G-C3N4 and tetrabutylammonium bromide catalyzed efficient conversion of epoxide to cyclic carbonate under ambient conditions

Article abstract of DOI:10.1039/c7nj03720a

A g-C₃N₄ and n-Bu₄N⁺Br^- combination is used for the first time for the conversion of epoxides to cyclic carbonates under CO₂ filled balloon conditions. This combination was found to be very

Full text of DOI:10.1039/c7nj03720a

View Article Online
View Journal
NJC
Accepted Manuscript
This article can be cited before page numbers have been issued, to do this please use: V. Mahalingam
and T. Biswas, New J. Chem., 2017, DOI: 10.1039/C7NJ03720A.
Volume 40 Number
1
January 2016 Pages 1–846
This is an Accepted Manuscript, which has been through the
Royal Society of Chemistry peer review process and has been
accepted for publication.
NJC
New Journal of Chemistry
www.rsc.org/njc
A journal for new directions in chemistry
Accepted Manuscripts are published online shortly after
acceptance, before technical editing, formatting and proof reading.
Using this free service, authors can make their results available
to the community, in citable form, before we publish the edited
article. We will replace this Accepted Manuscript with the edited
and formatted Advance Article as soon as it is available.
You can find more information about Accepted Manuscripts in the
author guidelines.
Please note that technical editing may introduce minor changes
to the text and/or graphics, which may alter content. The journal’s
standard Terms & Conditions and the ethical guidelines, outlined
in our author and reviewer resource centre, still apply. In no
event shall the Royal Society of Chemistry be held responsible
for any errors or omissions in this Accepted Manuscript or any
consequences arising from the use of any information it contains.
ISSN 1144-0546
PAPER
Jason B. Benedict et al.
The role of atropisomers on the photo-reactivity and fatigue of
diarylethene-based metal–organic frameworks
rsc.li/njc

Please do not adjust margins
New Journal of Chemistry
Page 1 of 5
View Article Online
DOI: 10.1039/C7NJ03720A
Journal Name
COMMUNICATION
g-C N and Tetrabutylammonium bromide catalyzed efficient
3
4
conversion of Epoxide to Cyclic Carbonate under ambient
condition
Received 00th January
0xx,
Accepted 00th January
0xx
2
*
Tanmoy Biswas and Venkataramanan Mahalingam
2
DOI: 10.1039/x0xx00000x
www.rsc.org/
+
-
13
14
15
g-C
epoxide to cyclic carbonate conversion under CO
condition. This combination was found to be very efficient for CO
the conversion of a wide number of epoxides.
3 4 4
N and n-Bu N Br combination is used for the first time for rich polymers, natural products, ionic liquids, metalꢀcrown
1
6
17
2
filled balloon ether complexes and zeolites have been studied.
is thermodynamically very stable and kinetically very inert
2
1
8
molecule. In fact, it is very difficult to activate it and requires
high pressure and high temperature. It is necessary to develop
methods which will be efficient to perform the task at relatively
less drastic conditions. There are very few reports in the
literature about the cyclic carbonate formation under
atmospheric pressure. . Additionally, it is very challenging to
convert epoxide to cyclic carbonate through metalꢀfree
processes which are also important from the green chemistry
view point. Recently, 2d materials got huge attention due to
their excellent reactivity and surface area.
graphite carbon nitride (gꢀC ) which is finding wide uses for
CO2 absorption. The is due to the presence of amine and
guanidine groups.
mesoporous graphite carbon nitride (mpgꢀC N ) which was
2
Accumulation of excessive CO in the atmosphere is one of the
main reasons for the global warming which is becoming a
major threat to the civilization. This accumulation is caused due
to massive deforestation to provide space for living or
agriculture and excessive fossil fuel consumption for our dayꢀ
toꢀday energy requirement. Subsequently, it becomes necessary
1
9
to utilize this excess atmospheric CO in order to control the
climate change. It could be done through many ways such as
2
1
2
2a,b
One of them is
chemical synthesis or fuel production by utilizing the
3
N
4
2
atmospheric CO2. Catalytic method for the preparation of
2
2(cꢀi)
cyclic carbonate from epoxide has been extensively studied.
Cyclic carbonates are very useful materials as highly polar
aprotic solvents, monomers of polycarbonate, solvents for
lithium ion battery, core moiety for the synthesis of some drug
Gotterman et. al. first reported that
3
4
2
1
able to activate CO molecule. Consequently, the activation
of CO and its utilization were further studied.
is able to oxidize benzene to phenol utilizing CO as the oxygen
source. In another report Huang et al. reported the porosity
dependent epoxide to cyclic carbonate conversion by mgꢀ
2
2
2(cꢀi)
mpgꢀC N
3 4
2
3
molecules, etc. Industrial methods involve use of 1,2ꢀdiol and
2
2
3
phosgene as the C1 source for the preparation of cyclic
carbonates. However, phosgene is quite toxic as well as the
byproducts of the reaction like hydrochloric acid and waste
solvents dispersed in nature. Thus the production of cyclic
carbonate from epoxide and CO in a solvent free condition is
interesting as it is a completely green process. There are quite a
few reports on the conversion of epoxide into cyclic carbonates.
For example, salenꢀmetal complexes, metalloporphyrins,
2
4
C N . Besides that quaternary ammonium halides are well
established as coꢀcatalyst for epoxide to cyclic carbonate
3
4
4
1
1
2
conversion. In fact, the soluble quaternary ammonium cations
help to activate the epoxide molecule by the oxygen atom
whereas the nucleophilic halide counterpart attacks the epoxide
and subsequently opens up the three member ring. In addition,
there are some binary catalysts combination were also reported
5
6
2
5
7
8
metal organic frameworks, immobilized catalysts, modified
9
10
6
molecular sieves,
ionꢀexchange resins,
quaternary
12
where quaternary ammonium halides acts as coꢀcatalyst. This
reactivity of both gꢀC N and quaternary ammonium bromide
1
1
ammonium salts, quaternary phosphonium salts, nitrogen
3
4
motivate us to check whether their combination provides
improved catalytic activity for the epoxide to cyclic carbonate
conversion synergistically. We expect such combination would
result in better catalytic activity for CO2 absorption and
conversion. Our hypothesis is reasonable as gꢀC N helps to
3
4
achieve CO2 absorption and tetrabutylammonium bromide
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 1
Please do not adjust margins

Please do not adjust margins
New Journal of Chemistry
Page 2 of 5
View Article Online
DOI: 10.1039/C7NJ03720A
COMMUNICATION
Journal Name
(TBAB) facilitates the epoxide ring opening through the The decrease in temperature decreased the reaction rate and
nucleophillic attack by the bromide anion. consequently, the conversion was reduced (entry no 7, 10 and
In this work, we have reported a synergistic approach for the 11). The optimum reaction time for the conversion is found to
conversion of epoxide to cyclic carbonate at ambient pressure be 20 h (entry 7 and 8). Also, variation in the amount of gꢀ
using both gꢀC
using CO filled balloons (see Fig.S1 for the experimental 2 and 3). These results suggest that the observed efficient
setup). A variety of epoxides has been converted into cyclic catalytic activity is due to the combined effect of both gꢀC
carbonates using this approach with high reaction yield. and TBAB. It is also clear from the Table 1 that our catalyst
combination is even better then KBrꢀ(18ꢀcrownꢀ6) complex
was synthesized by heating (entry no 12). The above study suggests that entry no. 7 as the
melamine (10 g) in a semiꢀsealed alumina crucible at a optimum condition and this catalyst combination was used to
3
N
4
and TBAB. All the reactions were performed
3 4
C N (without TBAB) hardly affected the conversion (entry no
2
3
N
4
3 4
In a typical procedure, gꢀC N
o
26
temperature of 550 C for 4 hours. The resulting yellow check the activity of other substrates.
product was powdered by grinding and characterized. This
product was used for catalysis without any further modification. The study was extended to check the efficiency of the
TBAB was used as received. All epoxides were used as combined catalysts towards other epoxides. The results are
received.
shown in Table 2. It was found that our catalyst is active for
many epoxides under CO2 filled balloon pressure. Complete
The PXRD pattern contains two different peaks at 27.5° and conversion was achieved for substrates like epichlorohydrin,
3.1° indicating the planes (002) and (100), respectively. The styrene oxide, phenyl glycidyl ether and allyl glycidyl ether
peak at 2 value 27.5° indicates the graphitic stacking between (entry no. 13, 14, 15 and 16). We believe, the complete
the planes of gꢀC3N4 moiety whereas the peak observed at conversion is likely due to the presence of highly electron
1
θ
2
6
1
3.1° is assigned to the structural packing plane (see Fig. S2).
withdrawing atoms like oxygen and chlorine. In addition,
The material was further characterized by thermogravimetric styrene oxide have its inductive (–I) effect which helps to
1
3
analysis (TGA), solid state C (CP MAS) and Fourier stabilize the electron rich intermediates. The other three
transformation infrared spectroscopy (FTIR). TGA shows that substrates, i.e. 1,2ꢀepoxyꢀ9ꢀdecene, 1,2ꢀepoxy octane and 1,2ꢀ
the material is stable up to 550°C and it decomposes completely epoxy hexane (entry no. 17, 18 and 19) did not show complete
2
2c
after 615°C (see ESI Fig. S3). The chemical environment of conversion. However, the observed conversion was high (67ꢀ
1
3
the carbon atom was verified by C CP MAS. The higher 83%) particularly for ambient reaction pressure. It may be due
intensity at 164 ppm assigned to carbon having CꢀNH , The to the presence of all carbon atoms which are electron rich and
2
other peak at 156 ppm corresponds to the carbon atom attached provides +I effect. The absence of any conversion for
to the heptazine unit attached with the bridging nitrogen atoms cyclohexane oxide is likely due to the less reactive nature (entry
2
2d
(
see ESI Fig. S4). The conversion from melamine to gꢀC N
no. 20). We presume, it may be due to symmetric nature which
3
4
1
1e
was further verified by FTIR analysis. Melamine shows strong results in the more steric hindrance around the epoxide ring.
ꢀ1
NꢀH stretching in the region around 3000ꢀ3700 cm . The sharp
peaks are disappeared and observed broad peak for the sample
after conversion into gꢀC N . In addition, the peak
corresponding to 1225ꢀ1645 cm indicates the stretching of the
heterocycles containing CꢀN. (see ESI Fig. S5).
Table 1: Screening for the optimum catalyst combination under
different reaction conditions
:
3
4
1
ꢀ
2
2e
Entry
Catalysts
Time & Temp. Conversion
To understand the catalytic efficiency of the combined catalyst
gꢀC N /TBAB), we considered epichlorohydrin as the model
0
1
2
)
)
No Catalyst
105 C, 20 h
0%
(
3
4
0
gꢀC
gꢀC
3
N
4
(50 mg)
105 C, 20 h
13 %
substrate for the conversion of CO to cyclic carbonate. We
2
0
3
4
)
)
3
N
4
(100 mg)
105 C, 20 h
19 %
28 %
have optimized the reaction conditions by varying temperature,
catalyst amount and reaction time. The results are summarized
in Table 1. It is clear that use of gꢀC N or TBAB alone results
3 4
in less conversion (entry no. 2, 3, 5 and 6). However, their
combination resulted in complete conversion at ambient
pressure i.e. balloon condition (entry no. 7). This suggests that
0
gꢀC
3
N
4
(50 mg) + NaBr (7.2
mol%)
105 C, 20 h
0
5
)
TBAB (3.6 mol%)
TBAB (1.8 mol%)
105 C, 20 h
66 %
40 %
0
6)
7)
105 C, 20 h
0
gꢀC
3
N
4
4
4
4
4
(50 mg) + TBAB (1.8
mol%))
105 C, 20 h
100 %
8
)
gꢀC
3
N
(50 mg) + TBAB (1.8
mol%))
gꢀC
3
N
4
and TBAB work in a coꢀoperative way. As per our
is to absorb CO and activate
0
105 C, 12 h
70 %
55 %
90 %
57 %
understanding, the role of gꢀC
3
N
4
2
9)
0)
11)
2)
gꢀC
3
N
N
N
(50 mg) + TBAB (0.9
mol%))
0
105 C, 20 h
epoxides through hydrogen bonding. The primary function of
TBAB is to activate the epoxides through nucleophilic ring
opening by the bromide anion. To investigate the role of
TBAB, we varied the reaction conditions. From entry no 7 and
1
gꢀC
gꢀC
3
(50 mg) + TBAB (1.8
mol%)
0
90 C, 20 h
3
(50 mg) + TBAB (1.8
mol%))
0
70 C, 20 h
1
KBr (7.2 mmol) + 18ꢀcrownꢀ6
7.2 mmol)
9
(Table 1), we understand that decreasing the amount of
0
(
105 C, 20 h
50 %
TBAB led to decrease in the conversion. In fact, temperature
plays an important role in the activation of epichlorohydrin. balloon), Product conversion was calculated by H NMR analysis.
Condition: epichlorohydrin (1.5 ml, 13.7 mmol), CO
2
(99.995%,
1
2
| J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins

Page 3 of 5
NP lee wa s eJ od uo r nn oa tl aod fj uC s ht em ma ri sg it nr sy
View Article Online
DOI: 10.1039/C7NJ03720A
Journal Name
COMMUNICATION
Table 2: Conversion efficiency of g-C3N4/TBAB combined catalyst Further, the catalyst recyclability was tested by taking
for different substrates
epichlorohydrin as the substrate. The activity was checked up to
seven cycles. The activity of the catalyst combination remained
almost same which suggested the high recyclability of the
catalyst. The results are shown as bar diagram in Fig. 2.
3 4
Fig. 1. Proposed mechanism for the gꢀC N and TBAB catalyzed
epoxide to cyclic carbonate conversion.
o
o
Conditions: substrate 13.7 mmol, temp.: 105 C (entry 17, temp.: 85 C),
time 20 h, CO (99.995%, balloon), Product conversion was calculated
2
1
o
by H NMR (Fig. S6ꢀS12, ESI). Entry 16, temp. was 85 C.
The mechanism for the conversion of epoxide to cyclic
carbonate was established previously using only gꢀC N or
3
4
2
8
TBAB as coꢀcatalyst
where additionally some metal
complexes or organic molecules had been used as catalysts. We
propose the following mechanism with the knowledge from the
above literature reports. First, the nitrogen containing groups balloon), time 20 h and temp. 105 C. Product conversion was calculated
Fig.2. Recyclability study for gꢀC
3
N
4
/TBAB catalyst: Reaction
(99.995%,
condition: epichlorohydrin (1.5 ml, 13.7 mmol), CO
2
o
1
like amines and triazine assist to absorb CO effectively from by H NMR analysis.
2
the above gaseous environment (see ESI Fig. S13).
Subsequently, the primary and secondary amine groups help to
activate the epoxide via hydrogen bonding. This hydrogen
Conclusions
In conclusion, gꢀC
state thermal condensation of melamine. The combination of gꢀ
and TBAB found to an efficient catalyst for the
3 4
N was successfully synthesized by the solid
bonding again increases the electrophilicity on the carbon atom
2
2c
of the CH
2
group of the three member ring. As a result; the
3 4
C N
bromide anion present in tetrabutylammonium bromide
conversion of many epoxides into their corresponding cyclic
carbonates even at ambient pressure (balloon). Our catalyst
longevity is appreciably higher. We believe that further
functionalization of gꢀC N with CO active molecules might
3 4 2
lead to some interesting results.
(
(
TBAB) was able open up the epoxide ring at low pressure
balloon). Consequently, the epoxide moiety became negatively
charged and the tetrabutylammonium cations remain closer to it
to maintain electroneutrality. This is followed by the attack of
haloꢀalkoxide on the CO
2
molecule which results in the
incorporation of CO gas into the organic molecule. The
2
resulting carbonate ion attacks the carbon atom attached to the
bromide ions thus facilitating the elimination of the bromide
ion by an intramolecular fashion. This led to the formation of
cyclic carbonate moiety. The schematic of the proposed
mechanism is shown in Fig.1.
Acknowledgements:
MV thanks Department of Science and Technology (DST), and
Indian Institute of Science Education and Research (IISER)
Kolkata for the funding. TB thanks the UGC for his fellowship.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 3
Please do not adjust margins

Please do not adjust margins
New Journal of Chemistry
Page 4 of 5
View Article Online
DOI: 10.1039/C7NJ03720A
COMMUNICATION
Journal Name
Notes and references
1
5 (a) P. Agrigento, Syed M. A.ꢀAmsyar, B. Sorée, M.
Taherimehr, M. Gruttadauria, C. Aprile and P. P.
Pescarmona, Catal. Sci. Technol., 2014, 4, 1598–1607. (b) M.
B.ꢀSogo, H. Garcia and C. Aprile, Catal. Sci. Technol., 2015,
1
(a) Schierbaum, F. in Carbon Dioxide as Chemical Feedstock
Vol. 62 (ed. Aresta, M.) (WileyꢀVCH, 2010). (b) M. Cokoja,
C. Bruckmeier, B. Rieger, W. A. Herrmann and F. E. Kühn,
Angew. Chem., Int. Ed., 2011, 50, 8510 ꢀ 8537.
5
, 1222–1230. (c) M. E. Wilhelm, M. H. Anthofer, R. M.
Reich, V. D'Elia, J.ꢀM. Basset, W. A. Herrmann, M. Cokoja
and F. E. Kühn, Catal. Sci. Technol., 2014, 4, 1638–1643.
2
(a) A. Otto, T. Grube, S. Schiebahn and D. Stolten, Energy
Environ. Sci., 2015, 8, 3283 ꢀ 3297. (b) Q. Liu, L. Wu, R.
Jackstell and M. Beller, Nat. Commun., 2015, 6, 5933 ꢀ 5947.
1
1
1
6 W. Desens, C. Kohrt, M. Frank and T. Werner,
ChemSusChem, 2015, 8, 3815 – 3822.
(
c) A. Barthel, Y. Saih, M. Gimenez, J. D. A. Pelletier, F. E.
Kühn, V. D’Elia and J.ꢀM. Basset, Green Chem., 2016, 18,
116–3123.
3
7 C.ꢀG. Li, L. Xu, P. Wu, H. Wu and M. He, Chem. Commun.,
2
014, 50, 15764—15767.
3
(a) J.ꢀQ. Wang, J. Sun, W.ꢀG. Cheng, C.ꢀY. Shi, K. Dong, X.ꢀ
P. Zhang and S.ꢀJ. Zhang, Catal. Sci. Technol., 2012, 2, 600–
8 M. Peters, B. Kçhler, W. Kuckshinrichs, W. Leitner, P.
Markewitz and T. E. Mller, ChemSusChem, 2011, 4, 1216 –
6
05. (b) J. H. Clements, Ind. Eng. Chem. Res., 2003, 42,663–
674. (c) J. Bayardon, J. Holz, B. Schäffner, V. Andrushko, S.
1
240.
Verevkin, A. Preetz and A. Börner, Angew. Chem., Int. Ed.
,
2
007, 46, 5971–5974.
1
9 (a) Y. Xie, T.ꢀT. Wang, X.ꢀH. Liu, K. Zou and W.ꢀQ. Deng,
Nat. Commun., 2013, 4, 1960. (b) L. Wang, K. Kodama and
T. Hirose, Catal. Sci. Technol., 2016, 6, 3872–3877. (c) R.
Ma, L.ꢀN. He and Y.ꢀB. Zhou, Green Chem., 2016, 18, 226–
4
5
A.ꢀA. G. Shaikh and S. Sivaram, Chem. Rev., 1996, 96, 951 ꢀ
76.
9
2
31. (d) R. Babu, A. C. Kathalikkattil, R. Roshan, J. Tharun,
D.ꢀW. Kimb and D.ꢀW. Park, Green Chem., 2016, 18, 232–
42. (e) L. Wang, G. Zhang, K. Kodamaa and T. Hirose,
(a) J. A. C.ꢀOsma, M. North, W. K. Offermans, W. Leitner
and T. E. Mìller, ChemSusChem, 2016, 9, 791 – 794. (b) S.
Bhunia, R. Ali Molla, V. Kumari, S. M.l Islam and A.
Bhaumik, Chem. Commun., 2015, 51, 15732ꢀ15735.
2
Green Chem., 2016, 18, 1229–1233. (f) X. Liu, S. Zhang, Q.ꢀ
W. Song, X.ꢀF. Liu, R. Ma and L.ꢀN. He, Green Chem., 2016,
1
8, 2871–2876.
6
7
(a) T. Ema, Y. Miyazaki, J. Shimonishi, C. Maeda and J.
Hasegawa, J. Am. Chem. Soc., 2014, 136, 15270 ꢀ 15279. (b)
A. Chen, Y. Zhang, J. Chen, L. Chenc and Y. Yua, J. Mater.
Chem. A, 2015, 3, 9807–9816.
2
0 (a) S. Zhang and L.ꢀN. He, Aust. J. Chem., 2014, 67, 980ꢀ988.
b) L. E. Young and C. W. Porter, J. Am. Chem. Soc.,
937, 59, 1437ꢀ1438.
(
1
(a) J. Zheng, M. Wu, F. Jiang, W. Su and M. Hong, Chem.
Sci., 2015, 6, 3466 ꢀ 3470. (b) P.ꢀZ. Li, X.ꢀJ. Wang, J. Liu, J.
S. Lim, R. Zou and Y. Zhao, J. Am. Chem. Soc. 2016, 138,
2
2
1 F. Goettmann, A. Thomas and M. Antonietti, Angew. Chem.,
Int. Ed., 2007, 46, 2717–2720.
2142−2145.
2 (a) D. Li, X. Duan, H. Sun, J. Kang, H. Zhang, M. O. Tade, S.
Wang, Carbon, 2017, 115, 649ꢀ658. (b) X. Duan, H. Sun, Z.
Ao, L. Zhou, G. Wang, S. Wang, Carbon, 2016, 107, 371ꢀ
8
9
1
1
Y. Xie, Z. Zhang, T. Jiang, J. He, B. Han, T. Wu and K.
Ding, Angew. Chem., 2007, 119, 7393–7396.
3
78. (c) Q. Su, J. Sun, J. Wang, Z. Yang, W. Cheng and S.
Zhang; Catal. Sci. Technol., 2014, 4, 1556–1562. (d) J. Xu,
J.ꢀK. Shang, Q. Jiang, Y. Wang and Y.ꢀX. Li, RSC Adv.,
R. Srivastava, D. Srinivas and P. Ratnasamy, Tetrahedron
Lett., 2006, 47, 4213–4217.
2
016, 6, 55382–55392. (e) D.ꢀH. Lan, H.ꢀT. Wang, L. Chen,
C.ꢀT. Au and S.ꢀF. Yin, Carbon, 2016, 100, 81–89. (f) J. Xu,
F. Wu, Q. Jiang and Y.ꢀX. Li, Catal. Sci. Technol., 2015, 5,
0 Y. Du, F. Cai, D.ꢀL. Kong and L.ꢀN. He, Green Chem., 2005,
7, 518–523.
4
47–454. (g) J. Xu, F. Wu, Q. Jiang and Y.ꢀX. Li; Catal. Sci.
Technol., 2015, 5, 447–454. (h) Z. Huang, F. Li, B. Chen and
G. Yuan, Catal. Sci. Technol., 2016, 6, 2942–2948. (i) Y. Oh,
V.ꢀD. Le, U. N. Maiti, J. O. Hwang, W. J. Park, J. Lim, K. E.
Lee, Y.ꢀS. Bae, Y.ꢀH. Kim and S. O. Kim, ACS Nano, 2015,
1 (a) A. R. Hajipour, Y. Heidaria and G. Kozehgary, RSC Adv.
,
2
015, 5, 61179 ꢀ 61183. (b) M. Alves, B. Grignard, S.
Gennen, R. Mereau, C. Detrembleur, C. Jerome and T.
Tassaing, Catal. Sci. Technol., 2015, 5, 4636–4643. (c) T.
Ema, K. Fukuhara, T. Sakai, M. Ohbo, F.ꢀQ. Bai and J.ꢀY.
Hasegawa, Catal. Sci. Technol., 2015, 5, 2314–2321. (d) A.
Mirabaud, J. C. Mulatier, A. Martinez, J. P. Dutasta and V.
Dufaud, ACS Catal., 2015, 5, 6748−6752. (e) X. Wang, Y.
Zhao, K. Kodama and T. Hirose, J. Appl. Polym.
Sci., 2017, 134, 45189.
9
, 9148–9157.
2
2
2
2
3 M. B. Ansari, B.ꢀH. Min, Y.ꢀH. Mo and S.ꢀE. Park, Green
Chem., 2011, 13, 1416–1421.
4 Z. Huang, F. Li, B. Chen, T. Lu, Y. Yuan and G. Yuan, Appl.
Catal., B, 2013, 136, 269–277.
12 (a) H. Bittner, J. Steinbauer, and T. Werner, ChemSusChem,
5 M. North and R. Pasquale, Angew. Chem. Int. Ed., 2009, 48,
2
2015, 8, 2655 – 2669. (b) P. K. Khatri, S. L. Jain and K. T.
946 –2948.
Lim, Tetrahedron Lett., 2013, 54, 6648–6650.
6 X. Wang, K. Maeda, A. Thomas, K. Takanabe, G. Xin, J. M.
Carlsson, K. Domen and M. Antonietti, Nat. Mater., 2009, 8,
7
13 G. Ji, Z. Yang, H. Zhang, Y. Zhao, B. Yu, Z. Ma and Z. Liu,
Angew. Chem. Int. Ed., 2016, 55, 1 – 6.
6 – 80.
1
4 (a) S. Sopena, G. Fiorani, C. Martin and A. W. Kleij,
ChemSusChem, 2015, 8, 3248 ꢀ 3254. (b) L. M.ꢀRodriguez, J.
O. Garmilla and A. W. Kleij, ChemSusChem, 2016, 9, 1 – 8.
4
| J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins

Page 5 of 5
New Journal of Chemistry
View Article Online
DOI: 10.1039/C7NJ03720A
Table of Content
g-C N and Tetrabutylammonium bromide catalyzed efficient conversion
3
4
of Epoxide to Cyclic Carbonate under ambient condition
Tanmoy Biswas and Venkataramanan Mahalingam*
Department of Chemical Sciences, Indian Institute of Science Education and Research
(IISER) Mohanpur, Kolkata, West Bengal 741252, India.
E-mail: mvenkataramanan@yahoo.com; Fax: 91-33-25873020; Tel: +91(0)9007603474.
+
-
g-C N and n-Bu N Br combination found to be an efficient catalyst for the conversion of
3
4
4
epoxide into cyclic carbonate under CO filled balloon condition.
2