Nicotine-derived ammonium salts as highly efficient catalysts for chemical fixation of carbon dioxide into cyclic carbonates under solvent-free conditions

Article abstract of DOI:10.1039/c5ra08488a

A series of easily prepared nicotine-derived ammonium salts were applied for the first time as recyclable and efficient catalysts for the coupling of carbon dioxide and epoxides to form cyclic carbonates at low pressure without using additional organic so

Full text of DOI:10.1039/c5ra08488a

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ARTICLE
Nicotine-derived ammonium salts as highly efficient
catalysts for chemical fixation of carbon dioxide into
cyclic carbonates under solvent-free conditions
Cite this: DOI: 10.1039/x0xx00000x
Abdol R. Hajipour a,b* , Yasaman Heidari a and Gholamreza Kozehgary c
Received 00th January 2012,
Accepted 00th January 2012
A series of easily prepared nicotineꢀderived ammonium salts were applied for the first time
as recyclable and efficient catalysts for the coupling of carbon dioxide and epoxides to form
cyclic carbonates at low pressure without using additional organic solvents and coꢀcatalysts.
Remarkably, excellent yields and selectivity were achieved when 1ꢀBenzylꢀ1ꢀmethylꢀ2ꢀ
pyridinꢀ3ꢀylꢀpyrrolidinium bromide [MBNT]Br was used as the catalyst. Furthermore, the
catalyst can be easily recovered and reused without a significant loss of activity. The
influences of the catalyst structure and various reaction parameters on the catalytic activity
were also investigated in detail.
DOI: 10.1039/x0xx00000x
www.rsc.org/
importantly, Suzuki et al.26 reported the solubility of nicotine in
carbon dioxide and also the presence of the tertiary nitrogen in
Introduction
Carbon dioxide is an attractive C1 feedstock gas in organic
synthesis as it is extremely practical, inexpensive, abundant,
nonꢀtoxic, and nonꢀflammable. As petroleum treasuries are
exhausted, the development of efficient catalytic systems for
CO2 fixation is consequently a significant and challenging
theme.1ꢀ3 In this regard, the synthesis of cyclic carbonates from
epoxides and CO2 has attracted widespread attention owing to
the 100% atom efficiency of the reaction and the wide range of
applications of cyclic carbonates such as polar aprotic solvents
in organic and polymeric synthesis, electrolyte components for
lithium batteries and intermediates in the syntheses of
pharmaceuticals.4ꢀ6
the cation has the potential to react with CO2 to form the
carbamate species, assumed to be an activated form of CO2.27
Indeed, the ammonium salt [MBNT]Br displayed high catalytic
activity for conversion of CO2 and epoxide to cyclic carbonate
and respectable yield together with excellent selectivity
obtained without utilization any organic solvents or additives.
In the past decades, a wide variety of homogeneous and
heterogeneous catalysts have been developed for this reaction,
such as alkali metal salts,7,8 metal oxides,9 Csꢀloaded zeolite
and alumina,10 transition metal salen complexes,11 zeolite,12
quaternary ammonium and phosphonium salts,13ꢀ18 and various
ionic liquids (ILs).19ꢀ23 However, most of these catalysts suffer
one or more of the following drawbacks: low catalyst activity,
the need of higher CO2 pressure and/ or longer reaction time,
the presence of expensive transition metal additives, and water
or air sensitivity. Hence, the design of easily prepared, metalꢀ
free catalysts with enhanced catalytic activity for the
conversion of CO2 to cyclic carbonate still remains a challenge.
In this study, a series of ammonium salts derived from nicotine
(scheme 1) are considered for the first time as catalysts towards
the cycloaddition reaction of carbon dioxide with epoxide.
These salts have advantages such as the facile preparation of
various structures24,25 from nicotine and benzyl or alkyl halides,
gratifyingly thermal behaviour, air/water stability. More
Scheme 1. Nicotine and ammonium salts based on nicotine
used in this study
Results and Discussion
At the initial study, a series of ammonium salts based on
nicotine have been applied to catalyse the cycloaddition
reaction of styrene oxide (SO) and CO2. The results are
summarized in Table 1. It can be seen that nicotine which
contains basic active sites afforded styrene carbonate (SC) in
40% yield (Table 1, entry 1), while after the quaternization,
monobenzylnicotinum salts showed higher catalytic activities (
table 1, entries 2, 3), indicating that without any anions the
presence of only nicotine could not afford highly active centers
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for this reaction. Hence, the effects of halogen anions such as
Clꢀ and Brꢀ on the catalytic activity were examined, and it was
found that [MBNT]Br showed much higher activity than
[MBNT]Cl (entry 3 vs 2) probably being ascribed to the
nucleophilicity and leaving ability of the anion in the
corresponding ammonium salt.28ꢀ30
To obtain more information for the effects of tertiary amine
group in the cation part on the reaction, dibenzylnicotinum
bromide [DBNT]Br which has no basic active sites was
investigated. [DBNT]Br was found to be inactive probably due
to loss of basic active sites and consequently loss of its CO2
activation effect27 (Table 1, entries 4). This result indicated that
the effect of tertiary amine group was a significant factor in
promoting the reaction. Therefore, [MBNT]Br was selected as
the benchmark structure for further studies on the reaction
parameters.
Fig. 1. Influence of temperature on SC yield Reaction
conditions: SO (10 mmol), [MBNT]Br (3 mol%), CO2 (5 atm),
24 h.
Commonly, a significant issue connected with utilizing CO2 as
a reaction medium is the potential hazards of working at high
pressure. Fig. 2 shows the effect of CO2 pressure on the yield of
SC for the [MBNT]Br catalyst at 100°C for 24 h. As easily
seen, the SC yield significantly increased from 79% to 98%
when the initial CO2 pressure increased from 1 to 4 atm. Such a
positive effect of CO2 pressure on the synthesis of cyclic
carbonates from CO2 and epoxides has been reported in earlier
studies.31ꢀ33 However, a further increase in pressure did not
yield more reaction products. Therefore, 4 atm was considered
as the optimal pressure for the reaction.
Table 1. Reaction of styrene oxide with CO2
utilizing various catalystsa
Entry
Catalyst
Catalyst
(mol%)
Yield
(%)b
Selectivityb
(%)
1
2
3
4
5
6
Nicotine
[MBNT]Cl
[MBNT]Br
[DBNT] Br
[MBNT] Br
[MBNT]Br
3
3
3
3
5
2
40
86
98
2
81
93
99
3
98
81
99
91
a
Reaction conditions: SO (10 mmol), CO2 (5 atm), 24 h,
120°C, solventless
bDetermined by GC using an internal standard technique.
Subsequently, the effects of the catalyst loading on the SC
synthesis were investigated. It can be observed that the SC
yield decreased from 98% to around 81% with catalyst loading
decreasing from 3 to 2 mol% (Table 1, entry 6 ), while the SC
yield remained almost constant when the catalyst loading was
increased to 5 mol% (Table 1, entry 5 ). As a consequence, 3
mol% was chosen as the most suitable catalyst loading.
As shown in Fig. 1, the temperature had a pronounced positive
influence on the cycloaddition reaction when it varied from 80
to 100°C. The SC yield was increased from about 71% to above
98% correspondingly, whereas it remained almost unchanged in
the temperature range from 100 to 120°C. Conclusively, 100°C
could be the optimal temperature for SC synthesis.
Fig. 2. Influence of the CO2 pressure on the yield of SC. SO (10
mmol), cat. amount (3 mol%), 100°C, 24 h.
The dependence of SC yield on reaction time was also
evaluated. It was observed that reaction time had a remarkable
effect on the reaction. As shown in Fig. 3, the reaction
proceeded rapidly within the first 4 h, and almost quantitative
yield (98%) could be achieved, while the reaction rate remained
almost invariant after 4 h. Therefore, a reaction time of 4 h was
appropriate for the synthesis of cyclic carbonate in this study.
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Table 2. Coupling of CO2 with various epoxides
catalyzed by [MBNT]Bra
Entry
Epoxide
Yield (%)b
Selectivity (%)
1
2
96
98
93
98
97
99
3
Fig. 3. Influence of the reaction time on the yield of SC for
[MBNT]Br (3 mol%), at 100°C and CO2 pressure of 4 atm.
4
5c
6
12
17
95
71
79
99
Experiments were performed to test the reusability of the
[MBNT]Br catalyst under the optimum conditions. The catalyst
was recovered after separation of product from the reaction
mixture by distillation under reduced pressure and then used for
the next run under the identical conditions.27i,34 As shown in
Fig. 4, there was no significant drop in SC yield after four runs,
which indicated a high stability and reusability of the catalyst.
aReaction conditions: SO (10 mmol), catalyst (3
mol%), 100°C, CO2 (4 atm) 4 h, solventless.
b Isolated Yield
c
Reaction conditions: SO (10 mmol), catalyst (3
mol%), 100°C, CO2 (5 atm) 24 h, solventless.
38ꢀ40
Based on previous reports
and the obtained results, We
proposed a plausible mechanism for the coupling of epoxides
with CO2 using the [MBNT](Br) as a catalyst, as shown in
Scheme 3. Firstly, the tertiary nitrogen atom coordinates
42
reversibly with CO2 to afford the carbamate salt,41,
which
could be an activated form of CO2. In parallel, the nucleophilic
attack of bromide anion on the less sterically hindered carbon
atom of the epoxide produces the ringꢀopened intermediate 1.
Fig. 4. The reusability results of the [MBNT]Br catalyst
Reaction condition: SO (10 mmol), catalyst (3 mol%), 100°C, 4
h, CO2 (4 atm).
Then, nucleophilic attack of the intermediate
carbamate salt furnishes the alkyl carbonate anion
1
2
on the
. Finally,
Under the optimal reaction conditions, a series of epoxides
were explored for the cyclic carbonates synthesis in the
presence of [MBNT]Br. and the results are depicted in Table 2.
The catalyst was found to be applicable to various terminal
epoxides to provide the corresponding cyclic carbonates in high
yields with excellent selectivity (up to 98%), while internal
cyclohexene oxide exhibits the lowest activity (Table 2, entry
4) even at elevated pressure and prolonged reaction time (Table
2, entry 5) probably due to steric hindrance as also illustrated
by other authors.35ꢀ37
subsequent intramolecular ringꢀclosure would form the cyclic
carbonate and regenerate the [MBNT](Br) catalyst.
Conclusions
ammonium salts based on nicotine proved to be highly efficient
and recyclable catalysts for the synthesis of cyclic carbonates
from epoxides and CO2 without utilizing any coꢀcatalyst and
coꢀsolvent. It was found that monobenzylnicotinum salts
showed much better catalytic performance, which could
activate CO2 through the tertiary nitrogen in the cation part. In
addition, the catalyst can be recovered and reused four times
without any significant loss of its initial activity.
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Calcd for C17H21BrN2; C, 61.27; H, 6.33; N, 8.41. Found (%):
C, 61.39; H, 6.67; N, 8.23.
[DBNT](Br2): Amounts of 5 mmol of (±)ꢀnicotine with an
excess of benzyl bromide were mixed under solventꢀfree
conditions and the reaction mixture was heated at 70°C for 12
h, and the precipitate was filtered off, washed with ether and
dried. Mp: 211ꢀ213°C 1HNMR(400MHz, DMSO) δ 9.60 (s,
1H), 9.38 (d, J = 6 Hz, 1H), 9.03 (d, J = 8 Hz, 1H), 8.43 (dd,
J1=8 Hz, J2 = 6 Hz, 1H), 7.47–7.63 (m, 10H), 5.96 (s, 2H), 5.35
(t, J=10.8 Hz, 1H), 4.69 (d, J = 12 Hz, 1H), 4.35 (d, J = 12 Hz,
1H), 3.36 (s, 3H), 2.50–2.74 (m, 2H), 2.15–2.30 (m, 2H), 1.27–
1.32 (m, 2H) ppm. 13CNMR (100 MHZ, DMSO) δ 148.20,
147.56, 146.15, 133.82, 132.91, 132.47, 130.30, 129.48,
129.22, 128.96, 128.37, 74.57, 65.16, 63.77, 62.94, 41.23,
25.58, 18.69 ppm. Anal. Calcd for C24H28Br2N2; C, 57.16; H,
5.6; N, 5.55. Found (%): C, 57.10; H, 5.35; N, 5.63.
General procedure for the cycloaddition reaction
All the cycloadditions were conducted in a 100 mL stainlessꢀ
steel reactor equipped with a magnetic stirrer under a CO2
atmosphere and the reactor was put into a bath of 100°C and
then pressurized to the appropriate pressure with CO2. In the
typical procedure, [MBNT]Br (3 mol%), 1,2ꢀdichlorobenzene
(internal standard of GC) and 10 mmol of styrene oxide (SO)
were added into the reactor. Then, the atmosphere inside the
reactor was replaced with CO2 and the pressure was adjusted to
4 atm at 100°C and the stirrer was started. After 4 h, the reactor
was cooled to room temperature, and the excess of CO2 was
gradually released, and the mixture was evaporated in vacuum.
The residuals were purified by silica gel column
chromatography (eluent: ethyl acetate) to give the
corresponding cyclic carbonate. The cycloaddition products are
known compounds and were characterized by comparing their
Scheme 2 The proposed mechanism for coupling reaction
catalyzed by [MBNT]Br.
Exprimental
General
Commercial reagents were purchased from Merck Company
and used without further purification. CO2 of a purity of
99.99% was commercially available. 1H NMR spectra were
recorded on a Bruker 250 and 400 spectrometers using TMS as
an internal standard in CDCl3 or DMSO. Elemental analyses
were performed by using a Leco, CHNSꢀ932 elemental
analyzer. Mass spectra were recorded on a Shimadzu QP 1100
BX Mass Spectrometer and FTꢀIR spectra were obtained as
KBr pellets on a JASCO 680ꢀPlus spectrophotometer. Melting
points were measured with a Gallenkamp melting apparatus.
Thermal analysis comprising TG and DSC for samples were
obtained using STA system, model 409 PC Luxx under a flow
of nitrogen at a rate of heating of 10°C minꢀ1 up to 600°C. Gas
chromatography (GC) (BEIFIN 3420 gas chromatograph
1
IR, ESIꢀmass, H and 13C NMR spectra with those found in the
literature.43ꢀ45
Acknowledgements
equipped with a flame ionization detector and a Varian CP SIL We gratefully acknowledge the funding support received for
this project from the Isfahan University of Technology (IUT),
IR Iran (A.R.H.) and Grant GM 33138 (A.E.R.) from the
National Institutes of Health, USA. Further financial support
from the Center of Excellence in Sensor and Green Chemistry
Research (IUT) is gratefully acknowledged.
5CB column: 30 m, 0.32 mm, 0.25 mm) were used for
consideration of reactions conversions and yields.
Catalysts Preparation and Characterization
[MBNT](Br): 5 mmol of benzyl bromide was added to a
solution of (±)ꢀnicotine (5 mmol) in MeCN (5 mL). the reaction
mixture was heated at 70°C for 12 h under reflux. The
precipitate was filtered off, washed with ether and dried.
[MBNT](Br) was obtained in quantitative yield. [MBNT](Cl)
was also synthesized using benzyl cholride by a similar
procedure. [MBNT](Br): Mp: 220ꢀ222°C 1HNMR(400MHz,
CDCl3) δ 9.34 (d, J=6 Hz, 1H), 9.28 (s, 1H), 8.2 (d, J=7.6Hz,
1H), 7.4ꢀ7.47 (m, 1H), 6.97ꢀ7.07 (m, 5H), 5.92 (s, 2H), 4.69 ((t,
J=12Hz, 1H), 3.01 (s, 3H), 2.05ꢀ2.14 (m, 2H), 1.85ꢀ1.88 (m,
2H), 1.45ꢀ1.65(m, 1H) ppm. 13CNMR (100 MHZ, CDCl3) δ
143.83, 143.67, 143.39, 132.47, 129.52, 129.28, 129.22,
129.18, 66.53, 63.74, 56.22, 40.12, 35.61, 26.23 ppm. Anal.
Notes and references
a
Pharmaceutical Research Laboratory, Department of Chemistry,
Isfahan University of Technology, Isfahan 84156, IR Iran. Corresponding
Author Tel.: +98 313 391 3262; fax: +98 313 391 2350.Eꢀmail address:
haji@cc.iut.ac.ir
b Department of Neuroscience, University of Wisconsin, Medical School,
1300 University Avenue, Madison, 53706ꢀ1532, WI, USA
c
Department of Chemistry, Faculty of Science, Shahid Beheshti
University, G. C., Evin, Tehran 1983963113, Iran
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Graphical abstract
Ammonium salts based on nicotine proved to be highly
efficient and recyclable catalysts for the synthesis of cyclic
carbonates from epoxides and CO2 without the utilization of
any organic solvent and any additives.
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