Nano-pistachio hull-O xTiCl4?x: synthesis, characterization and application as an effective and novel nanocatalyst for one-pot synthesis of dihydropyrano[3,2-b]chromenedione derivatives

Article abstract of DOI:10.1007/s13738-020-02096-6

According to the Food and Agriculture Organization (FAO), Iran is the largest pistachio (Pistacia vera) producer in the world. Nevertheless, pistachio by-products (PBs) contain a high level of phenolic and cellulose compounds, it can be used as a substrat

Full text of DOI:10.1007/s13738-020-02096-6

Journal of the Iranian Chemical Society
https://doi.org/10.1007/s13738-020-02096-6
ORIGINAL PAPER
Nano‑pistachio hull‑OxTiCl4 − x: synthesis, characterization
and application as an efective and novel nanocatalyst for one‑pot
synthesis of dihydropyrano[3,2‑b]chromenedione derivatives
Sayed Rasul Shafe‑Mehrabadi1 · Bahareh Sadeghi1 · Mohammad Hossein Mosslemin1 · Saeedeh Hashemian1
Received: 6 March 2020 / Accepted: 12 October 2020
© Iranian Chemical Society 2020
Abstract
According to the Food and Agriculture Organization (FAO), Iran is the largest pistachio (Pistacia vera) producer in the
world. Nevertheless, pistachio by-products (PBs) contain a high level of phenolic and cellulose compounds, it can be used
as a substrate for the preparation of solid acid catalysts. In this work, the novel pistachio hull-OxTiCl4 − x catalyst was syn-
thesized via preparing pistachio hull, product of Kerman, as a support followed by treatment with titanium tetrachloride
(TiCl4) and identifed by Fourier transform infrared spectroscopy, feld emission scanning electron microscopy (FE-SEM),
X-ray difraction spectroscopy (EDX), thermogravimetric analysis (TG), Brunauer–Emmett–Teller (BET) and X-ray powder
difraction (XRD). The size of the nano-pistachio hull-OxTiCl4 − x nanocatalyst was shown by a scanning electron microscope
below 100 nm. The catalytic activity of the solid acid catalyst has been successfully examined in a one-pot, three-component
condensation reaction of aromatic aldehydes, dimedone and kojic acid in refuxing ethanol to furnish dihydropyrano[3,2-b]
chromendione derivatives. Consequently, pyran annulated heterocycles were obtained. The proposed approach has some
advantages as excellent yields, mild reaction conditions, short reaction times, use of agricultural waste and eco-friendly.
Keywords Kojic acid · Nanocatalyst · Pistachio hull · Green biosynthesis · Solid acid
Introduction
because of its high adsorption ability, low cost, and easy sus-
tainability [7]. Much like other agricultural lignocellulosic
biomass, such as coconut shell [8], sawdust [9], and peanut
shell [10], pistachio hull is composed mainly of lignin, cellu-
lose and hemicelluloses. Consequently, the main active sites
of pistachio hull are a wide variety of hydroxyl groups that
can be used for the preparation of solid acid catalysts [7].
The multi-component (three reactant or more) reactions
(MCRs) have been developed in organic chemistry and mod-
ern drug discovery owing to the generation of biologically
active products [11].
Nanoscience and nanotechnology have considerable ecologi-
cal interest as a very infuential and efcient strategy in the
feld of medicinal organic, and combinatorial chemistry. Due
to the unique dimensions and size, physical properties, easy
recyclability, large specifc surface area of nanostructures
[1], there is widely current attention in nanoparticle appli-
cation as catalysts, biomedical use, energy storage, enzyme
encapsulation, photonics, and drug delivery [2–5]. During
the past years, the use of recyclable heterogeneous catalyst
(a solid catalyst that is dispersed on a supporting material
to increase surface area and provide stability) has received
signifcant importance in organic chemistry [6].
In addition, high atom economy, cost-efectively, energy
saving, lower reaction time and raw materials, structural
complexity and environmentally benign synthesis of chemi-
cally and biologically important organic frameworks are the
most advantageous features encountered in MCRs [12–14].
Dihydropyrano[3,2-b]chromendione derivatives are some
examples of multi-component synthesis that three starting
materials react in a single fask [15–20].
The pistachio hull is an agricultural by-product and
would be an excellent bio-resource for preparing solid acids
* Bahareh Sadeghi
sadeghi@iauyazd.ac.ir
Pyrans and its derivatives are an important category of
oxygen-containing heterocycles which is present in a num-
ber of important pharmaceuticals and natural products such
1
Department of Chemistry, Yazd Branch, Islamic Azad
University, P.O. Box 89195-155, Yazd, Iran
Vol.:(0123456789)
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Journal of the Iranian Chemical Society
as alkaloids, carbohydrates, polyether antibiotics, iridoids
and pheromones. Polyfunctionalized pyrans have attracted
considerable attention because of their broad spectrum of
signifcant biological and pharmaceutical properties such as
antimicrobial, antifungal, anticancer, antioxidant, anti-tumor
and anti-HIV [21–25].
and, after 60 min, the ashy powder was separated and washed
with chloroform (15 mL) and n-hexane (15 mL), respectively.
Subsequently, for obtaining a fne and homogenized pistachio
hull-OxTiCl4 − x powder, the obtained solid was dried in an
oven at 70 °C for 4 h and then pulverized at the mortar.
Considering the importance of biologically active
pyran templates, an efficient and environmentally
benign approach was developed for the synthesis of
dihydropyrano[3,2-b]chromendiones via one-pot three-
component condensation of aromatic aldehydes, 5-hydroxy-
2-hydroxymethyl-4H-pyran-4-one (kojic acid) and 5,5-dime-
thyl-1,3-cyclohexanedione(dimedone) in the presence of
nano-pistachio hull-OxTiCl4 − x as a readily available, highly
efcient, recyclable and novel catalyst in EtOH as an inex-
pensive and non-toxic medium.
General procedure for preparation of compounds
4a–m
Nano-pistachio hull-OxTiCl4−x(7.0 mg) were added to a stirred
mixture of kojic acid 1 (1.0 mmol), dimedone 2 (1.0 mmol)
and aromatic aldehyde 3 (1.0 mmol). The materials were
mixed and heated under refux in EtOH (5 mL) for the appro-
priate time as mentioned in Table 4. The progress of the reac-
tion was followed by TLC (n-hexane/ethyl acetate 3:1). After
completion of the reaction, the reaction mixture was fltered to
remove the catalyst and then the crude product was recrystal-
lized from hot ethanol to obtain the pure compound by evapo-
ration of the solvent.
Experimental
General
Results and discussion
The chemicals used in this work were purchased from
Fluka (Buchs, Switzerland) and were used without further
purifcation. Melting points were determined with an Elec-
trothermal 9100 apparatus. IR spectra were recorded on a
In association with our recent achievement in the design of
innovative recyclable heterogeneous nanocatalysts to the pro-
duction of heterocycles [8–10], herein we studied synthesis of
nano-pistachio hull-OxTiCl4−x as highly efcient novel hetero-
geneous nanocatalyst for the preparation of dihydropyrano[3,2-
b]chromendiones. The novel pistachio hull-OxTiCl4−x catalyst
was simply prepared as given in Scheme 1 and its characteris-
tics instrumentally were evaluated.
1
Shimadzu IR-470 spectrometer. H and 13C NMR spectra
were recorded on Bruker DRX-400 Avance spectrometer
at solution in CDCL3 using TMS as internal standard. The
morphologies of the nanoparticles were observed using
FESEM of a MIRA3 TESCAN microscope with an accel-
erating voltage of 15 kV. The IR spectra of the catalyst were
recorded using a model Bruker Tensor 27 Fourier transform
infrared spectroscopy (FT-IR). The EDX analysis was done
using a SAMx-analyzer. Thermogravimetric analysis was
performed by using a TGA 209 F3Tarsus. X-ray difraction
(XRD) pattern was obtained in the 2θ range from 10 to 80
by a Philips Xpert MPD difractometer equipped with a Cu
Kα anode (k=1.54 A°). Surface areas and pore size of nano-
pistachio hull-OxTiCl4 − x were undertaken using BELSORP-
miniII from N2 adsorption at relative pressure P/P0 =0.99 in
the Brunauer–Emmet–Teller (BET) model.
As shown in Fig. 1, the average particle size of pistachio
hull-OxTiCl4−x and its distribution were analyzed by FESEM.
As shown in FESEM, the size of pistachio hull-OxTiCl4 − x is
below 100 nm, and on the other hand, the spots on the pis-
tachio shell surface can be attributed to titanium tetrachlo-
ride groups (Fig. 1c). The spot EDX results indicate these
observations.
As shown in Fig. 2, elemental composition of the pistachio
hull and nano-pistachio hull-OxTiCl4 − x was investigated by
EDX analysis which is shown in Table 1. Pistachio hull is
composed of C, O, K and Cl (Fig. 2a), while pistachio hull-
OxTiCl4 − x (Fig. 2b) is composed of C, O, K, Cl and Ti. The
presence of Ti and increase in the percentage of Cl in the EDX
indicate that the chemical interaction of titanium tetrachloride
with the surface of pistachio hull.
Preparation of nano‑pistachio hull‑OxTiCl4 − x
At frst, the pistachio hull was collected from Kerman city of
Iran and washed several times with deionized water to remove
adhering impurities and then dried at 60 °C for 24 h. The dried
pistachio hull was pulverized at the mortar and sieved using a
20-mesh sieve and labeled as pistachio hull. To prepare nano-
pistachio hull-OxTiCl4−x, TiCl4 (0.7 mL) was added dropwise
over 10 min via a syringe to pistachio hull powder (1.0 g) in
5 mL of chloroform at 0 °. The reaction mixture was stirred
Thermogravimetric analysis (TGA) and derivative ther-
mogravimetric analysis (DTG) were performed to assess
the thermal stability of nano-pistachio hull-OxTiCl4 − x
Pistachio hull-OH + TiCl → Pistachio hull-O TiCl + HCl
4 x 4-x
Scheme 1 Preparation of nano-pistachio hull-OxTiCl4 − x
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Journal of the Iranian Chemical Society
Fig. 1 a, b SEM micrograph
of pistachio hull (c, d) SEM
micrograph of nano-pistachio
hull-OxTiCl4 − x
Fig. 2 a EDX of pistachio hull and b EDX of nano-pistachio hull-OxTiCl4 − x
(Fig. 3). Three thermal decomposition mass loss steps are
observed for the pistachio hull-OxTiCl4-x: (a) There was a
35.73% weight loss from 25 to 190 °C for sample assigned to
desorption of H2O/Cox molecules from the surface of nano-
pistachio hull-OxTiCl4 − x and the further dehydration of pis-
tachio (190 °C); (b) 23.18% weight loss at 200–290 °C is due
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Journal of the Iranian Chemical Society
The absorption bands at nearly 1649 cm−1 indicate the C=C
bond in phenyl rings of lignin unit. The C–O band was
observed at 1152 cm−1, and the Ti–O stretching vibrations
observed at 673 cm−1. The FT-IR data and the presence of
these elements in the EDX vividly approved the actual event
of chemical interaction of titanium tetrachloride with the
surface area of pistachio hull.
Table 1 Chemical analysis of pistachio shell and nano-pistachio hull-
OxTiCl4 − x
Element
Pistachio shell (W%)
Nano-pistachio
hull-OxTiCl4 − x
(W%)
C
50.26
43.81
0.41
5.52
–
30.73
30.16
13.92
2.41
O
Cl
K
Ti
The XRD patterns can be used to describe the crystal-
linity of nano-pistachio hull-OxTiCl4 − x catalyst. The X-ray
difraction pattern for the nano-pistachio hull-OxTiCl4 − x
catalyst is shown in Fig. 5. The XRD pattern for the nano-
pistachio hull-OxTiCl4 − x catalyst displayed distinct peaks
at 2θ = 28.6°, 40.7°, 50.4° and 66.6°, respectively. As can
be seen, peaks indicate the presence of crystalline nano-
pistachio hull structure and prove the bonding of Ti to the
cellulose backbone. The XRD analysis of the prepared sam-
ple of TiO2 nanoparticles was done using a Bruker make
difractometer, Cu-Kα X-rays of wavelength (λ)=1.5406 Å,
and data were taken for the 2θ range of 10° to 70° with a step
of 0.1972° [27]. The results confrmed the nano-pistachio
hull-OxTiCl4 − x catalyst and are not TiO2.
22.77
to the decomposition of cellulose; and (c) 18.80% weight
loss in the range of 300–1000 °C is due to the decomposi-
tion of lignin units. (The frst decomposition shoulder peak
at about 300 °C is attributed to thermal depolymerization of
hemicelluloses or pectin. The major second decomposition
peak at about 390–400 °C is attributed to cellulose decom-
position, and the small peak at 420 °C may be attributed to
oxidative degradation of the charred residue. Lignin as a
component of the fbers was degraded at a higher tempera-
ture. The structure of lignin is a highly aromatic polymer.
Possibly, it was removed by benzene in larger amount than
the other solvents). Based on nano-pistachio hull-OxTiCl4 − x
TG-DTG diagram, the substance is stable up to 144.5 °C;
hence, the catalyst can be used at temperatures below 150 °C
for promotion of organic synthesis. In the case of initial
TiO2-NPs, there was no further mass loss up to 900 °C [26].
In FT-IR spectrum of nano-pistachio hull-OxTiCl4 − x
exhibited a broad peak for the hydroxyl bands of cellulose
units at 3446 cm−1 (Fig. 4). The C–H stretching vibrations
of the aliphatic systems for cellulose observed at 2937 cm−1.
Brunauer–Emmett–Teller (BET) theory aims to explain
the physical adsorption of gas molecules on a solid surface
and serves as the basis for an important analysis technique
for the measurement of the specifc surface area of materials.
In order to further understand the nature and geometry of the
pores formed, BET adsorption–desorption isotherms were
studied and analyzed for the as-synthesized nano-pistachio
hull-OxTiCl4 − x catalyst. The adsorption–desorption curves
show a pores following H2 hysteresis of the IUPAC classi-
fcation. The adsorption isotherm increases gradually until
a relative P/Po of 0.6 followed by a change in slope at the
Fig. 3 TGA/DTG curves of
nano-pistachio hull-OxTiCl4 − x
samples
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Journal of the Iranian Chemical Society
Fig. 4 FT-IR spectrum of
nano-pistachio hull-OxTiCl4 − x
catalyst
Fig. 5 X-ray difraction pattern of nano-pistachio hull-OxTiCl4 − x catalyst
curve beyond 0.6 which is attributable to the condensation
taking place at the neck and the interconnected inner-bottled
structure. However, the desorption curves show pores fol-
lowing H4 hysteresis of the IUPAC classifcation (Table 2,
Fig. 6).
Table 2 BET results of nano-pistachio hull-OxTiCl4 − x catalyst
Sample weight (g)
0.0109
77
88
14.481
1.1368
313.99
Adsorption temperature (k)
Saturated vapor pressure (KPa)
Average pore diameter (nm)
After synthesis and characterization of the nano-pistachio
hull-OxTiCl4 − x as a novel, stable and eco-friendly nano-
catalyst, we investigated the performance of nano-pistachio
hull-OxTiCl4 − x in the synthesis of dihydropyrano[3,2-b]
chromenediones. First, a test model reaction was done with
1.0 mmol benzaldehyde, 1.0 mmol kojic acid and 1.0 mmol
dimedone in the existence of various amounts of nano-pis-
tachio hull-OxTiCl4 − x using diferent solvents. The results
Total pore volume (cm3 g−1
)
AS, BET (m2 g−1
)
of these experiments are given in Table 3. In the absence
of nano-pistachio hull-OxTiCl4 − x, no desired product was
formed (Table 3, entry 1). The favorable result was found
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Journal of the Iranian Chemical Society
Fig. 6 BET adsorption–desorption isotherm and pore size desorption curve
with 7.0 mg nano-pistachio hull-OxTiCl4 − x in refuxing
ethanol (Table 3, entry 2). A remarkable advantage of this
technique is that the catalyst can be recovered at the end of
the reaction and can be used several times without losing its
aldehydes under the optimized condition for the synthe-
sis of dihydropyrano[3,2-b] chromenedione derivatives
(Scheme 2). Results are given in Table 4 indicating that dif-
ferent aromatic aldehydes substituted with either electron-
donating or electron-withdrawing groups could react with
kojic acid and dimedone smoothly and give products in
excellent yield.
activity. To regenerate the nano-pistachio hull-OxTiCl4 − x
,
after completion of the reaction, the mixture was fltered
and recrystallized from hot ethanol; catalyst was separated
and washed with ethanol and then dried to obtain the solid
remainder. This procedure repeated for two cycles and the
yield of product 4a did not change signifcantly (Table 3,
entries 9, 10).
A detailed reaction mechanism for the synthesis of
dihydropyrano[3,2-b]chromenediones(4) using nano-pista-
chio hull-OxTiCl4 − x, which act as a solid acid catalysis in
all steps is outlined in Scheme 3 [30, 31]. Initially, nano-pis-
tachio hull-OxTiCl4 − x activates the dimedone and aldehyde
to form the olefn (5). The Michael addition of kojic acid
After optimizing tests, we conducted reaction of
kojic acid and dimedone with a variety of substituted
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Journal of the Iranian Chemical Society
Table 3 Optimization of the reaction conditions for synthesis of 4a
Entry
Catalyst (mg)
Solvent
Time (min)
Yielda (%)
1
2
3
4
5
6
7
8
9
Nano-pistachio hull-OxTiCl4 − x(0.0)
Nano-pistachio hull-OxTiCl4 − x(7.0)
Nano-pistachio hull-OxTiCl4 − x(7.0)
Nano-pistachio hull-OxTiCl4 − x(7.0)
Nano-pistachio hull-OxTiCl4 − x(7.0)
Nano-pistachio hull-OxTiCl4 − x(3.0)
Nano-pistachio hull-OxTiCl4 − x(5.0)
Nano-pistachio hull-OxTiCl4 − x(9.0)
Nano-pistachio hull-OxTiCl4 − x(7.0) 2nd run
Nano-pistachio hull-OxTiCl4 − x(7.0) 3rd run
EtOH
EtOH
n-Hexane
H2O
CH3CN
EtOH
EtOH
EtOH
EtOH
EtOH
120
20
20
20
20
20
20
20
20
20
0
95
Trace
90
45
67
79
95
92
89
10
Reaction condition: benzaldehyde (1.0 mmol), kojic acid (1.0 mmol) and dimedone (1.0 mmol) under refux in various solvents
aIsolated yields
Scheme 2 Synthesis of dihydropyrano[2,3-b] chromenedione derivatives in the presence of nano-pistachio hull-OxTiCl4 − x as a catalyst
(3) with olefn (5) in the presence of nano-pistachio hull-
OxTiCl4 − x fnally gives intermediate (7), which then makes
the inner molecular ring (8) to be formed after dehydration
in the existence of catalyst to produce the corresponding
product (4).
Conclusions
To conclude, we have introduced a well-organized, eco-
friendly, and simple procedure for the efcient synthesis of
dihydropyrano[3,2-b]chromenedione derivatives in high-
to-excellent yields via a one-pot three-component reac-
tion by using nano-pistachio hull-OxTiCl4 − x as a mild,
efective, non-toxic and inexpensive solid acid catalyst in
ethanol without the addition of organic co-solvent. The
promising points for the presented methodology are envi-
ronmental acceptability, economic viability, easy work-up,
short reaction time, high atom economy and fnally com-
pliance with the green chemistry protocols. Meanwhile,
solid-phase acidic catalyst could be reused for a number
of times without appreciable loss of activity. Moreover,
our work is expected to show interesting pharmacology
activities and may act as potential drug candidates, since
To show the merit of the present work in comparison
with the reported results in the literature, we compared the
results of nano-pistachio hull-OxTiCl4 − x as catalyst with
Alum [28], InCl3 [29], CeCl3·7H2O [32], Bi(OTf)3 [33],
FeCl3·SiO2 [34] and nano-Bi2O3-ZnO [35] in the synthe-
sis of dihydropyrano[3,2-b]chromenediones. As shown in
Table 5, entry 1, this new catalytic system compared to pre-
vious similar works has a number of advantages such as
shorter reaction time, higher yields, lower reaction tempera-
ture, use of agricultural waste and most importantly, avoid-
ance of hazardous or toxic catalysts and organic solvents. In
all these cases, our work has introduced green and more eco-
nomically cost-efective relative to previous similar works.
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Journal of the Iranian Chemical Society
Table 4 Synthesis of
Entry
Ar
Product
Time (min)
Yielda
M.P.(ºC) [Ref.]
dihydropyrano[3,2-b]
chromenedione derivatives
1
2
3
4
5
6
7
8
C6H5
4-Cl-C6H4
3-Cl-C6H4
2-Cl-C6H4
4a
4b
4c
4d
4e
4f
20
20
20
20
18
15
15
20
25
25
30
30
30
95
92
91
93
92
96
95
90
86
89
87
87
88
185–186 [28]
204–206 [28]
196–197 [29]
215–217 [28]
160–162 [28]
212–213 [28]
230–232 [28]
164–166 [28]
197–199 [29]
216–218 [28]
173–175 [28]
176–178 [28]
190–192 [28]
4-F-C6H4
3-NO2-C6H4
4-NO2-C6H4
2,4-Cl2-C6H3
2,4,6-(Me)3-C6H2
4-Me-C6H4
3,4,5-(MeO)3-C6H2
4-MeO-C6H4
2,5-(MeO)2-C6H3
4g
4h
4i
9
10
11
12
13
4j
4k
4l
4m
Reaction condition: aldehyde (1.0 mmol), kojic acid (1.0 mmol), dimedone (1.0 mmol) and nano-pistachio
hull-OxTiCl4 − x (7.0 mg) in ethanol (5 mL) under refux condition
aIsolated yields
Scheme 3 Suggested mechanism for the synthesis of dihydropyrano[2,3-b] chromenediones in the presence of nano-pistachio hull-OxTiCl4 − x as
a catalyst
Table 5 Comparison of the
Entry
1
Catalyst (amount)
Temp. (ºC)/solvent
Time (min)
15–30
Yield (%)
86–96
Ref.
catalytic performance of nano-
pistachio hull-OxTiCl4 − x with
other catalysts to the production
of dihydropyrano[3,2-b]
Nano-pistachio hull-
OxTiCl4 − x (7.0 mg)
Alum (0.1 mmol)
Refux/EtOH
This work
2
3
4
5
6
7
100/–
120/–
110/–
120/–
100/–
100/–
40–70
80–95
30–60
20–45
40–80
60–120
85–95
85–95
86–96
85–95
84–96
75–84
[28]
[29]
[32]
[33]
[34]
[35]
chromenedione derivatives
InCl3 (10 mol%)
CeCl3·7H2O (0.05 mmol)
Bi(OTf)3 (0.05 mmol)
FeCl3·SiO2 (0.05 mmol)
Nano-Bi2O3-ZnO (0.03 g)
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Journal of the Iranian Chemical Society
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