Density, Viscosity, Surface Tension, and Refractive Index for Binary

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Density, Viscosity, Surface Tension, and Refractive Index for Binary Mixtures of 1,3-Dimethyladamantane with Four C10 Alkanes Xiaomei Qin,† Xiaofang Cao,† Yongsheng Guo,*,† Li Xu,† Shenlin Hu,‡ and Wenjun Fang*,† †

Department of Chemistry, Zhejiang University, Hangzhou 310027, China Science and Technology on Scramjet Laboratory, The 31st Research Institute of CASIC, Beijing 10074, China

‡

S Supporting Information *

ABSTRACT: For a comprehensive understanding of the properties of 1,3-dimethyladamantane (1,3-DMA) as a new potential candidate of high energy-density hydrocarbon fuels, densities, viscosities, surface tensions, and refractive indices for binary mixtures of 1,3-DMA with each of four C10 alkanes, n-decane, butylcyclohexane, decalin, and exo-tetrahydrodicyclopentadiene (JP10), are determined over the whole composition range at different temperatures ranging from (293.15 to 363.15) K and atmospheric pressure (0.1 MPa). The excess molar volume (VmE), the viscosity deviation (Δη), the surface tension deviation (Δγ), and the refractive index deviation (ΔnD) for these binary systems are calculated. All of the VmE values are negative over the whole composition range for these systems, and they show slight changes against the temperature. The Δη values for the systems except 1,3-DMA + JP-10 are negative, and the absolute values decrease obviously with rising temperature. The Δγ gives clearly negative values for the system of 1,3-DMA + n-decane and shows small values near zero for the other systems. Negligible values of ΔnD indicate that the refractive indices show nearly linear additions from those of two components for the binary mixtures. The results could provide important reference information for the development and performance of new high energy-density hydrocarbon fuels.

1. INTRODUCTION With the development of modern hypersonic aircrafts, the high propulsion performance of hydrocarbon fuels is needed.1−3 High energy-density hydrocarbon fuels have been attracting extensive attention due to their high volumetric heat values.4 The higher volumetric heating value of a fuel means that greater energy can be provided per unit volume, which is advantageous for improving the aircraft with restricted space. A high density hydrocarbon fuel usually refers to that with the density higher than 0.8 g·cm−3 (293.15 K). It can be a pure compound or a blended hydrocarbon fuel.5 To ensure fair evaluation of high energy-density hydrocarbon fuels, the physical properties of the fuels need to be known accurately. Density is a volumetric property which is closely related to the energy-density. Viscosity, as an important transport property, can influence the mass transfer characteristics of hydrocarbon fuels. Furthermore, the surface tension is a significant index of interfacial properties. The refractive index is an optical property which can reflect the purity of hydrocarbon fuels. However, with an increase of the density of a pure hydrocarbon fuel, the viscosity and surface tension usually trend to an undesirable increase. To solve the problem, appropriate fuel components or additives should be added to improve the performance of the hydrocarbon fuels. As an alkyl derivative of adamantane, 1,3-dimethyladamantane (1,3-DMA, shown in Figure 1e) has unique cyclic tetrahedral cage-like structure, and it can store energy through its strained cyclic geometry. 1,3-DMA has high density (0.9 g·cm−3, 293.15 K) and low freeze point (245.0 K).6 1,3-DMA has been expected to be used as one attractive candidate component of high density fuels or fuel additives.7 Paraffins and cycloalkanes are typical components of current hydrocarbon fuels. Pure alkanes are often used as model © 2014 American Chemical Society

Figure 1. Molecular structures of n-decane (a), butylcyclohexane (b), decalin (c), JP-10 (d), and 1,3-DMA (e).

fuels,8−11 and most of them have relatively low densities and viscosities. exo-Tetrahydrodicyclopentadiene (JP-10) is one of the high energy-density hydrocarbon fuels, and it is presently serving as missile fuel by the Navy and the Air Force in the U.S.A.12,13 Decalin is one important component of endothermic hydrocarbon fuels.10,14 Investigation on the physical properties of various mixtures with different fuel components is a fundamental work to obtain advanced hydrocarbon fuels with high energy-density. Received: October 7, 2013 Accepted: February 11, 2014 Published: February 21, 2014 775

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Table 1. Information of Chemicals in This Work

a

chemical name

molecular weights

source

provided mass fraction purity

purification method

measured mass fraction purity

analysis method

1,3-DMA n-decane butylcyclohexane decalin JP-10

164.29 142.28 140.27 138.25 136.24

TCIa Aladdin TCI Aladdin LRICIb

0.99 0.99 0.99 0.99 0.98

none none none none none

0.998 0.994 0.996 0.999 0.985

GC−MS GC−MS GC−MS GC−MS GC−MS

TCI is the abbreviation of Tokyo Chemical Industry. bLRICI is the abbreviation of Liming Research Institute of Chemical Industry, China.

a correction factor supplied by the manufacturer. The uncertainty of surface tension measurement is 0.01 mN·m−1. The refractive indices (nD) are measured using a WAY-2S refractometer. The measurement temperature is maintained by circulating water from the HAAKE circulator with a precision of ± 0.01 K. The uncertainty of the refractive index measurement is ± 0.0005.

In the present work, densities, viscosities, surface tensions, and refractive indices for four binary systems of 1,3-DMA with each of four C10 alkanes, n-decane, butylcyclohexane, decalin, and JP-10 (the molecular structures shown in Figure 1) are measured over the entire composition range at temperatures T = (293.15 to 363.15) K and atmospheric pressure p = 0.1 MPa over the entire composition range. The values of excess or deviation properties are then calculated and discussed. The results are hoped to provide reference information for the property optimization of new high energy-density hydrocarbon fuels.

3. RESULTS AND DISCUSSION The measured densities and viscosities of the pure liquids at T = 293.15 K and p = 0.1 MPa are compared with those from the ref 15−26 in Table 2. The experimental data are well in agreement

2. EXPERIMENTAL SECTION 2.1. Materials. 1,3-DMA (CAS Registry No. 702-79-4, mass fraction purity > 0.99) and butylcyclohexane (CAS Registry No. 1678-93-9, mass fraction purity >0.99) are supplied by Tokyo Chemical Industry (TCI) Co. Ltd., Tokyo, Japan. The 1,3-DMA sample is characterized by 1H NMR and GC−MS. The GC−MS and 1H NMR spectra are shown in Figures S1 and S2 of the Supporting Information. n-Decane (CAS Registry No. 124-18-5, mass fraction purity > 0.99) and decalin (CAS Registry No. 91-17-8, mass fraction purity > 0.99) are obtained from Aladdin Chemistry Co. Ltd., Shanghai, China. JP-10 (CAS Registry No. 2825-82-3) is obtained from Liming Research Institute of Chemical Industry (LRIC) in China, and the mass fraction purity is claimed to be better than 0.98. All of the reagents are checked by GC−MS (7890A/ 5975C, Agilent). The detailed information of the chemicals is listed in Table 1. The reagents are used without further purification. 2.2. Apparatus and Procedure. The densities, dynamic viscosities, and refractive indices of pure liquids and the binary mixtures over the whole concentration range are measured at temperatures T = (293.15 to 363.15) K and atmospheric pressure p = 0.1 MPa. The surface tensions of the systems are measured over the whole concentration range at temperature T = 313.15 K and atmospheric pressure p = 0.1 MPa. The densities (ρ) are measured with a DMA 5000 M density meter (Anton Paar). The temperature is controlled by an installed thermometer with an accuracy of ± 0.01 K. The uncertainty in measuring density is ± 0.00005 g·cm−3. The dynamic viscosities (η) are determined by using an AMVn viscometer (Anton Paar). The temperature is controlled by an installed thermometer with an accuracy of ± 0.01 K, and the accuracy of the efflux time measurement is ± 0.001 s. The combined uncertainty of the viscosity measurement in this work is ± 0.004 mPa·s. The surface tension (γ) is determined using a DropMeter A-100P tensiometer. The temperature is controlled by a PolyScience digital temperature controller with an accuracy of ± 0.01 K. The primary quantity measured is the volume of a drop that detaches from a capillary of known diameter. The γ value can be calculated by Vρ g γ= F (1) R where R is the radius of the capillary, V is the critical volume, ρ is the density of mixture, g is the gravitational acceleration constant, and F is

Table 2. Densities (ρ), Viscosities (η), Surface Tensions (γ), and Refractive Indices (nD) with Literature Data for Pure Components at Temperature T = 293.15 K and Atmospheric Pressure p = 0.1 MPaa compound 1,3-DMA n-decane butylcyclohexane decalin JP-10 1,3-DMA n-decane butylcyclohexane decalin JP-10

exptl

lit

ρ/g·cm−3 0.9016 0.9016b,c 0.7305 0.7300d 0.7995 0.7992f 0.8805 0.8803h 0.9357 0.9357i nD 1.4779 1.4783j 1.4123 1.4124k 1.4408 1.4408f 1.4731 1.4878 1.4877m

exptl

lit

η/mPa·s 3.779 0.928 0.925e 1.302 1.309g 2.507 2.504h 3.078 3.075i γ/mN·m−1 28.37 23.84 23.83l 27.15 30.95 31.89 31.86m

Standard uncertainties u are u(T) = 0.01 K, u(ρ) = 0.00005 g·cm−3, u(η) = 0.004 mPa, u(γ) = 0.01 mN·m−1 and u(nD) = 0.0005. b Reference 15. cReference 16. dReference 17. eReference 18. f Reference 19. gReference 20. hReference 21. iReference 22. j Reference 23. kReference 24. lReference 25. mReference 26. a

with the literature data. The results for systems of 1,3-DMA with n-decane, butylcyclohexane, decalin, or JP-10 are provided and discussed in the following part. 3.1. Volumetric Properties. The measured densities (ρ) of the binary mixtures at temperatures T = (293.15 to 363.15) K and atmospheric pressure p = 0.1 MPa are given in Table 3. The excess molar volumes (VmE) are calculated using the following equation: Vm E =

M1x1 + M 2x 2 ⎛ M1x1 Mx ⎞ − ⎜⎜ + 2 2 ⎟⎟ ρm ρ2 ⎠ ⎝ ρ1

(2)

where ρm is the density of a binary mixture of 1,3-DMA (1) + C10 alkane (2), and ρ1 and ρ2 are those of the pure components 1 and 2, respectively. x1, x2 and M1, M2 are the mole fractions and the molar masses of the two components, respectively. The calculated values of 776

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Table 3. Density (ρ) for the Binary Mixtures of 1,3-DMA (1) + C10 Alkane (2) with Different Mole Fraction (x1) at Temperatures T = (293.15 to 363.15) K and Atmospheric Pressure p = 0.1 MPaa ρ/g·cm−3 x1

a

293.15 K

298.15 K

303.15 K

0.0000 0.1028 0.1981 0.3019 0.3998 0.4996 0.6018 0.6968 0.7904 0.8950 1.0000

0.73053 0.74778 0.76395 0.78166 0.79847 0.81566 0.83334 0.84974 0.86583 0.88379 0.90165

0.72675 0.74402 0.76021 0.77793 0.79474 0.81194 0.82964 0.84608 0.86219 0.88018 0.89809

0.72296 0.74025 0.75645 0.77417 0.79101 0.80822 0.82594 0.84239 0.85854 0.87656 0.89453

0.0000 0.0830 0.1716 0.2652 0.3625 0.4617 0.5636 0.6620 0.7728 0.8838 1.0000

0.79947 0.80870 0.81844 0.82859 0.83896 0.84932 0.85974 0.86957 0.88036 0.89090 0.90165

0.79571 0.80496 0.81471 0.82486 0.83525 0.84562 0.85606 0.86592 0.87674 0.88731 0.89809

0.79196 0.80121 0.81097 0.82113 0.83151 0.84191 0.85236 0.86224 0.87309 0.88370 0.89453

0.0000 0.1034 0.2043 0.3050 0.4034 0.5024 0.6048 0.7046 0.8094 0.9013 1.0000

0.88046 0.88340 0.88608 0.88858 0.89090 0.89305 0.89512 0.89698 0.89878 0.90024 0.90165

0.87672 0.87967 0.88235 0.88487 0.88720 0.88937 0.89146 0.89335 0.89517 0.89665 0.89809

0.87296 0.87592 0.87861 0.88115 0.88349 0.88568 0.88779 0.88971 0.89156 0.89306 0.89453

0.0000 0.1021 0.2015 0.3018 0.4005 0.4981 0.6020 0.6998 0.8051 0.8993 1.0000

0.93574 0.93253 0.92930 0.92602 0.92275 0.91946 0.91586 0.91246 0.90873 0.90537 0.90165

0.93186 0.92865 0.92547 0.92221 0.91897 0.91570 0.91216 0.90878 0.90509 0.90177 0.89809

0.92795 0.92477 0.92162 0.91839 0.91518 0.91194 0.90844 0.90510 0.90144 0.89817 0.89453

313.15 K

323.15 K

1,3-DMA (1) + n-Decane (2) 0.71536 0.70842 0.73265 0.72580 0.74888 0.74192 0.76664 0.75964 0.78349 0.77640 0.80074 0.79358 0.81850 0.81129 0.83501 0.82780 0.85122 0.84400 0.86933 0.86210 0.88741 0.88017 1,3-DMA (1) + Butylcyclohexane (2) 0.78443 0.77716 0.79368 0.78635 0.80345 0.79609 0.81364 0.80623 0.82404 0.81662 0.83446 0.82704 0.84495 0.83754 0.85488 0.84749 0.86580 0.85847 0.87648 0.86920 0.88741 0.88017 1,3-DMA (1) + Decalin (2) 0.86543 0.85701 0.86841 0.86011 0.87113 0.86296 0.87370 0.86565 0.87607 0.86811 0.87829 0.87045 0.88045 0.87270 0.88241 0.87479 0.88432 0.87684 0.88587 0.87852 0.88741 0.88017 1,3-DMA (1) + JP-10 (2) 0.92013 0.91214 0.91700 0.90907 0.91390 0.90603 0.91074 0.90294 0.90759 0.89987 0.90442 0.89679 0.90099 0.89343 0.89772 0.89022 0.89414 0.88670 0.89095 0.88352 0.88741 0.88017

333.15 K

343.15 K

353.15 K

363.15 K

0.70069 0.71810 0.73429 0.75198 0.76874 0.78591 0.80371 0.82026 0.83662 0.85483 0.87299

0.69288 0.71039 0.72663 0.74430 0.76113 0.77840 0.79622 0.81286 0.82922 0.84750 0.86577

0.68500 0.70252 0.71878 0.73651 0.75336 0.77070 0.78859 0.80528 0.82170 0.84013 0.85852

0.67703 0.69462 0.71092 0.72868 0.74557 0.76297 0.78094 0.79771 0.81423 0.83271 0.85123

0.76955 0.77874 0.78845 0.79859 0.80900 0.81949 0.83004 0.84008 0.85111 0.86191 0.87299

0.76188 0.77107 0.78081 0.79098 0.80141 0.81194 0.82253 0.83260 0.84373 0.85461 0.86577

0.75416 0.76336 0.77309 0.78328 0.79378 0.80437 0.81500 0.82511 0.83631 0.84725 0.85852

0.74638 0.75555 0.76532 0.77554 0.78610 0.79672 0.80741 0.81757 0.82881 0.83987 0.85123

0.84945 0.85258 0.85543 0.85814 0.86065 0.86303 0.86533 0.86746 0.86957 0.87127 0.87299

0.84187 0.84504 0.84792 0.85066 0.85320 0.85561 0.85796 0.86010 0.86224 0.86400 0.86577

0.83426 0.83744 0.84037 0.84314 0.84572 0.84816 0.85054 0.85270 0.85488 0.85670 0.85852

0.82661 0.82981 0.83277 0.83558 0.83817 0.84065 0.84307 0.84529 0.84751 0.84936 0.85123

0.90425 0.90123 0.89829 0.89527 0.89227 0.88926 0.88596 0.88283 0.87937 0.87625 0.87299

0.89632 0.89335 0.89046 0.88750 0.88456 0.88159 0.87837 0.87532 0.87198 0.86895 0.86577

0.88834 0.88544 0.88261 0.87971 0.87684 0.87394 0.87082 0.86782 0.86458 0.86167 0.85852

0.88032 0.87745 0.87471 0.87187 0.86905 0.86624 0.86318 0.86028 0.85712 0.85429 0.85123

x1 is the mole fraction of 1,3-DMA in the binary mixtures. Standard uncertainties u are u(T) = 0.01 K, u(x) = 0.0001, u(ρ) = 0.00005 g·cm−3.

VmE for the four systems at different temperatures are summarized in Table S1 of the Supporting Information. The excess molar volumes are fitted to the Redlich−Kister type polynomial equation:

where Y is the excess molar volume (VmE), x1 is the mole fraction of 1,3-DMA in each binary mixture. The values of polynomial coefficients Ai are listed in Table S2 of the Supporting Information, along with the standard deviation (σ), which is defined as

k

Y = x1(1 − x1)∑ Ai (2x1 − 1)i ‐ 1 i=1

σ = [∑ (Y − Ycal)2 /(n − k)]1/2

(3) 777

(4)

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Figure 2. Excess molar volumes (VmE) with mole fraction of 1,3-DMA (x1) for the binary systems (a, 1,3-DMA + n-decane; b, 1,3-DMA + butylcyclohexane; c, 1,3-DMA + decalin; d, 1,3-DMA + JP-10) at different temperatures (T). Experimental data: □, 293.15 K; ○, 298.15 K; △, 303.15 K; ▽, 313.15 K; ◇, 323.15 K; left pointing arrow, 333.15 K; right pointing arrow, 343.15 K; ⬡, 353.15 K; ☆, 363.15 K.

where n is the total number of experimental datum points and k is the number of parameter. Y and Ycal refer to the experimental and calculated values of excess molar volumes, respectively. The variations of the excess molar volumes with the mole fraction of 1,3-DMA, along with the Redlich−Kister correlation results, are shown in Figure 2. It is indicated that the VmE values of all systems are negative over the entire range of mole fractions at each temperature. The VmE values decrease slightly with increasing temperature for the system of 1,3-DMA + n-decane, while they become less negative with increasing temperature for the systems of 1,3-DMA + butylcyclohexane/decalin/JP-10. The variation of VmE as a function of x1 for the four systems at temperature T = 313.15 K and atmospheric pressure p = 0.1 MPa is shown in Figure S3 of the Supporting Information. The VmE values for the system of 1,3-DMA + n-decane are more negative than those of other systems at the same mole fraction and temperature. The VmE values for the systems of 1,3-DMA + ndecane/butylcyclohexane/decalin become less negative with increasing ring number. The VmE values for the system of 1,3DMA + JP-10 are slightly smaller than those of 1,3-DMA + butylcyclohexane. The VmE values can be ascribed to the molecular structure and intermolecular interactions. As the mixtures of 1,3-DMA + C10

alkane are nonpolar systems, the physical intermolecular forces (i.e., van der Waals’ forces) should make weak contributions to the excess molar volume. Hence, the structural effects are the main influence factor of the VmE values for the four systems. Since 1,3-DMA is one kind of caged hydrocarbons and ndecane is a chain alkane, the intermolecular distance between two components in the system of 1,3-DMA + n-decane becomes much smaller than those in the other three systems with cyclic compounds. With increasing steric hinder for 1,3-DMA + n-decane/butylcyclohexane/decalin, the absolute values of VmE becomes smaller. JP-10 is a cyclic alkane containing C5 rings, and the space distance between two components in the system of 1,3-DMA + JP-10 might be smaller than that of 1,3-DMA and butylcyclohexane or decalin. Hence, the absolute values of VmE for the system of 1,3-DMA + JP-10 are larger than those for the systems of 1,3DMA + butylcyclohexane/decalin. 3.2. Viscometric Properties. The viscosities (η) of the binary mixtures at temperatures T = (293.15 to 363.15) K and atmospheric pressure p = 0.1 MPa are summarized in Table 4, and the changes with concentration are shown in Figure S4 of the Supporting Information. The viscosity data are correlated with the double-parameter McAllister equation: 778

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Table 4. Viscosities (η) for the Binary Mixtures of 1,3-DMA (1) + C10 Alkane (2) with Different Mole Fraction (x1) at Temperatures T = (293.15 to 363.15) K and Atmospheric Pressure p = 0.1 MPaa η/mPa·s x1

a

293.15 K

298.15 K

303.15 K

0.0000 0.1028 0.1981 0.3019 0.3998 0.4996 0.6018 0.6968 0.7904 0.8950 1.0000

0.928 1.016 1.120 1.253 1.402 1.581 1.828 2.125 2.491 3.031 3.779

0.864 0.942 1.035 1.154 1.287 1.445 1.665 1.926 2.247 2.719 3.371

0.807 0.877 0.961 1.069 1.187 1.328 1.526 1.757 2.040 2.456 3.027

0.0000 0.0830 0.1716 0.2652 0.3625 0.4617 0.5636 0.6620 0.7728 0.8838 1.0000

1.302 1.407 1.518 1.654 1.802 1.989 2.215 2.472 2.797 3.222 3.779

1.200 1.293 1.391 1.512 1.643 1.805 2.007 2.229 2.518 2.885 3.371

1.111 1.194 1.281 1.389 1.506 1.647 1.828 2.024 2.272 2.601 3.027

0.0000 0.1034 0.2043 0.3050 0.4034 0.5024 0.6048 0.7046 0.8094 0.9013 1.0000

2.507 2.607 2.713 2.812 2.919 3.039 3.167 3.310 3.465 3.622 3.779

2.272 2.361 2.449 2.53 2.628 2.728 2.844 2.967 3.102 3.237 3.371

2.070 2.148 2.227 2.299 2.384 2.468 2.570 2.675 2.799 2.909 3.027

0.0000 0.1021 0.2015 0.3018 0.4005 0.4981 0.6020 0.6998 0.8051 0.8993 1.0000

3.078 3.147 3.237 3.335 3.436 3.513 3.592 3.657 3.707 3.747 3.779

2.785 2.841 2.922 3.002 3.084 3.151 3.220 3.273 3.316 3.342 3.371

2.535 2.582 2.650 2.717 2.787 2.847 2.904 2.946 2.985 3.002 3.027

313.15 K

323.15 K

1,3-DMA (1) + n-Decane (2) 0.709 0.625 0.767 0.672 0.837 0.729 0.926 0.797 1.023 0.879 1.137 0.972 1.295 1.098 1.480 1.237 1.704 1.421 2.032 1.676 2.475 2.050 1,3-DMA (1) + Butylcyclohexane (2) 0.962 0.835 1.030 0.893 1.099 0.951 1.187 1.008 1.280 1.088 1.393 1.182 1.537 1.289 1.692 1.414 1.883 1.583 2.145 1.774 2.475 2.050 1,3-DMA (1) + Decalin (2) 1.741 1.457 1.802 1.505 1.860 1.547 1.917 1.592 1.980 1.641 2.046 1.697 2.125 1.759 2.206 1.825 2.298 1.902 2.385 1.974 2.475 2.050 1,3-DMA (1) + JP-10 (2) 2.125 1.762 2.158 1.796 2.207 1.839 2.257 1.879 2.307 1.920 2.353 1.955 2.394 1.989 2.421 2.012 2.451 2.033 2.458 2.046 2.475 2.050

333.15 K

343.15 K

353.15 K

363.15 K

0.563 0.603 0.650 0.708 0.776 0.853 0.957 1.072 1.223 1.432 1.734

0.511 0.546 0.586 0.635 0.692 0.757 0.845 0.940 1.066 1.237 1.485

0.469 0.498 0.533 0.575 0.623 0.679 0.753 0.833 0.938 1.084 1.288

0.433 0.459 0.489 0.525 0.566 0.614 0.678 0.745 0.834 0.956 1.127

0.741 0.790 0.831 0.884 0.952 1.026 1.115 1.218 1.356 1.509 1.734

0.663 0.704 0.744 0.783 0.840 0.903 0.978 1.062 1.176 1.302 1.485

0.601 0.637 0.669 0.701 0.751 0.803 0.867 0.937 1.034 1.138 1.288

0.547 0.578 0.606 0.634 0.677 0.721 0.774 0.835 0.915 1.006 1.127

1.260 1.298 1.331 1.366 1.405 1.447 1.498 1.550 1.611 1.670 1.734

1.102 1.133 1.160 1.190 1.220 1.254 1.294 1.335 1.385 1.431 1.485

0.973 0.998 1.021 1.045 1.070 1.096 1.129 1.163 1.203 1.242 1.288

0.866 0.889 0.908 0.928 0.948 0.968 0.995 1.025 1.058 1.091 1.127

1.514 1.544 1.577 1.609 1.638 1.666 1.694 1.712 1.726 1.731 1.734

1.318 1.342 1.366 1.391 1.413 1.438 1.457 1.472 1.480 1.482 1.485

1.159 1.175 1.197 1.219 1.237 1.254 1.269 1.280 1.287 1.290 1.288

1.029 1.042 1.059 1.075 1.087 1.104 1.115 1.120 1.126 1.129 1.127

x1 is the mole fraction of 1,3-DMA in the binary mixtures. Standard uncertainties u are u(T) = 0.01 K, u(x) = 0.0001, u(η) = 0.004 mPa.

where ηm is the viscosity of the binary mixture, and η1 and η2 are the viscosities of pure components. x1 and x2 are the mole fractions of pure components, and M1 and M2 are the molecular weights. The interaction parameters η12 and η21 are determined by the least-squares method, and are reported in Table S3 of the Supporting Information, together with the standard deviation (σ).

ln ηm = x13 ln η1 + 3x12x 2 ln η12 + 3x1x 22 ln η21 + x 23 ln η2 ⎡⎛ ⎛ M ⎞ M ⎞ ⎤ − ln⎜x1 + x 2 2 ⎟ + 3x12x 2 ln⎢⎜2 + 2 ⎟ /3⎥ ⎢⎣⎝ M1 ⎠ M1 ⎠ ⎥⎦ ⎝ ⎡⎛ ⎛M ⎞ M ⎞ ⎤ + 3x1x 22 ln⎢⎜1 + 2 2 ⎟ /3⎥ + x 23 ln⎜ 2 ⎟ ⎢⎣⎝ M1 ⎠ ⎦⎥ ⎝ M1 ⎠

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Figure 3. Viscosity deviations (Δη) as a function of mole fraction of 1,3-DMA (x1) for the binary systems (a, 1,3-DMA + n-decane; b, 1,3-DMA + butylcyclohexane; c, 1,3-DMA + decalin; d, 1,3-DMA + JP-10) at different temperatures (T): ■, 293.15 K; ●, 298.15 K; ▲, 303.15 K; ▼, 313.15; ◆, 323.15 K; left pointing triangle, 333.15 K right pointing triangle, 343.15 K; ⬢, 353.15K; ★, 363.15 K.

Figure 4. Surface tension (γ) as a function of mole fraction of 1,3-DMA (x1) at temperature T = 313.15 K: ■, 1,3-DMA + n-decane; ●, 1,3-DMA + butylcyclohexane; ▲, 1,3-DMA + decalin; ▼, 1,3-DMA + JP-10.

Figure 5. Surface tension deviations (Δγ) as a function of mole fraction of 1,3-DMA (x1) at temperature T = 313.15 K for the binary systems: ■, 1,3-DMA + n-decane; ●, 1,3-DMA + butylcyclohexane; ▲, 1,3-DMA + decalin; ▼, 1,3-DMA + JP-10.

Similar to the excess molar volumes, the viscosity deviations (Δη) are calculated from the following equation: Δη = ηm − (x1η1 + x 2η2)

where ηm, η1, and η2 are the viscosities of the mixture and two pure components, respectively. The values of Δη are listed

(6) 780

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The Δη values of the binary systems at each temperature are visually shown in Figure 3. It is indicated that the Δη values for the systems except 1,3-DMA + JP-10 are negative, and the absolute values decrease obviously with rising temperature. The addition of 1,3-DMA decreases relatively the viscous resistance with reference to the corresponding linear addition for the systems of 1,3-DMA + n-decane/butylcyclohexane/ decalin. The positive values of the Δη values for the systems of 1,3-DMA + JP-10 might be attributed to similar molecular structure of two components. The strained cyclic structures cause steric hindrance, and the internal friction forces among molecules of the binary systems increase when the liquid mixture flows. With the rise of temperature, the decreasing molecular attraction leads to the decrease of the viscous resistance for binary mixtures, and then the Δη value becomes smaller for each binary mixture with a certain mole fraction. 3.3. Surface Tension. Surface tension (γ) data corresponding to the binary systems of 1,3-DMA + n-decane/butylcyclohexane/ decalin/JP-10 are determined at temperature T = 313.15 K and atmospheric pressure p = 0.1 MPa. As shown in Figure 4, the values of pure components are in the order γ (n-decane) < γ (butylcyclohexane) < γ (1,3-DMA) < γ (decalin) < γ (JP-10). A decrease in surface tension is observed when the systems of 1,3DMA + decalin/JP-10 are enriched in 1,3-DMA, while the systems of 1,3-DMA + n-decane/butylcyclohexane follow an opposite trend. These results are useful for the composition adjustment of hydrocarbon fuels with appropriate dispersion. Similar to the viscosity deviations, the surface tension deviations (Δγ) are calculated from the following equation:

Table 5. Refractive Indices (nD) for the Binary Systems of 1,3DMA (1) + C10 Alkane (2) with Different Mole Fraction (x1) at Temperatures T = (293.15 to 313.15) K and Atmospheric Pressure p = 0.1 MPaa nD x1 0.0000 0.1028 0.1981 0.3019 0.3998 0.4996 0.6018 0.6968 0.7904 0.8950 1.0000 0.0000 0.0830 0.1716 0.2652 0.3625 0.4617 0.5636 0.6620 0.7728 0.8838 1.0000 0.0000 0.1034 0.2043 0.3050 0.4034 0.5024 0.6048 0.7046 0.8094 0.9013 1.0000 0.0000 0.1021 0.2015 0.3018 0.4005 0.4981 0.6020 0.6998 0.8051 0.8993 1.0000

293.15 K

298.15 K

303.15 K

1,3-DMA (1) + n-Decane (2) 1.4115 1.4095 1.4067 1.4182 1.4161 1.4133 1.4245 1.4224 1.4196 1.4313 1.4292 1.4265 1.4378 1.4358 1.4332 1.4445 1.4425 1.4402 1.4514 1.4494 1.4472 1.4579 1.4558 1.4537 1.4641 1.4621 1.4601 1.4710 1.4690 1.4671 1.4779 1.4759 1.4740 1,3-DMA (1) + Butylcyclohexane (2) 1.4398 1.4381 1.4351 1.4436 1.4417 1.4387 1.4473 1.4454 1.4424 1.4511 1.4492 1.4463 1.4548 1.4530 1.4502 1.4585 1.4567 1.4541 1.4623 1.4605 1.4580 1.4659 1.4641 1.4617 1.4699 1.4681 1.4658 1.4739 1.4720 1.4699 1.4779 1.4759 1.4740 1,3-DMA (1) + Decalin (2) 1.4731 1.4711 1.4685 1.4741 1.4720 1.4694 1.4748 1.4728 1.4703 1.4754 1.4735 1.4710 1.4760 1.4741 1.4717 1.4765 1.4746 1.4723 1.4769 1.4750 1.4728 1.4773 1.4754 1.4732 1.4776 1.4756 1.4736 1.4778 1.4758 1.4738 1.4779 1.4759 1.4740 1,3-DMA (1) + JP-10 (2) 1.4878 1.4855 1.4829 1.4870 1.4852 1.4825 1.4862 1.4844 1.4819 1.4854 1.4836 1.4812 1.4845 1.4827 1.4804 1.4836 1.4818 1.4795 1.4826 1.4807 1.4785 1.4816 1.4797 1.4774 1.4803 1.4785 1.4762 1.4792 1.4773 1.4751 1.4779 1.4759 1.4740

313.15 K 1.4023 1.4092 1.4156 1.4225 1.4290 1.4358 1.4428 1.4494 1.4559 1.4629 1.4699 1.4312 1.4347 1.4384 1.4423 1.4462 1.4501 1.4540 1.4577 1.4618 1.4658 1.4699

Δγ = γm − (x1γ1 + x 2γ2)

(7)

where γm, γ1, and γ2 are the surface tensions of the mixture, 1,3DMA, and a C10 alkane, respectively. The calculated values of Δγ for the four systems are shown in Figure 5. The values of Δγ can also be fitted to the Redlich−Kister correlation with eq 3. The correlated results of polynomial coefficients Ai with the standard deviations (σ) are listed in Table S6 of the Supporting Information. It can be observed that the Δγ values for the system of 1,3DMA + n-decane are obviously negative and those for other systems show small values near zero. The surface tension is related to the extent of intermolecular interaction after and before the mixture process. The γ of the liquid mixture is not a simple function of that of the pure components because, in a mixture, the composition of the surface is not the same as that of the bulk. In a typical situation, only the bulk composition can be known in mixtures. The surface tension of a mixture usually increases as the concentration of the component with the larger γ increases. The component with the lower γ concentrates in the surface phase of organic systems, so the Δγ value of the mixture tends to be negative.27 While the γ values of two components for the binary systems of 1,3-DMA + butylcyclohexane/decalin/JP10 are close, the Δγ values tend to be zero. 3.4. Refractive Index. The experimental values of refractive indices (nD) for the four systems at temperatures T = (293.15 to 313.15) K and atmospheric pressure p = 0.1 MPa are presented in Table 5. The values of refractive indices become smaller with the rise of temperature. The data of refractive indices become bigger with increasing mole fraction of 1,3-DMA in the binary systems of 1,3-DMA + n-decane/butylcyclohexane/decalin, and those follow an opposite trend for the system of 1,3-DMA + JP-10.27 The refractive index should also reflect the intermolecular interactions in the bulk after and before the mixture process to a

1.4645 1.4653 1.4661 1.4669 1.4676 1.4682 1.4687 1.4691 1.4694 1.4697 1.4699 1.4789 1.4782 1.4777 1.4770 1.4763 1.4756 1.4747 1.4737 1.4724 1.4713 1.4699

a

x1 is the mole fraction of 1,3-DMA in the binary mixtures. Standard uncertainties u are u(x) = 0.0001, u(T) = 0.01 K, and u(nD) = 0.0005.

in Table S4 of the Supporting Information, which can also be fitted to the Redlich−Kister correlation with eq 3. The correlated results of polynomial coefficients Ai with the standard deviations (σ) are listed in Table S5 of the Supporting Information. 781

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Figure 6. Refractive index deviations (ΔnD) as a function of mole fraction of 1,3-DMA (x1) for the binary systems (a, 1,3-DMA + n-decane; b, 1,3-DMA + butylcyclohexane; c, 1,3-DMA + decalin; d, 1,3-DMA + JP-10) at different temperatures (T): ■, 293.15 K; ●, 298.15 K; ▲, 303.15 K; ▼, 313.15 K.

The VmE values for the system of 1,3-DMA + JP-10 are smaller than those for the system of 1,3-DMA + butylcyclohexane. The differences of VmE could be mainly ascribed to the variations of structural effects. The addition of 1,3-DMA decreases the viscous resistance for the systems of 1,3-DMA + n-decane/butylcyclohexane/decalin with reference to the corresponding linear addition. The values of surface tension for pure components compare as γ (n-decane) < γ (butylcyclohexane) < γ (1,3-DMA) < γ (decalin) < γ (JP-10). The surface tension deviation (Δγ) gives clearly negative values for the system of 1,3-DMA + n-decane and shows small values near zero for the other systems. The data of refractive indices become bigger with the addition of 1,3-DMA for the systems of 1,3-DMA + n-decane/ butylcyclohexane/decalin, and those follow an opposite trend for the systems of 1,3-DMA + JP-10. Negligible values of ΔnD are observed, which indicates that the refractive indices show nearly linear additions from those of two components for the binary mixtures. Negative excess molar volumes along with negative viscosity deviations are always desirable for the enhancements of energy-density and transfer performance. Therefore, the results could provide important reference information for the preparation and optimization of new high energy-density hydrocarbon fuels.

certain extent. The refractive index deviations (ΔnD) are calculated from the following equation:28 ΔnD = nDm − (ϕ1nD1 + ϕ2nD2)

(8)

where ϕ1 and ϕ2 are volume fractions. nDm, nD1, and nD2 are the refractive indices of the mixture, 1,3-DMA, and a C10 alkane, respectively. All of the refractive index deviations are shown in Figure 6. The small values of ΔnD show only slight deviations of the refractive indices of mixtures from the corresponding linear addition values of two components. No further correlations of ΔnD with the Redlich−Kister type equation are considered.

4. CONCLUSIONS Fundamental property data of the density, viscosity, surface tension, and refractive index for the binary systems of 1,3-dimethyladamantane (1,3-DMA) + n-decane, butylcyclohexane, decalin, or exotetrahydrodicyclopentadiene (JP-10) at different temperatures and atmospheric pressure have been reported. The excess molar volumes (VmE), the viscosity deviations (Δη), the surface tension deviation (Δγ), and the refractive index deviation (ΔnD) of the four systems are calculated. The VmE values of all of the binary mixtures are negative. The VmE values for the system of 1,3-DMA + n-decane are more negative than those of other systems at the same composition and temperature. The VmE values of the systems of 1,3-DMA + ndecane/butylcyclohexane/decalin become less negative with the increase of ring number at the same composition and temperature.

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ASSOCIATED CONTENT

S Supporting Information *

Values of excess molar volumes (VmE), viscosity deviations (Δη), correlation coefficients (Ai) of the Redlich−Kister equation for 782

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VmE, Δη and Δγ, and interaction parameters (η12 and η21) in the double-parameter McAllister equation; GC−MS and 1H NMR spectra for the 1,3-DMA sample; figures for viscosities (η) versus compositions. This material is available free of charge via the Internet at http://pubs.acs.org.

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]; [email protected]. Tel: +86 571 88981416. Fax: +86 571 88981416. Funding

This work was financially supported by the National Natural Science Foundation of China under Grant Nos. 20973154, 21273201, and 21173191. Notes

The authors declare no competing financial interest.

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