Article pubs.acs.org/jced
Densities and Viscosities for the Ternary System of Cyclopropanemethanol (1) + n‑Dodecane (2) + Butylcyclohexane (3) and Corresponding Binaries at T = 293.15−343.15 K Xinxin Cheng,† Yitong Dai,† Jing Zhao,† Jianzhou Wu,† Haiyun Sun,‡ Yongsheng Guo,*,† and Wenjun Fang† †
Department of Chemistry, Zhejiang University, Hangzhou 310058, China Beijing Key Laboratory of Research and Application for Aerospace Green Propellants, Beijing Institute of Aerospace Testing Technology, Beijing 100000, China
‡
S Supporting Information *
ABSTRACT: Densities (ρ) and viscosities (η) for the ternary system cyclopropanemethanol (1) + n-dodecane (2) + butylcyclohexane (3) and three corresponding binary systems have been measured at 11 temperatures from 293.15 to 343.15 K under atmospheric pressure. The excess molar volumes (VEm) and viscosity deviations (Δη) of binary systems have been calculated and fitted to the Redlich−Kister equation, while data of the ternary system have been fitted to the Clibuka, Singh, Nagata−Tamura, and Redlich−Kister equations, respectively. The value of the VEm of the investigated systems is positive, while the value of Δη is negative over the entire concentration range; the results are illustrated through molecular interactions and structural effects.
1. INTRODUCTION Jet fuel, a type of aviation fuel used for aircraft, is mainly composed of acyclic alkanes and cycloalkanes. Conventionally, acyclic alkanes include nonane, dodecane, and tridecane, and cycloalkanes mainly refer to methylcyclohexane, ethylcyclohexane, and butylcyclohexane.1−3 High-density jet fuel is one of the hot spots of aviation fuel research in recent years. It possesses a higher density and higher volumetric energy content and can provide more propulsion energy for volume-limited aircraft. However, some new problems come along with an increase of the fuel density, such as ignition delay and inefficient combustion.4,5 Thus, fuel additives become a simple and indispensable tool to avoid these drawbacks and improve fuel performance. As one of the typical oxygenated additives, alcohols have been added into biodiesel fuels to enhance the octane rating of fuel, improve fuel burning characteristics, and reduce atmospheric pollution for decades.6−8 Therefore, there is a great possibility that alcohol additives can also improve the combustion performance of high-density jet fuels. Cyclopropanemethanol, an alcohol with a three-membered ring, has a higher density than those frequently used alcohol additives in biodiesel fuels, such as methanol, butanol, and so on.9 Since the high strain energy from the cyclopropyl rings can probably promote the combustion of fuel, cyclopropanemethanol becomes a potential fuel additive, which is able to improve the combustion performance without reducing the volumetric energy content of fuel.10 The addition of additives into the fuel can alter the fundamental physical properties of fuel. These properties are related © 2017 American Chemical Society
not only to the physical storage and transportation of fuel but also to its chemical combustion performance. For example, density of fuel mixtures is in connection with the volumetric energy content and the power output of the engine; viscosity affects its injection timing and pressure, atomization quality, size of fuel drop, etc.11−13 Therefore, the measurement and analysis of accurate physical data of fuel blending with alcohols are certainly helpful for the research of jet fuel additives. As an extension of our work concerning the thermodynamic study of jet fuel, in this work, as the model fuels, n-dodecane and butylcyclohexane have been blended with cyclopropanemethanol to prepare a series of mixtures at different mole ratios, and the densities as well as viscosities of the mixtures are measured and analyzed. Scilicet, densities and viscosities of ternary mixtures, cyclopropanemethanol + n-dodecane + butylcyclohexane, and corresponding binary mixtures, cyclopropanemethanol + n-dodecane, cyclopropanemethanol + butylcyclohexane, and n-dodecane + butylcyclohexane, have been measured in this article. Furthermore, the excess molar volumes, VEm, and the viscosity deviations, Δη, of these systems are calculated and analyzed to provide important information for the research of jet fuel additives. Received: February 22, 2017 Accepted: June 12, 2017 Published: July 10, 2017 2330
DOI: 10.1021/acs.jced.7b00201 J. Chem. Eng. Data 2017, 62, 2330−2339
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Table 1. Specification of Chemicals in This Work compound
source
CAS no.
provided mass fraction purity
measured mass fraction purity
analysis method
cyclopropanemethanol n-dodecane butylcyclohexane
Maclin Aladdin Aladdin
2516-33-8 112-40-3 1678-93-9
≥0.98 ≥0.99 ≥0.99
0.994 0.998 0.997
GC−MS GC−MS GC−MS
Table 2. Comparisons of Experimental Densities (ρ) and Viscosities (η) for Pure Compounds with the Literature Data at Corresponding Temperatures and Pressure P = 0.1 MPaa T/K
this study
293.15 298.15 303.15 308.15 313.15 318.15 323.15 328.15 333.15 338.15 343.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15 328.15 333.15 338.15 343.15
0.74883 0.74523 0.74160 0.73797 0.73433 0.73068 0.72701 0.72335 0.71967 0.71598 0.71228 1.481 1.355 1.244 1.151 1.066 0.992 0.926 0.867 0.814 0.765 0.724
0.7489223 0.7451723 0.7416623 0.7379523 0.7343823 0.7306923 0.7270723 0.7235623 0.7197323 0.7161623 0.7123423 1.48923 1.35923 1.24623 1.14823 1.06123 0.98423 0.91623 0.85523 0.80023 0.75123 0.70623
293.15 298.15 303.15 308.15 313.15 ρ/g·cm−3 318.15 323.15 328.15 333.15 338.15 343.15 η/mPa·s 293.15 298.15 303.15 308.15 313.15 318.15 323.15 328.15 333.15 338.15 343.15 Cyclopropanemethanol 293.15 298.15 303.15 308.15 ρ/g·cm−3 313.15 318.15 323.15 328.15
0.79934 0.79559 0.79184 0.78807 0.78430 0.78052 0.77674 0.77293 0.76913 0.76530 0.76147 1.305 1.202 1.112 1.033 0.963 0.901 0.844 0.794 0.749 0.708 0.670
0.79944 0.79570 0.79195 0.78819 0.78441 0.78049 0.77670
0.91299 0.90894 0.90485 0.90074 0.89658 0.89238 0.88813 0.88384
0.91130
property
literature
AARD/%
n-Dodecane
ρ/g·cm−3
η/mPa·s
0.74889 0.74514 0.74163 0.73788 0.73434 0.73060 0.72703 0.72329 0.71969
± ± ± ± ± ± ± ± ±
0.000524 0.000125 0.000524 0.000125 0.000524 0.000125 0.000524 0.000125 0.000524
0.7122 ± 0.000524 1.490 ± 0.00824 1.250 ± 1.167 ± 1.060 ± 0.99826 0.916 ± 0.87326 0.799 ±
0.74874 ± 0.000125 0.74152 ± 0.000125 0.73424 ± 0.000125 0.72695 ± 0.000125
1.500 ± 0.00522
0.00824 0.00522 0.00824
1.265 ± 0.00522
0.00824
0.93226
0.00824
0.81926
1.081 ± 0.00522
0.704 ± 0.00824
0.011 0.010 0.008 0.007 0.007 0.006 0.006 0.019 0.006 0.025 0.010 0.803 0.294 0.767 0.816 0.808 0.707 0.868 1.045 1.183 1.864 2.550
Butylcyclohexane ± ± ± ± ± ± ±
0.0000522 0.0000522 0.0000522 0.0000522 0.0000522 0.0000527 0.0000512
0.79933 0.79563 0.79182 0.78812 0.78428 0.78065 0.77670
± ± ± ± ± ± ±
0.0000512 0.0000527 0.0000512 0.0000527 0.0000512 0.0000528 0.0000527
0.79937 ± 0.0000527 0.79188 ± 0.0000527 0.78435 ± 0.0000527
0.006 0.009 0.007 0.011 0.008 0.010 0.005
0.76909 ± 0.0000512
0.76909 ± 0.0000527
0.7614 ± 0.0000512 1.296 ± 0.00522 1.196 ± 0.00522 1.107 ± 0.00522 1.027 ± 0.00522 0.958 ± 0.00522 0.899 ± 0.00428 0.83(7) ± 0.0112
0.76143 ± 0.0000527 1.31 ± 0.0112 1.200 ± 0.00429 1.12 ± 0.0112 1.032 ± 0.00428 0.96(1) ± 0.0112 0.835 ± 0.00429
0.007 0.436 0.334 0.419 0.341 0.313 0.222 0.479
0.73(5) ± 0.0112
0.741 ± 0.00429
1.492
0.64(8) ± 0.0112
0.663 ± 0.00429
2.225
0.005
1.302 ± 0.00429 1.111 ± 0.00429 0.962 ± 0.00429
0.218
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Table 2. continued T/K
property
Cyclopropanemethanol 333.15 338.15 343.15 293.15 298.15 303.15 308.15 313.15 η/mPa·s 318.15 323.15 328.15 333.15 338.15 343.15 a
this study
literature
AARD/%
0.87949 0.87507 0.87062 4.029 3.485 3.037 2.661 2.344 2.074 1.843 1.646 1.476 1.328 1.201
Standard uncertainties u are u (P) = 0.20 Kpa, u (T) = 0.01 K, ur (ρ) = 0.0005, ur (η) = 0.01
Table 3. Measured Densities (ρ) at Different Mole Fractions (x1) for the Binary Mixtures of Cyclopropanemethanol (1) + n-Dodecane (2), Cyclopropanemethanol (1) + Butylcyclohexane (2), and n-Dodecane (1) + Butylcyclohexane (2) at T = 293.15−343.15 K and Pressure P = 0.1 MPaa ρ/g·cm−3 x1 0.0000 0.1135 0.2127 0.3059 0.3804 0.5067 0.6019 0.7011 0.7921 0.8991 1.0000 0.0000 0.1039 0.2031 0.3022 0.3997 0.4993 0.5994 0.7000 0.7970 0.9004 1.0000 0.0000 0.1017 0.1996 0.2951 0.4221 0.5126 0.6256 0.7002 0.7989 0.9012 1.0000 a
293.15 K
298.15 K
303.15 K
308.15 K
Cyclopropanemethanol (1) + n-Dodecane (2) 0.74883 0.74523 0.74160 0.73797 0.75480 0.75108 0.74735 0.74360 0.76138 0.75763 0.75386 0.75006 0.76871 0.76492 0.76110 0.75726 0.77549 0.77168 0.76783 0.76396 0.78946 0.78559 0.78169 0.77776 0.80262 0.79872 0.79479 0.79082 0.81964 0.81570 0.81173 0.80772 0.83953 0.83557 0.83156 0.82752 0.87068 0.86669 0.86266 0.85859 0.91299 0.90894 0.90485 0.90074 Cyclopropanemethanol (1) + Butylcyclohexane (2) 0.79934 0.79559 0.79184 0.78807 0.80382 0.80002 0.79616 0.79228 0.80939 0.80552 0.80161 0.79768 0.81590 0.81200 0.80804 0.80406 0.82334 0.81939 0.81540 0.81139 0.83212 0.82815 0.82414 0.82009 0.84255 0.83856 0.83452 0.83045 0.85510 0.85109 0.84704 0.84295 0.86968 0.86566 0.86160 0.85750 0.88905 0.88502 0.88095 0.87684 0.91299 0.90894 0.90485 0.90074 n-Dodecane (1) + Butylcyclohexane (2) 0.79934 0.79559 0.79184 0.78807 0.79277 0.78905 0.78532 0.78158 0.78682 0.78312 0.77941 0.77569 0.78136 0.77768 0.77399 0.77028 0.77455 0.77090 0.76722 0.76353 0.76999 0.76635 0.76268 0.75901 0.76459 0.76096 0.75730 0.75364 0.76120 0.75757 0.75392 0.75027 0.75692 0.75330 0.74966 0.74601 0.75270 0.74909 0.74545 0.74181 0.74883 0.74523 0.74160 0.73797
313.15 K
318.15 K
323.15 K
328.15 K
333.15 K
338.15 K
343.15 K
0.73433 0.73984 0.74624 0.75340 0.76006 0.77381 0.78682 0.80368 0.82345 0.85448 0.89658
0.73068 0.73606 0.74240 0.74951 0.75613 0.76982 0.78278 0.79961 0.81933 0.85032 0.89238
0.72701 0.73226 0.73854 0.74560 0.75218 0.76579 0.77871 0.79548 0.81517 0.84612 0.88813
0.72335 0.72845 0.73466 0.74165 0.74819 0.76173 0.77460 0.79132 0.81096 0.84186 0.88384
0.71967 0.72462 0.73075 0.73768 0.74417 0.75764 0.77044 0.78711 0.80670 0.83756 0.87949
0.71598 0.72077 0.72681 0.73368 0.74012 0.75350 0.76625 0.78285 0.80239 0.83319 0.87507
0.71228 0.71691 0.72285 0.72964 0.73603 0.74932 0.76200 0.77854 0.79803 0.82877 0.87062
0.78430 0.78838 0.79372 0.80006 0.80734 0.81602 0.82634 0.83882 0.85335 0.87269 0.89658
0.78052 0.78447 0.78974 0.79603 0.80327 0.81190 0.82219 0.83465 0.84917 0.86850 0.89238
0.77674 0.78053 0.78574 0.79197 0.79916 0.80775 0.81801 0.83044 0.84494 0.86426 0.88813
0.77293 0.77657 0.78171 0.78787 0.79501 0.80356 0.81378 0.82618 0.84066 0.85997 0.88384
0.76913 0.77260 0.77765 0.78375 0.79083 0.79933 0.80950 0.82187 0.83633 0.85562 0.87949
0.76530 0.76860 0.77356 0.77959 0.78661 0.79505 0.80518 0.81751 0.83194 0.85121 0.87507
0.76147 0.76458 0.76940 0.77539 0.78235 0.79073 0.80080 0.81309 0.82749 0.84674 0.87062
0.78430 0.77782 0.77196 0.76657 0.75984 0.75532 0.74997 0.74660 0.74235 0.73816 0.73433
0.78052 0.77407 0.76822 0.76285 0.75614 0.75163 0.74629 0.74293 0.73869 0.73450 0.73068
0.77674 0.77030 0.76447 0.75912 0.75242 0.74793 0.74260 0.73925 0.73502 0.73084 0.72701
0.77293 0.76652 0.76071 0.75537 0.74870 0.74422 0.73890 0.73556 0.73133 0.72716 0.72335
0.76913 0.76273 0.75694 0.75162 0.74496 0.74049 0.73519 0.73186 0.72764 0.72348 0.71967
0.76530 0.75893 0.75316 0.74785 0.74121 0.73675 0.73147 0.72814 0.72394 0.71978 0.71598
0.76147 0.75512 0.74937 0.74407 0.73745 0.73300 0.72773 0.72441 0.72022 0.71608 0.71228
Standard uncertainties u are u(P) = 0.20 Kpa, u(x) = 0.0002, u(T) = 0.01 K, and ur(ρ) = 0.0005. 2332
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Figure 2. Energy profiles (kcal/mol) for the interaction of two cyclopropanemethanol molecules.
Figure 3. Comparisons of excess molar volumes, VEm, of n-dodecane + butylcyclohexane in this work and in the literature at T = 293.15 and 313.15 K. Data in this work: □, 293.15 K; ☆, 313.15 K. Data in the literature: ■, 293.15 K; ★, 313.15 K.22
ternary mixtures are prepared by mass with a Mettler Toledo AL204 analytical balance. The precision of the analytical balance is ±0.0001 g, and the uncertainty in the mole fractions was calculated to be 0.0002. 2.2. Methods. Densities of pure components and their mixtures were obtained at the temperature range from 293.15 to 343.15 K and P = 0.1 MPa in the present work, by means of an Anton Paar DMA 5000 M calibrated with dry air and double distilled water periodically. The densitometer is automatically stable within ±0.01 K, and with the consideration of purities of samples, the relative uncertainty for density is 0.0005. Viscosities of all samples were measured through an AMVn viscometer supplied by Anton Paar under the same conditions. The calibration of the viscometer was carried out with double distilled water. The efflux deflected time and temperatures of the apparatus were accurate to ±0.001 s and ±0.01 K, respectively. In addition, the relative uncertainty of viscosity is 0.01 in the present work. The measured densities and viscosities of pure compounds used in this work and the corresponding literature data are listed in Table 2. The absolute average relative deviations (% AARD) are calculated by eq 1. The results show that our data are in good agreement with the values in the literature
Figure 1. Excess molar volumes, VEm, as a function of the mole fraction of cyclopropanemethanol or n-dodecane for the binary systems of (a) cyclopropanemethanol + n-dodecane, (b) cyclopropanemethanol + butylcyclohexane, and (c) n-dodecane + butylcyclohexane at 0.1 MPa and 11 different temperatures: ■, 293.15 K; ●, 298.15 K; ▲, 303.15 K; ▼, 308.15 K; ⧫, 313.15 K; ◀, 318.15 K; ▶, 323.15 K; ⬢, 328.15 K; ★, 333.15 K; △, 338.15 K; ▽, 343.15 K; −, the Redlich−Kister correlations.
n
% AARD = (100/n) ×
∑ i=1
2. EXPERIMENTAL SECTION 2.1. Materials. The analyzed mixtures were prepared using the following compounds: cyclopropanemethanol, n-dodecane, and butylcyclohexane, all of which were obtained from commercial sources. The mass fraction purity of these chemicals was better than 0.99 verified by an Agilent 7890A/5975C GC-MS. All chemicals were directly used to make up the mixture, and more detailed descriptions are listed in Table 1. The binary and
Plit − P Plit
(1)
In the above equations, Plit stands for the value in the literature, and P means the corresponding measured data.
3. RESULTS AND DISCUSSION The excess molar volumes, VEm, and viscosity deviations, Δη, of the binary and ternary mixtures at different temperatures and atmospheric pressure were calculated with eq 2 and eq 3, respectively. The calculated values of binary systems and the 2333
DOI: 10.1021/acs.jced.7b00201 J. Chem. Eng. Data 2017, 62, 2330−2339
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Table 4. Measured Viscosities (η) at Different Mole Fractions (x1) for the Binary Mixtures of Cyclopropanemethanol (1) + n-Dodecane (2), Cyclopropanemethanol (1) + Butylcyclohexane (2), and n-Dodecane (1) + Butylcyclohexane (2) at T = 293.15−343.15 K and Pressure P = 0.1 MPaa η/mPa·s x1 0.0000 0.1039 0.2032 0.3022 0.3997 0.4993 0.5994 0.7000 0.7970 0.9004 1.0000 0.0000 0.1039 0.2031 0.3022 0.3997 0.4993 0.5994 0.7000 0.7970 0.9004 1.0000 0.0000 0.1017 0.1996 0.2951 0.4221 0.5126 0.6256 0.7002 0.7989 0.9012 1.0000 a
293.15 K
298.15 K
303.15 K
308.15 K
Cyclopropanemethanol (1) + n-Dodecane (2) 1.481 1.355 1.244 1.151 1.484 1.354 1.241 1.142 1.521 1.382 1.276 1.171 1.605 1.455 1.325 1.213 1.683 1.520 1.380 1.258 1.884 1.688 1.521 1.378 2.084 1.854 1.662 1.497 2.335 2.068 1.842 1.650 2.671 2.350 2.081 1.853 3.205 2.801 2.463 2.176 4.029 3.485 3.037 2.661 Cyclopropanemethanol (1) + Butylcyclohexane (2) 1.305 1.202 1.112 1.033 1.319 1.212 1.117 1.034 1.383 1.265 1.162 1.072 1.475 1.343 1.228 1.128 1.602 1.451 1.319 1.205 1.778 1.601 1.448 1.315 2.006 1.790 1.607 1.450 2.299 2.038 1.817 1.628 2.670 2.355 2.084 1.855 3.230 2.821 2.480 2.192 4.029 3.485 3.037 2.661 n-Dodecane (1) + Butylcyclohexane (2) 1.305 1.202 1.112 1.033 1.319 1.215 1.123 1.043 1.334 1.228 1.135 1.053 1.348 1.241 1.146 1.063 1.369 1.258 1.162 1.076 1.384 1.272 1.173 1.086 1.404 1.289 1.187 1.100 1.418 1.300 1.197 1.108 1.437 1.318 1.211 1.122 1.457 1.335 1.226 1.137 1.481 1.355 1.244 1.151
313.15 K
318.15 K
323.15 K
328.15 K
333.15 K
338.15 K
343.15 K
1.066 1.055 1.079 1.114 1.153 1.254 1.355 1.485 1.658 1.933 2.344
0.992 0.977 0.998 1.028 1.060 1.146 1.232 1.343 1.491 1.725 2.074
0.926 0.909 0.927 0.952 0.979 1.052 1.125 1.220 1.346 1.546 1.843
0.867 0.849 0.864 0.884 0.907 0.969 1.031 1.112 1.221 1.391 1.646
0.814 0.794 0.806 0.823 0.843 0.896 0.948 1.018 1.111 1.257 1.476
0.765 0.745 0.755 0.769 0.785 0.831 0.875 0.935 1.015 1.141 1.328
0.724 0.702 0.709 0.721 0.734 0.773 0.811 0.862 0.931 1.039 1.201
0.963 0.960 0.984 1.040 1.106 1.198 1.314 1.466 1.659 1.947 2.344
0.901 0.895 0.919 0.963 1.019 1.098 1.197 1.327 1.491 1.735 2.074
0.844 0.837 0.861 0.894 0.941 1.010 1.094 1.205 1.345 1.555 1.843
0.794 0.784 0.808 0.832 0.873 0.931 1.003 1.098 1.220 1.399 1.646
0.749 0.736 0.758 0.777 0.812 0.862 0.923 1.005 1.109 1.264 1.476
0.708 0.697 0.718 0.733 0.767 0.801 0.853 0.923 1.012 1.146 1.328
0.670 0.656 0.668 0.684 0.709 0.746 0.790 0.850 0.928 1.043 1.201
0.963 0.971 0.980 0.989 1.001 1.009 1.021 1.029 1.041 1.054 1.066
0.901 0.908 0.915 0.923 0.934 0.942 0.952 0.959 0.969 0.980 0.992
0.844 0.851 0.858 0.864 0.874 0.881 0.890 0.896 0.905 0.915 0.926
0.794 0.800 0.806 0.812 0.821 0.827 0.834 0.840 0.848 0.858 0.867
0.749 0.754 0.759 0.763 0.771 0.775 0.781 0.787 0.794 0.803 0.814
0.708 0.712 0.716 0.721 0.728 0.733 0.738 0.742 0.749 0.756 0.765
0.670 0.674 0.678 0.682 0.687 0.691 0.696 0.701 0.708 0.715 0.724
Standard uncertainties u are u (P) = 0.20 Kpa, u (x) = 0.0002, u (T) = 0.01 K, ur (η) = 0.01
Figure 4. Viscosity deviations, Δη, as a function of the mole fraction of cyclopropanemethanol or n-dodecane for the binary systems of (a) cyclopropanemethanol + n-dodecane and (b) cyclopropanemethanol + butylcyclohexane at P = 0.1 MPa and 11 different temperatures: ■, 293.15 K; ●, 298.15 K; ▲, 303.15 K; ▼, 308.15 K; ⧫, 313.15 K; ◀, 318.15 K; ▶, 323.15 K; ⬢, 328.15 K; ★, 333.15 K; △, 338.15 K; ▽, 343.15 K; −, the Redlich−Kister correlations. 2334
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Table 5. Measured Densities (ρ) at Different Mole Fractions (x1) for the Ternary Mixtures of Cyclopropanemethanol (1) + n-Dodecane (2) + Butylcyclohexane (3) at T = 293.15−343.15 K and Pressure P = 0.1 MPaa ρ/g·cm−3
a
x1
x2
293.15 K
298.15 K
303.15 K
308.15 K
313.15 K
318.15 K
323.15 K
328.15 K
333.15 K
338.15 K
343.15 K
0.1032 0.1023 0.1012 0.0978 0.1034 0.1031 0.1013 0.1007 0.2016 0.2032 0.2003 0.2030 0.2015 0.2004 0.2130 0.3005 0.3014 0.2985 0.3003 0.3085 0.2940 0.3989 0.3994 0.3990 0.4035 0.4010 0.5013 0.4991 0.5003 0.4941 0.5974 0.6007 0.5998 0.6960 0.6972 0.7991
0.0997 0.1995 0.2989 0.4022 0.4979 0.5971 0.6885 0.7982 0.0995 0.1990 0.2993 0.3979 0.4990 0.5982 0.6879 0.1005 0.1991 0.3012 0.3991 0.4943 0.5831 0.1007 0.2009 0.3036 0.3978 0.5006 0.1000 0.2028 0.2994 0.3973 0.1031 0.1996 0.3017 0.1023 0.2016 0.0999
0.79695 0.79041 0.78423 0.77813 0.77315 0.76804 0.76347 0.75849 0.80170 0.79484 0.78811 0.78209 0.77614 0.77062 0.76637 0.80742 0.79990 0.79241 0.78598 0.78012 0.77455 0.81396 0.80548 0.79744 0.79094 0.78384 0.82206 0.81236 0.80392 0.79597 0.83061 0.82084 0.81121 0.84123 0.82979 0.85503
0.79313 0.78660 0.78047 0.77437 0.76941 0.76432 0.75978 0.75478 0.79784 0.79102 0.78431 0.77830 0.77238 0.76686 0.76262 0.80354 0.79604 0.78861 0.78216 0.77652 0.77074 0.81004 0.80160 0.79357 0.78709 0.78001 0.81813 0.80844 0.80016 0.79209 0.82665 0.81691 0.80730 0.83725 0.82584 0.85103
0.78929 0.78279 0.77667 0.77059 0.76564 0.76056 0.75604 0.75104 0.79396 0.78716 0.78047 0.77448 0.76857 0.76307 0.75884 0.79962 0.79214 0.78474 0.77830 0.77261 0.76692 0.80610 0.79767 0.78968 0.78321 0.77614 0.81414 0.80448 0.79626 0.78818 0.82265 0.81293 0.80334 0.83324 0.82186 0.84700
0.78543 0.77895 0.77286 0.76680 0.76186 0.75680 0.75228 0.74730 0.79006 0.78328 0.77661 0.77064 0.76475 0.75927 0.75503 0.79568 0.78823 0.78084 0.77443 0.76871 0.76307 0.80212 0.79372 0.78574 0.77930 0.77224 0.81013 0.80050 0.79230 0.78424 0.81862 0.80893 0.79936 0.82919 0.81783 0.84293
0.78156 0.77510 0.76903 0.76299 0.75806 0.75301 0.74851 0.74353 0.78613 0.77937 0.77273 0.76677 0.76090 0.75543 0.75120 0.79170 0.78428 0.77692 0.77053 0.76482 0.75920 0.79810 0.78973 0.78178 0.77535 0.76832 0.80608 0.79648 0.78831 0.78027 0.81454 0.80488 0.79534 0.82510 0.81376 0.83882
0.77766 0.77123 0.76518 0.75918 0.75424 0.74921 0.74472 0.73975 0.78218 0.77544 0.76882 0.76289 0.75703 0.75158 0.74735 0.78770 0.78031 0.77297 0.76660 0.76091 0.75530 0.79406 0.78571 0.77779 0.77138 0.76436 0.80200 0.79243 0.78428 0.77627 0.81043 0.80080 0.79129 0.82097 0.80966 0.83467
0.77375 0.76734 0.76131 0.75531 0.75040 0.74538 0.74091 0.73595 0.77820 0.77149 0.76489 0.75897 0.75313 0.74770 0.74348 0.78368 0.77631 0.76899 0.76264 0.75698 0.75137 0.78999 0.78167 0.77377 0.76738 0.76038 0.79789 0.78834 0.78022 0.77223 0.80628 0.79668 0.78719 0.81679 0.80552 0.83047
0.76982 0.76342 0.75742 0.75144 0.74654 0.74154 0.73708 0.73214 0.77420 0.76751 0.76094 0.75503 0.74921 0.74379 0.73958 0.77962 0.77227 0.76498 0.75865 0.75298 0.74742 0.78587 0.77759 0.76971 0.76334 0.75636 0.79373 0.78422 0.77612 0.76815 0.80209 0.79252 0.78306 0.81257 0.80133 0.82623
0.76586 0.75950 0.75352 0.74756 0.74267 0.73768 0.73323 0.72830 0.77016 0.76350 0.75695 0.75107 0.74526 0.73987 0.73566 0.77552 0.76820 0.76094 0.75463 0.74898 0.74343 0.78173 0.77347 0.76562 0.75927 0.75231 0.78954 0.78005 0.77198 0.76404 0.79786 0.78831 0.77888 0.80830 0.79709 0.82193
0.76189 0.75554 0.74959 0.74365 0.73878 0.73381 0.72937 0.72446 0.76610 0.75946 0.75294 0.74707 0.74129 0.73591 0.73171 0.77140 0.76410 0.75686 0.75057 0.74493 0.73941 0.77754 0.76931 0.76149 0.75516 0.74822 0.78530 0.77584 0.76780 0.75988 0.79358 0.78406 0.77466 0.80398 0.79280 0.81758
0.75790 0.75158 0.74565 0.73973 0.73487 0.72991 0.72549 0.72059 0.76201 0.75540 0.74890 0.74305 0.73729 0.73193 0.72773 0.76723 0.75997 0.75276 0.74649 0.74086 0.73537 0.77332 0.76512 0.75732 0.75101 0.74410 0.78101 0.77159 0.76358 0.75569 0.78924 0.77976 0.77038 0.79960 0.78846 0.81318
Standard uncertainties u are u(P) = 0.20 Kpa, u(x) = 0.0002, u(T) = 0.01 K, and ur(ρ) = 0.0005. k
ternary system are given in Tables S1 and S2 and Tables S3 and S4 of the Supporting Information, respectively.
ΔY = x(1 − x) ∑ Ai (2x − 1)i − 1 i=1
N
VmE
=
∑ xiMi[(1/ρ) − (1/ρi )] i=1
5
(2)
∑ xiηi i=1
3
ΔY = x(1 − x) ∑ ∑ Aij × 101 − j(2x − 1)i − 1(T /K − T0)
N
Δη = η −
(4)
i=1 j=1
(5) (3)
In the above equation, x is the mole fraction of cyclopropanemethanol or n-dodecane, and ΔY is the calculated excess molar volumes or viscosity deviations of the binary mixtures. T is the absolute temperature, and T0 is 280.15 K. Ai, presented in Table S5, is the polynomial coefficients of eq 4 obtained by the least-squares correlation and F-test, and Aij presented in Table S6 is the polynomial coefficients of eq 5 obtained using the Marquardt15 algorithm. The excess molar volumes and viscosity deviations of ternary systems were fitted to eq 6. In eq 6, ΔY123 is excess molar volumes and viscosity deviations of the ternary mixtures; Y12, Y23, and Y13 denote the contribution of the binary system i-j to the ternary
In the above equations, i stands for a pure compound, and xi and Mi represent the mole fraction of one compound in a mixture and its molar mass, respectively. N is the number of components in a mixture. The excess molar volumes and viscosity deviations of binary systems were correlated to the Redlich−Kister equation (eq 4 and eq 5).14 In eq 4, the excess molar volumes and viscosity deviations were fitted as a function of composition according to the expression. In eq 5, the calculated data were fitted simultaneously to temperature and the mole fraction according to Redlich−Kister equation 2335
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system and are evaluated from the corresponding binary Redlich−Kister polynomial (eq 4) with the ternary composition xi and xj. Δ123 represents the contribution of the ternary effect, and four typical semiempirical equations (eq 7 to eq 10) were used to fit the ternary data of excess molar volumes and viscosity deviations. ΔY123 = Y12 + Y13 + Y23 + Δ123
(6)
Cibulka: Δ123 = x1x 2x3(C1 + C2x1 + C3x 2)
(7)
Singh: Δ123 = x1x 2x3[A + Bx1(x 2 − x3) + Cx12(x3 − x 2)]
(8)
Nagata−Tamura: Δ123 = x1x 2x3RT (B0 − B1x1 − B2 x 2 − B3x12 − B4 x 22 − B5x1x 2 − B6 x13 − B7 x 23 − B8x12x 2)
(9)
Redlich−Kister: Δ123 = x1x 2x3[A + B(x1 − x 2) + C(x 2 − x3) + D(x3 − x1) + E(x1 − x 2)2 + F(x 2 − x3)2 + G(x3 − x1)2 + ...]
(10)
In the above equations, xi is the mole fraction of compound i, R is the gas constant, and T is the absolute temperature. The values of the adjustable parameters of the different empirical equations were obtained by the least-squares correlation and F-test. The data were presented in Tables S7−S10, respectively. The standard deviations (σ) were calculated using the following equation: ⎡ ∑ (Y − Y )2 ⎤1/2 cal ⎥ σ=⎢ ⎣ (n − k ) ⎦
(11)
In the above equation, n is the number of experimental points, and k is the number of polynomial coefficients. The calculated results were illustrated in Tables S5−S10. The measured densities for three binary systems are listed in Table 3, and the changes of calculated excess molar volumes with composition are shown in Figure 1. Currently accepted theories suggested that the calculated excess molar volumes are influenced by chemical interactions, physical interactions, and structural effects.16,17 For the binary mixtures cyclopropanemethanol with n-dodecane or butylcyclohexane, it is obvious that the excess molar volumes are positive over the entire range of molar fractions at all designed temperatures. The maximum values of VmE are both at the mole fractions of cyclopropanemethanol from 0.4 to 0.5. Phenomena above mainly is caused by the change of hydrogen bonding between alcohol molecules. It is generally known that cyclopropanemethanol is a highly polar compound and strongly self-associated through hydrogen bonding. When nonpolar compounds, such as n-dodecane and butylcyclohexane, make contact with cyclopropanemethanol, the cyclopropanemethanol molecules with a permanent pole can induce a dipole in the nonpolar compound molecule. Then the induction forces between polar molecule and nonpolar molecule will form, which is also called the Debye force, one of the chemical intermolecular forces. This kind of intermolecular force will weaken the hydrogen bonding between cyclopropanemethanol molecules, so positive VmE of the binary mixtures can be observed. For both binary systems, the absolute value of excess molar volumes is growing with a rise in
Figure 5. Curves of VmE/cm3·mol−1 for the ternary system cyclopropanemethanol (1) + n-dodecane (2) + butylcyclohexane (3) correlated by the Nagata−Tamura equation at (a) T = 298.15 K and (b) T = 333.15 K.
temperature. This result may also connect with the change of hydrogen bonding. The hydrogen bonding in cyclopropanemethanol molecules will become weaker at high temperature, which means the hydrogen bonding between cyclopropanemethanol molecules will be easier to destroy and more positive excess molar volumes will be shown as a result. The absolute value of excess molar volumes of cyclopropanemethanol with n-dodecane is larger than that with butylcyclohexane, which can be attributed to the influence of dispersion force. Dispersion force is the main type of physical intermolecular force, and as the value of the molecular weight becomes larger, it will become stronger and lead to more positive excess molar volumes. To investigate the interaction between cyclopropanemethanol molecules, density functional theory (DFT) calculations are applied via Material Studio.18,19 First, two molecules of structural optimized cyclopropanemethanol were built with no interaction, and the total energy was calculated using Perdew−Wang generalized-gradient approximation (pw91-GGA).20,21 Subsequently, the two molecules were assembled within a certain distance to produce a single hydrogen bond. The geometry of the 2336
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Table 6. Measured Viscosities (η) for the Ternary Mixture of Cyclopropanemethanol (1) + n-Dodecane (2) + Butylcyclohexane (3) at T = 293.15−343.15 K and Pressure P = 0.1 MPaa η/mPa·s
a
x1
x2
293.15 K
298.15 K
303.15 K
308.15 K
313.15 K
318.15 K
323.15 K
328.15 K
333.15 K
338.15 K
343.15 K
0.1032 0.1023 0.1012 0.0978 0.1034 0.1031 0.1013 0.1007 0.2016 0.2032 0.2003 0.2030 0.2015 0.2004 0.2130 0.3005 0.3014 0.2985 0.3003 0.3085 0.2940 0.3989 0.3994 0.3990 0.4035 0.4010 0.5013 0.4991 0.5003 0.4941 0.5974 0.6007 0.5998 0.6960 0.6972 0.7991
0.0997 0.1995 0.2989 0.4022 0.4979 0.5971 0.6885 0.7982 0.0995 0.1990 0.2993 0.3979 0.4990 0.5982 0.6879 0.1005 0.1991 0.3012 0.3991 0.4943 0.5831 0.1007 0.2009 0.3036 0.3978 0.5006 0.1000 0.2028 0.2994 0.3973 0.1031 0.1996 0.3017 0.1023 0.2016 0.0999
1.337 1.351 1.371 1.386 1.403 1.418 1.438 1.458 1.391 1.409 1.425 1.446 1.466 1.477 1.511 1.482 1.501 1.515 1.537 1.568 1.534 1.612 1.630 1.647 1.673 1.690 1.791 1.802 1.821 1.830 2.002 2.029 2.054 2.288 2.309 2.672
1.226 1.240 1.257 1.269 1.284 1.299 1.316 1.331 1.272 1.288 1.302 1.320 1.337 1.347 1.375 1.350 1.366 1.378 1.396 1.423 1.426 1.460 1.475 1.489 1.511 1.524 1.610 1.619 1.635 1.642 1.784 1.810 1.830 2.029 2.046 2.353
1.131 1.142 1.159 1.169 1.182 1.193 1.210 1.222 1.169 1.183 1.195 1.210 1.226 1.235 1.257 1.235 1.249 1.260 1.276 1.298 1.301 1.328 1.341 1.353 1.372 1.384 1.454 1.463 1.476 1.483 1.605 1.625 1.642 1.810 1.824 2.085
1.047 1.057 1.070 1.080 1.091 1.102 1.116 1.126 1.078 1.091 1.102 1.114 1.129 1.136 1.156 1.134 1.147 1.157 1.171 1.189 1.193 1.214 1.224 1.234 1.252 1.262 1.321 1.328 1.340 1.345 1.449 1.465 1.479 1.623 1.635 1.857
0.972 0.981 0.993 1.002 1.012 1.020 1.034 1.042 0.998 1.010 1.019 1.030 1.043 1.049 1.066 1.047 1.058 1.066 1.078 1.094 1.099 1.114 1.123 1.132 1.147 1.155 1.206 1.211 1.221 1.226 1.312 1.328 1.340 1.462 1.473 1.663
0.904 0.913 0.924 0.932 0.941 0.948 0.961 0.967 0.927 0.938 0.946 0.956 0.967 0.972 0.987 0.968 0.978 0.986 0.997 1.011 1.014 1.026 1.034 1.042 1.055 1.063 1.104 1.109 1.118 1.122 1.197 1.208 1.219 1.323 1.332 1.495
0.846 0.853 0.863 0.870 0.878 0.884 0.897 0.901 0.864 0.873 0.881 0.889 0.899 0.904 0.917 0.899 0.908 0.914 0.926 0.937 0.940 0.948 0.956 0.962 0.974 0.981 1.015 1.020 1.027 1.031 1.094 1.104 1.114 1.202 1.210 1.349
0.793 0.799 0.809 0.814 0.821 0.827 0.839 0.842 0.807 0.815 0.822 0.830 0.839 0.843 0.855 0.837 0.845 0.851 0.861 0.871 0.875 0.879 0.886 0.892 0.902 0.908 0.936 0.940 0.947 0.951 1.002 1.013 1.022 1.097 1.103 1.223
0.744 0.751 0.759 0.765 0.770 0.776 0.787 0.789 0.756 0.764 0.771 0.776 0.785 0.789 0.799 0.781 0.790 0.794 0.804 0.812 0.816 0.818 0.824 0.830 0.839 0.844 0.866 0.870 0.876 0.880 0.924 0.932 0.940 1.004 1.010 1.112
0.701 0.707 0.715 0.720 0.725 0.730 0.741 0.741 0.710 0.718 0.723 0.729 0.736 0.740 0.749 0.732 0.740 0.744 0.752 0.759 0.763 0.763 0.769 0.774 0.782 0.786 0.804 0.808 0.813 0.817 0.854 0.861 0.869 0.923 0.928 1.016
0.663 0.668 0.675 0.680 0.684 0.689 0.699 0.698 0.669 0.676 0.681 0.686 0.693 0.695 0.704 0.687 0.695 0.698 0.706 0.712 0.716 0.714 0.719 0.724 0.731 0.735 0.750 0.752 0.757 0.760 0.791 0.799 0.805 0.851 0.856 0.931
Standard uncertainties u are u(P) = 0.20 Kpa, u(x) = 0.0002, u(T) = 0.01 K, and ur(η) = 0.01.
VEm−x1 curves in the literature follow the same trend as that in this work. Measured viscosities for all investigated binary systems are given in Table 4, and the calculated viscosity deviations are listed in Table S2. By observing Δη-x1 curves of binary systems cyclopropanemethanol with n-dodecane or butylcyclohexane in Figure 4, it is evident that viscosity deviations of mixtures are negative over the whole composition range and reach the minima for the mole fraction of cyclopropanemethanol at around 0.6. The negative viscosity deviations indicating that the addition of alkanes leads to the self-associated cyclopropanemethanol molecules dissociate, so the mixtures will show greater mobility comparing with pure cyclopropanemethanol. For the binary system n-dodecane with butylcyclohexane, the viscosity deviations are all very small and even could be neglected according to the experimental uncertainty. The above calculated result also shows the mixtures are almost ideal, consistent with the foregoing deduction. For the ternary system cyclopropanemethanol (1) + n-dodecane (2) + butylcyclohexane (3), the measured density
assembled system was optimized with pw91-GGA, and corresponding energy was also calculated. The energy change for this process is displayed in Figure 2. It is clear that cyclopropanemethanol molecules do strongly self-associate through hydrogen bonding, so the change of hydrogen bonding has a remarkable effect on the excess molar volumes of mixtures. For the binary system n-dodecane with butylcyclohexane, although, the calculated excess molar volumes are also positive in the entire composition range. The data in Table 3 show that all values of excess molar volumes are very small. Since n-dodecane and butylcyclohexane are both saturated aliphatic hydrocarbons, the above phenomenon indicates that these two alkanes composed an almost ideal solution. In this situation, the interaction energies between n-dodecane and butylcyclohexane are almost equal; it follows that there is a very small overall energy change when two substances are mixed, and only a tiny volume change on mixing can be observed. Liu et al. also reported the calculated excess molar volumes of the binary system n-dodecane with butylcyclohexane from 293.15 to 313.15 K, and the results of comparisons are shown in Figure 3.22 It can be seen that 2337
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absolute values of Δη decrease. Because n-dodecane and butylcyclohexane will form a nearly ideal liquid, therefore, the change of the cyclopropanemethanol mole fraction will play a decisive role in the value of viscosity deviation in the ternary system, and an almost straight line can be seen in Figure 6. In the present work, the Clibuka, Singh, Nagata−Tamura, and Redlich−Kister equations are chosen to correlate the data of excess volumes and viscosity deviations. Comparing the deviations of different equations, for the ternary system we investigated, only the Singh equation gives relatively large deviations. For the other three equations, there is no significant difference in the fitting ability to experimental data.
data are presented in Table 5, while the calculated excess molar volumes are listed in Table S3. The constant curves of VEm correlated by the Nagata−Tamura equation at T = 298.15 K and T = 333.15 K are shown in Figure 5. It can be easily seen from both diagrams that the VEm is positive in the entire concentration area at all temperatures, which is most likely due to the weakening of the hydrogen bond between the cyclopropanemethanol molecules. The absolute value of excess molar volumes is increasing with the temperature increase as binary systems, which is attributed to the weakening of hydrogen bonding at high temperature. The measured viscosities data and calculated viscosity deviations for investigate ternary systems are listed in Table 6 and Table S4, respectively. Figure 6 presents the constant curves
4. CONCLUSION In this article, the densities and viscosities of the ternary system cyclopropanemethanol + n-dodecane + butylcyclohexane and binary systems cyclopropanemethanol + n-dodecane, cyclopropanemethanol + butylcyclohexane, and n-dodecane + butylcyclohexane have been measured over the wide temperature range from 293.15 to 343.15 K at atmospheric pressure. Additionally, on the basis of the measured data, the excess molar volume and viscosity deviations of these systems have been calculated, and the binary data have been fitted to the Redlich− Kister equation, while the ternary data have been fitted to the Clibuka, Singh, Nagata−Tamura, and Redlich−Kister equations, respectively. It can be seen that the excess molar volumes are positive over the entire composition range for ternary and all binary systems. The results suggest that the nonideal behavior of the mixtures is mainly affected by the breaking of hydrogen bonding between cyclopropanemethanol molecules. On the contrary, the viscosity deviations are negative at 11 studied temperatures for all investigated mixtures, which are induced by the dissociation of cyclopropanemethanol molecules. These results will be very useful for the research of the high-density liquid hydrocarbon fuels additives.
■
ASSOCIATED CONTENT
S Supporting Information *
The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jced.7b00201. Values of excess molar volumes (VmE) and viscosity deviations (Δη) for binary and ternary systems; coefficients and deviations of VEm and Δη with the semiempirical equation for binary and ternary systems (PDF)
■
AUTHOR INFORMATION
Corresponding Author
*Phone: +86-571-88981416. Fax: +86-571-88981416. E-mail:
[email protected]. ORCID
Figure 6. Curves of Δη/mPa·s−1 for the ternary system cyclopropanemethanol (1) + n-dodecane (2) + butylcyclohexane (3) correlated by the Nagata−Tamura equation at (a) T = 298.15 K and (b) T = 333.15 K.
Yongsheng Guo: 0000-0001-7609-1891 Wenjun Fang: 0000-0002-5610-1623 Funding
The authors are grateful for financial support from the National Natural Science Foundation of China (Grant No. J1210042).
of Δη correlated by the Nagata−Tamura equation at T = 298.15 K and T = 333.15 K. As what can be concluded from the behavior of the binary mixtures, the Δη of ternary systems is negative over the whole concentration range, and a rise in temperature makes
Notes
The authors declare no competing financial interest. 2338
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DOI: 10.1021/acs.jced.7b00201 J. Chem. Eng. Data 2017, 62, 2330−2339
