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Densities and Viscosities for the Ternary System of exo-Tetrahydrodicyclopentadiene (1) + Methylcyclohexane (2) + Cyclopropanemethanol (3) and Its Binaries at T = 293.15 to 333.15 K Shenda Jin, Xi Wu, Yitong Dai, Yongsheng Guo, and Wenjun Fang* Department of Chemistry, Zhejiang University, Hangzhou 310027, China

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ABSTRACT: Measurements on densities (ρ) and viscosities (η) at nine temperatures from 293.15 to 333.15 K and the pressure p = 0.1 MPa for the ternary system of exo-tetrahydrodicyclopentadiene (1) + methylcyclohexane (2) + cyclopropanemethanol (3) and the corresponding binary systems have been carried out over the whole composition range. The excess molar volumes (VEm) and viscosity deviations (Δη) of the ternary system have been calculated and fitted to the Nagata−Tamura equation, while those of the binary systems have been calculated and fitted to the Redlich−Kister equation. The excess properties and deviation phenomena were discussed from the viewpoints of molecular interactions and structural effects. These fundamental results can be used to learn the nature of mixed hydrocarbon fuels.

1. INTRODUCTION Research on hybrid fuels plays an important role in the field of aviation fuel development. Besides the traditional chemical methods, to prepare an appropriate mixture from different hydrocarbon components is an effective means to improve fuel performance such as energy-density and heat sink enhancements. Naphthene is one important kind of fuel components, and methylcyclohexane (1-methyl cyclohexane) is the simplest single substituted naphthenic compound. The dehydrogenation of naphthenes can satisfy the cooling requirements of hypersonic aircrafts.1−3 Recently, high energy-density jet fuels have attracted much attention, and they are used in aviation fuel field to gain high volume heat value. The effective improvement of heat of combustion of the fuel can meet the demands of high speed and long running of aircrafts. exo-Tetrahydrodicyclopentadiene (2,3,5-trimethylidenebicyclo[2.2.1]heptane), also called JP-10, is a typical high energy-density jet fuel for new type aircrafts with high Mach numbers.4−12 It has 14.2% heat of combustion higher than JP-8 which is a petroleum-based fuel.13 JP-10 was first used by the United States as the fuel for turbojet engines. After JP-4 was replaced by JP-10, the missile range was increased about 15%. However, the long ignition delay time and the low combustion efficiency of high density fuels usually restrict their serious application.14 To overcome the defects, the addition of fuel additives has become an indispensable tool. Among various additives, alcohols are considered to be good candidates because they can improve the combustion characteristic and also reduce air pollution.15,16 Compared to common alcohol additives such as methanol, ethanol, and butanol, cyclopropanemethanol (1-cyclopropyl carbinol) has higher density and higher strain energy resulting from its ring structure. © XXXX American Chemical Society

It can probably promote the fuel combustion without reducing the energy per unit volume fuel and it becomes an ideal additive. Research on physical properties of the system composed of JP-10, cycloalkane and ring alcohol can provide significant references for the understanding of jet fuel additives and the development of new high energy-density fuels. In the present work, the densities and viscosities of the ternary mixtures, exo-tetrahydrodicyclopentadiene + methylcyclohexane + cyclopropanemethanol, and the corresponding three binary mixtures, exo-tetrahydrodicyclopentadiene + methylcyclohexane, exo-tetrahydrodicyclopentadiene + cyclopropanemethanol and methylcyclohexane + cyclopropanemethanol, are measured at nine temperatures from 293.15 to 333.15 K. The excess molar volumes (VEm) and viscosity deviations (Δη) of these systems are then calculated. Such fundamental data are provided for the fuel design and preparation.

2. EXPERIMENTAL SECTION 2.1. Materials. The samples of cyclopropanemethanol (CAS no. 2516-33-8) and methylcyclohexane (CAS no. 108-87-2) were purchased from Maclin Industrial Corporation. The sample of exo-tetrahydrodicyclopentadiene (CAS no. 2825-82-3) was provided by Tianjin University. The samples were degassed via an ultrasonic degassing method and dried by silica gel, and the mass fraction purity of these reagents were checked by GC−MS (7890A/5975C, Agilent). Detailed information is given in Table 1. Received: May 17, 2018 Accepted: August 1, 2018

A

DOI: 10.1021/acs.jced.8b00409 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 1. Specification of Chemicals in This Work compound

source

CAS number

provided mass fraction purity

measured mass fraction purity

analysis method

exo-tetrahydrodicyclopentadiene methylcyclohexane cyclopropanemethanol

Tianjin University Maclin Maclin

2825-82-3 108-87-2 2516-33-8

≥0.98 ≥0.99 ≥0.995

0.981 0.996 0.997

GC−MS GC−MS GC−MS

N

2.2. Methods. A Mettler Toledo AL204 balance, with an uncertainty of 0.0001 g, was used to prepare the binary and ternary mixtures. A series of glass bottles, with good sealing performance, were used to hold these mixtures. The uncertainty of the mole fractions was 0.0001. Densities of the samples were measured by an Anton Paar DMA 5000M, calibrated with double distilled water and dry air, at the temperature range from 293.15 to 333.15 K and the pressure p = 0.1 MPa. The relative uncertainty of density is 0.002. The uncertainty of temperature control is 0.01 K. Viscosities of pure reagents and various mixtures were measured by an automatic microviscometer (Anton Paar, model AMVn), calibrated with double distilled water, at nine temperatures from 293.15 to 333.15 K and the pressure p = 0.1 MPa. The precision of temperatures is controlled to be 0.01 K. The experimental datum obtained directly is the ball fall down time, the uncertainty of which is 0.001 s. Viscosities are calculated from the following equation, η = k(ρball − ρ)t

Δη = η −

The calculated values are listed in Tables S3 and S4. For the corresponding binary systems, the excess molar volumes (VEm) and viscosity deviations (Δη) are fitted to the Redlich−Kister equation, k

Y = x(1 − x) ∑ Ai (2x − 1)i − 1

where Y represents the calculated excess molar volume or viscosity deviation of the binary mixtures. x represents the mole fraction, Ai is the polynomial coefficients obtained by the leastsquares correlation and F-test. The values of Ai for the excess molar volumes (VEm) and viscosity deviations (Δη) of the corresponding binary systems are listed in Table S5. The standard deviation (σ) is calculated by eq 6, ÄÅ É ÅÅ ∑ (Y − Y )2 ÑÑÑ1/2 cal Ñ Å Å ÑÑ σ = ÅÅ ÅÅÅ (n − k) ÑÑÑÑ (6) Ç Ö where n is the number of experimental datum points and k is the number of fitted parameters. For the ternary system, the excess molar volumes (VEm) and the viscosity deviations (Δη) are fitted to eq 7,

(1)

Y123 = Y12 + Y23 + Y13 + Δ123

where Δ123 can usually be fitted with different models: Cibulka model: Δ123 = x1x 2x3(A + Bx1 + Cx 2)

(8)

Redlich−Kister model: (2)

Δ123 = x1x 2x3[A + B(x1 − x 2) + C(x 2 − x3)

where Llit is the literature value and L is the measured value. The densities and viscosities for the corresponding binary systems at nine temperatures from 293.15 to 333.15 K and the pressure p = 0.1 MPa are presented in Tables 3 and 4. Those for the ternary system at the same temperatures and pressure are given in Tables 5 and 6. The excess molar volumes (VEm) of the corresponding binary systems and the ternary system at different temperatures are calculated with eq 3,

+ D(x3 − x1) + E(x1 − x 2)2 + F(x 2 − x3)2 + G(x3 − x1)2 + ...]

(9)

Singh model: Δ123 = x1x 2x3[A + Bx1(x 2 − x3) + Cx12(x3 − x 2)]

(10)

Nagata−Tamura model: Δ123 = x1x 2x3RT (B0 − B1x1 − B2 x 2 − B3x12 − B4 x 22

N i=1

(7) 17

n

∑ xiMi[(1/ρ) − (1/ρi )]

(5)

i=1

3. RESULTS AND DISCUSSION The measured densities and viscosities of pure substances are listed in Table 2, together with the reference values. The absolute average relative deviation (AARD) is calculated from the following equation,

VmE =

(4)

i=1

where k is a constant of the viscometer (here, k = 0.010256), ρball is the density of the ball (here, ρball = 7.68 kg·m−3), ρ is the density of a sample, and t is the ball fall down time. The relative uncertainty ur of viscosity is evaluated to be 0.01.

|L − L | i1y AARD = jjj zzz ∑ lit k n { i = 1 |L lit|

∑ xiηi

− B5x1x 2 − B6 x13 − B7 x 23 − B8x12x 2)

(3)

(11)

For the four different equations, the values of the adjustable parameters for the excess molar volumes (VEm) and viscosity deviations (Δη) of the ternary system are listed in Table S6 − S9, along with the standard deviation (σ). 3.1. Binary Systems. The changes of excess volumes with composition of binary systems are shown in Figure 1. The excess molar volumes (VEm) for the systems of exo-tetrahydrodicyclopentadiene (1) + cyclopropanemethanol (2) and methylcyclohexane (1) + cyclopropanemethanol (2) at different temperatures

where i stands for a pure component, xi and Mi are the mole fraction and the molar mass of component i in a mixture, respectively, and N represents the number of components in a mixture. The calculated results are listed in Tables S1 and S2. Equation 4 was used to calculate the viscosity deviations (Δη) of the corresponding binary systems and the ternary system at given temperatures, B

DOI: 10.1021/acs.jced.8b00409 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 2. Comparison of Experimental Densities (ρ) and Viscosities (η) for Pure Compounds with Literature Data at Corresponding Temperatures and p = 0.1 MPaa property ρ/g·cm−3

η/mPa·s

ρ/g·cm−3

η/mPa·s

ρ/g·cm−3

η/mPa·s

T/K

this study

293.15 298.15 303.15 308.15 313.15 318.15 323.15 328.15 333.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15 328.15 333.15

0.93559 0.93169 0.92777 0.92386 0.91995 0.91606 0.91211 0.90821 0.90421 3.066 2.781 2.532 2.311 2.118 1.946 1.794 1.658 1.537

293.15 298.15 303.15 308.15 313.15 318.15 323.15 328.15 333.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15 328.15 333.15

0.76936 0.76502 0.76071 0.75634 0.75202 0.74761 0.74320 0.73877 0.73432 0.726 0.682 0.641 0.604 0.571 0.541 0.514 0.490 0.468

293.15 298.15 303.15 308.15 313.15 318.15 323.15 328.15 333.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15 328.15 333.15

0.91303 0.90899 0.90491 0.90081 0.89665 0.89243 0.88821 0.88389 0.87961 3.979 3.441 2.991 2.617 2.302 2.037 1.810 1.615 1.446

literature exo-Tetrahydrodicyclopentadiene 0.93557726 0.93166426 0.92775026 0.92383726 0.91992326 0.91600226 0.91207226 0.90813426 0.90418826 3.058226 2.767326 2.515326 2.292726 2.103426 1.934326 1.784826 1.651526 1.532126 Methylcyclohexane 0.76933 ± 0.00127 0.76500 ± 0.00127 0.76067 ± 0.00127 0.75632 ± 0.00127 0.75195 ± 0.00127 0.74756 ± 0.00127 0.74315 ± 0.00127 0.73873 ± 0.00127 0.73428 ± 0.00127 0.727 ± 0.0127 0.681 ± 0.0127 0.640 ± 0.0127 0.604 ± 0.0127 0.571 ± 0.0127 0.542 ± 0.0127 0.515 ± 0.0127 0.491 ± 0.0127 0.469 ± 0.0127 Cyclopropanemethanol 0.91299 ± 0.000517 0.90894 ± 0.000517 0.90485 ± 0.000517 0.90074 ± 0.000517 0.89658 ± 0.000517 0.89238 ± 0.000517 0.88813 ± 0.000517 0.88384 ± 0.000517 0.87949 ± 0.000517 4.029 ± 0.0117 3.485 ± 0.0117 3.037 ± 0.0117 2.661 ± 0.0117 2.344 ± 0.0117 2.074 ± 0.0117 1.843 ± 0.0117 1.646 ± 0.0117 1.476 ± 0.0117

AARD% 0.93557326 0.93165926 0.92774426 0.92383326 0.91991826 0.91599926 0.91206826 0.90812926 0.90418626 3.075226 2.782326 2.528726 2.308026 2.114726 1.944926 1.794826 1.661226 1.541926

0.002 0.003 0.002 0.002 0.003 0.006 0.005 0.008 0.003 0.277 0.271 0.390 0.458 0.448 0.321 0.280 0.293 0.319

0.76935 ± 0.0000528 0.76505 ± 0.0000528 0.76071 ± 0.0000528 0.75637 ± 0.0000528 0.75200 ± 0.0000528 0.74758 ± 0.0000528 0.74317 ± 0.0000528

0.003 0.003 0.003 0.003 0.005 0.005 0.005 0.005 0.005 0.681 0.795 0.846 0.894 0.775 0.820 0.863 0.203 0.946

0.73429 ± 0.0000528 0.735 ± 0.0828 0.692 ± 0.0828 0.651 ± 0.0828 0.615 ± 0.0828 0.580 ± 0.0828 0.549 ± 0.0828 0.522 ± 0.0828 0.476 ± 0.0828

0.004 0.006 0.007 0.008 0.008 0.006 0.009 0.006 0.014 1.240 1.267 1.511 1.661 1.792 1.776 1.778 1.866 2.001

a

Standard uncertainties u are u(p) = 0.20 kPa, u(T) = 0.01 K, ur(ρ) = 0.002, ur (η) = 0.01. C

DOI: 10.1021/acs.jced.8b00409 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 3. Measured Densities (ρ) at Different Mole Fractions (x1) for the Binary Mixtures of exo-Tetrahydrodicyclopentadiene (1) + Methylcyclohexane (2); exo-Tetrahydrodicyclopentadiene (1) + Cyclopropanemethanol (2); Methylcyclohexane (1) + Cyclopropanemethanol (2) at T = 293.15 to 333.15 K and p = 0.1 MPaa ρ/g·cm−3 x1

293.15 K

298.15 K

0.0000 0.0988 0.1982 0.3031 0.4021 0.5035 0.6010 0.6993 0.7980 0.9013 1.0000

0.76936 0.78871 0.80743 0.82664 0.84394 0.86082 0.87650 0.89193 0.90679 0.92195 0.93559

0.76502 0.78443 0.80319 0.82244 0.83980 0.85672 0.87244 0.88791 0.90281 0.91801 0.93169

0.0000 0.1007 0.2016 0.3013 0.3963 0.4982 0.6033 0.7020 0.7961 0.8991 1.0000

0.91303 0.91521 0.91767 0.92015 0.92239 0.92462 0.92693 0.92894 0.93087 0.93302 0.93559

0.90899 0.91113 0.91356 0.91603 0.91827 0.92050 0.92281 0.92485 0.92682 0.92901 0.93169

0.0000 0.0987 0.2002 0.2987 0.3990 0.5038 0.5940 0.6905 0.7967 0.8972 1.0000

0.91303 0.89109 0.87098 0.85335 0.83746 0.82248 0.81079 0.79929 0.78782 0.77796 0.76936

0.90899 0.88697 0.86681 0.84911 0.83316 0.81813 0.80641 0.79488 0.78341 0.77356 0.76502

303.15 K

308.15 K

313.15 K

318.15 K

exo-Tetrahydrodicyclopentadiene (1) + Methylcyclohexane (2) 0.76071 0.75634 0.75202 0.74761 0.78017 0.77585 0.77158 0.76723 0.79897 0.79471 0.79048 0.78628 0.81826 0.81405 0.80987 0.80564 0.83567 0.83150 0.82737 0.82318 0.85262 0.84850 0.84441 0.84028 0.86839 0.86431 0.86026 0.85619 0.88389 0.87986 0.87585 0.87182 0.89883 0.89483 0.89086 0.88687 0.91406 0.91010 0.90616 0.90223 0.92777 0.92386 0.91995 0.91606 exo-Tetrahydrodicyclopentadiene (1) + Cyclopropanemethanol (2) 0.90491 0.90081 0.89665 0.89243 0.90702 0.90288 0.89869 0.89444 0.90942 0.90525 0.90104 0.89677 0.91187 0.90768 0.90346 0.89919 0.91410 0.90992 0.90570 0.90144 0.91633 0.91216 0.90795 0.90371 0.91867 0.91451 0.91032 0.90611 0.92074 0.91660 0.91246 0.90829 0.92274 0.91864 0.91454 0.91043 0.92499 0.92094 0.91690 0.91285 0.92777 0.92386 0.91995 0.91606 Methylcyclohexane (1) + Cyclopropanemethanol (2) 0.90491 0.90081 0.89665 0.89243 0.88283 0.87865 0.87442 0.87013 0.86260 0.85836 0.85407 0.84970 0.84485 0.84053 0.83619 0.83176 0.82884 0.82447 0.82008 0.81560 0.81377 0.80935 0.80492 0.80041 0.80203 0.79758 0.79313 0.78858 0.79048 0.78601 0.78154 0.77698 0.77900 0.77453 0.77007 0.76551 0.76916 0.76470 0.76025 0.75572 0.76071 0.75634 0.75202 0.74761

323.15 K

328.15 K

333.15 K

0.74320 0.76287 0.78189 0.80139 0.81899 0.83613 0.85207 0.86775 0.88285 0.89824 0.91211

0.73877 0.75851 0.77758 0.79714 0.81480 0.83199 0.84798 0.86371 0.87886 0.89429 0.90821

0.73432 0.75412 0.77325 0.79287 0.81056 0.82781 0.84384 0.85961 0.87479 0.89027 0.90421

0.88821 0.89018 0.89248 0.89487 0.89713 0.89942 0.90184 0.90407 0.90626 0.90876 0.91211

0.88389 0.88584 0.88812 0.89051 0.89279 0.89510 0.89757 0.89985 0.90209 0.90468 0.90821

0.87961 0.88150 0.88375 0.88612 0.88841 0.89073 0.89323 0.89555 0.89784 0.90052 0.90421

0.88821 0.86582 0.84532 0.82735 0.81109 0.79590 0.78404 0.77240 0.76093 0.75117 0.74320

0.88389 0.86143 0.84086 0.82279 0.80652 0.79142 0.77949 0.76778 0.75632 0.74659 0.73877

0.87961 0.85706 0.83641 0.81827 0.80196 0.78681 0.77491 0.76317 0.75169 0.74199 0.73432

a

Standard uncertainties u are u(p) = 0.20 kPa, uc(x) = 0.0002, u(T) = 0.01 K, ur(ρ) = 0.002.

Table 4. Measured Viscosities (η) at Different Mole Fractions (x1) for the Binary Mixtures of exo-Tetrahydrodicyclopentadiene (1) + Methylcyclohexane (2); exo-Tetrahydrodicyclopentadiene (1) + Cyclopropanemethanol (2); Methylcyclohexane (1) + Cyclopropanemethanol (2) at T = 293.15 to 333.15 K and p = 0.1 MPaa η/mPa·s x1

293.15 K

298.15 K

0.0000 0.0988 0.1982 0.3031 0.4021 0.5035 0.6010 0.6993 0.7980 0.9013 1.0000

0.726 0.826 0.951 1.088 1.247 1.447 1.659 1.928 2.190 2.565 3.065

0.682 0.773 0.886 1.010 1.155 1.336 1.530 1.752 2.000 2.334 2.781

0.0000 0.1007

3.979 3.671

3.441 3.193

303.15 K

308.15 K

313.15 K

318.15 K

exo-Tetrahydrodicyclopentadiene (1) + Methylcyclohexane (2) 0.641 0.604 0.571 0.541 0.723 0.660 0.641 0.606 0.827 0.774 0.728 0.686 0.940 0.878 0.823 0.772 1.072 0.999 0.934 0.874 1.236 1.148 1.070 0.999 1.412 1.306 1.212 1.128 1.611 1.484 1.376 1.279 1.833 1.687 1.559 1.444 2.128 1.953 1.799 1.661 2.532 2.311 2.118 1.946 exo-Tetrahydrodicyclopentadiene (1) + Cyclopropanemethanol (2) 2.991 2.617 2.302 2.037 2.793 2.453 2.169 1.926 D

323.15 K

328.15 K

333.15 K

0.514 0.574 0.648 0.728 0.821 0.936 1.054 1.192 1.338 1.540 1.794

0.490 0.545 0.614 0.687 0.774 0.879 0.988 1.114 1.247 1.431 1.658

0.468 0.519 0.583 0.651 0.731 0.827 0.931 1.044 1.165 1.335 1.537

1.810 1.718

1.615 1.540

1.446 1.390

DOI: 10.1021/acs.jced.8b00409 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 4. continued η/mPa·s x1

293.15 K

298.15 K

0.2016 0.3013 0.3963 0.4982 0.6033 0.7020 0.7961 0.8991 1.0000

3.451 3.287 3.150 3.030 2.929 2.858 2.831 2.838 3.065

3.013 2.881 2.776 2.683 2.613 2.557 2.544 2.558 2.781

0.0000 0.0987 0.2002 0.2987 0.3990 0.5038 0.5940 0.6905 0.7967 0.8972 1.0000

3.979 3.068 2.420 1.949 1.686 1.407 1.133 0.955 0.839 0.764 0.726

3.441 2.681 2.135 1.732 1.506 1.221 1.017 0.879 0.779 0.713 0.682

303.15 K

308.15 K

313.15 K

318.15 K

exo-Tetrahydrodicyclopentadiene (1) + Cyclopropanemethanol (2) 2.646 2.334 2.071 1.847 2.541 2.256 2.012 1.802 2.457 2.194 1.964 1.767 2.387 2.134 1.919 1.733 2.339 2.105 1.901 1.726 2.298 2.076 1.883 1.716 2.298 2.085 1.899 1.736 2.318 2.111 1.929 1.769 2.532 2.311 2.118 1.946 Methylcyclohexane (1) + Cyclopropanemethanol (2) 2.991 2.617 2.302 2.037 2.354 2.083 1.848 1.645 1.889 1.682 1.505 1.351 1.547 1.388 1.251 1.133 1.351 1.219 1.104 1.004 1.113 1.029 0.930 0.850 0.930 0.855 0.789 0.731 0.812 0.753 0.701 0.655 0.725 0.677 0.634 0.596 0.667 0.626 0.589 0.556 0.641 0.604 0.571 0.541

323.15 K

328.15 K

333.15 K

1.655 1.617 1.593 1.572 1.572 1.572 1.588 1.624 1.794

1.489 1.461 1.444 1.431 1.438 1.443 1.463 1.499 1.658

1.345 1.325 1.315 1.309 1.319 1.324 1.349 1.388 1.537

1.810 1.474 1.220 1.028 0.917 0.786 0.680 0.613 0.562 0.526 0.514

1.615 1.325 1.105 0.938 0.842 0.733 0.635 0.576 0.531 0.499 0.490

1.446 1.197 1.005 0.859 0.775 0.683 0.595 0.542 0.504 0.477 0.468

a

Standard uncertainties u are u(p) = 0.20 kPa, uc(x) = 0.0002, u(T) = 0.01 K, ur(η) = 0.01.

Table 5. Measured Densities (ρ) at Different Mole Fractions (x1) for the ternary Mixtures of exo-Tetrahydrodicyclopentadiene (1) + Methylcyclohexane (2) + Cyclopropanemethanol (3) at T = 293.15 to 333.15 K and p = 0.1 MPaa ρ/g·cm−3 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

0.1011 0.1024 0.1999 0.0992 0.2003 0.2985 0.0997 0.1991 0.2993 0.3979 0.0998 0.1999 0.2975 0.3976 0.4997 0.1017 0.1993 0.2971 0.4004 0.4970 0.5974 0.1006 0.1983 0.3021 0.3958 0.4947 0.6036 0.7010 0.0991 0.2006 0.3012

0.0999 0.1987 0.1006 0.2982 0.1988 0.0989 0.3982 0.2984 0.2000 0.1014 0.5001 0.4002 0.3011 0.1983 0.0968 0.6002 0.4980 0.4005 0.2994 0.1988 0.0988 0.7016 0.6010 0.4995 0.4042 0.2986 0.1967 0.0997 0.8021 0.6965 0.6035

0.89504 0.87700 0.89877 0.86011 0.88205 0.90273 0.84549 0.86675 0.88665 0.90582 0.83165 0.85220 0.87198 0.89129 0.90982 0.81920 0.83950 0.85849 0.87747 0.89528 0.91252 0.80770 0.82729 0.84671 0.86398 0.88219 0.89969 0.91542 0.79740 0.81732 0.83510

0.89090 0.87280 0.89462 0.85609 0.87786 0.89857 0.84118 0.86250 0.88244 0.90166 0.82731 0.84792 0.86774 0.88708 0.90566 0.81485 0.83520 0.85422 0.87326 0.89112 0.90840 0.80334 0.82298 0.84244 0.85976 0.87801 0.89555 0.91133 0.79304 0.81301 0.83084

0.88672 0.86858 0.89043 0.85182 0.87363 0.89437 0.83686 0.85823 0.87820 0.89746 0.82299 0.84362 0.86348 0.88287 0.90147 0.81049 0.83089 0.84994 0.86902 0.88692 0.90424 0.79897 0.81866 0.83818 0.85553 0.87382 0.89139 0.90721 0.78869 0.80871 0.82658

0.88251 0.86430 0.88620 0.84750 0.86936 0.89015 0.83249 0.85391 0.87393 0.89324 0.81862 0.83927 0.85918 0.87862 0.89726 0.80608 0.82654 0.84562 0.86475 0.88270 0.90006 0.79455 0.81431 0.83386 0.85127 0.86959 0.88721 0.90307 0.78430 0.80434 0.82227

0.87826 0.86000 0.88194 0.84315 0.86505 0.88588 0.82811 0.84957 0.86964 0.88899 0.81416 0.83492 0.85487 0.87435 0.89303 0.80167 0.82216 0.84130 0.86048 0.87846 0.89588 0.79015 0.80993 0.82955 0.84699 0.86536 0.88303 0.89893 0.77989 0.80001 0.81798

0.87395 0.85563 0.87762 0.83873 0.86069 0.88156 0.82366 0.84517 0.86530 0.88469 0.80968 0.83050 0.85051 0.87003 0.88877 0.79717 0.81773 0.83693 0.85616 0.87420 0.89166 0.78566 0.80550 0.82517 0.84266 0.86109 0.87881 0.89476 0.77543 0.79560 0.81363

0.86961 0.85124 0.87327 0.83428 0.85629 0.87720 0.81919 0.84073 0.86091 0.88036 0.80516 0.82603 0.84609 0.86567 0.88446 0.79265 0.81326 0.83251 0.85179 0.86988 0.88738 0.78113 0.80103 0.82076 0.83830 0.85677 0.87456 0.89054 0.77093 0.79116 0.80925

0.86519 0.84677 0.86885 0.82974 0.85183 0.87281 0.81473 0.83625 0.85649 0.87598 0.80062 0.82154 0.84166 0.86122 0.88014 0.78810 0.80876 0.82807 0.84741 0.86555 0.88310 0.77659 0.79655 0.81634 0.83393 0.85245 0.87030 0.88633 0.76642 0.78671 0.80487

0.86078 0.84230 0.86443 0.82523 0.84735 0.86838 0.81032 0.83174 0.85203 0.87157 0.79604 0.81701 0.83718 0.85686 0.87576 0.78353 0.80423 0.82359 0.84298 0.86116 0.87876 0.77202 0.79203 0.81188 0.82951 0.84808 0.86597 0.88205 0.76189 0.78223 0.80045

E

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Table 5. continued ρ/g·cm−3 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

0.4012 0.4975 0.5992 0.6955 0.7973

0.4992 0.3986 0.2997 0.1980 0.1019

0.85358 0.87064 0.88696 0.90293 0.91791

0.84935 0.86647 0.88283 0.89885 0.91386

0.84513 0.86229 0.87869 0.89473 0.90979

0.84087 0.85807 0.87451 0.89061 0.90571

0.83662 0.85386 0.87035 0.88648 0.90162

0.83233 0.84962 0.86616 0.88233 0.89752

0.82800 0.84533 0.86192 0.87813 0.89337

0.82366 0.84105 0.85768 0.87395 0.88924

0.81928 0.83671 0.85340 0.86970 0.88503

a

Standard uncertainties u are u(p) = 0.20 kPa, uc(x) = 0.0002, u(T) = 0.01 K, ur(ρ) = 0.002.

Table 6. Measured Viscosities (η) for the ternary Mixture of exo-Tetrahydrodicyclopentadiene (1) + Methylcyclohexane (2) + Cyclopropanemethanol (3) at T = 293.15 to 333.15 K and p = 0.1 MPaa η/mPa·s 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

0.1011 0.1024 0.1999 0.0992 0.2003 0.2985 0.0997 0.1991 0.2993 0.3979 0.0998 0.1999 0.2975 0.3976 0.4997 0.1017 0.1993 0.2971 0.4004 0.4970 0.5974 0.1006 0.1983 0.3021 0.3958 0.4947 0.6036 0.7010 0.0991 0.2006 0.3012 0.4012 0.4975 0.5992 0.6955 0.7973

0.0999 0.1987 0.1006 0.2982 0.1988 0.0989 0.3982 0.2984 0.2000 0.1014 0.5001 0.4002 0.3011 0.1983 0.0968 0.6002 0.4980 0.4005 0.2994 0.1988 0.0988 0.7016 0.6010 0.4995 0.4042 0.2986 0.1967 0.0997 0.8021 0.6965 0.6035 0.4992 0.3986 0.2997 0.1980 0.1019

2.869 2.307 2.773 1.881 2.221 2.640 1.542 1.853 2.194 2.557 1.334 1.513 1.785 2.150 2.603 1.103 1.289 1.497 1.760 2.065 2.435 0.979 1.122 1.302 1.509 1.770 2.093 2.531 0.875 1.010 1.163 1.342 1.551 1.801 2.195 2.425

2.519 2.042 2.448 1.680 1.976 2.337 1.389 1.662 1.973 2.273 1.212 1.370 1.608 1.931 2.357 1.013 1.179 1.363 1.596 1.866 2.188 0.905 1.035 1.196 1.380 1.611 1.899 2.300 0.815 0.936 1.075 1.235 1.423 1.643 2.007 2.197

2.222 1.817 2.168 1.507 1.764 2.079 1.256 1.497 1.771 2.032 1.098 1.246 1.458 1.742 2.125 0.934 1.082 1.245 1.452 1.691 1.976 0.840 0.956 1.101 1.265 1.471 1.729 2.098 0.760 0.869 0.997 1.138 1.308 1.506 1.833 1.999

1.968 1.624 1.931 1.356 1.582 1.862 1.141 1.356 1.598 1.829 1.012 1.138 1.328 1.578 1.913 0.862 0.997 1.143 1.328 1.539 1.791 0.781 0.886 1.017 1.164 1.350 1.580 1.896 0.711 0.810 0.926 1.054 1.207 1.385 1.680 1.825

1.758 1.457 1.727 1.230 1.427 1.673 1.041 1.233 1.449 1.652 0.931 1.045 1.212 1.435 1.730 0.800 0.921 1.053 1.218 1.407 1.634 0.729 0.825 0.942 1.076 1.242 1.453 1.718 0.667 0.757 0.863 0.979 1.118 1.278 1.545 1.674

1.574 1.314 1.552 1.117 1.294 1.508 0.954 1.125 1.320 1.498 0.858 0.961 1.114 1.312 1.570 0.744 0.853 0.973 1.121 1.291 1.495 0.682 0.770 0.877 0.996 1.147 1.338 1.540 0.628 0.709 0.807 0.912 1.039 1.184 1.430 1.540

1.412 1.190 1.400 1.020 1.176 1.369 0.877 1.031 1.205 1.367 0.791 0.888 1.024 1.202 1.433 0.694 0.792 0.902 1.036 1.189 1.367 0.640 0.720 0.817 0.926 1.063 1.232 1.371 0.592 0.667 0.757 0.852 0.967 1.099 1.331 1.423

1.274 1.082 1.269 0.934 1.076 1.245 0.810 0.948 1.104 1.249 0.739 0.823 0.947 1.110 1.314 0.650 0.739 0.839 0.960 1.098 1.258 0.602 0.675 0.764 0.863 0.987 1.139 1.282 0.561 0.628 0.711 0.798 0.903 1.024 1.250 1.317

1.155 0.987 1.154 0.856 0.987 1.135 0.752 0.874 1.014 1.148 0.688 0.765 0.878 1.021 1.213 0.611 0.691 0.782 0.892 1.017 1.162 0.568 0.635 0.717 0.806 0.920 1.061 1.188 0.532 0.594 0.670 0.750 0.846 0.956 1.188 1.223

a

Standard uncertainties u are u(p) = 0.20 kPa, uc(x) = 0.0002, u(T) = 0.01 K, ur(η) = 0.01.

force, and dispersion force) and chemical force (hydrogen bonding). The chemical force is quite larger than the physical force, and it provides a great contribution to the excess molar volume. For the systems of exo-tetrahydrodicyclopentadiene (1) + cyclopropanemethanol (2) and methylcyclohexane (1) + cyclopropanemethanol (2), the hydrogen bonding between cyclopropanemethanol molecules is broken and the molecular interaction of the system decreases, which increases the volume of mixture. The maximum of the excess molar volumes for the

from 293.15 to 333.15 K are positive, and the maximum of the excess molar volume at each temperature is at the mole fraction x1 around 0.6. The excess molar volumes (VEm) for the binary system of exo-tetrahydrodicyclopentadiene (1) + methylcyclohexane (2) are negative. In the case of binary systems, the molecular structures and the interaction force between two components are the main factors influencing the excess molar volume. Molecular interaction forces in the investigated systems mainly include the physical forces (electrostatic force, induced F

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methylcyclohexane (1) + cyclopropanemethanol (2), are mainly due to hydrogen bonding among cyclopropanemethanol molecules. From DFT calculations via the Material Studio, the energy profiles for the interaction of two cyclopropanemethanol molecules is −18.28 kJ·mol−1. Two cyclopropanemethanol molecules are built with no interaction, and the geometry of the molecules is optimized with the pw91-GCA, and the total energy is calculated. Then, the two cyclopropanemethanol molecules are assembled within a certain distance to form a hydrogen bond. The structure is also optimized by pw91-GCA and the corresponding energy is calculated. The process of energy change is shown in Figure 2.17,19,20 When cyclopropanemethanol is mixed

Figure 2. Energy profiles (kJ·mol−1) for the interaction of cyclopropanemethanol molecules.

with exo-tetrahydrodicyclopentadiene or methylcyclohexane, the strongly self-associating structure formed by hydrogen bonding is broken, which leads to positive values of the excess molar volumes. However, the mixture of exo-tetrahydrodicyclopentadiene (1) + methylcyclohexane (2) is composed of nonpolar molecules, When the nonpolar molecules convergence, their instantaneous dipole moments will produce weak attraction. This kind of attraction is so-called dispersion force, which increases with the increase of molecular weight. exoTetrahydrodicyclopentadiene and methylcyclohexane are nonpolar molecules and the molecular weights are 136.24 and 98.19, respectively. The dispersion forces of exo-tetrahydrodicyclopentadiene and methylcyclohexane are not much different. When they are mixed, the change of dispersion is not large and cannot influence the values of Δη and VEm significantly. The dispersion force of JP-10 and methylcyclohexane is not much different. When they are mixed, the change of dispersion is not large and can not influence significantly the values of Δη and VEm significantly. As a result, When the change of molecular interaction is low, spatial factors such as molecular structure, size, and shape are relatively the main factors influencing the excess molar volumes. When the molecules with large size and threedimensional structure are mixed with those with small size and simple structure, the latter molecules can insert themselves into the former, and the molar volume of mixture decreases. Here, exo-tetrahydrodicyclopentadiene is a three-dimensional component with relatively large size, methylcyclohexane has boat and chair structures with a short alkyl, and cyclopropanemethanol has small size and simple structure. When exo-tetrahydrodicyclopentadiene is mixed with methylcyclohexane or cyclopropanemethanol, the latter molecules can insert themselves into exo-tetrahydrodicyclopentadiene molecules, and the molar volume of mixture decreases. For the system of exotetrahydrodicyclopentadiene (1) + methylcyclohexane (2), the values of excess molar volume are negative and the minimum value is about −0.51 cm3·mol−1. Considering the spatial factor, exo-tetrahydrodicyclopentadiene is a three-dimensional institution and methylcyclohexane has a boat or chair structure with a

Figure 1. Excess molar volumes, VEm, as a function of mole fraction of component 1 for the binary systems of (a) exo-tetrahydrodicyclopentadiene (1) + methylcyclohexane (2); (b) exo-tetrahydrodicyclopentadiene (1) + cyclopropanemethanol (2); (c) methylcyclohexane (1) + cyclopropanemethanol (2) at 0.1 MPa and 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; , the Redlich− Kister correlations.

above two systems are about 0.60 cm3·mol−1 and 0.38 cm3·mol−1, respectively.18 The phenomena for the mixtures of, exotetrahydrodicyclopentadiene (1) + cyclopropanemethanol (2) and G

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short alkyl, the latter molecules can inset themselves into exotetrahydrodicyclopentadiene molecules. From the micro point of view, the space between the molecules is reduced, and from the macro point of view, the volume of the binary system is reduced.21−23 Hence, the excess molar volumes (VEm) of the exotetrahydrodicyclopentadiene + methylcyclohexane are observed to be negative. From Figure 1, we also find that the absolute value of the excess molar volumes increases with the rise of temperature, because the hydrogen bonding is broken easily at a high temperature and the molecular motion becomes fierce with the rise of temperature.24 In addition, the corresponding value of excess molar volumes of exo-tetrahydrodicyclopentadiene + cyclopropanemethanol is larger than that of methylcyclohexane + cyclopropanemethanol. This occurs because the molecular weight of exo-tetrahydrodicyclopentadiene is larger than that of methylcyclohexane. The binary mixture of the former demonstrates a stronger dispersion force and has more positive excess molar volumes. The viscosity deviations (Δη) of binary systems are shown in Figure 3. It can be found that the values are negative in the whole composition range at different temperatures from 293.15 to 333.15 K. For the systems of exo-tetrahydrodicyclopentadiene (1) + methylcyclohexane (2) and exo-tetrahydrodicyclopentadiene (1) + cyclopropanemethanol (2), the absolute maximum values of the viscosity deviations are at the mole fraction of x1 around 0.6. When the alkane was added into cyclopropanemethanol, the self-association of cyclopropanemethanol molecules because of hydrogen bonding decreases and then the viscosity of the mixture decreases. For the mixture of exo-tetrahydrodicyclopentadiene (1) + methylcyclohexane (2), as a reason for the lower interaction between two components, a noticeable decrease in viscosities occurs. Furthermore, the absolute values of viscosity deviations (Δη) decrease with the temperature increasing, because the hydrogen bonding is weakness at a high temperature and the dispersion force becomes stronger with the rise of temperature. The density of the binary system mixutre of exo-tetrahydrodicyclopentadiene with n-nonane has been studied.25 The changes of excess volumes with composition of the binary system of exotetrahydrodicyclopentadiene + n-nonane are similar to the binary system of exo-tetrahydrodicyclopentadiene + methylcyclohexane. The excess molar volumes for the systems are all negative. n-Nonane and methylcyclohexane have a small size and simple structure, when they mix with exo-tetrahydrodicyclopentadiene, the former molecules can insert themselves into exo-tetrahydrodicyclopentadiene molecules, and the volume will be smaller. The density and viscosity of the ternary system of cyclopropanemethanol + n-dodecane + butylcyclohexane and corresponding binaries has been studied,17 changes of excess volumes and viscosity deviations with composition of the binary systems of cyclopropanemethanol + n-dodecane and cyclopropanemethanol + butylcyclohexane are similar to the binary systems of exo-tetrahydrodicyclopentadiene + cyclopropanemethanol and methylcyclohexane + cyclopropanemethanol, the excess molar volumes for the systems are all positive, and the viscosity deviations for the systems are all negative. When cyclopropanemethanol is mixed with exo-tetrahydrodicyclopentadiene, methylcyclohexane, n-dodecane, or butylcyclohexane, the strongly self-associating structure formed by hydrogen bonding is broken, which leads to positive values of the excess molar volumes and negative values of the viscosity deviations.

Figure 3. Viscosity deviations, Δη, as a function of mole fraction of component 1 for the binary systems of (a) exo-tetrahydrodicyclopentadiene (1) + methylcyclohexane (2); (b) exo-tetrahydrodicyclopentadiene (1) + cyclopropanemethanol (2); (c) methylcyclohexane (1) + cyclopropanemethanol (2) at 0.1 MPa and 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; , the Redlich− Kister correlations.

3.2. Ternary System. The changes of excess volumes of ternary system with compositions are shown in Figure 4. It is H

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Figure 5. Curves of Δη/mPa·s for the ternary system exotetrahydrodicyclopentadiene (1) + methylcyclohexane (2) + cyclopropanemethanol (3) correlated by the Nagata−Tamura Equation at (a) T = 293.15 K and (b) T = 328.15 K.

Figure 4. Curves of VEm/cm3·mol−1 for the ternary system exotetrahydrodicyclopentadiene (1) + methylcyclohexane (2) + cyclopropanemethanol (3) correlated by the Nagata−Tamura Equation at (a) T = 293.15 K and (b) T = 328.15 K.

temperature increasing due to the weakness of hydrogen bonding and the stronger dispersion force at a high temperature. From the measured data and calculations, it is indicated that the mixture from exo-tetrahydrodicyclopentadiene, methylcyclohexane, and cyclopropanemethanol has higher density and lower viscosity at certain component proportions.

evident that excess molar volumes (VEm) are sometimes negative, which is caused by the weakness of hydrogen bonding and spatial factors. When the proportion of cyclopropanemethanol is small, there exist few hydrogen bonds, and spatial factors play a leading role, which leads to negative values of VEm. When the proportion of cyclopropanemethanol is large enough, there are a lot of hydrogen bonds, and hydrogen bonding plays a leading role, which leads to positive values of VEm. The VEm increases with the temperature increasing, because of the weakness of hydrogen bonding at a high temperature. The viscosity deviations of the ternary systems change with mixture compositions are shown in Figure 5. It is evident that viscosity deviations (Δη) are negative in the whole concentration area, as a result of hydrogen bonds dissociating. The absolute value of viscosity deviations decreases with the

4. CONCLUSION Measurements on densities (ρ) and viscosities (η) at nine temperatures from 293.15 to 333.15 K and the pressure p = 0.1 MPa for the ternary system, exo-tetrahydrodicyclopentadiene (1) + methylcyclohexane (2) + cyclopropanemethanol (3), and three corresponding binary systems have been carried out over the whole composition range. The excess molar volumes (VEm) and viscosity deviations (Δη) are calculated through the measured data. The Redlich−Kister equation is used to fit the I

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data of binary systems, and Nagata-Tamura is used to fit the ternary system. The excess molar volumes for the mixtures of cyclopropanemethanol mixed with alkanes is influenced mainly by the hydrogen bonds among cyclopropanemethanol molecules, and the excess molar volumes of exo-tetrahydrodicyclopentadiene + methylcyclohexane is mainly influenced by the spatial factors. At the same time, viscosity deviations are observed to be negative, which is due to the dissociation of selfassociated molecules. Mixtures composed of exo-tetrahydrodicyclopentadiene, methylcyclohexane, and cyclopropanemethanol with higher density and lower viscosity at certain component proportions than single hydrocarbons can be prepared, and the fuels with high density and low viscosity are the actual needs in the field of aviation. Hence, these results are meaningful for the researches of fuel additive.

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ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jced.8b00409.

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The values of excess molar volumes (VEm), viscosity deviations (Δη) for binary systems and ternary systems. The coefficients and deviations of VEm and Δη with the semiempirical equation for binary and ternary system (PDF)

AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Tel.: 86-571-88981416. Fax: +86571-88981416. ORCID

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. 21773209). Notes

The authors declare no competing financial interest.

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REFERENCES

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DOI: 10.1021/acs.jced.8b00409 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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DOI: 10.1021/acs.jced.8b00409 J. Chem. Eng. Data XXXX, XXX, XXX−XXX