Solubilities of 1,3,2-dioxaphosphorinane-2-methanol-α,5,5-trimethyl-α-phenyl-2-oxide in selected solvents between 278.15 k and 343.15 k

Article abstract of DOI:10.1021/je500806u

The mole fraction solubilities of 1,3,2-dioxaphosphorinane-2-methanol-α,5,5-trimethyl-α-phenyl-2-oxide in different organic solvents including acetonitrile, acetone, ethyl acetate, 1,2-dichloroethane, methanol, ethanol, and chloroform were measured at a d

Full text of DOI:10.1021/je500806u

Article
pubs.acs.org/jced
Solubilities of 1,3,2-Dioxaphosphorinane-2-methanol-α,5,5-
trimethyl-α-phenyl-2-oxide in Selected Solvents between 278.15 K
and 343.15 K
Yong Yuan, Rui-lan Fan,* Lai Guo, Cong-yan Chen, and Qian-qiong Zhao
Inner Mongolia Key Laboratory of Fine Organic Synthesis, College of Chemistry and Chemical Engineering, Inner Mongolia
University, Hohhot 010021, People’s Republic of China
ABSTRACT: The mole fraction solubilities of 1,3,2-dioxaphosphorinane-2-
methanol-α,5,5-trimethyl-α-phenyl-2-oxide in different organic solvents includ-
ing acetonitrile, acetone, ethyl acetate, 1,2-dichloroethane, methanol, ethanol,
and chloroform were measured at a designated temperature range of (278.15 to
3
43.15) K and at atmospheric pressure by the gravimetrical method. The
compound’s structure and thermal stability were characterized by infrared
1
31
spectroscopy, nuclear magnetic resonance ( H NMR and P NMR), mass
spectroscopy, elemental analysis, and thermogravimetric analysis. The mole
fraction solubilities of 1,3,2-dioxaphosphorinane-2-methanol-α,5,5-trimethyl-α-
phenyl-2-oxide in the above-mentioned organic solvents were correlated as the
Apelblat equation, and the calculated values with equations showed good
consistency with the experimental values. The root-mean-square deviation was
less than 0.010 % and the average relative error was less than 0.11 % in all the
experiments.
1
. INTRODUCTION
solubility of DMPO in various kinds of organic solvents at
different temperatures. However, a systematic study of the
solubility of this phosphorus-containing flame retardant in
different solvent systems has not been reported.
In this work, the solubilities of DMPO in different of organic
solvents, including acetonitrile, acetone, ethyl acetate, 1,2-
dichloroethane, methanol, ethanol, and chloroform were
measured at a designated temperature range of (278.15 to
Environmental protection has become very important and
because of this the development of a low carbon, high
efficiency, and multifunctional flame retardant has become the
future trend of the flame retardant industry. An organic
phosphorus flame retardant has its own characteristics, which
has attracted much attention in the field of flame retardant
science and has a far-ranging development potential. Cyclic
phosphorus compounds are particularly thermally stable and
3
43.15) K at atmospheric pressure by the gravimetrical method.
1
,2
The mole fraction solubilities (x) in the mentioned solvents
were correlated as the Apelblat equation, and the calculated
values with this equation showed good consistency with
experimental values. The aim of this study is to provide basic
information for the separation, purification, and application of
DMPO.
useful as flame retardants for polymeric materials.
At present, an efficient phosphorus-containing compound,
,3,2-dioxaphosphorinane-2-methanol-α,5,5-trimethyl-α-phe-
1
nyl-2-oxide (DMPO; chemical formula, C H O P; molecular
1
3
19
4
weight, 270; its formula is shown in Figure 1) (CASRN
2
. EXPERIMENTAL SECTION
.1. Chemicals. All of the solvents, acetonitrile, acetone,
2
ethyl acetate, 1,2-dichloroethane, methanol, ethanol, and
chloroform were obtained from Tianjinbeilian Chemical
Reagent Co., Ltd. They were all analytical-grade research
reagents, and their purities were higher than 0.99. The mass
fraction purities for the organic solvents used are listed in Table
Figure 1. Chemical structure of 1,3,2-dioxaphosphorinane-2-meth-
anol-α,5,5-trimethyl-α-phenyl-2-oxide.
1
82057-08-5), was synthesized by our laboratory. Complete
and accurate solubility data can provide important foundation
for solvent selection in the synthesis and purification of
compounds. Thus, we can find an inexpensive, effective, and
low toxic solvent for compound synthesis and recrystallization
and then further guide the compound for industrial production.
A higher purity of DMPO is required in the application of the
polyurethane flame retardant. For improving and optimizing
the crystallization process, it is imperative for us to know the
1
.
2
.2. Apparatus. The apparatus for the solubility measure3-
ment is identical to that described in detail in the literature.
Received: September 17, 2014
Accepted: January 8, 2015
©
XXXX American Chemical Society
A
DOI: 10.1021/je500806u
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Journal of Chemical & Engineering Data
Article
Table 1. Chemical Compounds Used in the Study
necked, round-bottomed flask, provided with a magnetic stirrer,
a reflux condenser, and thermometer, 13 g of neopentyl glycol
and 50 mL of 1,2-dichloroethane are added. Next, 12 mL of
phosphorus trichloride under an ice bath is added. The
temperature is raised to 313.15 K with 2 h of mixing. The
mixture is then cooled to room temperatur and 15 mL of
acetophenone is added, followed by the slow addition of 5 mL
of anhydrous formic acid. This mixture is then heated to 323.15
K for 5 h, and allowed to cool to ambient temperature. The
crude product was then filtrated and washed with ether. The
residue was recrystallized by ethanol, and finally white powder
was gained. IR (KBr): 3222 (O−H), 2969 to 2907 (C−H),
3063 (Ar−H), 1251 (PO), 1072 (P−O−C), 1605, 1496,
696, 747 cm− (ph). MS (ESI) m/z: 270.84. H NMR (CDCl )
3
purity (mass
analysis
method
chemicals
acetone
source
fraction)
b
Tianjinbeilian
Tianjinbeilian
Tianjinbeilian
0.995
0.998
0.997
0.990
0.997
0.995
0.995
0.998
acetonitrile
chloroform
1
,2-dichloroethane Tianjinbeilian
ethanol
Tianjinbeilian
Tianjinbeilian
Tianjinbeilian
ethyl acetate
methanol
a
c
DMPO
synthesized in the
lab
HPLC
a
DMPO = 1,3,2-dioxaphosphorinane-2-methanol-α,5,5-trimethyl-α-
1
1
b
phenyl-2-oxide, CASRN 182057-08-5, white solid state. Tianjinbei-
lian Chemical Reagent Co., Ltd. High-performance liquid chromatog-
c
ppm: δ = 0.821,1.083 (6H,2CH ), δ = 1.897,1.928 (3H,CH ), δ
3
3
raphy.
= 2.901 (1H,OH), δ = 3.847 to 4.070 (4H,2CH ), δ = 7.264 to
2
7
.651 (5H,Ph). 31P NMR (CDCl ) ppm: δ = 17.15 ppm.
3
Figure 2 shows the schematic diagram of the experimental
setup. A jacketed equilibrium cell was used for the solubility
Elemental analysis found (calcd): C = 57.75 % (57.78 %), H =
7.07 % (7.04 %). On the basis of the above analysis, the purity
of DMPO used in this work was higher than 0.99.
2
.4. Thermogravimetric Analysis. An NETZSCH STA
4
09 PC thermogravimetric analyzer was employed for
thermogravimetric analysis at a heating rate of 10 K·min
−1
under nitrogen from 298.15 K to 853.15 K. The thermogravi-
metric curve of DMPO is shown in Figure 3. The initial
Figure 2. Schematic diagram of solubility apparatus: 1, thermometer;
2
, sample export; 3, rubber plug; 4, equilibrium cell; 5, magneton 6,
magnetic stirrer apparatus; 7, water cycling bath; 8, rubber pipe.
measurement with a working volume of 120 mL and a magnetic
stirrer. A circulating water bath was applied with a thermostat
(
type 50 L, made from Changzhouzhiboriu Laboratory
Instrument Work Co.,Ltd.), which is capable of maintaining
the temperature within ± 0.05 K. An analytical balance (type
BSA124S Beijing Satorius Scientific Instruments Works Co.)
with an uncertainty of ± 0.1 mg was used during the mass
measurements.
Thermogravimetric analysis (TGA) was carried out with an
NETZSCH STA 409 PC thermogravimetric analyzer at a
heating rate of 10 K· min under nitrogen from 298.15 K to
−1
Figure 3. Thermogravimetric analysis (TGA) curves of DMPO.
8
53.15 K. The elemental analysis was performed on an
decomposition temperature of DMPO was around 469.15 K.
The weight loss was 90 % at the temperature ranging from
Elementar Vario EL element analyzer. The melting point was
determined by X-4 Micro Melting Point Apparatus (Beijing
Fukai Instrument Co., Ltd.). IR spectra (Fourier transform
infrared (FTIR)) was obtained with a Thermo 6700FT-IR
using KBr pellets. Mass spectra were recorded by a LCQ
Advantage MAX. H NMR and P NMR spectra were
recorded on a Bruker AVANCE III 500.
4
70.15 K to 485.15 K, and the char residue yield at 490.15 K
was 0.85 %. The compound of DMPO is almost decomposed
completely, which is very different from the structurally similar
compound 1,3,2-dioxaphosphorinane-2-methaol-α,α,5,5-tetra-
1
31
4
methyl-2-oxide (DMTO). The benzene ring structure did
not increase the amount of residual carbon compound; on the
contrary, because of the high activity of hydroxyl groups in
benzyl alcohol, the structure of the compound more easily
decomposes. Therefore, it generates an olefin compound by
dehydration. The above conclusions need to be further
investigated.
2
.3. Synthesis and Characterization of DMPO. DMPO
was prepared by our laboratory. The yield was 71.3 %, and the
melting point was 431.15 K to 434.15 K. DMPO was prepared
by the reaction (Scheme 1) as follows: In a 250 mL three-
Scheme 1
2
.5. Solubility Measurement. The mole fraction
solubilities of DMPO in different organic solvents including
acetonitrile, acetone, ethyl acetate, 1,2-dichloroethane, meth-
anol, ethanol, and chloroform were measured at a designated
temperature at atmospheric pressure by a gravimetrical method.
B
DOI: 10.1021/je500806u
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Article
exp
Table 2. Experimental Mole Fraction Solubility (x ) of DMPO in Different Solvents at Varied Temperatures T and Pressure p
a
=
0.1 MPa
a
b
c
a
b
c
solvent
T/K
297.95
x·1000
ε
solvent
methanol
T/K
x·1000
ε
ethyl acetate
chloroform
acetonitrile
0.54
0.92
1.31
1.66
2.21
2.40
2.83
3.07
3.36
3.60
4.80
5.47
6.51
7.68
8.66
9.44
11.14
12.76
15.40
18.78
1.44
1.69
1.98
2.21
2.68
3.42
3.92
4.60
5.62
6.54
8.66
1.06
1.32
1.80
2.30
3.10
3.63
4.69
5.47
5.93
−0.0540
0.0351
323.15
283.35
288.15
293.25
298.31
303.15
307.95
313.05
317.95
323.15
278.35
283.25
288.45
293.35
298.25
303.15
308.25
313.15
318.05
322.95
328.15
333.25
338.15
278.45
283.25
288.15
293.25
298.35
303.05
307.95
313.05
318.15
323.05
327.95
333.15
338.05
343.15
6.16
11.21
13.16
14.61
16.76
19.57
22.27
25.88
28.51
32.13
1.07
−0.0637
−0.0007
0.0205
3
3
3
3
3
3
3
3
3
03.35
08.45
13.15
18.05
23.05
28.35
33.25
38.15
42.95
0.0375
0.0037
−0.0191
−0.0214
0.0033
0.0553
−0.0501
−0.0328
−0.0446
−0.0060
0.0477
0.0059
0.0242
−0.0024
−0.0115
0.0271
278.25
−0.0179
−0.0187
0.0247
1,2-dichloroethane
2
2
2
2
3
3
3
3
3
83.35
88.15
93.05
98.45
03.35
08.15
13.05
17.95
23.15
1.17
−0.0548
0.0371
1.54
0.0521
1.71
−0.0337
0.0312
0.0183
2.18
−0.0409
−0.0196
−0.0348
−0.0002
0.0318
2.58
0.0200
2.91
−0.0499
−0.0224
0.0273
3.59
4.54
5.42
0.0177
283.25
−0.0027
0.0063
6.51
0.0032
2
2
2
3
3
3
3
3
3
3
88.45
93.35
98.25
03.25
08.15
13.35
18.15
23.05
27.95
33.05
8.03
0.0168
0.0117
9.33
−0.0222
0.0214
−0.0380
−0.0138
0.0564
ethanol
5.58
6.18
0.0048
6.80
−0.0268
−0.0196
0.0085
0.0055
7.86
−0.0143
−0.0022
−0.0444
0.0317
9.33
10.55
12.54
14.02
16.87
19.47
23.87
29.26
32.67
37.38
−0.0054
0.0204
−0.0253
−0.0011
−0.0161
0.0260
acetone
278.15
0.0636
2
2
2
2
3
3
3
3
83.25
88.45
93.25
98.35
03.35
08.15
13.25
18.05
−0.0477
−0.0389
−0.0442
0.0197
0.0541
−0.0012
−0.0439
−0.0257
0.0584
a
b
Relative standard uncertainty for x; u (x) = 0.02. Uncertainty for T;
u(T) = 0.01 K. Relative deviations; ε = |x − xi |/xi
r
c
cal
i
exp
exp
0.0556
i
0.0121
For each measurement, excessive DMPO and moderate solvent
were added to the equilibrium cell which was sealed by a rubber
stopper. The equilibrium cell was stirred for 2 h to 3 h to
ensure equilibrium at constant temperature. Then the stirring
was stopped and the solution was kept still for 4 h to 5 h. A
preheated injector withdrew 2 mL of the clear upper portion of
the solution which was transferred quickly to a previously
(m − m )/M
xexptl = (
2
0
1
m − m )/M + (m − m )/M
(1)
2
0
1
1
2
2
where M is the molar mass of DMPO and M is the molar
1
2
mass of the solvent. Different dissolution times were tested to
determine a suitable equilibrium time. It was discovered that 2
h was enough for DMPO to reach equilibrium in all solvents.
During our experiments, three parallel measurements were
carried out at the same composition of solvent for each
temperature, and an average value was calculated.
weighed measuring vial (m ). The vial was tightly and promptly
0
closed and weighed (m ) to obtain the mass of the sample (m1
1
−
m ). After that, the solvent in the vial was sufficiently
evaporated by a vacuum drying oven at about 333 K. The mass
0
of the vial (m ) was then obtained again. From the
2
3
. RESULTS AND DISCUSSION
thermogravimetric analysis, the decomposition temperature of
DMPO was found to be around 469.15 K. Consequently, we
can make certain that the DMPO solute cannot be volatilized at
a temperature used in the vacuum evaporation of the solvent.
The experimental mole fraction solubility in different organic
The mole fraction solubilities (x) of DMPO in selected solvents
were summarized in Table 2 and plotted as ln x vs temperature
in Figure 4. The temperature dependence of the solubility of
DMPO in seven monosolvents is represented by the modified
5
6−11
pure solvents is calculated by eq 1:
Apelblat equation:
C
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Article
1
/2
2
⎡
⎢
⎤
⎛
⎝
N
xiexp − xi
cal ⎞
⎠
1
N
⎥
RSD =
⎜∑
⎟
⎟
⎜
xiexp
⎢
⎣
⎥
i=1
⎦
(6)
where x ei xp stands for the experimental solubility, xi stands for
the solubility calculated from Apelblat equation; N represents
the number of data.
cal
The relative deviation ε is defined as
i
|
xical − x
|
exp
i
εi =
exp
xi
The average relative error σ is defined as
(7)
n
xical − xi
exp
1
n
σ/% = ∑
100
exp
xi
i=1
(8)
The results demonstrate that eq 2 can be applied to correlate
the solubility data with high accuracy from Figure 4, within the
temperature range of the measurement. A trend of increasing
solubility with temperature is observed. The order of solubility
of DMPO is as follows: methanol > ethanol ≈ chloroform >
acetone > acetonitrile ≈ 1,2-dichloroethane > ethyl acetate. For
a substance, the polarity and hydrogen bond of the solute will
affect its ability to dissolve in the solvent. The structure of
DMPO contains a hydroxyl group and its solubility
demonstrates the greatest value in the methanol and the
second in the ethanol, which contain the same hydroxyl
functional groups in agreement with the similar miscibility
Figure 4. Temperature dependence of the solubility of DMPO in
seven monosolvents: ★, methanol; ⧫, ethanol; ●, chloroform; ⬟,
acetone; ▲, acetonitrile; ▼, 1,2-dichloroethane; ■, ethyl acetate.
B
T/K
ln x = A +
+ C ln(T/K)
(2)
(3)
1
1,12
with
Δ C
Δ H
RTt1
fus p1
fus
1
A =
−
(ln T + 1) − a
t1
R
14−16
theory.
For the specific example of chloroform, it was deduced that
Δ C
hydrogen bonds in solution might play a dominant role in
Δ H
R
fus p1
fus
1
B = −
+
Tt1 − b
13,17
making a difference.
Because of the electronic withdrawing
(
(
4)
5)
R
ability properties of chlorine atoms, the chloroform contains a
reactive hydrogen. There are four oxygen atoms in DMPO
which can form different hydrogen bonds in the chloroform,
making DMPO very soluble in the chloroform solvent.
Because the throughput is a very significant target for
industry, a relatively high solubility of the compound is needed.
From Figure 4, it can be seen that the maximum solubility was
in methanol and ethanol, and the minimum value was observed
in ethyl acetate. Because of the toxicity of methanol, ethanol is
recommended as the best solvent for the purification of
DMPO.
Δ C
fus p1
C =
R
where x denotes the mole fraction solubility of DMPO and T
K) is the absolute temperature. Δ H (J·mol ) denotes the
enthalpy change upon the melting of the solute at its triple-
point temperature Tt1 (K), ΔfusCp1 (J·K ·mol ) is the
difference between the heat capacities of the solute in the
liquid and solid phases. Both a and b are constants. R (J·mol ·
−1
(
fus
1
−
1
−1
−
1
−
1
K ) is the molar gas constant.
4
. CONCLUSION
By means of the nonlinear fitting of the experimental
solubility data, the model parameters A, B, and C, which are
shown in Table 3, were acquired. The relative standard
The solubilities of DMPO in seven monosolvents were
measured by the gravimetrical method. At ambient temper-
ature, the solubility of DMPO in the selected solvents is
methanol > ethanol ≈ chloroform > acetone > acetonitrile ≈
1,2-dichloroethane > ethyl acetate. Obviously, the solubilities of
the DMPO increase with the rising temperature in seven
1
3
deviations (RSDs), defined by eq 6, are also presented in
Table 3. The RSD is used to distinguish the discrepancy
between the measured value and calculated data.
Table 3. Parameters of the Modified Apelblat Equation and Deviations for DMPO in Different Solvents
solvent
A
B
C
σ/%
RSD/%
R2
ethyl acetate
chloroform
acetonitrile
acetone
1192.98
−201.98
−296.13
488.54
−60067.86
6576.37
−175.33
30.74
44.78
−71.87
5.05
0.0837
0.0519
0.0355
0.1086
0.0135
0.0187
0.0302
0.0096
0.0314
0.0137
0.0188
0.0306
0.0102
0.0651
0.9938
0.9937
0.9970
0.9924
0.9974
0.9977
0.9981
10406.64
−25297.27
−919.47
5501.01
methanol
−29.77
−191.78
−227.92
1,2-dichloroethane
29.34
34.60
ethanol
7773.98
D
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Journal of Chemical & Engineering Data
Article
monosolvents, while the DMPO’s dissolving capacity are the
highest in methanol and ethanol and lowest in ethyl acetate.
Because of the toxicity of methanol, ethanol is the best solvent
for recrystallization of DMPO. The results show that the
Apelblat model is capable of representing the data with high
accuracy. The root-mean-square deviation was less than 0.010
(15) Schmid, R. Recent advances in the description of the structure
of water, the hydrophobic effect, and the like-dissolves-like rule.
Monatsh. Chem. 2001, 132, 1295−1326.
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(
17) Adam, A.; Paul, V. R. S. A survey of C−H groups as proton
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AUTHOR INFORMATION
■
*
+
Corresponding Author
E-mail: ruilanfan@imu.edu.cn. Tel.: +86-0471-4992982. Fax:
86-0471-4992982.
Funding
We appreciate the Natural Science Foundation of Inner
Mongolia (2013MS0215) for financial support.
Notes
The authors declare no competing financial interest.
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