Properties and applications of sodium (5-methyl-2-alkyl-1,3-dioxane-5-yl)-carboxylate synthesized with nanosolid superacid

Article abstract of DOI:10.1166/jnn.2016.10628

A series of novel sodium (5-methyl-2-alkyl-1,3-dioxane-5-yl) carboxylate surfactants were synthesized using nanosolid superacid SO^2-₄ /Fe₂O₃ as a catalyst and characterized by 1H NMR, IR and elemental analysis. The critical micelle concentration (CMC) of surfactants was determined and the results showed that the CMC values were less than 2.0× 10^-3 mol/L. Other relevant surface properties (Krafft point, emulsion stability, foam ability, degradability) were also evaluated. It was suggested that with respect to emulsion formation, foam stability and the range of application temperature, compared with traditional surfactants, the new surfactants could give better results and showed better properties when used as an emulsifier in emulsion polymerization. In addition, the surfactants were stable under neutral and alkaline conditions, and could form solid under acid condition. The solid will generate the original surfactants for reuse with alkali. Sodium (5-methyl-2-alkyl-1,3-dioxane-5-yl) carboxylate is likely to be a new type of 'environmentally friendly' surfactant.

Full text of DOI:10.1166/jnn.2016.10628

Article
Journal of
Nanoscience and Nanotechnology
Vol. 16, 1085–1089, 2016
Copyright © 2016 American Scientific Publishers
All rights reserved
Printed in the United States of America
www.aspbs.com/jnn
Properties and Applications of Sodium
5-methyl-2-alkyl-1,3-dioxane-5-yl)-Carboxylate
Synthesized with Nanosolid Superacid
(
∗
Lin Yuan, Guo Kai Jia, Zhong Yan Li, Min Zhang, and Xian You Yuan
Key Laboratory of Comprehensive Utilization of Advantage Plants Resources in Hunan South,
Hunan University of Science and Engineering, Yongzhou 425199, Hunan, P. R. China
A series of novel sodium (5-methyl-2-alkyl-1,3-dioxane-5-yl) carboxylate surfactants were synthe-
2
4
−
1
sized using nanosolid superacid SO /Fe O as a catalyst and characterized by H NMR, IR and
2
3
elemental analysis. The critical micelle concentration (CMC) of surfactants was determined and
−
3
the results showed that the CMC values were less than 2ꢀ0 × 10 mol/L. Other relevant sur-
face properties (Krafft point, emulsion stability, foam ability, degradability) were also evaluated.
It was suggested that with respect to emulsion formation, foam stability and the range of appli-
cation temperature, compared with traditional surfactants, the new surfactants could give better
results and showed better properties when used as an emulsifier in emulsion polymerization.
In addition, the surfactants were stable under neutral and alkaline conditions, and could form solid
Delivered by Ingenta to: Rice University
under acid condition. The solid will generate the original surfactants for reuse with alkali. Sodium
IP: 91.204.15.80 On: Sat, 11 Jun 2016 05:56:00
(
5-methyl-2-alkyl-1,3-dioxane-5-yl) carboxylate is likely to be a new type of ‘environmentally friendly’
Copyright: American Scientific Publishers
surfactant.
Keywords: Nanosolid Superacid, Synthesis, Acetal, 1,3-Dioxane, Surfactant.
1
. INTRODUCTION
surfactants, this type of cyclic acetal (ketal) compounds
Surfactants are a special class of compounds possess-
ing important physicochemical properties. Classical sur-
factants are composed of two distinct parts, one polar and
the other nonpolar, incompatible with eath other. Because
of this amphiphilicity, surfactants tend to self-aggregate
into micelles (above a certain concentration, known as
the critical micelle concentration, CMC). This aggregation
forms the basis of many biochemical process and is advan-
tageous in different industrial areas, like cleaning, paint,
pharmaceuticals, emulision, oil recover, catalysis, microre-
possess unusual physicochemical properties and can be
used with higher efficiency in the emulsion polymeriza-
7
–11
tion and emulsion of organic reactions.
The microemul-
sion could be decomposed under acid condition, and the
products could be separated easily from two phases after
1
2–15
the reaction in presense of these novel surfactants.
Recently, we reported the synthesis and properties of
1
6
acetal sulfonate surfactant containing 1,3-dioxane. In this
paper, a new type of segregative and degradable sur-
factants containing 1,3-dioxane were synthesized by 2,2-
dihydroxymethyl propionic acid with short-chain fatty
1
–3
actor and cosmetics.
2
4
−
aldehyde, using nanosolid superacid SO /Fe O as a cat-
Due to environment concerns, the research on novel sur-
factants has been made widely in recent years. In order
to achieve the goal, a wide variety of new surfactants,
cyclic acetal (ketal) compounds, have been synthesized
and their physicochemical behaviors have been inves-
tigated. Generally speaking, compared with traditional
2
3
alyst (Scheme 1). The new surfactants were stable under
neutral and alkaline conditions, and would degrade into
the raw materials for reuse in acid environment. Moreover,
nanomaterials have been widely investigated in last few
4
–6
1
7–41
years,
and it seems that some nanomaterials work well
when used for catalytic application. Based on the above
characteristics, these surfactants are promising to be a new
∗
42–46
Author to whom correspondence should be addressed.
type of ‘green surfactants’
.
J. Nanosci. Nanotechnol. 2016, Vol. 16, No. 1
1533-4880/2016/16/1085/005
doi:10.1166/jnn.2016.10628
1085

Properties and Applications of Sodium (5-methyl-2-alkyl-1,3-dioxane-5-yl)-Carboxylate
Yuan et al.
2
–
CH OH
SO /Fe O
4 2 3
2
NaOH
O
O
O
COONa
COOH
RCHO + H C
C
COOH
R
3
R
O
CH OH
DMF
3
CH OH
2
1
a~1d
2a~2d
3a~3d
a. R = C H ; b. R = C H ; c. R = C H ; d. R = C H
7 15
4
9
5
11
6
13
Scheme 1. Synthesis of surfactants 3a∼3d.
2
. EXPERIMENTAL SECTION
(t, J = 6.8 Hz, 3 H, CH CH ꢂ; IR (KBr) ꢃ: 3001, 2953,
3
2
2
.1. Instrumentation and Materials
2862, 2644, 2349, 1692, 1460, 1407, 1325, 1258, 1216,
185, 1125, 1067, 1009, 953, 918, 871, 800, 725, 669,
1
2
.1.1. Instruments
−
587 cm ; Anal. calcd for C H O : C 59.36, H 8.90,
10 18 4
1
2
4
−
The nanosolid superacid SO /Fe O made of an amor-
2
3
Found C 59.42, H 8.87.
2b: a white solid; yield 64.0%; m.p.135.3 C; H NMR
phous solid powder was prepared according to the
ꢀ
1
literature.4
7ꢀ48
The particle size of the sample is very small
2
−1
(CDCl , 400 MHz) ꢁ: 4.51–4.53 (t, J = 4.8 Hz, 1 H,
(
≤50 nm) with large specific surface area (≥145 m ·g )
3
OCHO), 4.44–4.47 (d, J = 11.2 Hz, 2 H, OCH C, H ),
within the scope of nanoparticles. Melting point data were
recorded on a XRC-1 microscopic melting point meter,
the thermometer without correction. Element analysis was
recorded on PE2400 instrument. The IR spectra were
2
eq
3
2
1
.49–3.52 (d, J = 11.2 Hz, OCH C, H ), 1.63–1.69 (m,
2
ax
H, CHCH CH ꢂ, 1.37–1.43 (m, 2 H, CH CH CH ꢂ,
2
2
2
2
3
.30–1.31 [m, 4 H, CH (CH ) CH ], 1.05 (s, 3 H, CCH ꢂ,
2
2
2
2
3
−1
0.89–0.92 (t, J = 6.8 Hz, 3 H, CH CH ꢂ; IR (KBr)
recorded in the 4000–400 cm region using KBr pellets
and a Niconet AVATAR-360 spectrometer. H NMR spec-
tra were recorded in a CDCl and D O solution with a
VARAN UNTTY INOV-400 spectrometer. 2,2-dihydroxy
methyl propionic acid (98%, Aladdin) and all of the alde-
hyde (Aladdin) were purified by distillation before use.
Other materials and solvents were commercially available
and were used without further purification.
3
2
1
ꢃ: 2950, 2924, 2858, 2653, 1691, 1461, 1406, 1327, 1256,
1
4
161, 1127, 1070, 1020, 946, 915, 805, 722, 670, 588,
3
2
−
76 cm ; Anal. calcd for C H O : C 61.03, H 9.25,
11 20 4
1
Found C 61.11, H 9.17.
ꢀ
1
2
c: a white solid; yield 64.7%; m.p. 134.4 C; H NMR
Delivered by Ingenta t (o C: DR Ci cle, U4 n0 i0v e Mr s Hi t yz ) ꢁ: 4.49–4.52 (t, J = 5.2 Hz, 1 H,
3
IP: 91.204.15.80 On: Sat, 11 Jun 2016 05:56:00
OCHO), 4.38–4.41 (d, J = 11.2 Hz, 2 H, OCH C, H ),
2
eq
Copyright: American Scientific Publishers
3
.48–3.51 (d, J = 11.2 Hz, 2 H, OCH C, H ), 1.61–1.66
2
ax
(
m, 2 H, CHCH CH ꢂ, 1.34–1.38 (m, 2 H, CH CH CH ꢂ,
2
.1.2. General Procedure for the Synthesis of
-methyl-2-alkyl-1,3-dioxane-5-Carboxylic
Acid (2a–2d)
The method adopted for the synthesis of 5-methyl-2-butyl-
,3-dioxane-5-carboxylic acid (2a) can be described as fol-
2 2 3 2 2
1
0
.26 [m, 6 H, CH (CH ) CH ], 1.029 (s, 3 H, CCH ꢂ,
2 2 3 2 3
5
.85–0.87 (t, J = 6.8 Hz, 3 H, CH CH ꢂ; IR (KBr)
3
2
ꢃ: 2921, 2856, 2653, 1692, 1460, 1407, 1325, 1256, 1161,
1
−1
127, 1071, 945, 851, 801, 725, 670, 585 cm ; Anal.
1
calcd for C H O : C 62.55, H 9.56, Found C 62.48,
1
2
22
4
lows. 5.10 g (38.07 mmol) 2,2-dihydroxy methyl propionic
acid, 3.61 g (41.89 mmol) n-pentanal and 0.12 g nanosolid
superacid SO /Fe O were added into a mixture of N ,N -
H 9.63.
ꢀ
1
2
4
−
2d: a white solid; yield 57.2%; m.p. 134.0 C; H NMR
2
3
(
CDCl , 400 MHz) ꢁ: 4.48–4.51 (t, J = 4.8 Hz, 1 H,
dimethylformamide (10 mL) and cyclohexane (10 mL) and
refluxed for 5 h with stirring. After the reaction, sodium
bicarbonate 0.06 g (0.70 mmol) was added to the mix-
ture, and stirred at room temperature for half an hour. The
solvent was then removed under reduced pressure using a
rotary evaporator and a solid precipitated out. The isolated
solid was dissolved in cyclohexane and washed with sat-
urated salt water (10 mL×2) and water (10 mL×2), the
organic layer was dried over anhydrous magnesium sulfate
overnight. After removal of the solvent, the crude product
was purified by recrystallization from n-hexane to afford
white crystals.
3
OCHO), 4.40–4.43 (d, J = 11.2 Hz, 2 H, OCH C, H ),
2
eq
3
(
.46–3.49 (d, J = 11.2 Hz, 2 H, OCH C, H ), 1.61–1.66
2
ax
m, 2 H, CHCH CH ), 1.37 (m, 2 H, CH CH CH ), 1.26
2 2 2 2 3
[
m, 8 H, CH (CH ) CH ], 1.02 (s, 3 H, CCH ), 0.85–0.89
2 2 4 2 3
(
2
1
t, J = 6.8 Hz, 3 H, CH CH ); IR (KBr) ꢃ: 2920, 2853,
3
2
650, 1691, 1462, 1404, 1327, 1258, 1161, 1128, 1074,
−1
033, 1008, 947, 917, 877, 808, 720, 670, 590 cm ; Anal.
calcd for C H O : C 63.87, H 9.83, Found C 63.82,
13 24
4
H 9.89.
2
.1.3. General Procedure for the Synthesis of
5-methyl-2-alkyl-1,3-dioxane-5-carboxylic Acid
Sodium Salt (3a–3d)
ꢀ
1
2
a: a white solid; yield 53.6%; m.p. 135.4 C; H NMR
(
CDCl , 400 MHz) ꢁ: 4.48–4.50 (t, J = 5.2 Hz, 1 H,
3
OCHO), 4.42–4.45 (d, J = 11.6 Hz, 2 H, OCH C,
The method adopted for the synthesis of 5-methyl-
2-butyl-1,3-dioxane-5-carboxylic acid sodium salt (3a)
is described. 5.00 g (24.7 mmol) 5-methyl-2-butyl-1,3-
dioxane-5-carboxylic acid (2a) and 1.00 g (25 mmol)
2
H ), 3.45–3.48 (d, J = 11.6 Hz, 2 H, OCH C, H ),
eq
2
ax
1
.61–1.65 (m, 2 H, CHCH CH ꢂ, 1.29–1.38 [m, 4 H,
2 2
CH (CH ) CH ], 1.02 (s, 3 H, CCH ꢂ, 0.872–0.906
2
2 2
3
3
1086
J. Nanosci. Nanotechnol. 16, 1085–1089, 2016

Yuan et al.
Properties and Applications of Sodium (5-methyl-2-alkyl-1,3-dioxane-5-yl)-Carboxylate
sodium hydroxide were added into anhydrous methanol
30 mL) and refluxed for 8 h. After removal of the solvent,
to 0.0100 mol/L with water in 50 mL volumetric flasks,
then were kept in thermostated water bath at 25 C for
ꢀ
(
the crude product was purified by recrystallization from
10 min. The conductivity of the solution was measured
using a conductivity cell (type DDS-11A). Each solution
was measured three times and the final averaged values
were used to draw a ꢅ-C curve. The concentration cor-
responding to the breakpoint of the specific conductivity
isopropyl alcohol to afford a white block solid.
1
3
a: a white solid; yield 82.23%; H NMR (D O,
2
4
00 MHz) ꢁ: 4.63–4.65 (t, J = 4.4 Hz, 1 H, OCHO), 4.37
(
d, J = 11.2 Hz, 2 H, OCH C, H ), 3.50 (d, J = 11.2 Hz,
2
eq
1
2
4
H, OCH C, H ), 1.56 (m, 2 H, CH CH CH), 1.30 [m,
2 ax 2 2
versus concentration was taken as the CMC.
H, CH (CH ) CH ], 0.86 [m, 6 H, CH CH , CCH ]; IR
2
2 2
3
3
2
3
(
1
KBr) ꢃ: 2957, 2858, 1593, 1465, 1410, 1366, 1295, 1195,
145, 1106, 1000, 950, 910, 881, 840, 790, 669, 579 cm ;
2
.2.2. Emulsion Stability
−1
The emulsion stability of surfactants was measured as the
time of separation of the aqueous phase from the emulsion
layer. Emulsions were prepared by mixing 20 mL of aque-
ous surfactant solutions (2 wt%) and 20 mL of benzene at
Anal. calcd for C H O Na: C 53.53, H 7.58, Found C
5
1
0
17
4
3.47, H 7.65.
b: a white solid; yield 85.4%; H NMR (D O,
1
3
2
4
4
(
2
0
2
9
00 MHz) ꢁ: 4.63–4.65 (t, J = 4.8 Hz, 1 H, OCHO),
4
9
room temperature.
.36–4.39 (d, J = 10.8 Hz, 2 H, OCH C, H ), 3.49–3.51
2
eq
d, J = 11.2 Hz, 2 H, OCH C, H ), 1.53–1.57 (m,
2
ax
2
2
.2.3. Krafft Temperature
0 mL of surfactant solution (1 wt%), taken in 25 mL
H, CH CH CH), 1.27–1.33 [m, 6 H, CH(CH ) CH ],
2 2 2 3 3
.84–0.88 [m, 6 H, CH CH , CCH ]; IR (KBr) ꢃ: 2928,
3
2
3
graduated cylinders, was placed in a refrigerator, so that
solid surfactant-hydrate crystals appeared. The crylinder
was then taken out and the temperature was increased
until a clear solution was obtained. The temperature at
which the solution became clear was taken as the Krafft
855, 1587, 1464, 1409, 1365, 1296, 1147, 1107, 1013,
−1
07, 839, 725, 671, 578, 469 cm ; Anal. calcd for
C H O Na: C 55.39, H 7.97, Found C 55.43, H 7.91.
1
1
19
4
1
3
c: a white solid; yield 83.8%; H NMR (D O,
2
4
4
(
00 MHz) ꢁ: 4.62–4.65 (t, J = 4.8 Hz, 1 H, OCHO),
5
0
temperature (K ).
.36–4.39 (d, J = 11.2 Hz, 2 H, OCH C, H ), 3.48–3.51
T
2
eq
d, J = 11.2 Hz, 2 H, OCH C, H ), 1.55–1.56 (m, 2 H,
2
ax
CH CH CH), 1.26–1.28 [m, 8 H, CH(CH ) CH ], 0.86
[
2
9
2.2.4. Foaming Ability
2
2
2
4
3
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m, 6 H, CH CH , CCH ]; IR (KBr) ꢃ: 2958, 2926, 2855,
The foaming ability was obtained under vigorous shaking
IP: 91.204.15.80 On: Sat, 11 Jun 2016 05:56:00
780, 2662, 1593, 1463, 1411, 1367, 1295, 1143, 1021,
35, 908, 844, 794, 725, 667, 578, 509 cm ; Anal. calcd
3
2
3
of aqueous surfactant solutions (0.1 wt%) contained in a
Copyright: American Scientific Publishers
−1
50 mL glass-stopper graduated cylinder at room temper-
ature for 5 s, and the height of foam at the moment and
the height of foam 30 s later were recorded timely. The
ratio between them (the rest height of foam vs. the initial
for C H O Na: C 57.09, H 8.32, Found C 57.04, H 8.41.
1
2
21
4
1
3
d: a white solid; yield 82.8%; H NMR (D O,
2
4
4
(
2
0
2
1
00 MHz) ꢁ: 4.62–4.65 (t, J = 5.2 Hz, 1 H, OCHO),
.36–4.39 (d, J = 10ꢄ8 Hz, 2 H, OCH C, H ), 3.48–3.51
51
2
eq
height) was taken as the foaming ability of the surfactant.
d, J = 11.2 Hz, 2 H, OCH C, H ), 1.53–1.56 (m,
2
ax
H, CH CH CH), 1.26 [m, 10 H, CH –(CH ) –CH ],
2 2 2 2 5 3
2.2.5. Degradability
.83–0.86 [m, 6 H, CH CH , CCH ]; IR (KBr) ꢃ: 2954,
3
2
3
Surfactants 3a∼3d can be degraded into biodegradable raw
material moleculars, aldehydes and 2,2-dihydroxymethyl
propionic acid, through adding dilute HCl with heating.
The degradation process is given in Scheme 2.
924, 2855, 1598, 1464, 1410, 1366, 1296, 1142, 1104,
−1
077, 1022, 993, 941, 911, 838, 725, 669, 579 cm ; Anal.
calcd for C H O Na: C 58.59, H 8.64, Found C 58.55,
H 8.73.
1
3
23
4
2
2
.2. Methods
.2.1. Critical Micelle Concentration (CMC)
3. RESULTS AND DISCUSSION
3.1. CMC
The CMCs of surfactants were determined by conduc-
tivity measurements. A series of concentration of surfan-
tants 3a∼3d solution were prepared from 0.00005 mol/L
All the four studied surfactants showed sharp breaks in
the concentration isotherms (Fig. 1) which were used to
determine the CMC (Table I). It is clear that the values of
CH OH
2
H+
H+
H O
O
O
RCHO
+
C
COOH
COONa
COOH
H C
3
R
O
R
O
H O
2
2
CH OH
2
3
a~3d
2a~2d
1a~1d
a. R = C H ; b. R = C H ; c. R = C H ; d. R = C H
7 15
4
9
5
11
6
13
Scheme 2. Degradation process of surfactants 3a∼3d.
J. Nanosci. Nanotechnol. 16, 1085–1089, 2016
1087

Properties and Applications of Sodium (5-methyl-2-alkyl-1,3-dioxane-5-yl)-Carboxylate
Yuan et al.
Table II. Foam ability and emulsion stability of surfactants 3a∼3d.
0.15
0.14
0.13
0.12
0.11
0.10
0.09
Foam height
(mL) (0 s)
Foam height
(mL) (after 30 s)
Foam stability
(%)
Surfactants
3
a
6ꢄ27
6ꢄ45
6ꢄ68
6ꢄ86
0ꢄ41
0ꢄ44
0ꢄ51
0ꢄ62
6ꢄ49
6ꢄ82
7ꢄ63
9ꢄ04
3
c
3b
3c
3d
ꢀ
Table III. Degradability of surfactants 3a−3d in 2 N HCl at 50 C.
Surfactants
3a
3b
3c
3d
Surfactant quality (g)
Time (h)
Decomposition (%)
0ꢄ1
0ꢄ35
100
0ꢄ1
1ꢄ41
100
0ꢄ1
2ꢄ56
100
0ꢄ1
5ꢄ74
100
0.0005
0.0010
0.0015
0.0020
0.0025
0.0030
C (M)
Figure 1. Plot of specific conductance of aqueous 3c surfactant solu-
tions as a function of the concentration (C).
3
.5. Degradability
Surfactants 3a∼3d are a type of single carboxylic acid
sodium salt with 1,3-dioxane ring, and are water-soluble
and stable under neutral and alkaline conditions, and turn
into segregative solid precipitation under acid condition so
that the system can eliminate the undesirable bubbles and
emulsifying phenomenon. The precipitation can be pro-
cessed with alkali to generate the original surfactants to
reuse and can also be easily degraded into biodegradable
raw material molecules through adding dilute acid with
CMCs of surfactants 3a∼3d, given in Table I, are all less
than 2.0 ×10− mol/L.
3
3
.2. Emulsion Stability
The stability of benzene-in-water emulsion in the presence
of these four surfactants was investigated. The emulsions
were stabilized by adding an emulsifier or surfactant. Here,
in the present case, the stability of the emulsion increases
with the increase in length of the hydrophobic tail of the
surfactant. In the presence of 3a, it takes 32 min for sep-
aration of the aqueous layer from the emulsion whereas
for 3b, 3c and 3d the times taken were 60 min, 174 min
and 384 min, respectively. Thus, the emulsion stability
increases with the increase in the hydrophobic tail length.
ꢀ
heating. The degradability of 3a–3d in 2 N HCl at 50 C
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was examined and the results are shown in Table III. From
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Table III, it is clear that the degradation time of 3a–3d
Copyright: American Scientific Publishers
increases as the alkyl chain length increases under the
same conditions.
4
. CONCLUSIONS
3
.3. Krafft Temperature
The sodium (5-methyl-2-alkyl-1,3-dioxane-5-yl)-
carboxylate containing 1,3-dioxane ring is a new type
of surfactants synthesized using nanosolid superacid
SO /Fe O as a catalyst. CMC, Krafft point, emulsion
stability, foam ability and degradability of surfactants were
determined and the results showed that the CMC values
The Krafft Temperature (K ) is the minimum temperature
at which surfactants from micelles. Below K , micelles do
not form and surfactants remain in crystalline form, even
in aqueous solution. The values of the Krafft Temperature
T
T
2−
4
2
3
(
K ) for surfactants 3a∼3d are given in Table I, and all of
T
ꢀ
them were taken as less than 0 C.
−3
were less than 2.0×10 mol/L, emulsion formation, foam
stability and the range of application temperature, com-
pared with traditional surfactants, the new surfactants give
better results and show better properties as the emulsifier
in emulsion polymerization. In addition, the surfactants
are stable under neutral and alkaline conditions, and can
form solid in acid condition. The solid will generate
to the original surfactants for reuse with alkali. Based
on the above conclusions, sodium (5-methyl-2-alkyl-1,3-
dioxane-5-yl) carboxylate is likely to be a new type of
3
.4. Foaming Ability
The foam ability data for the four surfactants are list in
Table II. It is clear that the initial height of foam produced
by surfactants increases with the increase in the tail length.
Due to the high hydrophobicity, 3d produces a greater
height and more stable foams than the others.
Table I. CMC, emulsifiability and krafft temperature of surfactants
‘
environmentally friendly’ surfactant.
3a∼3d.
Surfactant
3a
3b
3c
3d
Acknowledgments: This work was financially sup-
ported by the Opening Project of Key Laboratory
of Comprehensive Utilization of Advantage Plants
Resources in Hunan South (XNZW14C01), the Scientific
3
1
0 CMC (mol/L)
0.8
32
1.6
60
1.6
1.6
Emulsifiability (min)
Krafft temperature
174
384
ꢀ
ꢀ
ꢀ
ꢀ
< 0 C
< 0 C
< 0 C
< 0 C
1088
J. Nanosci. Nanotechnol. 16, 1085–1089, 2016

Yuan et al.
Properties and Applications of Sodium (5-methyl-2-alkyl-1,3-dioxane-5-yl)-Carboxylate
Research Fund of Hunan Provincial Education Department
14A058), the Construct Program of the Key Discipline in
Hunan Province (2011–76).
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Received: 31 August 2014. Accepted: 3 October 2014.
J. Nanosci. Nanotechnol. 16, 1085–1089, 2016
1089