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Last Decade of Research on Activated Carbons as Catalytic Support in
Chemical Processes
V. 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 de
Educación a Distancia (UNED), Madrid, Spain c Dpto. de Química Orgánica e Inorgánica, Facultad de
Ciencias, 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) 'Last
Decade of Research on Activated Carbons as Catalytic Support in Chemical Processes', Catalysis Reviews, 52: 3, 325 —
380
To link to this Article: DOI: 10.1080/01614940.2010.498748
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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

Last Decade of Research on
Activated Carbons as
Catalytic Support in Chemical
Processes
V. Calvino-Casilda1, A.J. López-Peinado2, C.J. Durán-Valle3,
and R.M. Martín-Aranda2
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1
Catalytic Spectroscopy Laboratory, Instituto de Catálisis y Petroleoquímica (CSIC),
Madrid, Spain
2
Dpto. de Química Inorgánica y Química Técnica, Facultad de Ciencias, Universidad
Nacional de Educación a Distancia (UNED), Madrid, Spain
3
Dpto. de Química Orgánica e Inorgánica, Facultad de Ciencias, Universidad de
Extremadura, Badajoz, Spain
This review is devoted to the application and knowledge developed in the past 10 years in
the area of chemical processes catalyzed by activated carbon supported catalysts.
Activated carbons are well known for their catalytic properties and for being used as
support in heterogeneous catalysis. The supported catalysts have been successfully used
in the chemical industries for long time. In the last decade, carbon supported catalysts
have opened the door for new chemical catalytic processes based on their intrinsic
features. However, fundamental understanding of molecular structure-reactivity
relationship of these carbon materials remains unexplored. Futures advances in all
areas may be possible through combined experimental and theoretical approaches.

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

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

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

325

326 V. Calvino-Casilda et al.

Supported catalysts are of special interest. They allow the fine dispersion
and stabilisation of small metallic particles providing access to a much larger
number of catalytically active atoms. In particular, it has been observed that
activated carbon exhibit optimum properties and performance, stability in both
acidic and basic media that let them to be used as catalyst support in multitude
of different applications in the chemical industry.
At the beginning of last decade, Rodríguez-Reinoso remarked the use of
carbon as catalyst support for different industrial processes (2). In the past,
the lack of fundamental understanding of many aspects of the use of carbon in
catalysis caused a limited employ of carbon as catalyst and still more as catalysts
support. But the continuous studies on understanding of all aspects of the
physical and chemical characteristics of carbon material, especially activated
carbon, AC (surface area and porosity) and even more, the possibility of control-
ling the surface chemistry of such materials is the origin of important researches
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carried out in industrial chemistry during the last decade. As a result, this paper
reports the evolution in the last decade of the use of activated carbon as catalyst
support employed in a variety of current industrial processes.
In heterogeneous catalysis, carbon materials have been used for long time
because they can be used directly as catalysts, and moreover, they can satisfy
most of the properties desired for a suitable support. It has been shown that
although 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 of
carbon surface chemistry is also extremely important. The most common het-
eroatoms present on carbon surface are hydrogen, oxygen, nitrogen, sulphur and
phosphorus. These atoms are arranged in the forms of functional groups, such
acidic ones as carboxylic, lactonic, phenoclic, or basic groups, such as pyranes
and chromene. The number and strenght of these groups influence the apparent
acidity or basicity of the carbon surface. Moreover, a few percent of inorganic
matter from the organic precursor (e.g. coal or wood) could be present on carbons
and this fact is considered important for their perfomance, especially when they
are used as catalyst supports. However, although the catalytic effect is mainly
headed by the chemical properties of the active phase, the dispersion and the
local distribution of the active phase across the activated carbon support as well
as the interaction active phase-support are significantly important. These are
just the aspects of carbon supports that make them so attractive for heteroge-
neous catalysis. These parameters can be modified to satisfy any specific
requirement during catalyst preparation making the surface not only physically
but also chemically accessible to the precursor and diminishing the deactivation
by 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 key
for their uses, and that both physical and chemical surface properties of carbon
support have to be taken into account when designing a solid catalyst. Due to the
constant interest in heterogeneous catalysis of using activated carbon as

Last Decade of Research on Activated Carbons 327

catalyst support in search of suitable catalysts for certain chemical processes,
this review will be mainly concerned with the use of carbon as catalyst support to
highlight 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 chemical
industry 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 and
intermediates used in the manufacture of industrial products and consumer
goods. 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 the
last decade, industrial researchers have expended great efforts to make selective
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oxidation processes and their catalysts even more efficient and environmentally
friendlier. Among these catalysts activated carbon supported materials have
been 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 the
treatment of gaseous effluents to destroy the VOCs emissions, where advantage
is taken of the enhanced retention of organic pollutants in the pore system of the
carbon. Platinum supported on activated carbon has been used as catalyst and
other less expensive alternatives have been also considered; an increasing inter-
est is associated with activated carbons impregnated with transition metal
oxides (3–5). Recently Lu et al. have tested transition metals (Cu, Co, Fe and
Ni) supported on activated carbon in the simultaneous removal of VOC and NO
in combustion flue gas (6) and Wu et al. have prepared Pt/AC catalysts for
benzene, toluene and xylene (BTX) deep oxidation at low-temperature on the
catalytic destruction of VOC (7). Suh et al. have investigated a Co/AC catalyst
activated with ozone for removing chemically offensive odors such as benzene,
toluene, mercaptans, and sulfides (8). Cherkezova-Zheleva et al. have also
investigated 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 methyl
mercaptan on activated carbons, the performance of materials can be enhanced
by impregnation of activated carbon with basic compounds such as NaOH,
Na2CO3, KOH and K2CO3 (10,11). They are able to improve the capacity of
carbons for methyl mercaptan removal by a factor of two (10). Other possibility
to 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 ).

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Table 1: Main oxidation reactions catalysed by activated carbon supported metal, non-metal and their compound catalysts in
the last decade.

Alkali
Precious Alkali earths Transition
metals metals metals metals Others
Catalytic
oxidations Pd Pt Ru Rh Ag Au Na K Ca V Cr Mn Fe Co Ni Mo W Re Sn Bi Cu Zn P Ce

-Oxidation of hydrocarbons
- Alkanes/ cycloalkanes ! ! ! ! ! !
- Methane reformation ! ! !
- Alkenes/ cycloalkenes ! ! ! !
- Aromatics ! ! ! ! ! ! !
- Oxidation of halocarbons ! ! ! ! ! !
- Oxidation of aldehydes ! ! ! ! !

328
- Oxidation of carboxylic acids !
- Oxidation of alcohols
- Aliphatics ! ! ! ! ! ! ! ! ! ! ! ! !
- Phenols ! ! ! ! ! ! ! ! !
- Carbohydrates ! ! ! ! !
- Oxidation of cyclic ketones !
- Oxidation of dye wastewater ! ! !
- Ethers and esthers !
- CO oxidation ! ! ! ! ! ! ! ! ! ! !
- NO oxidation ! ! ! !
- SO2 oxidation ! ! ! ! !
- H2S and sulphides oxidation ! ! ! ! ! ! ! ! !
- H2oxidation ! !
- Desulphurisation reaction ! ! !
- Ammonia ! ! ! ! ! ! ! !

The application of innovative advanced oxidation technologies (AOTs) like the oxidation of 4-chlorophenol (an important toxic pollutant) with hydrogen peroxide in aqueous solution using Fe/AC cata- lysts is of interest to abate efficiently and also reduce the treatment cost through destructive techniques mineralizing the halocarbon (15).20). and the dechlorination of drinking water. pesticides. Zazo et al.18). Co. the paint industry. have prepared Co- Ce/AC as a new catalyst for catalytic wet air oxidation of phenol (31) and Kim et al. Bandosz et al. The catalytic wet-air oxidation (CWAO) process is effective in converting organic pollutants such as phenolic pollutants to innocuous carbon dioxide currently found in industrial wastewaters.27). Several activated carbon-supported chromium oxide catalysts were effective for complete chlorinated volatile organic compounds (CVOCs) oxidation such as methylene chloride and perchloroethylene (19. Noble metal catalysts on activated carbon (Pt/AC and Ru/AC) and base- metal catalysts (Cu/AC. 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 by providing new Brönsted acidic centers that form strong interactions with the adsorbed gas in its protonated form (26. Last Decade of Research on Activated Carbons 329 Some authors have carried out low temperature hydroxylation of aromatic compounds by hydrogen peroxide over Fe/AC and Pd/AC catalysts (13). Mo/AC and Mn/AC) were developed and examined for the simultaneous removal of organic pollutants and ammonia from wastewater using the wet air oxidation (WAO) process in the liquid phase (24. have examined the chemical reactivity of AC-supported iron as a catalyst to decompose polychlorinated biphenyls (PCBs) under air or N2 atmo- sphere (17. Pt on TiO2-grafted activated carbon. have studied the catalytic wet peroxide oxidation of phenol with a Fe/AC catalyst in aqueous solution (28. chemical and solvent manufacturing. Alkylated benzenes are an important class of hydrocarbons because they com- prise a significant portion of gasoline and diesel fuels. have also Downloaded At: 18:30 25 January 2011 carried out the oxidation of 4-chlorophenol over Pd/AC catalysts used for gas- diffusion electrode (16).29). Alvarez-Merino et al. Wen et al. have reported the catalytic combustion of toluene over tungsten oxide supported on activated carbon catalysts for removing toluene from dilute streams (14). CoMo/AC. have carried out the catalytic wet oxidation of aqueous p-chlorophenol over supported noble metal activated carbon catalysts and Sun et al. Lei et al. Qin et al. and Quintanilla et al. have studied the effects of inorganic cocatalysts (Ce.25). have reported the behaviour of Cu-Ce/AC catalyst-sorbent in the dry oxidation of phenol showing high phenol adsorption capacities and high phenol oxidation activities (30). Halocarbons represent the most abundant family of industrial toxic compounds as it has been recently recognized from different polluting sources like herbi- cides. CuO/AC and Fe/AC are some of the catalysts employed for the wet air oxidation (21–23). Wang et al. Mn and Cu) and initial states of Pd on the oxidative carbonylation of phenols over heterogeneous Pd/AC catalysts following the well-known “redox” or “multi-step electron .

transfer mechanism” between a Pd complex and organic/inorganic cocatalysts (32). 1). Nowadays gold supported on activated carbon is the preferred catalyst for the oxidation of the alcoholic and the aldehydic groups and one of the best preparation methods of those catalysts is the immobilisation of colloidal particles. Calvino-Casilda et al. they are potentially valuable as chemical intermediates in the fine chemicals industry. if the products could be formed in high selectivity. including diols. . have presented Au/AC and Au-Pd/AC as selective catalysts for the oxidation of alcohols such as glycerol. 330 V. they have established that by using bimetallic cata- lysts (Au-Pd/AC and Au-Pt/AC) a strong synergistic effect was shown and high activity and a prolonged catalyst life were also found (38.39). Due to their observation in previous works that the metallic character of palladium was significantly enhanced after the reaction. Prati et al. have carried out the removal of phenolic pollutant in aqueous solution by microwave-assisted catalytic oxidation using Pt/AC catalysts showing better results than in the catalytic wet air oxidation previously reported (33). Downloaded At: 18:30 25 January 2011 A large number of products can be formed from glycerol oxidation being one of the key problems the selectivity by which the individual products can be formed (Fig. Glycolic acid Glyceraldehyde Glyceric acid Tartronic acid Glyoxilic acid Glycerol Dihydroxyacetone Hydroxypyruvic acid Mesoxalic acid Figure 1: General reaction pathways for glycerol oxidation. under relatively mild condi- tions (34–37). they investigated the effects of the initial state of Pd on the catalyst activity and product selectivities for a fixed amount of Pd added with a fixed amount of cocatalys concluding that the catalytic performance was independent of the different initial states of Pd in Pd/AC catalysts. Nevertheless. More recently. Demirel-Gulen et al. Recently Bo et al.

and CH4 (50). have studied the oxidation of glyoxal into glyoxalic acid over Pd/C catalysts (44). Porta et al. Some authors have studied the role of copper chloride (63. Bian et al. have also investigated the glycerol oxidation reaction (40). Glycerol can be oxidised to glyceric acid with 100% selectivity at high conversion using Au/AC as catalyst (41). (54). ruthenium. Downloaded At: 18:30 25 January 2011 palladium. have studied the catalytic vapor phase synthesis of diethyl carbonate from CO and ethyl nitrite over catalysts prepared from PdCl2-CuCl2 and PdCl2-CuCl2- CeCl3 supported on activated carbon (59). have studied the catalytic behavior of Fe and/or Ru supported on activated carbon in methanol decomposition to CO and methane (49). This group have also studied the catalytic behaviour of nanosized iron and mixed iron-cobalt oxides supported on activated carbon materials in methanol decomposition to H2. Some research groups have prepared supported Wacker-type catalysts by impregnation of the acti- vated carbon support with KOAc promoter and CuCl2 or PdCl2/CuCl2 showing a higher performance in the gas-phase oxidative carbonylation of methanol for the dimethyl carbonate synthesis (DMC) (Fig. Deffernez et al. have also oxidized in liquid-phase carbohydrates and alcohols using gold acti- vated carbon catalysts (45). Last Decade of Research on Activated Carbons 331 and Carrettin et al. Pratti et al. have reported the oxidation of glucose to obtain sodium gluconate by Bi promoted Pd/AC catalysts (46).. have oxidized in liquid-phase carbohydrates and aldehydes to the corresponding carboxylic acids with O2 under mild conditions using Au/AC catalysts without loss of activity on recycling (43). CuO/MnO/AC. . CuCl2/ PdCl2 and CuCl2/PdCl2/KOH supported on activated carbon (55–58).48). Comotti et al. Diethyl carbonate (DEC) is a promising oxygenated organic additive for gasoline and diesel fuel to reduce pollutant emissions. have used Au/AC catalysts for the selective liquid phase oxidation of ethylene glycol to glycolate (42). 2) (60–62). Ma et al. Many research groups have readily prepared diethyl carbonate from the oxidative carbonylation of ethanol in gas phase with high selectivity using Wacker-type catalysts. Dimethyl carbonate (DMC) is a unique molecule having a versatile reactivity being very useful for environmentally benign reactions. Re-Cu/AC and Re-Mn/AC have been studied 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. Paneva et al. and Korovchenko et al. and platinum compounds on activated carbon (47.64) 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). CO. have investigated the oxidation of alcohols to the corresponding aldehydes and carboxylic acids with air in the presence of catalytic amount of transition metals such as copper. Hayashi et al.

The direct decomposition of methane shows a promising alternative to the traditional hydrogen production methods such as steam methane reforming (SMR) and partial oxidation of methane (POM) because there is no further byproduct except carbon.. easily obtained from various raw materials and the textural properties and surface structure can be easily controlled in the manufacture process. have reported the oxygen-assisted decomposi- tion of methane over AC-supported iron catalysts experimenting over wide range of temperatures and O2/CH4 ratios (75). such as alcohols or aldehydes. More recently. Presently. Wacker-type catalysts as for example Pd-Cu/AC catalysts were tested in the catalytic oxidation and chemisorption of CO for smoke applications (73). most of the industrial hydrogen production is based on steam methane reforming (SMR) process. which is of particular interest for the synthesis of valuable oxygenated chemicals.78). Calvino-Casilda et al. New routes to hydrogen production from natural gas (or methane) with drastically reduced CO2 emissions have been investigated. have prepared supported gold catalysts on activated carbon for low-temperature oxidation of CO and H2 (76) and some other authors have investigated the CO selective 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 be used as a source of energy for stationary power plants. ethers. An advantage of producing syngas by this route instead of processes like steam reforming or partial oxidation is the low H2/CO ratio obtained. and ester-alcohols mix- tures. Cui et al. Pt-SnOx/AC and Pt-CeOx catalysts supported on un-oxidized and oxidized activated carbon (AC) have been employed in the selective CO oxidation in H2-rich gas streams containing CO2 and H2O simulating the reformate coming from fuel processors (70). Non-noble metal catalysts have also been employed in this reac- tion such as Ni. have used gold activated carbon catalysts in the vapor phase carbonylation of lower aliphatic alcohols. The solid supported catalyst includes an effective amount of gold asso- ciated with activated carbon in the presence of a halide promoter (69). Muradov et al. which is a source of significant CO2 emis- sions into the atmosphere. . Zoeller et al. to produce carboxylic acid. have reported the dimethyl carbonate synth- esis over catalysts prepared loading KI and K2CO3 on activated carbon (68). esters and mixtures thereof. moving vehicles and fuel cell applications (77. esters. methanol. Polymetals (Cu. and desirably. 332 V. Activated carbon has been suggested as a good support for metal catalyst for COx-free hydrogen production by methane decomposition because AC is relatively stable. Okumura et al. deposited on the activated carbon in the oxidative carbonylation of methanol for dimethyl carbonate (DMC) synthesis using vapour phase flow reactor system (65–67). Cr and Ag) supported on Downloaded At: 18:30 25 January 2011 activated carbon were used in the catalytic oxidation of carbon monoxide in a fixed bed reactor (72). non-toxic as itself. which makes it more favourable to be a catalyst support. Pt/AC and Pt-Sn/AC catalysts have also been employed in CO oxidation (74). Co and Co-Ni/AC (71).

cupper and cobalt acetylacetonate complexes inmobilized on activated carbon at room temperature and atmospheric pressure. have reported the catalytic oxidation of hydrogen sulphide over activated carbon impregnated with Na2CO3 (95) and Ma et al. Numerous supported catalysts have been proposed for methane reforming. have investigated the catalytic oxidation of SO2 from incineration flue gas over Cu/AC and bimetallic Cu-Ce/AC catalysts and they have also carried out the simultaneous catalytic oxidation of sulfur dioxide/hydrogen chloride from incineration flue gas over activated carbon- supported copper. Hui-Hsin Tseng et al. Radkevich et al.80). Downloaded At: 18:30 25 January 2011 Kishi et al. Last Decade of Research on Activated Carbons 333 The preparation of metal supported activated carbon with Ni can catalyze the decomposition of methane and ethylene forming carbon nanofibers (CNFs) under relatively mild conditions (79. The residual H2S quickly reacts with the strong base and is immobilized (97–99). have carried out the electrochemical desulphurisation reaction over CeO2/AC catalysts (94). In 1998 Wang et al. The Pd/AC and Pt/AC catalysts were found to be oxidation catalysts at high temperature for hydrogen sulphide oxidation and methane oxidation (90). have reported the oxidation of cycloalkanes such as pinane using transition metal. However the shortcoming in the applications of caustic impregnated carbon is the fact that . Pd(OAc)2 supported on activated carbon combined with molybdovanadophosphate (NPMoV) (86). Dalai et al. have reported the selective oxidation of cycloalkanes using activated carbon supported iron-phtalocyanine catalysts (83–85). potassium iodide and potassium carbonate for hydrogen sulphide oxidation (91). have also reported activated carbon supported catalysts impregnated with ammonium iodide. (87). have studied the influence of surface functionalization of activated carbon on palladium dispersion in the preparation of 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). This group and also Langhendries et al. Valente et al. have carried out the oxidation of cycloalkenes such as cyclopentene under oxygen atmosphere using a Wacker type catalysts. the catalytic oxidation reaction for purifying H2S and PH3 contained in tail gas over activated carbon impregnated with Na2CO3 and also with HCl (96). proposed Ni/AC catalyst to develop this reaction and now Diaz et al. Wang et al. But the reforming of methane with carbon dioxide to synthesis gas has recently attracted renewed interest. have reached representative methane conversions at mild experimental conditions using Ni-Ca/AC catalysts where Ca plays a cosupport role inhibiting the deactivation of catalyst during long periods of reaction (81. iron or vanadium oxide catalysts and this group have also carried out (88. The oxidation of terpenes such as limonene over activated carbon anchored transition metal Schiff base complexes catalysts is reported by Oliveira et al.89). Some other authors have studied the catalytic oxidation of sulphur contain- ing compounds. Activated carbons impregnated with caustic materials (NaOH or KOH) have been used for removal H2S in sewage treatment plants.82). Xiao et al.

3. the activity of caustic carbons in H2S oxidation is worn out when caustic is consumed and the carbon pores are blocked by sulfur and sodium or potassium salts. nitro groups. Sun et al. saturation of unsaturated hydrocarbon com- pounds (e. con- densed ring aromatics etc. The classical hetero- geneous catalysts for carbon-carbon multiple bond hydrogenation involves sup- ported precious metals. . carboxylic acids. Catalysts are commonly used for the hydrogenation of alkenes. have reported the degradation and mineralization of the non- biodegradable azo dye Orange II making use of a Fenton-like oxidation process over a Fe/AC catalyst (100). metals such as chlrorine (hydrodechlorination. Hydrocracking. Hydrogenation. esters. have prepared CuFe2O4/AC catalysts for the removal of acid Orange II which combined the magnetic and the excellent catalytic properties of powdered CuFe2O4 (101). aromatics. 2. 334 V. have studied the catalytic performance of activated carbon supported tungsten carbide for hydra- zine decomposition (102). A wealth of processes and applications in the pharmaceutical.g. Removal of hetero-atoms and impurities from hydrocarbon streams.). nitriles. (b) Upgrading (decreasing boiling point range) of residue. The selective hydrogenation of carbon-carbon double and triple bonds is one of the fundamental reactions for the synthesis and manufacture of fine and indus- trial chemicals. (a) Stabilizing distillate fuels like gasoline. jet fuel by preventing sediment formation. Zhang et al. CATALYTIC REDUCTIONS (TABLE 2) Downloaded At: 18:30 25 January 2011 Hydroprocessing is a group of technologies where catalytic reactions take place in presence of hydrogen at elevated pressure to fulfil some or all of the following major objectives: 1. impregnation decreases the ignition temperature of the carbon and poses a risk of self-ignition. sulfur. olefins and aromatics). HDC). nitrogen.g. alkynes. Cracking of heavier hydrocarbon molecules to lighter ones for production of desired fuels and lubes. Increase H/C. In addition. activated base metal catalysts and Ni supported on oxides all being able to activate hydrogen under mild reaction conditions. Ramirez et al. hydrodenitro- genation (HDN). aldehydes. hydrodesulphurization (HDS). Calvino-Casilda et al. and imines. agrochemical and petrochemical industries is based on catalytic hydrogenation of unsaturated hydrocarbons by heterogeneous catalysts. (e. Hydrotreating.

Hydrogenolysis ! ! ! ! ! ! ! .CO2 hydrogenation ! ! .Hydrogenation ! ! ! ! of ketones 335 .Hydrogenation ! ! ! ! of carboxylic acid derivatives . Alkali Precious Alkali earths Transition metals metals metals metals Others Catalytic reductions Pd Pt Ir Ru Rh Ag Au Li Na K Rb Cs Mg Ba V Cr Mn Fe Co Ni Cu Zn Mo W Re Al Sn Pb P Ce Ge .Hydrogenation ! ! ! ! ! of esters .Hydrodehalogenation ! ! ! ! ! ! ! ! ! ! ! ! ! ! ! .Hydrodenitrogenation ! ! ! ! ! ! ! .CO hydrogenation ! ! ! .NOx reduction ! ! ! ! ! ! ! ! ! ! ! ! ! .Hydrogenation ! ! ! ! ! ! of alkenes/ cycloalkenes .Hydrogenation ! of azides .Hydrodesulphurisation ! ! ! ! ! ! ! ! ! .Hydrogenation ! ! ! ! ! ! ! ! ! ! ! of aldehydes .Hydrogenation of nitro ! ! ! compounds .Hydrogenation ! ! of terpenes . non-metal and their compound catalysts in the last decade. Downloaded At: 18:30 25 January 2011 Table 2: Main reduction reactions catalysed by activated carbon supported metal.CO2 reduction ! ! .Reductive amination ! .Hydrogenation ! of alkynes .Methanol ! ! ! ! ! ! ! ! decomposition .Hydrogenation of ! carbohydrates .Hydrogenation ! ! ! ! of aromatic rings .

have carried out a reaction of great industrial interest such as the semihydrogenation of phenylacetylene in liquid phase over Pd/AC catalysts (115). in aqueous phase and in vapour phase to explore a possible way for the treatment of phenolic wastewaters and to obtain intermediates for the fragance and pharmaceutical industry (Fig. used in formulation of cosmetics and with important applications in the manufacture of chemical compounds (113.114). halides. 3) (120–123). Ru/Ac catalysts have been tested on benzene and toluene hydrogenation (119) and Pd/AC catalysts have been developed for the hydrogenation of phenol to cyclohexanols or cyclohexanone. Matos et al. have developed a diphenyl sulphide inmobilized on Pd/AC system for chemoselective hydrogenation of alkenes. carboxylic acids. Recently Mori et al. Wolfson et al. and manufacture. Ru. Perez-Cadenas OH O OH H2 H2 H2 Figure 3: Reaction paths in phenol hydrogenation over activated carbon supported catalysts. Calvino-Casilda et al. have reported Ni/AC and Ni-Mo/AC catalysts for the hydro- genation of simple insaturated hydrocarbons such as ethylene (103–105). have prepared Pd and Pt/AC catalysts for gas-phase hydrogenation of styrene oxide to produce 2-phenylethanol. Downloaded At: 18:30 25 January 2011 and nitro groups in presence of aromatic ketones. Kirm et al. These compounds are useful building blocks for the synthesis of biologically active compounds and natural products. Pd. Hiyoshi et al. Esters. the aromatic ring hydrogenation requires more severe conditions than the hydrogenation of other functional groups and highly homogeneous catalytic systems have disadvantages concerning stability. productivity. have reported the hydrogenation of naphthalene in supercritical carbon dioxide solvent over Rh/AC catalysts (124). and Rh) and nickel supported-activated carbon catalysts (125–130).118). have been tested on hydrogenation of alkenes and cycloalkenes (106–112). Pt-Sn and Pt/AC catalysts have been tested on benzene hydroge- nation to cyclohexane (117. 336 V. these materials have commenced to be repleaced by activated carbons during the last decades. azides. In general. Precious metals supported-activated carbon catalysts such as Pd. Domínguez- Domínguez et al. acetylenes.. a compound with bacteriostatic and antifungic properties. and N- benzyloxycarbonyl groups (116). have reported the enantioselective hydrogenation of a β-ketoesters such as methyl acetoacetate to β-hydroxyesters over Ni/AC catalysts (131). . However. Pt. benzyl esters. Rh and Ir. and ketones can be reduced to their respective alco- hols using precious metals (Pt.

dyes. Some authors have investigated the reaction using precious metals supported-activated carbon catalysts such as Pd. have reported Pd/AC catalysts for the catalytic hydrogenation of p-nitrocumene to p-cumidine in a slurry reactor (147). (139). have reported the hydrogenation of perchlorate over Co-Pt/ AC. (145). Last Decade of Research on Activated Carbons 337 et al. have carried out the hydrogenation of α-oxophosphonates with molecular hydrogen over Pd/AC catalysts for the synthesis of α-hydroxyphosphonates (133). Serrano-Ruiz et al. and molybdophosphoric acid-V2O5/AC) (146). The selectivity to the desired products is still an important issue in the case of the industrial hydrogenation of cinnamaldehyde towards the clean production of the desired intermediates. have studied the catalytic activity in CO2 hydrogenation to methanol of activated carbon-supported Cu-ZnO catalysts (157) and Zhongrui Li et al. Vilella et al. (143. and pharmaceuticals. The reduction of carbon dioxide with water has been investigated for the direct synthesis of methane over Raney Fe- Ru/AC catalysts by Kudo et al. It has also reported that Pt/AC catalysts can convert primary amines into secondary amines in good yield. The hydrogenation of nitro compounds to the corresponding amines is a very important reaction. The hydrogenation of α. Ni-Pt/AC. have reported the hydrogenation of sugars such as fructose on Ru/AC catalysts and De Miguel et al. . (160). Activated carbon supported platinum catalysts have been employed in the hidrogenation of ortho-nitrochlorobenzene to 2. Gulyukina et al. have reported the hydrogenation of fatty acid methyl esters (vegetable oils) on palladium catalysts supported on carbon-coated monoliths (132). Pt.. Guerrero et al. and Silvestre et al. Heinen et al.149). via retro-reductive and reductive amination upon microwave irradiation in water (151).20 -Dichloro-hydrazobenzene and in the hydrogenation of nitrobenzene (148. The hydrogenation of cinnamaldehyde has been attracting increasing interest due to the importance of the derivatives in the fine chemicals industry. (141.144). and Ru (134–136).142). (138).and Co-Mo-K/AC catalysts via CO hydrogenation (158. 4) (153–156). PtSn/AC and PtGe/AC. W-Pt/AC and Pt/AC catalysts (152). (140). have studied the effect of the activated carbon support in Pt and PtSn catalysts used for selective hydrogenation of terpenes such as carvone (Fig. Sakata et al. Mahmudov et al. Cu/AC.C. Thomson et al.β-unsaturated aldehydes such as crotonaldehyde and citral over activated carbon-supported metal catalysts (Pt-Zn/AC Coloma et al. Others authors have studied the hydrogenation of α. rubber chemicals. J. have reported the mixed alcohol synthesis over Mo-K. Jaganathan et al. Downloaded At: 18:30 25 January 2011 MoC/AC. Pt/AC. (137). Dandekar et al.159).β-unsaturated aromatic aldehydes is accompanied by the formation of several by-products. Bachiller-Baeza et al. as these chemicals are used as basic raw materials for urethanes. On the other hand. activated carbon supported nickel catalyst have been used in the hydrogenation of p-chloronitrobenzene to p-chloroaniline (150). Ru and Ru-Fe/AC.

and Pt-Co) supported-activated carbon catalysts have been used in the hydrodechlorination of CFC-12 and CFC-13 (175–179). nickel-copper (NiCu/AC) and nickel-aluminium oxide (NiAl/AC) catalysts for the hydrogenolysis of halogenated chlorofluorocarbons (CFC-12) (180). Catalytic hydrodechlorination (HDC) has emerged as a promising non-destructive technology not only for the safe conversion of chlorinated waste.and Ru/AC catalysts in the catalytic transfer hydrogenolysis of 2-phenyl-2- propanol over Pd/AC catalysts. Calvo et al. Catalysts employed for HDC reaction are often susceptible for deactivation. There are also many studies using other noble metal supported-activated carbon catalysts. In particular. supported palladium is the most widely used catalyst for this reac- tion. which is responsible for the depletion of the ozone layer. but also producing value-added products. The selective hydrogenolysis of CFCs such as CCl2F2 (CFC-12) into CH2F2 (HFC-32) and CFC-115 into HFC-15 over Pd/AC catalysts have been studied by many authors (108. In this context. Calvino-Casilda et al. A closely related reaction to hydrogenation is hydrogenolysis where a molecule of hydrogen is added over a carbon-carbon single bond. Pt-Fe. Markus et al. Downloaded At: 18:30 25 January 2011 Chlorofluorocarbons (CFCs) have had a lasting effect on the environment. the development of a poison-resistant catalyst has gained significant importance in recent years. Morato et al. to an antic- arcinogenic and antioxidative compound using Pd/AC catalysts (161–163). Ru. which are influenced by several factors such as the method of preparation. have carried out the hydrogenolysis of a wood extractive. nickel- potassium oxide (NiK/AC). have prepared activated-carbon-supported nickel (Ni/AC). and bynary metal mixtures (Pt-Cu. CHO O O + Figure 4: Reaction scheme of the catalyzed carvone hydrogenation. They are a major source of stratospheric chlorine. the mean particle size. effectively causing a “lysis” of the bond. have carried out the hydrodechlorination of Alachlor . Pt-Ag. but only a few studies in the last decade have dealt with the hydrogenolysis reaction of chlorofluorocarbons. 338 V. Rh. and the nature of precursor salt used in the preparation of catalysts. The hydrodechlorination activity depends on the nature of active sites. Pd. Ir. Noble metals have mainly been used as catalysts in the hydrodechlorination reaction of CFCs.164–173). Ru/AC catalysts were tested on the hydrogenolysis of n-hexane and Pt-. Pd. Pt. There are also authors who have investigated non-noble metals supported- activated carbon catalysts such as Ni/AC. These catalysts have shown similar catalytic behaviour to the noble catalysts. the natural ocurring lignan hydroxymatairesinol. and Re/AC catalysts. due to strong adsorption of HCl produced as a by-product.

A gaseous or liquid reductant (most commonly ammonia or urea) is added to a stream of flue or exhaust gas and is absorbed onto a catalyst. Fe-Mo/AC. organic matter and toxicity of the water dis- charges of this industry. The reductant reacts with NOx in the exhaust gas to form harmless H2O and N2. have carried out the hydrogen-assisted 1. Fe. Ni-Mo/AC and sulfided metals such as Ni-Mo/AC have been employed as catalysts in hydrotreatment processes by other authors (197–204). Pinto et al. Ni-Re/AC. Other supported-activated carbon containing metal. (187). or a catalyst with zeolites in the washcoat. have prepared vanadium nanoparticles supported on activated carbon catalysts for tiophene hydrodesulphurization (206) and Park et al. Dhandapani et al. have reported V2O5/AC catalysts in simultaneous sulfur dioxide and nitric oxide removal from flue gas (209). Re/AC. and a catalyst. Pt and Pd supported-activated carbon catalysts (187–191). have used the reactivity of molybdenum carbide sup- ported on activated carbon with phosphorous additive as catalysts for hydro- processing reactions such as hydrogenation. Calvo et al. . Last Decade of Research on Activated Carbons 339 in water using Pd.1. Xing et al. Santoro et al. Downloaded At: 18:30 25 January 2011 The Pt/AC catalysts have been prepared for the hydrodechlorination of aliphatic organochlorinated compounds that are released into the environment in the greatest amounts (dichloromethane. chloroform. have employed Pt-Cu/AC and Pd-Cu/AC catalysts (192).3-trichloropropane dechlorination on Pt-Sn/AC catalysts (195). trichloroethylene and tetrachloroethylene) (193.2. the synthesis of ZnO/AC catalyst for the effective removal of a very low concentration of sulfur compounds contained in a gasified fuel gas (207). have employed V2O5-CoO/AC catalysts for flue gas SO2 removal and elemental sulfur production (208) and Guo et al. Early et al. Ni and Cu/AC catalysts (181) and Keane et al. W. Catalytic hydrodechlorination is proposed as an interesting alternative/complement for the elimination of chlorinated organics from bleaching effluents. Selective catalytic reduction (SCR) of NOx is a tecnhology to remove nitrogen oxides. hydrodesulfurization (HDS) and hydrodenitrogenation (HDN) using model liquid compounds (196). 1. through a chemical reaction between the exhaust gases. Ni-Mo. have employed Pd/AC catalysts for the hydrodechlorination of chlorophenols with the aim of reducing the toxicity of a type of wastewaters (183–185). binary metal mixtures such as CoMo/AC. Water pollution is a major concern for the pulp and paper industry due to the large quantities of effluents generated.194). (186) and Keane et al. The effluents from pulp bleaching are responsible for most of the colour.1-trichlorethane. the current options being a vanadium-based catalyst. More recently. a reductant additive. the most abundant and polluting component in exhaust gases. containing nitrates Barrabes et al. have studied the hydrodechlorination of chlorobenzene over Ni/AC catalysts (182). carbon tetrachloride. have carried out the hydro- dechlorination (HDC) of chlorobenzene over Ni and Fe/AC catalysts and other authors over Ni. NiMo(W) and PNiMo(W)/AC. In the study of catalytic reduction of contaminated waters. Special catalytic converters are required to make an SCR system work.

Pb and V (232–236) and improving the active phase distribution. an enhancement of the activity for NOx reduc- tion was required through a proper modification of the carbon characteristics and the use of active phase. the interaction takes place through the intermediate phenomenon of the acoustic cavitation. From the point of view of fine chemicals synthesis. relatively few Downloaded At: 18:30 25 January 2011 studies had been focused on catalysis by bases until last decade. Pt (213–216). have synthesized α. the sonication presents beneficial effects on the chemical reactivity. La (217–222). base catalysts have played a decisive role in a number of reactions mainly for fine-chemical synthesis. which bombard the solid surface. V (227–231) and binary mixtures. In general. Fe. environmentally benign and more economical pathways are advantages that have caused a remarkably increase in this research field (237). and solvents are some of the many advantages presented by solid-base catalysts. increasing surface area and porosity. For that reason in the last decade many authors have worked on improving their catalytic activity by optimisation of char preparation. Ni. during this period. Ni (223–226). The cavitation effects form microjects of solvent. This fact causes the exposition of unreacted surfaces of solid. Martín-Aranda et al.β-unsaturated nitriles by sonochemical activated reactions of carbonylic compounds with malononitrile using two basic carbons (Naþ– and Csþ–Norit) as catalysts. Martín- Aranda and coworkers have reported the use of basic solids such as alkali-doped activated carbons to catalyze selectively several reactions (238–245). BASIC-CATALYZED REACTIONS (TABLE 3) Although catalysis by solid acids had always received much attention due to its importance in petroleum refining and petrochemical processes. such as K.There is not before any report for the use of activated carbons as catalysts in combination with ultrasounds. catalysts. heterogeneous catalysts are considered as an eco-friendly alternative. Easier separation and recovery of the products. Cu. Mg. which offer the hope of providing the chemist with innovative synthetic routes as sonochemical and microwave activated reactions. Previous studies on supported-activated carbon catalysts exhibit low catalytic activity for NOx reduction. increasing the interphase surface able . K (210–212) . loading of some metals and its oxides. Calvino-Casilda et al. Fe. When one of the phases is a solid. Mn. However. Co. In this respect. Hence. Ce. A substantial enhancing effect in yields and selectivities was observed by this group when the carbon catalyst was activated under ultrasonic waves. the ultrasonic irradiation has several additional enhance- ment effects especially when the solid acts as catalyst. such as reaction accelera- tion. Co. The sonochem- ical phenomena originate from the interaction between a suitable field of acous- tic waves and a potentially reacting chemical system. such as Na. and to enhance the catalyst efficiency. Ba. 340 V. Cu. Recent years have seen the development of a number of new technologies. to reduce the induction period.

and C-Alkylations ! ! ! ! ! .Aziridination of olefins ! .Enaminones synthesis ! ! .Ethers synthesis ! ! .β-Unsaturated nitriles ! ! .Darkin-West reaction ! ! Basic-catalyzed reactions . Precious metals Alkali metals Transition metals Others Ru Li Na K Cs Mn Fe Cu W P Si N Acid-catalyzed reactions .Acylation of alcohols and amines ! ! ! 341 .Esters synthesis ! ! .Acetals and ketals synthesis ! ! .Claisen–Schmidt condensation ! ! .N.Alkene epoxidation ! .Synthesis of α. non-metal or their compound as catalysts in the last decade. Downloaded At: 18:30 25 January 2011 Table 3: Main acid.and base-catalysed reactions using activated carbon supported metal.

to react. Calvino-Casilda et al. In their studies. for the produc- tion of other fine chemicals due to the mild conditions that this method offers. .and Cs-Norit or their binary combinations have been tested in the N-alkylation of imidazolic rings with medium-chain and long-chain alkyl halides activated by ultrasounds or under conventional thermal activation (Fig. 5) (239). Chalcones are important intermediates in the synthesis of many pharmaceuti- cals and they are commonly synthesized via the Claisen–Schmidt condensation between acetophenone and benzaldehyde (Fig. Enhancement effect on the reaction rate by combining the basicity of the carbon with ultrasounds is also presented as an alternative method for the production of differently substituted chalcones and. in general. 6) and in the N- propargylation of imidazole activated by microwaves and conventional thermal Downloaded At: 18:30 25 January 2011 activation. Basic carbons such as Na-. they demonstrate how this fact can be used to reduce the reaction temperature and how the selectivity is modified (240–245). N N basic carbon + Br N N H Figure 6: N-alkylation of imidazole with 1-bromobutane. (238). which means that it is a very efficient absorber of microwave energy and converts that energy to heat. Carbon is known in microwave terminology as a very “lossy” material. which are key intermediates in the synthesis of pharmaceutically impor- tant anticonvulsants and bactericidal products. K. O O O O Carvone Carvomenthone Carvotanacetone Dihydrocarvone OH OH OH OH Carveol Carvotanalcohol Dihydrocarveol Carvomenthol Figure 5: Preparation of chalcones by Claisen-Schmidt condensation. 342 V. They have also reported the catalytic selective synthesis of N-alkylated imi- dazoles.

etc. they can be easily transformed into a large variety of compounds by means of regioselective ring opening reactions (248). NaHCO3/AC) (246). as very efficient catalysts in the asymmetric epoxida- tion of unfunctionalised alkenes (247). generally known in the literature as manganese(III) salen complexes. The chiral manganese (III) Schiff base complexes with a N2O2 coordination sphere. Conversion of low cost feedstocks such as used frying oils is complicated if the oils contain large amounts of free fatty acids that will form soaps with alkaline catalysts. have reported the catalytic synthesis of dipropyl carbonate from the transesterification of dimethyl carbonate and propyl alcohol over K2CO3/AC catalysts that show better catalytic activity than other base catalysts used in Downloaded At: 18:30 25 January 2011 this type of reaction (249). acid catalysis is continuously in expansion and trying to improve the reaction conditions according to the increasing interest of getting environmentally friendly processes. The aziridination of alkenes is a reaction of great importance since aziridines are used as intermediates in organic synthesis for pharmaceuticals and agrochem- icals. Ketones and aldehydes can react with excess alcohol in acid medium to give ketals and acetals. have reported the synthesis of acetals and ketals catalyzed by tungstosilicic acid supported on activated carbon. have been reported by Silva et al. to prepare iron (III) oxide-containing activated carbon catalyst (250). The importance of this system is due to its practical use in laboratory and industry scale and to the broad use of epoxides as intermediates in organic synthesis. Activated carbon has been found to be able to entrap a certain amount of heteropoly acids by equilibrium impregnation with water solvent (252). So for example the need to develop a reusable and economic solid acid catalyst for the selective acylation of alcohols and amines employing carboxylic acids as acylating agents to achieve high atom economy. Fan et al. Yang et al. have driven to Sreedhar et al. ACID-CATALYZED REACTIONS (TABLE 3) Though last decade is the decade for base catalysis. Last Decade of Research on Activated Carbons 343 Wang et al. Acetals and ketals are among the most important perfume materials and industrial materials of organic synthesis. Heteropoliacids and their salts have interesting catalytic prop- erties for fine chemicals industries. have reported the catalytic synthesis of propionitrile from alkyla- tion of acetonitrile by addition of methanol as a carbon source over activated carbon- supported alkali catalysts (LiNO3/AC. The soaps can prevent separation of the biodiesel . KNO3/AC. Silva et al. and pharmaceutical and food and flavors indus- tries. respectively. NaNO3/AC. have reported the catalytic activity of copper (II) acetylacetonate complexes anchored onto an activated carbon in the aziridination of styrene using nitrene reagents (PhI ¼ NTs) as nitrogen source at room temperature (251). Vegetable oils and animal fats can be transesterified to biodiesel for use as an alternative diesel fuel. CsNO3/AC and Ch3COONa/AC.

in the synthesis of tert-amyl ethyl ether (257).2-epoxyhexane and styrene oxide) ring-opening reaction with 1-butanol (Fig. –CH2CH2CH2CH3 Figure 7: Epoxides ring opening reaction with 1-butanol. Juan et al. CATALYTIC C—C BOND FORMATION (TABLES 4A AND 4B) There are several practical reactions to be applied to cost-effective large-scale production of multifunctional intermediates for drug-synthesis such as Suzuki. . Epoxide ring-opening reactions are useful tools in organic chemistry. and thiazolines in dry media (254). the alcohol acylation (etherification) and the epoxide-opening (266). Lin et al. Calvino-Casilda et al. O O OH + R OH R R = –Ph. Sulfonated activated carbon catalysts have been employed in different organic reactions such as the selective hydrolysis of cellulose into glucose (265).. Zhou et al. have reported heteropolyacid supported on activated carbon by vaporization for the catalytic synthesis of aliphatic acetate by esterification of acetic acid with various alcohols obtaining high yields (261). and Ullmann reaction. imidazolines. have supported phosphotungstic acid on activated carbon to prepare catalysts for the synthesis of dibutyl sebacate (259). have prepared 12-tungstophosphoric acid (TPA) impregnated on activated carbon for the biodiesel production from low quality canola oil containing up to 20 wt% free fatty acids (253). have studied the catalytic activity of tungstophosphoric acid supported on activated carbon in the synthesis of enaminones and in Dakin- West reaction for the production of β-acetamido ketones (255. have reported the catalytic synthesis of n-dibutyl adipate by activated carbon supported tungstophosphoric acid (258) and Liu et al. have also prepared 12-Tungstophosphoric acid (TPA)/AC catalysts for the synthesis of oxazolines. 344 V. have investigated the epoxides (1. Sonogashira.256) and Obali et al. 7) and more recently with ethanol under microwave irradiation using activated carbons treated with mineral acids (HNO3 and sulfonitric mixture) as acid catalysts (263. Kulkami et al.264). from the glycerin fraction. Durán-Valle et al. have investigated SiW12/AC catalysts prepared loading silico- Downloaded At: 18:30 25 January 2011 tungstic acid on activated carbon for the synthesis of trioxane (260). Shi et al. Rafiee et al. Reactions of epoxides are key processes for the transformation of aliphatic and aromatic compounds. Heck. Mohammadpoor- Baltork et al. have investigated the esterification of oleic acid by n-butanol over zirconium sulfate suported on activated carbon catalysts (262).

Downloaded At: 18:30 25 January 2011 Table 4: Main catalytic reactions of C—C bond formation and other applications using activated carbon supported metal. non metal and their compound catalysts in the last decade (Table 4A and Table 4B). Precious metals Alkali/ Alkali earths metals Table 4A Pd Pt Ir Ru Rh Au Ag Na K Rb Cs Ba Mg Ca Catalytic C–C bond formation Carbonylation of methanol/aliphatic alcohols/ethers/esters/ R-X ! ! ! Hydroformylation ! Heck reaction ! Suzuki and Miyaura reaction ! Ullmann reaction ! Fukuyama reaction ! Sonogashira reaction ! Knoevenagel condensation ! ! Reductive coupling of haloaryls ! ! Markovnikov addition ! Other applications 345 Dehydrohalogenation (β-Elimination reaction) ! Dehydrogenation of alkanes/cycloalkanes (production of H2) ! ! ! Dehydrogenation of alcohols ! Cyanosylilation of aldehydes Isomerization of polyunsaturated fatty acids ! ! ! ! ! 1-butene isomerization Catalyst-anode for fuel cell ! ! ! Ozonation Polymerization of cycloalkenes Oligomerization of hydrocarbons ! Denitrification of water (DeNOx) ! ! Photocatalyst Hydrosilylation of alkenes ! Fischer-Tropsch synthesis ! Ammonia synthesis ! ! ! Ammonia decomposition ! CF3I synthesis ! ! ! ! Oil yield (coal extraction) Antibacterial activity ! ! ! Glycerol dehydration .

Sonogashira reaction . Downloaded At: 18:30 25 January 2011 Table 5: Transition metals Others Table 4B Ti V Mn Fe Co Ni Mo W Re Os Bi Cu Zn Sn Ce Zr La Cr Si Catalytic C–C bond formation .Heck reaction .Reductive coupling of haloaryls .Knoevenagel condensation .Carbonylation of methanol/aliphatic alcohols/ethers/ ! ! esters/ R-X .Hydroformylation .Fukuyama reaction .Suzuki and Miyaura reaction ! .Ullmann reaction .Markovnikov addition Other applications Dehydrohalogenation (β-Elimination reaction) ! Dehydrogenation of alkanes/cycloalkanes (production ! ! ! ! ! 346 of H2) Dehydrogenation of alcohols ! ! ! Cyanosylilation of aldehydes ! Isomerization of polyunsaturated fatty acids ! ! 1-butene isomerization ! Catalyst-anode for fuel cell ! ! ! Ozonation ! ! ! ! ! ! Polymerization of cycloalkenes ! ! ! Oligomerization of hydrocarbons ! Denitrification of water (DeNOx) ! ! Photocatalyst ! ! ! Hydrosilylation of alkenes ! Fischer-Tropsch synthesis ! ! ! ! ! ! Ammonia synthesis ! ! Ammonia decomposition CF3I synthesis Oil yield (coal extraction) ! ! ! Antibacterial activity ! ! ! ! Glycerol dehydration ! ! .

Last Decade of Research on Activated Carbons 347 The Suzuki reaction (or Suzuki-Miyaura reaction) is the organic reaction of an aryl. or vinyl compound and the alkene contains at least one proton and is often electron-deficient such as acrylate ester or an acrylonitrile. carbon Br Pd/C. potassium carbonate. and reactivity pattern. In organic synthesis. a coupling reaction of terminal alkynes with aryl or vinyl halides. Ullmann reaction is less typical. The ligand is triphenylphosphine or BINAP (2. have been carried out over palladium complexes and palladium on activated carbon catalysts. 140 ºC R -HBr R E.or vinyl-boronic acid with an aryl. Sonogashira reaction. Several reviews have been published using different palladium supported catalysts such as palladium nanoparticles supported on activated carbon (267–269). Several Downloaded At: 18:30 25 January 2011 investigations are reported in literature about the Heck reaction catalyzed by palladium-supported activated carbon catalysts (Fig. have reported the coupling of substituted haloben- zenes to the respective biphenyls using a combination of a reducing agent and a weak base (Na2CO3) in the presence of catalytic tetrabutylammonium bromide (TBAB) and palladium that are both supported on activated carbon. . or sodium acetate. palladium chloride or palladium acetate.1’-binaphthyl). For example. and it is often replaced by Heck reaction and Sonogashira coupling (276.The catalysts employed have been tetrakis(triphenyl- phosphine)palladium.277). and sub- stituted biphenyls. The results are explained with postulation of a physical micro-membrane formed in situ by the phase-transfer catalyst (278). Ullmann reaction is a coupling reaction between aryl halides and Fukuyama reaction is a palladium catalysed coupling of organozinc compounds with thioesters to form ketones. It is widely used to synthesize poly-olefins. The Heck reaction is the chemical reaction of an unsaturated halide with an alkene and a strong base and palladium catalyst to form a substituted alkene. The base is triethylamine. 8) (270–275). benzyl.2’-bis(diphenylphosphino)-1. COCH3 Figure 8: Heck coupling of bromoarenes with styrene catalyzed by Pd supported activated carbon catalysts. The halide or triflate is an aryl. styrenes. Due to the availability. OCH3. Mukhopadhyay et al. Other catalysed C–C coupling organic reactions besides Heck reaction.and Z-isomers R R = H. Carbonylation reactions are of major importance in both organic and indus- trial chemistry. base + + solvent. price.or vinyl-halide catalyzed by a palla- dium catalyst.

which have expanding practical applications as pharmaceuticals in the line of calcium channel blockers (Fig. There is another type of reaction catalysed by alkali solid catalysts and reported by Calvino-Casilda et al.. alcohols. The reaction products are precursors in the production of 1.4- dihydropyridine derivatives. etc. the catalytic ammonia synthesis has grown to be among the most important industrial processes. Merenov et al. Ruthenium is less inhibited by CHO R1 O COCH3 COOEt catalyst + COOEt R2 R1 R2 Figure 9: Knoevenagel condensation between substituted benzaldehydes and ethyl acetoacetate for the synthesis of benciliden derivatives in the production of 1. This reaction is an important industrial process for the production of aldehydes from alkenes. 348 V. R2¼H. Calvino-Casilda et al. have improved the selectivity in the catalytic carbonylation of 1. alkynes. They have reported the condensation of benzaldehyde and different substituted benzaldehydes with ethyl cyanoacetate using Na-Norit and Cs-Norit as catalysts in dry media. alkyl halides. Kosmambetova et al. . monoxide is becoming a more and more important building block for fine and bulk chemicals. H. the hydro- formylation (oxo synthesis) of long-chain alkenes over rhodium complex inmobi- lized on activated carbon. have reported the direct vapor-phase carbonylation of methanol on Ni/AC and NiCl2-CuCl2/AC catalysts obtaining a high selectivity to methyl acetate (283. amines. as -OMe. which has been used to measure the strength of the basis sites and can be used to form C–C bonds through the reaction of a carbonyl with an activated methylenic group. Some authors have studied the stability of Rh/AC and Ni/AC catalysts in the liquid-phase and vapour-phase carbonylation of methanol (280–282). NO2). It is important because the resulting aldehydes are easily converted into many secondary products (286–291).3-butadiene to 3- pentenoic acid immobilizing rhodium on activated carbon (279). OTHER REACTIONS (TABLES 4A AND 4B) During the 20th century. Downloaded At: 18:30 25 January 2011 Some authors have reported a variety of carbonylation reactions. have carried out the methane oxidative carbonylation catalyzed by rhodium chalcogen halides over activated carbon support (285). -OEt. Ru-based materials are the second- generation catalysts for ammonia synthesis.284).4-dihydropyridines (R1¼NO2. the Knoevenagel condensation.) into a substrate which may be of varied types such as alkenes. 9) (292). Carbonylation reactions involve the insertion of 4C¼O moiety with or without other groups (if any. nitro compounds or substituted aromatic analogs of these. and Peng et al. More recently. Protzmann et al.

Downloaded At: 18:30 25 January 2011 Vanadium and iron oxides. have reported Ru/AC catalysts for ammonia decomposition (302). Co and Fe-Co/AC catalysts were proposed by Rarog- Pilecka et al. ammonia. Co3O4. nitrate and nitrite. Ozone decomposition has been reported over metal oxide supported on activated carbon catalysts. Cu. MnO2. Nitrogen occurs in raw surface water in the form of organic nitrogen. CoO. The catalytic decomposition of ozone is an important area of research from environmental and health point of view. over Pt-Zn/AC catalysts obtaining high selectivity to isobutene (143. Pt. have recently reported the nitrate and CH3 H2C CH2 CH + H2 Ethylbenzene Styrene Figure 10: Ethylbenzene dehydrogenation to styrene. Cu-Pt. have carried out the dehydrogenation of iso-butane over Fe/AC catalysts and Silvestre et al. 10) (308–312). less sensitive to poisons.and PdSn/AC catalysts for nitrate reduction (317) and Soares et al. Ru-based activated carbon supported catalysts with promoters as barium and potassium have been reported by many authors to be active for ammonia synthesis (293–300). Cu2O. have reported the catalytic denitrification of water using metal-activated carbon supported catalysts.307). and NiO/AC by Heisig et al.303–306). The biological denitrification of water is a convenient and cost-effective alternative method for the removal of nitrate and nitrite ions from waters. Shimada et al. Pd/AC and Pt/AC catalysts have been employed on cyclohexane dehydrogenation and Pt/AC and Pt-Re/AC catalysts have been employed in the dehydrogenation of decalin in the hydrogen supply to fuel cells (108. Fe2O3. and more active than the traditional iron-based catalyst. Catalytic ammonia decomposition has attracted significant and increasing attention as a means of supplying pure hydrogen for fuel cells. which must be added to the water being treated. Last Decade of Research on Activated Carbons 349 ammonia. all of which are undesirable in drinking water. Fe. Co3O4. as catalysts for ammonia synthesis using barium and potassium promoters (301). . Pd. Rarog-Pilecka et al. and NiO supported on activated carbon catalysts were employed on dehydrogenation of alcohols such as cyclohexanol and isopropanol (313–315). Lemaignen et al. vanadium and magnesium and copper supported on activated carbon have been proposed as catalysts for ethylbenzene dehydrogena- tion to styrene a high value chemical (Fig. Most studies on denitrification by heterotrophic denitrifying bacteria have shown that the cultures require a carbon as an electron donor for the reduction of nitrate and nitrite. (316).

343). Sobana et al. For practical applica- tions there are some difficulties such as either filtration of fine TiO2 or fixation of catalyst particles and efficient utilization of UV/Solar light. Environmental photochemistry using semiconductors is the part of a general group of chemical remediation methods known as Advanced Oxidation Processes (AOPs). Chen et al. the photodegradation of reactive red dye (342. which acts as a shelter for bacteria from high fluid shear forces (319). Many authors have based their investigations on using TiO2/AC as catalyst. the photocatalytic degradation of atrazine (330). nitrite reduction in water over bimetallic catalysts Rh-Cu/AC and Pd-Cu/AC (318). Li et al. the decomposition of aqueous hydro- quinone (339). clay and activated carbon being this last the most commonly Downloaded At: 18:30 25 January 2011 used adsorbent for water treatment. have evaluated the degradation efficiency of ZnO loaded activated carbon catalysts (AC–ZnO composite photocatalyst) with solar light . These methods are based on one distinguishing feature—the generation and use of hydroxyl radicals as the primary oxidant for the degradation of organic pollutants. 350 V. Activated carbon has a large specific surface area and a well-developed porous structure. However. resulting in an attractive force toward organic molecules (320–328). ZnO is found to be a suitable alternative to TiO2. the photocatalytic degradation of toluene (331). the photocatalytic degradation of esters as ethyl hexanoate (335). zeolites. Parra et al. supported TiO2/TPPHS (2. For these reasons many researchers have been working to increase the efficiencies of this process by mod- ification of its surface. Hilal et al. Moreno-Castilla et al. have reported the photodegradation of L-acids under visible light over Mo-TiO2/AC catalysts and Follansbee et al. More recently. Calvino-Casilda et al. Geng et al. the photocatalytic removal of pesticide dichlorvos from indoor air (340) and Nada et al. Subramani et al. Wang et al. TiO2 is anchored or embedded onto support materials such as silica.4. Gauthier et al. the photocatalytic degradation of indigo carmine dye (332). the photocata- lytic degradation of methylene blue (333). have reviewed the preparation of titanium dioxide loaded onto activated carbon support and its photocatalytic activity in a variety of investigations as i.e. Sleiman et al. Under anaerobic conditions. the photocatalytic degradation of Rhodamine B (334). many bacteria use nitrate and nitrite ions contained in contaminated waters for respiration. Activated carbons offer the advan- tages of a large adsorptive capacity and an irregular shape. from water decontamination to direct pollutant degradation in aqueous and gas phase systems using UV irradiation and lately with the assistance of ultrasonic sound waves (345). Arana et al. some other authors the removal of phenol and phenol derivatives from water (336–338). TiO2 is reported to be a Benchmark photocatalyst. alumina.6-triphenyl hydrogen sulphate) onto activated carbon (AC) to yield a new class of catalytic system AC/TiO2/TPPHS for the photo-degradation of phenol and benzoic acid in water (344). have studied the photocatalytic hydrogen production (341). Puma et al. the gas-phase alcohols photocatalytic degradation (329). have studied the deni- trification of water under anaerobic conditions by using Escherichia coli supported or immobilised on different activated carbons.. Zou et al. Among the several semiconductors.

have synthe- sized fluorine-doped titania-coated activated carbon catalysts with photocatalytic activity in the degradation of phenol under visible light (349). The principal purpose of this process is to produce a synthetic petroleum substitute. Maruyama et al. PtRu/AC catalysts have been tested in the methanol electro-oxidation and as anode catalyst of the direct methanol fuel cell (DMFC) by some authors (359. The utility of hydrosilylation as a synthetic tool has even been extended into the area of enantioselective reactions. have found that platinum 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 reported the influence of lanthanum on the performance of Zr-Co/AC catalyst in this reaction (351). Xu et al.360). More recently. while oxygen is simultaneously reduced at the cathode. Last Decade of Research on Activated Carbons 351 at room temperature using an azo dye Direct blue 53 (DB53) and have also studied its photocatalytic activity on 4-acetylphenol degradation (346. The Fischer-Tropsch process is a catalyzed chemical reaction in which carbon monoxide and hydrogen are converted into liquid hydrocarbons of various forms.347). Typical catalysts used are based on iron and cobalt. have reported that aldehydes can react with trimethylsilyl cyanide under both thermal and catalytic conditions to give α-silyloxy nitriles which may be useful intermediates and protective groups in organic synthesis. have employed Pt/AC catalysts in fuel cell electrodes (355). Ominde et al. for use as synthetic lubrication oil or as synthetic fuel. typically from coal or natural gas. . Kerzenmacher et al. The only off-gas product of hydrogen fed fuel cell is water vapour. Some authors have proposed Fe-Co/AC.Baleizao et al. This trend of organome- tallic chemistry has prompted us to develop new methodologies for stereoselec- tive formation of silicon-carbon bonds. are oxidised at the anode of the fuel cell. such as hydrogen or methane.methyl)siloxanes in the synthesis of silicone waxes (362). Maciejewski et al. They tested chiral vanadyl salen complex anchored on activated carbon catalysts in the studied reaction (363). Fuels for this kind of power gen- eration. Zhou et al. have reported Pt-Bi based anode catalyst supported on activated carbon for glucose oxidation (361). Tapan et al. Lee et al. Fe-Cu-K/AC and Fe-Mo-Cu-K/AC catalysts for Fischer- Tropsch synthesis (350) and more recently Wang et al. Downloaded At: 18:30 25 January 2011 Electrochemical fuel cells convert the chemical energy of a fuel directly into electric power employing a catalytic process. Organosilicon compounds have attracted much interest from viewpoints of organic synthesis as well as new functional materials. have studied the effect of oxygen reduction on activated carbon electrodes loaded with manganese dioxide catalyst (356). have presented Pt-Cu/AC catalysts for the hydrosilylation of alkenes with poly(hydro. have studied the photochemical activity of Zn/AC catalysts by measuring the humic acid (HA) removal efficiency using UV/photocatalyst system (348). have tested activated carbon- based Ag-Cu electro-catalyst for anode electrode in direct ethanol fuel cells (358). have reported Pt-based anode catalyst supported on activated carbon for direct etha- nol fuel cells (357) and more recently.

sealant. 11) (365). and casting industries. and vanadium oxides sup- ported on activated carbon was carried out by Encarnação et al. Nagasaki et al. They are bicyclic isomers that undergo cationic polymerization by ring opening of their cyclobutane ring (Fig. Polymerization of α-pinene using cooper. Later Milewska et al. There is incentive to synthesize this molecule in a low-cost route for using it as a refrigerant and also because it useful a foam blowing agent and can be used to replace more environmentally damaging foam blowing agent previously employed in the production of polymeric foams (364). Pinene homopolymers belong to the family of terpenic resins that are low molecular weight valuable commercial products used by the adhesive. HC3 HC3 CH3 HC 3 + Limonene CH3 CH3 Tricyclene CH3 γ -Terpinene + H3C CH3 CH3 H3C H2C Camphene α -Pinene CH3 CH3 H2C CH3 H3C CH3 + H3C CH3 H3C CH3 H3C CH3 Terpinolene α -Terpinene Figure 11: Polymerization of α-pinene. wax coating. at lower carbon dioxide pressures. so that the reaction mixture in contact with the solid catalyst would either be biphasic (liquid þ gas) or a single supercritical phase. Calvino-Casilda et al. are completed faster than in supercritical conditions. have reported a novel catalytic reaction and its mechanism for CF3I synthesis using alkali metal salts supported on activated carbon. 352 V. Downloaded At: 18:30 25 January 2011 Experiments were performed at different carbon dioxide pressures. to obtain poly- mers of low molecular weigh. nickel. . carried out the hydro- genation of α-pinene in high-pressure carbon dioxide using Pt/C catalysts (366). The hydrogenations in biphasic conditions.

Aureus and for bacteria’s E.subtilis (379) and later Kennedy et al. have reported cerium. coli (381). Ni. have reported the glycerol dehydration to acrolein over activated carbon-supported silicotungstic acids (383). Zn. The catalyst increases the rate of a reaction and controls its selectivity. have generated hydrogen from alkaline NaBH4 solution via hydro- genolysis using Co/AC catalysts (377). have reported the antibacterial activity of Ag/AC catalysts against S. aureus and B. More recently. Rh. Pd. Moreno-Castilla group has prepared tungsten oxide catalysts supported on activated carbons for the isomerization of 1-butene (368. Faria et al. Hammad et al. preventing heart disease. have reported the antibacterial activity of Co. is being sold as a panacea that has the capability of reduce or even eliminate cancer. Nosheen et al. have prepared catalysts doping activated carbon with chromia gel for ozone decomposition and DEHP degradation (376). Mg and Ca/ AC catalysts against bacteria’s such as S. Co-Mo/AC and Ni-Mo/AC catalysts (371). Os and bimetallic Pt-Rh supported by activated carbon. have investigated the microwave assisted cracking of n- hexane over Pt/AC catalysts to produce lower hydrocarbons (C2 and C3) to efficiently activate automobile catalysts (373). Ucar et al. Xu et al.. Liu et al.369). Conjugated linoleic acid (CLA). have reported the catalytic ozonation of p-chlorobenzoic over Ni/AC catalysts (375). CONCLUSIONS AND FUTURE TRENDS Catalytic processes report more than 90% of the chemical manufacturing pro- cesses in use all over the world. Hutchings have carried out the ethyne hydrochlorination over Au/AC cata- lyst with the formation Markovnikov addition products (382). requiring . manganese and cobalt oxides as catalyst for the ozonation of selected organic compounds (aniline and sulfanilic acid) and azo dyes (374) and Li et al. Ru. Hisashi et al. Pt. have improved oil yield from coal extraction using Fe-Ni/ Downloaded At: 18:30 25 January 2011 AC. and altere the body composition in order to treat obesity or build lean body mass (370). have reported the upgrading scrap tire derived oils using Co-Ni/ AC. have reported the formation of oligomerization hydro- carbon products from an equimolar mixture of CF2Cl2 and H2 catalyzed by activated carbon-supported Pt-Cu catalysts (367). Last Decade of Research on Activated Carbons 353 Chakraborty et al. Ni-Mo/AC and sulphide catalysts Fe2S3/AC (372). have prepared cobalt(III)-salen complex supported on activated carbon as an efficient heterogeneous catalyst for synthesis of 2-arylbenzimidazole derivatives from phenylenediamines and aromatic aldehydes (378). reported the use of Cu/AC catalysts for the destruction of these pathogens in water (380). have reported the isomerization of polyunsaturated fatty acids such as linoleic acid to conjugated linoleic acid (CLA) over the following catalysts. Methakhup et al. Ning et al. Shargi et al. Ir. improve immune function. Ni. Bernas et al. Catalyst development is a complex process.

Catal. thus showing the remarkably wide range of potential applications. purity. 78: 1567. is catalysis on activated carbons. (1997) Europa Chemie. Fuel.M. M. extensive research to produce the high performance catalysts used today. ACKNOWLEDGMENTS V.-S. [5] Wu. cost efectiveness but also mechanical stability needs to be considered for the recyclability of the catalyst (green chemistry). surface functional groups (catalyst manufacturing). 354 V. 36: 159. J.M.C. J. the future growth of the use of the activated carbon in catalysis depends on the better understanding and subsequent control of the chemistry of activated carbon surface. T. (1998) VOC deep oxidation over Pt catalysts using hydrophobic supports.L. Calvino-Casilda et al. Carbon. Moser. Since in 1998 Rodríguez- Reinoso reviewed the properties of activated carbon as catalyst and catalyst support.-Y.C. Today. Fuel. (1999) Control of atmo- spheric emissions of volatile organic compounds using impregnated active car- bons. This review is dedicated to Prof... and Tonhaeuser. A. [4] Alvim Ferraz. de Dios López- González.C. Activated carbons have been used for some time in heterogeneous catalysis.. 79: 645. Specifically the role of the chemical nature of the activated carbon surface has become widely recognized during the last few years.. (1998) The role of carbon materials in heterogeneous cata- lysis. 24: 4. REFERENCES [1] Budzinski. (2000) Structure of impregnated active carbons produced with almond shells . acknowledges CSIC for the award of a JAE-Doctor contract. acting as direct catalysts and not long as catalyst support.C. porosity. [2] Rodríguez-Reinoso. The work has been supported by Spanish Ministry of Education and Science (project: CTM2007-60577/TECNO). this review gives an overview of current chemical processes catalyzed by activated carbon supported catalysts in the last decade. It is now recognized that activated carbon as a catalyst support offers unparallel flexibility in tailoring their physical (surface area and porosity) and chemical (surface functional groups) properties to specific needs.C. many advances has been got in this field especially on activated carbon Downloaded At: 18:30 25 January 2011 supported catalytsts. [3] Alvim Ferraz. M. In this way. who showed us how attractive. M. F. 44: 111.influence of impregnation methodol- ogy. and Cabral Monteiro. The properties and requeriments of activated carbon supports are closely related to the requirements of the catalyst. Therefore. The important parameters for activity and selectivity of a catalyst are not only surface area. physical and chemical surface properties of activated carbon have to be taken into account when designing a catalyst. S. inertness. J. . and Chang. However.

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