Density, Viscosity, and Thermal Conductivity of Eight Carboxylic Acids

Article pubs.acs.org/jced

Density, Viscosity, and Thermal Conductivity of Eight Carboxylic Acids from (290.3 to 473.4) K Xiaopo Wang,†,‡ Tongfan Sun,† and Amyn S. Teja*,† †

School of Chemical & Biomolecular Engineering, Georgia Institute of Technology, Atlanta, Georgia 30332-0100, United States Key Laboratory of Thermo-Fluid Science and Engineering, Ministry of Education, Xi’an Jiaotong University, Xi’an, Shaanxi 710049, China

‡

ABSTRACT: The density, viscosity, and thermal conductivity of eight carboxylic acids (pentanoic, hexanoic, heptanoic, octanoic, nonanoic, decanoic, dodecanoic, and tetradecanoic acid) were measured at ambient pressure and temperatures ranging from (290.3 to 473.4) K. The expanded uncertainties (k = 2) of the measurements were estimated to be 0.2 kg·m−3 for the density, 0.04 mPa·s for the viscosity, and 0.003 W·m−1·K−1 for the thermal conductivity (at the 95% level of confidence). The data were correlated using the Rackett equation (in the case of the density) and a modified rough hard-sphere (RHS) model (in the case of the viscosity and thermal conductivity). Generalized forms of the RHS model parameters are presented as functions of the carbon number and temperature.

1. INTRODUCTION Carboxylic acids are important chemicals in a variety of industrial applications, including the manufacture of pharmaceuticals, polyester resins, and food products.1,2 Their thermophysical properties are therefore of interest in the design of processing equipment in these applications. However, few measurements of their viscosity or thermal conductivity have been reported.3−10 The present work therefore reports new measurements of the density, viscosity, and thermal conductivity of eight carboxylic acids (pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, dodecanoic acid, and tetradecanoic acid) at ambient pressure and temperatures ranging from (290.3 to 473.4) K. The viscosity and thermal conductivity data have also been correlated using a rough hard sphere model, whereas the density was correlated using the Rackett equation.

Table 1. Source and Purity of the Materials Studied in This Work CAS no.

source

mole fraction purity

109-52-4 142-62-1 111-14-8 124-07-2 112-05-0 334-48-5 143-07-7 544-63-8

Sigma-Aldrich Sigma-Aldrich Sigma-Aldrich Sigma-Aldrich Sigma-Aldrich Sigma-Aldrich Sigma-Aldrich Sigma-Aldrich

⩾0.99 ⩾0.99 ⩾0.99 ⩾0.99 ⩾0.99 ⩾0.99 ⩾0.99 ⩾0.99

pressure vessel and the effective length of the wire was obtained by calibration using IUPAC-suggested values of the thermal conductivity of water and dimethyl phthalate. Estimates of the expanded uncertainties (k = 2) of the measurements are 0.2 kg·m−3 for the density, 0.04 mPa·s for the viscosity, and 0.003 W·m−1·K−1 for the thermal conductivity (at the 95% level of confidence). Additional details regarding the experimental apparatus and procedures can be found elsewhere.11−16

2. EXPERIMENTAL SECTION Table 1 lists the source and purity of the carboxylic acids studied in this work. All chemicals were used as received. The apparatus and methods used in the measurement of the density, viscosity, and thermal conductivity have been described in our previous papers.11−16 Densities were measured using a pycnometer placed inside a constant temperature air bath and calibrated using mercury. Viscosities were measured using a capillary viscometer mounted inside a high-pressure view cell that was placed in a constant temperature air-bath. The view cell was pressurized to suppress boiling, and the viscometer was calibrated using viscosity standards. Thermal conductivity was measured using the relative transient hot-wire method in which a Pyrex capillary filled with mercury served as the insulated hotwire. The hot-wire cell was placed inside a thermostated high© XXXX American Chemical Society

chemical name pentanoic acid hexanoic acid heptanoic acid octanoic acid nonanoic acid decanoic acid dodecanoic acid tetradecnoic acid

3. RESULTS AND DISCUSSION Table 2 lists our measurements of the density, viscosity, and thermal conductivity of the eight carboxylic acids. As expected, all three properties decrease with temperature for each acid. In Special Issue: In Honor of Kenneth R. Hall Received: November 17, 2015 Accepted: May 25, 2016

A

DOI: 10.1021/acs.jced.5b00971 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data

Article

Table 2. Measured Properties of the Carboxylic Acids at 0.1 MPaa T/K

ρ/kg·m−3

293.4 312.1 332.1 352.2 368.1 388.4 408.3 428.2

939.7 922.3 904.1 885.4 870.6 851.0 831.9 812.1

294.5 312.1 332.1 352.1 368.1 388.4 408.3 428.3

926.0 910.5 893.1 875.8 861.7 843.5 825.3 806.5

290.3 308.0 323.1 338.1 353.1 367.1 383.2 397.9 412.9 427.7

920.6 905.7 893.0 880.4 867.8 855.4 842.3 829.4 816.6 803.4

290.3 308.0 323.1 338.1 353.1 367.8 383.1 398.1 412.9 427.7

910.3 898.2 885.9 873.8 861.8 849.7 837.2 824.6 812.3 799.2

290.3 308.0 323.1 338.1

906.0 893.8 881.9 870.1

T /K

η/mPa·s

pentanoic acid 293.4 2.19 312.1 1.56 332.1 1.17 352.2 0.89 368.1 0.75 388.4 0.60 408.3 0.50 428.2 0.41 hexanoic acid 294.6 3.07 312.1 2.15 332.1 1.52 352.1 1.14 368.1 0.94 388.4 0.73 408.3 0.60 428.3 0.49 heptanoic acid 290.3 4.63 308.0 3.06 323.1 2.30 338.1 1.74 353.1 1.39 367.1 1.13 383.2 0.94 397.9 0.79 412.9 0.68 427.7 0.59 octanoic acid 293.3 5.86 308.0 3.98 323.1 2.88 338.1 2.17 353.1 1.69 367.8 1.36 383.1 1.11 398.1 0.92 412.9 0.78 427.7 0.67 nonanoic acid 292.3 8.20 308.0 5.25 323.1 3.66 338.1 2.70

T/K

λ/W·m−1·K−1

T/K

ρ/kg·m−3

296.1 324.1 348.6 374.0 398.0 422.4 446.4 471.3

0.141 0.136 0.131 0.126 0.122 0.118 0.115 0.111

353.1 368.0 383.1 398.1 413.0 427.9

858.4 846.7 834.1 822.3 810.3 798.0

296.9 325.7 347.4 374.7 398.1 422.3 445.6 471.2

0.143 0.138 0.134 0.128 0.124 0.120 0.116 0.113

322.1 332.1 352.1 368.3 388.3 408.2 427.2 428.2 442.2 457.2 472.2

878.0 871.0 855.3 843.1 827.3 812.2 797.2 796.4 784.9 772.9 761.9

296.0 314.4 332.4 352.6 372.2 382.0 391.9 412.4 441.7 471.4

0.144 0.140 0.137 0.133 0.130 0.127 0.124 0.121 0.116 0.110

322.1 332.1 352.1 368.2 388.4 408.1 428.1 442.2 457.2 467.2

872.4 864.6 849.9 838.9 824.1 809.3 794.4 783.5 770.2 762.0

297.2 322.3 352.8 387.6 411.3 442.0 471.7

0.147 0.142 0.136 0.130 0.124 0.118 0.112

332.1 352.1 368.2 388.2 408.2 427.9 443.2 458.2 473.2

861.3 846.9 835.6 821.4 806.7 791.7 780.9 769.3 758.0

296.3 322.6 352.9 381.3

0.150 0.144 0.139 0.133

T /K

η/mPa·s

nonanoic acid 353.1 2.07 368.0 1.63 383.3 1.31 398.1 1.08 413.0 0.90 427.9 0.76 decanoic acid 322.1 4.75 332.1 3.80 352.1 2.55 368.3 1.94 388.3 1.45 408.2 1.10 427.2 0.88 428.2 0.87 442.2 0.75 457.2 0.64 472.2 0.56 dodecanoic acid 322.1 7.21 332.1 5.62 352.1 3.70 368.2 2.69 388.4 1.97 408.1 1.47 428.1 1.11 442.2 0.95 457.2 0.80 467.2 0.72 tetradecanoic acid 332.1 7.77 352.1 4.88 368.2 3.53 388.2 2.48 408.2 1.79 427.9 1.35 442.2 1.13 457.2 0.95 472.2 0.81

T/K

λ/W·m−1·K−1

412.2 441.4 471.6

0.126 0.121 0.115

308.0 327.4 348.8 373.9 398.3 421.9 447.3 473.4

0.154 0.150 0.146 0.140 0.135 0.130 0.125 0.119

324.6 348.7 373.8 398.4 422.0 447.5 472.7

0.156 0.151 0.145 0.140 0.134 0.129 0.123

334.4 349.0 374.1 397.7 422.3 447.3 471.9

0.158 0.155 0.149 0.144 0.139 0.133 0.127

a

The standard uncertainties u are u(p) = 0.002 MPa. The expanded uncertainties U are as follows U(T) = 0.1 K, U(ρ) = 0.2 kg·m−3, U(η) = 0.04 mPa·s, and U(λ) = 0.003 W·m−1·K−1 (at the 95% level of confidence)

Table 3. Constants of Equation 1 substance pentanoic acid hexanoic acid heptanoic acid octanoic acid nonanoic acid decanoic acid dodecanoic acid tetradecanoic acid

Mw/g·mol−1 102.13 116.16 130.18 144.21 158.24 172.26 200.32 228.37

Tc/K 19

643 655.120 677.820 69320 71219 72619 743.4321 765.1921

A/kg·m−3

B

C

ARD/%

MRD/%

194.3748 206.6855 219.4320 102.9509 131.5407 207.7591 41.32282 146.4907

0.40324 0.42006 0.43457 0.30411 0.34394 0.43005 0.19675 0.36749

0.50571 0.53004 0.58621 0.33986 0.40553 0.58790 0.23447 0.46022

0.01 0.02 0.01 0.03 0.03 0.03 0.05 0.02

0.03 0.03 0.05 0.09 0.07 0.07 0.10 0.05

addition, the density at a fixed temperature decreases with the number of carbon atoms in the acid, whereas the viscosity

increases with carbon number. It would appear that the increasing length of the flexible alkyl chain leads to packing of B



Article

lower density, whereas the increasing size of the molecule leads to a higher viscosity as expected. The behavior of the thermal conductivity is unusual in that this property decreases with carbon number from acetic to pentanoic acid15,17 but increases slightly with carbon number for carboxylic acids larger than pentanoic acid (Table 2). This type of behavior is also observed in the n-alkanes18 and suggests that the contribution of the carboxylic acid group to the thermal conductivity becomes insignificant as the chain length increases beyond six carbon atoms.

4. CORRELATION OF DATA Densities were correlated using a modified Rackett equation as follows: ρ=

A [1 + (1 − Tr )C ]

(1)

B

Figure 2. Relative deviations between experimental densities and calculated results using eq 1 with constants from Table 3 for hexanoic acid: ☆, this work; ■, Gros and Feuge;7 □, Gabriela et al.;23 ●, Vong and Tsai;24 ○, Costello and Bowden;26 ▲, Jannelli and Pansini;27 △, Vogel;30 ▼, Mumford and Phillips;31 ▽, Suarez and Romero;32 ◀, Phadke;33 ◁, Hunten and Maass;34 ▶, Dorinson et al.;35 ◆, Liao et al.36

where A, B, and C are constants and Tr (= T/TC) is the reduced temperature. The critical temperature TC19−21 and molecular weight Mw of the eight acids used in the correlation are listed in Table 3. Table 3 also lists the constants of eq 1 obtained by regression, as well as the average relative deviation (ARD) and maximum relative deviation (MRD) between experimental data and calculated results. The ARD and MRD were calculated using 100 ARD/% = N

N

∑ i=1

ρiexp − ρical ρiexp

⎛ ρ exp − ρ cal MRD/% = max⎜⎜100 i exp i ρi ⎝

(2)

⎞ ⎟ ⎟ ⎠

(3)

Figures 1 to 8 show comparisons between measured densities (both from this work and from the literature) and densities calculated using eq 1 for the eight carboxylic acids. Deviations between our measured densities and calculated densities were

Figure 3. Relative deviations between experimental densities and calculated results using eq 1 with constants from Table 3 for heptanoic acid: ☆, this work; ■, Bahadur et al;22 □, Gabriela et al.;23 ●, Vong and Tsai;24 ○, Vogel;30 ▲, Bingham and Fornwalt;37 △, Jacquemin et al.;38 ▼, Dorinson et al;35 ▽, Perkin;39 ◀, Dunstan;40 ◁, Jones and Saunders.41

generally less than the measurement uncertainty for each acid. On the other hand, most of the literature data published before 19807,26,28−31,33−35,37,39−41,43,45 exhibited larger deviations from calculated values. The data of Gabriela et al.,23 published in 1990, also exhibited large deviations below about 310 K. Viscosity and thermal conductivity data were correlated using the modified rough hard sphere (RHS) model proposed by Teja and co-workers.46−48 Bleazard and Teja47 showed that their model works well for the viscosity and thermal conductivity of heptanoic, octanoic, and nonanoic acids. However, no experimental data were included in their paper. In this work, therefore, we extend the model to eight carboxylic acids and present all our measurements. The RHS method of Bleazard and Teja47 uses the rough hard sphere expressions for the reduced viscosity η* and reduced

Figure 1. Relative deviations between experimental densities and calculated results using eq 1 with constants from Table 3 for pentanoic acid: ☆, this work; ■, Bahadur et al.;22 □, Gabriela et al.;23 ●, Vong and Tsai;24 ○, Letcher and Redhi;25 ▲, Costello and Bowden;26 △, Jannelli and Pansini;27 ▼, Lodl and Scheller;28 ▽, Klekers and Scheller;29 ◀, Vogel;30 ◁, Mumford and Phillips;31 ◆, Suarez and Romero.32 C



Article

Figure 6. Relative deviations between experimental densities and calculated results using eq 1 with constants from Table 3 for decanoic acid: ☆, this work; ■, Liew et al.;4 □, Gros and Feuge;7 ●, Costello and Bowden;26 ○, Hunten and Maass;34 ▲, Dorinson et al.;35 △, Banipal et al.;42 ▼, Garner and Ryder.43

Figure 4. Relative deviations between experimental densities and calculated results using eq 1 with constants from Table 3 for octanoic acid: ☆, this work; ■, Liew et al.;4 □, Iwahashi et al.;5 ●, Gros and Feuge;7 ○, Gabriela et al.;23 ▲, Vong and Tsai;24 △, Costello and Bowden;26 ▼, Vogel;30 ▽, Mumford and Phillips;31 ◀, Hunten and Maass;34 ◁, Dorinson et al.;35 ▶, Liao et al.;36 ▷, Jacquemin et al;38 ◆, Jones and Saunders;41 ◇, Banipal et al.;42 ◑, Garner and Ryder;43 ×, Sazonov et al.44

Figure 7. Relative deviations between experimental densities and calculated results using eq 1 with constants from Table 3 for dodecanoic acid: ☆, this work; ■, Liew et al.;4 □, Gros and Feuge;7 ●, Costello and Bowden;26 ○, Hunten and Maass;34 ▲, Bingham and Fornwalt;37 △, Banipal et al.;42 ▼, Garner and Ryder.43

Figure 5. Relative deviations between experimental densities and calculated results using eq 1 with constants from Table 3 for nonanoic acid: ☆, this work; ■, Iwahashi et al.;5 □, Mumford and Phillips;31 ●, Dorinson et al.;35 ○, Dunstan;40 ▲, Garner and Ryder;43 △, Adriaanse et al.45

where Vr = V/V0 is the reduced molar volume. The reduced viscosity and thermal conductivity in these equations are defined as follows:

thermal conductivity λ* reported by Assael et al.49−51 and given by ⎛ η* ⎞ log⎜⎜ ⎟⎟ = 1.0945 − 9.2632V r−1 + 71.0385V r−2 ⎝ Rη ⎠ −

301.9012V r−3

+

987.5574V r−6

+

797.69V r−4

−

1221.977V r−5

−

319.4636V r−7

(4)

(6)

⎛ M ⎞1/2 2/3 ⎟ λ* = 1.936 × 107⎜ λV ⎝ RT ⎠

(7)

where M is the molar mass, R is the gas constant, T is the temperature, η is the viscosity, and λ is the thermal conductivity. The coupling parameters Rη and Rλ and the characteristic volume V0 are obtained by fitting experimental viscosity and thermal conductivity data. As discussed by Bleazard and Teja,47 V0, Rη, and Rλ may be expressed as follows: R η = A0 (8)

⎛ λ* ⎞ log⎜ ⎟ = 1.0655 − 3.538V r−1 + 12.120V r−2 ⎝ Rλ ⎠ − 12.469V r−3 + 4.562V r−4

⎛ 1 ⎞1/2 2/3 ⎟ η* = 6.035 × 108⎜ ηV ⎝ MRT ⎠

(5) D



Article

Figure 8. Relative deviations between experimental densities and calculated results using eq 1 with constants from Table 3 for tetradecanoic acid: ☆, this work; ■, Liew et al.;4 □, Gros and Feuge;7 ●, Costello and Bowden;26 ○, Dorinson et al.;35 ▲, Dunstan;40 △, Banipal et al.42

V0 = B0 +

B1 T

Figure 9. Deviations of the model from experimental viscosity data for: ■, pentanoic acid; □, hexanoic acid; ●, heptanoic acid; ○, octanoic acid; ▲, nonanoic acid; △, decanoic acid; ▼, dodecanoic acid; ▽, tetradecanoic acid.

(9)

Rλ = C0 + C1T

(10)

The five coefficients A0, B0, B1, C0, and C1 obtained by fitting our experimental viscosity and thermal conductivity data are listed in Table 4 for each acid. Deviation plots comparing the model with experimental viscosity and thermal conductivity data are shown in Figures 9 and 10, respectively. Average relative deviation (ARD) and maximum deviation (MRD) between calculated and experimental data are given in Table 5. Figure 11 compares our RHS calculations of the viscosity with literature data for the acids. In general, the experimental data of Baykut and Tanrikulu8 for pentanoic, hexanoic, heptanoic, octanoic, nonanoic, and decanoic acid are in agreement with our RHS results. The data of Iwahashi et al.5 for octanoic and nonanoic acids also show good agreement with RHS values. On the other hand, the data of Liew et al.4 for octanoic acid exhibit systematic positive deviations of ∼3% from values calculated using the RHS model. In addition, their data for decanoic, dodecanoic, and tetradecanoic acids only agree with calculated values at temperatures below 338.15 K but exhibit large negative deviations when the temperature exceeds 338.15 K.4 The data of Dunstan et al.3 for the viscosity of pentanoic, hexanoic, and heptanoic acids also exhibit negative deviations of 2−10% from calculated values, although it should be added that these data were measured in 1914 and

Figure 10. Deviations of the model from experimental thermal conductivity data for: ■, pentanoic acid; □, hexanoic acid; ●, heptanoic acid; ○, octanoic acid; ▲, nonanoic acid; △, decanoic acid; ▼, dodecanoic acid; ▽, tetradecanoic acid.

they may not be as reliable as more recent data. Finally, the single value of the viscosity of decanoic acid measured by Knothe and Steidley6 and the measurements of Gros and Fuege7 for tetradecanoic acid also deviate significantly from values calculated using the model. More recently, Harish et al.10 reported the thermal conductivity of dodecanoic acid at 323.15

Table 4. Rough Hard Sphere Coefficients substance

A0

105 B0/m3·mol−1

103 B1/m3·K·mol−1

C0

103 C1/K−1

pentanoic acid hexanoic acid heptanoic acid octanoic acid nonanoic acid decanoic acid dodecanoic acid tetradecanoic acid

0.9946 1.1398 1.3492 1.5738 1.6328 1.2332 1.2786 1.4052

7.4763 8.3873 9.2178 9.8975 10.9724 13.2972 15.8478 18.0614

1.9944 3.4366 5.0102 7.1680 8.3468 6.4355 7.9174 10.157

1.1226 1.3154 1.5274 1.6471 1.7905 2.3065 2.7894 3.2347

1.4089 1.5881 1.6782 2.2187 2.4927 1.5410 1.5878 1.9708

E



Article

R η = 2.22554 − 0.20084Cn + 0.01016Cn2

Table 5. ARD and MD between Experimental and Calculated Values viscosity

105V0 = (1.44287 + 1.19105Cn)

thermal conductivity

substance

ARD/%

MD/%

ARD/%

MRD/%

pentanoic acid hexanoic acid heptanoic acid octanoic acid nonanoic acid decanoic acid dodecanoic acid tetradecanoic acid

0.53 0.39 0.33 0.83 0.93 0.68 1.03 0.29

0.83 0.94 0.87 2.15 1.77 1.11 3.27 0.53

1.17 0.74 0.32 0.31 0.18 0.09 0.20 0.05

2.43 1.93 1.26 0.70 0.46 0.21 0.48 0.08

(14)

+

( −299.529 + 93.045Cn) T

(15)

103Rλ = ( −7.78 + 232.05Cn) + (6.35027 − 0.9012Cn + 0.04203Cn2)T

(16)

Table 6 shows comparisons between experimental data and values calculated using eqs 11−16. Good agreement was Table 6. Comparison of Calculated Values Using Equations 11−16 with Experimental Data viscosity

5. GENERALIZED PARAMETERS FOR THE ACIDS Teja et al.47,48 correlated the viscosity and thermal conductivity of 58 polar liquids using eqs 8−10 and showed that the parameters in the RHS model exhibit regular trends for homologous series of substances. In our work, therefore, the parameters listed in Table 4 were fitted to a function of carbon number and temperature as follows. For C5−C9 acids

ARD/%

MRD/%

3.56 3.41 6.53 6.52 6.44 3.00 3.64 1.93

1.18 0.72 1.41 0.36 0.41 0.56 0.96 0.42 0.75

2.72 2.69 2.71 0.77 0.52 0.72 1.54 0.53

AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected].

(11)

Notes

The authors declare no competing financial interest.

■

10 V0 = (3.23851 + 0.85025Cn)

REFERENCES

(1) King, C. J. Amine-based systems for carboxylic acid recovery: tertiary amines and the proper choice of diluents allow extraction and recovery from water. Chemtech 1992, 5, 285−291. (2) Clifford, S. L.; Ramjugernath, D.; Raal, J. D. Subatmospheric vapor pressure curves for propionic acid, butyric acid, isobutyric acid, valeric acid, isovaleric acid, hexanoic acid and heptanoic acid. J. Chem. Eng. Data 2004, 49, 1189−1192.

(12)

103Rλ = ( −328.36 + 357.88Cn − 13.65Cn2) + (2.06681 − 0.3601Cn + 0.04571Cn2)T

MRD/%

1.52 2.41 3.59 4.09 3.91 1.84 2.67 1.56 2.70

■

5

( −631.411 + 164.361Cn) T

ARD/%

6. CONCLUSIONS The density, viscosity, and thermal conductivity of pentanoic, hexanoic, heptanoic, octanoic, nonanoic, decanoic, dodecanoic, and tetradecanoic acids at ambient pressure and temperatures from (290.3 to 473.4) K were measured and are presented in this work. The estimated expanded uncertainties (k = 2) of the measurements were within 0.2 kg·m−3 for the density, 0.04 mPa·s for the viscosity, and 0.003 W·m−1·K−1 for the thermal conductivity (at the 95% level of confidence). In general, our experimental values agreed with published data within the combined uncertainties of the measurements. In addition, density data were correlated using the Rackett equation and viscosity and thermal conductivity data were correlated using a rough hard-sphere model. RHS parameters for each acid, as well as generalized RHS parameters in terms of carbon number and temperature, are provided in this work.

K and atmospheric pressure. Their thermal conductivity value is smaller by about 10% from that calculated using the RHS method.

+

substance pentanoic acid hexanoic acid heptanoic acid octanoic acid nonanoic acid decanoic acid dodecanoic acid tetradecanoic acid average

obtained between experimental and calculated values, with average relative deviations of 2.70% for viscosity and 0.75% for thermal conductivity.

Figure 11. Relative deviations between published viscosities and calculated results using the RHS model for: ■, pentanoic acid;3 □, pentanoic acid;8 ●, hexanoic acid;3 ○, hexanoic acid;8 ▲, heptanoic acid;5 △, heptanoic acid;8 ▼, octanoic acid;4 ▽, octanoic acid;4 ◀, octanoic acid;8 ◁, nonanoic acid;4 ▶, nonanoic acid;8 ▷, decanoic acid;4 ◆, decanoic acid;6 ◇, decanoic acid;8 ★, dodecanoic acid;4 ☆, dodecanoic acid;9 ◑, tetradecanoic acid;4 ◒, tetradecanoic acid;7 ×, tetradecanoic acid.9

R η = 5.72174‐2.42Cn + 0.39068Cn2 − 0.01914Cn3

thermal conductivity

(13)

For C10−C14 acids F



Article

(3) Dunstan, A. E.; Thole, F. B.; Benson, P. The relation beteween viscosity and chemical constitution. Part VIII. Some homologous series. J. Chem. Soc., Trans. 1914, 105, 782−795. (4) Liew, K. Y.; Seng, C. E.; Lau, E. K. Viscosities of some long-chain fatty acids and their relationship with chain length. J. Am. Oil Chem. Soc. 1991, 68, 488−492. (5) Iwahashi, M.; Yamaguchi, Y.; Ogura, Y.; Suzuki, M. Dynamical structures of normal alkanes, alcohols, and fatty acids in the liquid state as determined by viscosity, self-diffusion coefficient, infrared spectra, and 13C NMR spin lattice relaxation time measurements. Bull. Chem. Soc. Jpn. 1990, 63, 2154−2158. (6) Knothe, G.; Steidley, K. R. Kinematic viscosity of biodiesel fuel components and related compounds. Influence of compound structure and comparison to petrodiesel fuel components. Fuel 2005, 84, 1059− 1065. (7) Gros, A. T.; Feuge, R. O. Surface and interfacial tensions, viscosities, and other physical properties of some n-aliphatic acids and their methyl and ethyl esters. J. Am. Oil Chem. Soc. 1952, 29, 313−317. (8) Baykut, S.; Tanrikulu, M. Investigations of certain properties of nacids and n-alcohols and some mathematical relatinships between these properties and their carbon numbers. Chim. Acta Turc. 1980, 8, 69−76. (9) Gaikwad, B. R.; Subrahmanyam, V. V. R. Physical properties of nsaturated higher fatty alcohols in liquid state. J. Indian Chem. Soc. 1988, 65, 266−268. (10) Harish, S.; Orejon, D.; Takata, Y.; Kohno, M. Thermal conductivity enhancement of lauric acid phase change nanocomposite in solid and liquid state with single-walled carbon nanohorn inclusions. Thermochim. Acta 2015, 600, 1−6. (11) Sun, T.; Ly, D.; Teja, A. S. Densities of acetic acid + water mixtures at high temperatures and concentrations. Ind. Eng. Chem. Res. 1995, 34, 1327−1331. (12) Warrier, P.; Teja, A. S. Density, viscosity, and thermal conductivity of mixtures of 1-ethoxy-1,1,2,2,3,3,4,4,4-nonafluorobutane (HFE7200) with methanol and 1-ethoxybutane. J. Chem. Eng. Data 2011, 56, 4291−4294. (13) Sun, T.; Teja, A. S. Density, viscosity, and thermal conductivity of aqueous benzoic acid mixtures between 375 and 465 K. J. Chem. Eng. Data 2004, 49, 1843−1846. (14) Bleazard, J. G.; Sun, T. F.; Johnson, R. D.; DiGuillio, R. M.; Teja, A. S. The transport properties of seven alkanediols. Fluid Phase Equilib. 1996, 117, 386−393. (15) Bleazard, J. G.; Sun, T. F.; Teja, A. S. The thermal conductivity and viscosity of acetic acid − water mixtures. Int. J. Thermophys. 1996, 17, 111−120. (16) DiGuilio, R. M.; Teja, A. S. Thermal conductivity of poly(ethylene glycols) and their binary mixtures. J. Chem. Eng. Data 1990, 35, 117−121. (17) Bleazard, J. G.; Teja, A. S. Thermal conductivity of electrically conducting liquids by the transient hot-wire method. J. Chem. Eng. Data 1995, 40, 732−737. (18) Calado, J. C. G.; Fareleira, J. M. N.; Nieto de Castro, C. A.; Wakeham, W. A. Thermal conductivity of five hydrocarbons along the saturation line. Int. J. Thermophys. 1983, 4, 193−208. (19) Ambrose, D.; Ghiassee, N. B. Vapor pressures and critical temperatures and critical pressures of some alkanoic acids: C1 to C10. J. Chem. Thermodyn. 1987, 19, 505−519. (20) Andereya, E.; Chase, J. D. The implications of carboxylic acid properties. Chem. Eng. Technol. 1990, 13, 304−312. (21) D'lSouza, R.; Teja, A. S. The Prediction of the Vapor Pressures of Carboxylic Acids. Chem. Eng. Commun. 1987, 61, 13−22. (22) Bahadur, I.; Singh, S.; Deenadayalu, N.; Naidoo, P.; Ramjugernath, D. Influence of alkyl group and temperature on thermophysical properties of carboxylic acid and their binary mixtures. Thermochim. Acta 2014, 590, 151−159. (23) Bernardo-Gil, G.; Esquivel, M.; Ribeiro, A. Densities and refractive indices of pure organic acids as a function of temperature. J. Chem. Eng. Data 1990, 35, 202−204.

(24) Vong, W. T.; Tsai, F. N. Densities, molar volumes, thermal expansion coefficients, and isothermal compressibilities of organic acids from 293.15 to 323.15 K and at pressures up to 25 MPa. J. Chem. Eng. Data 1997, 42, 1116−1120. (25) Letcher, T. M.; Redhi, G. G. Thermodynamic excess properties for binary mixtures of (benzonitrile + a carboxylic acid) at T = 298.15 K. Fluid Phase Equilib. 2002, 198, 257−266. (26) Costello, J. M.; Bowden, S. T. The temperature variation of orthobaric density difference in liquid-vapour system: IV fatty acids. Recl. Trav. Chim. Pays-Bas. 1958, 77, 803−810. (27) Jannelli, L.; Pansini, M. Thermodynamic properties of dilute solutions of C2-C6 n-alkanoic acids in sulfolane. J. Chem. Eng. Data 1985, 30, 349−352. (28) Lodl, S. J.; Scheller, W. A. Isothermal vapor-liquid equilibrium data for the system n-heptane - n-valeric acid at 50, 75, and 100°C. J. Chem. Eng. Data 1967, 12, 485−488. (29) Klekers, A. J.; Scheller, W. A. Isothermal vapor-liquid equilibrium data for the system formic acid - valeric acid at 50, 75, and 100°C. J. Chem. Eng. Data 1968, 13, 480−482. (30) Vogel, A. I. Physical properties and chemical constitution XX. Aliphatic alcohols and acids. J. Chem. Soc. 1948, 1814−1819. (31) Mumford, S. A.; Phillips, J. W. C. The physical properties of some aliphatic compounds. J. Chem. Soc. 1950, 75−84. (32) Suarez, F.; Romero, C. M. Apparent molar volume and surface tension of dilute aqueous solutions of carboxylic acids. J. Chem. Eng. Data 2011, 56, 1778−1786. (33) Phadke, S. R. Studies in the dielectric constants of fatty acids. Part II. Correlation between the structure and the dielectric constant of fatty acids. J. Indian Inst. Sci. 1952, 34, 293−304. (34) Hunten, K. W.; Maass, O. Investigation of surface tension constants in an homologous series from the point of view of surface orientation. J. Am. Chem. Soc. 1929, 51, 153−165. (35) Dorinson, A.; McCorkle, M. R.; Ralston, A. W. Refractive indices and densities of normal saturated fatty acids in the liquid state. J. Am. Chem. Soc. 1942, 64, 2739−2741. (36) Liao, W.-C.; Lin, H. M.; Lee, M.-J. Excess molar enthalpies of binary systems containing 2-octanone, hexanoic acid, or octanoic acid at T = 298.15 K. J. Chem. Thermodyn. 2012, 44, 51−56. (37) Bingham, E. C.; Fornwalt, H. J. Chemical constitution and association. J. Rheol. 1930, 1, 372−417. (38) Jacquemin, J.; Anouti, M.; Lemordant, D. Physico-chemical properties of non-newtonian shear thickening diisopropyl-ethylammonium-based protic ionic liquids and their mixtures with water and acetonitrile. J. Chem. Eng. Data 2011, 56, 556−564. (39) Perkin, W. H. On magnetic rotatory power, especially of aromatic compounds. J. Chem. Soc., Trans. 1896, 69, 1025−1257. (40) Dunstan, A. E. The relation between viscosity and chemical constituion: ix the viscosity and fluidity of the aliphatic acids. J. Chem. Soc., Trans. 1915, 107, 667−672. (41) Jones, D. C.; Saunders, L. Adsorption of the aliphatic acids, acetic to octanoic, at the nitromethane solution-air interface. J. Chem. Soc. 1951, 0, 2944−2951. (42) Banipal, T. S.; Garg, S. K.; Ahluwalia, J. C. Densities of some higher alkan-1-oic acids at temperatures from 343.15 to 373.15 K and at pressures up to 9 MPa. J. Chem. Thermodyn. 1992, 24, 729−735. (43) Garner, W. E.; Ryder, E. A. The alternation in molecular volume of the normal monobasic fatty acids. J. Chem. Soc., Trans. 1925, 127, 720−730. (44) Sazonov, V. P.; Lisov, N. I.; Sazonov, N. V. Influence of temperature on the liquid-liquid equilibria of the ternary system nitromethane + 1-hexanol + octanoic acid. J. Chem. Eng. Data 2002, 47, 599−602. (45) Adriaanse, N.; Dekker, H.; Coops, J. Some physical constants of normal, saturated fatty acids and their methyl esters. Recl. Trav. Chim. Pays-Bas 1964, 83, 557−572. (46) Teja, A. S.; Smith, R. L., Jr.; King, R. K.; Sun, T. F. Correlation and prediction of the transport properties of refrigerants using two modified rough hard-sphere models. Int. J. Thermophys. 1999, 20, 149−161. G



Article

(47) Bleazard, J. G.; Teja, A. S. Extension of the rough hard-sphere theory for transport properties to polar liquids. Ind. Eng. Chem. Res. 1996, 35, 2453−2459. (48) Sun, T. F.; Teja, A. S. Correlation and prediction of the viscosity and thermal conductivity of dense fluids. J. Chem. Eng. Data 2009, 54, 2527−2531. (49) Assael, M. J.; Dymond, J. H.; Papadaki, M.; Patterson, P. M. Correlation and prediction of dense fluid transport coefficients. I. nAlkanes. Int. J. Thermophys. 1992, 13, 269−281. (50) Assael, M. J.; Dymond, J. H.; Polimatidou, S. K. Correlation and prediction of dense fluid transport coefficients. IV. n-Alkanols. Int. J. Thermophys. 1994, 15, 189−201. (51) Assael, M. J.; Dymond, J. H.; Patterson, P. M. Correlation and prediction of dense fluid transport coefficients. V. Aromatic hydrocarbons. Int. J. Thermophys. 1992, 13, 895−905.

H


Density, Viscosity, and Thermal Conductivity of Eight Carboxylic Acids

Recommend Documents