Sodium anilinide-cyclohexylamide pair: Synthesis, characterization, and hydrogen storage properties

Article abstract of DOI:10.1039/c9cc08593a

The lack of efficient hydrogen storage material is one of the bottlenecks for the large-scale implementation of hydrogen energy. Here, a series of new hydrogen storage materials, i.e., anilinide-cyclohexylamide pairs, are proposed via the metallation of an aniline-cyclohexylamine pair. DFT calculations show that the enthalpy change of hydrogen desorption (ΔH_d) can be significantly tuned from 60.0 kJ per mol-H₂ for the pristine aniline-cyclohexylamine pair to 42.2 kJ per mol-H₂ for sodium anilinide-cyclohexylamide and 38.7 kJ per mol-H₂ for potassium anilinide-cyclohexylamide, where an interesting correlation between the electronegativity of the metal and the ΔH_d was observed. Experimentally, the sodium anilinide-cyclohexylamide pair was successfully synthesised with a theoretical hydrogen capacity of 4.9 wt%, and the hydrogenation and dehydrogenation cycle can be achieved at a relatively low temperature of 150 °C in the presence of commercial catalysts, in clear contrast to the pristine aniline-cyclohexylamine pair which undergoes dehydrogenation at elevated temperatures.

Full text of DOI:10.1039/c9cc08593a

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Sodium anilinide-cyclohexylamide pair: synthesis,
characterization, and hydrogen storage properties
Zijun Jing,ab Yang Yu,ab Ruting Chen,c Khai Chen Tan,d Teng He,*a Anan Wu,*c Qijun Pei,ab Yongshen
Received 00th January 20xx,
Accepted 00th January 20xx
Chua,d Dewen Zheng,*e Xi Zhang,e Zhixin Ge,e Fudong Zhang,e and Ping Chena
DOI: 10.1039/x0xx00000x
The lack of efficient hydrogen storage material is one of the implementation at minimal modification on the existing fuelling
bottlenecks for the large-scale implementation of hydrogen energy. infrastructure12. However, the dehydrogenation of LOHCs, such
Here, a series of new hydrogen storage materials, i.e., anilinide- as benzene-cyclohexane pair (ca. Hd =73.6 kJ/mol-H2), occurs
cyclohexylamide pairs, are proposed via the metallation of aniline- at relatively high temperatures due to the unfavourable
cyclohexylamine pair. DFT calculations show that the enthalpy dehydrogenation enthalpy change, leading to a low round-trip
change of hydrogen desorption (Hd) can be significantly tuned energy efficiency. It was demonstrated theoretically and
from 60.0 kJ/mol-H2 of pristine aniline-cyclohexylamine pair to 42.2 experimentally that incorporation of heteroatoms (such as N)
kJ/mol-H2 for sodium anilinide-cyclohexylamide and 38.7 kJ/mol-H2 into aromatic ring reduced the ΔHd effectively13, 14. N-
for potassium anilinide-cyclohexylamide, where an interesting ethylcarbazole/perhydro-N-ethylcarbazole pair (NEC/12H-NEC)
correlation between the electronegaticity of the metal and the Hd with ΔHd = 53.2 kJ/mol-H2 was developed and well-investigated
was observed. Experimentally, sodium anilinide-cyclohexylamide recently15, 16. Jessop and co-workers also demonstrated that the
pair was successfully synthesised with a theroritical hydrogen dehydrogenation thermodynamics (ΔHd) can be reduced
capaicty of 4.9wt%, and the hydrogenation and dehydrogenation through attaching an electron donating group outside the
cycle can be achieved at a relatively low temperature of 150 °C in aromatic ring17. As matter of fact, phenol-cyclohexanol pair has
the presence of commercial catalysts, in clear contrast to the a Hd that is ca. 64.5 kJ/mol-H2 lower than benzene-
pristine aniline-cyclohexylamine pair which undergoes cyclohexane pair due to electron donation nature of -OH group.
dehydrogenation at elevated temperatures.
Very recently, we introduced sodium to phenol-cyclohexanol
pair, forming sodium phenoxide-cyclohexanolate pair, which
can further tune Hd to 50.4 kJ/mol-H2 and undergoes
reversible hydrogenation and dehydrogenation under mild
condition18. The continuous reduction in ΔHd from benzene to
phenol and to phenoxide correlates to the electron donating
capability of -H, -OH and -ONa to the benzene ring. To further
develop materials that have the optimal ΔHd (ca. 30-40 kJ/mol-
H2), a substituent having stronger electron donation should be
attached to the benzene ring. A straightforward strategy is to
couple the effects of both metal (alkali or alkaline earth metal)
and organic substituent which possess a stronger electron
donating ability. Herein, aniline-cyclohexylamine pair was
chosen as the pristine organic pair because the electron
donating ability of -NH2 is stronger than -OH. We then employed
metallation strategy developed by us recently to modify the -
NH2 groups and synthesized the sodium anilinide and
cyclohexylamide for the first time. To our delight, Both DFT
calculations and experimental results show that the ΔHd of alkali
anilinide-cyclohexylamide pairs can be reduced to the optimal
region, and hydrogen absorption/desorption cycle can be
realized at a temperature as low as 150°C.
The development of advanced materials for both on-board and
large-scale hydrogen storage/transportation is regarded as a
key prerequisite for the widespread implementation of
hydrogen energy1, 2. Tremendous efforts have been devoted to
solid-state hydrogen carriers, including metal hydrides3,
complex hydrides4-6 and chemical hydrides7-9, and liquid organic
hydrogen carriers (LOHCs)10, 11. Among them, LOHCs have the
great potential to meet the applications for on-board hydrogen
storage and large-scale hydrogen transportation owing to their
mass production, high hydrogen contents, reversibility in
absorbing and desorbing hydrogen and the ease of widespread
a. Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics,
Chinese Academy of Sciences, Dalian 116023, China. E-mail: heteng@dicp.ac.cn
b. University of Chinese Academy of Sciences, Beijing 100049, China.
c. Department of Chemistry, College of Chemistry and Chemical Engineering,
Xiamen University, Xiamen 361005, China. E-mail: ananwu@xmu.edu.cn
d. School of Chemical Sciences, Universiti Sains Malaysia, Pulau Pinang 11800, Malaysia.
e. New Energy Department, Research Institute of Petroleum Exploration &
Development, China National Petroleum Corporation, China, E-mail:
zdw69@petrochina.com.cn
Electronic Supplementary Information (ESI) available: [details of any supplementary
information available should be included here]. See DOI: 10.1039/x0xx00000x
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X1s method19 was employed to calculate the heats of formation of
alkali and alkaline earth metal anilinides and cyclohexylamides,
respectively. The corresponding heats of hydrogen desorption (ΔHd)
from the anilinide-cyclohexylamide pairs can be derived which are
shown in Figure 1. We also calculated ΔHd of the parent aniline-
cyclohexylamine pair and obtained a value of 60.0 kJ/mol-H2, which
agrees well with that determined experimentally (59.7 kJ/mol-H2)20.
Because -NH2 is more electron donating than -OH, the ΔHd of aniline-
cyclohexylamine pair is lower than that of the phenol-cyclohexanol
pair (64.5 kJ/mol-H2). The metallation of aniline-cyclohexylamine
pair leads substantial decrease in ΔHd as shown in Figure 1. For
instance, the ΔHd of sodium and potassium anilinide-
cyclohexylamide pairs decreases to 42.2 and 38.7 kJ/mol-H2,
respectively, and are within or close to the ideal ΔHd region for
reversible hydrogen storage. Our previous results on phenoxide-
cyclohexanolate system showed that both phenoxides and
cyclohexanolates were stabilized upon metallation. However, the
phenoxides were more stabilized than the cyclohexanolates due to
the magnitude of conjugation effect in phenoxide is significantly
greater than that of the hyper-conjugation effect in cyclohexanolate.
Similarly, in the present study, electrons on the N atom of the metallo
anilinide generate a delocalized resonance with benzene ring
forming a p-π conjugation and consequently stabilizing the aniline. In
the cyclohexylamide cases, however, the electrons on N are hard to
be delocalized. Therefore, the substantial decrease in ΔHd is resulted
in metallo anilinide-cyclohexylamide system. Since the ΔHd of
metallo anilinide-cyclohexylamide pair is related to the electron
donation from the metals, we refer to the Pauling electronegativity
of metal as an indication of the metallation effect. Interestingly, a
nearly linear relationship between ΔHd and the electronegativity can
be obtained as shown in Figure 1, suggesting that the ΔHd can be
rationally tuned by selecting different metals. It was reported that
the ΔHd of cycloalkane scales with the Hammett parameter (σ) of
substitute group13, where the Hammett parameter is a measure of
the electron-donating ability of the substituent group. The
electronegativity also reflects the ability of an atom in a molecule to
attract or donate electrons. Therefore, a correlation between the
ΔHd and the electronegativity of cation will be reasonable. Because
the sodium anilinide-cyclohexylamide pair has relatively smaller ΔHd,
high hydrogen capacity (ca. 4.9wt%) as well as the ease of synthesis,
it was chosen as an example for experimental investigation.
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DOI: 10.1039/C9CC08593A
Sodium anilinide and cyclohexylamide were synthesized via
reacting sodium hydride and aniline/cyclohexylamine through wet
chemical method and ball-milling method (see Supporting
Information), respectively. Around 1 equiv. H2 was released from
both reactions (Figure 2a), indicating the formation of sodium
anilinide and cyclohexylamide following the reactions 1 and 2.
Powder X-ray diffraction (XRD) patterns of the as-prepared samples
emerged several new peaks which cannot match with any Na-, C-, N-,
and H-containing compound in database (Figure S1).
Thermogravimetric-differential thermal analysis (TG-DTA) and
temperature-programmed desorption system equipped with a mass
spectrometer (TPD-MS) results (Figure S2 and S3) show that around
10 mol% diethyl ether is released from the as-prepared samples
during heating process, indicating adduction of the solvent
molecules to sodium anilinide. However, the removal of diethyl ether
from sodium anilinide at 90 °C would lead to an amorphous product.
Structure determination is still in process. It is worth mentioning that
hydrolysis of these two compounds may occur in humid air.
Figure 2. (a) Hydrogen evolution from sodium hydride and aniline in diethyl ether
solution. (b) 1H, (c) 13C and (d) 23Na NMR spectra of synthesized sodium anilinide and
cyclohexylamide compared with those of aniline and cyclohexylamine in DMSO-d6.
Scheme 1. The reversible reaction of sodium anilinide and cyclohexylamide.
Liquid-state 1H and 13C nuclear magnetic resonance (NMR) spectra
of the as-prepared samples in DMSO-d6 are shown in Figure 2b and
2c. Obvious upfield shifts are observed in the H NMR spectrum of
the synthesized sodium anilinide compared with that of pristine
aniline, indicating more shielding effect upon metallation, which is
Figure 1. Theoretical calculation results of ΔHd for alkali and alkaline earth metal
anilinide-cyclohexylamide pairs in gaseous phase as
a function of Pauling
1
electronegativity of metal. For the ease of illustration in the insert equation, M is in
monovalent. In case of divalent, it is understandable that twice as much anions (anilinide
and cyclohexylamide) will be needed.
2 | J. Name., 2012, 00, 1-3
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DOI: 10.1039/C9CC08593A
Table 1. Hydrogenation of sodium anilinide catalyzed by different commercial catalysts.
Selectivity a /%
DCHA
Entry
Catalysts
M%
T /°C
P /bar
t /h
C a /%
CHA
100
67
Aniline
1
2
3
4
5
6
7
8
―
―
150
150
150
150
140
140
140
150
70
70
70
70
70
70
70
70
48
90
24
8
2
0
0
0
5%Ru/Al2O3
5%Rh/Al2O3
5%Pt/C
1:10
1:10
1:10
1:15
1:19
1:30
1:10
85
33
16
56
36
40
17
0
50
84
0
>99
>99
>99
78
39
5
5%Pt/C
10
20
10
15
59
5
5%Pt/C
46
14
0
5%Pt/C
83
Na-1%Ru/TiO2
>99
100
0
M%: molar ratio of catalyst to anilinide (metal:anilinide). T: temperature. P: pressure of H2. t: time. C: conversion. CHA: cyclohexylamide. DCHA: dicyclohexylamine. a: Conversion
and selectivity were quantified by 1H NMR.
consistent with the electron donating effect of the metal. However, be reached for Ru/Al2O3 and Rh/Al2O3 catalysts even with longer
only slight shifts of 1H NMR of sodium cyclohexylamide to upfield are reaction time, respectively. However, the selectivity to the desired
detected compared with pristine cyclohexylamine, which may be due product (cyclohexylamide, CHA) on Pt/C is much lower than that of
to the absence of conjugation effect of cyclohexylamine. However, it Ru/Al2O3 and Rh/Al2O3. In order to enhance the selectivity to the
is noticeable that the signals of proton which bonded to nitrogen are desired product, the amount of catalyst, temperature and the
disappeared in the synthesized sodium anilinide and sodium reaction time were further optimized. Although lowering the amount
cyclohexylamide. This could be due to the overlapping of this N-H of catalyst would sacrifice the conversion under the same condition
peak with other peaks or the influence of the deuterated DMSO-d6 (entry 5 to 7), a higher selectivity to the desirable product could be
reagent used. The peaks of N-H of sodium anilinide and sodium retained. Delightfully, it was found that a selectivity as high as 83%
cyclohexylamide re-appear in deuterated benzene-d6 reagent (Figure to cyclohexylamide with a conversion of 78% for anilinide was
S4). Therefore, the disappearance of N-H resonance could be obtained at 140 °C in the presence of Pt/C catalyst with the molar
attributed to the hydrogen-deuterium exchange between DMSO-d6 ratio of catalyst to anilinide at 1:30. Furthermore, the formation of
and sodium anilinide or cyclohexylamide. 13C NMR spectra in Figure dicyclohexylamine (DCHA) suggests the breaking of N-Na bond in
2c show similar results to 1H NMR spectra in which electron state of anilinide or cyclohexylamide. Comparing the entries 5 to 7, it looks
anilinide is obviously changed via metallation. However, the impacts like that longer reaction time would lead to lower selectivity to
on the 13C resonances in metallo anilinide and cyclohexylamide are cyclohexylamide,
which
indicates
the
formation
of
more complicated. The C atoms close to N and at para-position show dicyclohexylamine may be from the dimerization of cyclohexylamide.
obvious chemical shifts in sodium anilinide. Meanwhile, the strong To further suppress the formation of dimer, efficient catalyst is
23Na NMR signals in sodium anilinide and sodium cyclohexylamide in needed. Here, a sodium modified-Ru/TiO2 catalyst (Na-1%Ru/TiO2)
Figure 2d suggest the replacement of H in -NH2 by Na. Combining the was developed in our group very recently, which exhibited superior
quantity of hydrogen evolution during syntheses, XRD, and NMR performance for hydrogenation of aromatics21 and was employed in
results, it is confirmed that the sodium anilinide and sodium the hydrogenation of sodium anilinide in this study. As shown in
cyclohexylamide were successfully obtained. Considering the Table 1 and Figure S7, >99% conversion of sodium anilinide and
decrease in ΔHd, hydrogen absorption and desorption of sodium selectivity to sodium cyclohexylamide were obtained. It is shown that
anilinide-cyclohexylamide pair are investigated in the following different catalysts exhibit different functions. For example, Na-
studies (Scheme 1).
1%Ru/TiO2 catalyst could enhance the reaction rate significantly.
As sodium anilinide and cyclohexylamide are both solids, different While, the other catalysts not only enhanced the activity, but also
commercial catalysts were hand-milled with these two materials to changed the selectivity.
promote hydrogenation and dehydrogenation. Hydrogenation of
Table 2. Dehydrogenation of sodium cyclohexylamide catalyzed by Rh/Al2O3 catalysts.
sodium anilinide was carried out in the absence/presence of
commercial catalysts (Pt/C, Ru/Al2O3 and Rh/Al2O3) under different
Selectivity a /%
conditions as shown in Table 1. Although the selectivity to the
desired product (CHA) is high without catalyst (entry 1), the
conversion of sodium anilinide is quite low (ca. 2%) even for 48 h.
Among these catalysts, Pt/C catalyst exhibits the best activity (entry
2 to 4), i.e., a conversion of 99% of sodium anilinide can be obtained
in less than 8 hours. In contrast, conversions of 85% and 50% can only
Catalysts
t /h
C a /%
Anilinide
NCHBA
5%Rh/Al2O3
11
>99
80
20
The molar ratio of Rhodium to cyclohexylamide is 1:10. The reaction temperature is
0 bar. t: time; C: conversion; NCHBA: N-
cyclohexylbenzenamine; a: Conversion and selectivity were quantified by 1H NMR.
150°C and the pressure is
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J. Name., 2013, 00, 1-3 | 3
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For dehydrogenation, TPD-MS results (Figure S5a) show that the Talents Program (XLYC1807157), and K. C. WoVnigew AErdticulecaOtniloinne
as-prepared sodium cyclohexylamide dehydrogenates at the Foundation (GJTD-2018-06). A. Wu acknDoOwIl:e1d0g.1e0s39t/hCe9CfCin0a8n59c3iaAl
temperature higher than 130 °C. Meanwhile, small amounts of by- support from the National Science Foundation of China (21773193).
products are detected during heating, indicating that side reactions
occurred. Then, a commercial 5% Rh/Al2O3 catalyst was employed to
catalyse the dehydrogenation of sodium cyclohexylamide.
Interestingly, the Rh-catalyzed sodium cyclohexylamide sample
starts to evolve H2 at about 80 °C and gives a broad desorption peak
Notes and references
centered at ca. 155 °C as shown in Figure S5b, which is much lower
than that of the pristine sodium cyclohexylamide. Further increasing
the temperature to 300 °C, more hydrogen can be released, which
may be due to the decomposition of the reactant. In order to
suppress the side reaction, catalytic dehydrogenation was conducted
at 150 °C which is below the temperature for producing those by-
products. As shown in Table 2, the conversion of sodium
cyclohexylamide dehydrogenation can be achieved as high as 99% in
11 hours. The selectivity to the desired product of sodium anilinide
was determined as 80%, whereas, 20% of by-product, N-
cyclohexylbenzenamine (NCHBA) was also observed (Figure S6).
Catalytic dehydrogenation is always a challenging task in organic
hydrogen carriers. Design and fabrication of novel catalyst will be
beneficial to the conversion and selectivity. Therefore, development
of efficient catalysts is highly demanded in the following
investigations.
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Nevertheless, the hydrogen uptake and release can be achieved
through the sodium anilinide-cyclohexylamide pair at the
temperature as low as 150 °C. It should be noted that the dimer by-
products (dicyclohexylamine or N-cyclohexylbenzenamine) were
always been observed during hydrogenation or dehydrogenation
(Table 1 and 2). Usually, the dimers were detected in the catalytic
12. D. Teichmann, W. Arlt, P. Wasserscheid and R. Freymann,
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hydrogenation of aniline (Scheme S1 and S2).
In summary, the thermodynamics of aniline-cyclohexylamine pair
for hydrogen storage can be manipulated via metallation strategy,
i.e., the ΔHd of cyclohexylamides correlates well with the
electronegativity of metals. Specifically, sodium anilinide-
cyclohexylamide pair with ΔHd of 42.2 kJ/mol-H2 was successfully
synthesized. The hydrogenation and dehydrogenation can be
realized at the temperature as low as 150 °C in the presence of
commercial catalysts. More importantly, because of the large
diversity of organic compounds, it could be easily broadening the
current scope of amine-based materials thus providing vast
opportunities for the further exploration.
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20. Based on liquid-phase values of ΔfH0 (C6H7N, l) = 31.3 kJ/mol and
ΔfH0 (C6H13N, l) = -147.7 kJ/mol.
21. Unpublished data. The synthesis of Na-Ru/TiO2 catalyst can be
found in experimental part.
22. H. Greenfield, J. Org. Chem., 1964, 29, 3082-3084.
Conflicts of interest
There are no conflicts to declare.
Acknowledgment
T. He and P. Chen acknowledge the supports provided by National
Key R&D Program of China (2018YFB1502100), the National Natural
Science Foundation of China (51671178, 21875246), Dalian Institute
of Chemical Physics (DICP DCLS201701), LiaoNing Revitalization
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DOI: 10.1039/C9CC08593A
Metallo anilinide-cyclohexylamide pairs with promising thermodynamic properties for
reversible hydrogen storage were successfully developed for the first time.