Amyl Methyl Ether with - ACS Publications - American Chemical Society

Article pubs.acs.org/jced

Cite This: J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Thermophysical Study of Binary Systems of tert-Amyl Methyl Ether with n‑Hexane and m‑Xylene Waqar Ahmad,†,⊥ Ali Vakilinejad,†,‡ Zachary M. Aman,§ and G. Reza Vakili-Nezhaad*,† †

Petroleum and Chemical Engineering Department, Sultan Qaboos University, Muscat 123, Oman Faculty of Chemical Engineering, University College of Engineering, University of Tehran, Tehran, Iran § School of Mechanical and Chemical Engineering, University of Western Australia, Perth WA 6009, Australia ‡

Downloaded via SWINBURNE UNIV OF TECHNOLOGY on February 3, 2019 at 19:48:43 (UTC). See https://pubs.acs.org/sharingguidelines for options on how to legitimately share published articles.

S Supporting Information *

ABSTRACT: This work presents the experimentally determined density (ρ), viscosity (η), speed of sound (u), and surface tension (σ) data for tert-amyl methyl ether (TAME) + n-hexane and TAME + m-xylene systems at several temperatures (298.15, 308.15, 318.15, 323.15, and 328.15 K). These experimentally determined thermophysical data are utilized to compute various excess/deviation parameters such as molar volume (VE), isentropic compressibility (κEs ), speed of sound (uE), deviation in viscosity (Δ ln η), isobaric thermal expansion coefficient (αEP), and surface tension (σE). The inspection of parameters response may interpret the existing specific molecular interactions as well as the mixing behavior of solutions. The critical analysis of observed parametric behavior have unveiled the strong and weak molecular interactions in TAME with m-xylene and TAME with n-hexane systems, respectively.

1. INTRODUCTION Mixing of unleaded gasoline with oxygenates can improve its octane rating.1,2 The idea of using oxygenated fuels can lead to efficient, smooth, and pollutant-free combustion. The mixing of these fuel additives can minimize the emissions of carbon monoxide, smog-forming toxic pollutants, and unburnt particulates and, thereby, improve the air quality.3,4 Moreover, the use of these additives can enhance the octane rating of fuel by increasing the oxygen content. A variety of compounds such as ethers, alcohols, and esters, in both pure and mixture forms, can be used as oxygenates. Various ethers such as methyl-tertbutyl ether (MTBE), diisopropyl ether (DIPE), dibutyl ether (DBE), ethyl tert-butyl ether (ETBE), and tert-amyl methyl ether (TAME) have been used as oxygenates to improve the combustion performance with toxic-free emission.5 MTBE mixing was extensively reported in literature due to its easy synthesis and cheap availability.6 Moreover, due to its high water solubility, mobility, and resistance to microbial degradation, it has been rendered as ground contaminant.7,8 However, the other aforementioned ethers are less pollutant than MTBE and offer efficient blending features.9−12 In addition, other alcohols and ethers such as 2-methoxyethyl © XXXX American Chemical Society

acetate, 2-ethylhexyl acetate, dimethyl ether, and dimethoxymethane are important alternatives to improve the combustion efficiency of a variety of conventional fossil fuels.13,14 The investigation on thermophysical properties for a binary blend at different temperatures would reveal the type and nature of involved molecular interactions. The analysis of these molecular interactions, generated due to deviation of components properties in solution from those in pure forms, can describe the solution behavior.15 Therefore, the molecular associations observed at different temperatures are significant for development of molecular models for predicting the solution behavior. Moreover, the thermophysical data for nonelectrolyte liquid−liquid mixtures can provide valuable information for designing different industrial operations such as heat transfer, mass transfer, and separation processes.16 In particular, the thermophysical properties for binary blends of fuel oxygenates with different hydrocarbons are crucial for Received: July 9, 2018 Accepted: January 14, 2019

A

DOI: 10.1021/acs.jced.8b00589 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data

Article

deployed to measure the water contents of these chemicals and thus determine their purity levels. The measured water mass fraction is 323.15 > 318.15 > 308.15 > 298.15 K

Moreover, the Redlich−Kister polynomial is utilized to fit the excess/deviation parameters in order to improve their smooth presentation Y = xi(1 − xi) ∑ Ai (1 − 2xi) j

(3)

where Y and Ais denote an excess property and fitting parameters, respectively. The selection of optimum number of fitting parameters is based on standard deviation. The standard deviation can be computed using equation ÄÅ É ÅÅ ∑ (Y − Y )2 ÑÑÑ1/2 cal exp Ñ ÅÅ ÑÑÑ σ(Y ) = ÅÅÅ ÑÑ ÅÅ m−n ÑÑÖ (4) ÅÇ where Ycal and Yexp are the calculated and experimental values of an excess property. “m” and “n” represent the numbers of experimental points and fitting polynomial order, respectively. The least-squares method determined optimum values of fitting parameters, and their standard deviations are presented in Table 4. The excess isentropic compressibility (κEs ) is a significant property to explain the level of molecular interactions in a binary mixture and can be computed through following expression κsE = κs − κsid

E

Figure 1. Plot of excess molar volume (V ) versus TAME mole fraction (x1) for (a) TAME + n-hexane and (b) TAME + m-xylene systems at different temperatures.

(5)

where κs and κids denote the isentropic compressibility of real and ideal mixtures, respectively. The Newton−Laplace relation F



Article

Table 4. Adjustable Parameters of Redlich − Kister Polynomial for Fitting the Deviation/Excess Properties and Their Standard Deviations (σ) for Studied Systems at Different Temperatures TAME + n-hexane property

A0

VE·10−6/m3·mol−1 Δη/mPa·s κEs ·10−12/Pa−1 uE/m·s−1 αEp ·10−4/K−1 σE/m·N m−1

0.7253 −0.1523 −2.1810 5.5769 −0.0024 −0.2844


0.7685 −0.1739 −3.3289 15.2889 −0.0026 −0.3018


1.0573 −0.1939 −0.4027 8.3651 −0.0027 −0.3241


1.1535 −0.1987 2.1290 −3.2806 −0.0028 −0.3333


1.2025 −0.2142 6.0000 −14.7917 −0.0030 −0.3435

A1

A2

298.15 K −0.0973 −0.1887 −0.0028 0.2453 −54.8678 −0.3215 122.3349 −23.0884 −0.000001 0.0002 −0.0494 −0.0619 308.15 K −0.0581 −0.0776 −0.0049 −0.0064 −77.5375 7.3971 138.6268 −54.3551 −0.0002 0.0003 −0.0436 −0.0726 318.15 K −0.0655 0.0371 −0.0096 −0.0045 −82.3834 0.3018 119.6652 −57.5696 −0.0004 0.0003 −0.0443 −0.0994 323.15 K −0.0171 −0.0670 −0.0125 −0.0407 −84.4865 1.3898 113.0211 −37.2472 −0.0006 0.0004 −0.0433 −0.1102 328.15 K −0.0090 0.0476 −0.0125 0.0145 −91.0836 3.6820 118.7915 −46.4766 −0.0004 0.0006 −0.0433 −0.1188

TAME + m-xylene σ

A3

A0

A1

0.1314 0.0222 28.7185 −135.654 0.0001 −0.0192

0.0023 0.0056 0.9738 0.7440 2.8 × 10−5 0.0023

−2.2084 0.0544 −15.5025 106.7177 −0.0025 0.5073

3.6773 −0.0893 24.1692 −234.7590 0.0006 −1.2412

−0.0636 −0.0043 73.2776 −154.183 0.0004 −0.0494

0.0030 0.0009 0.5427 1.4302 4.2 × 10−5 0.0019

−1.4915 0.0487 −14.5012 89.9815 −0.0021 0.2274

3.1404 −0.0909 34.7069 −243.6850 0.0002 −1.2097

0.0306 −0.0623 63.0463 −112.832 0.0005 −0.0458

0.0075 0.0014 0.8740 1.6019 6.1 × 10−5 0.0022

−1.0476 0.0386 −12.7196 68.9617 −0.0017 0.0764

3.1700 −0.0959 37.0130 −229.2240 0.0007 −1.2364

0.0118 −0.0526 67.0055 −107.2740 0.0011 −0.0521

0.0089 0.0009 0.3598 1.4925 7.0 × 10−5 0.0022

−0.8703 0.0351 −10.2495 55.7310 −0.0016 0.0036

3.0004 −0.0946 36.6841 −228.8058 0.0006 −1.2568

0.0112 −0.0367 69.4832 −98.5852 0.0007 −0.0562

0.0076 0.0018 0.3869 1.5833 5.9 × 10−5 0.0023

−0.6147 0.0315 −6.2803 34.0209 −0.0014 −0.0515

2.7148 −0.0947 36.4996 −226.2166 0.0004 −1.1754

can be used to calculate κs from experimental density and speed of sound data ij 1 yz κs = jjj 2 zzz j ρu z k {

A3

σ

3.5310 0.0598 70.9504 187.3567 −0.0009 0.5393

0.0206 0.0011 1.4263 3.0125 2.1 × 10−5 0.0372

3.3259 0.0606 62.5621 192.3767 0.00006 0.7900

0.0242 0.0010 1.4818 2.8663 8.5 × 10−5 0.0332

2.4683 0.0747 67.6258 142.7080 −0.0028 0.8231

0.0287 0.0010 1.6248 2.6542 3.2 × 10−5 0.0366

2.7191 0.0726 75.1160 129.9990 −0.0030 0.8651

0.0385 0.0011 1.6514 2.3571 3.9 × 10−5 0.0357

2.9248 0.0734 78.6273 134.5554 −0.0029 0.5919

0.0537 0.0009 1.6160 2.2359 3.4 × 10−5 0.0315

intrusion of self-associations between n-hexane and m-xylene molecules. It would in turn lead to the formation of specific interactions between TAME and n-hexane, and TAME and mxylene molecules in their binary systems, while the excess parameter of isentropic compressibility is an important indicator of the level of interactions between unlike molecules in a binary system. Estimated κEs values at different temperatures against mole fraction of TAME for studied binary mixtures have been presented in Figure 2. The TAME + n-hexane system shows the sigmoid shapes with negative and positive values at lower and higher mole fractions of TAME, respectively. In contrast, positive and negative values in sigmoid curves at lower and higher mole fractions of TAME have been observed for the TAME + m-xylene system. The estimated positive behavior of κEs implies the presence of weak molecular interactions which guide to a more compressible binary mixture, whereas the obtained negative κEs values attribute to strong heteromolecular interactions leading to a close packed and less compressible binary mixture. The excess speed of sound (uE), using eq 2, is given as

(6)

where u represents the speed of sound for the binary mixture. κsid has been calculated using the Benson and Kiyohara expression ÅÄÅ ÑÉ 2| o o ÅÅ TVi αi 2 ÑÑÑÑ l o ( ∑ xiVi )( ∑ ϕα i i) o id Å ÑÑ − m κs = ∑ ϕiÅÅκs, i + T } o o ÅÅ Ñ o ∑ xiCp , i Cp , i ÑÑ o o ÅÇ n ~ Ö o (7)

where, ϕi is the volume fraction and is calculated as ϕi =

A2 298.15 K −2.1920 −0.0536 −22.7095 −136.3653 0.0004 −1.3433 308.15 K −1.3549 −0.0567 −18.4755 −159.7370 −0.00003 −0.8191 318.15 K 0.1020 −0.0565 −11.5586 −157.1070 0.0009 −0.6933 323.15 K 0.6246 −0.0627 −10.4038 −166.3293 0.0011 −0.6520 328.15 K 1.1579 −0.0640 −1.2984 −177.3162 0.0013 −0.6814

xiVi . ∑ xiVi

αi and Cp,i are the isobaric thermal expansion coefficient and heat capacity, respectively. κs data at all temperatures for both studied binary systems have been presented in Table 3. From the table a decrease and increase in κs over TAME concentration are obvious for TAME + n-hexane and TAME + m-xylene systems, respectively. This descending and ascending trend of κs can be assigned to

u E = u − u id G

(8) DOI: 10.1021/acs.jced.8b00589 J. Chem. Eng. Data XXXX, XXX, XXX−XXX


Article

Figure 2. Plot of excess isentropic compressibility (κEs ) versus TAME mole fraction (x1) for (a) TAME + n-hexane and (b) TAME + mxylene systems at different temperatures.

Figure 3. Plot of excess speed of sound (uE) versus TAME mole fraction (x1) for (a) TAME + n-hexane and (b) TAME + m-xylene systems at different temperatures.

where uid denotes the speed of sound of an ideal binary system and can be computed as uid = (κids ρid)−1/2. ρid is given as ρid = ∑ϕiρi. uE data at all temperatures for studied systems have been graphically presented in Figure 3. Both systems showed the sigmoid behavior at all temperatures. Sigmoid curves showed the positive and negative values for TAME + n-hexane, and negative and positive values for TAME + m-xylene at lower and higher mole fractions of TAME. The positive deviations of speed of sound indicate an increase in the strength of molecular interactions. A careful investigation reveals that the TAME and m-xylene system exhibits higher positive values of uE compared to values for the TAME and n-hexane system. Following the similar effect of temperature on earlier discussed properties and more specifically on the strength of molecular interactions, uE values decrease with an increase in temperature. The isobaric thermal expansion coefficient (αp) has been calculated using the density data at different temperatures through the following expression

where αidp = ∑ϕiαp,i * . αp,i * denotes the isobaric thermal expansion coefficient for pure component i in the mixture. αp values for studied binary systems at all considered temperatures are given in Table 3. This parameter depicts the fractional volume change of a system with change in temperature at constant pressure. αEp data at different temperatures for studied binary mixtures have been presented in Figure 4. Both systems show negative values of αEp over the entire composition span and at all studied temperatures. In general, positive and negative behavior of αEp represent weak and strong molecular interactions in a mixture. Viscosity is another important measure to evaluate the molecular interactions in solution and pure component form. The kinematic viscosity (ν) can be calculated using eq 11, which in turn is used to compute dynamic viscosity (η) through eq 12

αp =

i ∂ ln ρ yz 1 ij ∂V yz 1 i ∂ρ y zz jj zz = − jjj zzz = −jjj Vm k ∂T { p ρ k ∂T { p k ∂T {

(12)

where t is the efflux time marking the flow span of meniscus between two specified points on the viscometer, while k presents the viscometer constant. Moreover, viscosity deviation presents another important tool to explain the molecular interaction in solutions.

(9)

The derivative term in the preceding equation is estimated by differentiating the Redlich−Kister polynomial fitting of the density data with respect to temperature. The excess isobaric thermal expansion coefficient (αEp ) is calculated using eq 2 αpE = αp − αpid

(11)

ν = kt η = νρ

Δ ln η = ln ηmix −

( ∑ xi ln ηi)

(13)

where, ηmix and ηi are the viscosities of mixture and pure component, respectively.

(10) H



Article

viscosity deviations in studied systems are in close match with the predicted VE behaviors. Surface tension is an important critical interfacial property to determine surface accumulation and aggregation state. The surface tension deviation (σE) values calculated using eq 14 for studied systems at considered temperatures are presented in Figure 6. The negative values of σE at different temperatures

Figure 4. Plot of excess isobaric thermal expansion coefficient (αEp ) versus TAME mole fraction (x1) for (a) TAME + n-hexane and (b) TAME + m-xylene systems at different temperatures.

Viscosity deviation (Δ ln η) data at different temperatures for studied binary systems are presented in Figure 5. The negative behavior of Δ ln η at different temperatures and over the whole composition is obvious for the TAME and n-hexane system, whereas the figure clearly illustrates that for the TAME and mxylene system most of the Δ ln η values are positive. It can be attributed to the formation of strong interactions between TAME and m-xylene molecules. Moreover, the observed

Figure 6. Plot of excess surface tension (σE) versus TAME mole fraction (x1) for (a) TAME + n-hexane and (b) TAME + m-xylene systems at different temperatures.

Figure 5. Plot of deviation in viscosity (Δ ln η) versus TAME mole fraction (x1) for (a) TAME + n-hexane and (b) TAME + m-xylene at different temperatures. I



■

and the entire composition span have been observed for the TAME + n-hexane system. The estimated σE behavior is in line with VE, indicating the presence of weak specific interactions between molecules, while both negative and positive values of σE revealing weak and strong molecular interactions have been observed for the TAME and m-xylene system. The decreasing and increasing trend of σE at lower and higher TAME mole fractions agrees with obtained VE behavior. σE reaches minimum values at TAME mole fractions of 0.5 and 0.23 in TAME + n-hexane and TAME + m-xylene systems, respectively. σ E = σmix −

( ∑ xiσi)

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jced.8b00589.

■

ORCID

Waqar Ahmad: 0000-0003-3732-9603 G. Reza Vakili-Nezhaad: 0000-0002-3011-678X Present Address ⊥

W.A.: Department of Built Environment and Energy Technology, Linnaeus University, 35195, Växjö, Sweden

Notes

∂ Λ 21 ∂A

( )

The authors declare no competing financial interest.

■

ACKNOWLEDGMENTS We appreciate the support of Sultan Qaboos University, Muscat, Oman (SQU) for providing the equipment, chemicals, and laboratory facility.

■

Table 5. Adjustable Parameters of LWW Model at given temperature

Λ21

jij ∂Λ 21 zyz jj zz k ∂A {

1.00

Λ21

0.99

jij ∂Λ 21 zyz jj zz k ∂A {

0.64

0.02

308.15 K

318.15 K

323.15 K

328.15 K

0.98

0.99

0.63

0.62

0.63

TAME + m-Xylene 0.99 1.00

1.01

1.00

0.04

0.04

TAME + n-Hexane 1.00 0.99 0.64

0.03

0.03

AUTHOR INFORMATION

*E-mail: [email protected].

are the adjustable parameters of the model and listed in Table 5. %AAD between measured and correlated surface tensions is what indicates that the LWW model can precisely correlate the surface tension for studied binary systems.

298.15 K

Comparison of experimentally determined physical properties with literature reported values for studied pure components (n-hexane, m-xylene, and TAME) at temperature range 298.15−328.15 K and pressure of 0.1 MPa (PDF)

Corresponding Author

The surface tension data for investigated binary systems have been correlated using the LWW model developed by Li et al. The proposed equation is given by ÄÅ ÉÑ x1x 2RT ij ∂Λ 21 yzÅÅÅ 1 ÑÑÑ ÑÑ jj zzÅÅ1 − rm = x1σ1 + x 2σ2 − x 2 + x1Λ 21 k ∂A {ÅÅÅÇ Λ 21 ÑÑÑÖ (15) where σ1, σ2, and rm are the surface tensions for pure TAME, the other component n-hexane/m-xylene, and their binary mixture, respectively. R is the universal gas constant, and T is

parameter

ASSOCIATED CONTENT

S Supporting Information *

(14)

temperature. The other parameters such as Λ21 and

Article

REFERENCES

(1) Marsh, K. N.; Niamskul, P.; Gmehling, J.; Bölts, R. Review of thermophysical property measurements on mixtures containing MTBE, TAME, and other ethers with non-polar solvents. Fluid Phase Equilib. 1999, 156, 207−227. (2) Begley, R.; Rotman, D. Health complaints fuel federal concern over MTBE. Chem. Week 1993, 152, 7. (3) Zhang, Z. H.; Balasubramanian, R. Effects of oxygenated fuel blends on carbonaceous particulate composition and particle size distributions from a stationary diesel engine. Fuel 2015, 141, 1−8. (4) Chen, C. S.; Tien, C. J.; Zhan, K. V. Evaluation of Intrinsic Bioremediation of Methyl Tert-butyl Ether (MTBE) Contaminated Groundwater. J. Soil. Groundwater. Environ. 2014, 19, 9−17. (5) Schifter, I.; González, U.; Díaz, L.; González-Macías, C.; MejíaCenteno, I. Experimental and vehicle (on road) test investigations of spark-ignited engine performance and emissions using high concentration of MTBE as oxygenated additive. Fuel 2017, 187, 276−284. (6) Ainsworth, S. Oxygenates seen as hot market by industry. Chem. Eng. News 1992, 70, 26−30. (7) Levchuk, I.; Bhatnagar, A.; Sillanpää, M. Overview of technologies for removal of methyl tert-butyl ether (MTBE) from water. Sci. Total Environ. 2014, 476, 415−433. (8) Valipour, M.; Maghami, P.; Habibi-Rezaei, M.; Sadeghpour, M.; Khademian, M. A.; Mosavi, K.; Sheibani, N.; Moosavi-Movahedi, A. A. Interaction of insulin with methyl tert-butyl ether promotes molten globule-like state and production of reactive oxygen species. Int. J. Biol. Macromol. 2015, 80, 610−614. (9) Meng, X.; Wu, J.; Liu, Z. Viscosity and Density Measurements of Diisopropyl Ether and Dibutyl Ether at Different Temperatures and Pressures. J. Chem. Eng. Data 2009, 54, 2353−2358. (10) Pandiyan, V.; Vasantharani, P.; Oswal, S. L.; Kannappan, A. N. Thermodynamic and Acoustic Properties of Binary Mixtures of Ethers. 2. Diisopropyl Ether with Arylamines at (303.15, 313.15, and 323.15) K and Application of ERAS Model to Aniline Mixtures with Diisopropyl Ether and Oxolane. J. Chem. Eng. Data 2011, 56, 269− 277.

4. CONCLUSION Density, viscosity, and speed of sound have been measured for TAME + n-hexane and TAME + m-xylene binary systems at a temperature range of 298.15−328.15 K. These experimental values have been utilized to calculate various excess/deviation parameters. The behavior of these parameters over the composition length has been analyzed in terms of specific interactions formulated between the unlike molecules in a binary mixture. TAME + n-hexane and TAME + m-xylene showed the positive and approximately negative values of VE at studied temperatures, which correlated the weak and strong molecular associations in binary solutions, respectively. Both of the studied systems showed the sigmoid trend of κEs and uE at all temperatures. The predicted behaviors of αEp , Δ ln η, and σE for both systems at all temperatures were also found in agreement with VE inferences. The analysis of these excess/deviation properties indicated the presence of specific molecular interactions in studied binary systems. J



Article

(11) Peng, I. H.; Tu, C. H. Densities and Viscosities of Acetone, Diisopropyl Ether, Ethanol, and Methyl Ethyl Ketone with a FiveComponent Hydrocarbon Mixture from 288.15 to 308.15 K. J. Chem. Eng. Data 2002, 47, 1457−1461. (12) Zheng, X.; Zhang, Y.; He, M. Speed of sound measurement in ethyl tert-butyl ether and tert-amyl methyl ether by Brillouin light scattering. Fluid Phase Equilib. 2016, 418, 108−118. (13) Li, X.; Wu, J.; Liu, Z. Thermal Conductivity of Liquid 2Methoxyethyl Acetate, 2-Ethylhexyl Acetate, and Diethyl Succinate. J. Chem. Eng. Data 2012, 57, 2863−2868. (14) Bi, S.; Jia, T.; Zhao, K.; Meng, X.; Wu, J. Liquid density of 2methoxyethyl acetate, 2-ethylhexyl acetate, and diethyl succinate at temperatures from 283.15 to 363.15 K and pressures up to 100 MPa. J. Chem. Eng. Data 2015, 60, 3532−3538. (15) Moosavi, M.; Motahari, A.; Vahid, A.; Akbar, V.; Rostami, A. A.; Omrani, A. Densities, viscosities, and refractive indices of dimethyl carbonate+ 1-hexanol/1-octanol binary mixtures at different temperatures. J. Chem. Eng. Data 2016, 61, 1981−1991. (16) Gnanakumari, P.; Venkatesu, P.; Mohan, K. R.; Rao, M. P.; Prasad, D. H. L. Excess volumes and excess enthalpies of N-methyl-2pyrrolidone with branched alcohols. Fluid Phase Equilib. 2007, 252, 137−142. (17) Reddy, K. S.; Rao, P. S.; Krishnaiah, A. Experimental and theoretical values of sound speeds and viscosities for the binary systems of MTBE with hydrocarbons. J. Mol. Liq. 2007, 135, 14−20. (18) Deng, Z.; Xia, Y.; Long, B.; Ding, Y. Volumetric properties of diisopropyl ether with acetone at temperatures from 283.15K to 323.15K: An experimental and theoretical study. J. Mol. Liq. 2017, 243, 257−264. (19) Li, D.; Qin, X.; Fang, W.; Guo, M.; Wang, H.; Feng, Y. Densities, viscosities and refractive indices of binary liquid mixtures of methyl tert-butyl ether or ethyl tert-butyl ether with a hydrocarbon fuel. Exp. Therm. Fluid Sci. 2013, 48, 163−168. (20) Rubio-Pérez, G.; Muñoz-Rujas, N.; Srhiyer, A.; Montero, E. A.; Aguilar, F. Isobaric vapor-liquid equilibrium, density and speed of sound of binary mixtures 2,2,4-trimethylpentane + 1-butanol or dibutyl ether (DBE) at 101.3 kPa. Fluid Phase Equilib. 2018, 475, 10−17. (21) Gonzalez-Olmos, R.; Iglesias, M.; Santos, B. M. R. P.; Mattedi, S. Thermodynamics of oxygenate fuel additives as a function of temperature. Phys. Chem. Liq. 2008, 46, 223−237. (22) Harkins, W. D.; Jordan, H. F. A method for the determination of surface and interfacial tension from the maximum pull on a ring. J. Am. Chem. Soc. 1930, 52, 1751−1772. (23) Huh, C.; Mason, S. A rigorous theory of ring tensiometry. Colloid Polym. Sci. 1975, 253, 566−580. (24) Witek, M.; Gołdon, A.; Hofman, T.; Domańska, U. Densities and Excess Volumes of Methyl 1,1-Dimethylpropyl Ether + Benzene, or Cyclohexane, or an Alkane (C6−C16) at 298.15 K. J. Chem. Eng. Data 1997, 42, 60−63. (25) Zhu, S.; Shen, S.; Benson, G. C.; Lu, B. C. Y. Excess enthalpies of methyl 1, 1-dimethylpropyl ether + a C6 hydrocarbon at 298.15 K. J. Chem. Eng. Data 1994, 39, 302−303. (26) Linek, J. Excess volumes and refractive indices in the benzenetert-amyl methyl ether and cyclohexane-tert-amyl methyl ether systems at 298.15 K. Collect. Czech. Chem. Commun. 1987, 52, 2839−2843. (27) Arce, A.; Rodil, E.; Soto, A. Molar volumes, molar refractions, and isentropic compressibilities of (ethanol+ methanol+ 2-methoxy-2methylpropane) and (ethanol+ methanol+ 2-methoxy-2-methylbutane) at 298.15 K. J. Chem. Eng. Data 1997, 42, 721−726. (28) Arce, A.; Rodil, E.; Soto, A. Property Changes of Mixing for the 1-Butanol+ Methanol+ 2-Methoxy-2-methylbutane System at 298.15 K and Atmospheric Pressure. J. Chem. Eng. Data 2001, 46, 962−966. (29) Gómez-Marigliano, A. C.; Arce, A.; Rodil, E.; Soto, A. Isobaric vapor− liquid equilibria at 101.32 kPa and densities, speeds of sound, and refractive indices at 298.15 K for MTBE or DIPE or TAME+ 1Propanol binary systems. J. Chem. Eng. Data 2010, 55, 92−97. (30) Marsh, K. TRC Databases for Chemistry and Engineering. TRC Thermodynamic Tables; Thermodynamics Research Center (TRC), Texas A & M University System: College Station, TX, USA, 1994.

(31) Dubey, G. P.; Sharma, M. Study of molecular interactions in binary liquid mixtures of 1-octanol with n-hexane, n-octane, and ndecane using volumetric, viscometric, and acoustic properties. J. Chem. Thermodyn. 2008, 40, 991−1000. (32) Junquera, E.; Tardajos, G.; Aicart, E. Speeds of sound and isentropic compressibilities of (cyclohexane+ benzene and (1chlorobutane+ n-hexane or n-heptane or n-octane or n-decane) at 298.15 K. J. Chem. Thermodyn. 1988, 20, 1461−1467. (33) Schmidt, R. L.; Randall, J. C.; Clever, H. L. The surface tension and density of binary hydrocarbon mixtures: benzene-n-hexane and benzene-n-dodecane. J. Phys. Chem. 1966, 70, 3912−3916. (34) Basu, M.; Samanta, T.; Das, D. Volumetric and acoustic properties of binary mixtures of tri-n-butyl phosphate with n-hexane, cyclohexane, and n-heptane from T = (298.15 to 323.15) K. J. Chem. Thermodyn. 2013, 57, 335−343. (35) Bolotnikov, M. F.; Neruchev, Y. A. Viscosities and Densities of Binary Mixtures of Hexane with 1-Chlorohexane between 293.15 and 333.15 K. J. Chem. Eng. Data 2003, 48, 739−741. (36) Khasanshin, T. S.; Shchemelev, A. P. Sound velocity in liquid nalkanes. High Temp. 2001, 39, 60−67. (37) Zhou, J.; Zhu, R.; Xu, H.; Tian, Y. Densities, excess molar volume, isothermal compressibility, and isobaric expansivity of (dimethyl carbonate + n-hexane) systems at temperatures (293.15 to 313.15) K and pressures from 0.1 MPa up to 40 MPa. J. Chem. Thermodyn. 2010, 42, 1429−1434. (38) Aminabhavi, T. M.; Aralaguppi, M. I.; Bindu, G.; Khinnavar, R. S. Densities, shear viscosities, refractive indices, and speeds of sound of bis (2-methoxyethyl) ether with hexane, heptane, octane, and 2, 2, 4trimethylpentane in the temperature interval 298.15−318.15 K. J. Chem. Eng. Data 1994, 39, 522−528. (39) Dubey, G. P.; Sharma, M.; Dubey, N. Study of densities, viscosities, and speeds of sound of binary liquid mixtures of butan-1-ol with n-alkanes (C6, C8, and C10) at T = (298.15, 303.15, and 308.15) K. J. Chem. Thermodyn. 2008, 40, 309−320. (40) Mascato, E.; Mariano, A.; Pineiro, M. M.; Legido, J. L.; Paz Andrade, M. I. Excess enthalpy, density, and speed of sound determination for the ternary mixture (methyl tert-butyl ether + 1butanol + n-hexane). J. Chem. Thermodyn. 2007, 39, 1247−1256. (41) Nayak, J. N.; Aralaguppi, M. I.; Aminabhavi, T. M. Density, viscosity, refractive index, and speed of sound in the binary mixtures of 1, 4-dioxane+ ethanediol,+ hexane,+ tributylamine, or + triethylamine at (298.15, 303.15, and 308.15) K. J. Chem. Eng. Data 2003, 48, 1152− 1156. (42) Orge, B.; Rodríguez, A.; Canosa, J. M.; Marino, G.; Iglesias, M.; Tojo, J. Variation of densities, refractive indices, and speeds of sound with temperature of methanol or ethanol with hexane, heptane, and octane. J. Chem. Eng. Data 1999, 44, 1041−1047. (43) Bolotnikov, M. F.; Neruchev, Y. A.; Melikhov, Y. F.; Verveyko, V. N.; Verveyko, M. V. Temperature Dependence of the Speed of Sound, Densities, and Isentropic Compressibilities of Hexane + Hexadecane in the Range of (293.15 to 373.15) K. J. Chem. Eng. Data 2005, 50, 1095−1098. (44) Aicart, E.; Tardajos, G.; Diaz Pena, M. Isothermal compressibility of cyclohexane+ n-hexane, cyclohexane+ n-heptane, cyclohexane + n-octane, and cyclohexane+ n-nonane. J. Chem. Eng. Data 1980, 25, 140−145. (45) Yang, C.; Xu, W.; Ma, P. Excess Molar Volumes and Viscosities of Binary Mixtures of Dimethyl Carbonate with Chlorobenzene, Hexane, and Heptane from (293.15 to 353.15) K and at Atmospheric Pressure. J. Chem. Eng. Data 2004, 49, 1802−1808. (46) Vargaftik, N. B. Handbook of thermophysical properties of gases and liquids; Nauka: Moscow, 1972. (47) Guerrero, H.; Cea, P.; Gascón, I.; Royo, F. M.; Lafuente, C. Volumetric study of the mixtures n-hexane+ isomeric chlorobutane: experimental characterization and volume translated Peng−Robinson predictions. J. Phys. Chem. B 2013, 117, 10284−10292. (48) Lien, P. J.; Lin, H. M.; Lee, M. J.; Venkatesu, P. Excess molar enthalpies of dimethyl carbonate with o-xylene, m-xylene, p-xylene, K



Article

ethylbenzene, or ethyl benzoate at 298.15 K. J. Chem. Eng. Data 2003, 48, 110−113. (49) Serrano, L.; Silva, J. A.; Farelo, F. Densities and viscosities of binary and ternary liquid systems containing xylenes. J. Chem. Eng. Data 1990, 35, 288−291. (50) Al-Kandary, J. A.; Al-Jimaz, A. S.; Abdul-Latif, A. H. M. Viscosities, densities, and speeds of sound of binary mixtures of benzene, toluene, o-xylene, m-xylene, p-xylene, and mesitylene with anisole at (288.15, 293.15, 298.15, and 303.15) K. J. Chem. Eng. Data 2006, 51, 2074−2082. (51) Nain, A. K.; Chandra, P.; Pandey, J. D.; Gopal, S. Densities, Refractive Indices, and Excess Properties of Binary Mixtures of 1,4Dioxane with Benzene, Toluene, o-Xylene, m-Xylene, p-Xylene, and Mesitylene at Temperatures from (288.15 to 318.15) K. J. Chem. Eng. Data 2008, 53, 2654−2665. (52) Yang, C.; Ma, P.; Zhou, Q. Excess Molar Volumes and Viscosities of Binary Mixtures of Sulfolane with Benzene, Toluene, Ethylbenzene, p-Xylene, o-Xylene, and m-Xylene at 303.15 and 323.15 K and Atmospheric Pressure. J. Chem. Eng. Data 2004, 49, 881−885. (53) Tardajos, G.; Diaz Pena, M.; Aicart, E. Speed of sound in pure liquids by a pulse-echo-overlap method. J. Chem. Thermodyn. 1986, 18, 683−689. (54) Moumouzias, G.; Ritzoulis, C.; Ritzoulis, G. A Study in Mixtures of γ-Butyrolactone with o-Xylene and m-Xylene: Densities and Viscosities. J. Chem. Eng. Data 1999, 44, 1187−1191. (55) Bhatia, S. C.; Rani, R.; Bhatia, R. Viscosities, densities, speeds of sound and refractive indices of binary mixtures of o-xylene, m-xylene, p-xylene, ethylbenzene and mesitylene with 1-decanol at 298.15 and 308.15K. J. Mol. Liq. 2011, 159, 132−141. (56) Bhalodia, J.; Sharma, S. Viscometric, acoustical and spectroscopic investigation of β-pinene with benzene, toluene, m-xylene and mesitylene at 303.15, 308.15 and 313.15 K and atmospheric pressure. J. Solution Chem. 2013, 42, 1794−1815. (57) Nain, A. K. Ultrasonic and viscometric studies of molecular interactions in binary mixtures of tetrahydrofuran with some aromatic hydrocarbons at temperatures from 288.15 to 318.15 K. Phys. Chem. Liq. 2007, 45, 371−388. (58) Song, C. Y.; Shen, H. Z.; Zhao, J. H.; Wang, L. C.; Wang, F. A. Densities and viscosities of binary mixtures of vitamin K3 with benzene, toluene, ethylbenzene, o-xylene, m-xylene, and p-xylene from (303.15 to 333.15) K. J. Chem. Eng. Data 2008, 53, 1110−1115. (59) Assael, M.; Papadaki, M.; Wakeham, W. Measurements of the viscosity of benzene, toluene, and m-xylene at pressure up to 80 MPa. Int. J. Thermophys. 1991, 12, 449−457. (60) Nayeem, S. M.; Kondaiah, M.; Sreekanth, K.; Rao, D. K. Comparative study of molecular interactions in aromatic, cyclic and aliphatic ketones with 1-octanol at 308.15 K: An insight from ultrasonic velocity and density. J. Mol. Liq. 2015, 207, 286−293. (61) Sun, Y.; Su, L.; Wang, H. Volumetric properties of binary liquid mixtures: Application of the Prigogine−Flory−Patterson theory to excess molar volumes of dichloromethane with benzene or toluene. J. Chem. Thermodyn. 2009, 41, 1154−1161.

L


Amyl Methyl Ether with - ACS Publications - American Chemical Society

Recommend Documents