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C. R. Chimie 19 (2016) 314e319Contents lists avaiComptes Rendus Chimie
www.sciencedirect.comFull paper/MemoireSelective aqueous oxidation of alcohols catalyzed by copper
(II) phthalocyanine nanoparticles
Somayyeh Kheirjou a, Ramin Kheirjou b, Ali Hossein Rezayan c, **,
Mehdi Shakourian-Fard a, Mohammad Mahmoudi Hashemi a, *
a Department of Chemistry, Sharif University of Technology, Tehran, Iran
b School of Medicine, Tehran University of Medical Sciences, Tehran, Iran
c Department of Life Science Engineering, Faculty of New Sciences & Technologies, University of Tehran, P.O. Box 14395-1561, Tehran, Irana r t i c l e i n f o
Article history:
Received 2 May 2015
Accepted 24 November 2015
Available online 28 January 2016
Keywords:
Phthalocyanine nanoparticles
Oxidation
Alcohol
Oxon
Carbonyl* Corresponding author.
** Corresponding author.
E-mail addresses: ahrezayan@ut.ac.ir (A.H. Re
sharif.edu (M. Mahmoudi Hashemi).
http://dx.doi.org/10.1016/j.crci.2015.11.014
1631-0748/© 2015 Published by Elsevier Masson SAa b s t r a c t
A new catalyst based on metallophthalocyanine nanoparticles has been synthesized and
characterized by scanning electron microscopy (SEM). The aqueous oxidation of alcohols to
the corresponding carbonyl compounds (aldehydes and ketones) has been studied using
tetra-n-butyl-ammonium-peroxo-monosulfate (n-Bu4NHSO5) as an oxidant and a catalytic
system consisting of copper (II) phthalocyanine nanoparticles in water. The highly selective
oxidation gave excellent yields of related aldehydes or ketones without remarkable over-
oxidation of the carboxylic acids. Organic co-solvents, surfactants, and co-catalysts were
not used in this catalytic strategy. This strategy was green and time effective. The oxidant's
by-product (TBAHSO4) and catalyst can be efficiently recovered and reused several times
without any significant change of catalytic activity.
© 2015 Published by Elsevier Masson SAS on behalf of Academie des sciences.1. Introduction
Oxidation reactions are among the most important
transformations in synthetic chemistry and offer an
important methodology for the introduction and modifi-
cation of functional groups. Therefore, the oxidation of
alcohols by metal complexes to the corresponding
carbonyl compounds is a worthwhile goal [1,2]. Many
different oxidants were used for the oxidation of alcohols
such as pyridinium chlorochromate (PCC), pyridinium
dichromate (PDC), KMnO4, MnO2, CrO3, H2O2 and so on.
Most of these oxidizing reagents which can be used in a
research laboratory in stoichiometric amounts are
expensive or toxic [1,3]. Thus, offering innovative, “clean”zayan), mhashemi@
S on behalf of Academie demethods which use environmentally friendly oxidants
such as peroxides, molecular oxygen and tetra-n-butyl-
ammonium-peroxy-monosulfate and non-toxic solvents
in particular aqueous media could be a new challenge in
this regard. Moreover, it has been found that reactions in
water can facilitate access to different reactivity and
selectivity patterns compared with those observed in
common organic solvents due to its unique physical and
chemical properties. However, the manifestation of a new
catalytic oxidation system which is cost effective, non-
toxic and environmentally friendly is receiving a good
deal of attention.
Hydrogen peroxide oxidation is found to be less rela-
tively economical because of its cost and poor efficiency
[4,5]. Oxone (2KHSO5$KHSO4$K2SO4) has drawn a lot of
attention as amild and operative reagent for various organic
transformations in recent years [6e12]. However, oxone is
practically soluble in water. Then, perhaps the most signif-
icant drawback in the use of oxone is its application ins sciences.
Scheme 1. Oxidation of alcohols with n-Bu4NHSO5 catalyzed by copper (II)
phthalocyanine nanoparticles.
Fig. 1. SEM images of copper (II) phthalocyanine nanoparticles with average
diameters of 42 nm.
S. Kheirjou et al. / C. R. Chimie 19 (2016) 314e319 315aqueous or pH-controlled reactions [13]. Several salts
of oxone have been reported, such as tetra-n-butyl-
ammonium-peroxy-monosulfate (n-Bu4NHSO5, TBA-OX),
tetra-n-pentyl-ammonium-peroxy-monosulfate, tetra-n-he
xyl-ammonium-peroxy-monosulfate and benzyl-triphenyl-
phosphonium-peroxy-monosulfate. Recently, Lie et al. [14]
have demonstrated TBA-OX as an effective reagent for the
oxidation of alcohols in CH2Cl2 or H2O.
These tremendous advantages of TBA-OX have
encouraged us to choose it as an oxidant in our study.
There are several reagents available for the oxidation of
sulfides and alcohols, but most of them are not satisfac-
tory for medium to large scale synthesis due to the low
content of effective oxygen, formation of environmentally
unfavorably co-products, and high cost [15]. An aqueous
solution of TBA-OX is an excellent oxidant in terms of
being environmentally friendly, safe in storage and oper-
ation [14,15].
In this work, copper (II) phthalocyanine nanoparticles
were used as a catalytic system. Phthalocyanines (Pcs)
constitute a remarkably versatile and robust class of com-
pounds with diverse technological applications [16e18].
Phthalocyanine transition metal complexes are important
industrial pigments which have been considered as po-
tential oxidation catalysts due to their facile preparation on
a large scale, chemical and thermal stabilities. Metal-
lophthalocyanines have been used as efficient biomimetic
catalysts for the oxidation, reduction, and other reactions of
different organic compounds. However, the low solubility
of metallophthalocyanine catalysts is the most important
problem that is often encountered by the catalyst in
different reactions [8].
The extensive use of toxic and volatile organic solvents
in these oxidation systems has reduced considerably the
practical importance of biologically inspired oxidation
catalysis. The discarding of harmful organic solvents is a
problem in chemical industries which accounts for about
80% of their wastes [13]. Therefore, using non-toxic sol-
vents in aqueous media can play a significant role in these
reactions and a new challenge could be done to make such
a process in aqueous solutions or under solvent free con-
ditions [19e23].
Nanoinorganic materials are an interesting subject of
research because of their unique physical and chemical
properties [24]. Over hundred papers describing inorganic
nanoparticle reactions with different materials have
appeared in chemical literature studies in recent years.
Nanoparticles have recently emerged as efficient alterna-
tives for the immobilization of homogeneous catalysts.
Nevertheless, difficulties in recovering the nanoparticles
from the reaction mixture result from effective dispersion
in solution by forming stable suspensions, which limit their
wide applications [25,26].
In continuation of our interest in exploring the oxida-
tion of organic compounds [27e30], this study aims to
report a mild and effective heterogeneous strategy for the
aqueous oxidation of alcohols by n-Bu4NHSO5 and copper
(II) phthalocyanine as catalysts (Scheme 1). However, to the
best of our knowledge, the use of copper (II) phthalocya-
nine nanoparticle catalysts for the oxidation of alcohols has
not been previously reported.2. Experimental
1H and 13C spectra were determined on a Varian Mer-
cury 300 MHz or a Bruker AM-400. Gas chromatographic
analyses were performed on a Hewlett Packard 6890 in-
strument equipped with a FID detector and an HP-1 (either
a 10 m  0.2 mm i.d. or a 25 m  0.2 mm i.d.) capillary
column.2.1. Preparation of the nano-CuPc
Copper (II) phthalocyanine was synthesized according
to literature procedures [27e30]. Then, copper phthalocy-
anine nanoparticles up to 42 nmwere prepared pursuant to
the following procedures. Briefly, 0.15 g CuPc was first
dissolved in 5 ml 98% concentrated sulfuric acid, and then
the solution was added drop-by-drop into a 300 ml
aqueous solution containing 0.45 g hexadecyltrimethyl
ammonium-bromide in an ultrasonic ice-water bath.
Isolation of phthalocyanine nanoparticles from a solution
phase was done by using a simple centrifuge.
The obtained nanoparticles were washed immediately
with hydrochloric acid twice, to remove bromide and then
washed with deionized water three times. The final prod-
uct was dried at 40 C under vacuum.
Characterization of copper (II) phthalocyanine nano-
particles was performed with a SEM as shown in Fig. 1
[31,32]:
Confirmation of the catalyst structure was done by
elucidating UV (Fig. 2). Fig. 2 shows the absorption spec-
trum of CuPc and its related nanoparticles. Other metal
phthalocyanines have very similar absorption spectra in
the visible spectral region; these bands were assigned to
p/p transitions of the macrocyclic p-system [33].
Fig. 2. Absorption spectra of CuPc (black) and its related nanosized particles (red) in the ultra-violet and visible (UVeVis) wavelength ranges.
Fig. 3. The effect of temperature on the aqueous oxidation of cyclohexanol
using tetra-n-butyl-ammonium-peroxo-monosulfate catalyzed by nano-
CuPc.
Fig. 4. The reaction profile for aqueous oxidation of cyclohexa
S. Kheirjou et al. / C. R. Chimie 19 (2016) 314e319316The oxidant (TBA-OX) was prepared from commercially
available oxone and n-Bu4NHSO4 by a procedure described
in the literature [34].3. Results and discussion
Copper (II) phthalocyanine nanoparticles have provided
a valuable tool for the synthesis of both aliphatic and aro-
matic carbonyl compounds. In a typical reaction, n-
Bu4NHSO5 as an oxidant (two equivalents) was added to
the magnetically stirred aqueous solution of a mixture of
alcohol (1 mmol) and copper (II) phthalocyanine. The
oxidation of cyclohexanol with TBA-OX as an oxidant in
aqueous media did not proceed in the absence of catalyst.
Introductory catalytic experiments were addressed to thenol using n-Bu4NHSO5 catalyzed by nano-CuPc at 85 C.
Fig. 5. Recycling of the catalytic system for the oxidation of cyclohexanol.
Table 1
The oxidation of various alcohols.
Entry Alcohol Product Yield% M.P./B.P. of
product (C)
1 64 56
2 95 153
3 89 161
4 87 113e115
5 86 205e208
6 90 49
7 94 115
8 92 202
Table 1 (continued )
Entry Alcohol Product Yield% M.P./B.P. of
product (C)
9 79 179
10 85 249
11 83 204
12 88 48
13 92 105
S. Kheirjou et al. / C. R. Chimie 19 (2016) 314e319 317oxidation of cyclohexanol (1 mmol) with n-Bu4NHSO5
(0.7 g) in the presence of desired copper (II) phthalocyanine
nanoparticles (0.5 mol%) in aqueous solution at 25 C under
air which led to the formation of cyclohexanone in 55%
yield after 8 h according to GC analysis. Then, the temper-
ature effect on the aqueous oxidation of cyclohexanol using
n-Bu4NHSO5 catalyzed by nano-CuPc was examined. It can
be concluded from Fig. 3 that an increase in the tempera-
ture remarkably increased the effectiveness of the catalytic
system. The full conversion of cyclohexanol was achieved at
85 C within 72 min (Fig. 3).
Under these conditions, the oxidation reaction pro-
ceeded smoothly and cyclohexanone was secured in 95%
yield after a simple extraction from the aqueous phase. It is
worth mentioning that blank experiments for the oxidation
of cyclohexanol using TBA-OX as an oxidant at 70 C gave
just 10% of cyclohexanone after 1 h. The conversion of
cyclohexanol as a function of temperature is shown in Fig. 3.
The yield of oxidation of cyclohexanol to the cyclohex-
anone as a function of time is indicated in Fig. 4.
It is important to note that using organic co-solvents
such as dichloromethane and n-hexane mitigated the re-
action yields; 55, 47 and 6% yields have been obtained for
water, dichloromethane/water and n-hexane/water,
respectively.
The effect of increasing the amount of catalyst from 0.1
to 1 mol% on cyclohexanol oxidation and product selec-
tivity was examined. When the catalyst amount was
S. Kheirjou et al. / C. R. Chimie 19 (2016) 314e319318increased, the reaction yield also increased. For instance,
34, 71, 100 and 100 have been obtained for the 0.1, 0.2, 0.5
and 1 mol% of catalyst, respectively. It is worth mentioning
that the increasing mol percent of catalyst up to 5 does not
have any seminal effect on the reaction yields. However, the
full conversion of cyclohexanol was achieved with a low
catalyst loading of 0.5 mol %.
Recycling of the catalyst has also been studied. The
catalyst was separated from the product by simple
extraction with ether. n-Bu4NHSO4 can be recycled by
removing the aqueous phase. Tetrabutylammonium
hydrogen sulfate (TBAHS) is a phase transfer catalyst and
can be reused in the preparation of TBA-OX. The proce-
dure was repeated 4 times in the oxidation of cyclo-
hexanol (Fig. 5) [35].
In order to exploit the general applicability of the present
catalytic system, several primary and secondary aliphatic
and aromatic alcohols were selected for oxidation under
optimized conditions in the aqueous solution. Secondary
alcohols gave good yields and these are generally excellent
substrates for this oxidation system (Table 1, entries1e8).
Oxidation of primary alcohols such as benzylic and aliphatic
occurredwith a slow reaction rate and gave low tomoderate
yields of the related carbonyl compounds (entries 9e13).Scheme 2. Proposed mechanismTotal aromatic alcohols gave better yields than aliphatic al-
cohols in the oxidation reaction by this catalyst.
Based on literature studies [36e38], the proposed
mechanism for this catalytic oxidation reaction is depicted
in Scheme 2. In the first step, copper phthalocyanine (CuPc)
reversibly combines with TBA-OX. Apparently, due to the
less steric hindrance around the terminal oxygen atom of
the peroxo residue (HOeOSO3), the attachment of this
species to the metal centre through the terminal peroxo
oxygen atom is more facile relative to the other oxygen
atoms of TBA-OX [39]. Cu(III)eOO species induces
hydrogen abstraction from the studied alcohols resulting in
the formation of an alcoholic radical. In a rebound process
and subsequent cleavage, the corresponding carbonyl
compound is produced [40,41].
Table 2 shows a comparison between the catalytic effi-
ciency of CuPc nanoparticles and other catalysts found in
the literature. As seen in Table 2, the reaction did not pro-
ceed without any catalyst at room temperature. The use of
12-tungstocobaltate (II), NaCl, and TEMPO-IL/[bmim][PF6]
as catalysts at room temperature gave 85, 65, and 90%
yields at different times. Our catalyst was more effective in
terms of yield and reaction time compared to the other
reported catalysts.for the oxidation reaction.
Table 2
A comparison between the catalytic efficiency of CuPc nanoparticles and other catalysts found in the literature for the oxidation of alcohol.
Entry Oxidant catalyst Tempreture Time/min Yield/% [Ref]
1 TBOX e 60 180 10<
2 TBOX 12-tungstocobaltate (II) 50 180 85 [42]
3 TBOX NaCl 25 300 65 [43]
4 TBOX TEMPO-IL/[bmim][PF6] 60 30 90 [35]
5 TBOX CuPC nanoparticles 85 70 95
S. Kheirjou et al. / C. R. Chimie 19 (2016) 314e319 3194. Conclusion
In conclusion, the catalytic performance of nanocopper
(II) Phthalocyanine in the oxidation of alcohols using water
as a solvent and n-Bu4NHSO5 as an oxidant was studied.
The excellent yieldwas achieved for oxidation of alcohols at
85 C with the absence of surfactants and nitrogenous
bases. The employment of neat water as a ‘green’ solvent in
this oxidation method gave high yield products as well as
easy and safe work-up which are strong points of this novel
methodology making it more attractive for practical goals.
Organic co-solvents, surfactants, and co-catalysts were not
used in this catalytic strategy. This system was green and
time effective.Acknowledgement
We gratefully acknowledge the financial support from
the Research Council of Sharif University of Technology. We
also thank Vivekanand V. Gobre at Fritz Haber institute der
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Selective aqueous oxidation of alcohols catalyzed by copper (II) phthalocyanine nanoparticles

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lable at ScienceDirectContents lists avaiComptes Rendus Chimie
www.sciencedirect.comForeword/Avant-propos
Workshop on alternative solvents for extraction, purification
and formulation (WAS2014)Workshop international sur les solvants alternatifs pour l'extraction,
la purification et la formulation (WAS2014)Foreword
Nowadays, solvents are widely used in manufacturing
processes such as perfume, cosmetics, pharmaceutical,
food ingredient, nutraceutical, biofuel or fine chemical in-
dustries, where they are used for extraction, purification,
formulation or synthesis processes. Recent trends in natu-
ral product chemistry have largely focused on finding so-
lutions that minimize the use of solvents or alternatives to
petroleum solvents. This must be achieved while also
enabling process intensification and a cost-effective pro-
duction of high-quality extracts.
The objective of this workshop was to provide a com-
plete picture of the current knowledge on alternative and
green solvents used at laboratory and industrial scales for
extraction, purification, formulation, and synthesis of nat-
ural products in terms of innovation, original methods and
procedures, and safety of the products. The workshop was
aimed at professionals from industry, academic researchers
and lecturers engaged in natural product chemistry, and
graduate-level students. The scientific program consisted
of 13 conferences with highly recognized experts and 34
posters by young researchers and PhD students.
More than 180 scientists and experts from industry
(50%) and academia (50%) from 15 countries have partici-
pated in this workshop held in Avignon, France, a venue
that created an environment for information exchange,
generation of new ideas, and acceleration of applications
that benefit science and society. WAS2014 had served as a
catalyst for the advancement of research in the field of
‘‘alternative solvents’’ by connecting scientists and experts
within and across disciplines (extraction, synthesis,
formulation, and purification) from around theworld in the
vibrant City of the Popes, Avignon, France.
Avant-propos
Aujourd'hui, tout procede d'extraction, de synthese, de
purification ou de formulation de principes actifs danshttp://dx.doi.org/10.1016/j.crci.2016.04.008
1631-0748/© 2016 Academie des sciences. Published by Elsevier Masson SAS.
creativecommons.org/licenses/by-nc-nd/4.0/).l'industrie cosmetique, la parfumerie, l'agroalimentaire, la
pharmacie ou la valorisation de la biomasse met en œuvre,
directement ou indirectement, des solvants issus de
ressources fossiles, devenus incontournables dans ces
differents secteurs d'applications. L'utilisation de ces sol-
vants petroliers est de plus en plus souvent montree du
doigt pour leur participation a la pollution environ-
nementale et a l'effet de serre. Par ailleurs, l’epuisement
progressif des ressources petrolieres et le durcissement de
la reglementation incitent les industriels, mais aussi les
chercheurs academiques, a s'orienter vers la recherche et
l'utilisation de solvants alternatifs plus respectueux de
l'environnement.
Cette journee thematique sur les solvants alternatifs
pour l'extraction, la purification, la synthese et la formu-
lation a permis aux domaines utilisant des solvants d'entrer
dans leur revolution « verte », en operant une mutation
vers des solvants alternatifs issus de la biomasse. Plus de
150 chercheurs et experts, representant plus de 55 pays,
venant du milieu industriel (50 %), mais aussi academique
(50 %), ont participe a cette premiere rencontre sur les
solvants alternatifs (WAS2014), qui s'est tenue a Avignon
(France), la Cite des papes.
Farid Chemat
Avignon University, France
Anne-Sylvie Fabiano Tixier*
Avignon University, France
Antoine Bily
Naturex, France
Natacha Rombaut
ORTESA LabCom, NaturexeAvignon University, France
 Corresponding author.
E-mail address: anne-sylvie.fabiano@univ-avignon.frThis is an open access article under the CC BY-NC-ND license (http://


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Charles Frédéric Kuhlmann: A key figure in the golden age period of chemical industry in northern France

Workshop on alternative solvents for extraction, purification and formulation (WAS2014)

CV3 - Editorial Board - English

Structural, physicochemical and in vitro pharmacological properties of the stimulant drug 8-chlorotheophylline complexed with Cr(III), Mn(II), Co(II), and Ni(II) metal ions: Potent metallodrug complexes as antimicrobial agents

Fe<sub>3</sub>O<sub>4</sub>@SiO<sub>2</sub>/collagen: An efficient magnetic nanocatalyst for the synthesis of benzimidazole and benzothiazole derivatives

2,199

3,559