Article No : a18_321
Oxo Synthesis
HELMUT BAHRMANN, Celanese GmbH Ruhrchemie, Oberhausen, Federal Republic
of Germany
HANSWILHELM BACH, Celanese GmbH Ruhrchemie, Oberhausen, Federal Republic
of Germany
1. Introduction. . . . . . . . . . .....
2. Theory . . . . . . . . . . . . . . .....
3. Industrial Applications . .....
3.1. Rhodium Processes . . . . .....
1. Introduction
Olefins react with synthesis gas (carbon monox-
ide and hydrogen) in the presence of homoge-
neous catalysts to form aldehydes containing an
additional carbon atom. This hydroformylation
of olefins, known as oxo synthesis, was discov-
ered in 1938 by ROELEN of Ruhrchemie [1], [28,
10].
The most important oxo products are in the
range C3 C19 , [2], [8]; with a share of roughly
75 % butanal is by far the most significant. In
1997 the total worldwide oxo production capaci-
ty for aldehydes and alcohols was 6.5
106 t/a.
Table 1 gives an overview of the known facilities
and capacities.
Up until the mid-1970s only the cobalt-based
catalysts were important industrially. The situa-
tion changed in 1974 1975 when Union Car-
bide and Celanese, independently of one another,
introduced rhodium-based catalysts on an indus-
trial scale. Since then, cobalt catalysts for the
hydro formylation of propene have been replaced
in nearly all major plants by the more advanta-
geous rhodium catalysts despite the higher price
of the noble metal. This substitution was made
possible because the high price of rhodium was
offset by cheaper equipment, increased activity,
and a generally higher selectivity and efficiency.

2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
DOI: 10.1002/14356007.a18_321
.... ..... . 609 3.2. Cobalt Processes . . . . . . . . . . . . . . . . . . . . . 615
.... ..... . 609 References . . . . . . . . . . . . . . . . . . . . . . . . . . 615
.... ..... . 612
.... ..... . 612
Efficiency became extremely important follow-
ing the oil crisis in 1973, which shifted the the
cost structure in aldehyde production towards the
raw materials. For example, propene and synthe-
sis gas account for about 75 % of the product
value [9]. With the introduction of more expen-
sive rhodium catalysts, catalyst reprocessing,
which can be carried out batchwise or continu-
ously, became increasingly important [1222].
The catalyst lifetime can be severely diminished
by extrinsic poisons such as strong acids,
hydrogen cyanide, sulfur, hydrogen sulfide,
COS, oxygen, and dienes. The feedstocks must
therefore be very pure. Since 1978 [23] increased
attention has been paid to intrinsic deactiva-
tion (i.e., internal decomposition) of the rela-
tively expensive catalyst ligands [12] , [18], [24].
Next to the efficiency, activity, and selectivity of
the catalyst, the catalyst lifetime is the most
industrially important reaction parameter.
2. Theory
The mechanism developed by HECK and BRESLOW
[2527] for the reaction with cobalt catalysts
(see ! Organometallic Compounds) can be
largely applied to hydroformylation with rhodi-
um. However, the introduction of the triphenyl-
phosphine (PPh3) ligands in the catalyst system
brings about critical changes which already
affect the course of the reaction by formation of
various Rh complexes, which leads to new
effects that cannot be explained by the older
610 Oxo Synthesis Vol. 25

Table 1. Worldwide oxo capacities (1989)

Country Capacity, 103 t/a Products Process type *

Brazil 120 C4 1
Bulgaria 20 C4 5
China 300 C4 1, 5
Czech Republic 40 C4 5
Former Soviet Union 580 C4 5
France 355 C4, C8 C10, C13 1, 5
Germany 1695 C3 C13 15
India 40 C4, C8 C10 1, 4, 5
Italy 85 C12 C15 5
Japan 755 C4, C7 C15 1, 4, 5
Poland 150 C4 1
Romania 135 C4 5
Saudi Arabia 190 C4 1
South Korea 420 C4 1, 2
Spain 70 C4 1
Sweden 220 C4 1
The Netherlands 200 C8 C10 5
United Kingdom 150 C7 C15 4, 5
United States 2500 C3 C15 1, 4, 5
*
See Table 2.

cobalt model. For example, with the cobalt sys-
tem the fraction of unbranched aldehyde product
(or the n/i ratio) increases with increasing partial
pressure of carbon monoxide, while with rhodi-
um no effect or a lower n/i ratio is observed [1].
Fundamental mechanistic studies of the in-
dustrially important triphenylphosphine rhodium
catalyst system are based on the work of G.
WILKINSONs group and workers at Union Carbide
in the late 1960s [25], [28], [29].
Model studies with the hydride complex
[RhHCO(PPh3)3], the key compound in the hy-
droformylation reaction, were the first to provide
satisfactory explanations for the different reac-
tion behavior compared to cobalt catalysts.
For example, studies on the molecular mass
of this compound in various organic solvents
(e.g., benzene) indicated extensive dissociation
of this complex. This shows that an equilibrium
exists between the various substituted rhodium
complexes before the catalytic cycle occurs
[28]:
The predominant catalytic species is thus
determined by this equilibrium, which has
important consequences when the reaction is
carried out on an industrial scale.
According to R. L. PRUETT and J. A. SMITH,
under industrial reaction conditions (i.e., at high-
er temperatures and under CO/H2 pressure) the
above-mentioned equilibrium is also accompa-
nied by the competition of CO and PPh3 for free
coordination sites on the rhodium atom [29]:
Each catalytic species is assigned an individ-
ual reaction rate and a characteristic product
distribution. High phosphorus/rhodium ratios
and a lower partial pressure of carbon monoxide
favor the type 1 complex, which is assumed to
give a high n/i ratio as a result of steric effects,
since it is more highly substituted with phosphine
ligands.
Rhodium complexes with three phosphine
ligands were also postulated in 1981 by J. D.
UNRUH and O. R. HUGHES of Celanese as the basis
for a high n/i selectivity in the presence of
particular chelating ligands in combination with
certain monophosphine ligands [30]. In contrast,
the two basic dissociative and associative me-
chanisms, proposed by WILKINSON in 1968, are
Vol. 25
Figure 1. Dissociative mechanism after G. WILKINSON [7]
based on rhodium complexes with either one or
two phosphines [28]. Both mechanisms start with
the key complex 4 but differ as regards the
primary reaction step, i.e., coordination of the
olefin to the rhodium center.
In the dissociative mechanism dissociation of
a phosphine ligand from the bis(phosphine) com-
plex 4 is followed by addition of the olefin to the
coordinatively unsaturated square-planar com-
plex 6 (Fig. 1). There is very little steric hin-
drance because the complex only has a single
phosphine ligand. In contrast, in the associative
mechanism the olefin attaches directly to the bis
(phosphine) complex 4. The associative mech-
anism accounts for the fact that a higher selec-
tivity for the n-aldehyde is obtained in the
presence of excess phosphine. However, a high
n/i ratio can also be explained by the dissocia-
tive mechanism if the coordinatively unsaturat-
ed trans bis(phosphine) complex 2, [RhH(CO)
(PPh3)2] is assumed to be the active catalytic
species. WILKINSON [28] had already taken this
possibility into consideration, but rejected it
(Fig. 2).
As the olefin approaches the trans bis(phos-
phine) complex (Fig. 2 a) and forms an alkene
complex (Fig. 2 b) the substituents on the phos-
phine ligands impinge on the alkene due to
rotation about the Rh P bonds, whereby the
alkene groups are bent away from the direction of
Oxo Synthesis 611
approach. Additionally, the rotation and sweep-
ing of the phenyl groups of the PPh3 ligands in the
transfer step from the p complex (Fig. 2 b) may
favor formation of the n-alkyl complex (Fig. 2 c)
rather than the i-alkyl complex due to minimiza-
tion of steric hindrance, the i-alkyl complex
being more crowded than the n-alkyl complex.
Investigations by Exxon [31], [32], Johnson
Matthey [33], Montedison [24], [34], and J. M.
BROWN and A. G. KENT [35] clearly support the
dissociative mechanism. The active catalytic
species are probably unsaturated square-planar
rhodium complexes containing one or two coor-
dinated phosphine ligands (Fig. 3). These com-
plexes are in equilibrium with one another,
whereby complex 2 produces predominantly the
n-aldehyde and complex 6 the i-aldehyde.
Since 1990 an increasing number of investi-
gations [4649] have been performed on the
Figure 2. Control of the n/i ratio by a trans bis(phosphine)
rhodium complex [28]
612 Oxo Synthesis
Figure 3. Modified dissociative mechanism [32]
water-soluble tris(trisodium-3-sulfophenyl)
phosphine-modified [P(3-C6H4SO3Na)3] rhodi-
um hydroformylation catalyst system used in the
Ruhrchemie Rhone-Poulenc (RCH RP)
process (Fig. 4). A higher n/i ratio is obtained
in the RCH RP process than in the UCC pro-
cess, which uses triphenylphosphine as the
ligand. This can be explained by a relative shift
of the equilibrium between complexes 6 and 4
(see Fig. 1) toward complex 2 because of the
higher dissociation energy of the tris(trisodium-
3-sulfophenyl)phosphine ligand compared to the
triphenylphosphine ligand.
Figure 4. Structure of the water-soluble rhodium carbonyl
hydride complex
Vol. 25
3. Industrial Applications
The hydroformylation reaction is used on an
industrial scale to produce aldehydes and alco-
hols (! Alcohols, Aliphatic; ! Aldehydes,
Aliphatic; ! Butanals). These include bulk
products as well as high-value specialty
products.
The industrially important processes can be
divided into five main types. Table 2 gives an
overview of their catalyst systems, reaction con-
ditions, and expected products.
The cobalt catalysts are extensively described
in [13] , [8]. In the meantime their decline in
industrial importance has come to an end. Steady
improvements in the processing of branched
medium- to long-chain olefins (Table 2, Type 5
[5052]) and inner long-chain olefins (Table 2,
Type 4) have strengthened the position of these
older cobalt-based processes.
3.1. Rhodium Processes
As shown in Table 2, rhodium-based processes
can be classified into three types. The most
important of these on an industrial scale uses
the so-called phosphine-modified catalyst sys-
tem. The unmodified rhodium carbonyl complex
is used for the reaction of special olefins.
Vol. 25 Oxo Synthesis 613

Table 2. Comparison of the various oxo processes

Catalyst [RhH(CO)(PR3)3] [RhH(CO)4] [CoH(CO)3PR3] [CoH(CO)4]

R C6H5 R 3-C6H4SO3Na
Process type no. 1 2 3 4 5

Hydroformylation conditions
Pressure, bar 15 20 10 100 200 300 50 100 200 350
Temperature,  C 85 115 50 130 100 140 160 200 110 180
Results
Selectivity for aldehydes high high high low medium
n/i Ratio 92 : 8 95 : 5 50 : 50 88 : 12 80 : 20
Hydrogenation low low low high medium

Low-Pressure Oxo (LPO) Process.
Table 2, Type 1. In the mid-1970s Union Car-
bide and Celanese succeeded in using rhodium
triphenylphosphine catalysts for the hydrofor-
mylation of olefins on an industrial scale. Since
then some other companies have developed mod-
ifications of this process. The most important of
these, however, is the low-pressure oxo (LPO)
process jointly developed by Union Carbide,
Davy McKee, and Johnson Matthey. A detailed
description of this specific low-pressure route
follows with the conversion of propene to butyr-
aldehyde as an example.
Figure 5 shows a schematic of hydroformyla-
tion with the LPO gas-recycle process [8], [36].
The reaction takes place in a stirred-tank
reactor (a) made of stainless steel. The reactants
and supplementary catalyst to make up for cata-
lyst lost in production are fed in from below. Due
to the sensitivity of the rhodium catalyst system
toward catalyst poisons, the olefin and synthesis
gas or hydrogen used as makeup gas must first be
carefully purified (b). The reactor contains the
catalyst dissolved in high-boiling reaction by-
products. In order to maintain catalyst activity a
portion of the solution must be continuously
removed and reprocessed separately (c), and the
noble metal and the phosphine returned to the
process. From time to time, all of the catalyst
must be removed via line (d) and reprocessed
externally [12], [16]. The hydroformylation re-
action takes place at < 20 bar and 85 115  C.
The reactor jacket is cooled to remove the heat of
reaction. The reaction products and unreacted
gaseous reactants (conversion of about 30 % per
pass) are forced out of the reactor by the recycled

Figure 5. LPO process (schematic) a) Stirred-tank reactor; b) Reactant purification system; c) Reprocessing; d) To catalyst
reprocessing; e) Demister; f) Condenser; g) Separator; h) Compressor; i) Stripping column; j) Outlet
614 Oxo Synthesis
gas and pass through the demister (e) and the
condenser (f) into the separator (g).
Unreacted starting materials and part of the
propane formed as byproduct are recycled to the
reactor by means of the compressor (h). The level
of propane in the circulating gas is adjusted by
means of the outlet (j). The liquid reaction pro-
ducts are freed from residual olefin in a stripping
column (i), and are worked up by multistage
distillation. Residual olefin from the stripping
column is recycled. To limit the buildup of inerts
in the recycled gas stream and to reduce losses by
venting, other treatment steps may be applied.
These include extraction of propene with the
aldehyde products, stripping the olefin from the
aldehydes with synthesis gas and recycling both
to the reactor [55], and washing the off-gas with
stripped catalyst solution [56].
The LPO gas-recycle process has been partly
replaced by a liquid-recycle variant, in which the
catalyst solution and the aldehyde products leave
the reactor as a liquid. The catalyst solution is
separated from the aldehydes in several distilla-
tion steps and recycled. Combinations of gas and
liquid recycle have also been described and are
claimed to give increased propene conversion
[53], [54].
Ruhrchemie Rhone-Poulenc (RCH
RP) Process. Another industrial low-pressure
process for olefin hydroformylation (Table 2,
Figure 6. Schematic of the RCH RP process a) Stirred-tank reactor; b) Stripping column; c) Separator; d) Phase separator;
e) Heat exchanger; f) Water inlet; g) Off-gas outlet
Vol. 25
Type 2) is based on a water-soluble rhodium
catalyst (see Chap. 2) [3743]. As with the LPO
process, the RCH RP process has found its
greatest importance in the hydroformylation of
propene.
The use of a water-soluble catalyst system is
associated with substantial advantages for indus-
trial practice, because the catalyst can be consid-
ered to be heterogeneous. Since the catalyst is
insoluble in the organic phase formed, separation
of the aqueous catalyst phase and the butanal is
greatly simplified by phase separation, and losses
of the noble metal in the crude aldehyde stream
are negligible. High-boiling byproducts do not
dissolve in the aqueous catalyst phase, dispens-
ing with the need for continuous catalyst regen-
eration. In the LPO process, however, these
byproducts are retained in the catalyst phase and
lead to catalyst problems, unless the catalyst
system is continuously regenerated.
The process is explained by means of the
simplified flow sheet (Fig. 6). The reaction takes
place in a stirred-tank reactor (a), which contains
the catalyst solution; the reactants are introduced
from below. Before entering the reactor, the
synthesis gas is first passed through a stripping
column (b) in countercurrent to the crude alde-
hyde stream in order to recover the unreacted
propene. Furthermore, purification of the reac-
tants can be avoided by this procedure [42]. The
crude aldehyde product leaves the top of the
Vol. 25
reactor and passes through the trap (c) into the
phase separator (d) where it is separated from
the entrained catalyst solution. The catalyst so-
lution is returned to the reactor via the heat
exchanger (e).
Because of the higher temperature compared
to the LPO process (see Table 2), the heat of
reaction can be used for steam generation in the
heat exchanger (e). The crude aldehyde from the
phase separator (d) is distilled. Part of the water is
retained in the crude aldehyde in homogeneous
solution. This loss of water is compensated for
via inlet (f). Part of the off-gas which escapes via
the separator (c) can be recirculated; part must be
drawn off to maintain a constant propane level in
the gas. Depending on the purity of the olefin
used, the off-gas (g) may contain considerable
amounts of olefin. The RCH RP process may
then, for example, be combined with a cobalt
high-pressure process to convert the residual
olefin [44].
Rhodium High-Pressure Process. If un-
modified rhodium carbonyl hydride is used as
a hydroformylation catalyst, the reaction product
consists of roughly equal amounts of branched
and straight-chain aldehydes (see Table 2,
Type 3). For this reason this catalyst is only
applicable if the n/i ratio is not important (i.e.,
both aldehydes are valuable products) or if the
formation of a branched aldehyde is impossible
(e.g., in the hydroformylation of ethylene to give
propanal) [45]. Anhydrous propanal can be ob-
tained by this process.
3.2. Cobalt Processes
Modified Catalysts (Shell Process). If the
corresponding alcohol rather than the aldehyde is
the desired product, the Shell process can be
applied (Table 2, Type 4). A phosphine-modified
cobalt catalyst with a strong hydrogenation
activity is used and gives a favorable n/i ratio
(88 : 12) in the initially formed aldehyde product
mixture. The catalyst readily isomerizes feed
olefins and can therefore be used to hydroformy-
late inner olefins. For a detailed description of
this process see [2], [8].
Unmodified Catalysts. The first and, for a
long time, the most important, industrial oxo
Oxo Synthesis 615
process was based on an unmodified cobalt car-
bonyl hydride catalyst (Table 2, Type 5) which
required high pressures and temperatures. How-
ever, since the successful introduction of rhodi-
um catalysts its importance has declined but
since stabilized at a lower level.
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Further Reading
D. Astruc: Organometallic Chemistry and Catalysis,
Springer, Berlin 2007.
R. Ballini (ed.): Eco-friendly Synthesis of Fine Chemicals,
Royal Society of Chemistry, Cambridge, UK 2009.
M. Beller (ed.): Catalytic Carbonylation Reactions, Springer,
Berlin 2006.
E. Billig, D. R. Bryant: Oxo Process, Kirk Othmer Ency-
clopedia of Chemical Technology, John Wiley & Sons,
Hoboken, NJ, online DOI: 10.1002/0471238961.
15241502091212.a01.
A. Borner (ed.): Phosphorus Ligands in Asymmetric Cataly-
sis, Wiley-VCH, Weinheim 2008.
G. P. Chiusoli, P. M. Maitlis (eds.): Metal-Catalysis in
Industrial Organic Processes, Royal Society of Chemis-
try, Cambridge, UK 2006.
B. H. Davis, M. L. Occelli (eds.): Advances in Fischer-
Tropsch Synthesis, Catalysts, and Catalysis, CRC Press/
Taylor & Francis, Boca Raton, FL 2010.
P. A. Evans (ed.): Modern Rhodium-catalyzed Organic Re-
actions, Wiley-VCH, Weinheim 2005.
J. Hagen: Industrial Catalysis, 2nd ed., Wiley-VCH,
Weinheim 2006.
C. Higman, M. d. van Burgt: Gasification, 2nd ed., Elsevier,
Amsterdam 2008.
L. Koll
ar (ed.): Modern Carbonylation Methods, Wiley-
VCH, Weinheim 2008.