Last Decade of Research on Activated Carbons as Catalytic Support

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Last Decade of Research on Activated Carbons as Catalytic Support inChemical ProcessesV. Calvino-Casildaa; A. J. López-Peinadob; C. J. Durán-Vallec; R. M. Martín-Arandab

a Catalytic Spectroscopy Laboratory, Instituto de Catálisis y Petroleoquímica (CSIC), Madrid, Spain b

Dpto. de Química Inorgánica y Química Técnica, Facultad de Ciencias, Universidad Nacional deEducación a Distancia (UNED), Madrid, Spain c Dpto. de Química Orgánica e Inorgánica, Facultad deCiencias, Universidad de Extremadura, Badajoz, Spain

Online publication date: 11 August 2010

To cite this Article Calvino-Casilda, V. , López-Peinado, A. J. , Durán-Valle, C. J. and Martín-Aranda, R. M.(2010) 'LastDecade of Research on Activated Carbons as Catalytic Support in Chemical Processes', Catalysis Reviews, 52: 3, 325 —380To link to this Article: DOI: 10.1080/01614940.2010.498748URL: http://dx.doi.org/10.1080/01614940.2010.498748

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Last Decade of Research onActivated Carbons asCatalytic Support in ChemicalProcesses

V. Calvino-Casilda1, A.J. López-Peinado2, C.J. Durán-Valle3,and R.M. Martín-Aranda2

1Catalytic Spectroscopy Laboratory, Instituto de Catálisis y Petroleoquímica (CSIC),Madrid, Spain2Dpto. de Química Inorgánica y Química Técnica, Facultad de Ciencias, UniversidadNacional de Educación a Distancia (UNED), Madrid, Spain3Dpto. de Química Orgánica e Inorgánica, Facultad de Ciencias, Universidad deExtremadura, Badajoz, Spain

This review is devoted to the application and knowledge developed in the past 10 years inthe area of chemical processes catalyzed by activated carbon supported catalysts.Activated carbons are well known for their catalytic properties and for being used assupport in heterogeneous catalysis. The supported catalysts have been successfully usedin the chemical industries for long time. In the last decade, carbon supported catalystshave opened the door for new chemical catalytic processes based on their intrinsicfeatures. However, fundamental understanding of molecular structure-reactivityrelationship of these carbon materials remains unexplored. Futures advances in allareas may be possible through combined experimental and theoretical approaches.

Keywords Activated carbons, Heterogeneous catalysis, Supported catalysis, Acidreactions, Basic reactions, C-C bond formation, Oxidation reactions, Reduction reactions.

INTRODUCTION

Only a small number of chemical processes are still conducted without theaddition of a catalyst (1). Catalysis is of crucial importance for today’s chemicalindustry and particularly nowadays in the field of fine chemicals.

Received November 20, 2009; accepted May 24, 2010Address correspondence to V. Calvino-Casilda, Catalytic Spectroscopy Laboratory,Instituto de Catálisis y Petroleoquímica (CSIC), Marie Curie, 2. E-28049-Madrid,Spain. E-mail: [email protected]

Catalysis Reviews: Science and Engineering, 52:325–380, 2010

Copyright © Taylor & Francis Group, LLC

ISSN: 0161-4940 print / 1520-5703 online

DOI: 10.1080/01614940.2010.498748

325

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Supported catalysts are of special interest. They allow the fine dispersionand stabilisation of small metallic particles providing access to a much largernumber of catalytically active atoms. In particular, it has been observed thatactivated carbon exhibit optimum properties and performance, stability in bothacidic and basic media that let them to be used as catalyst support in multitudeof different applications in the chemical industry.

At the beginning of last decade, Rodríguez-Reinoso remarked the use ofcarbon as catalyst support for different industrial processes (2). In the past,the lack of fundamental understanding of many aspects of the use of carbon incatalysis caused a limited employ of carbon as catalyst and still more as catalystssupport. But the continuous studies on understanding of all aspects of thephysical and chemical characteristics of carbon material, especially activatedcarbon, AC (surface area and porosity) and even more, the possibility of control-ling the surface chemistry of suchmaterials is the origin of important researchescarried out in industrial chemistry during the last decade. As a result, this paperreports the evolution in the last decade of the use of activated carbon as catalystsupport employed in a variety of current industrial processes.

In heterogeneous catalysis, carbon materials have been used for long timebecause they can be used directly as catalysts, and moreover, they can satisfymost of the properties desired for a suitable support. It has been shown thatalthough the surface area and the shape of carbon porosity may be very impor-tant in the preparation and properties of the corresponding catalysts, the role ofcarbon surface chemistry is also extremely important. The most common het-eroatoms present on carbon surface are hydrogen, oxygen, nitrogen, sulphur andphosphorus. These atoms are arranged in the forms of functional groups, suchacidic ones as carboxylic, lactonic, phenoclic, or basic groups, such as pyranesand chromene. The number and strenght of these groups influence the apparentacidity or basicity of the carbon surface. Moreover, a few percent of inorganicmatter from the organic precursor (e.g. coal or wood) could be present on carbonsand this fact is considered important for their perfomance, especially when theyare used as catalyst supports. However, although the catalytic effect is mainlyheaded by the chemical properties of the active phase, the dispersion and thelocal distribution of the active phase across the activated carbon support as wellas the interaction active phase-support are significantly important. These arejust the aspects of carbon supports that make them so attractive for heteroge-neous catalysis. These parameters can be modified to satisfy any specificrequirement during catalyst preparation making the surface not only physicallybut also chemically accessible to the precursor and diminishing the deactivationby sinterization. It seems obviously that the future is promising once it is under-stood that not only the surface area and porosity of carbon materials are the keyfor their uses, and that both physical and chemical surface properties of carbonsupport have to be taken into account when designing a solid catalyst. Due to theconstant interest in heterogeneous catalysis of using activated carbon as

326 V. Calvino-Casilda et al.


catalyst support in search of suitable catalysts for certain chemical processes,this reviewwill bemainly concernedwith the use of carbon as catalyst support tohighlight the great contribution of this material during the last decade.

CATALYTIC OXIDATIONS (TABLE 1)

The identification of new catalyzed reactions is of key importance to the chemicalindustry and, in particular in the production of fine chemicals. Selective hetero-geneous oxidation catalysis is crucial to the well being of society, since it pro-duces about 25% of the most important industrial organic chemicals andintermediates used in the manufacture of industrial products and consumergoods. Most of the reactions for the synthesis of fine chemicals and pharmaceu-ticals involve one or more steps of oxidation of organic functional groups. In thelast decade, industrial researchers have expended great efforts tomake selectiveoxidation processes and their catalysts even more efficient and environmentallyfriendlier. Among these catalysts activated carbon supported materials havebeen briefly employed in different oxidation reactions.

Volatile organic compounds (VOCs) and chlorinated volatile organic com-pounds are environmental pollutants and are the subject of stringent regula-tions. Different methodologies have been considered to diminish the emissions.Activated carbons are finding increasing applications as catalyst supports in thetreatment of gaseous effluents to destroy the VOCs emissions, where advantageis taken of the enhanced retention of organic pollutants in the pore system of thecarbon. Platinum supported on activated carbon has been used as catalyst andother less expensive alternatives have been also considered; an increasing inter-est is associated with activated carbons impregnated with transition metaloxides (3–5). Recently Lu et al. have tested transition metals (Cu, Co, Fe andNi) supported on activated carbon in the simultaneous removal of VOC and NOin combustion flue gas (6) and Wu et al. have prepared Pt/AC catalysts forbenzene, toluene and xylene (BTX) deep oxidation at low-temperature on thecatalytic destruction of VOC (7). Suh et al. have investigated a Co/AC catalystactivated with ozone for removing chemically offensive odors such as benzene,toluene, mercaptans, and sulfides (8). Cherkezova-Zheleva et al. have alsoinvestigated the total oxidation of benzene over Fe-Pd/AC and Fe-Pt/AC cata-lysts (9). Since basicity is an important factor for efficient removal of methylmercaptan on activated carbons, the performance of materials can be enhancedby impregnation of activated carbon with basic compounds such as NaOH,Na2CO3, KOH and K2CO3 (10,11). They are able to improve the capacity ofcarbons for methyl mercaptan removal by a factor of two (10). Other possibilityto improve this capacity is to promote redox surface reaction by surface impreg-nation with other compounds such as Fe2O3, KI and KIO3 increasing the capa-city by a factor 3–5 (10,12 ).

Last Decade of Research on Activated Carbons 327


Table

1:Main

oxidatio

nreactio

nscatalyse

dbyactiv

atedcarbonsu

pportedmetal,non-m

etala

ndtheircompoundcatalystsin

thelast

decade.

Cata

lytic

oxidatio

ns

Precious

meta

lsAlkali

meta

ls

Alkali

earths

meta

lsTransitio

nmeta

lsOthers

PdPt

Ru

Rh

Ag

Au

Na

KCa

VCr

Mn

FeCo

NiMo

WRe

SnBi

Cu

ZnP

Ce

-Oxidatio

nofh

ydrocarbons

-Alkanes/

cyc

loalkanes

!!

!!

!!

-Methanereform

atio

n!

!!

-Alkenes/

cyc

loalkenes

!!

!!

-Aromatic

s!

!!

!!

!!

-Oxidatio

nofh

alocarbons

!!

!!

!!

-Oxidatio

nofa

ldehyd

es

!!

!!

!-O

xidatio

nofc

arboxylic

acids

!-O

xidatio

nofa

lcohols

-Alip

hatic

s!

!!

!!

!!

!!

!!

!!

-Phenols

!!

!!

!!

!!

!-C

arbohyd

rates

!!

!!

!-O

xidatio

nofc

yclic

ketones

!-O

xidatio

nofd

yewastewater

!!

!-E

thers

andesthers

!-C

Ooxidatio

n!

!!

!!

!!

!!

!!

-NO

oxidatio

n!

!!

!-S

O2oxidatio

n!

!!

!!

-H2Sandsu

lphidesoxidatio

n!

!!

!!

!!

!!

-H2oxidatio

n!

!-D

esu

lphurisatio

nreactio

n!

!!

-Ammonia

!!

!!

!!

!!

328


Some authors have carried out low temperature hydroxylation of aromaticcompounds by hydrogen peroxide over Fe/AC and Pd/AC catalysts (13).Alkylated benzenes are an important class of hydrocarbons because they com-prise a significant portion of gasoline and diesel fuels. Alvarez-Merino et al. havereported the catalytic combustion of toluene over tungsten oxide supported onactivated carbon catalysts for removing toluene from dilute streams (14).Halocarbons represent the most abundant family of industrial toxic compoundsas it has been recently recognized from different polluting sources like herbi-cides, pesticides, chemical and solvent manufacturing, the paint industry, andthe dechlorination of drinking water. The application of innovative advancedoxidation technologies (AOTs) like the oxidation of 4-chlorophenol (an importanttoxic pollutant) with hydrogen peroxide in aqueous solution using Fe/AC cata-lysts is of interest to abate efficiently and also reduce the treatment cost throughdestructive techniques mineralizing the halocarbon (15). Wang et al. have alsocarried out the oxidation of 4-chlorophenol over Pd/AC catalysts used for gas-diffusion electrode (16). Qin et al. have carried out the catalytic wet oxidation ofaqueous p-chlorophenol over supported noble metal activated carbon catalystsand Sun et al. have examined the chemical reactivity of AC-supported iron as acatalyst to decompose polychlorinated biphenyls (PCBs) under air or N2 atmo-sphere (17,18). Several activated carbon-supported chromium oxide catalystswere effective for complete chlorinated volatile organic compounds (CVOCs)oxidation such as methylene chloride and perchloroethylene (19,20).

The catalytic wet-air oxidation (CWAO) process is effective in convertingorganic pollutants such as phenolic pollutants to innocuous carbon dioxidecurrently found in industrial wastewaters. Pt on TiO2-grafted activated carbon,CuO/AC and Fe/AC are some of the catalysts employed for the wet air oxidation(21–23). Noble metal catalysts on activated carbon (Pt/AC and Ru/AC) and base-metal catalysts (Cu/AC, CoMo/AC, Mo/AC and Mn/AC) were developed andexamined for the simultaneous removal of organic pollutants and ammoniafrom wastewater using the wet air oxidation (WAO) process in the liquid phase(24,25). Bandosz et al. also reported the removal of ammonia from air on acti-vated carbons modified with aluminium-zirconium polycations and micro/meso-porous activated carbons modified with molybdenum and tungsten oxides byproviding new Brönsted acidic centers that form strong interactions with theadsorbed gas in its protonated form (26,27). Zazo et al. and Quintanilla et al.have studied the catalytic wet peroxide oxidation of phenol with a Fe/AC catalystin aqueous solution (28,29). Lei et al. have reported the behaviour of Cu-Ce/ACcatalyst-sorbent in the dry oxidation of phenol showing high phenol adsorptioncapacities and high phenol oxidation activities (30).Wen et al. have prepared Co-Ce/AC as a new catalyst for catalytic wet air oxidation of phenol (31) and Kimet al. have studied the effects of inorganic cocatalysts (Ce, Co, Mn and Cu) andinitial states of Pd on the oxidative carbonylation of phenols over heterogeneousPd/AC catalysts following the well-known “redox” or “multi-step electron



transfer mechanism” between a Pd complex and organic/inorganic cocatalysts(32). Due to their observation in previous works that the metallic character ofpalladium was significantly enhanced after the reaction, they investigated theeffects of the initial state of Pd on the catalyst activity and product selectivitiesfor a fixed amount of Pd added with a fixed amount of cocatalys concluding thatthe catalytic performance was independent of the different initial states of Pd inPd/AC catalysts. Recently Bo et al. have carried out the removal of phenolicpollutant in aqueous solution by microwave-assisted catalytic oxidation usingPt/AC catalysts showing better results than in the catalytic wet air oxidationpreviously reported (33).

Nowadays gold supported on activated carbon is the preferred catalyst forthe oxidation of the alcoholic and the aldehydic groups and one of the bestpreparation methods of those catalysts is the immobilisation of colloidalparticles.

A large number of products can be formed from glycerol oxidation being one ofthe key problems the selectivity by which the individual products can be formed(Fig. 1). Nevertheless, if the products could be formed in high selectivity, they arepotentially valuable as chemical intermediates in the fine chemicals industry.Prati et al. have presented Au/AC and Au-Pd/AC as selective catalysts for theoxidation of alcohols such as glycerol, including diols, under relatively mild condi-tions (34–37). More recently, they have established that by using bimetallic cata-lysts (Au-Pd/AC and Au-Pt/AC) a strong synergistic effect was shown and highactivity and a prolonged catalyst life were also found (38,39). Demirel-Gulen et al.

Dihydroxyacetone Mesoxalic acidHydroxypyruvic acid

Tartronic acid

Glyoxilic acid

Glyceric acid

Glycerol

Glyceraldehyde

Glycolic acid

Figure 1: General reaction pathways for glycerol oxidation.



and Carrettin et al. have also investigated the glycerol oxidation reaction (40).Glycerol can be oxidised to glyceric acid with 100% selectivity at high conversionusing Au/AC as catalyst (41). Porta et al. have used Au/AC catalysts for theselective liquid phase oxidation of ethylene glycol to glycolate (42).

Pratti et al. have oxidized in liquid-phase carbohydrates and aldehydes tothe corresponding carboxylic acids with O2 under mild conditions using Au/ACcatalysts without loss of activity on recycling (43). Deffernez et al., have studiedthe oxidation of glyoxal into glyoxalic acid over Pd/C catalysts (44). Comotti et al.have also oxidized in liquid-phase carbohydrates and alcohols using gold acti-vated carbon catalysts (45). Bian et al. have reported the oxidation of glucose toobtain sodium gluconate by Bi promoted Pd/AC catalysts (46).

Hayashi et al. and Korovchenko et al. have investigated the oxidation ofalcohols to the corresponding aldehydes and carboxylic acids with air in thepresence of catalytic amount of transition metals such as copper, ruthenium,palladium, and platinum compounds on activated carbon (47,48). Paneva et al.have studied the catalytic behavior of Fe and/or Ru supported on activatedcarbon in methanol decomposition to CO and methane (49). This group havealso studied the catalytic behaviour of nanosized iron and mixed iron-cobaltoxides supported on activated carbon materials in methanol decomposition toH2, CO, and CH4 (50). CuO/MnO/AC, Re-Cu/AC and Re-Mn/AC have beenstudied in the reaction of methanol decomposition to H2 and CO by Tsoncheva´s group (51–53) and Pt/AC and Pd/AC catalysts by Ubago-Pérez et al. (54).

Diethyl carbonate (DEC) is a promising oxygenated organic additive forgasoline and diesel fuel to reduce pollutant emissions. Many research groupshave readily prepared diethyl carbonate from the oxidative carbonylation ofethanol in gas phase with high selectivity using Wacker-type catalysts, CuCl2/PdCl2 and CuCl2/PdCl2/KOH supported on activated carbon (55–58). Ma et al.have studied the catalytic vapor phase synthesis of diethyl carbonate from COand ethyl nitrite over catalysts prepared from PdCl2-CuCl2 and PdCl2-CuCl2-CeCl3 supported on activated carbon (59).

Dimethyl carbonate (DMC) is a uniquemolecule having a versatile reactivitybeing very useful for environmentally benign reactions. Some research groupshave prepared supported Wacker-type catalysts by impregnation of the acti-vated carbon support with KOAc promoter and CuCl2 or PdCl2/CuCl2 showinga higher performance in the gas-phase oxidative carbonylation of methanol forthe dimethyl carbonate synthesis (DMC) (Fig. 2) (60–62). Some authors havestudied the role of copper chloride (63,64) and copper chloride hydroxides

2CH3OH + CO + 1/2 O2 (CH3O)2 CO + H2O

Figure 2: Oxidative carbonylation of methanol process for the dimethyl carbonate synthesis(DMC).



deposited on the activated carbon in the oxidative carbonylation of methanol fordimethyl carbonate (DMC) synthesis using vapour phase flow reactor system(65–67). More recently, Cui et al. have reported the dimethyl carbonate synth-esis over catalysts prepared loading KI and K2CO3 on activated carbon (68).

Zoeller et al., have used gold activated carbon catalysts in the vapor phasecarbonylation of lower aliphatic alcohols, ethers, esters, and ester-alcohols mix-tures, and desirably, methanol, to produce carboxylic acid, esters and mixturesthereof. The solid supported catalyst includes an effective amount of gold asso-ciated with activated carbon in the presence of a halide promoter (69).

Pt-SnOx/AC and Pt-CeOx catalysts supported on un-oxidized and oxidizedactivated carbon (AC) have been employed in the selective CO oxidation inH2-richgas streams containing CO2 and H2O simulating the reformate coming from fuelprocessors (70). Non-noble metal catalysts have also been employed in this reac-tion such as Ni, Co and Co-Ni/AC (71). Polymetals (Cu, Cr and Ag) supported onactivated carbonwere used in the catalytic oxidation of carbonmonoxide in a fixedbed reactor (72). Wacker-type catalysts as for example Pd-Cu/AC catalysts weretested in the catalytic oxidation and chemisorption of CO for smoke applications(73). Pt/AC and Pt-Sn/AC catalysts have also been employed in CO oxidation (74).

Presently, most of the industrial hydrogen production is based on steammethane reforming (SMR) process, which is a source of significant CO2 emis-sions into the atmosphere. New routes to hydrogen production from natural gas(or methane) with drastically reduced CO2 emissions have been investigated.The direct decomposition of methane shows a promising alternative to thetraditional hydrogen production methods such as steam methane reforming(SMR) and partial oxidation of methane (POM) because there is no furtherbyproduct except carbon. Activated carbon has been suggested as a good supportfor metal catalyst for COx-free hydrogen production by methane decompositionbecause AC is relatively stable, non-toxic as itself, easily obtained from variousraw materials and the textural properties and surface structure can be easilycontrolled in the manufacture process, which makes it more favourable to be acatalyst support. Muradov et al. have reported the oxygen-assisted decomposi-tion of methane over AC-supported iron catalysts experimenting over widerange of temperatures andO2/CH4 ratios (75). An advantage of producing syngasby this route instead of processes like steam reforming or partial oxidation is thelow H2/CO ratio obtained, which is of particular interest for the synthesis ofvaluable oxygenated chemicals, such as alcohols or aldehydes. Okumura et al.have prepared supported gold catalysts on activated carbon for low-temperatureoxidation of CO and H2 (76) and some other authors have investigated the COselective oxidation on Au/AC and Ag/AC catalysts in hydrogen-rich gas to elim-inate CO impurities when hydrogen is produced via the reforming reaction to beused as a source of energy for stationary power plants, moving vehicles and fuelcell applications (77,78).



The preparation of metal supported activated carbon with Ni can catalyzethe decomposition of methane and ethylene forming carbon nanofibers (CNFs)under relatively mild conditions (79,80).

But the reforming ofmethanewith carbon dioxide to synthesis gas has recentlyattracted renewed interest. Numerous supported catalysts have been proposed formethane reforming. In 1998 Wang et al. proposed Ni/AC catalyst to develop thisreaction and now Diaz et al. have reached representative methane conversions atmild experimental conditions usingNi-Ca/AC catalystswhereCa plays a cosupportrole inhibiting the deactivation of catalyst during long periods of reaction (81,82).

Valente et al. have reported the oxidation of cycloalkanes such as pinane usingtransition metal, cupper and cobalt acetylacetonate complexes inmobilized onactivated carbon at room temperature and atmospheric pressure. This group andalso Langhendries et al. have reported the selective oxidation of cycloalkanes usingactivated carbon supported iron-phtalocyanine catalysts (83–85).

Kishi et al. have carried out the oxidation of cycloalkenes such as cyclopenteneunder oxygen atmosphere using a Wacker type catalysts, Pd(OAc)2 supported onactivated carbon combined with molybdovanadophosphate (NPMoV) (86). Theoxidation of terpenes such as limonene over activated carbon anchored transitionmetal Schiff base complexes catalysts is reported by Oliveira et al. (87).

Some other authors have studied the catalytic oxidation of sulphur contain-ing compounds; Hui-Hsin Tseng et al. have investigated the catalytic oxidationof SO2 from incineration flue gas over Cu/AC and bimetallic Cu-Ce/AC catalystsand they have also carried out the simultaneous catalytic oxidation of sulfurdioxide/hydrogen chloride from incineration flue gas over activated carbon-supported copper, iron or vanadium oxide catalysts and this group have alsocarried out (88,89).

The Pd/AC and Pt/AC catalysts were found to be oxidation catalysts at hightemperature for hydrogen sulphide oxidation and methane oxidation (90). Dalaiet al. have also reported activated carbon supported catalysts impregnated withammonium iodide, potassium iodide and potassium carbonate for hydrogensulphide oxidation (91). Radkevich et al. have studied the influence of surfacefunctionalization of activated carbon on palladium dispersion in the preparationof Pd/AC catalyst and the catalytic activity in hydrogen oxidation (92).

The Zn/AC and CuO/AC catalysts were tested in desulphurisation reaction(DeSO2) (93). Wang et al. have carried out the electrochemical desulphurisationreaction over CeO2/AC catalysts (94). Xiao et al. have reported the catalyticoxidation of hydrogen sulphide over activated carbon impregnated with Na2CO3

(95) and Ma et al. the catalytic oxidation reaction for purifying H2S and PH3

contained in tail gas over activated carbon impregnated with Na2CO3 and alsowith HCl (96). Activated carbons impregnated with caustic materials (NaOH orKOH) have been used for removal H2S in sewage treatment plants. The residualH2S quickly reacts with the strong base and is immobilized (97–99). However theshortcoming in the applications of caustic impregnated carbon is the fact that



impregnation decreases the ignition temperature of the carbon and poses a risk ofself-ignition. In addition, the activity of caustic carbons in H2S oxidation is wornout when caustic is consumed and the carbon pores are blocked by sulfur andsodium or potassium salts.

Ramirez et al. have reported the degradation and mineralization of the non-biodegradable azo dye Orange II making use of a Fenton-like oxidation processover a Fe/AC catalyst (100). Zhang et al. have preparedCuFe2O4/AC catalysts forthe removal of acid Orange II which combined the magnetic and the excellentcatalytic properties of powdered CuFe2O4 (101). Sun et al. have studied thecatalytic performance of activated carbon supported tungsten carbide for hydra-zine decomposition (102).

CATALYTIC REDUCTIONS (TABLE 2)

Hydroprocessing is a group of technologies where catalytic reactions take placein presence of hydrogen at elevated pressure to fulfil some or all of the followingmajor objectives:

1. Hydrogenation. Increase H/C, saturation of unsaturated hydrocarbon com-pounds (e.g. olefins and aromatics).

(a) Stabilizing distillate fuels like gasoline, jet fuel by preventing sedimentformation.

(b) Upgrading (decreasing boiling point range) of residue.

2. Hydrocracking. Cracking of heavier hydrocarbon molecules to lighter onesfor production of desired fuels and lubes.

3. Hydrotreating. Removal of hetero-atoms and impurities from hydrocarbonstreams. (e.g. sulfur, hydrodesulphurization (HDS); nitrogen, hydrodenitro-genation (HDN); metals such as chlrorine (hydrodechlorination, HDC); con-densed ring aromatics etc.).

Catalysts are commonly used for the hydrogenation of alkenes, alkynes,aromatics, aldehydes, esters, carboxylic acids, nitro groups, nitriles, and imines.The selective hydrogenation of carbon-carbon double and triple bonds is one ofthe fundamental reactions for the synthesis and manufacture of fine and indus-trial chemicals. A wealth of processes and applications in the pharmaceutical,agrochemical and petrochemical industries is based on catalytic hydrogenationof unsaturated hydrocarbons by heterogeneous catalysts. The classical hetero-geneous catalysts for carbon-carbon multiple bond hydrogenation involves sup-ported precious metals, activated base metal catalysts and Ni supported onoxides all being able to activate hydrogen under mild reaction conditions.



Table

2:Main

reductio

nreactio

nscatalyse

dbyactiv

atedcarbonsu

pportedmetal,non-m

etala


thelast

decade.

Cata

lytic

reductio

ns

Precious

meta

lsAlkali

meta

ls

Alkali

earths

meta

lsTransitio

nmeta

lsOthers

PdPt

IrRu

Rh

Ag

Au

LiNa

KRb

Cs

Mg

BaV

Cr

Mn

FeCo

NiCu

ZnMo

WRe

AlSn

PbP

Ce

Ge

-Hyd

rogenatio

nofa

lkenes

/cyc

loalkenes

!!

!!

!!

-Hyd

rogenatio

nofa

lkyn

es!

-Hyd

rogenatio

nofa

romatic

rings

!!

!!

-Hyd

rogenatio

nofn

itro

compounds

!!

!

-Hyd

rogenatio

nofa

ldehyd

es

!!

!!

!!

!!

!!

!

-Hyd

rogenatio

nofk

etones

!!

!!

-Hyd

rogenatio

nofc

arboxylic

acid

deriv

ativ

es

!!

!!

-Hyd

rogenatio

nofe

sters

!!

!!

!

-Hyd

rogenatio

nofa

zides

!

-Hyd

rogenatio

nofterpenes

!!

-Hyd

rogenatio

nof

carbohyd

rates

!

-Hyd

rodesu

lphurisatio

n!

!!

!!

!!

!!

-Hyd

rodenitrogenatio

n!

!!

!!

!!

-Hyd

rodehalogenatio

n!

!!

!!

!!

!!

!!

!!

!!

-Hyd

rogenolysis

!!

!!

!!

!-C

O2hyd

rogenatio

n!

!-C

O2reductio

n!

!-C

Ohyd

rogenatio

n!

!!

-Reductiv

eaminatio

n!

-NO

xreductio

n!

!!

!!

!!

!!

!!

!!

-Methanol

decompositio

n!

!!

!!

!!

!

335


However, these materials have commenced to be repleaced by activated carbonsduring the last decades.

Matos et al., have reported Ni/AC and Ni-Mo/AC catalysts for the hydro-genation of simple insaturated hydrocarbons such as ethylene (103–105).Precious metals supported-activated carbon catalysts such as Pd, Pt, Rh andIr, have been tested on hydrogenation of alkenes and cycloalkenes (106–112).Kirm et al. have prepared Pd and Pt/AC catalysts for gas-phase hydrogenation ofstyrene oxide to produce 2-phenylethanol, a compound with bacteriostatic andantifungic properties, used in formulation of cosmetics and with importantapplications in the manufacture of chemical compounds (113,114). Domínguez-Domínguez et al. have carried out a reaction of great industrial interest such asthe semihydrogenation of phenylacetylene in liquid phase over Pd/AC catalysts(115). Recently Mori et al. have developed a diphenyl sulphide inmobilized onPd/AC system for chemoselective hydrogenation of alkenes, acetylenes, azides,and nitro groups in presence of aromatic ketones, halides, benzyl esters, and N-benzyloxycarbonyl groups (116).

In general, the aromatic ring hydrogenation requiresmore severe conditionsthan the hydrogenation of other functional groups and highly homogeneouscatalytic systems have disadvantages concerning stability, productivity, andmanufacture. Pt-Sn and Pt/AC catalysts have been tested on benzene hydroge-nation to cyclohexane (117,118), Ru/Ac catalysts have been tested on benzeneand toluene hydrogenation (119) and Pd/AC catalysts have been developed forthe hydrogenation of phenol to cyclohexanols or cyclohexanone, in aqueousphase and in vapour phase to explore a possible way for the treatment of phenolicwastewaters and to obtain intermediates for the fragance and pharmaceuticalindustry (Fig. 3) (120–123). Hiyoshi et al. have reported the hydrogenation ofnaphthalene in supercritical carbon dioxide solvent over Rh/AC catalysts (124).

Esters, carboxylic acids, and ketones can be reduced to their respective alco-hols using precious metals (Pt, Pd, Ru, and Rh) and nickel supported-activatedcarbon catalysts (125–130). Wolfson et al. have reported the enantioselectivehydrogenation of a β-ketoesters such as methyl acetoacetate to β-hydroxyestersover Ni/AC catalysts (131). These compounds are useful building blocks for thesynthesis of biologically active compounds and natural products. Perez-Cadenas

OH O OH

H2 H2

H2

Figure 3: Reaction paths in phenol hydrogenation over activated carbon supported catalysts.



et al. have reported the hydrogenation of fatty acid methyl esters (vegetable oils)on palladium catalysts supported on carbon-coated monoliths (132). Gulyukinaet al., have carried out the hydrogenation of α-oxophosphonates with molecularhydrogen over Pd/AC catalysts for the synthesis of α-hydroxyphosphonates (133).

The hydrogenation of α,β-unsaturated aromatic aldehydes is accompaniedby the formation of several by-products. The hydrogenation of cinnamaldehydehas been attracting increasing interest due to the importance of the derivativesin the fine chemicals industry. The selectivity to the desired products is still animportant issue in the case of the industrial hydrogenation of cinnamaldehydetowards the clean production of the desired intermediates. Some authors haveinvestigated the reaction using precious metals supported-activated carboncatalysts such as Pd, Pt, and Ru (134–136). Others authors have studied thehydrogenation of α,β-unsaturated aldehydes such as crotonaldehyde and citralover activated carbon-supported metal catalysts (Pt-Zn/AC Coloma et al. (137);MoC/AC, Guerrero et al. (138); Cu/AC, Dandekar et al. (139); Ru and Ru-Fe/AC,Bachiller-Baeza et al. (140); Pt/AC, Thomson et al. and Silvestre et al. (141,142);PtSn/AC and PtGe/AC, Vilella et al. (143,144), J.C. Serrano-Ruiz et al. (145), andmolybdophosphoric acid-V2O5/AC) (146).

The hydrogenation of nitro compounds to the corresponding amines is a veryimportant reaction, as these chemicals are used as basic raw materials forurethanes, rubber chemicals, dyes, and pharmaceuticals. Jaganathan et al.have reported Pd/AC catalysts for the catalytic hydrogenation of p-nitrocumeneto p-cumidine in a slurry reactor (147). Activated carbon supported platinumcatalysts have been employed in the hidrogenation of ortho-nitrochlorobenzeneto 2,20-Dichloro-hydrazobenzene and in the hydrogenation of nitrobenzene(148,149). On the other hand, activated carbon supported nickel catalyst havebeen used in the hydrogenation of p-chloronitrobenzene to p-chloroaniline (150).It has also reported that Pt/AC catalysts can convert primary amines intosecondary amines in good yield, via retro-reductive and reductive aminationupon microwave irradiation in water (151).

Mahmudov et al. have reported the hydrogenation of perchlorate over Co-Pt/AC, Ni-Pt/AC, W-Pt/AC and Pt/AC catalysts (152).

Heinen et al. have reported the hydrogenation of sugars such as fructose onRu/AC catalysts and De Miguel et al. have studied the effect of the activatedcarbon support in Pt and PtSn catalysts used for selective hydrogenation ofterpenes such as carvone (Fig. 4) (153–156).

Sakata et al. have studied the catalytic activity in CO2 hydrogenation tomethanol of activated carbon-supported Cu-ZnO catalysts (157) and Zhongrui Liet al. have reported the mixed alcohol synthesis over Mo-K- and Co-Mo-K/ACcatalysts via CO hydrogenation (158,159). The reduction of carbon dioxide withwater has been investigated for the direct synthesis of methane over Raney Fe-Ru/AC catalysts by Kudo et al. (160).



A closely related reaction to hydrogenation is hydrogenolysiswhere amoleculeof hydrogen is added over a carbon-carbon single bond, effectively causing a “lysis”of the bond.Ru/AC catalystswere tested on the hydrogenolysis of n-hexane andPt-,Pd- and Ru/AC catalysts in the catalytic transfer hydrogenolysis of 2-phenyl-2-propanol over Pd/AC catalysts.Markus et al. have carried out thehydrogenolysis ofa wood extractive, the natural ocurring lignan hydroxymatairesinol, to an antic-arcinogenic and antioxidative compound using Pd/AC catalysts (161–163).

Chlorofluorocarbons (CFCs) have had a lasting effect on the environment.They are a major source of stratospheric chlorine, which is responsible for thedepletion of the ozone layer. Catalytic hydrodechlorination (HDC) has emergedas a promising non-destructive technology not only for the safe conversion ofchlorinated waste, but also producing value-added products. Noble metals havemainly been used as catalysts in the hydrodechlorination reaction of CFCs. Inparticular, supported palladium is the most widely used catalyst for this reac-tion. Catalysts employed for HDC reaction are often susceptible for deactivation,due to strong adsorption of HCl produced as a by-product. In this context, thedevelopment of a poison-resistant catalyst has gained significant importance inrecent years. The hydrodechlorination activity depends on the nature of activesites, which are influenced by several factors such as the method of preparation,themean particle size, and the nature of precursor salt used in the preparation ofcatalysts. The selective hydrogenolysis of CFCs such as CCl2F2 (CFC-12) intoCH2F2 (HFC-32) and CFC-115 into HFC-15 over Pd/AC catalysts have beenstudied by many authors (108,164–173). There are also many studies usingother noble metal supported-activated carbon catalysts. Pt, Pd, Rh, Ru, Ir, andRe/AC catalysts, and bynary metal mixtures (Pt-Cu, Pt-Ag, Pt-Fe, and Pt-Co)supported-activated carbon catalysts have been used in the hydrodechlorinationof CFC-12 and CFC-13 (175–179).

There are also authors who have investigated non-noble metals supported-activated carbon catalysts such as Ni/AC. These catalysts have shown similarcatalytic behaviour to the noble catalysts, but only a few studies in the lastdecade have dealt with the hydrogenolysis reaction of chlorofluorocarbons.Morato et al. have prepared activated-carbon-supported nickel (Ni/AC), nickel-potassium oxide (NiK/AC), nickel-copper (NiCu/AC) and nickel-aluminium oxide(NiAl/AC) catalysts for the hydrogenolysis of halogenated chlorofluorocarbons(CFC-12) (180). Calvo et al. have carried out the hydrodechlorination of Alachlor

CHO OO

+

Figure 4: Reaction scheme of the catalyzed carvone hydrogenation.



in water using Pd, Ni and Cu/AC catalysts (181) and Keane et al. have studiedthe hydrodechlorination of chlorobenzene over Ni/AC catalysts (182).

Water pollution is a major concern for the pulp and paper industry due to thelarge quantities of effluents generated. The effluents from pulp bleaching areresponsible for most of the colour, organic matter and toxicity of the water dis-chargesof this industry.Catalytichydrodechlorination isproposedasan interestingalternative/complement for the elimination of chlorinated organics from bleachingeffluents. Calvo et al. have employedPd/AC catalysts for the hydrodechlorination ofchlorophenols with the aim of reducing the toxicity of a type of wastewaters(183–185). Santoro et al. (186) and Keane et al. (187), have carried out the hydro-dechlorination (HDC) of chlorobenzene over Ni and Fe/AC catalysts and otherauthors over Ni, Fe, W, Ni-Mo, Pt and Pd supported-activated carbon catalysts(187–191). In the study of catalytic reduction of contaminated waters, containingnitrates Barrabes et al. have employed Pt-Cu/AC and Pd-Cu/AC catalysts (192).

The Pt/AC catalysts have been prepared for the hydrodechlorination ofaliphatic organochlorinated compounds that are released into the environmentin the greatest amounts (dichloromethane, chloroform, carbon tetrachloride,1,1,1-trichlorethane, trichloroethylene and tetrachloroethylene) (193,194).Early et al. have carried out the hydrogen-assisted 1,2,3-trichloropropanedechlorination on Pt-Sn/AC catalysts (195).

Dhandapani et al. have used the reactivity of molybdenum carbide sup-ported on activated carbon with phosphorous additive as catalysts for hydro-processing reactions such as hydrogenation, hydrodesulfurization (HDS) andhydrodenitrogenation (HDN) using model liquid compounds (196). Othersupported-activated carbon containing metal, binary metal mixtures such asCoMo/AC, NiMo(W) and PNiMo(W)/AC, Fe-Mo/AC, Re/AC, Ni-Re/AC, Ni-Mo/ACand sulfided metals such as Ni-Mo/AC have been employed as catalysts inhydrotreatment processes by other authors (197–204). More recently, Pintoet al. have prepared vanadium nanoparticles supported on activated carboncatalysts for tiophene hydrodesulphurization (206) and Park et al. the synthesisof ZnO/AC catalyst for the effective removal of a very low concentration of sulfurcompounds contained in a gasified fuel gas (207).

Xing etal. have employedV2O5-CoO/ACcatalysts for flue gasSO2 removal andelemental sulfur production (208) and Guo et al. have reported V2O5/AC catalystsin simultaneous sulfur dioxide and nitric oxide removal from flue gas (209).

Selective catalytic reduction (SCR) of NOx is a tecnhology to remove nitrogenoxides, the most abundant and polluting component in exhaust gases, through achemical reactionbetween theexhaust gases, a reductantadditive, andacatalyst.Agaseous or liquid reductant (most commonly ammonia or urea) is added to a streamof flue or exhaust gas and is absorbed ontoa catalyst.The reductant reactswithNOx

in the exhaust gas to form harmless H2O and N2. Special catalytic converters arerequired tomakeanSCRsystemwork, the current options being avanadium-basedcatalyst, or a catalyst with zeolites in the washcoat.



Previous studies on supported-activated carbon catalysts exhibit low catalyticactivity for NOx reduction. Hence, an enhancement of the activity for NOx reduc-tion was required through a proper modification of the carbon characteristics andthe use of active phase. For that reason in the last decade many authors haveworked on improving their catalytic activity by optimisation of char preparation;increasing surface area and porosity, loading of some metals and its oxides, suchas Na, K (210–212) ; Pt (213–216); Fe, Co, Ce, Cu, La (217–222); Ni (223–226); V(227–231) and binary mixtures, such as K, Ba, Co, Cu, Fe, Mg, Mn, Ni, Pb and V(232–236) and improving the active phase distribution.

BASIC-CATALYZED REACTIONS (TABLE 3)

Although catalysis by solid acids had always received much attention due to itsimportance in petroleum refining and petrochemical processes, relatively fewstudies had been focused on catalysis by bases until last decade. However,during this period, base catalysts have played a decisive role in a number ofreactions mainly for fine-chemical synthesis. Easier separation and recovery ofthe products, catalysts, and solvents are some of themany advantages presentedby solid-base catalysts. From the point of view of fine chemicals synthesis,environmentally benign and more economical pathways are advantages thathave caused a remarkably increase in this research field (237). In this respect,heterogeneous catalysts are considered as an eco-friendly alternative. Martín-Aranda and coworkers have reported the use of basic solids such as alkali-dopedactivated carbons to catalyze selectively several reactions (238–245).

Recent years have seen the development of a number of new technologies,which offer the hope of providing the chemist with innovative synthetic routes assonochemical and microwave activated reactions. In general, the sonicationpresents beneficial effects on the chemical reactivity, such as reaction accelera-tion, to reduce the induction period, and to enhance the catalyst efficiency.Martín-Aranda et al. have synthesized α,β-unsaturated nitriles by sonochemicalactivated reactions of carbonylic compounds with malononitrile using two basiccarbons (Naþ– and Csþ–Norit) as catalysts. A substantial enhancing effect inyields and selectivities was observed by this group when the carbon catalyst wasactivated under ultrasonic waves.There is not before any report for the use ofactivated carbons as catalysts in combination with ultrasounds. The sonochem-ical phenomena originate from the interaction between a suitable field of acous-tic waves and a potentially reacting chemical system; the interaction takes placethrough the intermediate phenomenon of the acoustic cavitation. When one ofthe phases is a solid, the ultrasonic irradiation has several additional enhance-ment effects especially when the solid acts as catalyst. The cavitation effectsformmicrojects of solvent, which bombard the solid surface. This fact causes theexposition of unreacted surfaces of solid, increasing the interphase surface able



Table

3:Main

acid-a

ndbase

-catalyse

dreactio

nsusingactiv

atedcarbonsu

pportedmetal,non-m

etalo

rtheircompoundas

catalystsin

thelast

decade.

Precious

meta

lsAlkalimeta

lsTransitio

nmeta

lsOthers

Ru

LiNa

KCs

Mn

FeCu

WP

SiN

Acid-catalyze

dreactio

ns

-Azirid

inatio

nofo

lefin

s!

-Acylatio

nofa

lcoholsandamines

!!

!-A

cetalsandke

talssynthesis

!!

-Ethers

synthesis

!!

-Esters

synthesis

!!

-Enaminonessynthesis

!!

-Darkin-W

est

reactio

n!

!Ba

sic-catalyze

dreactio

ns

-N-a

ndC-Alkylatio

ns

!!

!!

!-S

ynthesisofα

,β-Unsa

turatednitrile

s!

!-C

laisen–Sc

hmidtc

ondensa

tion

!!

-Alkeneepoxidatio

n!

341


to react. (238). Enhancement effect on the reaction rate by combining the basicityof the carbon with ultrasounds is also presented as an alternativemethod for theproduction of differently substituted chalcones and, in general, for the produc-tion of other fine chemicals due to the mild conditions that this method offers.Chalcones are important intermediates in the synthesis of many pharmaceuti-cals and they are commonly synthesized via the Claisen–Schmidt condensationbetween acetophenone and benzaldehyde (Fig. 5) (239).

They have also reported the catalytic selective synthesis of N-alkylated imi-dazoles, which are key intermediates in the synthesis of pharmaceutically impor-tant anticonvulsants and bactericidal products. Basic carbons such asNa-, K- andCs-Norit or their binary combinations have been tested in the N-alkylation ofimidazolic rings with medium-chain and long-chain alkyl halides activated byultrasounds or under conventional thermal activation (Fig. 6) and in the N-propargylation of imidazole activated by microwaves and conventional thermalactivation. Carbon is known in microwave terminology as a very “lossy”material,which means that it is a very efficient absorber of microwave energy and convertsthat energy to heat. In their studies, they demonstrate how this fact can be used toreduce the reaction temperature and how the selectivity is modified (240–245).

O O O O

CarvoneCarvotanacetone Dihydrocarvone

Carvomenthone

Carveol

OHOH OH OH

Carvotanalcohol Dihydrocarveol Carvomenthol

Figure 5: Preparation of chalcones by Claisen-Schmidt condensation.

NH

N

N

Nbasic carbon

Br+

Figure 6: N-alkylation of imidazole with 1-bromobutane.



Wang et al. have reported the catalytic synthesis of propionitrile from alkyla-tion of acetonitrile by addition ofmethanol as a carbon source over activated carbon-supported alkali catalysts (LiNO3/AC, NaNO3/AC, KNO3/AC, CsNO3/AC andCh3COONa/AC, NaHCO3/AC) (246).

The chiral manganese (III) Schiff base complexes with a N2O2 coordinationsphere, generally known in the literatureasmanganese(III) salen complexes, havebeen reported by Silva et al. as very efficient catalysts in the asymmetric epoxida-tion of unfunctionalised alkenes (247). The importance of this system is due to itspractical use in laboratory and industry scale and to the broad use of epoxides asintermediates in organic synthesis; they can be easily transformed into a largevariety of compounds by means of regioselective ring opening reactions (248).

Fan et al. have reported the catalytic synthesis of dipropyl carbonate fromthe transesterification of dimethyl carbonate and propyl alcohol over K2CO3/ACcatalysts that show better catalytic activity than other base catalysts used inthis type of reaction (249).

ACID-CATALYZED REACTIONS (TABLE 3)

Though last decade is the decade for base catalysis, acid catalysis is continuouslyin expansion and trying to improve the reaction conditions according to theincreasing interest of getting environmentally friendly processes. So for examplethe need to develop a reusable and economic solid acid catalyst for the selectiveacylation of alcohols and amines employing carboxylic acids as acylating agentsto achieve high atom economy, have driven to Sreedhar et al. to prepare iron (III)oxide-containing activated carbon catalyst (250).

The aziridination of alkenes is a reaction of great importance since aziridinesare used as intermediates in organic synthesis for pharmaceuticals and agrochem-icals. Silva et al. have reported the catalytic activity of copper (II) acetylacetonatecomplexes anchored onto an activated carbon in the aziridination of styrene usingnitrene reagents (PhI¼NTs) as nitrogen source at room temperature (251).

Ketones and aldehydes can react with excess alcohol in acid medium to giveketals and acetals, respectively. Acetals and ketals are among the most importantperfume materials and industrial materials of organic synthesis. Yang et al. havereported thesynthesis ofacetalsandketals catalyzedby tungstosilicicacidsupportedon activated carbon. Heteropoliacids and their salts have interesting catalytic prop-erties for fine chemicals industries, and pharmaceutical and food and flavors indus-tries, etc. Activated carbon has been found to be able to entrap a certain amount ofheteropoly acids by equilibrium impregnation with water solvent (252).

Vegetable oils and animal fats can be transesterified to biodiesel for use as analternative diesel fuel. Conversion of low cost feedstocks such as used frying oils iscomplicated if the oils contain large amounts of free fatty acids that will formsoaps with alkaline catalysts. The soaps can prevent separation of the biodiesel



from the glycerin fraction. Kulkami et al. have prepared 12-tungstophosphoricacid (TPA) impregnated on activated carbon for the biodiesel production from lowquality canola oil containing up to 20 wt% free fatty acids (253). Mohammadpoor-Baltork et al. have also prepared 12-Tungstophosphoric acid (TPA)/AC catalystsfor the synthesis of oxazolines, imidazolines, and thiazolines in dry media (254).

Rafiee et al. have studied the catalytic activity of tungstophosphoric acidsupported on activated carbon in the synthesis of enaminones and in Dakin-West reaction for the production of β-acetamido ketones (255,256) and Obaliet al. in the synthesis of tert-amyl ethyl ether (257).

Shi et al. have reported the catalytic synthesis of n-dibutyl adipate byactivated carbon supported tungstophosphoric acid (258) and Liu et al., havesupported phosphotungstic acid on activated carbon to prepare catalysts for thesynthesis of dibutyl sebacate (259).

Lin et al. have investigated SiW12/AC catalysts prepared loading silico-tungstic acid on activated carbon for the synthesis of trioxane (260).

Zhou et al. have reported heteropolyacid supported on activated carbon byvaporization for the catalytic synthesis of aliphatic acetate by esterification ofacetic acid with various alcohols obtaining high yields (261). Juan et al. haveinvestigated the esterification of oleic acid by n-butanol over zirconium sulfatesuported on activated carbon catalysts (262).

Epoxide ring-opening reactions are useful tools in organic chemistry.Reactionsof epoxides are key processes for the transformation of aliphatic and aromaticcompounds. Durán-Valle et al. have investigated the epoxides (1,2-epoxyhexaneand styrene oxide) ring-opening reaction with 1-butanol (Fig. 7) and more recentlywith ethanol under microwave irradiation using activated carbons treated withmineral acids (HNO3 and sulfonitric mixture) as acid catalysts (263,264).Sulfonated activated carbon catalysts have been employed in different organicreactions such as the selective hydrolysis of cellulose into glucose (265), the alcoholacylation (etherification) and the epoxide-opening (266).

CATALYTIC C—C BOND FORMATION (TABLES 4A AND 4B)

There are several practical reactions to be applied to cost-effective large-scaleproduction of multifunctional intermediates for drug-synthesis such as Suzuki,Heck, Sonogashira, and Ullmann reaction.

OHO

RO

R

OH+

R = –Ph, –CH2CH2CH2CH3

Figure 7: Epoxides ring opening reaction with 1-butanol.



Table

4:Main

catalytic

reactio

nsofC

—C

bondform

atio

nandothera

pplic

atio

nsusingactiv

atedcarbonsu

pportedmetal,non

metala


thelast

decade(Table

4AandTa

ble

4B).

Table

4A

Preciousmeta

lsAlkali/

Alkaliearthsmeta

ls

PdPt

IrRu

Rh

Au

Ag

Na

KRb

Cs

BaMg

Ca

Catalytic

C–C

bondform

atio

nCarbonylatio

nofm

ethanol/alip

hatic

alcohols/e

thers/e

sters/R-X

!!

!Hyd

roform

ylatio

n!

Heckreactio

n!

Suzu

kiandMiyaura

reactio

n!

Ullm

annreactio

n!

Fuku

yamareactio

n!

Sonogash

irareactio

n!

Knoeve

nagelc

ondensa

tion

!!

Reductiv

ecouplin

gofh

aloaryls

!!

Markovn

ikovaddition

!Othera

pplic

atio

ns

Dehyd

rohalogenatio

n(β-Elim

inatio

nreactio

n)

!Dehyd

rogenatio

nofa

lkanes/cyc

loalkanes(p

roductio

nofH

2)

!!

!Dehyd

rogenatio

nofa

lcohols

!Cya

nosylilatio

nofa

ldehyd

es

Isomerizatio

nofp

olyunsa

turatedfattyacids

!!

!!

!1-buteneisomerizatio

nCatalyst-anodeforfuelc

ell

!!

!Ozo

natio

nPo

lymerizatio

nofc

ycloalkenes

Olig

omerizatio

nofh

ydrocarbons

!Denitrificatio

nofw

ater(

DeNOx)

!!

Photocatalyst

Hyd

rosilylatio

nofa

lkenes

!Fisc

her-T

ropsc

hsynthesis

!Ammonia

synthesis

!!

!Ammonia

decompositio

n!

CF 3Isyn

thesis

!!

!!

Oilyield

(coale

xtractio

n)

Antib

acteria

lactiv

ity!

!!

Glycerold

ehyd

ratio

n

345


Table

5:

Table

4B

Transitio

nmeta

lsOthers

TiV

Mn

FeCo

NiMo

WRe

Os

BiCu

ZnSn

Ce

ZrLa

Cr

Si

Catalytic

C–C

bondform

atio

n-C

arbonylatio

nofm

ethanol/alip

hatic

alcohols/e

thers/

esters/R-X

!!

-Hyd

roform

ylatio

n-H

eckreactio

n-S

uzu

kiandMiyaura

reactio

n!

-Ullm

annreactio

n-F

uku

yamareactio

n-S

onogash

irareactio

n-K

noeve

nagelc

ondensa

tion

-Reductiv

ecouplin

gofh

aloaryls

-Markovn

ikovaddition

Othera

pplic

atio

ns

Dehyd

rohalogenatio

n(β-Elim

inatio

nreactio

n)

!Dehyd

rogenatio

nofa

lkanes/cyc

loalkanes(p

roductio

nofH

2)

!!

!!

!

Dehyd

rogenatio

nofa

lcohols

!!

!Cya

nosylilatio

nofa

ldehyd

es

!Isomerizatio

nofp

olyunsa

turatedfattyacids

!!

1-buteneisomerizatio

n!

Catalyst-anodeforfuelc

ell

!!

!Ozo

natio

n!

!!

!!

!Po

lymerizatio

nofc

ycloalkenes

!!

!Olig

omerizatio

nofh

ydrocarbons

!Denitrificatio

nofw

ater(

DeNOx)

!!

Photocatalyst

!!

!Hyd

rosilylatio

nofa

lkenes

!Fisc

her-T

ropsc

hsynthesis

!!

!!

!!

Ammonia

synthesis

!!

Ammonia

decompositio

nCF 3Isyn

thesis

Oilyield

(coale

xtractio

n)

!!

!Antib

acteria

lactiv

ity!

!!

!Glycerold

ehyd

ratio

n!

!

346


The Suzuki reaction (or Suzuki-Miyaura reaction) is the organic reaction ofan aryl- or vinyl-boronic acid with an aryl- or vinyl-halide catalyzed by a palla-dium catalyst. It is widely used to synthesize poly-olefins, styrenes, and sub-stituted biphenyls. Several reviews have been published using differentpalladium supported catalysts such as palladium nanoparticles supported onactivated carbon (267–269).

The Heck reaction is the chemical reaction of an unsaturated halide with analkene and a strong base and palladium catalyst to form a substituted alkene.The halide or triflate is an aryl, benzyl, or vinyl compound and the alkenecontains at least one proton and is often electron-deficient such as acrylateester or an acrylonitrile.The catalysts employed have been tetrakis(triphenyl-phosphine)palladium, palladium chloride or palladium acetate. The ligand istriphenylphosphine or BINAP (2,2’-bis(diphenylphosphino)-1,1’-binaphthyl).The base is triethylamine, potassium carbonate, or sodium acetate. Severalinvestigations are reported in literature about the Heck reaction catalyzed bypalladium-supported activated carbon catalysts (Fig. 8) (270–275).

Other catalysed C–C coupling organic reactions besides Heck reaction, havebeen carried out over palladium complexes and palladium on activated carboncatalysts. For example, Sonogashira reaction, a coupling reaction of terminalalkynes with aryl or vinyl halides, Ullmann reaction is a coupling reactionbetween aryl halides and Fukuyama reaction is a palladium catalysed couplingof organozinc compounds with thioesters to form ketones. In organic synthesis,Ullmann reaction is less typical, and it is often replaced by Heck reaction andSonogashira coupling (276,277).

Mukhopadhyay et al. have reported the coupling of substituted haloben-zenes to the respective biphenyls using a combination of a reducing agent andaweak base (Na2CO3) in the presence of catalytic tetrabutylammonium bromide(TBAB) and palladium that are both supported on activated carbon. The resultsare explained with postulation of a physical micro-membrane formed in situ bythe phase-transfer catalyst (278).

Carbonylation reactions are of major importance in both organic and indus-trial chemistry. Due to the availability, price, and reactivity pattern, carbon

R

Br

+Pd/C, base

solvent, 140 ºC-HBr R

+

RE- and Z-isomersR = H, OCH3, COCH3

Figure 8: Heck coupling of bromoarenes with styrene catalyzed by Pd supported activatedcarbon catalysts.



monoxide is becoming a more and more important building block for fine andbulk chemicals. Carbonylation reactions involve the insertion of 4C¼O moietywith or without other groups (if any, as -OMe, -OEt, etc.) into a substrate whichmay be of varied types such as alkenes, alcohols, alkynes, alkyl halides, amines,nitro compounds or substituted aromatic analogs of these. Protzmann et al. haveimproved the selectivity in the catalytic carbonylation of 1,3-butadiene to 3-pentenoic acid immobilizing rhodium on activated carbon (279). Some authorshave studied the stability of Rh/AC and Ni/AC catalysts in the liquid-phase andvapour-phase carbonylation of methanol (280–282). Merenov et al. and Penget al. have reported the direct vapor-phase carbonylation of methanol on Ni/ACand NiCl2-CuCl2/AC catalysts obtaining a high selectivity to methyl acetate(283,284). More recently, Kosmambetova et al. have carried out the methaneoxidative carbonylation catalyzed by rhodium chalcogen halides over activatedcarbon support (285).

Some authors have reported a variety of carbonylation reactions, the hydro-formylation (oxo synthesis) of long-chain alkenes over rhodium complex inmobi-lized on activated carbon. This reaction is an important industrial process for theproduction of aldehydes from alkenes. It is important because the resultingaldehydes are easily converted into many secondary products (286–291).

There is another type of reaction catalysed by alkali solid catalysts andreported by Calvino-Casilda et al., the Knoevenagel condensation, which hasbeen used to measure the strength of the basis sites and can be used to form C–Cbonds through the reaction of a carbonyl with an activated methylenic group.They have reported the condensation of benzaldehyde and different substitutedbenzaldehydeswith ethyl cyanoacetate usingNa-Norit andCs-Norit as catalystsin dry media. The reaction products are precursors in the production of 1,4-dihydropyridine derivatives, which have expanding practical applications aspharmaceuticals in the line of calcium channel blockers (Fig. 9) (292).

OTHER REACTIONS (TABLES 4A AND 4B)

During the 20th century, the catalytic ammonia synthesis has grown to be amongthe most important industrial processes. Ru-based materials are the second-generation catalysts for ammonia synthesis. Ruthenium is less inhibited by

CHO

R1

R2

O

COOEtCOCH3

COOEtR1R2

catalyst+

Figure 9: Knoevenagelcondensationbetweensubstitutedbenzaldehydesandethylacetoacetatefor thesynthesisofbencilidenderivatives in theproductionof 1,4-dihydropyridines (R1¼NO2,H, R2¼H,NO2).



ammonia, less sensitive to poisons, andmore active than the traditional iron-basedcatalyst. Ru-based activated carbon supported catalysts with promoters as bariumand potassium have been reported by many authors to be active for ammoniasynthesis (293–300). Fe, Co and Fe-Co/AC catalysts were proposed by Rarog-Pilecka et al. as catalysts for ammonia synthesis using barium and potassiumpromoters (301).

Catalytic ammonia decomposition has attracted significant and increasingattention as a means of supplying pure hydrogen for fuel cells. Rarog-Pileckaet al. have reported Ru/AC catalysts for ammonia decomposition (302). Pd/ACand Pt/AC catalysts have been employed on cyclohexane dehydrogenation andPt/AC and Pt-Re/AC catalysts have been employed in the dehydrogenation ofdecalin in the hydrogen supply to fuel cells (108,303–306). Shimada et al. havecarried out the dehydrogenation of iso-butane over Fe/AC catalysts and Silvestreet al. over Pt-Zn/AC catalysts obtaining high selectivity to isobutene (143,307).Vanadium and iron oxides, vanadium and magnesium and copper supported onactivated carbon have been proposed as catalysts for ethylbenzene dehydrogena-tion to styrene a high value chemical (Fig. 10) (308–312). Pt, Cu-Pt, Cu, CoO,Co3O4, Cu2O, and NiO supported on activated carbon catalysts were employedon dehydrogenation of alcohols such as cyclohexanol and isopropanol (313–315).

The catalytic decomposition of ozone is an important area of research fromenvironmental and health point of view. Ozone decomposition has been reportedovermetal oxide supported on activated carbon catalysts,MnO2�, Co3O

4�, Fe2O3�,

and NiO/AC by Heisig et al. (316).Nitrogen occurs in raw surface water in the form of organic nitrogen, ammonia,

nitrate and nitrite, all of which are undesirable in drinking water. The biologicaldenitrification of water is a convenient and cost-effective alternativemethod for theremoval of nitrate and nitrite ions from waters. Most studies on denitrification byheterotrophic denitrifyingbacteriahave shown that the cultures require a carbonasan electron donor for the reduction of nitrate andnitrite,whichmust be added to thewater being treated. Lemaignen et al. have reported the catalytic denitrification ofwater usingmetal-activated carbon supported catalysts, Pd- andPdSn/ACcatalystsfor nitrate reduction (317) and Soares et al. have recently reported the nitrate and

CH2

CH3

CHH2C

+ H2

Ethylbenzene Styrene

Figure 10: Ethylbenzene dehydrogenation to styrene.



nitrite reduction in water over bimetallic catalysts Rh-Cu/AC and Pd-Cu/AC (318).Under anaerobic conditions,many bacteria use nitrate and nitrite ions contained incontaminated waters for respiration. Moreno-Castilla et al. have studied the deni-trification of water under anaerobic conditions by using Escherichia coli supportedor immobilised on different activated carbons. Activated carbons offer the advan-tages of a large adsorptive capacity and an irregular shape, which acts as a shelterfor bacteria from high fluid shear forces (319).

Environmental photochemistry using semiconductors is the part of a generalgroup of chemical remediation methods known as Advanced Oxidation Processes(AOPs). These methods are based on one distinguishing feature—the generationand use of hydroxyl radicals as the primary oxidant for the degradation of organicpollutants.Among the several semiconductors,TiO2 is reported tobeaBenchmarkphotocatalyst. TiO2 is anchored or embedded onto supportmaterials suchas silica,alumina, zeolites, clay and activated carbon being this last the most commonlyused adsorbent for water treatment. Activated carbon has a large specific surfacearea and awell-developed porous structure, resulting in an attractive force towardorganic molecules (320–328). Many authors have based their investigations onusing TiO2/AC as catalyst; Arana et al., the gas-phase alcohols photocatalyticdegradation (329); Parra et al. the photocatalytic degradation of atrazine (330);Zou et al. the photocatalytic degradation of toluene (331); Subramani et al. thephotocatalytic degradation of indigo carmine dye (332); Chen et al. the photocata-lytic degradation of methylene blue (333); Li et al. the photocatalytic degradationof Rhodamine B (334); Gauthier et al. the photocatalytic degradation of esters asethyl hexanoate (335); some other authors the removal of phenol and phenolderivatives fromwater (336–338); Geng et al. the decomposition of aqueous hydro-quinone (339); Sleiman et al. the photocatalytic removal of pesticide dichlorvosfrom indoor air (340) and Nada et al. have studied the photocatalytic hydrogenproduction (341).Wang et al. have reported the photodegradation of L-acids undervisible light overMo-TiO2/AC catalysts andFollansbee et al. the photodegradationof reactive red dye (342,343). Hilal et al. supported TiO2/TPPHS (2,4,6-triphenylhydrogen sulphate) onto activated carbon (AC) to yield a new class of catalyticsystem AC/TiO2/TPPHS for the photo-degradation of phenol and benzoic acid inwater (344).More recently, Puma et al. have reviewed the preparation of titaniumdioxide loaded onto activated carbon support and its photocatalytic activity in avariety of investigations as i.e. from water decontamination to direct pollutantdegradation in aqueous and gas phase systems using UV irradiation and latelywith the assistance of ultrasonic sound waves (345).

However, ZnO is found to be a suitable alternative to TiO2. For practical applica-tions there are some difficulties such as either filtration of fine TiO2 or fixation ofcatalyst particles and efficient utilization of UV/Solar light. For these reasons manyresearchers have been working to increase the efficiencies of this process by mod-ification of its surface. Sobana et al. have evaluated the degradation efficiency of ZnOloaded activated carbon catalysts (AC–ZnO composite photocatalyst)with solar light



at roomtemperatureusinganazodyeDirectblue53 (DB53)andhavealso studied itsphotocatalytic activity on 4-acetylphenol degradation (346,347). Lee et al. havestudied the photochemical activity of Zn/AC catalysts by measuring the humic acid(HA) removal efficiency using UV/photocatalyst system (348). Xu et al. have synthe-sized fluorine-doped titania-coated activated carbon catalysts with photocatalyticactivity in the degradation of phenol under visible light (349).

The Fischer-Tropsch process is a catalyzed chemical reaction in which carbonmonoxide and hydrogen are converted into liquid hydrocarbons of various forms.Typical catalysts used are based on iron and cobalt. The principal purpose of thisprocess is to produce a synthetic petroleum substitute, typically from coal ornatural gas, for use as synthetic lubrication oil or as synthetic fuel. Some authorshave proposed Fe-Co/AC, Fe-Cu-K/AC and Fe-Mo-Cu-K/AC catalysts for Fischer-Tropsch synthesis (350) andmore recentlyWang et al. have reported the influenceof lanthanum on the performance of Zr-Co/AC catalyst in this reaction (351).

Electrochemical fuel cells convert the chemical energy of a fuel directly intoelectric power employing a catalytic process. Fuels for this kind of power gen-eration, such as hydrogen or methane, are oxidised at the anode of the fuel cell,while oxygen is simultaneously reduced at the cathode. The only off-gas productof hydrogen fed fuel cell is water vapour. Maruyama et al. have found thatplatinum supported on activated carbon is an effective electrocatalyst for poly-mer electrolyte fuel cells improving the activity for oxygen reduction (352–354)and Guha et al. have employed Pt/AC catalysts in fuel cell electrodes (355).Ominde et al. have studied the effect of oxygen reduction on activated carbonelectrodes loaded with manganese dioxide catalyst (356). Zhou et al. havereported Pt-based anode catalyst supported on activated carbon for direct etha-nol fuel cells (357) and more recently, Tapan et al. have tested activated carbon-based Ag-Cu electro-catalyst for anode electrode in direct ethanol fuel cells (358).PtRu/AC catalysts have been tested in the methanol electro-oxidation and asanode catalyst of the direct methanol fuel cell (DMFC) by some authors(359,360). More recently, Kerzenmacher et al. have reported Pt-Bi based anodecatalyst supported on activated carbon for glucose oxidation (361).

Organosilicon compounds have attracted much interest from viewpoints oforganic synthesis as well as new functional materials. This trend of organome-tallic chemistry has prompted us to develop new methodologies for stereoselec-tive formation of silicon-carbon bonds. The utility of hydrosilylation as asynthetic tool has even been extended into the area of enantioselective reactions.Maciejewski et al. have presented Pt-Cu/AC catalysts for the hydrosilylation ofalkenes with poly(hydro,methyl)siloxanes in the synthesis of silicone waxes(362).Baleizao et al. have reported that aldehydes can react with trimethylsilylcyanide under both thermal and catalytic conditions to give α-silyloxy nitrileswhich may be useful intermediates and protective groups in organic synthesis.They tested chiral vanadyl salen complex anchored on activated carbon catalystsin the studied reaction (363).



Nagasaki et al. have reported a novel catalytic reaction and its mechanismfor CF3I synthesis using alkali metal salts supported on activated carbon. Thereis incentive to synthesize this molecule in a low-cost route for using it as arefrigerant and also because it useful a foam blowing agent and can be used toreplace more environmentally damaging foam blowing agent previouslyemployed in the production of polymeric foams (364).

Polymerization of α-pinene using cooper, nickel, and vanadium oxides sup-ported on activated carbon was carried out by Encarnação et al. to obtain poly-mers of low molecular weigh. Pinene homopolymers belong to the family ofterpenic resins that are low molecular weight valuable commercial productsused by the adhesive, sealant, wax coating, and casting industries. They arebicyclic isomers that undergo cationic polymerization by ring opening of theircyclobutane ring (Fig. 11) (365). Later Milewska et al. carried out the hydro-genation of α-pinene in high-pressure carbon dioxide using Pt/C catalysts (366).Experiments were performed at different carbon dioxide pressures, so that thereaction mixture in contact with the solid catalyst would either be biphasic(liquid þ gas) or a single supercritical phase. The hydrogenations in biphasicconditions, at lower carbon dioxide pressures, are completed faster than insupercritical conditions.

CH3

α -Pinene

CH3

+

CH3

H3C CH3

CH3

+

+

Tricyclene

Camphene

CH3

CH3

CH3H3C

CH3

H3C CH3H3C CH3

CH3CH

3

Limonene

γ -Terpinene

Terpinolene α -Terpinene

HC3

HC3

H3C

H3C

H2C

H2C

HC3

Figure 11: Polymerization of α-pinene.



Chakraborty et al. have reported the formation of oligomerization hydro-carbon products from an equimolar mixture of CF2Cl2 and H2 catalyzed byactivated carbon-supported Pt-Cu catalysts (367).

Moreno-Castilla group has prepared tungsten oxide catalysts supported onactivated carbons for the isomerization of 1-butene (368,369). Bernas et al. havereported the isomerization of polyunsaturated fatty acids such as linoleic acid toconjugated linoleic acid (CLA) over the following catalysts; Ru, Ni, Pd, Pt, Rh, Ir,Os and bimetallic Pt-Rh supported by activated carbon. Conjugated linoleic acid(CLA), is being sold as a panacea that has the capability of reduce or eveneliminate cancer, preventing heart disease, improve immune function, and alterethe body composition in order to treat obesity or build lean body mass (370).

Ucar et al., have reported the upgrading scrap tire derived oils using Co-Ni/AC, Co-Mo/AC and Ni-Mo/AC catalysts (371).

Methakhup et al. have improved oil yield from coal extraction using Fe-Ni/AC, Ni-Mo/AC and sulphide catalysts Fe2S3/AC (372).

Nosheen et al. have investigated the microwave assisted cracking of n-hexane over Pt/AC catalysts to produce lower hydrocarbons (C2 and C3) toefficiently activate automobile catalysts (373).

Faria et al. have reported cerium, manganese and cobalt oxides as catalyst forthe ozonation of selected organic compounds (aniline and sulfanilic acid) and azodyes (374) andLi et al. have reported the catalytic ozonationof p-chlorobenzoic overNi/AC catalysts (375). Hammad et al. have prepared catalysts doping activatedcarbon with chromia gel for ozone decomposition and DEHP degradation (376).

Xu et al. have generated hydrogen from alkaline NaBH4 solution via hydro-genolysis using Co/AC catalysts (377).

Shargi et al. have prepared cobalt(III)-salen complex supported on activatedcarbon as an efficient heterogeneous catalyst for synthesis of 2-arylbenzimidazolederivatives from phenylenediamines and aromatic aldehydes (378).

Hisashi et al. have reported the antibacterial activity of Co, Zn,Ni,MgandCa/AC catalysts against bacteria’s such as S. aureus and B.subtilis (379) and laterKennedy et al. reported the use of Cu/AC catalysts for the destruction of thesepathogens in water (380). More recently, Liu et al. have reported the antibacterialactivity of Ag/AC catalysts against S. Aureus and for bacteria’s E. coli (381).

Hutchings have carried out the ethyne hydrochlorination over Au/AC cata-lyst with the formation Markovnikov addition products (382). Ning et al. havereported the glycerol dehydration to acrolein over activated carbon-supportedsilicotungstic acids (383).

CONCLUSIONS AND FUTURE TRENDS

Catalytic processes report more than 90% of the chemical manufacturing pro-cesses in use all over the world. The catalyst increases the rate of a reaction andcontrols its selectivity. Catalyst development is a complex process, requiring



extensive research to produce the high performance catalysts used today.Activated carbons have beenused for some time in heterogeneous catalysis, actingas direct catalysts and not long as catalyst support. It is now recognized thatactivated carbon as a catalyst support offers unparallel flexibility in tailoring theirphysical (surface area and porosity) and chemical (surface functional groups)properties to specific needs, thus showing the remarkably wide range of potentialapplications. However, the future growth of the use of the activated carbon incatalysis depends on the better understanding and subsequent control of thechemistry of activated carbon surface. Specifically the role of the chemical natureof the activated carbon surface has become widely recognized during the last fewyears. In this way, physical and chemical surface properties of activated carbonhave to be taken into account when designing a catalyst. Since in 1998 Rodríguez-Reinoso reviewed the properties of activated carbon as catalyst and catalystsupport, many advances has been got in this field especially on activated carbonsupported catalytsts. Therefore, this review gives an overview of current chemicalprocesses catalyzed by activated carbon supported catalysts in the last decade.

The properties and requeriments of activated carbon supports are closelyrelated to the requirements of the catalyst. The important parameters for activityand selectivity of a catalyst are not only surface area, porosity, inertness, purity,surface functional groups (catalyst manufacturing), cost efectiveness but alsomechanical stability needs to be considered for the recyclability of the catalyst(green chemistry).

ACKNOWLEDGMENTS

V.C.C. acknowledges CSIC for the award of a JAE-Doctor contract. Thework hasbeen supported by Spanish Ministry of Education and Science (project:CTM2007-60577/TECNO). This review is dedicated to Prof. J. de Dios López-González, who showed us how attractive, is catalysis on activated carbons.

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[373] Methakhup, S.; Ngamprasertsith, S., and Prasassarakich, P. (2007) Improvementof oil yield and its distribution from coal extraction using sulfide catalysts. Fuel,86: 2485.

[374] Faria, P.C.C., Monteiro, D.C.M., Órfão, J.J.M., and Pereira,M.F.R. (2009) Cerium,manganese and cobalt oxides as catalysts for the ozonation of selected organiccompounds. Chemosphere, 74: 818.

[375] Li, X., Zhang, Q., Tang, L., Lu, P., Sun, F., and Li, L. (2009) Catalytic ozonation ofp-chlorobenzoic acid by activated carbon and nickel supported activated carbonprepared from petroleum coke. J. Hazard. Mater., 163: 115.

[376] Hammad Khan, M., and Jung, J.Y. (2008) Ozonation catalyzed by homogeneousand heterogeneous catalysts for degradation of DEHP in aqueous phase,.Chemosphere, 72: 690.

[377] Xu, D., Dai, P., Guo, Q., and Yue, X. (2008) Improved hydrogen generation fromalkaline NaBH4 solution using cobalt catalysts supported on modified activatedcarbon, Int. J. Hydrogen Energy, 33: 7371.

[378] Shargi, H., Aberi, M., and Doroodmand, M.M. (2008) Reusable cobalt(III)-salencomplex supported on activated carbon as an efficient heterogeneous catalyst forsynthesis of 2-arylbenzimidazole derivatives. Adv. Synthesis Catal., 350:2380.

[379] Hisashi, T., Nobuyoshi, K., Kazuhisa, O., and Hajime, Y. (2001) Antibacterialactivated carbons prepared from pitch containing organometallics Carbon, 39:1963.



[380] Kennedy, L.J., Kumar, A.G., Ravindran, B., and Sekaran, G. (2007) Copperimpregnated mesoporous activated carbon as a high efficient catalyst for thecomplete destruction of pathogens in water. Environ. Progress, 27: 40.

[381] Liu, W., Yuan, H., Lu, J., and Yang, S. (2008) Improvement of antibacterialactivity of activated carbon supported with silver by liquid oxidization. Ion Exch.Adsorp., 24: 124.

[382] Hutchings, G.J. (2009) Catalyst Synthesis Using Supercritical Carbon Dioxide: AGreen Route to High Activity Materials Top. Catal. 52: 982.

[383] Ning, L., Ding, Y., Chen,W., Gong, L., Lin, R., Yuan, L., andXin, Q. (2008) GlycerolDehydration to Acrolein over Activated Carbon-Supported Silicotungstic AcidsChin J. Catal., 29: 212.



Last Decade of Research on Activated Carbons as Catalytic Support

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