Density, Viscosity, Speed of Sound, and Bulk Modulus of Methyl

Article pubs.acs.org/jced

Density, Viscosity, Speed of Sound, and Bulk Modulus of Methyl Alkanes, Dimethyl Alkanes, and Hydrotreated Renewable Fuels Dianne J. Luning Prak,* Eva K. Brown, and Paul C. Trulove Chemistry Department, United States Naval Academy, 572M Holloway Road, Annapolis, Maryland 21402, United States ABSTRACT: The density, viscosity, and speed of sound were measured in this work for pure component branched alkanes (2-methyloctane, 4-methyloctane, 2methylnonane, 2-methyldecane, 3-methylundecane, 2-methylpentadecane, 7methylhexadecane, 3,6-dimethyloctane, and 3,5-dimethylheptane) commonly found in hydrotreated renewable fuels (HRFs) and for HRFs from tallow, camelina oil, and algae and waste cooking oil blended 50/50 with petroleum diesel. The density and viscosity were measured at temperatures from (283.15 to 373.15) K and ranged from (661 to 788) kg·m−3 for density and (0.261 to 5.36) mPa·s for viscosity. Speed of sound data were measured at temperatures from (283.15 to 323.15) K and spanned from (1081 to 1393) m·s−1. The bulk modulus was calculated from the density and speed of sound data, and its values varied from (809 to 1527) MPa. All values increased as the carbon chain length on the alkane increased. All physical property values for the HRFs fell between those measured for individual pure component branched alkanes, providing property data for the development of surrogate mixtures for these renewable fuels.

1. INTRODUCTION Volatility in petroleum prices has been a strong driving force in the development of alternative fuels from abundant and

To gain a better understanding of the utilization of these types of fuels in already existing military and commercial engines, numerical modeling of the combustion process is being employed. As with many fuels, modeling and engine testing can be greatly simplified if a surrogate mixture, containing few components with well-defined physical and chemical properties, can be found that matches the fuel’s properties. Surrogate mixtures for rocket propellants, aviation fuels, coal-derived liquid fuel, petroleum diesel fuel, biodiesel, and algal-based HRF have contained various combinations of aromatic hydrocarbons, cycloalkanes, n-alkanes, and branched alkanes.6,8,9−19,21−23 In one approach to surrogate development, a list of individual chemicals, called a surrogate palette, with known physical and transport properties is made. Using pure component properties from the available palette as a starting point, a surrogate mixture is determined. Through physical property optimization, the mixture quantities are refined until the properties of the surrogate closely match those of the target fuel. Properties commonly used for this type of surrogate development include density, viscosity, speed of sound, and distillation curve.6,9,11,14,16 Density and viscosity are also among the parameters needed to simulate the vaporization of multicomponent droplets in a direct injection gasoline engine.24 From density and speed of sound measurements, bulk modulus can be calculated, an important parameter for more accurate modeling of fuel injection time.6,25 In the palette of chemicals used in surrogate development, the most commonly used branched alkanes have been

Table 1. Sample Information

a

chemical

source

mole fraction purity

2-methyloctane 4-methyloctane 2-methylnonane 2-methyldecane 3-methylundecane 3,5-dimethylheptane 3,6-dimethyloctane 2-methylpentadecane 7-methylhexadecane n-hexadecane

TCI Chemicalsb TCI Chemicalsb TCI Chemicalsb/Aldrichc ChemSampCod TCI Chemicalsb ChemSampCod ChemSampCod MP Biomedicalsd MP Biomedicalsd Aldrichd

> 0.99 > 0.99 > 0.99 0.994 0.98 0.985 0.987 > 0.94 > 0.98 > 0.99

analysis methoda GC GC GC GC GC GC GC GC GC GC

Gas−liquid chromatography. bJapan. cNorway. dUnited States.

renewable natural resources including plant sources, such as camelina and algae, as well as agricultural and commercial byproducts such as tallow or waste cooking oil. One variety of alternative fuel with particular promise for military applications, due to close matching of military fuel specifications, are hydrotreated renewable fuels (HRFs), produced by reacting extracted lipids or triglycerides with hydrogen over a catalyst to remove oxygen, other heteroatoms, and to saturate the double bonds.1 The resulting fuels consist predominantly of linear, monomethyl and dimethyl alkanes.2 These HRF fuels have been tested in laboratory engines as well as in U.S. Navy fleet demonstrations.3−7 This article not subject to U.S. Copyright. Published 2013 by the American Chemical Society

Received: March 21, 2013 Accepted: June 12, 2013 Published: June 25, 2013 2065

dx.doi.org/10.1021/je400274f | J. Chem. Eng. Data 2013, 58, 2065−2075

SVM DSA SVM DSA SVM DSA SVM DSA SVM DSA SVM DSA SVM DSA SVM DSA SVM DSA SVM DSA SVM DSA SVM DSA

3,5-dimethyl heptane

2066

734.1 734.0 723.2 ± 0.4 723.2 727.5 727.6 746.6 746.6 ± 0.4 734.7 734.5 745.7 745.8 758.6 758.3 782.2 ± 0.4 781.8 787.6 787.6 771.6 771.4 760.9 760.9 784.7 784.6

T = 283.15 K 726.3 726.2 715.3 715.4 719.7 719.8 738.9 738.9 ± 0.4 727.1 726.9 738.3 738.4 751.3 751.1 775.0 774.9 780.7 780.7 764.4 764.3 753.6 753.7 777.7 777.7

T = 293.15 K 718.4 718.4 707.4 707.6 711.7 711.9 731.1 731.2 ± 0.4 719.4 719.3 730.9 730.9 744.0 743.9 768.0 767.9 773.8 773.9 757.3 757.2 746.3 746.4 770.8 770.8

T = 303.15 K 710.5 710.5 699.4 699.6 703.7 703.9 723.3 723.5 ± 0.5 711.7 711.6 723.2 723.5 736.7 736.6 761.0 761.0 766.9 767.0 750.1 750.0 738.9 739.1 763.9 763.9

T = 313.15 K 702.5 702.5 691.4 691.6 ± 0.3 695.7 695.9 715.5 715.7 ± 0.5 703.9 703.9 715.7 715.9 729.3 729.3 754.0 754.1 760.0 760.2 742.8 742.9 731.5 731.7 ± 0.3 756.9 756.9

T = 323.15 K

749.9

724.1

735.6

753.1

747.0

721.9

708.1

696.0

707.6

687.5

742.9

716.6

728.3

746.2

740.0

714.4

700.5

688.1

699.6

679.3

675.1

686.3 ± 0.4

694.5 ± 0.4 683.3

T = 343.15 K

T = 333.15 K

735.9

709.1

721.0

739.3

733.0

707.0

692.8

680.2

691.5

671.0

666.7

678.0

T = 353.15 K

728.8

701.5

713.6

732.4

726.0

699.4

684.9

672.1

683.3

662.5

658.2

669.7 ± 0.4

T = 363.15 K

721.8

693.9

706.2

725.4

718.9

691.9

677.0 ± 0.4

664.0

674.9 ± 0.4

653.9

649.7 ± 0.4

661.2

T = 373.15 K

a Standard uncertainties u are u(T) = 0.01 K, and combined expanded uncertainties Uc are Uc(ρ) ≤ 0.3 kg·m−3 for the SVM 3000 and Uc(ρ) ≤ 0.2 kg·m−3 for the DSA 5000 unless otherwise indicated by the “ ± ” (level of confidence = 0.95, k ≈ 2).

HRF-76

HRF-tallow

HRF-camelina

7-methyl hexadecane

2-methyl pentadecane

3-methyl undecane

2-methyl decane

2-methyl nonane

3,6-dimethyl octane

4-methyl octane

2-methyl octane

inst.

compound

Table 2. Experimental Valuesa of Density ρ (kg·m−3) for Methylalkanes, Dimethylalkanes, and Hydrotreated Renewable Fuels from T = (283 to 373) K at 0.1 MPa

Journal of Chemical & Engineering Data Article


Journal of Chemical & Engineering Data

Article

isooctane and isocetane,6,10,13,16,19 with only a few examples including mono and dimethyl alkanes.9,11,23 To successfully develop surrogate mixtures for HRFs which can contain monomethyl and dimethyl alkanes up to one-half of their composition,26 the physical properties of the individual monomethyl and dimethyl alkanes must be known, so they can be added to the palette of chemicals. For some of the branched components commonly found in HRFs, the physical property data required for surrogate development are limited and must be measured over a range of temperatures. Some of the branched alkanes isolated from HRFs include 2,5dimethylheptane, 3,5-dimethylheptane, 3-methyloctane, 4methyloctane, 2,5-dimethyloctane, 3,6-dimethyloctane, 2,6dimethyloctane, 2-methylnonane, 3-methylnonane, 2,5-dimethylnonane, 3-methyldecane, 2-methyldecane, 3-methylundecane, 5-methylundecane, 2-methylpentadecane, 4-methylhexadecane, 7-methylhexadecane, 2-methylheptadecane, and 3methyltetradecane.2,26 In this work, the density, dynamic and kinematic viscosity, and speed of sound were measured for nine monomethyl and dimethyl alkanes (Table 1), for HRFs derived from camelina and tallow, and for a blend of HRF fuel with petroleum diesel (50/50 HRF from algae and cooking oil/petroleum diesel) used by the U.S. Navy in a Fleet exercise in 2012. The goal of this work was to provide physical property data of individual components over a range of temperatures at atmospheric conditions. With these properties, these methyl alkanes can be added to the palette of potential chemicals that can be used to develop surrogate mixtures for HRFs.

Stabinger Viscometer. This standard has viscosity values that range from (1.1512 to 4.673) mm2·s−1 and density values that vary from (806.3 to 862.0) kg·m−3. If the density deviated by more than 0.1 % from the reference value and if the viscosity deviated by more than 1 % from the reference value, then the instrument was cleaned and retested. For lower viscosity and density, octane and decane standards that span a density range of (635.5 to 730.4) kg·m−3 and viscosity range of (0.446 to 1.25) mm2·s−1 were analyzed. Duplicate or triplicate samples of each methyl alkane were measured at 10 temperatures between (283.15 and 373.15) K, and these replicates were used to determine the precision of the measurement. The DSA 5000 analyzer was checked before use with degassed distilled water and recalibrated if it failed the check, as specified by the manufacturer. Duplicate samples of each individual liquid or liquid mixture were measured at five temperatures between (283.15 and 323.15) K, and these duplicates were used to determine the precision of the measurement. The uncertainties in density, viscosity, and speed of sound were calculated as combined expanded uncertainties, which are the standard deviations of the measurements, multiplied by 2. The coverage factor of 2 yields a 95 % confidence interval.

4. RESULTS 4.1. Density. The density values for the monomethyl and dimethyl alkanes are given in Table 2 for both measurement Table 3. Parameters for eq 2, ρ/kg·m−3 = A T/K + B, that Relates Density, ρ/kg·m−3 to Temperature for T = (283 to 373) Ka

2. MATERIALS The pure organic compounds tested were among those found in HRF fuels: 2-methyloctane, 4-methyloctane, 2-methylnonane, 2-methyldecane, 3-methylundecane, 2-methylpentadecane, 7-methylhexadecane, 3,6-dimethyloctane, and 3,5-dimethylheptane. In addition, n-hexadecane was used as a reference for speed of sound measurements. Sample information is found in Table 1. The hydrotreated renewable jet fuels tested were derived from camelina (HRF-camelina) and tallow oil (HRFtallow). The camelina-based HRF was provided by Naval Fuels and Lubricants Cross Function Team at Patuxent River, Maryland (PAX River) and the tallow-based HRF was provided by the Air Force Research Lab at Wright Patterson Air Force Base, Ohio. The fuel used in the U.S. fleet demonstration in 2012 (HRF from algae and vegetable oil mixed 50/50 with petroleum diesel) (HRF-76) was also provided by PAX River. All of these HRFs were processed by Honeywell UOP, which utilizes a two-stage process to transform the plant oils to jet or diesel fuel. The process first removes the heteroatoms and saturates the double bonds using a proprietary catalyst, and then it isomerizes and selectively cracks the resulting products to produce the lower molecular weight jet fuels such as HRFcamelina and HRF-tallow and higher molecular weight diesel fuels such as those found in HRF-76.

A 3,5-dimethyl heptane 2-methyl octane 4-methyl octane 3,6-dimethyl octane 2-methyl nonane 2-methyl decane 3-methyl undecane 2-methyl pentadecane 7-methyl hexadecane HRF-camelina HRF-tallow HRF-76 a

−0.8094 −0.8157 −0.8163 −0.7946 −0.7853 −0.7627 −0.7408 −0.7018 −0.6914 −0.7259 −0.7444 −0.6989

± ± ± ± ± ± ± ± ± ± ± ±

R2

B 0.0084 0.0096 0.0093 0.0036 0.0065 0.0055 0.0037 0.0014 0.0007 0.0033 0.0041 0.0019

963.7 954.6 959.1 972.0 957.4 962.0 968.5 980.8 983.2 977.3 971.9 982.7

± ± ± ± ± ± ± ± ± ± ± ±

2.8 3.2 3.1 2.7 2.2 1.8 1.2 0.5 0.5 1.1 1.4 0.6

0.9998 0.9998 0.9998 0.9998 0.9999 0.9999 0.9999 0.9999 0.9999 0.9999 0.9999 0.9999

Error bars are the 95 % confidence interval.

systems for temperatures from (283 to 373) K. The values from the two measurement systems agree with each other within the combined expanded uncertainties of each system. As the carbon chain length on the 2-methyl alkane molecule increases, the density increases as has been seen with straight chain hydrocarbons. When comparing the 2-methyl alkanes to their straight chain isomers, the 2-methyl isomers have a higher density. For example at 283.15 K, the density of 2-methyl octane, 723.2 kg·m−3, is higher than that of nonane, 717.7 kg·m−3,27 while the density of 2-methyl decane, 745.8 kg·m−3, is higher than that of undecane, 740.2 kg·m−3.27 These two additional carbons on the molecular structure, cause an increase of approximately 22.5 kg·m−3 for both the linear and branched alkane. It is important to note that density is not a linear function of carbon number over a wide a range of carbon numbers. The dimethyl alkanes have an even higher density than their straight chain isomers. At 283.15 K, the density of

3. METHODS An SVM 3000 Stabinger Viscometer (Anton Paar) was used to measure the density and viscosity of methyl alkanes, while a DSA 5000 Density and Sound Analyzer (Anton Paar) was used to measure the speed of sound and also density. A certified viscosity reference standard (Standard S3, Cannon Instrument Company) was used to test the accuracy of the SVM 3000 2067



Article

Figure 4. Density of 4-methyloctane: □, this study; ■, ref 45; ◆, ref 29; ◇, ref 37; Δ, ref 30. Density of 2-methylpentadecane: ○, this study; ▲, ref 32. Error bars, which are the combined expanded uncertainties with 0.95 level of confidence (k ≈ 2), are smaller than symbols. Lines shown are linear fits to eq 2 with the coefficients in Table 3.

Figure 1. Density of 2-methyloctane: □, this study; ×, ref 35; ●, ref 40; ◇, ref 37; ■, ref 36. Density of 2-methylnonane: ○, this study; +, ref 35; ◆, ref 41; Δ, ref 28; ▲, ref 42. Error bars, which are the combined expanded uncertainties with 0.95 level of confidence (k ≈ 2), are smaller than symbols. Lines shown are linear fits to eq 2 with the coefficients in Table 3.

Figure 2. Density of 3,5-dimethylheptane: □, this study; ◇, ref 39; Δ, ref 37. Density of 3,6-dimethyloctane: ○, this study; ×, ref 33; ◆, ref 34; +, ref 43; ▲, ref 37. Error bars, which are the combined expanded uncertainties with 0.95 level of confidence (k ≈ 2), are smaller than symbols. Lines shown are linear fits to eq 2 with the coefficients in Table 3.

Figure 5. Density of HRF-76, □; HRF-tallow, Δ; HRF-camelina,○; and 7-methylhexadecane, ▲. Error bars, which are the combined expanded uncertainties with 0.95 level of confidence (k ≈ 2), are smaller than symbols. Lines shown are linear fits to eq 2 with the coefficients in Table 3.

Table 4. Comparison of Density ρ (kg·m−3) Values with Literature Values at 293.15 K ρ/kg·m−3 methyl and dimethyl alkanes

Figure 3. Density of 2-methyldecane: □, this study; Δ, ref 38; ■, ref 37. Density of 3-methylundecane: ○, this study; ◇, ref 37; x, ref 44; ◆, ref 31; ―, ref 32. Error bars, which are the combined expanded uncertainties with 0.95 level of confidence (k ≈ 2), are smaller than symbols. Lines shown are linear fits to eq 2 with the coefficients in Table 3.

2068

(this work)

(literature)

2-methyl octane

715.3 ± 0.3

4-methyl octane

719.7 ± 0.3

2-methyl nonane 2-methyl decane

727.1 ± 0.3 738.3 ± 0.3

3-methyl undecane

751.3 ± 0.3

2-methyl pentadecane 3,5-dimethyl heptane 3,6-dimethyl octane

775.0 ± 0.3 726.3 ± 0.2 738.9 ± 0.2

713.4635 71736 720.1730 721.1 ± 2.229 72728 736.837 742.238 7.5 × 10232 751.6 ± 0.731 771.4 ± 0.732 722.5 ± 0.239 734.2 ± 1.033 740.2 ± 1.034


2069

a

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 η/mPa·s ν/mm2·s−1 η/mPa·s ν/mm2·s−1

0.792 ± 0.008 1.08 ± 0.01 0.776 ± 0.008 1.07 ± 0.01 0.719 ± 0.01 0.988 ± 0.02 0.988 ± 0.01 1.32 ± 0.01 1.037 ± 0.01 1.41 ± 0.01 1.37 ± 0.01 1.84 ± 0.01 1.73 ± 0.01 2.28 ± 0.07 4.60 ± 0.13 5.88 ± 0.16 5.36 ± 0.26 6.80 ± 0.33 2.49 ± 0.02 3.22 ± 0.03 1.72 ± 0.02 2.25 ± 0.02 4.44 ± 0.04 5.65 ± 0.06

T = 283.15 K 0.688 ± 0.007 0.947 ± 0.009 0.676 ± 0.007 0.944 ± 0.009 0.628 ± 0.01 0.872 ± 0.01 0.846 ± 0.008 1.14 ± 0.01 0.887 ± 0.009 1.22 ± 0.01 1.15 ± 0.02 1.56 ± 0.02 1.43 ± 0.01 1.90 ± 0.02 3.52 ± 0.11 4.54 ± 0.14 4.00 ± 0.20 5.13 ± 0.26 1.97 ± 0.02 2.58 ± 0.03 1.41 ± 0.01 1.87 ± 0.02 3.36 ± 0.04 4.32 ± 0.04

T = 293.15 K 0.604 ± 0.006 0.840 ± 0.008 0.594 ± 0.006 0.839 ± 0.008 0.554 ± 0.01 0.778 ± 0.01 0.733 ± 0.007 1.00 ± 0.01 0.768 ± 0.008 1.07 ± 0.01 0.977 ± 0.01 1.34 ± 0.01 1.20 ± 0.01 1.601 ± 0.02 2.77 ± 0.07 3.61 ± 0.09 3.09 ± 0.14 3.99 ± 0.18 1.60 ± 0.002 2.12 ± 0.02 1.18 ± 0.01 1.57 ± 0.02 2.63 ± 0.03 3.41 ± 0.03

T = 303.15 K 0.508 ± 0.005 0.714 ± 0.007 0.499 ± 0.005 0.714 ± 0.007 0.453 ± 0.04 0.657 ± 0.07 0.620 ± 0.006 0.857 ± 0.01 0.653 ± 0.007 0.917 ± 0.009 0.830 ± 0.008 1.15 ± 0.01 1.01 ± 0.01 1.38 ± 0.01 2.24 ± 0.07 2.95 ± 0.09 2.47 ± 0.11 3.22 ± 0.15 1.33 ± 0.01 1.78 ± 0.02 0.992 ± 0.01 1.34 ± 0.01 2.13 ± 0.02 2.78 ± 0.03

T = 313.15 K 0.477 ± 0.005 0.678 ± 0.007 0.470 ± 0.005 0.680 ± 0.007 0.441 ± 0.01 0.633 ± 0.01 0.568 ± 0.006 0.793 ± 0.008 0.595 ± 0.006 0.844 ± 0.008 0.736 ± 0.007 1.03 ± 0.01 0.883 ± 0.009 1.21 ± 0.01 1.85 ± 0.05 2.45 ± 0.07 2.00 ± 0.09 2.63 ± 0.12 1.13 ± 0.01 1.52 ± 0.02 0.862 ± 0.009 1.18 ± 0.01 1.74 ± 0.02 2.30 ± 0.02

T = 323.15 K 0.428 ± 0.004 0.616 ± 0.006 0.422 ± 0.004 0.618 ± 0.006 0.397 ± 0.01 0.577 ± 0.01 0.506 ± 0.005 0.714 ± 0.007 0.529 ± 0.005 0.760 ± 0.008 0.647 ± 0.008 0.913 ± 0.01 0.771 ± 0.008 1.07 ± 0.01 1.55 ± 0.03 2.08 ± 0.04 1.66 ± 0.08 2.21 ± 0.10 0.969 ± 0.01 1.32 ± 0.01 0.752 ± 0.007 1.04 ± 0.01 1.46 ± 0.01 1.95 ± 0.02

T = 333.15 K 0.386 ± 0.004 0.562 ± 0.006 0.381 ± 0.004 0.564 ± 0.006 0.368 ± 0.03 0.541 ± 0.05 0.453 ± 0.004 0.648 ± 0.006 0.475 ± 0.005 0.689 ± 0.007 0.575 ± 0.008 0.822 ± 0.02 0.680 ± 0.007 0.952 ± 0.01 1.33 ± 0.02 1.79 ± 0.03 1.41 ± 0.06 1.89 ± 0.08 0.842 ± 0.008 1.16 ± 0.01 0.662 ± 0.007 0.924 ± 0.009 1.24 ± 0.01 1.67 ± 0.02

T = 343.15 K 0.350 ± 0.004 0.516 ± 0.005 0.345 ± 0.003 0.518 ± 0.005 0.329 ± 0.02 0.490 ± 0.03 0.409 ± 0.004 0.592 ± 0.006 0.428 ± 0.004 0.628 ± 0.006 0.514 ± 0.007 0.742 ± 0.01 0.605 ± 0.006 0.856 ± 0.009 1.14 ± 0.03 1.56 ± 0.03 1.21 ± 0.04 1.63 ± 0.06 0.739 ± 0.007 1.03 ± 0.01 0.588 ± 0.006 0.829 ± 0.008 1.07 ± 0.01 1.46 ± 0.02

T = 353.15 K

Standard uncertainty u is u(T) = 0.01 K, and combined expanded uncertainty, Uc with a level of confidence = 0.95, k ≈ 2 is shown as error bars for viscosity.

HRF-76

HRF-tallow

HRF-camelina

7-methyl hexadecane


3-methyl undecane

2-methyl decane

2-methyl nonane

3,6-dimethyl octane

4-methyl octane

2-methyl octane

3,5-dimethyl heptane

compound 0.319 ± 0.003 0.476 ± 0.009 0.315 ± 0.003 0.479 ± 0.005 0.294 ± 0.02 0.444 ± 0.03 0.372 ± 0.004 0.544 ± 0.005 0.388 ± 0.004 0.577 ± 0.006 0.464 ± 0.006 0.677 ± 0.008 0.543 ± 0.005 0.776 ± 0.008 1.00 ± 0.02 1.38 ± 0.02 1.05 ± 0.04 1.44 ± 0.04 0.656 ± 0.007 0.919 ± 0.009 0.527 ± 0.005 0.751 ± 0.008 0.937 ± 0.009 1.28 ± 0.01

T = 363.15 K

0.288 ± 0.003 0.444 ± 0.004 0.261 ± 0.02 0.398 ± 0.03 0.328 ± 0.003 0.49 ± 0.05 0.355 ± 0.004 0.534 ± 0.005 0.422 ± 0.005 0.622 ± 0.008 0.492 ± 0.005 0.710 ± 0.007 0.88 ± 0.01 1.23 ± 0.02 0.91 ± 0.026 1.25 ± 0.09 0.570 ± 0.006 0.828 ± 0.008 0.477 ± 0.005 0.687 ± 0.007 0.828 ± 0.008 1.15 ± 0.01

T = 373.15 K

Table 5. Experimental Valuesa of Dynamic Viscosity η (mPa·s) and Kinematic Viscosity ν (mm2·s−1) for Methylalkanes, Dimethylalkanes, and Hydrotreated Renewable Fuels from T = (283 to 373) K at 0.1 MPa

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Article

Figure 7. Viscosity of 4-methyloctane: ○, this study; 3-methylundecane: □, this study; ■, ref 47. Viscosity of 7-methylhexadecane: Δ, this study. Lines shown are fits to eq 2 with coefficients in Table 6. Error bars are the combined expanded uncertainties with 0.95 level of confidence (k ≈ 2).

Figure 6. Viscosity of 2-methyloctane: ○, this study; ■, ref 40. Viscosity of 2-methylnonane: □, this study; ◆, ref 28. Lines shown are fits to eq 2 with coefficients in Table 6. Error bars, which are the combined expanded uncertainties with 0.95 level of confidence (k ≈ 2), are smaller than symbols.

3,6-dimethyloctane, 746.6 kg·m−3, is much higher than that of decane, 730.1 kg·m−3.27 Density and temperature data were fit to ρ/kg·m−3 = AT /K + B

(1)

using the Microsoft Excel linear regression software in its Analysis Toolpak. The fitting parameters are given in Table 3 with all fits having an R2 > 0.999. These lines are shown on Figures 1 to 5. Comparisons of the measured values to those in the literature are shown in Figures 1 through 4. At 293.15 K, the density values of 2-methylnonane, 4-methyloctane, and 3methylundecane agree with literature values within the 95 % confidence interval, while the density values for 3,6dimethyloctane, 2-methyloctane, and 2-methyldecane fall between literature values (Table 4). Only the density values of 2-methylpentadecane and 3,5-dimethylheptane are higher than those reported in the 1950 synthesis papers of Petrov et al.32 and Levina et al.39 The density values of both HRF-camelina and HRF-tallow fall between those of 3-methylundecane and 2-methylpentadecane (Figures 3, 4, 5). These density values are much lower than the values of the HRF-76, which are between 2methylpentadecane and 7-methylhexadecane (Figures 4 and 5, respectively). The camelina and tallow-based fuels were

Figure 8. Viscosity of 3,6-dimethyloctane: ○, this study. Viscosity of 3,5-dimethylheptane: □, this study. Lines shown are fits to eq 2 with coefficients in Table 6. Error bars, which are the combined expanded uncertainties with 0.95 level of confidence (k ≈ 2), are smaller than symbols.

cracked from their original hydrocarbon mixture to produce jet fuels that have a lower density than diesel fuels, such as HRD76.

Table 6. Parameters for eq 2, η/mPa·s = A exp(BT−1/K−1), that Relates Dynamic Viscosity, η, to Temperature for T = (283 to 373) Ka 103·A 3,5-dimethyl heptane 2-methyl octane 4-methyl octane 3,6-dimethyl octane 2-methyl nonane 2-methyl decane 3-methyl undecane 2-methyl pentadecane 7-methyl hexadecane HRF-camelina HRF-tallow HRF-76 a

11 13 13 11 12 10 9.4 4.9 3.5 6.0 8.5 4.2

R2

B (7.8, 15) (11,15) (9.6,17) (10,13) (11, 14) (9.4, 11) (8.5, 10) (3.9,6.0) (2.7,4.5) (5.2, 6.8) (7.6, 9.5) (3.3, 5.3)

1220 1150 1140 1260 1250 1380 1470 1930 2060 1700 1500 1960

(1120, (1100, (1050, (1220, (1220, (1350, (1440, (1860, (1980, (1660, (1660, (1880,

1320) 1200) 1230) 1300) 1280) 1410) 1500) 1750) 2140) 1750) 1530) 2040)

0.9895 0.9976 0.9907 0.9985 0.9991 0.9994 0.9993 0.9980 0.9977 0.9989 0.9991 0.9976

Values in parentheses represent 95 % confidence interval. 2070



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Figure 9. Viscosity of 2-methylpentadecane: ○, this study; ■, ref 47. Viscosity of 2-methyldecane: □, this study; ●, ref 47. Viscosity of HRF-tallow, Δ, this study; HRF-camelina, ◊, this study; HRD-76, ▲, this study. Lines shown are fits to eq 2 with coefficients in Table 6. Error bars, which are the combined expanded uncertainties with 0.95 level of confidence (k ≈ 2), are smaller than symbols.

Figure 10. Speed of sound of n-hexadecane: ○, this study; ×, ref 51. Error bars, which are the combined expanded uncertainties with 0.95 level of confidence (k ≈ 2), are smaller than symbols.

Table 9. Parameters for eq 2: c/m·s−1 = AT/K + B, that Relates Speed of Sound c/m·s−1 to Temperature for T = (283 to 323) Ka

Table 7. Comparison of Viscosity η (mPa·s) Values with Literature Values at 293.15 K

A

η/mPa·s methyl and dimethyl alkanes 2-methyl octane 2-methyl nonane 2-methyl decane

3-methyl undecane


T/K

(this work)

(literature)

310.95 393.15 293 313 293.15 313.15 333.15 353.15 293.15 313.15 333.15 353.15 293.15 313.15 333.15 353.15

0.525 0.288 ± 0.003 0.887 ± 0.009 0.653 ± 0.007 1.15 ± 0.02 0.830 ± 0.008 0.647 ± 0.008 0.514 ± 0.007 1.43 ± 0.01 1.01 ± 0.01 0.771 ± 0.008 0.605 ± 0.006 3.52 ± 0.11 2.24 ± 0.07 1.55 ± 0.03 1.14 ± 0.03

0.52540 0.27940 0.872 ± 0.00428 0.659 ± 0.00328 1.10847 0.80847 0.62847 0.50147 1.38347 0.98947 0.75047 0.54147 3.54647 2.21447 1.55247 1.13347

3,5-dimethyl heptane 2-methyl octane 4-methyl octane 3,6-dimethyl octane 2-methyl nonane 2-methyl decane 3-methyl undecane 2-methyl pentadecane 7-methyl hexadecane HRF-camelina HRF-tallow HRF-76 a

−4.094 −4.026 −4.061 −4.016 −3.951 −3.865 −3.843 −3.679 −3.676 −3.818 −3.873 −3.719

± ± ± ± ± ± ± ± ± ± ± ±

R2

B 0.070 0.054 0.073 0.073 0.060 0.061 0.066 0.074 0.070 0.072 0.070 0.071

2404 2382 2417 2414 2390 2390 2418 2430 2432 2421 2415 2430

± ± ± ± ± ± ± ± ± ± ± ±

21 16 19 22 16 19 20 22 21 22 21 21

0.9999 0.9999 0.9999 0.9999 0.9999 0.9999 0.9999 0.9998 0.9998 0.9998 0.9999 0.9999

Error bars are the 95 % confidence interval.

4.2. Viscosity. The viscosity values for the mono and dimethylalkanes are given in Table 5 for temperatures ranging from (283 to 373) K. An empirical equation in the form46 η/mPa· s = A exp(BT −1/K−1)

(2)

Table 8. Experimental Valuesa of Speed of Sound Measurements c (m·s−1) for Methylalkanes, Dimethylalkanes, and Hydrotreated Renewable Fuels from T= (283 to 323) K at 0.1 MPa 3,5-dimethyl heptane 2-methyl octane 4-methyl octane 3,6-dimethyl octane 2-methyl nonane 2-methyl decane 3-methyl undecane 2-methyl pentadecane 7-methyl hexadecane HRF-camelina HRF-tallow HRF-76

T = 283.15 K

T = 293.15 K

T = 303.15 K

T = 313.15 K

T = 323.15 K

1245.1 1242.2 1254.9 1277.8 1271.4 1295.5 1330.2 1378.7 1392.5 1340.1 1319.4 1377.3

1203.3 1201.3 1213.0 1236.7 1231.1 1256.2 1291.0 1341.0 1354.9 1301.0 1279.8 1339.2

1162.0 1160.7 1171.6 1196.2 1191.3 1217.1 1252.2 1303.8 1317.7 1262.4 1240.7 1301.6

1121.3 1120.7 1130.8 1156.3 ± 0.6 1152.0 1178.8 1214.0 1267.3 1281.3 1224.6 1202.2 1264.8

1081.4 1081.2 1090.7 1117.2 1113.4 1141.0 1176.6 1231.6 1245.5 1187.4 1164.5 1228.6

Standard uncertainty u is u(T) = 0.01 K, and combined expanded uncertainty Uc is Uc(c) ≤ 0.5 m·s−1 unless otherwise indicated by the “ ± ” (level of confidence = 0.95, k ≈ 2). a

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temperature coefficient, B, of 2-methyloctane having a B value of 1150 K and 7-methylhexadecane (Figure 7) having a B value of 2060 K. Comparisons of the measured viscosity values to those in the literature are shown in Figures 6 to 9. For 2-methyloctane, 2methylnonane, and 2-methylpentadecane, the values agree with or are slightly higher than those reported in the literature as shown in Table 7. The data for 2-methyldecane, 3methylundecane, and 2-methylpentadecane come from a 1959 synthesis article by Terres et al.47 that does not report the error. If these measurements have a 2 % error, then they would match most of the values reported herein. As the carbon chain length on the 2-methyl alkane molecule increases, the viscosity increases as has been seen with straight chain hydrocarbons. When comparing the 2-methyl alkanes to their straight chain isomers, the 2-methyl isomers have viscosity values that are lower than their straight chain isomers for the lower molecular weight compounds but are the same for the higher molecular weight compounds. For example at 298.15 K, the viscosity of 2-methyl octane predicted by eq 2, 0.615 mPa·s, is lower than that of nonane, 0.6600 mPa·s,48 and the viscosity predicted for 2-methyl decane, 1.02 mPa·s, is lower than that of undecane, 1.0841 mPa·s .48 In contrast at 293.15 K, the viscosity of 2-methylpentadecane, 3.52 ± 0.11 mPa·s, is the same as that of n-hexadecane, 3.46 ± 0.04 mPa·s,49 and the viscosity of 7-methyl hexadecane, 4.00 ± 0.20 mPa·s is the same as that of n-heptadecane, 4.209 ± 0.008 mPa·s50 within the error of the measurements. The viscosity values of HRF-camelina and HRF-76 (Figure 9) fall between those of 3-methylundecane and 2-methylpentadecane, while the viscosity values of HRF-tallow (Figure 9) fall between those of 2-methyldecane and 3-methylundecane (Figure 7). 4.3. Speed of Sound and Bulk Modulus. The speed of sound values for the monomethyl and dimethylalkanes are given in Table 8 for temperatures from (283 to 323) K. Literature values are not available for these compounds. For comparison purposes, the instrument was used to measure the speed of sound of n-hexadecane. Figure 10 shows that the values measured for n-hexadecane match those reported by Outcalt et al.51 The speed of sound values for HRF-tallow fall between those of 2-methyldecane and 3-methylundecane, while the values for HRF-camelina and for HRF-76 fall between those of 3-methylundecane and 2-methylpentadecane. Speed of sound and temperature data were fit to

Figure 11. Speed of sound of 2-methyloctane, ◊; 2-methylnonane, ○; 2-methyldecane, ×; HRF -tallow, ■; 3-methylundecane, Δ; and HRFcamelina, ●. Error bars, which are the combined expanded uncertainties with 0.95 level of confidence (k ≈ 2), are smaller than symbols.

Figure 12. Speed of sound of 2-methylpentadecane, □ ; 7methylhexadecane, Δ; HRF-76, ▲. Error bars, which are the combined expanded uncertainties with 0.95 level of confidence (k ≈ 2), are smaller than symbols.

c /m·s−1 = AT /K + B

(3)

using the Microsoft Excel linear regression software in its Analysis Toolpak. The fitting parameters are given in Table 9, and all fits are good with an R2 > 0.999. These lines are shown on Figures 11 to 13. As the carbon chain length on the 2-methyl alkane molecule increases, the speed of sound increases as is seen with straight chain hydrocarbons. When comparing the 2-methyl alkanes to their straight chain isomers, the 2-methyl isomers have a lower speed of sound. For example from eq 3 at 298.15 K, the speed of sound of 2-methyl octane, 1182 m·s−1, is lower than that of nonane, 1207.4 m·s−1,52 while the speed of sound of 2-methyl decane, 1238 m·s−1, is lower than that of undecane, 1257.95 m·s−1.52 For these two carbon increases to the molecular structure, the change in the speed of sound is slightly greater for these 2-methyl alkanes, 56 m·s−1, than for their straight chained isomers 51 m·s−1. The dimethyl alkanes also have a

Figure 13. Speed of sound of 3,5-dimethylheptane, □ ; 4methyloctane, ○; and 3,6-dimethyloctane, ■. Error bars, which are the combined expanded uncertainties with 0.95 level of confidence (k ≈ 2), are smaller than symbols.

was used to fit the viscosity data. The Microsoft Excel linear regression software in its Analysis Toolpak was used to fit the log−linearized form of this equation to the data. The fits, shown in Figures 6 to 9, were good with R2 values greater than 0.98, and the coefficients of eq 2 are given in Table 6. The viscosity of compounds with longer hydrocarbon chains have a greater dependence on temperature, as can be seen with the 2072



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Table 10. Calculated Values of the Bulk Modulus Ev (MPa) for Methylalkanes, Dimethylalkanes, and Hydrotreated Renewable Fuels from T = (293 to 323) Ka 3,5-dimethyl heptane 2-methyl octane 4-methyl octane 3,6-dimethyl octane 2-methyl nonane 2-methyl decane 3-methyl undecane 2-methyl pentadecane 7-methyl hexadecane HRF-camelina HRF-tallow HRF-76

T = 283.15 K

T = 293.15 K

T = 303.15 K

T = 313.15 K

T = 323.15 K

1138 1116 1146 1219 1187 1252 1342 1486 1527 1385 1325 1488

1052 1032 1059 1130 1102 1165 1252 1393 1433 1294 1234 1395

970 953 977 1046 1021 1083 1166 1305 1344 1207 1149 1306

893 879 900 967 944 1005 1086 1222 1529 1125 1068 1222

822 809 828 893 873 932 1009 1144 1179 1047 992 1143

Standard uncertainties u are u(T) = 0.01 K, and combined expanded uncertainties Uc is Uc(Ev) ≤ 1 MPa (level of confidence = 0.95, k ≈ 2). The density values from the DSA 5000 were used to calculate bulk modulus. a

Figure 14. Bulk modulus of 2-methyloctane, ◇; 2-methylnonane, ○; 2-methyldecane, ×; HRF- tallow, ■; 2-methylundecane, Δ; and HRFcamelina, ●. Error bars, which are the combined expanded uncertainties with 0.95 level of confidence (k ≈ 2), are smaller than symbols.

Figure 16. Bulk modulus of 3,5-dimethylheptane, □; 4-methyloctane, ○; 3,6-dimethyloctane, ■. Error bars, which are the combined expanded uncertainties with 0.95 level of confidence (k ≈ 2), are smaller than symbols.

Ev /Pa = (c 2/m 2·s−2)(ρ/kg·m−3)

(4)

These bulk modulus values are given in Table 10. The bulk modulus increases as the number of carbon atoms in 2-methyl alkane increases as shown in Figures 14 to16. At 313.15 K, the bulk modulus values range from 893 to 1529 MPa for the individual branched alkanes, and from 1068 to 1222 MPa for the HRF fuels. At the same temperature, Tat and van Gerpen25 report bulk moduli of 1398.2 MPa for petroleum diesel and 1566.9 MPa for a soybean-based biodiesel. The HRF fuels and the methyl alkanes used in the current study have lower bulk moduli than the petroleum diesel and the biodiesel. In their engine measurements, Tat and van Gerpen25 showed that the injection pressure pulse for biodiesel was 1.5°−2.0° advanced from that of petroleum diesel fuel for fixed injection pump timing. Using a simple model, they attributed 0.45 to 0.68° of the timing advance to the difference in the bulk moduli, which is 169 MPa.25 The difference between the bulk moduli of HRF fuels and that of the petroleum diesel in Tat and van Gerpen25 is greater than 169 MPa, so it is expected that these fuels will also impact engine timing.

Figure 15. Bulk modulus of 2-methylpentadecane, □; 7-methylhexadecane, Δ; HRF-76, ▲. Error bars, which are the combined expanded uncertainties with 0.95 level of confidence (k ≈ 2), are smaller than symbols.

lower speed of sound than their straight chain isomers. The speed of sound of 3,6-dimethyloctane at 298.15 K as predicted by eq 3, 1217 m·s−1, is lower than that of decane, 1234.75 m·s−1.52 The isentropic bulk modulus, Ev, was calculated by

5. CONCLUSIONS In this work, the physical properties of monomethyl and dimethyl alkanes and hydrotreated renewable fuels were measured for temperatures between 293 K and 373 K. Many 2073



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(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) Wood, C. P.; McDonell, V. G.; Smith, R. A.; Samuelsen, G. S. Development and application of a surrogate distillate fuel. J. Propul. Power 1989, 5, 399−405. (13) Bruno, T. J.; Smith, B. L. Evaluation of the physicochemical authenticity of aviation kerosene surrogate mixtures. Part 1: Analysis of volatility with the advanced distillation curve. Energy Fuels 2010, 24, 4266−4276. (14) Bruno, T. J.; Huber, M. L. Evaluation of the physicochemical authenticity of aviation kerosene surrogate mixtures. Part 2: Analysis and prediction of thermophysical properties. Energy Fuels 2010, 24, 4277−4284. (15) Honnet, S.; Seshadri, K.; Niemann, U.; Peters, N. A surrogate fuel for kerosene. Proceed. Combust. Inst. 2009, 32, 485−492. (16) 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. (17) Huber, M. L.; Lemmon, 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. (18) 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. (19) Mathieu, O.; Djebaili-Chaumeix, N.; Paillard, C. E.; Douce, F. Experimental study of soot formation from a diesel fuel surrogate in a shock tube. Combust. Flame 2009, 156, 1576−1586. (20) Anand, K.; Ra, Y.; Reitz, R. D.; Bunting, B. Surrogate Model Development for Advanced Combustion Engines. Energy Fuels 2012, 25, 1474−1484. (21) Lemaire, R.; Faccinetto, A.; Therssen, E.; Ziskind, M.; Focsa, C.; Desgroux, P. Experimental comparison of soot formation in turbulent flames of diesel and surrogate diesel fuels. Proc. Combust. Inst. 2009, 32, 737−744. (22) Ramirez Lancheros, H. P.; Fikri, M.; Rincon Cancino, L.; Moreac, G.; Shulz, C.; Dagaut, P. Autoignition of surrogate biodiesel fuel (B30) at high pressure: Experimental and modeling kinetic study. Combust. Flame 2012, 33, 996−1008. (23) 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 temperature. Combust. Flame 2013, 160, 232−239. (24) 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. (25) Tat, M. E.; van Gerpen, J. H. Measurement of Biodiesel Speed of Sound and Its Impact on Injection Timing, Final Report, Report 4 in a series of 6 for National Renewable Energy Laboratory: Golden, CO, February 2003. (26) Morris, R. E. Personal communication, 2011, based on method described in Begue, N. J.; Cramer, J. A.; Von Bargen, C.; Myers, K. M.; Johnson, K. J.; Morris, R. E. Automated Method for Determining Hydrocarbon Distributions in Mobility Fuels. Energy Fuels 2012, 25, 1617−1623. (27) Mackay, D., Shiu, W. Y., Ma, K.-C., Lee, S. C. Introduction and Hydrocarbons. Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals; Taylor & Francis Group: Boca Baton, FL, 2006; Vol. 1. (28) Geist, J. M.; Cannon, M. R. Viscosities of pure hydrocarbons. Ind. Eng. Chem. 1946, 18, 611−613. (29) Pomerantz, P.; Fookson, A.; Mears, T. W.; Rothberg, S.; Howard, F. L. Synthesis and physical properties of several aliphatic and alicyclic hydrocarbons. J. Res. Natl. Bureau Stand. (U. S.) 1954, 52, 59− 65 ; Research Paper No. 2473.

of the measurements of the pure components agree with values reported in the literature. Over this temperature range, density varied from (661 to 788) kg·m−3, and viscosity from (0.261 to 5.36) mPa·s. Over the temperature from (283.15 to 323.15) K, the speed of sound ranged from (1081 to 1393) m·s−1 and the bulk modulus spanned from (809 to 1527) MPa. All values increased as the carbon chain length on the alkane increased, which is similar to the behavior with linear alkanes. When the properties of the 2-methyl alkanes and that of their straight chain isomers were compared, it was found that the density of the 2-methyl alkanes was larger, the speed of sound was lower, and the viscosity of the 2-methyl alkanes was lower or the same as the values of their straight chain isomers. For HRF fuels from camelina and tallow and for a mixture of an HRF from diesel with petroleum diesel, the physical properties fell within the values measured for the pure components. The speed of sound for all HRF fuels and branched alkanes studied was found to be lower than that of petroleum diesel. With the density, viscosity, and speed of sound measurements, these methyl alkanes can be added to the palette of potential chemicals that can be used to develop surrogate mixtures for HRFs.

■

AUTHOR INFORMATION

Corresponding Author

*Tel.: (410) 293-6339. Fax: (410) 293-2218. E-mail: prak@ usna.edu. Funding

This work was funded by a grant from the Office of Naval Research. Notes

The authors declare no competing financial interest.

■

REFERENCES

(1) Knothe, G. Biodiesel and renewable diesel: A comparison. Prog. Energy Combust. Sci. 2010, 36, 364−373. (2) Bruno, T. J.; Baibourine, E. Comparison of biomass-derived turbine fuels with composition-explicit distillation curve method. Energy Fuel 2011, 25, 1847−1858. (3) . U.S. Navy Energy, Environment, and Climate Change: Great Green Fleet. http://greenfleet.dodlivre.mil/energy/great-green-fleet/ (accessed 7 May 2013). (4) Aatola, H.; Larmi, M.; Sarjovaara, T.; Mikkonen, S. HVO as renewable diesel fuel: Trade-off between NOx, particulate emission, and fuel consumption of a heavy duty engine. SAE Int. J. Engines 2009, 1, 1251−1262, DOI: 2008-01-2500. (5) Caton, P. A.; Williams, S. A.; Kamin, R. A.; Luning Prak, D.; Hamilton, L. J.; Cowart, J. S. Hydrotreated algae renewable fuel performance in a military diesel engine. Proceedings of the 2012 Spring Technical Conference; May 6−9, 2012; American Society of Mechanical Engineers (ASME) Paper ICES2012-81048. (6) 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. (7) 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. (8) Pitz, W. J.; Mueller, C. J. Recent progress in the development of diesel surrogate fuels. Prog. Energy Combust. Sci. 2011, 37, 340−350. (9) Huber, M. L.; Lemmon, E. W.; Ott, L. S.; Bruno, T. J. Preliminary surrogate mixture models for the thermophysical properties of rocket propellants RP-1 and RP-2. Energy Fuel 2009, 23, 3093−3088. (10) Edward, T.; Maurice, L. Q. Surrogate mixtures to represent complex aviation and rocket fuels. J. Propul. Power 2001, 19, 461−466. 2074



Article

(30) White, J. D.; Glasgow, A. R. Separation of the three methyl octanes from midcontinent petroleum. J. Res. Natl. Bur. Stand. (U. S.) 1937, 19, 423. (31) Material Safety Data Sheet for 2-Methylundecane; MP Biomedicals: Seven Hills, Australia, revised April 25, 2006. (32) Petrov, A. A.; Sergienko, S. R.; Nechitailo, N. A.; Tsedilina, A. L. Synthesis and properties of monomethyl alkanes of composition C12− 16. Izv. Akad. Nauk, Ser. Khim. 1959, 1091−7. (33) Dupont, G. Acetylenic γ-glycols and ketohydrofurans derived from them. Ann. Chim. Phys. 1913, 30, 485−587. (34) Petrov, A. D.; Melekhin, V. M.; Sushchinskii, V. L. Synthesis of 2,3,4,5-tetramethylhexane and 2,3,5-trimethyltheptane. Dokl. Akad. Nauk SSSR 1953, 89, 487−490. (35) Mears, T. W.; Fookson, A.; Pomerantz, P.; Rich, E. W.; Dussinger, C. S.; Howard, F. L. Syntheses and properties of two olefins, six paraffins, and their intermediates. J. Res. Natl. Bureau Stand. 1950, 44, 299−311. (36) Material Safety Data Sheet for 2-Methyloctane; TCI America: Seekonk, MA, revised March 01, 2005. (37) CRC Handbook of Chemistry and Physics, 93rd ed.; CRC: Boca Raton, FL, 2012−2013. http://www.hbcpnetbase.com (accessed Feb. 2013). (38) Material Safety Data Sheet for 2-Methyldecane; ChemSamp Co.: Trenton, NJ, revised January 01, 2003. (39) Levina, R. Y.; Shusherina, N. P.; Treschova, E. G. Synthesis of hydrocarbons. XXX. Synthesis of 3,5-dimethylheptane. Vstnik Moskov. Univ. 1952, 7, 105−108. (40) Whitmore, F. C.; Southgate, H. A. The nonanes. 2Methyloctane, 3-ethylheptane, 2,3-dimethylheptane, and 2,2,4,4tetramethylpentane. J. Am. Chem. Soc. 1938, 60, 2571−2573. (41) Calingaert, G.; Soroos, H. The methyl nonanes. J. Am. Chem. Soc. 1936, 58, 635−636. (42) Petrov, A. A.; Razumova, N. A.; Genusov, M. L. Conjugated systems. XCV. Reaction of piperylene with its hydrochloride and with 1,4-hydrochloride of isoprene. Diene compounds. LXXI. Reactions of dienes with halogen derivatives. Zh. Obshchei Khim. 1958, 28, 3220− 3224. (43) Material Safety Data Sheet for 3,6-Dimethyloctane; ChemSamp Co.: Trenton, NJ, revised January 01, 2007. (44) Prout, F. S.; Cason, J.; Ingersoll, A. W. Branched-chain fatty acids. V. The synthesis of optically active 10-methyloctadecanoic acid. J. Am. Chem. Soc. 1948, 70, 298−305. (45) Petrov, A. A.; Razumova, N. A.; Genusov, M. L. Telomerization of α-chloro-1,3-butadiene with piperylene hydrochloride (2-chloro-3pentene). Nauchnye Doklady Vysshei Shkoly, Khimiya i Khimicheskaya Tekhnologiya 1959, 1, 123−126. (46) Fox, R. W.; McDonald, A. T. Introduction to Fluid Mechanics, 3rd ed.; Wiley: New York, 1985. (47) Terres, E.; Brinkmann, L.; Fischer, D.; Huellstrung, D.; Lorz, W.; Weisbrod, G. Synthese und physikalische Daten einiger Isoparaffinreihen mit 11 bis 24 C-Atomen. Brennst. Chem. 1959, 40, 279−280. (48) Aucejo, A.; Cruz Burguet, M.; Munoz, R.; Marqués, J. L. Densities, Viscosities and Refractive Indices of some n-Alkanes Binary Liquid Systems at 298.15 K. J. Chem. Eng. Data 1995, 40, 141−147. (49) 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. (50) Doolittle, A. K. Studies in Newtonian flow. II. The dependence of the viscosity of liquids on Free-Space. J. Appl. Phys. 1951, 22, 1471− 1475. (51) Outcalt, S.; Laesecke, A.; Rotin, T. J. Density and Speed of sound of hexadecane. J. Chem. Thermodyn. 2010, 42, 700−706. (52) Tourino, A.; Hervello, M.; Moreno, V.; Iglesias, M.; Marino, G. Thermodynamics of binary mixtures of aliphatic linear alkanes (C6− C12) at 298.15 K. Phys. Chem. Liq. 2004, 42, 37−51.

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Density, Viscosity, Speed of Sound, and Bulk Modulus of Methyl

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