Properties and applications of sodium 2-alkyl-5-(ethoxycarbonyl)-1,3-dioxane-5-carboxylate synthesized with nano-sulfonated carbon

Article abstract of DOI:10.1166/jnn.2017.12859

A series of novel sodium 2-alkyl-5-(ethoxycarbonyl)-1,3-dioxane-5-carboxylate surfactants were synthesized in high yield using nanosolid superacid sulfonated carbon as a catalyst and characterized by ¹H NMR, IR and elemental analysis. Critical micelle concentration (CMC) of the surfactants was determined and the results showed that the CMC values were less than 1.0 × 10^-3 mol/L. Other relevant surface properties were also evaluated, such as emulsion stability, foam ability and degradability. In relation to emulsion formation, foam stability and the range of application of temperature, the new surfactants showed better properties than traditional surfactants when used as an emulsifier in emulsion polymerization. Moreover, the surfactants were stable under alkaline and neutral conditions, and degraded into raw materials under acid condition. Convenient synthesis process with high yield and superior properties promisingly make the title compounds to be a type of 'environmentally friendly' surfactants.

Full text of DOI:10.1166/jnn.2017.12859

Article
Journal of
Nanoscience and Nanotechnology
Vol. 17, 2201–2205, 2017
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Properties and Applications of Sodium
2-Alkyl-5-(Ethoxycarbonyl)-1,3-Dioxane-5-Carboxylate
Synthesized with Nano-Sulfonated Carbon
Lin Yuan1ꢀ2ꢀ∗, Zhong Yan Li2, Min Zhang2, Xian You Yuan2, and Xiao Qing Zhu1
1State Key Laboratory of Elemento-Organic Chemistry, Department of Chemistry, Nankai University, Tianjin 300071, P. R. China
2Key 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 2-alkyl-5-(ethoxycarbonyl)-1,3-dioxane-5-carboxylate surfactants were syn-
thesized in high yield using nanosolid superacid sulfonated carbon as a catalyst and characterized
1
by H NMR, IR and elemental analysis. Critical micelle concentration (CMC) of the surfactants was
determined and the results showed that the CMC values were less than 1ꢀ0 × 10−3 mol/L. Other
relevant surface properties were also evaluated, such as emulsion stability, foam ability and degrad-
ability. In relation to emulsion formation, foam stability and the range of application of temperature,
the new surfactants showed better properties than traditional surfactants when used as an emulsifier
in emulsion polymerization. Moreover, the surfactants were stable under alkaline and neutral condi-
Delivered by Ingenta to: Sibley Library, Eastman School of Music
tions, and degraded into raw materials under acid condition. Convenient synthesis process with high
IP: 93.179.90.37 On: Wed, 21 Jun 2017 06:57:37
yield and superior properties promisingly make the title compounds to be a type of ‘environmentally
Copyright: American Scientific Publishers
friendly’ surfactants.
Keywords: Nanosolid Superacid, Synthesis, Acetal, 1,3-Dioxane, Surfactant.
1. INTRODUCTION
acid condition, and the products could be separated easily
from two phases.9–11 In recent years, nanomaterials such
as nanosolid superacids have attracted so much attention
by their better chemical properties.12–20 Sulfonated car-
bon was usually used as a kind of nanosolid superacid
in organic catalytic synthesis and worked very well.21–28
In this paper, a new type of segregative and degradable
surfactants containing 1,3-dioxane were synthesized by
diethyl 2,2-bis(hydroxymethyl)malonate with long-chain
fatty aldehyde, using nanosolid superacid sulfonated car-
bon as a catalyst (Scheme 1). It was showed that these new
surfactants were stable under alkaline and neutral condi-
tions, and would degrade into the raw materials in acid
environment. From the above, these surfactants are promis-
ing to be a novel type of competitive and eco-friendly
ones.29–33
Toothpaste, shampoo, detergent and washing powder like
old friends to meet every day in our lives, and they have
a common point, that is all of their active constituents
are surfactants. Classical surfactants consist of two obvi-
ous parts, one polar and the other nonpolar, incompatible
with each other. Because of this amphiphilicity, surfac-
tant molecules tend to self-aggregate into micelles, which
form the basis of many biochemical processes. Surfac-
tants were widely used in different industrial areas, such
as cleaning, paint, emulision, catalysis, microreactor, phar-
maceuticals and so on.1–3 Long-chain acetal, which could
be synthesized by fatty aldehyde and polyhydric alcohols
using acid as a catalyst, is an important type of materials
to make segregative and degradable surfactants.4ꢀ5 Com-
pared with traditional surfactants, this type of acetal com-
pounds possess unusual physicochemical properties and
can be used in the emulsion polymerization and emul-
sion of organic reactions with higher efficiency.6–8 After
the reaction, microemulsion could be decomposed under
2. EXPERIMENTAL SECTION
2.1. Instrumentation and Materials
2.1.1. Instruments
The nanosolid catalyst sulfonated carbon was prepared
∗Author to whom correspondence should be addressed.
according to the literature.28 SEM image of the sulfonated
J. Nanosci. Nanotechnol. 2017, Vol. 17, No. 3
1533-4880/2017/17/2201/005
doi:10.1166/jnn.2017.12859
2201

Properties and Applications of Sodium 2-Alkyl-5-(Ethoxycarbonyl)-1,3-Dioxane-5-Carboxylate
Yuan et al.
O
O
O
O
OCH2CH3
OCH2CH3
HO
HO
O
O
O
O
OCH2CH3
OCH2CH3
OCH2CH3
ONa
sulfonated carbon
DMF, reflux
NaOH
+
RCHO
R
R
C2H5OH
1a R = n-C4H9
1b R = n-C6H13
1c R = n-C7H15
1d R = n-C9H19
O
O
2a~2d
3a~3d
Scheme 1. Synthesis of surfactants 3a∼3d.
carbon is shown in Figure 1. Melting point data were
recorded on a XRC-1 microscopic melting point meter
with the thermometer without correction. Element analysis
was recorded on PE2400 instrument. The IR spectra were
recorded in the 4000–400 cm−1 region using KBr pellets
and a Niconet AVATAR-360 spectrometer. 1H NMR spec-
tra were recorded in a DMSO solution with a VARAN
UNTTY INOV-400 spectrometer. 2,2-Bis(hydroxymethyl)
malonate (98%, Aladdin) and all of the aldehyde (Aladdin)
were purified by distillation before use. Other materials
and solvents were commercially available and were used
without further purification.
(q, 2H, CH2CH2CH2CH3ꢂ; 4.14 (q, 4H, O-CH2–CH3);
4.19–4.21 (d, J = 11.2 Hz, 2H, Hax); 4.379 (t, 1H, –CH);
4..452–4.593 (d, J = 11.2 Hz, 2H, Heq); IR (KBr) ꢃ:
2961.3, 2873.7, 1725.6, 1465.7, 1446.2, 1368.1, 1242.9,
1185.1, 1151.8, 1109.1, 857.1, 756.1 cm−1; Anal. Calcd
for C14H24O6: C 58.33%, H 8.33%, Found C 58.28%,
H 8.37%.
2b: A colorless oil; yield 75.6%, b.p. 182 ꢀC
1
(0.1 Mpa); H NMR (DMSO, 400 MHz) ꢁ (ppm): 0.89
(t, 3H, C5H10CH3ꢂ; 1.152 (t, 6H, O–CH2CH3ꢂ; 1.21–1.29
(m, 8H, CH2C4H8CH3ꢂ; 1.456 (q, 2H, CH2C4H8CH3ꢂ;
3.925–3.953 (d, J = 11.2 Hz, 2H, Hax); 4.12–4.23
(q, 4H, O-CH2–CH3ꢂ; 4.481–4.509 (d, J = 11.2 Hz, 2H,
Heq); 4.560–4.568 (t, 1H, –CH); IR (KBr) ꢃ: 2929.4,
2858.4, 1731.1, 1465.0, 1381.5, 1367.1, 1250.8, 1218.4,
1149.3, 1110.9, 1043.7, 937.6, 861.4 cm−1; Anal. Calcd
for C16H28O6: C 60.76%, H 8.86%, Found C 60.66%,
H 8.78%.
2.1.2. General Procedure for the Synthesis of Diethyl
2-Alkyl-1,3-Dioxane-5,5-Dicarboxylate (2a–2d)
A solution of diethyl 2,2-bis(hydroxymethyl) malonate
(12 mmol),
1 (10 mmol) and sulfonated carbon
(1.0 g) were heated to reflux in a mixture of N ,N -
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dimethylformamide (10 mL) and cyclohexane (6 mL)
2c: A colorless oil; yield 71.26%, b.p. 198 ꢀC
IP: 93.179.90.37 On: Wed, 21 Jun 2017 06:57:37
1
under stirring for 3 h. After cooling to room tempera-
(0.1 Mpa); H NMR (DMSO, 400 MHz) ꢁ (ppm): 0.87
Copyright: American Scientific Publishers
ture, the solution was filtered and the solvent was removed
(t, 3H, C6H12CH3ꢂ; 1.17 (t, 6H, O–CH2CH3ꢂ; 1.19–1.22
(m, 10H, CH2C5H10CH3ꢂ; 1.45 (q, 2H, CH2C5H10CH3ꢂ;
3.93–3.95 (d, J = 11.2 Hz, 2H, Hax); 4.12–4.27 (m, 4H,
O–CH2–CH3); 4.49–4.52 (d, J = 11.2 Hz, 2H, Heq); 4.57
(s, 1H, –CH); IR (KBr) ꢃ: 2927.3, 2856.7, 1737.1, 1465.1,
1367.3, 1252.1, 1222.9, 1149.6, 1112.3, 1095.0, 1041.8,
940.8, 863.4 cm−1; Anal. Calcd for C17H30O6: C 61.82%,
H 9.09%, Found C 61.75%, H 9.12%.
in vacuo, the residue was dissolved in EtOAc (15 mL),
washed with saturated brine (10 mL × 2) and water
(10 mL × 2), dried over anhydrous Na2SO4. The solvent
was filtered and concentrated to give 2a–2d as color-
less oil.
2a: A colorless oil; yield 78.1%; b.p. 124 ꢀC (0.1 Mpa);
1H NMR (DMSO, 400 MHz) ꢁ (ppm): 0.85 (t, 3H,
CH2CH2CH2CH3ꢂ; 1.21 (t, 6H, O–CH2–CH3,); 1.28–1.29
(m, 4H, CH2CH2CH2CH3, CH2CH2CH2CH3ꢂ; 1.48
2d: A colorless oil; yield 68.09%, b.p. 222 ꢀC
1
(0.1 Mpa); H NMR (DMSO, 400 MHz) ꢁ (ppm): 0.86
(t, 3H, C7H14CH3ꢂ; 1.16 (t, 6H, O-CH2CH3ꢂ; 1.21–1.26
(m, 12H, CH2C6H12CH3ꢂ; 1.44 (q, 2H, CH2C6H12CH3ꢂ;
3.93–3.95 (d, J = 11.2 Hz, 2H, Hax); 4.12–4.23 (s, 4H,
O–CH2–CH3ꢂ; 4.48–4.51 (d, J = 11.2 Hz, 2H, Heq);
4.57 (s, 1H, –CH); IR (KBr) ꢃ: 2929.0, 28558.2, 1737.3,
1465.1, 1367.2, 1251.4, 1218.5, 1149.5, 1111.0, 1043.6,
937.5, 861.1 cm−1; Anal. Calcd for C19H34O6: C 63.69%,
H 9.50%, Found C 63.71%, H 9.47%.
2.1.3. General Procedure for the Synthesis of Sodium
2-Alkyl-5-(ethoxycarbonyl)-1,3-Dioxane-5-
Carboxylate (3a–3d)
A solution of 2 (50 mmol) and NaOH (49 mmol) were
heated to reflux in ethanol (12 mL) with stirring for
12 h. After cooling to room temperature, the reaction mix-
ture was filtered and the crude product was purified by
Figure 1. SEM image of sulfonated carbon prepared as a catalyst.
2202
J. Nanosci. Nanotechnol. 17, 2201–2205, 2017

Yuan et al.
Properties and Applications of Sodium 2-Alkyl-5-(Ethoxycarbonyl)-1,3-Dioxane-5-Carboxylate
O
O
O
O
O
O
O
O
H+
OCH2CH3
ONa
OCH2CH3
OH
H+
HO
HO
OCH2CH3
OH
R
R
RCHO
+
H2O
H2O
O
O
3a~3d
2a~2d
1a~1d
Scheme 2. Degradation process of surfactants 3a∼3d.
recrystallization from isopropyl alcohol to afford a white
powdery solid.
to 0.0100 mol/L with water in 50 mL volumetric ꢀflasks,
then were kept in thermostated water bath at 25 C for
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 ꢄ-C curve. The concentration cor-
responding to the breakpoint of the specific conductivity
versus concentration was taken as the CMC.
1
3a: A white powdery solid, yield 59.42%; H NMR
(DMSO, 400 MHz) ꢁ (ppm): 0.85 (t, 3H, C3H6CH3ꢂ;
1.07–1.18 (m, 10H, CH2C4H8CH3ꢂ; 1.21 (t, 3H,
O–CH2CH3); 4.07–4.09 (q, 2H, O–CH2-CH3ꢂ; 4.10–4.12
(d, J = 11.2 Hz, 2H, Heq); 4.21 (t, 1H, –CH); 4.39–4.40
(d, J = 11.2 Hz, 2H, Hax); IR (KBr) ꢃ: 2949.9, 1733.5,
1574.6, 1420.5, 1236.1, 1096.7, 1030.9 cm−1; Anal. Calcd
for C12H19O6Na: C 51.06%, H 6.74%, Found C 51.03%,
H 6.79%.
2.2.2. Emulsion Stability
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
room temperature.
1
3b: A white powdery solid, yield 60.96 %; H NMR
(DMSO, 400 MHz) ꢁ (ppm): 0.86 (t, 3H, C5H10CH3ꢂ; 1.21
(t, 3H, O–CH2CH3ꢂ; 1.24–1.29 (m, 10H, CH2C4H8CH3ꢂ;
1.42–1.43 (q, 2H, CH2C4H8CH3ꢂ; 3.84–3.96 (q, 2H,
O–CH2–CH3); 4.14–4.15 (d, J = 10.8 Hz, 2H, Hax);
4.33–4.35 (t, 1H, –CH); 4.46–4.58 (d, J = 10.8 Hz, 2H,
Heq); IR (KBr) ꢃ: 2939.3, 2867.6, 1736.1, 1613.6, 1459.9,
1249.6, 1156.5, 1043.3, 862.9, 588.0 cm−1; Anal. Calcd
2.2.3. Foaming Ability
The foaming ability was obtained under vigorous shaking
of aqueous surfactant solutions (0.1 wt%) contained in a
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for C14H23O6Na: C 54.19%, H 7.42%, Found 54.12%,
50 mL glass-stopper graduated cylinder at room temper-
IP: 93.179.90.37 On: Wed, 21 Jun 2017 06:57:37
H 7.47%.
ature for 5 s, and the height of foam at the moment and
Copyright: American Scientific Publishers
1
3c: A white powdery solid, yield 60.34%; H NMR
(DMSO, 400 MHz) ꢁ (ppm): 0.87 (t, 3H, C6H12CH3ꢂ; 1.17
(t, 3H, O–CH2CH3ꢂ; 1.25–1.29 (m, 10H, CH2C5H10CH3ꢂ;
1.44–1.45 (q, 2H, CH2C5H10CH3ꢂ; 3.84–3.97 (q, 2H,
O–CH2–CH3ꢂ; 4.14–4.23 (d, J = 11.2 Hz, 2H, Hax);
4.33–4.36 (t, 1H, –CH); 4.47–4.59 (d, J = 11.2 Hz,
2H, Heq); IR (KBr) ꢃ: 2934.4, 2864.6, 1737.4, 1612.8,
1458.2, 1250.0, 1155.4, 1046.4, 867.9 cm−1; Anal. Calcd
for C15H25O6Na: C 55.56%, H 7.72%, Found C 55.50%,
H 7.69%.
the height of foam 30 s later were recorded timely. The
ratio between them (the rest height of foam vs. the initial
height) was taken as the foaming ability of the surfactant.
2.2.4. Degradability
Surfactants 3a∼3d can be degraded into biodegradable
raw material molecules, aldehydes and 3-ethoxy-2,2-
bis(hydroxymethyl)-3-oxopropanoic acid, through adding
dilute HCl with heating. The degradation process is given
in Scheme 2.
1
3d: A white powdery solid, yield 52.63%; H NMR
350
(DMSO, 400 MHz) ꢁ (ppm): 0.88 (t, 3H, C7H14CH3ꢂ; 1.18
(t, 3H, O–CH2CH3ꢂ; 1.26–1.29 (m, 12H, CH2C6H12CH3ꢂ;
1.47 (q, 2H, CH2C6H12CH3ꢂ; 3.73–3.96 (q, 2H, O–CH2–
CH3ꢂ; 4.18–4.21 (d, J = 11.2 Hz, 2H, Hax); 4.34–4.35
(t, 1H, –CH); 4.50–4.52 (d, J = 11.2 Hz, 2H, Heq) IR
(KBr) ꢃ: 2930.6, 2861.3, 1736.8, 1616.6, 1461.3, 1337.5,
1250.0, 1155.0, 1049.3, 868.6, 785.8, 579.6 cm−1; Anal.
Calcd for C17H29O6Na: C 57.95%, H 8.24%, Found C
57.91%, H 8.25%.
3a
300
250
200
150
100
50
3b
3c
3d
2.2. Methods
0.0 0.2 0.4 0.6 0.8 1.0 1.2 1.4 1.6 1.8
2.2.1. Critical Micelle Concentration (CMC)
The CMCs of surfactants were determined by conduc-
tivity measurements. A series of concentration of surfac-
tants 3a∼3d solution were prepared from 0.00005 mol/L
C × 103 (M)
Figure 2. Plot of specific conductance of aqueous 3a∼3d surfactant
solutions as a function of the concentration (C) at 298 K.
J. Nanosci. Nanotechnol. 17, 2201–2205, 2017
2203

Properties and Applications of Sodium 2-Alkyl-5-(Ethoxycarbonyl)-1,3-Dioxane-5-Carboxylate
Table I. Emulsifiability and foam ability of surfactants 3a∼3d.
Yuan et al.
4. CONCLUSIONS
The sodium 2-alkyl-5-(ethoxycarbonyl)-1,3-dioxane-5-
carboxylate containing 1,3-dioxane ring is a new type
of surfactant synthesized using nanosolid superacid sul-
fonated carbon as a catalyst. CMC, emulsion stability,
foam ability and degradability of surfactants were deter-
mined and the results showed that the new surfactants give
better results and show better properties than traditional
surfactants in relation to emulsion formation, foam stabil-
ity and the range of application temperature as well as the
CMC values less than 1.0 × 10−3 mol/L. In addition, the
tests showed that these new surfactants were stable under
alkaline and neutral conditions, and would degrade into the
raw materials in acid environment. From the above, these
surfactants are promising to be a novel type of competitive
and eco-friendly ones. Moreover, with rapid advances in
nanotechnology,36–60 we believe more efficient nanocataly-
sis system will be developed and more eco-friendly surfac-
tants with more satisfactory properties will be developed.
Surfactant
3a
3b
3c
3d
CMC×103 (mol/L)
Emulsifiability (min)
Foam stability (%)
0ꢅ8
4ꢅ2
38ꢅ57
0ꢅ7
17ꢅ5
47ꢅ05
0ꢅ9
40ꢅ0
72ꢅ48
0ꢅ8
57ꢅ7
90ꢅ38
3. RESULTS AND DISCUSSION
3.1. CMC
All the four studied surfactants showed sharp breaks in
the concentration isotherms (Fig. 2) which were used to
determine the CMC (Table I). It is clear that the values of
CMCs of surfactants 3a∼3d, given in Table I, are all less
than 9.0 ×10−4 mol/L.
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 (Table I). In the presence of 3a, it takes 4.2 min
for separation of the aqueous layer from the emulsion
whereas for 3b, 3c and 3d the times taken were 17.5 min,
40.0 min and 57.7 min, respectively. Thus, the emulsion
stability increases with the increase in the hydrophobic tail
Acknowledgments: This work was financially sup-
ported by the Science and Technology Planning
Project of Hunan Province (2015GK3037), the Scientific
Research Fund of Hunan Provincial Education Department
(14A058) and the construct program of the key discipline
in Hunan Province (2016).
length.
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Copyright: American Scientific Publishers
References and Notes
3.3. Foaming Ability
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3.4. 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
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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
heating. The degradability of 3a–3d in 0.1 N HCl at 25 ꢀC
was examined and the results are shown in Table II. From
Table II, it is clear that 3a–3d are all degraded within
2 hours.
Table II. Degradation of surfactants 3a–3d in 0.1 N HCl at 25 ꢀC.
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Time (h)
Decomposition (%)
0.5
2
100
0.5
2
100
0.5
2
100
0.5
2
100
2204
J. Nanosci. Nanotechnol. 17, 2201–2205, 2017

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Properties and Applications of Sodium 2-Alkyl-5-(Ethoxycarbonyl)-1,3-Dioxane-5-Carboxylate
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Received: 23 October 2015. Accepted: 1 March 2016.
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