Magnetically recoverable lanthanum hydroxide as an efficient catalyst for Aerobic Oxidative Conversions of primary alcohols to the nitriles

Article abstract of DOI:10.1002/aoc.4253

Herein we report a novel magnetically recoverable lanthanum hydroxide nanoparticles for oxidative synthesis of nitriles directly from corresponding alcohols with ammonia as nitrogen source. The procedure for the preparation and characterization of La(OH)₃/Fe₃O₄ magnetic nanoparticles were investigated and the scope and generality of the method was explored for a series of structurally diverse primary alcohols with electron-donating and electron-withdrawing groups. The best result was observed when 5?mol% of La with respect to the benzyl alcohol was used at reflux condition under O₂ atmosphere. The La(OH)₃/Fe₃O₄ magnetic nanoparticles could be easily isolated from the reaction mixture with an external magnet and reused at least 5 times without significant loss in activity.

Full text of DOI:10.1002/aoc.4253

Received: 31 August 2017
DOI: 10.1002/aoc.4253
Revised: 17 November 2017
Accepted: 20 November 2017
F U L L P A P E R
Magnetically recoverable lanthanum hydroxide as an
efficient catalyst for Aerobic Oxidative Conversions of
primary alcohols to the nitriles
Fariborz Ziaee | Mostafa Gholizadeh
| Seyed Mohammad Seyedi
Department of Chemistry, Faculty of
Herein we report a novel magnetically recoverable lanthanum hydroxide nano-
particles for oxidative synthesis of nitriles directly from corresponding alcohols
with ammonia as nitrogen source. The procedure for the preparation and char-
acterization of La(OH)3/Fe3O4 magnetic nanoparticles were investigated and
the scope and generality of the method was explored for a series of structurally
diverse primary alcohols with electron‐donating and electron‐withdrawing
groups. The best result was observed when 5 mol% of La with respect to the
benzyl alcohol was used at reflux condition under O2 atmosphere. The
La(OH)3/Fe3O4 magnetic nanoparticles could be easily isolated from the reac-
tion mixture with an external magnet and reused at least 5 times without signif-
icant loss in activity.
Science, Ferdowsi University of Mashhad,
Mashhad 91775‐1436, I.R., Iran
Correspondence
Seyed Mohammad Seyedi, Department of
Chemistry, Faculty of Science, Ferdowsi
University of Mashhad, Mashhad 91775‐
1436, I.R. Iran.
Email: smseyedi@um.ac.ir
Funding information
Research Council of Ferdowsi University
of Mashhad, Grant/Award Number:
3/41313
KEYWORDS
direct oxidative nitrile synthesis, Lanthanum hydroxide, magnetic catalyst, primary alcohols
1 | INTRODUCTION
low yields and difficulty of product purification, which
are in contradiction with the green chemistry standpoint.
Nitriles are an important molecular scaffold for the
synthesis of various organic moieties like esters, acids,
amines, amides, and ketones which are important
synthetic precursors of natural products,[1] pharmaceuti-
cals,[2] agricultural chemicals and dyes.[3] Historically,
the Sandmeyer reaction,[4] Rosenmund–von Braun
reaction,[5] and gas‐phase oxidation were used for the
laboratorial and industrial synthesis of aryl nitriles,
respectively. The nucleophilic substitution of alkyl halides
with toxic inorganic cyanide salts in stoichiometric
amount were also reported for the synthesis of alkyl
nitriles. For the synthesis of unsaturated nitriles,
aldehydes and cyano alkylphosphates were reacted via
Therefore, the development of new synthetic pathways
under mild conditions for the synthesis of nitriles is of
significant interest.
In the last years, new procedures using different
catalysts and compounds have been reported. Transition
metal‐catalyzed dehydration of aryl oximes or amides is
one of these green approaches for the synthesis of
nitriles.[9] Also, different studies have been reported for
oxidative dehydrogenation of benzyl alcohols,[10]
azides[11] and methyl arenes.[12] The oxidative synthesis
of nitriles directly from alcohols or aldehydes with ammo-
nia as a nitrogen source instead of inorganic cyanides was
investigated as an eco‐friendly and green method using
inexpensive and available substrates and nitrogen source
with only water as byproduct which lead to the high atom
efficiency. Also, a few approaches have been reported for
the synthesis of nitriles directly from alcohols which in
the most of them the stoichiometric amount of oxidants
Wittig reaction.[6]
A less toxic cyanation reagent
(K3[Fe(CN)6]),[7] and non‐metallic cyanation sources[8]
have been reported previously. These methods tradition-
ally suffered from the use of toxic reagents, production
of large amounts of organic waste and inorganic salts,
Appl Organometal Chem. 2018;e4253.
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https://doi.org/10.1002/aoc.4253

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ZIAEE ET AL.
and reagents were needed.[13,14] In this regard, different
reagents such as I2, I2/DIH, I2/TBHP, NiSO4/K2S2O8/
NaOH, MnO2/MgSO4, and (Bu4N)2S2O8/Cu‐(HCO2)2/
Ni(HCO2)2/KOH were reported.[10] Abundance of
inexpensive molecular O2 has made it an excellent
oxidant with benign byproducts (usually only H2O).
Tao,[15] Huang,[16] Muldoon,[17] and Stahl[18] reports
showed that Cu/TEMPO (TEMPO=2, 2, 6, 6‐
tetramethylpiperidine‐ N‐oxyl) system efficiently cata-
lyzes the aerobic oxidative transformation of alcohols
or aldehydes to the corresponding nitriles in aqueous
ammonia as nitrogen source under mild reaction condi-
tions. The formation of nitriles from aldehydes has been
promoted with Ag nanoparticles and K4Fe(CN)6.[19]
Also, O‐(4‐CF3‐benzoyl)‐hydroxylamine as organic acid
catalyst was reported for this transformation.[20] These
methods offer great improvements but purification and
separation problem of these systems still needs to be
improved. Recently, the Mizuno group reported that
heterogeneous Ru(OH)x/Al2O3 system acts as an effi-
cient catalyst for aerobic oxidative transformation of
alcohols into nitriles by using ammonia in THF.[21]
Ishida group subsequently disclosed a method using
MnO2 under pressured oxygen and NH3 gas.[22] These
efficient systems suffer from high reaction temperature
which needs to an autoclave in many cases. The metal
hydroxides have both Lewis acid and Brønsted base
properties. This acidic and basic properties derive from
the same metal and the most of organic transformations
likely be promoted by the ‘concerted activation’ of the
Lewis acid and Brønsted base sites.[23–25] Based on liter-
atures, the nitrile hydration with monomeric CoIII–OH
complexes occurs via coordination of nitriles to the CoIII
Lewis acid centers and intramolecular nucleophilic
attack of the hydroxide species as Brønsted base on
the proximal activated nitrile carbon.[26] Synthesis of
nitriles from alcohols with ammonia and O2 are likely
promoted by the concerted activation of the Lewis acid
and Brønsted base sites in three steps: 1) the sequential
oxidation reactions of the alcohol,[27] 2) Dehydrative
condensation of the formed aldehyde with ammonia,
and 3) Oxidation of imine.[28] Nevertheless, the intricacy
of catalysts recovery and workup procedures are the
major drawback of these catalytic reactions. Recently,
we have developed efficient magnetic heterogeneous cat-
alyst for organic functional group transformation.[29]
Investigation of the supported magnetic nanoparticles
with easy separation ability from the reaction mixture
has become an important choice. Their insolubility and
magnetic nature make it possible to realize various reac-
tions and reduce the capital and operational costs.[30]
In this project we design a novel magnetically recov-
erable lanthanum hydroxide nanoparticles for oxidative
synthesis of nitriles directly from corresponding alcohols
and ammonia as nitrogen source. To the best of our
knowledge, employing Fe3O4/La(OH)3MNPs as
a
catalyst in aerobic oxidative synthesis of nitriles has
not been disclosed. This method is a highly desirable
method due to the easy separation and recovery of
catalyst, mild reaction conditions, and high yields of
products.
FIGURE 1 TEM images of (a) Fe3O4 MNPs, (b) La(OH)3/Fe3O4,
(c) SEM image of La(OH)3/Fe3O4, (d) EDS analyzes of La(OH)3/
Fe3O4

ZIAEE ET AL.
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at 80 °C in oven. The products were isolated by a silica gel
column chromatography and final nitriles were
confirmed by Mass spectra, 1H and 13C NMR spectra
(see supporting information).
2 | EXPERIMENTAL
2.1 | Synthesis of Fe3O4 magnetic
nanoparticles
Fe3O4 Magnetic nanoparticles were prepared via a previ-
ously reported hydrothermal method.[31] FeCl3.6H2O
(0.8 g), sodium acetate (2 g,) and (0.75 g) trisodium citrate
were dissolved in ethylene glycol (35 ml) under vigorous
stirring for 30 min. The resulting solution was transferred
into a Teflon‐lined stainless‐steel autoclave with 50 ml of
capacity and heated to 200 °C for 16 h. The obtained black
Fe3O4 MNPs were collected with a magnet and washed
several times with water and ethanol and dried at 80 °C.
3 | RESULTS AND DISCUSSION
For morphology study of La(OH)3/Fe3O4 TEM and SEM
analyzes were used. As shown in Figure 1a the Fe3O4
nanoparticles are in spherical shape with average diame-
ters of about 20 nm. TEM image of La(OH)3/Fe3O4 are
almost rod shaped lanthanum hydroxides which attached
with spherical magnetic nanoparticles with average
diameters of about 50 nm (Figure 1b). Figure 1c show
the SEM image of La(OH)3/Fe3O4 nanocatalyst with an
aggregated spherical morphology, probably due to the
magnetic nature of catalyst. The content of La in the sam-
ple was 21.55% based on inductively coupled plasma/opti-
cal electron microscopy (ICP‐OES). The EDS result
(Figure 1d) showed that the elemental composition of
the nanocatalyst are Fe, O, and La which agrees well with
the XRD analysis (Figure 2).
As shown in Figure 2, XRD analysis was used for the
crystalline structure study of Fe3O4 and La(OH)3/Fe3O4.
Six diffraction peaks at 2θ = 30.31, 35.64, 43.31, 53.86,
57.24, 62.83 attributed to the spherical phase planes of
the Fe3O4 crystal [34] according to the JCPDS card no.
19‐0629 (Figure 2a). As shown in Figure 2b, the character-
istic peaks of Fe3O4 becomes weak in La(OH)3/Fe3O4 due
to the heavy atom effect of La. Also, new peaks indexed
according to the JCPDS card No. 36‐1481 were appeared
which attributed to the hexagonal La(OH)3 crystalline
structure.[32]
2.2 | Synthesis of La(OH)3/Fe3O4 magnetic
nanoparticles
The La(OH)3/Fe3O4 MNPs were synthesized by a facile
sol–gel method. Typically, 0.15 g Fe3O4 was added to the
three‐neck round bottom flask followed by addition of
35 ml ethanol/water solution (1:1) containing 0.5 g
LaCl3.7H2O. The mixture was sonicated for 30 min, and
then 15 ml 0.5 M ethanol solution of NaOH was added
and stirred for 30 min. The reaction was maintained at
80 °C for 12 h. The black precipitate was collected by an
external magnet and then dried at 80 °C for 6 h.
2.3 | Direct oxidative synthesis of nitriles
from primary alcohols
1 mmol of primary alcohol, 5 mol% of La(OH)3/Fe3O4,
2 ml of 1,4‐Dioxane, and NH3 (equiv. NH3/alcohol= 2.2)
were refluxed under O2 balloon. The reaction process
was monitored by thin layer chromatography (TLC). After
the completion of the reaction, the catalyst was separated
by an external magnet, washed with ethanol, aqueous
solution of NaOH and water. The catalyst was then dried
The magnetic nature of La(OH)3/Fe3O4 was shown in
Figure 3. The La(OH)3/Fe3O4 exhibit a ferromagnetic
behavior at the room temperature. The magnetic satura-
tion value (Ms) of the La(OH)3/Fe3O4 is 62 emu/g. These
FIGURE 2 XRD patterns of (a) Fe3O4
and (b) La(OH)3/Fe3O4

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ZIAEE ET AL.
FIGURE 3 Magnetization hysteresis
loops of La(OH)3/Fe3O4nanocatalyst
results demonstrate that the La(OH)3/Fe3O4 particles
possess magnetic properties.
the catalyst amount was studied in the model reaction.
The best result was observed when 5 mol% of La with
respect to the benzyl alcohol was used at reflux condition
(Table 1, entries 1‐3). Dimethyl sulfoxide (DMSO), 1,4‐
Dioxane, and toluene were examined as reaction solvents
which shows a good performance and final benzonitrile
was produced in 70, 75, and 75 % of yields, respectively
(Table 1, entries 2, 4, and 5). In case of toluene the
The catalytic activity of prepared La(OH)3/Fe3O4 eval-
uated in aerobic oxidative conversion of benzyl alcohol to
benzonitrile as a model reaction in ammonia as a nitrogen
source under an oxygen balloon. For investigation of reac-
tion condition different parameters were studied after
1.5 h of beginning of the model reaction (Table 1). At first,
TABLE 1 Optimization of reaction conditionsa
Entry
Cat. (mol %)
Solvent
T (°C)
1a:NH3 (equiv.)
Yield 1b (%)
1
La(OH)3/Fe3O4 (10)
DMSO
reflux
1:1
71
2
La(OH)3/Fe3O4 (5)
La(OH)3/Fe3O4 (2)
La(OH)3/Fe3O4 (2)
La(OH)3/Fe3O4 (2)
La(OH)3/Fe3O4 (2)
La(OH)3/Fe3O4 (2)
La(OH)3/Fe3O4 (2)
La(OH)3/Fe3O4 (2)
La(OH)3/Fe3O4 (2)
La(OH)3/Fe3O4 (2)
La(OH)3/Fe3O4 (2)
La(OH)3/Fe3O4 (2)
La(OH)3/Fe3O4 (2)
Fe3O4
DMSO
reflux
reflux
reflux
reflux
reflux
reflux
reflux
80
1:1
70
20
75
75
10
8
3
DMSO
1:1
4
1,4‐Dioxane
Toluene
1:1
5
1:1
6
EtOH
1:1
7
MeOH
1:1
8
H2O
1:1
10
65
30
̶
9
1,4‐Dioxane
1,4‐Dioxane
1,4‐Dioxane
1,4‐Dioxane
1,4‐Dioxane
1,4‐Dioxane
1,4‐Dioxane
1,4‐Dioxane
1,4‐Dioxane
1:1
10
11
12
13
14
15c
16c
17
50
1:1
rt.
1:1
reflux
reflux
reflux
reflux
reflux
reflux
1:1.2
1:1.7
1:2.2
1:2.2
1:2.2
1:2.2
77
79
87
̶
LaCl3
̶
̶
̶
aReaction condition: 1a (1 mmol), catalyst (La: 5 mol% with respect to 1a), NH3 (2.2 mmol), and solvent (2.0 mL) under an O2 balloon at reflux for 1.5 h. [b]
isolated yield. [c] 0.15 mg of catalyst.

ZIAEE ET AL.
5 of 8
TABLE 2 Scope of the La(OH)3/Fe3O4 catalyzed direct conversion of benzyl alcohols to nitrilesa
Entry
Substrate
Time (h)
Product
Yield (%)
1
2
95
2
3
4
2
94
93
90
2
2.5
5
6
7
2.5
1.5
2
91
96
94
8
9
2.5
2
95
90
10
11
3
2
88
93
12
13
3
3
89
91
14
15
24
24
̶
̶
0
0
aReaction conditions: benzyl alcohol (1 mmol), aqueous NH3 (2.2 equiv.), La(OH)3/Fe3O4 (5 mol%), 1.4‐Dioxane (2 ml) under O2 balloon at reflux.
reaction proceed in extended time, probably due to the
low solubility of ammonia in toluene. Also, ethanol,
methanol and water were examined as protic solvents
but very low yield of benzonitrile was observed which
can be attributed to strong coordination ability of protic
solvents to the lanthanum active sites of catalyst
(Table 1, entries 6‐8). Based on these results 1,4‐Dioxane
was selected as a reaction solvent. As the reaction temper-
ature decrease from 80 °C to room temperature the prod-
uct yield was dropped (entries 9‐11). Also, when

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ZIAEE ET AL.
equivalent of ammonia was increased the higher yield of
benzonitrile was achieved in shorter time (entries 12‐14).
Results revealed that in the absence of any catalyst the
reaction does not proceed. The same results were
achieved when Fe3O4 and LaCl3 was used as reaction
catalyst (Table 1, entries 15‐17).
The above results showed the high efficiency of
La(OH)3/Fe3O4/NH3/O2 system in the conversion of
benzyl alcohols to aryl nitriles. Based on the optimized
conditions, the scope and generality of the process was
explored for a series of structurally diverse primary
alcohols as summarized in Table 2. Benzyl alcohols with
electron‐donating and electron‐withdrawing groups
could convert into the corresponding substituted
benzonitriles with excellent yields (90–96%, Table 2,
entries 1‐8). The position of substituents on benzyl alco-
hol did not much affect the reaction. The reaction con-
versions of multi substituted benzyl alcohols (Table 2,
entries 9‐11) and hetero‐aromatic alcohols (Table 2,
entries 12 and 13) were also good. However, aliphatic
primary alcohols could not be converted to the desired
products in this catalytic system (Table 2, entries 14
and 15).
The heterogeneity of the catalyst was also studied.
The transformation of benzyl alcohol to benzonitrile
was proceed under the optimized reaction condition
and after 1 h the La(OH)3/Fe3O4 was removed from
the reaction mixture by an external magnet. After
removal of the catalyst the filtrate was analyzed with
ICP‐OES analysis that no lanthanum was detected. This
study revealed that no lanthanum species was leached
into the reaction solution and showed the heterogeneity
of the catalyst.[33]
FIGURE 4 (a) Recycling test for La(OH)3/Fe3O4 catalyzed
oxidative synthesis of benzonitrile, (b) TEM image of recycled
catalyst
Recovery and reusability of La(OH)3/Fe3O4 was stud-
ied in the model reaction. After completion of the reaction
La(OH)3/Fe3O4 was separated from the reaction mixture
by an external magnet, washed with ethanol, aqueous solu-
tion of NaOH, and water and then dried at 80 °C for 2 h.
The catalyst was used at least in 5 successful runs without
significant decrease in activity (Figure 4a). Reaction condi-
tions: benzyl alcohol (1 mmol), aqueous NH3 (2.2 equiv.),
La(OH)3/Fe3O4 (5 mol%), 1.4‐Dioxane (2 mL) under O2
balloon at reflux. Based on ICP‐OES results the La content
of La(OH)3/Fe3O4 after 5 recycles was 19.47% which shows
about 2% of La leaching after 5 recycle. For the morphology
study of recycled catalyst TEM image of La(OH)3/Fe3O4
after 5 recycle was taken which in comparison with TEM
of catalyst before any catalytic use (Figure 1b) no morphol-
ogy changes were found. Based on this observation we can
conclude that the morphology of catalyst remains
unchanged after 5 recycle (Figure 4b). The yield dropping
of oxidation product after 5 recycle can be attributed to
the leaching of La moieties.
SCHEME 1 A possible mechanism of La(OH)3/Fe3O4 catalyzed
synthesis of nitriles from alcohols

ZIAEE ET AL.
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4 | CONCLUSION
A novel magnetically recoverable lanthanum hydroxide
nanoparticles were synthesized for the oxidative synthesis
of nitriles directly from corresponding alcohols with
ammonia as nitrogen source. The scope and generality
of the process was explored for a series of structurally
diverse primary alcohols with electron‐donating and elec-
tron‐withdrawing groups with 5 mol% of La with respect
to the benzyl alcohol at reflux condition under O2. This
catalyst can be easily separated and recovered with an
external magnet from the reaction mixture for further
use which act as an efficient heterogeneous catalyst for
the aerobic oxidative synthesis of nitriles directly from
alcohols without producing the over‐oxidation products‐
benzoic acids. This catalyst provides a green method for
nitrile synthesis, which avoids the use of the conventional
inorganic cyanides. Also, the catalyst was recovered and
reused at least for 5 successful runs without significant
decrease in catalytic activity.
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[18] J. Kim, S. S. Stahl, ACS Catal. 2013, 3, 1652.
The authors gratefully acknowledged for partially finan-
cial support of this study (Grant No: 3/41313) by Research
Council of Ferdowsi University of Mashhad.
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ORCID
[22] a) T. Ishida, H. Watanabe, T. Takei, A. Hamasaki, M.
Mostafa Gholizadeh http://orcid.org/0000-0002-9947-2248
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Seyed Mohammad Seyedi
http://orcid.org/0000-0001-
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SUPPORTING INFORMATION
Additional Supporting Information may be found online
in the supporting information tab for this article.
[29] F. Ziaee, M. Gholizadeh, S. M. Seyedi, Appl. Organomet. Chem.
2017. https://doi.org/10.1002/aoc.3925
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How to cite this article: Ziaee F, Gholizadeh M,
Seyedi SM. Magnetically recoverable lanthanum
hydroxide as an efficient catalyst for Aerobic
Oxidative Conversions of primary alcohols to the
nitriles. Appl Organometal Chem. 2018;e4253.
https://doi.org/10.1002/aoc.4253
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