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Cite This: J. Chem. Eng. Data XXXX, XXX, XXX−XXX
Solubility Determination, Correlation, and Solute−Solvent Molecular Interactions of 5‑Aminotetrazole in Various Pure Solvents Zhicai He,† Jieyu Zhang,† Xin Gao,† Tian Tang,† Xianfang Yin,† Jia Zhao,‡ Rongrong Li,† and Deman Han*,† †
School of Pharmaceutical and Materials Engineering, Taizhou University, Taizhou, Zhejiang 318000, P. R. China Industrial Catalysis Institute of Zhejiang University of Technology, Hangzhou 310014, P. R. China
‡
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S Supporting Information *
ABSTRACT: The purpose was to evaluate solubility data and solute−solvent molecular interactions of 5-aminotetrazole in various pure solvents including methanol, ethanol, n-propanol, isopropanol, 1-butanol, toluene, acetone, acetonitrile, ethyl acetate, 1,4-dioxane, N,N-dimethylformamide (DMF), and Nmethyl pyrrolidone (NMP) at temperatures “T = 283.15−323.15 K” and pressure “P = 0.1 MPa”. Solubility data were determined by the isothermal saturation method with the help of high-performance liquid-phase chromatography. Solubility data of 5-aminotetrazole obtained in mole fraction showed the maximum value in DMF (7.951 × 10−2), followed by NMP (7.415 × 10−2), 1,4-dioxane (6.523 × 10−2), toluene (3.811 × 10−3), isopropanol (1692 × 10−3), ethanol (1.752 × 10−3), acetone (1.620 × 10−3), n-propanol (1.566 × 10−3), methanol (1.470 × 10−3), ethyl acetate (1.393 × 10−3), 1-butanol (1.315 × 10−3), and acetonitrile (3.85 × 10−4) at T = 323.15 K. Moreover, properties of solvents such as the polarity and the Hildebrand solubility parameters were analyzed as well. The function of solubility values in pure solvents and the temperature were evaluated by the modified Apelblat equation and the λh equation. The maximum values of the relative average deviation and root-mean-square deviation are no more than 1.58 × 10−2 and 4.43 × 10−4, respectively, which indicated that good correlation was recorded between the experimental and calculated data. Then, the Akaike information criterion was used to select the more suitable model. Obtaining solubility data and correlative model parameters of 5-aminotetrazole and understanding the intermolecular forces in different solvents are particularly important in industrial synthesis and separation.
1. INTRODUCTION Tetrazoles are a representative class of synthetic organic heterocyclic compounds with a high nitrogen content and good stability, and they can tolerate a wide range of chemical environments, from strongly acidic to basic as well as oxidizing and reducing conditions.1−3 Although tetrazoles and their derivatives rarely appear in nature, most of them show biological activity. In particular, they have applications in both materials science and pharmaceuticals.4 5-Aminotetrazole (its chemical structure is shown in Figure 1), also known as C-aminotetrazole, has a nitrogen content rated above 82.3% (mass fraction) and can be used as a raw material to produce a variety of high-performance materials with excellent properties.5,6 In the automobile-manufacturing industry, it can be used as an airbag filler for automobiles.7,8 As a pharmaceutical product, it shows anti-allergic and anti-
asthmatic, antiviral and anti-inflammatory, antineoplastic, and cognition disorder activities.9−11 Recently, most domestic and foreign manufacturers use ethyl acetate, N,N-dimethylformamide (DMF), dimethyl sulfoxide, and other organic solvents as the solvent for reactions. Under the action of a phase-transfer catalyst, multiple extraction, distillation, separation, and other complicated processes are used to prepare 5-aminotetrazole salt; it is then acidified to obtain a crude 5-aminotetrazole, which is purified to give 5-aminotetrazole.12−15 Therefore, research on the separation of 5-aminotetrazole has a high value of practical application. In this work, solubility data of 5-aminotetrazole in various pure solvents including methanol, ethanol, n-propanol, isopropanol, 1-butanol, toluene, acetone, acetonitrile, ethyl acetate, 1,4-dioxane, N,N-dimethylformamide (DMF), and Nmethyl pyrrolidone (NMP) at temperatures “T = 283.15− 323.15 K” and pressure “P = 0.1 MPa” were determined by the isothermal saturation method. Moreover, the properties of solvents such as polarity, dipole moment, dielectric constants, and Hildebrand solubility parameters were analyzed as well. Received: May 1, 2019 Accepted: August 5, 2019
Figure 1. Chemical structure of 5-aminotetrazole. © XXXX American Chemical Society
A
DOI: 10.1021/acs.jced.9b00385 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
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stopped and the solutions were permitted to settle for 2 h before sampling. Then, a 1 ml preheated syringe connected with a filter (PTFE 0.2 um) was used to extract the supernatant; the sample was transferred instantaneously to a 25 ml preweighted volumetric flask and weighed using an analytical balance, and then 5 μl of the solution was taken out to test by high-performance liquid-phase chromatography. The detection parameters were as follows: a type of reverse-phase column (LP-C18, 250 mm × 4.6 mm), a temperature of 303.15 K, a UV detector with a wavelength of 210 nm, and chromatographic-grade methanol as the mobile phase with a flow rate of 1.0 ml·min−1. Each experiment was repeated three times. After sampling, a new temperature was set and the experiment was started again. The solubility data of 5-aminotetrazole (xw,T) in pure solvents were obtained by eq 1
Solubility data were correlated by the modified Apelblat equation and the λh equation. Subsequently, the Akaike information criterion (AIC) was used to select the more suitable model.
2. EXPERIMENTAL SECTION 2.1. Materials. 5-Aminotetrazole, 0.98 in mass fraction, as determined by high-performance liquid-phase chromatography, was purchased from Shanghai Maclin Reagent Co., Ltd. The crude compound was recrystallized three times with anhydrous ethanol, and the final purity was 0.992. Methanol, ethanol, n-propanol, isopropanol, 1-butanol, toluene, acetone, acetonitrile, ethyl acetate, 1,4-dioxane, DMF, and NMP were provided by Sinopharm Chemical Reagent Co., Ltd., China, and these solvents were of analytical grade. Before the experiment, molecular sieves were added to the solvents used in the experiment to remove a small amount of water molecules. The source and purity of the materials used are listed in Table 1.
x w,T =
chemicals 5-aminotetrazole
85.07
methanol ethanol n-propanol isopropanol 1-butanol acetonitrile acetone ethyl acetate toluene 1,4-dioxane N,N-dimethylformamide N-methyl pyrrolidone
32.04 46.07 60.10 60.10 74.12 41.05 58.08 88.11 92.14 88.11 73.09 99.13
source Shanghai Maclin Reagent Co., Ltd Sinopharm Chemical Reagent Co., Ltd.,China
mass fraction purity
analytical method
0.992
HPLCa
0.996b 0.995 0.996 0.997 0.995 0.996 0.995 0.995 0.996 0.995 0.995 0.995
none
(1)
where m1 stands for the mass of 5-aminotetrazole and m2 stands for the mass of methanol, ethanol, n-propanol, isopropanol, 1-butanol, toluene, acetone, acetonitrile, ethyl acetate, 1,4-dioxane, DMF, or NMP. M1 and M2 are the corresponding molar masses.
Table 1. Sources and Purity of the Materials Used in the Work molar mass g mol−1
m1/M1 m1/M1 + m2 /M 2
3. RESULTS AND DISCUSSION 3.1. Solubility Data. The results of experimental solubility in methanol, ethanol, n-propanol, isopropanol, 1-butanol, toluene, acetone, acetonitrile, ethyl acetate, 1,4-dioxane, DMF, and NMP at all of the temperatures are listed in Table 2. The relationship between temperature and solubility data (in mole fraction) is shown graphically in Figure 2, and the results in mass fraction are presented in Figure S1 in the Supporting Information. From Table 2, solubility data of 5aminotetrazole in mole fraction were obtained, and they showed the maximum value in DMF (7.951 × 10−2), followed by NMP (7.415 × 10−2), 1,4-dioxane (6.523 × 10−2), toluene (3.811 × 10−3), isopropanol (1692 × 10−3), ethanol (1.752 × 10−3), acetone (1.620 × 10−3), n-propanol (1.566 × 10−3), methanol (1.470 × 10−3), ethyl acetate (1.393 × 10−3), 1butanol (1.315 × 10−3), and acetonitrile (3.85 × 10−4) at T = 323.15 K. Three obvious phenomena could be found in Figures 2 and S1: first, the solubility data increase with increasing temperature in all evaluated solvents; second, in alcoholic solvents, the solubility decreases with the increase of the carbon chain length, with the order of mass solubility data methanol > ethanol > isopropanol > n-propanol > 1-butanol, but there is no such phenomenon in the order of molar solubility; third, the solubility in DMF, NMP, and 1,4-dioxane is much higher than that in other solvents. According to Table S1 in the Supporting Information, the polarity and the Hildebrand solubility parameters of the alcoholic solvents18 decrease in the following order: methanol > ethanol > n-propanol> isopropanol > 1-butanol. The result of mass fraction solubility in Figure S1 shows that the solubility of 5-aminotetrazole decreases with decreasing polarity and Hildebrand solubility parameters of the solvents except for isopropanol. This phenomenon also exists in solvents with a high solubility (DMF, NMP, 1,4-dioxane, and toluene). Compared with the less polar solvents of 1,4-dioxane and toluene, the solubility data of acetone, ethyl acetate, and acetonitrile are lower. The reason for this phenomenon can be
a
High-performance liquid-phase chromatography. bThe purity was provided by the supplier.
2.2. Solubility Measurement. The solubility data of 5aminotetrazole in various pure solvents including methanol, ethanol, n-propanol, isopropanol, 1-butanol, toluene, acetone, acetonitrile, ethyl acetate, 1,4-dioxane, DMF, and NMP at temperatures “T = 283.15−323.15 K” and pressure P = 0.1 MPa were determined by the isothermal saturation method.16,17 The reliability of our experimental technique has been verified in our previous work.16,17 5-Aminotetrazole (an excess of solid powder was used) and 50 ml of pure solvent were added into the jacketed vessel. A magnetic stirrer at 400 rpm was used to ensure the equilibrium of solutions at different temperatures. Moreover, the experimental temperature was controlled by a circulating water bath, and the monitoring of the experiment temperature (with an accuracy of ±0.05 K) was performed by a bulb thermometer, which was inserted into the solution. In addition, a reflux condenser was directly connected to the vessel to prevent solvent evaporation. To ensure the equilibrium of solutions at different temperatures, the magnetic stirrer continuously stirred for over 24 h. After that, the stirring was B
DOI: 10.1021/acs.jced.9b00385 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
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Table 2. Experimental and Calculated Mole Fraction Solubilities of 5-Aminotetrazole in Different Pure Solvents in the Temperature Range of T = (283.15−323.15) K Under 101.1 kPaa 100× methanol
n-propanol
ethanol
isopropanol
T/K
exp
calcdApel
calcdλh
exp
calcdApel
calcdλh
exp
calcdApel
calcdλh
exp
calcdApel
calcdλh
283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15
0.0615 0.0681 0.0764 0.0858 0.0954 0.1062 0.1179 0.1315 0.1470
0.0614 0.0685 0.0765 0.0853 0.0952 0.1062 0.1184 0.1319 0.1469 1-butanol
0.0608 0.0683 0.0767 0.0858 0.0958 0.1067 0.1186 0.1316 0.1458
0.0800 0.0896 0.0990 0.1094 0.1207 0.1328 0.1453 0.1599 0.1752
0.0803 0.0892 0.0989 0.1093 0.1206 0.1327 0.1458 0.1598 0.1749 acetonitrile
0.0805 0.0893 0.0988 0.1092 0.1204 0.1325 0.1457 0.1599 0.1754
0.0694 0.0773 0.0868 0.0962 0.1063 0.1173 0.1290 0.1420 0.1567
0.0697 0.0776 0.0863 0.0957 0.106 0.1172 0.1293 0.1424 0.1566 ethyl acetate
0.0696 0.0776 0.0863 0.0957 0.106 0.1171 0.1292 0.1424 0.1567
0.0762 0.0853 0.0946 0.1050 0.1161 0.1279 0.1408 0.1541 0.1692
0.0763 0.0851 0.0947 0.105 0.1161 0.128 0.1407 0.1543 0.1689 acetone
0.0767 0.0852 0.0946 0.1047 0.1157 0.1276 0.1405 0.1545 0.1698
exp
calcdApel
calcdλh
exp
calcdApel
calcdλh
exp
calcdApel
calcdλh
exp
calcdApel
calcdλh
0.0455 0.0510 0.0577 0.0660 0.0755 0.0869 0.1001 0.1151 0.1315
0.045 0.0511 0.0581 0.0663 0.0758 0.0868 0.0996 0.1144 0.1315 1,4-dioxane
0.0438 0.0507 0.0585 0.0673 0.0771 0.088 0.1002 0.1138 0.1289
0.0193 0.0213 0.0235 0.0256 0.0280 0.0304 0.0329 0.0357 0.0385
0.0193 0.0213 0.0234 0.0256 0.028 0.0304 0.033 0.0357 0.0385 toluene
0.0195 0.0214 0.0233 0.0255 0.0278 0.0302 0.0329 0.0358 0.0389
0.0499 0.0572 0.0649 0.0734 0.0834 0.0943 0.1068 0.1221 0.1393
0.0503 0.057 0.0646 0.0733 0.0832 0.0945 0.1074 0.1221 0.1388 NMP
0.0494 0.0567 0.0649 0.074 0.0842 0.0954 0.1079 0.1216 0.1369
0.0749 0.0832 0.0916 0.1016 0.1117 0.1231 0.1354 0.1488 0.1620
0.0749 0.0831 0.092 0.1016 0.112 0.1232 0.1353 0.1483 0.1623 DMF
0.075 0.0831 0.092 0.1015 0.1119 0.1231 0.1352 0.1484 0.1626
exp
calcdApel
calcdλh
exp
calcdApel
calcdλh
exp
calcdApel
calcdλh
exp
calcdApel
calcdλh
1.780 2.167 2.674 3.276 3.929 4.626 5.506 6.523
1.776 2.191 2.678 3.247 3.905 4.662 5.526 6.506
1.782 2.19 2.672 3.238 3.896 4.657 5.531 6.528
0.1348 0.1556 0.1767 0.2011 0.2287 0.2596 0.2945 0.3348 0.3811
0.1361 0.1551 0.1766 0.2011 0.2287 0.2601 0.2955 0.3354 0.3805
0.1342 0.1545 0.1772 0.2025 0.2306 0.2618 0.2963 0.3346 0.3769
2.232 2.649 3.115 3.660 4.319 5.015 5.768 6.570 7.415
2.203 2.644 3.141 3.699 4.32 5.003 5.75 6.561 7.436
2.241 2.657 3.132 3.671 4.279 4.962 5.726 6.577 7.521
2.843 3.260 3.796 4.368 4.933 5.588 6.281 7.074 7.951
2.844 3.29 3.784 4.33 4.931 5.589 6.307 7.086 7.93
2.852 3.291 3.779 4.321 4.919 5.578 6.302 7.094 7.958
283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15
283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15 a
Standard uncertainty values u are u(T) = 0.02 K, u (p) = 400 Pa; the relative standard uncertainty in mole fraction ur is ur(x) = 0.036.
Figure 2. Experimental solubility data in mole fraction of 5-aminotetrazole in different pure solvents.
explained by the empirical rule “like dissolves like”. Both solute and solvent molecules have ring structures, which help them attract each other. The stronger the intermolecular interactions between the solute and solvent molecules, the greater the solubility. However, the solubility in polar alcohols, except in 1-butanol, is higher than that in acetone, ethyl acetate, and acetonitrile. Here, we should consider not only the role of polarity but also the hydrogen-bonding between solvents and
solutes. Therefore, the solubility order is not completely consistent with the polarity and the Hildebrand solubility parameter order, which indicates that these are not the only factors to affect the solubility data. It should be noted that dissolution is a complex process; it is affected by various factors, such as the different physical properties of the solute and the solvent as well as solvating interactions, especially the hydrogen-bond interaction. C
DOI: 10.1021/acs.jced.9b00385 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
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Table 3. Parameters of the Modified Apelblat Equation and λh Equation for 5-Aminotetrazole in Different Solvents Along with the Values of RAD and RMSD λh equation
modified Apelblat equation solvent
A
B
C
100 RAD
10 RMSD
λ
h
100 RAD
104 RMSD
methanol ethanol n-propanol isopropanol 1-butanol acetonitrile acetone ethyl acetate toluene 1,4-dioxane NMP DMF
−81.145 −26.712 −37.298 −12.367 −151.842 3.118 −30.492 −117.391 −86.614 49.701 82.662 16.359
1640.724 −614.591 −206.233 −1295.086 4423.995 −1849.232 −439.081 2992.237 1623.857 −5347.732 −6233.521 −2869.537
12.036 3.853 5.448 1.729 22.761 −0.91 4.401 17.575 13.156 −6.21 −11.417 −1.733
0.25 0.28 0.31 0.11 0.49 0.15 0.23 0.32 0.24 0.54 0.47 0.37
0.026 0.038 0.035 0.017 0.041 0.005 0.033 0.026 0.056 2.15 2.05 2.13
0.007 0.006 0.006 0.006 0.011 0.001 0.005 0.01 0.029 2.221 1.206 0.767
256133.929 253606.108 267512.796 254425.069 201813.431 1354437.86 275947.179 211333.701 74650.57 1587.748 2312.744 3016.474
0.51 0.325 0.29 0.32 1.58 0.55 0.25 0.84 0.59 0.54 0.64 0.48
0.059 0.043 0.033 0.045 0.13 0.018 0.038 0.096 0.18 2.39 4.43 2.44
3.2. Correlation of Solubility Data. The solubility data were correlated by two semi-empirical equations: the modified Apelblat model19,20 and the λh equation.21,22 3.2.1. Modified Apelblat Equation. The function of solubility values in mole fraction (x) and the absolute temperature (T) could be expressed with the modified Apelblat equation,19,20 which is a semi-empirical equation and is shown as eq 2 ln x = A +
B + C ln T T
calculated and experimental values agree well; this indicates that the two equations can basically be used to correlate the results. The maximum value of RMSD is 4.43 × 10−4, which is obtained with the λh equation in NMP, and the RAD values are all less than 1.58%. 3.3. Akaike Information Criterion and Residual Analysis of the Two Models. To show the difference between the calculated and the experimental solubility and determine the more suitable correlation model, we performed statistical analyses of the experimental and calculated values. Therefore, the comparison between experimental and calculated values and residual plots along with the square of the linear correlation coefficient (R2) are shown in Figure 3. According to Figure 3, the values of R2 are very close to 1 in the two equations. However, through further analysis of the residual plot, we can find that except for some abnormal points, the data are basically close to the 0 point and show a trend of symmetrical distribution in the modified Apelblat equation and the λh equation. Therefore, these two models were analyzed by the Akaike information criterion (AIC).21 In general, the model with the lowest value of AIC can be supposed to be the best-fit model. The value of AIC for these two models is given as follows
(2)
where A, B, and C are the adjustable equation parameters and can be acquired by correlating the experimental solubility. 3.2.2. λh Equation. Another semi-empirical equation used is the λh equation, which is used to describe the solid−liquid equilibrium behavior of 5-aminotetrazole as well and is expressed as eq 3.21 The λh equation has two parameters λ and h: ÄÅ É ij 1 ÅÅ λ(1 − x) ÑÑÑÑ 1 yzz lnÅÅÅ1 + ÑÑ = λhjjj − z jT ÅÅÇ ÑÑÖ x Tm zz{ (3) k where λ and h are adjustable equation parameters, and Tm denotes the melting temperature of 5-aminotetrazole in Kelvin. Solubility data were correlated by the thermodynamic model with the least-squares method. Moreover, in this work, the relative average deviation (RAD) and root-mean-square deviation (RMSD) are employed, which are shown in eqs 5 and 5.16 RAD =
1 N
c e ij |x w,T − x w,T | yzz j j zz ∑ jj e z x w,T k {
ÄÅ N É ÅÅ ∑ (x c − x e)2 ÑÑÑ1/2 ÅÅ i = 1 i ÑÑ i ÑÑ RMSD = ÅÅÅ ÑÑ ÅÅ N ÑÑÖ ÅÇ
4
AIC = −2 ln L(θ ) + 2k
(6)
Here, L(θ) is the maximized likelihood value for the estimated model and k is the number of estimable parameters in the model. In the special case of least-squares estimation with normal distributed errors, apart from an additive constant, AIC can be simplified as follows
(4)
AIC = N ln(RSS/N ) + 2k
(7)
with N
(5)
RSS =
∑ (xie − xic)2
(8)
i=1
where the number of experimental data points is expressed as N. During the correlation process, the melting temperature (Tm) of 5-aminotetrazole was taken from ref 11. The regressed parameter values A, B, and C in the modified Apelblat equation and λ and h in the λh equation along with the RAD and RMSD values were listed in Table 3. By analyzing the RAD and RMSD values of the two models, the results show that the
e
c
Here, RSS is the residual sum of squares, x and x are the experimental and calculated solubility data of 5-aminotetrazole, and N is the number of observations. As shown in Table 4, the AIC values of the two equations are −1954.28 and −1866.06, respectively. The value in the Apelblat equation is relatively small. Therefore, the results of the Akaike information criterion and residual analysis indicated D
DOI: 10.1021/acs.jced.9b00385 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
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average deviation (RAD) and root-mean-square deviation (RMSD) are not more than 1.58 × 10−2 and 4.43 × 10−4, respectively. The results of the Akaike information criterion and residual analysis indicated that the modified Apelblat equation is more suitable to correlate solubility data.
■
ASSOCIATED CONTENT
S Supporting Information *
The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jced.9b00385.
■
Physical properties of the selected solvents; experimental solubility data in mass fraction of 5-aminotetrazole in different pure solvents (PDF)
AUTHOR INFORMATION
Corresponding Author
*E-mail:
[email protected]. Tel.: +86 576 88660177. ORCID
Rongrong Li: 0000-0001-6112-6203 Deman Han: 0000-0003-1995-0770 Funding
This study was financially supported by the Zhejiang Province Public Welfare Projects (No. 2017C31112 and LGF19B050002), Ministry of Education Cooperative Education Project (No. 201802066054), Chemical Engineering & Technology of Zhejiang Province First-Class Discipline (Taizhou University), Science and Technology Plan Project of Taizhou (1803gy01 and 1803gy03), National Natural Science Foundation of China (No. 21575097).
Figure 3. Comparison between experimental and calculated solubility data and the residual plot
Notes
The authors declare no competing financial interest.
■
Table 4. Value of the Akaike Information Criterion of the Modified Apelblat Equation and the λh Equation in Selected Solvents models
RSS
N
parameters
AIC
Apelblat equation λh equation
1.183 × 10−6 2.749 × 10−6
107 107
3 2
−1954.28 −1866.06
REFERENCES
(1) Gao, A.; Rheingold, A. L.; Brill, T. B. Thermal Decomposition of Energetic Materials. 47. A trigger linkage study of high-nitrogen content nitraminotetrazoles and nitramin-1,2,4-triazoles. Propellants, Explos., Pyrotech. 2010, 16, 97−104. (2) Zhang, J. G.; Niu, X. Q.; Zhang, S. W.; Zhang, T. L.; Huang, H. S.; Zhou, Z. N. Novel potential high-nitrogen-content energetic compound: Theoretical study of diazido-tetrazole (CN10). Comput. Theor. Chem. 2011, 964, 291−297. (3) Voitekhovich, S. V.; Talapin, D. V.; Klinke, C.; Kornowski, A.; Weller, H. CdS Nanoparticles Capped with 1-Substituted 5Thiotetrazoles: Synthesis, Characterization, and Thermolysis of the Surfactant. Chem. Mater. 2008, 20, 4545−4547. (4) Abdel-Rahman, A. A.; Ali, O. M.; Abdel-Megeed, A. S. Synthesis and Antimicrobial Activity of New Tetrazoles Incorporating Isoindole-1,3-dione Moiety and Their Sugar Derivatives. J. Heterocyclic Chem. 2013, 44, 484−489. (5) Klapötke, T. M.; Schmid, P. C.; Schnell, S.; Stierstorfer, J. 3,6,7Triamino-[1,2,4]triazolo[4,3-b][1,2,4]triazole: A Non-toxic, HighPerformance Energetic Building Block with Excellent Stability. Chem. - Eur. J. 2015, 21, 9219−9228. (6) Matsumoto, A. Sequence-Controlled Radical Copolymerization for the Design of High-Performanced Transparent Polymer Materials. In Sequence-Controlled Polymers: Synthesis, Self-Assembly, and Properties; American Chemical Society, 2014; Vol. 1170, pp 301−312. (7) Mei, X.; Yang, H.; Li, X.; Li, Y. C.; Cheng, Y. The effect of 5amino-1H-tetrazole on the combustion performance and ignition capability of boron/potassium nitrate igniter. J. Therm. Anal. Calorim. 2015, 120, 1749−1754. (8) Fujihisa, H.; Honda, K.; Obata, S.; Yamawaki, H.; Takeya, S.; Gotoha, Y.; Matsunaga, T. Crystal structure of anhydrous 5-
that the modified Apelblat equation is more suitable to correlate the solubility data of 5-aminotetrazole in all selected solvents.
4. CONCLUSIONS Solubility data of 5-aminotetrazole in methanol, ethanol, npropanol, isopropanol, 1-butanol, toluene, acetone, acetonitrile, ethyl acetate, 1,4-dioxane, DMF, and NMP were determined by the isothermal saturation method. Solubility data of 5-aminotetrazole obtained in mole fraction showed the maximum value in DMF (7.951 × 10−2), followed by NMP (7.415 × 10−2), 1,4-dioxane (6.523 × 10−2), toluene (3.811 × 10−3), isopropanol (1692 × 10−3), ethanol (1.752 × 10−3), acetone (1.620 × 10−3), n-propanol (1.566 × 10−3), methanol (1.470 × 10−3), ethyl acetate (1.393 × 10−3), 1-butanol (1.315 × 10−3), and acetonitrile (3.85 × 10−4) at T = 323.15 K. Moreover, properties of solvents such as the polarity and the Hildebrand solubility parameters were analyzed as well. The function of solubility values in pure solvents and the temperature were evaluated by the modified Apelblat equation and the λh equation. The maximum values of the relative E
DOI: 10.1021/acs.jced.9b00385 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
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DOI: 10.1021/acs.jced.9b00385 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
