Density, Viscosity, Speed of Sound, Bulk Modulus ... - ACS Publications

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Density, Viscosity, Speed of Sound, Bulk Modulus, Surface Tension, and Flash Point of Binary Mixtures of 1,2,3,4-Tetrahydronaphthalene and Trans-decahydronaphthalene Dianne J. Luning Prak* and Bridget G. Lee Chemistry Department, United States Naval Academy, 572M Holloway Road, Annapolis, Maryland 21402, United States ABSTRACT: In this work, the properties of mixtures of 1,2,3,4-tetrahydronaphthalene and trans-decahydronaphthalene were measured. Density and viscosity were measured at temperatures ranging from (293.15 to 373.15) K, and speed of sound was measured at temperatures ranging from (293.15 to 333.15) K. For the mixtures, increasing the mole fraction of 1,2,3,4tetrahydronaphthalene and decreasing the temperature caused increases in density, speed of sound, bulk modulus, flash point, and surface tension. Mixture viscosities were lower than those of either component. Bulk moduli ranged from (1323 to 2092) MPa over (293.15 to 333.15) K. At room temperature, surface tensions ranged from (30.5 to 35.0) mN·m−1, and flash points ranged from (328.7 to 343.1) K. The density, speed of sound, and bulk modulus of hydrodepolymerized cellulosic diesel (HDCD) can be matched by mixtures of 1,2,3,4-tetrahydronaphthalene and trans-decahydronaphthalene. The flash point and viscosity of HDCD are higher than those of the mixtures, while its surface tension is lower than those of the mixtures. If combustion is more sensitive to density, speed of sound, and flash point and less sensitive to viscosity, flash point, and surface tension, then a surrogate mixture for HDCD could contain 1,2,3,4tetrahydronaphthalene and trans-decahydronaphthalene.

1. INTRODUCTION Research on alternative fuels has transitioned from preparing fuels from food sources to using waste bioproducts. Recently engine tests have been run using a mixture of petroleum-based diesel fuel with a new fuel derived from cellulose, hydroprocessed depolymerized cellulosic diesel (HDCD).1 HDCD is produced by thermocatalytically converting lignocellulose to a biocrude product, which is then hydrotreated to remove oxygen and other atoms and fractionated to produce a diesel-like product. HDCD has been reported to consist of alicyclic, cyclic, and aromatic compounds, including 1,2,3,4-tetrahydronaphthalene (tetralin).1 French et al.2 also reported that mild hydrotreating of a pyrolytic lignin produced alkyl cyclohexanes, hydro-1H-indenes, and hydronaphthalenes, including transdecahydronaphthalene (trans-decalin). One way to better understand HDCD combustion is to develop numerical models simulating the combustion, but such models require that the physical and chemical properties of the fuel be characterized. The modeling process can be simplified if a simple mixture that has similar properties to the fuel can be prepared. Such a mixture with a few components is called a surrogate mixture. Many surrogate mixtures have been prepared for complex fuels,2−14 such as HDCD. Surrogate mixture formulation often starts with a limited number of compounds from which to choose, called a surrogate palette. The palette for diesel fuels includes normal alkanes, branched alkanes, aromatics, tetralin, and cyclohexanes including trans-decalin.14 The goal of this study was to determine the composition of a two-component This article not subject to U.S. Copyright. Published XXXX by the American Chemical Society

surrogate mixture containing 1,2,3,4-tetrahydronaphthalene and trans-decahydronaphthalene that best matched the physical properties reported for an HDCD fuel. These components were selected because 1,2,3,4-tetrahydronaphthalene has been found in the HDCD fuel and trans-decahydronaphthalene was found in the hydrotreated pyrolytic lignin-based fuel.1,2 The physical properties measured in this work are those that impact the fuel combustion and delivery to the engines, specifically flash point, surface tension, density, viscosity, and speed of sound. Flash point is an indicator of fuel combustibility, and military diesel fuel is required to have a flash point greater than 335.15 K.15 Fuel pumping and droplet formation in the engine cylinders depend on surface tension, density, and viscosity. These parameters have been used in numerical models multicomponent fuel drop vaporization.16−19 Fuel injection timing depends on bulk modulus, which is calculated from speed of sound and density.4,20 In this work, the density, viscosity, surface tension, speed of sound, and flash point were measured for binary mixtures of 1,2,3,4-tetrahydronaphthalene and trans-decahydronaphthalene. These properties and the calculated bulk moduli were then compared with values for HDCD. The goal of this work was to determine which surrogate mixture, if any, best matches the properties of HDCD. This information could then be used for numerical Received: December 21, 2015 Accepted: June 6, 2016

A

DOI: 10.1021/acs.jced.5b01075 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data

Article

Table 1. Sample Information

a

chemical name

CAS number

molar mass (g·mol‑1)a

source/lot number

mole fraction purity

analysis method

1,2,3,4-tetrahydronaphthalene (C10H12) Trans-decahydronaphthalene (C10H18)

119-64-2 493-02-7

132.202 ± 0.005 138.250 ± 0.006

Aldrich/MKBN2319 V TCI/R5K8F

0.989 0.995

GCb GCb

Calculated using values in ref 28. bGas−liquid chromatography as specified in the Certificate of Analysis provided by the chemical supplier.

from which the average and standard deviation were determined. The expanded uncertainty of density, viscosity, speed of sound, surface tension, and flash point was determined by multiplying the standard deviation of the measurements (taken at each temperature as described above) by 2. When a normal distribution is assumed, multiplying by a coverage factor of 2 produces a 95% confidence interval. The purity of a sample also impacts the precision of the measurements, and this was estimated by multiplying the expanded uncertainty by a factor of 10 for the densities, viscosities, speeds of sound, and surface tensions of these mixtures.27

simulations of the combustion process. Two-component mixture properties can also be used by numerical modelers who are trying to predict mixture properties using numerical simulations.

2. MATERIALS Trans-decahydronaphthalene and 1,2,3,4-tetrahydronaphthalene were used as received from the supplier (Table 1). The mixtures were prepared by pipetting each component into a 40 mL clear borosilicate vial (C&G Containers who had prepared the vials using Protocol A level 1 cleaning procedure). The vial was weighed after each addition at room temperature on a Mettler Toledo AG204 analytical balance, that has an error of 0.0004 g. The vials were then sealed with a cap containing a Teflon septa and mixed before analysis. The combined expanded uncertainty (level of confidence = 0.95, k = 2) for the mass fraction and mole fraction of 1,2,3,4-tetrahydronaphthalene in trans-decahydronaphthalene are 0.0001 and 0.0001, respectively.

4. RESULTS 4.1. Density. The measured density values of the NISTcertified toluene standard match the certified values within the expanded uncertainty of the measurements reported in Table 2, demonstrating the accuracy of the DSA 5000. The density values of the 1,2,3,4-tetrahydronaphthalene and trans-decahydronaphthalene mixtures are given in Table 3. The pure component values are measurements taken in our lab under the same conditions as reported herein.26 No values for mixtures

3. METHODS An Anton Paar DSA 5000 Density and Sound Analyzer was used to measure the density and speed of sound of mixtures of 1,2,3,4-tetrahydronaphthalene and trans-decahydronaphthalene at five temperatures between (293.15 and 333.15) K. This instrument measures speed of sound using a propagation time technique with one transducer emitting sound waves at a frequency of approximately 3 MHz and a second transducer receiving those waves.21 The averages and standard deviations of density and speed of sound were calculated from measurements of two or more samples. An Anton Paar SVM 3000 Stabinger Viscometer was used to measure the viscosity and density at eight temperatures between (293.15 and 373.15) K, and measurements of two samples were used to determine the average and standard deviation. The methods for cleaning, calibrating, and checking the accuracy of these instruments have been described previously.22,23 The accuracy of the density measurements was tested using a NIST toluene density reference standard, and the results are reported herein. A Kruss DS100 drop-shape analyzer22−26 was used to measure the surface tension of the organic liquid mixtures. Software input parameters include air density, organic liquid density, and the needle diameter, which was measured using a micrometer (Mitutoyo). A droplet of the organic liquid mixture is formed on the tip of a needle, where it is magnified, recorded, and its shape is fit to the Young-LaPlace equation. More than 15 surface tension measurements were taken for each droplet formed, and at least three droplets of each mixture were measured. From these data, the average and standard deviation were determined. A Setaflash Series 8 closed cup flash-point tester model 82000-0 (Stanhope-Seta) was used to measure flashpoint in temperature ramping mode. The manufacturer’s literature specifies that this flash-point tester conforms to ASTM D3828 (gas ignition option), ASTM D1655 (gas ignition option), ASTM D3278, ASTM D7236, and ASTM E502. Two or more measurements were taken for each mixture

Table 2. Density and Speed of Sound Measurements for NIST- Certified Toluene Standarda density/kg·m−3

a

T/K 293.15 303.15 313.15 323.15 333.15 343.15 353.15

this study DSA 5000 866.81(6) 857.49(7) 848.11(4) 838.66(1) 829.12(4)

this studya SVM 3000

literature

b

difference between values in literature and from DSA 5000

866.8 866.828 ± 0.031 857.5 857.507 ± 0.032 848.1 848.131 ± 0.033 838.7 838.684 ± 0.034 829.1 829.152 ± 0.035 819.5 819.516 ± 0.037 809.7 809.761 ± 0.038 speed of sound/m·s−1

0.012 0.004 0.017 0.023 0.028

T/K

this study DSA 5000

literature

293.15 303.15 313.15 323.15 333.15

1326.5 1283.5 1241.0 1198.9 1157.5

1324.3e, 1326.3 ± 0.3c, 1326.9d 1281.6e, 1283.3 ± 0.3c 1239.8e, 1240.6 ± 0.3c, 1240.9d 1198.6e, 1198.6 ± 0.3c, 1198.9d 1157.2 ± 0.3c, 1157.7d, 1158.0e

a

Standard uncertainty u is u(T) = 0.01 K, and an expanded uncertainty for the measured values are Uc(ρ) = 0.07 kg·m−3 for the DSA 5000 and 0.2 kg·m−3 for the SVM 3000, and Uc(c) = 0.3 m·s−1 (level of confidence = 0.95, k = 2). The differences in uncertainty for different temperatures arise from differences in the level of precision for the two instruments. The SVM 3000 is less precise. The average pressure for these measurements was 0.101 MPa with an expanded uncertainty Uc(P) = 0.001 MPa (level of confidence = 0.95, k = 2). bReference 29. Values for liquid density of SRM 211d “as shipped”. Error bars are the reported standard uncertainties, uN (k = 1). cReference 30. dReference 21. eReference 48. B



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Table 3. Densities, in kg·m−3, of Mixtures of 1,2,3,4-Tetrahydronaphthalene (1) + Trans-decahydronaphthalene from T = (293.15 to 373.15) K and 0.1 MPaa w1

x1

T/K = 293.15

T/K = 303.15

T/K = 313.15

T/K = 323.15

T/K = 333.15

T/K = 343.15

T/K = 353.15

T/K = 363.15

T/K = 373.15

0.000 0.1003 0.2002 0.3000 0.4002 0.5000 0.6000 0.7000 0.8000 0.8999 1.000

0.000 0.1044 0.2075 0.3094 0.4109 0.5112 0.6106 0.7093 0.8070 0.9039 1.000

869.75b 878.7(0) 887.8(9) 897.2(8) 906.9(0) 916.6(7) 926.6(9) 936.8(9) 947.3(2) 957.9(5) 968.8b

862.29b 871.1(8) 880.3(3) 889.6(7) 899.2(3) 908.9(6) 918.9(2) 929.0(9) 939.4(7) 950.0(7) 960.9b

854.82b 863.6(8) 872.7(6) 882.0(5) 891.5(5) 901.2(4) 911.1(5) 921.2(7) 931.6(1) 942.1(7) 953.0b

847.34b 856.1(5) 865.1(8) 874.4(2) 883.8(7) 893.5(1) 903.3(7) 913.4(5) 923.7(5) 934.2(6) 945.0b

839.83b 848.60 857.58 866.77 876.17 885.76 895.58 905.62 915.87 926.34 937.1b

832.30b 841.0 850.0 859.1 868.3 878.0 887.9 897.7 907.9 918.5 929.1b

824.7b 833.2 842.3 851.4 860.6 870.2 880.0 889.8 900.0 910.5 920.9b

817.0b 825.5 834.6 843.5 852.8 862.3 872.1 881.8 892.0 902.4 912.9b

809.4b 817.9 826.9 835.8 844.9 854.5 864.2 874.0 883.9 894.4 904.8b

a

w1 is the mass fraction of 1,2,3,4-tetrahydronaphthalene in mixtures with trans-decahydronaphthalene and x1 is the mole fraction of 1,2,3,4tetrahydronaphthalene in mixtures with trans-decahydronaphthalene. Standard uncertainty u is u(T) = 0.01 K, expanded uncertainties Uc are Uc(ρ) = 0.2 kg·m−3 for T < 343.15 K and Uc(ρ) = 0.5 kg·m−3 for T ≥ 343.15 K (level of confidence = 0.95, k = 2) and combined expanded uncertainty is Uc(x1) = 0.0001. The differences in uncertainty for different temperatures arise from differences in the level of precision for the two instruments. The SVM 3000 is less precise. The average pressure for these measurements was 0.101 MPa with an expanded uncertainty Uc(P) = 0.001 MPa (level of confidence = 0.95, k = 2). bReference 26.

were not linear. A second-order polynomial was used to fit the density and mole fraction data:

are available in the literature for comparison. For the mixtures, the density increased as mole fraction of the 1,2,3,4tetrahydronaphthalene increased (Figure 1), but the changes

ρ /kg·m−3 = Ax12 + Bx1 + C

(1)

In this equation x1 is the mole fraction of the 1,2,3,4tetrahydronaphthalene and A, B, and C are fitting parameters, which are given in Table 4. The standard error of the fit was calculated using σ=

∑ (Pmeasured − Pm,cal)2 N−n

(2)

in which Pmeasured is the measured density, Pm,cal is the fitted density, N is the number of experimental data, and n is the number of parameters in the fitting equation. The fitting procedure was conducted using Microsoft Excel 2010, and the results are given in Table 4. The fits are good with R2 > 0.9999 as shown in Figure 1. The excess molar volumes (VmE) of the 1,2,3,4-tetrahydronaphthalene and trans-decahydronaphthalene mixtures were calculated using the following equation:

Figure 1. Densities of 1,2,3,4-tetrahydronaphthalene (1) + transdecahydronaphthalene mixtures at □, 293.15 K; ■, 303.15 K; △, 313.15 K; ▲, 323.15 K; ◊, 333.15 K; ◆, 343.15 K; ○, 353.15 K; ●, 363.15 K; ×, 373.15 K. Error bars, which are the combined uncertainties with 0.95 level of confidence (k = 2), are smaller than the symbols. Lines shown are second-order fits using eq 1 with the coefficients in Table 4.

VmE =

M1x1 + M 2x 2 Mx Mx − 11 − 2 2 ρm ρ1 ρ2

(3)

Table 4. Parameters for eq 1, ρ = Ax12 + Bx1 + C, that Correlate Density, in kg·m−3, to Mole Fraction of 1,2,3,4Tetrahydronaphthalene (x1) in (1,2,3,4-Tetrahydronaphthalene + Trans-decahydronaphthalene) Mixtures, T = (293.15 to 373.15) K, and 0.1 MPaa T/K 293.15 303.15 313.15 323.15 333.15 343.15 353.15 363.15 373.15 a

A kg·m−3 14.8 14.9 14.9 15.0 15.0 15.1 14.7 14.9 14.7

± ± ± ± ± ± ± ± ±

0.3 0.3 0.3 0.3 0.3 0.7 0.6 0.6 0.7

B kg·m−3

C kg·m−3

R2

σ kg·m−3

± ± ± ± ± ± ± ± ±

869.77 ± 0.06 862.31 ± 0.07 854.85 ± 0.07 847.37 ± 0.07 839.87 ± 0.08 832.3 ± 0.1 824.7 ± 0.1 817.0 ± 0.1 809.4 ± 0.2

0.9999 0.9999 0.9999 0.9999 0.9999 0.9999 0.9999 0.9999 0.9999

0.02 0.04 0.04 0.04 0.04 0.08 0.08 0.08 0.09

84.2 83.7 83.1 82.6 82.1 81.6 81.5 80.9 80.6

0.3 0.3 0.3 0.3 0.4 0.3 0.7 0.7 0.7

The “±” symbols for the coefficients A, B, and C represent the 95% confidence interval. The σ is the standard error of the fit as given by eq 2. C



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Table 5. Speeds of Sound, in m·s−1, of Mixtures of 1,2,3,4Tetrahydronaphthalene (1) + Trans-decahydronaphthalene from T = (293.15 to 333.15) K and 0.1 MPaa

in which ρm is the density of the mixture, ρ1 and ρ2 are the pure component densities, M1 and M2 are the molar masses, and x1 and x2 are the mole fractions of 1,2,3,4-tetrahydronaphthalene as component 1 and trans-decahydronaphthalene as component 2. The calculated excess molar volumes for all mixtures at all temperature studied herein had combined expanded uncertainties (level of confidence = 0.95, k = 2) that were larger than the values themselves as demonstrated in Figure 2

x1

T/K = 293.15

T/K = 303.15

T/K = 313.15

T/K = 323.15

T/K = 333.15

0.000 0.1044 0.2075 0.3094 0.4109 0.5112 0.6106 0.7093 0.8070 0.9039 1.000

1397.9b 1405.0 1412.5 1420.5 1428.8 1437.7 1446.9 1456.8 1467.0 1477.9 1489.5b

1357.5b 1364.8 1372.4 1380.5 1388.9 1397.9 1407.2 1417.2 1427.6 1438.6 1450.2b

1317.9b 1325.3 1333.1 1341.3 1349.9 1358.9 1368.4 1378.4 1388.9 1400.0 1411.5b

1279.1b 1286.7 1294.5 1302.8 1311.5 1320.7 1330.2 1340.4 1350.9 1362.0 1373.6b

1241.1b 1248.7 1256.7 1265.1 1273.9 1283.1 1292.7 1303.0 1313.5 1324.8 1336.4b

a

x1 is the mole fraction of 1,2,3,4-tetrahydronaphthalene in mixtures with trans-decahydronaphthalene. Standard uncertainty u is u(T) = 0.01 K, expanded uncertainty Uc is Uc(c) = 0.9 m·s−1, and combined expanded uncertainty is Uc(x1) = 0.0001 (level of confidence = 0.95, k = 2). The average pressure for these measurements was 0.101 MPa with an expanded uncertainty Uc(P) = 0.001 MPa (level of confidence = 0.95, k = 2). bReference 26.

Figure 2. Comparison of excess molar volumes in the current study at (○) 293.15 K and (□) 303.15 K with fitted line and values at (■) 298.15 K from Chylinski and Stryjek.49 Error bars for the data shown here at 293.15 K are the combined expanded uncertainties with 0.95 level of confidence (k = 2).

conditions as reported herein.26 No values for mixtures are available in the literature for comparison. As the mole fraction of the 1,2,3,4-tetrahydronaphthalene increased, the speed of sound increased as shown in Figure 3, but the trend is not

for 293.15 and 303.15 K. Also shown are excess molar volumes and the fitted equation at 298.15 K calculated by Chylinski and Stryjek.49 Their values are slightly lower than the current values but fall within the error bars of the current values. Both studies show that the excess molar volumes are very close to zero. This suggests that the packing of the molecules in the mixtures differs little from that of the pure components. Positive, negative, and zero values of excess molar volume have been found for binary mixtures 1,2,3,4-tetrahydronaphthalene or trans-decahydronaphthalene with other compounds. Researchers have found that excess molar volumes for 1,2,3,4tetrahydronaphthalene transition from negative values when mixed with linear alkanes with low carbon numbers ( 0.999) as shown in Figure 3. The isentropic bulk modulus, Ks, of each 1,2,3,4-tetrahydronaphthalene and trans-decahydronaphthalene mixture was calculated at each temperature and ambient pressure from the speed of sound (c) and density (ρ) by K s/Pa = (c 2/m 2·s−2)(ρ /kg·m−3)

(4)

The calculated values are given in Table 7. The bulk modulus increases with increasing mole fraction of trans-decahydronaphD



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Table 6. Parameters for Second-Order Model, c = Ax12 + Bx1 + C, That Correlate Speed of Sound, c in m·s−1, to Mole Fraction of 1,2,3,4-Tetrahydronaphthalene, x1, in (1,2,3,4Tetrahydronaphthalene + Trans-decahydronaphthalene) Mixtures and Associated Standard Error (eq 2) Over Temperature Range T = (293.15 to 333.15) Ka T/K 293.15 303.15 313.15 323.15 333.15

A m·s−1 28.0 27.9 27.3 27.0 26.9

± ± ± ± ±

1.6 1.5 1.3 1.3 1.3

B m·s−1 63.1 64.4 65.9 67.1 68.0

± ± ± ± ±

1.7 1.6 1.4 1.3 1.3

C m·s−1 1398.1 1357.7 1318.1 1279.3 1241.3

± ± ± ± ±

0.4 0.3 0.3 0.3 0.3

R2

σ m·s−1

0.9999 0.9999 0.9999 0.9999 0.9999

0.21 0.19 0.16 0.16 0.16

K.36 Papaloannou et al.37 reported viscosity values lower than pure component values for systems of cyclohexane and benzene at low cyclohexane concentrations. The cyclohexane and benzene are similar in structure to trans-decalin and tetralin. Korsten stated that the behavior seen for the cyclohexane− benzene system occurs when the pure-component viscosity curves cross each other between the freezing and critical temperatures.38 The structure and/or interaction of these types of molecules allows them to slide past each more easily in mixtures than in the pure components themselves. The McAllister three-body model39 was used to fit the kinematic viscosity data: ln νm = x13 ln ν1 + 3x12x 2 ln ν1,2 + 3x1x2 2ln ν2,1 + x 2 3 ln ν2

The “±” symbols for the coefficients A, B, and C, represent the 95% confidence interval. a

⎛1⎛ ⎛ M ⎞ M ⎞⎞ − ln⎜x1 + x 2 2 ⎟ + 3x12x 2 ln⎜⎜ ⎜2 + 2 ⎟⎟⎟ M1 ⎠ M1 ⎠⎠ ⎝ ⎝3⎝

Table 7. Isentropic Bulk Modulus, in MPa, Values of Mixtures of 1,2,3,4-Tetrahydronaphthalene (1) + and Transdecahydronaphthalene from T = (293.15 to 333.15) K and 0.1 MPaa x1

T/K = 293.15

T/K = 303.15

T/K = 313.15

T/K = 323.15

T/K = 333.15

0.000 0.1044 0.2075 0.3094 0.4109 0.5112 0.6106 0.7093 0.8070 0.9039 1.000

1699b 1735 1772 1811 1851 1895 1940 1988 2039 2092 2149b

1589b 1623 1658 1695 1735 1776 1820 1866 1915 1966 2021b

1485b 1517 1551 1587 1625 1664 1706 1750 1797 1847 1899b

1386b 1417 1450 1484 1520 1558 1598 1641 1686 1733 1783b

1294b 1323 1354 1387 1422 1458 1497 1537 1580 1626 1674b

⎛1⎛ ⎛M ⎞ M ⎞⎞ + 3x1x 2 2 ln⎜⎜ ⎜1 + 2 2 ⎟⎟⎟ + x 2 3 ln⎜ 2 ⎟ M1 ⎠⎠ ⎝ M1 ⎠ ⎝3⎝

(5)

Here νm is the kinematic viscosity of the binary mixture, x1 and x2 are the mole fractions, ν1 and ν2 are the kinematic viscosities of the pure components, and M1 and M2 are the molar masses of 1,2,3,4-tetrahydronaphthalene as component 1 and transdecahydronaphthalene as component 2. To determine the interaction parameters ν2,1 and ν1,2, the GRG nonlinear engine of the SOLVER function in Microsoft Excel 2010 was used to minimize the sum of the square of the difference between the value calculated by the model in eq 5, νm,calc, and the measured kinematic viscosity of the binary mixture, νmeasured. The standard error for the fit (σ) was determined by eq 2, in which Pmeasured is the measured viscosity and Pm,cal is the fitted viscosity. Both the fitted values of ν2,1, and ν1,2, and the standard errors of the fits are given in Table 9 at each temperature. Figure 4 shows that the model fits the data well. Viscosity deviation (Δviscosity) can be calculated as the differences between the measured value of the mixture and its “ideal value”:

a

x1 is the mole fraction of 1,2,3,4-tetrahydronaphthalene in mixtures with trans-decahydronaphthalene. Standard uncertainty u is u(T) = 0.01 K, and combined expanded uncertainties Uc are Uc(x1) = 0.0001 and Uc (bulk modulus) = 1 MPa, (level of confidence = 0.95, k ≈ 2). The average pressure for these measurements was 0.101 MPa with an expanded uncertainty Uc(P) = 0.001 MPa (level of confidence = 0.95, k = 2). bReference 26.

Δviscosity = viscosity (measured) − viscosity (ideal)

(6)

where the “ideal values” have been represented in terms of kinematic viscosity, νideal,

thalene and decreasing temperature. The speed of sound of HDCD was reported to be 1433.2 m·s−1 at 293.15 K.1 This speed of sound value falls between (1428.8 and 1437.7) MPa for the 0.4002 and 0.5000 mass fraction of 1,2,3,4tetrahydronaphthalene in trans-decahydronaphthalene, respectively. The bulk modulus value for an HDCD was reported to be 1860 MPa at 293.15 K.1 This bulk modulus value falls between (1851 and 1895) MPa for the 0.4002 and 0.5000 mass fraction of 1,2,3,4-tetrahydronaphthalene in trans-decahydronaphthalene, respectively. 4.3. Viscosity. The dynamic and kinematic viscosity values of 1,2,3,4-tetrahydronaphthalene and trans-decahydronaphthalene mixtures and their mixtures are given in Table 8 as a function of the mole fraction (x1) of 1,2,3,4-tetrahydronaphthalene or trans-decahydronaphthalene. The pure component values are measurements taken in our lab under the same conditions as reported herein.26 As the mole fraction of 1,2,3,4tetrahydronaphthalene increases, the viscosity decreases to values below those of 1,2,3,4-tetrahydronaphthalene and transdecahydronaphthalene until a mole fraction of 0.8999 is reached (Figure 4). A similar behavior was shown graphically by Bird and Daly in 1939 for trans-decalin and tetralin at 308.15

νideal = x1ν1 + x 2ν2

(7)

ln(νideal) = x1 ln(ν1) + x 2 ln(ν2)

(8)

and dynamic viscosity, ηideal, ηideal = x1η1 + x 2η2

(9)

ln(ηideal ) = x1 ln(η1) + x 2 ln(η2)

(10)

ν1 and ν2 are the kinematic viscosities of the pure components, η1 and η2 are the dynamic viscosities of the pure components, and x 1 and x 2 are the mole fractions of the pure components.37,40−44 In this study eq 10 was used to determine the “ideal values,” and the deviation of those ideal values from the measured values are given in Table 10. The viscosity deviations shown in Figure 5 for all the mixtures are negative. The error bars are not shown because they would make seeing the trends difficult. (Please see Table 10 for values where the combined expanded uncertainties are greater than the values themselves.) The negative viscosity deviations indicate that the E



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Table 8. Viscosities of Mixtures of 1,2,3,4-Tetrahydronaphthalene (1) + Trans-decahydronaphthalene from T = (293.15 to 373.15) K and 0.1 MPaa x1

viscosity

T/K = 293.15

T/K = 303.15

T/K = 313.15

T/K = 323.15

T/K = 333.15

T/K = 343.15

T/K = 353.15

T/K = 363.15

T/K = 373.15

0.000

η/Pa·s ν/mm2·s−1 η/mPa·s ν/mm2·s−1 η/mPa·s ν/mm2·s−1 η/mPa·s ν/mm2·s−1 η/mPa·s ν/mm2·s−1 η/mPa·s ν/mm2·s−1 η/mPa·s ν/mm2·s−1 η/ mPa·s ν/mm2·s−1 η/mPa·s ν/mm2·s−1 η/mPa·s ν/mm2·s−1 η/mPa·s ν/mm2·s−1

2.14b 2.46b 2.07 2.36 2.03 2.29 2.02 2.25 2.00 2.21 2.02 2.20 2.04 2.20 2.07 2.21 2.11 2.22 2.17 2.26 2.25b 2.32b

1.79b 2.07b 1.74 2.00 1.71 1.94 1.70 1.91 1.68 1.87 1.69 1.86 1.71 1.86 1.73 1.86 1.75 1.87 1.80 1.90 1.85b 1.93b

1.51b 1.77b 1.48 1.71 1.46 1.67 1.44 1.64 1.43 1.61 1.44 1.60 1.45 1.59 1.46 1.59 1.48 1.59 1.51 1.60 1.55b 1.63b

1.30b 1.53b 1.27 1.48 1.25 1.45 1.24 1.42 1.23 1.39 1.24 1.39 1.25 1.38 1.26 1.38 1.27 1.38 1.29 1.39 1.32b 1.40b

1.12b 1.34b 1.10 1.30 1.09 1.27 1.08 1.25 1.07 1.22 1.08 1.22 1.08 1.21 1.09 1.20 1.10 1.20 1.12 1.21 1.14b 1.22b

0.982b 1.18b 0.968 1.15 0.957 1.13 0.950 1.11 0.943 1.09 0.947 1.08 0.951 1.07 0.958 1.07 0.968 1.07 0.982 1.07 0.998b 1.07b

0.867b 1.05b 0.856 1.03 0.847 1.01 0.842 0.99 0.836 0.972 0.840 0.965 0.843 0.958 0.849 0.955 0.858 0.954 0.870 0.956 0.882b 0.958b

0.774b 0.947b 0.765 0.926 0.758 0.908 0.753 0.893 0.749 0.878 0.752 0.872 0.755 0.866 0.760 0.862 0.768 0.861 0.778 0.863 0.789b 0.865b

0.697b 0.861b 0.689 0.842 0.683 0.826 0.680 0.813 0.676 0.800 0.679 0.795 0.685 0.793 0.687 0.786 0.694 0.785 0.703 0.786 0.713b 0.788b

0.1044 0.2075 0.3094 0.4109 0.5112 0.6106 0.7093 0.8070 0.9039 1.000 a

x1 is the mole fraction of 1,2,3,4-tetrahydronaphthalene in mixtures with trans-decahydronaphthalene. Standard uncertainty u is u(T) = 0.01 K, an expanded uncertainty Uc is Uc(η) = 0.02 mPa·s and combined expanded uncertainties are Uc(x1) = 0.0001 and Uc(ν) = 0.02 mm2·s−1 (level of confidence = 0.95, k = 2). The average pressure for these measurements was 0.101 MPa with an expanded uncertainty Uc(P) = 0.001 MPa (level of confidence = 0.95, k = 2). The dynamic viscosity, η, is measured by the instrument, and the kinematic viscosity, ν, is calculated by dividing dynamic viscosity by density. bReference 26.

Table 9. Values of the Coefficients for McAllister Equation, eq 5, and Associated Standard Error (eq 2) for Binary Mixtures of 1,2,3,4-Tetrahydronaphthalene (1) + Transdecahydronaphthalene from T = (293.15 to 373.15) K

Figure 4. Viscosities of 1,2,3,4-tetrahydronaphthalene (1) + transdecahydronaphthalene mixtures at (□) 293.15 K; (■) 303.15 K; (△) 313.15 K; (▲) 323.15 K; (◊) 333.15 K; (◆) 343.15 K; (○) 353.15 K; (●) 363.15 K; (×), 373.15 K. Error bars, which are the combined uncertainties with 0.95 level of confidence (k = 2), are smaller than the symbols. Lines shown are fits using eq 5 with the coefficients in Table 9.

T/K

ν12/mm2·s−1

ν21/mm2·s−1

103·σ/mm2·s−1

293.15 303.15 313.15 323.15 333.15 343.15 353.15 363.15 373.15

2.14 1.81 1.56 1.35 1.19 1.05 0.943 0.852 0.779

2.15 1.83 1.58 1.38 1.22 1.08 0.968 0.876 0.797

6.0 3.6 2.5 1.8 1.8 1.6 1.4 1.1 1.4

n

Δν = x1x 2 ∑ Aj (x1 − x 2) j = x1x 2[A 0 + A1(x1 − x 2)] j=0

(11)

where Aj are adjustable parameters, j is the order of the polynomial, x1 is the mole fraction of 1,2,3,4-tetrahydronaphthalene, and x2 is the mole fraction of trans-decahydronaphthalene. The standard error for the fit (σ) was determined by eq 2, where Pmeasured is the calculated viscosity deviation and Pfit is the fitted viscosity deviation. The fitted values of A0, and A1 and the standard errors of the fits are given in Table 11 for each temperature. A two-parameter fit was selected because the data did not appear to be exactly symmetrical about x1 = 0.5 and more terms did not significantly improve the fit as indicated by

molecules in the mixture are sliding past each other more easily than would be predicted by an ideal mixture. As the temperature increases, the deviation from ideal behavior is less. Note that if eq 7 was used in place of eq 10 for the ideal values, the viscosity deviations are still negative and the deviations from ideal are less at higher temperatures as was seen when using eq 10. A Redlich−Kister type expression was used to fit the viscosity deviations: F



Article

Table 10. Viscosity Deviation, in mPa·s, of 1,2,3,4-Tetrahydronaphthalene (1) in (1,2,3,4-tetrahydronaphthalene + transdecahydronaphthalene) Mixtures from T = (293.15 to 373.15) K and 0.1 MPaa T/K

x1= 0.1044

x1= 0.2075

x1= 0.3094

x1= 0.4109

x1= 0.5112

x1= 0.6106

x1= 0.7093

x1= 0.8070

x1= 0.9039

293.15 303.15 313.15 323.15 333.15 343.15 353.15 363.15 373.15

−0.081 −0.053b −0.036b −0.027b −0.020b −0.015b −0.012b −0.011b −0.010b

−0.129 −0.090 −0.065 −0.047 −0.036 −0.028b −0.023b −0.019b −0.017b

−0.155 −0.111 −0.081 −0.060 −0.046 −0.037 −0.030 −0.025b −0.022b

−0.181 −0.132 −0.098 −0.073 −0.057 −0.046 −0.037 −0.031 −0.028

−0.175 −0.126 −0.093 −0.070 −0.054 −0.043 −0.035 −0.029 −0.026

−0.167 −0.120 −0.088 −0.066 −0.051 −0.041 −0.033 −0.028 −0.022b

−0.149 −0.107 −0.078 −0.058 −0.044 −0.035 −0.028 −0.024b −0.021b

−0.120 −0.084 −0.060 −0.044 −0.034 −0.027b −0.021b −0.018b −0.016b

−0.067b −0.041b −0.036b −0.025b −0.017b −0.014b −0.011b −0.009b −0.009b

a x1 is the mole fraction of 1,2,3,4-tetrahydronaphthalene in mixtures with trans-decahydronaphthalene. Standard uncertainties u are u(T) = 0.01 K and combined expanded uncertainty Uc is U(x1) = 0.0001 (level of confidence = 0.95, k ≈ 2). bThe combined expanded uncertainty (level of confidence = 0.95, k = 2) in these calculated values is larger than the values themselves.

and 3,4′-dimethyl-1,1′biphenyl. The 5-butyl-1,2,3,4-tetrahydronaphthalene has a viscosity of 3.93 mm2·s−1 at 311 K and 2.4 mm2·s−1 at 333.15 K, which would make it have a higher viscosity at 293.15 K than HDCD, so it could increase the viscosity of the two-component system.45 A compound with a similar structure to 3,4′-dimethyl-1,1′biphenyl is 3,3′-dimethyl1,1′biphenyl, the viscosity of which is 5.90 mPa·s at 298.15 K.45 It too could be added to increase viscosity. The 5-butyl-1,2,3,4tetrahydro-naphthalene and 3,3′-dimethyl-1,1′biphenyl are liquids at room temperature and should mix well with the compounds in the current study. Their density values, 930 kg· m−3 for 5-butyl-1,2,3,4-tetrahydro-naphthalene and 1000 kg· m−3 for 3,3′-dimethyl-1,1′biphenyl at 293.15 K, would be reasonable so as to allow the mixture density to continue to match the HDCD.46,47 4.4. Surface Tension and Flash Point. The surface tension and flash point values are given in Table 12 for the mixtures studied herein as a function of the mole fraction of 1,2,3,4-tetrahydronaphthalene, x1, in trans-decahydronaphthalene. The pure component values are measurements taken in our lab under the same conditions as reported herein.26 No values for mixtures are available in the literature for

Figure 5. Viscosity deviations of 1,2,3,4-tetrahydronaphthalene (1) + trans-decahydronaphthalene mixtures as calculated by eq 8 shown at □, 293.15 K; ■, 303.15 K; △, 313.15 K; ▲, 323.15 K; ◊, 333.15 K; ◆, 343.15 K; ○, 353.15 K; ●, 363.15 K; ×, 373.15 K. Lines shown are fits to eq 11 with the coefficients in Table 11.

Table 11. Parameters for Redlich−Kister equation, eq 11, for Viscosity Deviation of Mixtures of Binary Mixtures of 1,2,3,4-Tetrahydronaphthalene + Transdecahydronaphthalene and Associated Standard Error (eq 2) T/K

A0 mPa·s

A1 mPa·s

σ mPa·s

293.15 303.15 313.15 323.15 333.15 343.15 353.15 363.15 373.15

−0.734 −0.523 −0.383 −0.285 −0.218 −0.175 −0.140 −0.119 −0.104

0.0318 0.0270 0.0080 0.0096 0.0071 0.0028 0.0063 0.0031 0.0063

0.007 0.004 0.003 0.002 0.002 0.001 0.001 0.001 0.001

Table 12. Surface Tensions and Flash Points of Mixtures of 1,2,3,4-Tetrahydronaphthalene (1) + Transdecahydronaphthalenea x1 0.000 0.1044 0.2075 0.3094 0.4109 0.5112 0.6106 0.7093 0.8070 0.9039 1.000

the standard error. The model fits the data well as shown in Figure 5. The viscosity value for an HDCD was reported to be 4.82 mm2·s−1 (4.36 mPa·s) at 293.15 K.1 This viscosity value is much greater than the values reported herein, suggesting that the HDCD contains other alicyclic and aromatic compounds that cause a greater resistance to flow that do the mixtures studied herein. French et al.2 reported some components of a hydrotreated oil derived from the pyrolysis of lignin that could possibly be added to increase the viscosity of a surrogate mixture, which include 5-butyl-1,2,3,4-tetrahydro-naphthalene

surface tension (mN·m−1) 30.5b 30.5 ± 31.0 ± 31.4 ± 32.1 ± 32.3 ± 32.9 ± 33.6 ± 34.1 ± 35.0 ± 36.1b

0.2 0.2 0.3 0.2 0.2 0.2 0.2 0.5 0.2

flash point (K) 326.7b 328.8 ± 330.5 ± 333.5 ± 333.7 ± 334.7 ± 335.7 ± 337.7 ± 340.5 ± 343.1 ± 347.7b

2 2 2 2 6 2 2 2 2

a

x1 is the mole fraction of 1,2,3,4-tetrahydronaphthalene in mixtures with trans-decahydronaphthalene. Surface tension measurements were taken at room temperature, T = 294.2 K. Expanded uncertainties Uc for surface tension Uc(surface tension) and flash point Uc( f lash point) are indicated by the symbol “±” and combined expanded uncertainty for mole fraction is U(x1) = 0.0001 (level of confidence = 0.95, k = 2). b Reference 26. G



Article

Internal Combustion Engine Division Conference, Nov. 8−10, 2015. ICEF2015−1083. (2) French, R. J.; Black, S. K.; Myers, M.; Stunkel, J.; Gjersing, E.; Iisa, K. Hydrotreating the organic fraction of biomass pyrolysis oil to a refinery intermediate. Energy Fuels 2015, 29, 7985−7992. (3) Allen, C.; Valco, D.; Toulson, E.; Edwards, T.; Lee, T. Ignition behavior and surrogate modeling of JP-8 and of camelina and tallow hydrotreated renewable jet fuels at low temperatures. Combust. Flame 2013, 160, 232−239. (4) Luning Prak, D. J.; Cowart, J. S.; Hamilton, L. J.; Hoang, D. T.; Brown, E. K.; Trulove, P. C. Development of a surrogate mixture for Algal-based hydrotreated renewable diesel. Energy Fuels 2013, 27, 954−961. (5) Luning Prak, D. J.; Jones, M. H.; Trulove, P. C.; McDaniel, A. M.; Dickerson, T.; Cowart, J. Physical and Chemical Analysis of Alcoholto-Jet (ATJ) Fuel and Development of Surrogate Fuel Mixtures. Energy Fuels 2015, 29, 3760−3769. (6) Mueller, C. J.; Cannella, W. J.; Bruno, T. J.; Bunting, B.; Dettman, H. D.; Franz, J. A.; Huber, M. L.; Natarajan, M.; Pitz, W. J.; Ratcliff, M. A.; Wright, K. Methodology for Formulating Diesel Surrogate Fuels with Accurate Compositional, Ignition-quality, and volatility characteristics. Energy Fuels 2012, 26, 4277−4284. (7) Xiao, G.; Zhang, Y.; Lang, J. Kinetic modeling study of the ignition process of homogeneous charge compression ignition engine fueled with three-component diesel surrogate. Ind. Eng. Chem. Res. 2013, 52, 3732−3741. (8) Ahmed, A.; Goteng, G.; Shankar, V. S. B.; Al-Qurashi, K.; Roberts, W. L.; Sarathy, S. M. A computational methodology for formulating gasoline surrogate fuels with accurate physical and chemical properties. Fuel 2015, 143, 290−300. (9) Dryer, F. L.; Jahangirian, S.; Dooley, S.; Won, S. H.; Heyne, J.; Iyer, V. R.; Litzinger, T. A.; Santoro, R. J. Emulating the combustion behavior of real jet aviation fuels by surrogate mixtures of hydrocarbon fuel blends: Implications for science and engineering. Energy Fuels 2014, 28, 3474−3485. (10) Kim, D.; Martz, J.; Voili, A. A surrogate for emulating the physical and chemical properties of conventional jet fuel. Combust. Flame 2014, 161, 1489−1498. (11) Huber, M. L.; Lemmon, E. W.; Bruno, T. J. Surrogate Mixture Models for the Thermophysical Properties of Aviation Fuel Jet-A. Energy Fuels 2010, 24, 3565−3571. (12) Dooley, S.; Won, S. H.; Chaos, M.; Heyne, J.; Ju, Y. G.; Dryer, F. L.; Kumar, K.; Sung, C. J.; Wang, H. W.; Oehlschlaeger, M. A.; Santoro, R. J.; Litzinger, T. A. A jet fuel surrogate formulated by real fuel properties. Combust. Flame 2010, 157, 2343−2349. (13) Huber, M. L.; Lemmon, E. W.; Diky, V.; Smith, B. L.; Bruno, T. J. Chemical Authentic Surrogate Mixture Model for the Thermophysical Properties of a Coal-Derived Fuel. Energy Fuels 2008, 22, 3249− 3257. (14) Mueller, C. J.; Cannella, W. J.; Bays, T.; Bruno, T. J.; Defabio, K.; Dettman, H. D.; Gieleciak, R. M.; Huber, M. L.; Kweon, C.-B.; McConnell.; et al. Diesel surrogate fuels for engine testing and chemical-kinetic modeling: composition and properties. Energy Fuels 2016, 30, 1445−1461. (15) Performance Specif ication Fuel, Naval Distillate, Military Specification MIL-PRF-16884L, Department of Defense: Washington, DC, Oct 23, 2006. (16) Ra, Y.; Reitz, R. D. The application of a multicomponent droplet vaporization model to gasoline injection engines. Int. J. Engine Res. 2003, 4, 193−218. (17) Pandey, R. K.; Rehman, A.; Sarviya, R. M. Impact of alternative fuel properties on fuel spray behavior and atomization. Renewable Sustainable Energy Rev. 2012, 16, 1762−1778. (18) Manin, J.; Bardi, M.; Pickett, L. M.; Dahms, R. N.; Oefelein, J. C. Microscopic investigation of the atomization and mixing processes of diesel sprays injected into high pressure and temperature environments. Fuel 2014, 134, 531−543.

comparison. As can be seen from the data in Table 12, the surface tensions and flash points increase as the mole fraction of 1,2,3,4-tetrahydronaphthalene increases. No mixtures match the surface tension or flash point of HDCD. The surface tension of an HDCD fuel was reported to be 29.9 ± 0.2 mN· m−2 at room temperature.1 This value falls slightly below the surface tension value of pure trans-decalin, 30.5 ± 0.2 mN·m−2. The flash point of HDCD was reported to be 350.15 K,1 which is higher than the value for 1,2,3,4-tetrahydronaphthelene, 347.7 K. The 5-butyl-1,2,3,4-tetrahydro-naphthalene and 3,3′dimethyl-1,1′biphenyl that were mentioned above to increase viscosity have estimated flashpoints of 394.15 and 395 K, respectively.47 They could be added to raise the flash point of the surrogate to values closer to that of HDCD. No data were found for surface tensions, so it is unclear how their addition would impact the surface tension of a surrogate mixture.

5. CONCLUSIONS In this work, the physical properties of mixtures of 1,2,3,4tetrahydronaphthalene and trans-decahydronaphthalene were measured. Second-order polynomials were used to fit the density and speed of sound data as a function of mole fraction of trans-decahydronaphthalene. The excess molar volumes were not statistically different from zero. Viscosity values of the mixtures at each temperature were well modeled using the McAllister three-body model. The viscosity values of the mixtures were lower than those of the individual components. Mixtures with mass fractions of 1,2,3,4-tetrahydronaphthalene in trans-decahydronaphthalene between 0.3000 and 0.5000 were able to match the density, speed of sound, and bulk modulus of hydrodepolymerized cellulosic diesel (HDCD) fuel. No mixtures, however, matched the viscosity, flash point, and surface tension of the HDCD. The use of two-component mixtures of 1,2,3,4-tetrahydronaphthalene and trans-decahydronaphthalene as surrogate mixtures for HDCD depends on how sensitive the combustion process is to variations in the various physical properties. If it is more sensitive to those properties for which a match between the mixtures and the HDCD is found, then a mixture could be used as a surrogate for HDCD. If not, either a different mixture or a more complex mixture needs to be formulated. Other compounds whose structures are similar to those in hydrotreated pyrolytic lignins, such as 5-butyl-1,2,3,4-tetrahydro-naphthalene and 3,3′-dimethyl-1,1′biphenyl, could be added to increase the viscosity and flashpoint of a surrogate mixture to help more closely match the values reported for HDCD.

■

AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Tel.: (410) 293-6339. Fax: (410) 2932218. Funding

This work was funded by the Office of Naval Research and a Kinnear Fellowship awarded to DJLP. Notes

The authors declare no competing financial interest.

■

REFERENCES

(1) Bermudez, E., McDaniel, A., Dickerson, T., Luning Prak, D., Hamilton, L., Cowart, J. Start-up and Steady-state performance of a new renewable hydro-processed depolymerized cellulosic diesel (HDCD) fuel in multiple diesel engines. Proceedings of the ASME H



Article

(19) Lee, Y.; Huh, K. Y. Numerical study on spray and combustion characteristics of diesel and soy-based biodiesel in a CI engine. Fuel 2013, 113, 537−545. (20) Boehman, A. L.; Morris, D.; Szybist, J. The impact of the bulk modulus of diesel fuels on fuel injection timing. Energy Fuels 2004, 18, 1877−1882. (21) Fortin, T. J.; Laesecke, A.; Freund, M.; Outcalt, S. Advanced calibration, adjustment, and operation of a density and sound speed analyzer. J. Chem. Thermodyn. 2013, 57, 276−285. (22) Luning Prak, D. J.; Morris, R. E.; Cowart, J. S.; Hamilton, L. J.; Trulove, P. C. Density, viscosity, speed of sound, bulk modulus, surface tension, and flash point of Direct Sugar to Hydrocarbon Diesel (DSH-76) and binary mixtures of n-hexadecane and 2,2,4,6,6pentamethylheptane. J. Chem. Eng. Data 2013, 58, 3536−3544. (23) Luning Prak, D. J.; Alexandre, S. M.; Cowart, J. S.; Trulove, P. C. Density, viscosity, speed of sound, bulk modulus, surface tension, and flash point of n-dodecane with 2,2,4,6,6-pentamethylheptane and 2,2,4,4,6,8,8-heptamethylnonane. J. Chem. Eng. Data 2014, 59, 1334− 1346. (24) Luning Prak, D. J.; Trulove, P. C.; Cowart, J. S. Density, viscosity, speed of sound, surface tension, and flash point of binary mixtures of n-hexadecane and 2,2,4,4,6,8,8-heptamethylnonane and of algal-based hydrotreated renewable diesel. J. Chem. Eng. Data 2013, 58, 920−926. (25) Luning Prak, D. J.; Jones, M. H.; Cowart, J. S.; Trulove, P. C. Density, viscosity, speed ofsound, bulk modulus, surface tension, and flash point of binary mixtures of 2,2,4,6,6-pentamethylheptane and 2,2,4,4,6,8,8-heptamethylnonane at (293.15 to 373.15) K and 0.1 MPa and comparisons with alcohol-to-jet fuel. J. Chem. Eng. Data 2015, 60, 1157−1165. (26) Luning Prak, D. J.; Cowart, J. S.; Trulove, P. C. Density, Viscosity, speed of sound, bulk modulus, surface tension, and flash point of binary mixtures of bicyclohexyl and 1,2,3,4-tetrahydronaphthalene or trans-decahydronaphthalene at (293.15 to 373.15) K and 0.1 MPa. J. Chem. Eng. Data 2016, 61, 650−661. (27) Chirico, R. D.; Frenkel, M.; Magee, J. W.; Diky, V.; Muzny, C. D.; Kazakov, A. F.; Kroenlein, K.; Abdulagatov, I.; Hardin, G. R.; Acree, W. E.; et al. Improvement of Quality in Publication of Experimental Thermophysical Property Data: Challenges, Assessment Tools, Global Implementation, and Online Support. J. Chem. Eng. Data 2013, 58, 2699−2716. (28) Harris, Daniel C. Quantitative Chemical Analysis, 8th ed.; W.H. Freeman and Company: NY, 2010. (29) Friend, D. G.; Waters, R. L. Certificate Standard Reference Material 211d, Toluene liquid density-extended range; National Institute of Standards and Technology: Gaithersburg, MD, 2009. (30) Luning Prak, D. J.; McDaniel, A. M.; Cowart, J. S.; Trulove, P. C. Density, viscosity, speed of sound, bulk modulus, surface tension, and flash point of binary mixtures of n-hexadecane + ethylbenzene or + toluene at (293.15 to 373.15) K and 0.1 MPa. J. Chem. Eng. Data 2014, 59, 3571−3585. (31) Yu, C.-H.; Tsai, F.-N. Excess volumes of tetralin + cyclohexane, + hexane, or + hexanol at 298.15 and 308.15 K. J. Chem. Eng. Data 1994, 39, 125−126. (32) Nascimento, F. P.; Mehl, A.; Ribas, D. C.; Paredes, M. L. L.; Costa, A. L. H. Experimental high pressure speed of sound and density of (tetralin+n-decane) and (tetralin + hexadecane) systems and thermodynamic modeling. J. Chem. Thermodyn. 2015, 81, 77−88. (33) Chi, H.; Li, G.; Guo, Y.; Xu, L.; Fang, W. Excess molar volume along with viscosity, flash point and refractive index of binary mixtures of cis-decalin or trans-decalin with C9 to C11 alkanes. J. Chem. Eng. Data 2013, 58, 2224−2232. (34) Gomez-Ibanez, J. D.; Wang, T. C. The excess volume of binary mixtures of trans-decalin with cyclohexane and with n-alkanes. J. Phys. Chem. 1966, 70, 391−395. (35) Shiohama, Y.; Ogawa, H.; Murakami, S.; Fujihara, I. Excess thermodynamic properties of (cis-decalin or trans-decalin + cyclohexane or methylcyclohexane or cyclooctane. J. Chem. Thermodyn. 1988, 20, 1307−1314.

(36) Bird, L. H.; Daly, E. F. Viscosity in some binary liquid systems. Trans. Faraday Soc. 1939, 35, 588−592. (37) Papaioannou, D.; Evangelou, T.; Panayiotou, C. Dynamic viscosity of multicomponent liquid mixtures. J. Chem. Eng. Data 1991, 36, 43−46. (38) Korsten, H. Viscosity of liquid hydrocarbons and their mixtures. AIChE J. 2001, 47, 453−462. (39) McAllister, R. A. The viscosity of liquid mixtures. AIChE J. 1960, 6, 427−431. (40) Gonzalez, R.; Dominguez, A.; Tojo, J.; Cores, R. Dynamic viscosities of 2-pentanol with alkanes (octane, decane, and dodecane) at three temperatures T = (293.15, 298.15, and 303.15) K. New UNIFAC-VISCO interaction parameters. J. Chem. Eng. Data 2004, 49, 1225−1230. (41) Al-Kandary, J. A.; Al-Jimaz, A. S.; Abdul-Latif, A.-H. M. Densities, viscosities, and refractive indices of binary mixtures of anisole with benzene, methylbenzene, ethylbenzene, propylbenzene, and butylbenzene at (294.15 and 303.15)K. J. Chem. Eng. Data 2006, 51, 99−103. (42) Cronauer, D. C.; Rothfus, R. R.; Kermode, R. I. Viscosity and density of the ternary liquid system acetone-benzene-ethylene dichloride. J. Chem. Eng. Data 1965, 10, 131−133. (43) Martins, R. J.; de M. Cardoso, M. J. E.; Barcia, O. E. Corrrelations: Excess Gibbs Free energy model for calculating the viscosity of binary liquid mixtures. Ind. Eng. Chem. Res. 2000, 39, 849− 854. (44) Dey, R.; Harshavardhan, A.; Verma, S. Viscometric investigation of binary, ternary, and quaternary liquid mixtures: Comparative evaluation of correlative and predictive models. J. Mol. Liq. 2015, 211, 686−694. (45) Wohlfarth, C. Viscosity of Pure Organic Liquids and Binary Liquid Mixtures; Landolt-Börnstein Numerical Data and Functional Relationships in Science and Technology, Group IV, Physical Chemistry, Supplement IV; Lechner, M. D., Ed.; Springer: Berlin, Germany, 2002; Vol. 18B. (46) ACD/Labs. Advanced Development Software V11.02; ACD/ Labs: Tonronto, Ontario, Canada (accessed via SciFinder scholar on 23 February 2016 https://scifinder.cas.org/scifinder/view/scifinder/ scifinderExplore.jsf). (47) SciFinder scholar. https://scifinder.cas.org/scifinder/view/ scifinder/scifinderExplore.jsf (accessed on 23 February 2016). (48) NIST Standard Reference Database 69: NIST Chemistry WebBook. http://webbook.nist.gov/chemistry (accessed 23 February 2016). (49) Chylinski, K.; Stryjek, R. Excess volumes of 1,2,3,4tetrahydronaphthalene + trans-, and + cis -bicyclo[4.4.4]decane and of quinoline + trans- and + cis-bicyclo[4.4.0] decane, + 1,2,3,4tetrahydronaphthalene, and + n-hexadecane. J. Chem. Thermodyn. 1982, 14, 1115−1118.

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