Cellulose (2016) 23:2539–2548
DOI 10.1007/s10570-016-0955-5
ORIGINAL PAPER
The oxidation of viscose fiber optimized by response surface
methodology and its further amination with PEI for CO2
adsorption
Hui He . Xunan Hou . Beibei Ma .
Linzhou Zhuang . Chuanfa Li .
Shihong He . Shuixia Chen
Received: 15 September 2015 / Accepted: 6 May 2016 / Published online: 17 May 2016
Ó Springer Science+Business Media Dordrecht 2016
Abstract Viscose fiber was oxidized with sodium
periodate to prepare a reactive dialdehyde viscose
fiber (DAVF) containing abundant aldehyde groups. A
solid amine adsorbent (DAVF-PEI) with high amino
density for CO2 capture was then prepared by
modifying DAVF with polyethylenimine (PEI).
Response surface methodology (RSM) based on a
three-level, three-factorial design was used to optimize the synthesis conditions of DAVF, in which
multiple linear regression equations of aldehyde
content and fiber mass loss degree were constructed.
The well-designed DAVF was then employed as a
support to graft with PEI via Schiff base reaction to
prepare a solid amine fiber (DAVF-PEI) for CO2
adsorption. The experimental results verified that
DAVF-PEI possessed good thermo-stability and high
CO2 adsorption capacity (4.11 mmol/g). DAVF-PEI
also showed promising regeneration performance,
Electronic supplementary material The online version of
this article (doi:10.1007/s10570-016-0955-5) contains supplementary material, which is available to authorized users.
H. He X. Hou B. Ma L. Zhuang C. Li S. He S. Chen (&)
PCFM Lab, School of Chemistry and Chemical
Engineering, Sun Yat-Sen University,
Guangzhou 510275, People’s Republic of China
e-mail: cescsx@mail.sysu.edu.cn
S. Chen
Materials Science Institute, Sun Yat-Sen University,
Guangzhou 510275, People’s Republic of China
which could maintain almost the same adsorption
capacity for CO2 after ten adsorption and desorption
recycles.
Keywords Dialdehyde viscose fiber Response
surface methodology PEI CO2 adsorption
Introduction
Global warming is mainly attributed to an increasing
atmospheric levels of CO2 arising from the unrestrained burning of fossil fuels (Deanna et al. 2010; Li
et al. 2010; Siriwardane et al. 2001; Zhao et al. 2013).
In order to make the separation process energyefficient, cost-effective, and available over a relatively
wider range of temperatures and pressures, many solid
adsorbents have been developed (Gray et al. 2005;
Harun et al. 2012; Sayari et al. 2011; Zukal et al. 2009;
Schrier 2012). Particularly, the amine-modified adsorbents using porous materials as substrates have been
considered as the most promising adsorbents, as their
large specific surface areas and pore volumes are
favorable to enhancing the CO2 adsorption capacity
(Drese et al. 2009; Pevida et al. 2008; Hicks et al.
2008; Wang et al. 2012; Serna-Guerrero and Sayari
2010). The CO2 adsorption capacity of the adsorbents
mainly depends on the amine loading amount and the
pore volume of the porous substrates. However, the
increase of amine loading will block the pores of the
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2540
adsorbents, thus reducing the CO2 adsorption capacity. So it is significant to develop alternative substrates
to overcome the above defect.
Many works advocating the usage of fibrous
adsorbents for CO2 adsorption have been published
by our group. Unlike porous adsorbents, fiber-based
adsorption materials possess the superior properties of
a large external surface area, short transit distance, low
pressure drops, and flexibility, which make the fiber a
promising substrate for CO2 adsorbents (Yang et al.
2010; Zhang et al. 2008; Zhuang et al. 2013; Wu et al.
2014). Besides the substrate, the amine content is also
an important factor affecting the CO2 adsorption
performance of the material. Because of its high amine
content, PEI has been widely reported to modify
materials used for gas separation. Wu et al. (2014)
grafted acrylamide onto the surface of a polypropylene
fiber and subsequently modified it with PEI to make a
novel kind of solid amine fibrous adsorbent, which
showed an adsorption capacity of 5.91 mmol/g.
Although these solid amine fibers show great performance on CO2 adsorption, their harsh synthesis
conditions still set restrictions on their large-scale
applications. The preparation of solid amine fibers
generally requires two steps including grafting and
amination, and the amination step needs to be carried
out under high temperature, which significantly
increases the energy cost. Thus, the development of
a simpler and lower energy cost preparation route will
be beneficial to improve the synthesis of solid amine
adsorbents.
Dialdehyde cellulose, obtained by cellulose oxidation using sodium periodate (Calvini et al. 2006;
Sirvio et al. 2011; Wu and Kuga 2006; Li et al. 2011),
is able to directly react with amino reagents under low
temperature for high reactivity of the aldehyde group,
which not only simplifies the preparation process, but
also reduces the production energy consumption.
Thus, dialdehyde cellulose is a kind of potential
fibrous substrate (Potthast et al. 2007). However, the
high temperature and sodium periodate concentration
can make the cellulose or dialdehyde cellulose
degrade. In the preparation process, the crystallinity
of the oxidized cellulose and the yield will both
decrease with increasing oxidation level (Kim et al.
2004; Liu et al. 2012a, b). However, one major
problem now is the absence of the available information concerning the optimization of the preparation
conditions and the kinetics of viscose fiber (VF)
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Cellulose (2016) 23:2539–2548
oxidation by sodium periodate. The detailed study on
the optimization of the VF oxidation thus becomes the
priority.
The conventional reaction condition optimization
technique is called one-variable-at-a-time. Its major
disadvantage is that it does not include the interactive
effects among the variables studied. Therefore, it does
not depict the complete effects of the parameters on
the response (Bezerra et al. 2008). In order to
overcome this weakness, the response surface methodology (RSM) is adopted, as it could be well applied
even though responses or sets of responses are
simultaneously influenced by several variables (Liu
et al. 2012a, b). RSM could not only describe the
behavior of the objective well, but also make the
statistical previsions to attain the best system
performance.
In this work, the factors affecting viscose fiber
oxidation were investigated with RSM. Optimized
dialdehyde viscose fiber (DAVF) was employed as a
support to load PEI via Schiff base reaction to prepare
a novel solid amine fiber (DAVF-PEI) for CO2
adsorption. The effect of the grafting monomer,
adsorption performance, and regeneration ability of
DAVF-PEI were also studied.
Experimental section
Materials and reagents
Viscose fiber (VF) was provided by Jihua Group Ltd.,
China. Branched polyethylenimine (PEI, Mw = 600)
was purchased from Aladdin. The others, including
sodium periodate, oxammonium hydrochloride,
sodium acetate, and ethanol with analytic reagent
grade were purchased from Guangzhou Reagent Co.
Deionized water was used to prepare all solutions in
the study.
Experimental design
The preparation of DAVF was rationally designed
using RSM of three factors, including reaction time,
reaction temperature, and sodium periodate concentration, and for the purpose of statistical computations,
the three independent variables were denoted as x1, x2,
and x3, respectively. The design was composed of
three levels (low, medium, and high, being coded as
Cellulose (2016) 23:2539–2548
2541
-1, 0, and ?1), and a total of 20 runs were carried out
in duplicate to optimize the level of the chosen
variables. According to the preliminary experiments,
the range and levels used in the experiments are
selected and listed in Table 1.
Preparation of DAVF
In the general preparation procedures, 5.00 g VF was
added to the sodium periodate solution with a given
concentration (0.18–0.52 mol/l). After adjusting the
pH to 4, the solution was sonicated at room temperature for 20 min, followed by being placed in a
shaking bath at a certain temperature (30–72 °C) and
shaken for a desired time (1–6 h). Then, the obtained
material was washed with water several times until the
produced iodine was completely removed (sodium
thiosulfate was used to detect the presence of iodine
through the color reaction between them). Then, it was
filtered and dried at 60 °C, and the obtained oxidized
VF containing aldehyde groups was called dialdehyde
viscose fiber (DAVF).
Grafting of PEI on DAVF
DAVF (5.00 g) was added to 100 ml 10 wt% PEI
solution. The mixture was continuously stirred at
45 °C for 24 h. After the reaction, the obtained
material was stirred in 60 % aqueous ethanol for 2 h
and washed with water until neutral. It was then
extracted with ethanol for 12 h and dried at 60 °C, as
illustrated in Scheme 1, DAVF loading PEI adsorbent;
DAVF-PEI was thus obtained.
Determination of the aldehyde content
DAVF (0.10 g) was placed in a 250-ml beaker
containing 1.39 g NH2OHHCl and 100 ml of 0.1 M
sodium acetate buffer (pH 4.5). The beaker was
covered with a thin rubber foil. The mixture was
stirred for 48 h at room temperature with a magnetic
Table 1 Independence
factors and corresponding
levels used for optimization
stirrer. The reaction product, an oxime derivate of
DAVF, was filtrated, washed with deionized water,
and then dried at 60 °C; the nitrogen content of the
oxime derivate of DAVF was determined through
elemental analysis (EA). As illustrated in Scheme 2,
the aldehyde contents of DAVF were determined
based on the oxime reaction between the aldehyde
group and NH2OHHCl, in which aldehyde groups
were stoichiometrically converted into oxime groups
(Sirvio et al. 2011).
Determination of the mass loss degree of fiber
The fiber mass loss degree (L, %) was obtained by
calculating the difference of the weights of viscose
fibers before (m0, g) and after (m, g) the oxidation
reaction, as presented in Eq. (1).
L ¼ ðm0 mÞ=m0 100 %
ð1Þ
Physical and chemical characterization
Infrared (IR) spectra (Tensor-27 spectrometer), elemental analysis (Elementar, Vario EL), 400-MHz
solid state 13C NMR analysis (AVANCE AV, Bruker),
and X-ray photoelectron spectroscopy (ESCALAB
250, Thermo-VG Scientific) were used to confirm the
structure of the polymers.
CO2 adsorption experiment
Breakthrough curves were used to characterize the
CO2 adsorption performances of all samples; 1.00 g
DAVF-PEI sample was tightly placed in an adsorption
column (U = 1.3 cm), into which a dry nitrogen flow
was introduced at a flow rate of 30 ml/min for 0.5 h to
remove air and excess water in the tube. Then, the dry
CO2/N2 mixed gas was introduced through the tube at
a flow rate of 30 ml/min. The inlet/outlet concentrations of CO2 were analyzed every 2 min using a
Techcomp 7900 gas chromatograph equipped with a
Variables
Real values of coded levels
-1
Reaction time, x1(h)
Reaction temperature, x2(°C)
Sodium periodate concentration, x3(mmol/g)
0
?1
3
4
5
30
45
60
0.25
0.35
0.45
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Cellulose (2016) 23:2539–2548
Scheme 1 Reaction
between DAVF and PEI
Scheme 2 Reaction
between DAVF and
NH2OHHCl
thermal-conductivity detector (TCD). After adsorption, pure nitrogen gas at a flow rate of 30 ml/min was
introduced through the tube at 90 °C to regenerate the
used DAVF-PEI.
The adsorption capacity was calculated as
follows:
Z t
Q¼
ðCin Ceff ÞVdt=22:4W
ð2Þ
0
where Q represents the adsorption capacity (mmol
CO2/g), t is the adsorption time (min), and Cin and Ceff
were the influent and effluent concentrations of CO2
(vol %), respectively. V is the total flow rate, 30 ml/
min; W and 22.4 are the weight of the sample (g) and
molar volume of gas (ml/mmol), respectively.
123
Results and discussion
RSM analysis of the preparation conditions
of DAVF
The optimum values of the variables are the main aim
using the response surface method. According to the
RSM analysis experimental data (the RSM experimental design matrix and corresponding experimental
responses are listed in Table S1 of the supporting
information), the optimal sodium periodate concentration, reaction temperature, and reaction time were
0.35 mol/l, 45 °C, and 4 h, respectively. The aldehyde
content of DAVF in these conditions reached
8.07 mmol/g, while the fiber mass loss degree could
Cellulose (2016) 23:2539–2548
2543
be controlled at 10.76 %. The three-dimensional
response surface plot obtained from the method
depicted an infinitive interaction between two test
parameters on the aldehyde content of DAVF and fiber
mass loss degree (Fig. 1), and the detailed analysis of
the two-factor interaction is shown in the supporting
information. We used the quadratic polynomial equation to express the response of the aldehyde content
and fiber mass loss degree, which are shown in
Eqs. (3) and (4). The results of the coefficient term for
the quadratic equation are tabulated in Table S2 and
S3 of the supporting information.
Yaldehyde content =ðmmol/gÞ ¼ 26:46514 þ 3:23349
x1 þ 0:51422 x2
Fig. 1 Interactions between preparation conditions. a, b Twofactor interaction between the sodium periodate concentration
and reaction temperature. c, d Two-factor interaction between
the sodium periodate concentration and reaction time. e, f Twofactor interaction between the reaction time and reaction
temperature
þ 89:21896 x3 0:17667
x2 x3 0:36982 x21
5:19490 103 x22
110:52123 x23
ð3Þ
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Cellulose (2016) 23:2539–2548
Yfiber mass loss degree =% ¼ 4:70929 þ 2:10884 x1
þ 0:1005 x2 þ 0:19308 x3
0:046333 x1 x2 þ 1:52500
x1 x3 þ 0:52167 x2 x3
ð4Þ
where x1 is the reaction time, x2 is the reaction
temperature, and x3 is the sodium periodate concentration. For the multiple correlation coefficient of the
regression Eqs. (3) and (4), their R-squared value and
Adj R-squared value were both[90 %, indicating the
high fitting degree of the model and the low error of
the experiment. Meanwhile, the lack of fit item had no
p value, which confirmed the validity of the two
regression equations. Besides, the larger the F value
was, the greater the significance for the Yaldehyde content
and Yfiber mass loss degree could be; therefore, according
to the F values in Table S2 and S3 provided in the
supporting information, it could be known that the
concentration of sodium periodate had the greatest
influence on the Yaldehyde content, while the influence of
the reaction temperature was minimal. The importance order of these influence factors on the influence
of Yfiber mass loss degree should be the concentration of
sodium periodate [ reaction temperature [ reaction
time. Moreover, the validity of the multiple linear
regression equations can be further verified by comparing the relative errors of the actual values and
predicted values of the aldehyde content and fiber
mass loss degree in Table S4 provided in the
supporting information, which were -4.61 to 5.92
and -5.93 to 5.89 %, respectively.
Structural characterization of DAVF and
DAVF-PEI
FT-IR spectra of VF, DAVF, and DAVF-PEI
Chemical changes of the fibers in each step were
characterized by FTIR (Fig. 2). It could be seen that
the FTIR spectrum of VF showed peaks at 3446 cm-1
(-O–H stretching), 2923 cm-1 (-C-H stretching),
1060 cm-1 (-C–O–C pyranose ring skeletal vibration), and 897 cm-1 (b-glycosidic linkages). Compared with the spectrum of the original VF fiber, the
spectrum of DAVF showed new peaks at 1160 cm-1
(-C-O stretching of the -C–O–C group),
1735 cm-1 and 1647 cm-1 (-C=O stretching), and
2891 cm-1 (-C-H stretching in aldehyde) (Kumari
123
Fig. 2 FT-IR spectra of VF, DAVF, and DAVF-PEI
and Chauhan 2014), suggesting the successful oxidation of VF. After amination with PEI, a new peak
appeared at 1630.78 cm-1, which could be ascribed to
–C=N (characteristic of imine). Moreover, a series of
characteristic adsorption peaks of DAVF-PEI
appeared at 3339.60 cm-1 (N–H stretching vibration),
2899.62 cm-1
(C–H
stretching
vibration),
1630.78 cm-1 and 1476.41 cm-1 (amine N–H deformation vibration), 1630.78 cm-1 (secondary amine),
1476.41 cm-1 (non-conjugated C–N bonds),
1422.69 cm-1 (C–N stretching vibration), and
1369.98 cm-1 (C–N stretching vibration in amines),
which also helped to verify the successful preparation
of DAVF-PEI.
13
C NMR spectra of VF, DAVF, and DAVF-PEI
The solid-state 13C NMR (Fig. 3) studies further
confirmed the chemical structures of DAVF and
DAVF-PEI. The 13C NMR spectrum of the VF had
strong peaks at 60.46 and 62.42 ppm (C-6), 72.01,
74.79, and 79.44 ppm (C-2, C-3, and C-5), 83.66 and
88.74 ppm (C-4), and 104.89 ppm (C-1), respectively
(Kumari and Chauhan 2014). For DAVF, due to the
influence of C=O, the chemical shift of the C-1 peak
had an offset and became closer to that of C-4.
Meanwhile, the absorption peaks at 65–80 ppm
became much broader, which could be attributed to
C=O (70.64 ppm) and C-2, C-3, and C-5 (72.01,
74.79, and 79.44 ppm). With respect to DAVF-PEI,
two characteristic absorption peaks appeared at
Cellulose (2016) 23:2539–2548
2545
Fig. 3 13C NMR spectra of
VF, DAVF, and DAVF-PEI
105.28 ppm (C=N) and 45–50 ppm (C–N of the
primary amine, secondary amine, and tertiary amines,
respectively), indicating the successful amination of
DAVF.
Chemical composition of VF, DAVF, and DAVF-PEI
Chemical compositions of the fibers were verified by
EA and XPS. From Table 2 it could be found that
DAVF contained no nitrogen, and after amination the
nitrogen content of DAVF-PEI increased to 19.59 %.
In the C1s spectrum of DAVF (Fig. 4a), there were
three peaks at 287.99, 286.55, and 284.92 eV, which
were attributed to the C=O, C–O–C/C–O–H, and C–C/
C–H groups, respectively. The C=O group content on
the DAVF surface was calculated to be 42.08 %,
demonstrating that a large number of aldehyde groups
Table 2 Elemental analysis of VF, DAVF, and DAVF-PEI
Materials
C/%
H/%
N/%
VF
38.80
6.59
0
DAVF
38.51
6.31
DAVF-PEI
45.53
8.51
0
19.59
were generated during the oxidation process. Moreover, the content of C–O groups, including C–O–C
and C–O–H, made up 37.50 % of the C species on the
DAVF surface. The abundant hydroxyl and ester
groups proved that VF could be selectively oxidized
by sodium periodate. The N1s spectra (Fig. 4b) could
be resolved into four peaks at 400.81 eV (7.40 %),
398.73 eV (37.28 %), 398.09 eV (45.01 %), and
399.73 eV (10.31 %); these peaks were the characteristics of imine, primary amine, secondary amine,
and tertiary amines, respectively. (Xu et al. 2015)
These data provided assertive evidence of the covalent
bonding between PEI chains and the DAVF surface.
Adsorption behavior of DAVF-PEI for CO2
Effect of aldehyde content on the adsorption
properties of DAVF-PEI
To investigate the influence of the aldehyde group
content on the adsorption performance of DAVF-PEI,
a series of DAVF samples with different aldehyde
contents (2.14–8.07 mmol/g) were prepared and
grafted with PEI and then were applied to CO2
adsorption. Figure 5a shows that with the increase of
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Cellulose (2016) 23:2539–2548
Fig. 4 XPS spectra of DAVF and DAVF-PEI. a C1s spectrum of DAVF. b N1s spectrum of DAVF-PEI
Fig. 5 Effect of aldehyde group content on nitrogen contents
(a) and adsorption capacities (b) of DAVF-PEI
Fig. 6 Breakthrough curves of CO2 adsorption on DAVF-PEI
with different nitrogen contents
aldehyde group content from 2.14 to 8.07 mmol/g, the
nitrogen content increased from 6.37 to 19.59 %,
indicating that the content of the aldehyde group
would determine the loading amount of PEI. As a
result, the CO2 adsorption capacity accordingly
increased from 1.07 to 4.11 mmol/g. The breakthrough curves presented in Fig. 6 showed that
DAVF-PEI was able to thoroughly adsorb CO2 at the
initial phase, and the effluent CO2 concentration
remained zero for a certain time before a breakthrough
occurred. Afterwards, it was observed that the higher
the aldehyde group content was, the longer time it
would take to break through. Different from the CO2
adsorption capacity, the amine utilization efficiency
increased first and reached the maximum value at an
aldehyde content of 5.13 mmol/g, and then it
123
decreased with the further increase of the aldehyde
group. This was because the reaction between PEI and
DAVF occurred mainly through the substitution of
oxygen by nitrogen and turned C=O groups into C=N
groups. With low aldehyde content, the aldehyde
groups could be far apart from one another in space so
that one PEI chain would tend to react with a small
number of aldehyde groups, leading to a low C=N
content. But as the aldehyde content exceeded
5.13 mmol/g, the surface aldehyde density became
larger, making each PEI chain react with more
aldehyde groups and resulting in a much larger C=N
content. Since the C=N groups could not react with
CO2, the effective amine sites declined, as did the
amine utilization efficiency.
Cellulose (2016) 23:2539–2548
2547
The well-designed DAVF was grafted with PEI via
Schiff base reaction to prepare a solid amine fiber
(DAVF-PEI) for CO2 adsorption. The effect of the
aldehyde content was investigated. The experimental
results indicated that DAVF-PEI possessed remarkable CO2 adsorption capacity (4.11 mmol/g) and good
regeneration properties. Our work can provide an
effective and low-energy-consumption method for the
preparation of an excellent CO2 solid amine adorbent.
Acknowledgments The authors gratefully acknowledge the
financial support provided by the National Natural Science
Foundation of China (Grant No. 51473187), Natural Science
Foundation of Guangdong Province (2014A030313192).
Fig. 7 Breakthrough curves of CO2 adsorption on fresh and
regenerated DAVF-PEI adsorbent (a) and the corresponding
CO2 adsorption capacities (b)
Regeneration performance
To satisfy the demands of practical use, the adsorbent
was processed for ten adsorption-desorption cycles,
and the results are shown in Fig. 7. After ten cycles,
the adsorption capacity of the adsorbent only slightly
decreased by 2.92 % (Fig. 7b). Furthermore, the
breakthrough curves of fresh and regenerated fibers
displayed in Fig. 6a clearly showed that the regenerated fibers exhibited nearly the same adsorption
behavior as the fresh ones. All these results confirmed
that the solid amine adsorbent DAVF-PEI could stay
stable after multiple regeneration cycles and maintain
its adsorption capacity for CO2.
Conclusions
RSM was employed to optimize the synthesis parameters of dialdehyde viscose fiber (DAVF). The
constructed multiple linear regression equations of
the aldehyde content and fiber mass loss rate can
successfully predict the VF oxidation results when
given the conditions. The optimum synthesis conditions were found to be a sodium periodate concentration of 0.35 mol/l, reaction temperature of 45 °C, and
reaction time of 4 h. Under these conditions, the
aldehyde content of DAVF can be as high as
8.07 mmol/g, while the VF fiber mass loss rate was
controlled at 10.76 %.
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