valladolid, Valladolid, Spain
E-mail: jgserna@iq.uva.es
Hydrogen peroxide direct synthesis was studied in continuous mode over a 5% wt Pd/C commercial catalyst in a Trickle Bed Reactor.

Iodine-mediated arylation of benzoxazoles with aldehydes



A simple and efficient methodology for the arylation of benzoxazoles with aldehydes using iodine as the mediator has been developed. The reaction proceeded smoothly with a range of substrates to give the corresponding arylated products in moderate to good yields
Green Chem., 2013, 15,2365-2368
DOI: 10.1039/C3GC41027G, Communication


*
Corresponding authors
a
Institute of Bioengineering and Nanotechnology, 31 Biopolis Way, The Nanos, Singapore 138669, Singapore
E-mail: ygzhang@ibn.a-star.edu.sg ;
Fax: (+65) 6478-9020
A simple and efficient methodology for the arylation of benzoxazoles with aldehydes using iodine as the mediator has been developed

Wednesday, 7 August 2013

A synthesis of α-amino acids via direct reductive carboxylation of imines with carbon dioxide

Graphical abstract: A synthesis of α-amino acids via direct reductive carboxylation of imines with carbon dioxide
A method for the synthesis of α-amino acids by direct reductive carboxylation of aromatic imines with CO2 is described. The protocol employs readily available commercial reagents and serves as a one-step alternative to the Strecker synthesis.

A synthesis of α-amino acids via direct reductive carboxylation of imines with carbon dioxide


* Corresponding authors
a
Department of Chemistry, The Pennsylvania State University, University Park, USA 
E-mail: radosevich@psu.edu ;
Tel: +1 814 867 4268
Chem. Commun., 2013,49, 5040-5042

DOI: 10.1039/C3CC42057D
Received 21 Mar 2013, Accepted 16 Apr 2013
First published online 25 Apr 2013

Friday, 2 August 2013

COLUMN CHROMATOGRAPHY


A chemist in the 1950s using column chromatography. The Erlenmeyer receptacles are on the floor.
Column chromatography in chemistry is a method used to purify individual chemical compounds from mixtures of compounds. It is often used for preparative applications on scales from micrograms up to kilograms. The main advantage of column chromatography is the relatively low cost and disposability of the stationary phase used in the process. The latter prevents cross-contamination and stationary phase degradation due to recycling.
The classical preparative chromatography column, is a glass tube with a diameter from 5 mm to 50 mm and a height of 5 cm to 1 m with a tap and some kind of a filter (a glass frit or glass wool plug – to prevent the loss of the stationary phase) at the bottom. Two methods are generally used to prepare a column: the dry method, and the wet method.
  • For the dry method, the column is first filled with dry stationary phase powder, followed by the addition of mobile phase, which is flushed through the column until it is completely wet, and from this point is never allowed to run dry.
  • For the wet method, a slurry is prepared of the eluent with the stationary phase powder and then carefully poured into the column. Care must be taken to avoid air bubbles. A solution of the organic material is pipetted on top of the stationary phase. This layer is usually topped with a small layer of sand or with cotton or glass wool to protect the shape of the organic layer from the velocity of newly added eluent. Eluent is slowly passed through the column to advance the organic material. Often a spherical eluent reservoir or an eluent-filled and stoppered separating funnel is put on top of the column.
The individual components are retained by the stationary phase differently and separate from each other while they are running at different speeds through the column with the eluent. At the end of the column they elute one at a time. During the entire chromatography process the eluent is collected in a series of fractions. Fractions can be collected automatically by means of fraction collectors. The productivity of chromatography can be increased by running several columns at a time. In this case multi stream collectors are used. The composition of the eluent flow can be monitored and each fraction is analyzed for dissolved compounds, e.g. by analytical chromatography, UV absorption, or fluorescence. Colored compounds (or fluorescent compounds with the aid of an UV lamp) can be seen through the glass wall as moving bands.

    Overview


    Stationary phase

    The stationary phase or adsorbent in column chromatography is a solid. The most common stationary phase for column chromatography is silica gel, followed by aluminaCellulosepowder has often been used in the past. Also possible are ion exchange chromatographyreversed-phase chromatography(RP), affinity chromatography or expanded bed adsorption(EBA). The stationary phases are usually finely ground powders or gels and/or are microporous for an increased surface, though in EBA a fluidized bed is used. There is an important ratio between the stationary phase weight and the dry weight of the analyte mixture that can be applied onto the column. For silica column chromatography, this ratio lies within 20:1 to 100:1, depending on how close to each other the analyte components are being eluted.

    Mobile phase (eluent)

    The mobile phase or eluent is either a pure solvent or a mixture of different solvents. It is chosen so that the retention factor value of the compound of interest is roughly around 0.2 - 0.3 in order to minimize the time and the amount of eluent to run the chromatography. The eluent has also been chosen so that the different compounds can be separated effectively. The eluent is optimized in small scale pretests, often using thin layer chromatography (TLC) with the same stationary phase.
    There is an optimum flow rate for each particular separation. A faster flow rate of the eluent minimizes the time required to run a column and thereby minimizes diffusion, resulting in a better separation. However, the maximum flow rate is limited because a finite time is required for analyte to equilibrate between stationary phase and mobile phase, see Van Deemter's equation. A simple laboratory column runs by gravity flow. The flow rate of such a column can be increased by extending the fresh eluent filled column above the top of the stationary phase or decreased by the tap controls. Faster flow rates can be achieved by using a pump or by using compressed gas (e.g. air,nitrogen, or argon) to push the solvent through the column (flash column chromatography).
    The particle size of the stationary phase is generally finer in flash column chromatography than in gravity column chromatography. For example, one of the most widely used silica gel grades in the former technique is mesh 230 – 400 (40 – 63 µm), while the latter technique typically requires mesh 70 – 230 (63 – 200 µm) silica gel.

    A spreadsheet that assists in the successful development of flash columns has been developed. The spreadsheet estimates the retention volume and band volume of analytes, the fraction numbers expected to contain each analyte, and the resolution between adjacent peaks. This information allows users to select optimal parameters for preparative-scale separations before the flash column itself is attempted.



    An automated ion chromatography system.


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    Typical set up for manual column chromatography

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    EROS Best Reagent Award 2013




    Huw Davis, Emory University, USA, has received the the Best Reagent Award for his widely used carbenoid precursor
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    Organic Chemistry Becomes Multidisciplinary








    18th European Symposium on Organic Chemistry (ESOC 2013) sees future trends in close connection to biology, physics, and materials science
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    Jumping Crystals








    Scientists from the United Arab Emirates and Russia examined light-induced jumping crystals by kinematic analysis
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