Open access peer-reviewed chapter

Thermodynamic Properties of Propanol and Butanol as Oxygenate Additives to Biofuels

Written By

Eduardo A. Montero, Fernando Aguilar, Natalia Muñoz-Rujas and Fatima E. M. Alaoui

Submitted: 19 May 2016 Reviewed: 12 October 2016 Published: 25 January 2017

DOI: 10.5772/66297

From the Edited Volume

Frontiers in Bioenergy and Biofuels

Edited by Eduardo Jacob-Lopes and Leila Queiroz Zepka

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Abstract

Alternative and renewable energy technologies are being sought throughout the world to reduce pollutant emissions and increase the efficiency of energy use. Oxygenate second-generation biofuels fuels lead to a reduction in pollutant emissions and their thermodynamic and transport properties allow that the facilities for transport, storage and distribution of fuels could be used without modification. Higher alcohols, like propanol and butanol, enhance the octane number, boosting the anti-knock effect in gasoline. Then the compression ratio of the engines can be increased without risk of knocking, leading to higher delivery of power. From the combustion point of view, the production of carbon monoxide and volatile hydrocarbons from the combustion of alcohols is less than the one of gasoline. This chapter covers mixtures of butanol and propanol with hydrocarbons. The properties reviewed are excess volume or density (VE), vapour-liquid equilibrium (VLE), and heat capacity (Cp).

Keywords

  • butanol
  • propanol
  • biofuel
  • density
  • enthalpy
  • phase equilibrium
  • heat capacity

1. Introduction

Biofuels, as environmental friendly fluids, have been paid much attention over the last decades. They contribute to diminish the greenhouse gas emissions due to its neutral carbon dioxide balance. Moreover, some oxygenated compounds are used as biofuel additives as they lead to a reduction in pollutant emissions and to an increase in the energy efficiency of vehicle engines [1, 2].

Some alcohols and ethers, as oxygenated compounds additives, are added to present gasoline with the aim of reducing the emission of gases that produce environmental impact. The advantages of these oxygenates can be classified into several categories. First, they can be obtained from renewable, agricultural and raw materials, reducing the dependence of fossil sources [3]. Second, they enhance the octane number, boosting the anti-knock effect in gasoline. Then, the compression ratio of the engines can be increased without risk of knocking, leading to higher delivery of power. From the combustion point of view, the production of carbon monoxide and volatile hydrocarbons from the combustion of alcohols is less than the one of gasoline. Amongst the thermodynamic properties, the heat of vaporization of alcohols is high and leads to a reduction in the peak temperature of combustion, which means lower emissions of nitrogen oxides.

Alternative and renewable energy technologies are being sought to reduce pollutant emissions and increase the efficiency of energy use. Propanol and butanol have been proposed as an alternative to conventional gasoline and diesel fuels [4, 5]. They are higher member of the series of alcohols with each molecule containing three or four carbon atoms rather than two as in ethanol. The EN standards of the European Union (EU) and the World-Wide Fuel Charter (WWFC) for gasoline include, for example, 2-propanol, 2-methyl-2 propanol (also known as tert-butyl alcohol, TBA), and 2-methyl-1 propanol [6, 7] as gasoline components.

The traditional production and consumption of bioethanol have found an alternative with the second-generation biofuels, such as biobutanol. For example, 85% ethanol, E85, needs some modification of the internal combustion engines specifications, unlike butanols, which can work directly in present engines. The energy content per volume unit of butanol is similar to the one of gasoline, and higher than the same for ethanol. Concerning the contribution to the anti-knocking effect, butanol behaves almost the same as other alcohols like methanol or ethanol. And in the presence of water, the mixture butanol/gasoline shows lesser tendency to separation of phases than the mixture ethanol/gasoline. Then, all the facilities for transport, storage and distribution of fuels can be used without modification. Butanol, which can be synthesized chemically or biologically, is an alternative transportation fuel since it has properties that would allow its use in existing engines with minor hardware modifications [5]. For practical purposes, ASTM D7862 [8] gives specifications for blends of butanol with gasoline at 1–12.5% in volume for automotive spark ignition engines. Three butanol isomers are covered by the specification, 1-butanol, 2-butanol, and 2-methyl-1-propanol, while specifically excludes 2-methyl-2-propanol (TBA).

Besides its use as fuel component, its industrial uses covers a broad range of applications as solvent or as reactive for the production of other chemicals. Applications, chemicals and products that use butanol include solvents, plasticizers, coatings, chemical intermediate or raw material, textiles, cleaners, cosmetics, drugs and antibiotics, hormones, and vitamins.

Since the 1950s, most butanol is obtained from fossil sources [6]. 1-butanol and/or 2-butanol could be obtained from reduction of butyraldehyde with hydrogen, which is previously obtained by hydroformulation reaction of propene (propyelene). Meanwhile, propylene oxide production leads to isobutene, from which TBA could be derived. Butanol from biomass is called biobutanol [9], and it can be used in unmodified gasoline engines. Biobutanol can be produced by fermentation of biomass by the ABE process [9, 10]. The process uses the bacterium Clostridium acetobutylicum, the bacterium for the production of acetone from starch. The butanol was a by-product of this fermentation. Other by-products as acetic, lactic and propionic acids, isopropanol and ethanol, as well as a certain amount of H2, are generated by the process. Ralstonia eutropha can also be used to produce biobutanol, by means of an electro-bioreactor and the input of carbon dioxide and electricity.

According to DuPont [11], existing bioethanol plants can be converted to biobutanol production with low economic cost. The main modification could affect to the fermentation process, with minor changes in distillation, as both alcohols use the same stocks: food energy crops (sugar beets, sugar cane, corn grain, wheat, etc.), non-food energy crops (switchgrass, cellulose, etc.) and agricultural by-products (straw, corn stalks, etc.).

Biopropanol is a rarely discussed biofuel. Tough propanol is included as regular component of gasolines [6], its frequent use as chemical solvent makes it rare to consider it as a fuel. Biopropanol could be produced from microbial fermentation of biomass (cellulose), but the process is extremely inefficient [12]. The issues with microbial production of biopropanol are analogous to the issues with microbial production of biobutanol, so if biobutanol becomes a more practical biofuel to produce, then biopropanol will also become more feasible.

This paper concerns thermodynamic properties of 1-propanol, 2-propanol, 1-butanol, 2-butanol and TBA. Accurate experimental data on thermodynamic properties should be available to check and develop predictive empirical equations, models and simulation programs. Industrial processes as storage, transport, separation and mixing processes also need reliable data for its design. As a result, the experimental literature reviews on properties of pure compounds and its mixtures with characteristic hydrocarbons can provide valuable information about the fluid behaviour under various temperature and pressure conditions.

The paper presents the literature review of available data on thermodynamic properties (density, vapour-liquid equilibrium, specific heat,) of the mixtures of 1-propanol, 1-butanol, TBA and its mixtures with hydrocarbons representatives of gasoline. Density has to do with the volumetric behaviour of the mixtures under pressure and temperature conditions and is the primary data to check equations of state. The vapour-liquid equilibria, which allows the calculation of the Gibbs function, deal with the equilibrium between the liquid and vapour phase under fixed pressure and temperature conditions. And the heat capacity gives information related to the sensible energy storage of the liquids. The review includes only the interval of temperature and pressure of every property reported. The wider is the range of pressure and temperature of the measured properties, so it would be the reliability of the applications of predictive and equations and models. Discussion of further data (uncertainties, experimental apparatus, etc.) would require more space than available. Interested readers should access the literature references to check these issues.

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2. The literature review

Thermodynamic properties of liquid propanol and butanol and its liquid mixtures with some hydrocarbon have been obtained from the literature search using online library databases (Web of Science©, Scopus©, NIST© Standard Reference Database) and high impact electronic journals.

Special attention is given to alcohol + hydrocarbon mixtures. As stated, 1-propanol, 1-butanol and TBA have been selected as alcohols. As representative of hydrocarbons, n-heptane, 2,2,4 trimethylpentane (iso-octane), cyclohexane, methyl-cyclohexane, benzene, toluene and 1-hexene have been chosen. They represent linear, branched and cyclic alkanes, aromatics, as well as olefins, which are regular components of gasoline. Table 1 presents the list of selected compounds.

Compound CAS number Chemical formula
Alcohols
1-Propanol 71-23-8 C3H8O
1-Butanol 71-36-3 C4H10O
Tert-butyl alcohol (TBA) 75-65-0 C4H10O
Hydrocarbons
Heptane 142-82-5 C7H16
2,2,4 trimethylpentane (TMP) 540-84-1 C8H18
Cyclohexane 110-82-7 C6H12
Methyl cyclohexane 108-87-2 C7H14
Benzene 71-43-2 C6H6
Toluene 108-88-3 C7H8
1-Hexene 592-41-6 C6H12

Table 1.

Selected alcohols and hydrocarbons.

Concerning properties, there is a huge amount of available thermodynamic data for pure compounds. With respect to the mixtures, density data are shown in Table 2 for binary mixtures alcohol (1) + hydrocarbon (2). Tables 3 and 4 present the vapour-liquid equilibria selected for mixtures alcohol (1) + hydrocarbon (2) and alcohol (1) + hydrocarbon (2) + hydrocarbon (3). Finally, heat capacity data for binary mixtures alcohol (1) + hydrocarbon (2) are provided in Table 5.

Substance 1 Substance 2 References Year Tmin/K Tmax/K Pmin/kPa Pmax/kPa
1-Propanol Heptane [13] 1967 298.15 298.15 101 101
Heptane [14] 1967 348.15 348.15 101 101
Heptane [15] 1977 298.15 298.15 101 101
Heptane [16] 1982 423.11 523.11 422 5495
Heptane [17] 1983 298.15 298.15 101 101
Heptane [18] 1993 313.15 313.15 101 101
Heptane [19] 1994 278.15 308.15 101 101
Heptane [20] 1995 298.15 298.15 101 101
Heptane [21] 1996 298.15 308.15 101 101
Heptane [22] 1997 298.15 298.15 101 101
Heptane [23] 1998 278.15 308.15 101 101
Heptane [24] 2003 308.15 308.15 101 101
Heptane [25] 2004 293.15 318.21 101 101
Heptane [26] 2005 298.15 298.15 101 101
Heptane [27] 2005 298.15 298.15 101 101
2,2,4 trimethylpentane [28] 1981 298.15 298.15 101 101
2,2,4 trimethylpentane [29] 2007 298.15 298.15 101 101
2,2,4 trimethylpentane [30] 2007 303.15 303.15 101 101
2,2,4 trimethylpentane [31] 2012 298.15 298.15 101 101
2,2,4 trimethylpentane [32] 2015 298.15 323.15 101 101
Cyclohexane [33] 1979 298.15 298.15 101 101
Cyclohexane [34] 1980 298.15 298.15 101 101
Cyclohexane [35] 1991 298.15 298.15 101 101
Cyclohexane [36] 1996 298.15 308.15 101 101
Cyclohexane [37] 1997 298.15 303.15 101 101
Cyclohexane [38] 1998 303.15 303.15 101 101
Cyclohexane [24] 2003 308.15 308.15 101 101
Cyclohexane [39] 2004 298.15 298.15 101 101
Cyclohexane [26] 2005 298.15 298.15 101 101
Cyclohexane [40] 2007 293.15 303.15 101 101
Cyclohexane [41] 2008 303.15 303.15 101 101
Cyclohexane [42] 2016 303.15 313.15 101 101
Methylcyclohexane [43] 1977 303.15 303.15 101 101
Methylcyclohexane [44] 1996 298.15 298.15 101 101
Methylcyclohexane [45] 2006 298.15 308.15 101 101
Benzene [46] 1969 298.15 298.15 101 101
Benzene [33] 1979 298.15 298.15 101 101
Benzene [34] 1980 298.15 298.15 101 101
Benzene [47] 1993 308.15 308.15 101 101
Benzene [58] 1994 298.15 298.15 101 101
Benzene [59] 2001 303.15 303.15 101 101
Benzene [24] 2003 308.15 308.15 101 101
Benzene [39] 2004 298.15 298.15 101 101
Benzene [50] 2007 288.15 313.15 101 101
Benzene [51] 2008 298.15 298.15 101 101
Benzene [52] 2009 298.15 298.15 101 101
Benzene [53] 2015 303.15 303.15 101 101
Toluene [54] 1980 298.15 298.15 101 101
Toluene [47] 1993 308.15 308.15 101 101
Toluene [48] 1994 298.15 298.15 101 101
Toluene [55] 2000 303.15 313.15 101 101
Toluene [24] 2003 308.15 308.15 101 101
Toluene [56] 2005 303.15 333.15 100 30000
Toluene [57] 2006 298.15 298.15 101 101
Toluene [58] 2006 303.15 333.15 101 101
Toluene [59] 2008 298.15 298.15 101 101
Toluene [53] 2015 303.15 303.15 101 101
1-Hexene [60] 1993 298.15 298.15 101 101
1-Hexene [61] 2010 298.15 298.15 101 101
1-Butanol n-Heptane [15] 1977 298.15 298.15 101 101
n-Heptane [62] 1979 298.15 298.15 101 101
n-Heptane [17] 1983 298.15 298.15 101 101
n-Heptane [63] 1984 298.15 298.15 101 101
n-Heptane [64] 1994 313.15 313.15 101 101
n-Heptane [21] 1996 298.15 308.15 101 101
n-Heptane [65] 1997 293.15 293.15 101 101
n-Heptane [66] 1997 288.15 298.15 101 101
n-Heptane [24] 2003 308.15 308.15 101 101
n-Heptane [67] 2003 316.85 458.15 4930 4930
n-Heptane [26] 2005 298.15 298.15 101 101
n-Heptane [68] 2006 288.15 308.15 101 101
n-Heptane [69] 2009 288.15 308.15 101 101
2,2,4 trimethylpentane [65] 1997 293.15 293.15 101 101
2,2,4 trimethylpentane [66] 1997 288.15 298.15 101 101
2,2,4 trimethylpentane [31] 2012 298.15 298.15 101 101
2,2,4 trimethylpentane [70] 2013 298.15 328.15 101 101
Cyclohexane [33] 1979 298.15 298.15 101 101
Cyclohexane [34] 1980 298.15 298.15 101 101
Cyclohexane [71] 1983 298.15 318.15 101 101
Cyclohexane [72] 1995 293.15 313.15 101 101
Cyclohexane [38] 1998 303.15 303.15 101 101
Cyclohexane [73] 2001 298.15 298.15 101 101
Cyclohexane [24] 2003 308.15 308.15 101 101
Cyclohexane [74] 2005 298.15 313.15 101 101
Cyclohexane [40] 2007 293.15 303.15 101 101
Cyclohexane [75] 2010 293.15 293.15 101 101
Cyclohexane [76] 2014 293.15 333.15 100 100000
Cyclohexane [42] 2016 303.15 313.15 101 101
Methylcyclohexane [43] 1977 303.15 303.15 101 101
Methylcyclohexane [77] 1989 298.15 298.15 101 101
Methylcyclohexane [78] 2004 303.15 303.15 101 101
Methylcyclohexane [45] 2006 298.15 308.15 101 101
Benzene [46] 1969 298.15 298.15 101 101
Benzene [33] 1979 298.15 298.15 101 101
Benzene [34] 1980 298.15 298.15 101 101
Benzene [79] 1993 298.15 298.15 101 101
Benzene [80] 1994 298.15 308.15 101 101
Benzene [81] 1996 308.15 308.15 101 101
Benzene [49] 2001 303.15 303.15 101 101
Benzene [21] 2003 308.15 308.15 101 101
Benzene [82] 2004 303.15 303.15 101 101
Benzene [83] 2008 288.15 313.15 101 101
Toluene [84] 1940 298.15 298.15 101 101
Toluene [54] 1980 298.15 298.15 101 101
Toluene [81] 1996 308.15 308.15 101 101
Toluene [55] 2000 303.15 313.15 101 101
Toluene [24] 2003 308.15 308.15 101 101
Toluene [70] 2013 298.15 328.15 101 101
Toluene [85] 2015 298.15 328.15 101 101
1-Hexene [86] 2013 273.15 333.15 101 101
TBA n-Heptane [62] 1979 299.15 299.15 101 101
n-Heptane [64] 1994 313.15 313.15 101 101
n-Heptane [87] 2011 303.15 323.15 101 101
2,2,4 trimethylpentane [88] 1999 298.15 298.15 101 101
2,2,4 trimethylpentane [89] 2001 298.15 298.15 101 101
2,2,4 trimethylpentane [90] 2005 298.15 318.15 101 101
Cyclohexane [71] 1983 298.15 318.15 101 101
Cyclohexane [72] 1995 293.15 313.15 101 101
Methylcyclohexane [88] 1999 298.15 298.15 101 101
Benzene [79] 1993 298.15 298.15 101 101
Benzene [91] 1995 313.15 313.15 101 101
Benzene [81] 1996 308.15 308.15 101 101
Benzene [82] 2004 303.15 303.15 101 101
Toluene [81] 1996 308.15 308.15 101 101
Toluene [88] 1999 298.15 298.15 101 101
Toluene [55] 2000 303.15 313.15 101 101

Table 2.

Reported density (g⋅cm−3) for binary mixtures alcohol (1) + hydrocarbon (2).

Substance 1  Substance 2  References  Year  Tmin/K  Tmax/K  Pmin/kPa  Pmax/kPa 
1-propanol  Heptane  [92]  1966  357.72  371.52  101.32  101.32 
Heptane  [14]  1967  347.97  347.97  39.72  73.63 
Heptane  [13]  1967  303.13  333.12  3.92  39.81 
Heptane  [93]  1980  278.16  303.14  1.67  10.17 
Heptane  [16]  1982  423.15  573.15  200  5066 
Heptane  [94]  1991  313.15  313.15  10.95  16.52 
Heptane  [95]  1992  313.15  313.15  9.638  16.428 
Heptane  [96]  1993  303.15  303.15  5.42  10.24 
Heptane  [97]  1995  379.38  475.45  204.5  1032.8 
Heptane  [98]  1995  316.78  357.58  19.60  101.33 
Heptane  [99]  2000  298.15  298.15  –  – 
Heptane  [100]  2004  303.15  343.15  –  – 
2,2,4, trimethylpentane  [28]  1981  328.36  348.50  15.98  72.75 
2,2,4, trimethylpentane  [101]  1994  357.88  365.46  101.3  101.3 
2,2,4, trimethylpentane  [102]  1994  343.15  343.15  42.04  60.07 
2,2,4, trimethylpentane  [29]  2007  303.15  303.15  4.88  10.45 
2,2,4, trimethylpentane  [103]  2011  318.15  318.15  9.00  21.13 
Cyclohexane  [104]  1977  298.15  298.15  2.79  14.29 
Cyclohexane  [105]  1986  347.66  369.17  101.33  101.33 
Cyclohexane  [98]  1995  347.58  347.58  101.33  101.33 
Cyclohexane  [106]  1996  298.15  308.15  2.63  22.1 
Cyclohexane  [107]  1997  323.15  333.15  27.92  61.17 
Cyclohexane  [99]  2000  313.15  343.15  –  – 
Cyclohexane  [108]  2000  298.15  298.15  101.32  101.32 
Methylcyclohexane  [109]  1969  360.13  366.83  101  101 
Methylcyclohexane  [110]  1989  332.98  332.98  29.12  38.60 
Methylcyclohexane  [111]  1997  358.75  373.60  101.3  101.3 
Benzene  [112]  1947  298.94  363.52  13.33  99.99 
Benzene  [113]  1963  349.12  365.92  101  101 
Benzene  [114]  1964  493.16  558.18  2419.4  4904.2 
Benzene  [104]  1977  298.15  298.15  2.79  13.04 
Benzene  [105]  1986  350.03  361.85  101.33  101.33 
Benzene  [115]  1987  313.15  313.15  7.01  25.98 
Benzene  [107]  1997  323.15  333.15  22.02  56.70 
Benzene  [116]  2001  313.15  313.15  7.047  26.069 
Benzene  [117]  2006  313.15  313.15  7.00  25.91 
Benzene  [52]  2008  323.15  323.15  17.98  39.89 
Benzene  [51]  2008  329.45  368.35  50  94 
Toluene  [115]  1987  313.15  313.15  7.01  11.35 
Toluene  [118]  1996  298.15  298.15  2.63  5.39 
Toluene  [119]  2003  293.15  370.15  –  – 
Toluene  [59]  2008  333.15  333.15  20.27  27.41 
Toluene  [120]  2009  323.15  323.15  13.42  17.85 
1-butanol  Heptane  [121]  1966  361.92  376.92  91.2  91.2 
Heptane  [122]  1967  387.93  434.34  192.65  496.63 
Heptane  [63]  1984  333.15  363.15  8.01  89.49 
Heptane  [123]  1990  353.15  373.15  101.32  101.32 
Heptane  [124]  1994  313.15  313.15  4.39  13.22 
Heptane  [98]  1995  312.34  357.58  12.93  74.47 
Heptane  [125]  1996  328.45  366.55  25.63  101.38 
Heptane  [126]  1997  303.15  303.15  1.35  8.26 
Heptane  [99]  2000  298.15  298.15  –  – 
Heptane  [127]  2001  365.05  389.05  95  95 
Heptane  [100]  2004  303.15  343.15  –  – 
Heptane  [138]  2010  349.00  387.75  53.3  91.3 
Heptane  [129]  2012  313.15  313.15  2.51  13.22 
2,2,4-trimethylpentane  [130]  2006  308.15  318.15  2  17 
2,2,4-trimethylpentane  [103]  2011  318.15  318.15  7.2  16.4 
2,2,4-trimethylpentane  [129]  2012  313.15  313.15  2.55  13.71 
2,2,4-trimethylpentane  [131]  2013  313.15  313.15  11.55  13.50 
Cyclohexane  [132]  1968  353.15  383.12  21.23  229.21 
Cyclohexane  [133]  1982  293.15  293.15  –  – 
Cyclohexane  [71]  1983  318.15  318.15  3.41  30.59 
Cyclohexane  [134]  1990  312.8  389.9  –  – 
Cyclohexane  [98]  1995  352.7  352.7  101.33  101.33 
Cyclohexane  [108]  2000  298.15  298.15  101.32  101.32 
Cyclohexane  [99]  2000  313.15  343.15  –  – 
Cyclohexane  [135]  2001  350.95  389.05  95  95 
Cyclohexane  [136]  2002  325.6  386.12  40.0  101.3 
Cyclohexane  [129]  2012  313.15  313.15  2.51  24.83 
Methylcyclohexane  [109]  1969  369.75  385.65  101  101 
Methylcyclohexane  [110]  1989  332.98  332.98  11.07  29.77 
Methylcyclohexane  [111]  1997  368.45  390.50  101.3  101.3 
Benzene  [137]  1939  298.15  298.15  0.85  12.59 
Benzene  [128]  1963  353.21  390.83  101.32  101.32 
Benzene  [114]  1964  513.17  558.18  2032.6  4751.2 
Benzene  [115]  1987  313.15  313.15  2.52  24.37 
Benzene  [79]  1993  298.15  298.15  0.82  12.83 
Benzene  [139]  1995  354.03  425.26  105  303 
Benzene  [140]  2004  308.15  308.15  4.03  20.28 
Benzene  [141]  2006  313.15  313.15  2.49  24.37 
Toluene  [84]  1940  376.12  390.83  101  101 
Toluene  [142]  1963  378.63  390.83  101.33  101.33 
Toluene  [115]  1987  313.15  313.15  2.52  8.48 
Toluene  [134]  1990  349.5  389.9  –  – 
Toluene  [143]  1997  360.9  389.1  56.4  94.0 
Toluene  [119]  2003  323.15  390.15  –  – 
Toluene  [140]  2004  308.15  308.15  2.49  6.39 
Toluene  [129]  2012  313.15  313.15  2.49  8.39 
1-hexene  [131]  2013  313.15  313.15  2.48  44.99 
TBA  Heptane  [145]  1982  313.15  313.15  12.33  19.23 
Heptane  [146]  1983  352.47  371.42  101  101 
Heptane  [124]  1994  313.15  313.15  14.81  19.20 
Heptane  [147]  1995  351.40  368.23  101.3  101.3 
Heptane  [127]  2001  352.25  369.45  95  95 
2,2,4-trimethylpentane  [148]  1999  352.4  372.5  101.3  101.3 
2,2,4-trimethylpentane  [89]  2001  318.13  339.28  15.85  59.49 
2,2,4-trimethylpentane  [149]  2006  353.35  370.55  95.8  95.8 
Cyclohexane  [150]  1976  344.43  354.33  101  101 
Cyclohexane  [71]  1983  318.15  318.15  18.11  36.23 
Cyclohexane  [151]  1985  328.19  343.28  30.43  95.1 
Cyclohexane  [98]  1995  295.35  344.28  13.46  101.40 
Methylcyclohexane  [110]  1989  332.98  332.98  30.44  46.33 
Methylcyclohexane  [148]  1999  353.1  374.0  101.3  101.3 
Benzene  [152]  1902  347.10  347.10  100.66  101.32 
Benzene  [153]  1933  347.10  347.10  –  – 
Benzene  [137]  1939  298.15  298.15  5.60  13.96 
Benzene  [154]  1969  318.15  318.15  18.12  34.32 
Benzene  [155]  1977  346.58  353.98  101  101 
Benzene  [79]  1993  298.15  298.15  5.59  14.83 
Benzene  [98]  1995  296.66  347.19  13.59  101.51 
Benzene  [156]  1998  308.15  308.15  10.18  23.48 
Toluene  [156]  1998  308.15  308.15  6.40  12.97 
Toluene  [148]  1999  355.4  383.8  101.3  101.3 

Table 3.

Reported vapour-liquid equilibria for binary mixtures alcohol (1) + hydrocarbon (2).

Substance 1 Substance 2 Substance 3 References Year Tmin/K Tmax/K Pmin/kPa Pmax/kPa
1-butanol 2,2,4-trimethylpentane 1-hexene [131] 2013 313.15 313.15 2.48 44.99
1-butanol toluene 1-hexene [144] 2015 313.15 313.15 2.51 44.99
TBA Cyclohexane Benzene [98] 1995 294.91 344.25 13.61 101.36

Table 4.

Reported vapour-liquid equilibria for ternary mixtures alcohol (1) + hydrocarbon (2) + hydrocarbon (3).

Substance 1 Substance 2 References Year Tmin/K Tmax/K Pmin/kPa Pmax/kPa
1-propanol Heptane [157] 1976 298.15 298.15 101 101
Heptane [158] 1981 184.97 300.00 101 101
Heptane [159] 1993 298.15 298.15 101 101
1-butanol Heptane [159] 1993 298.15 298.15 101 101
2,2,4 Trimethylpentane [160] 2012 293.15 313.15 101 25,000
Cyclohexane [76] 2014 293.15 313.15 101 25,000
Toluene [161] 1991 298.15 368.15 101 101
1-Hexene [86] 2013 293.15 313.15 101 25,000

Table 5.

Reported heat capacity for binary mixtures alcohol (1) + hydrocarbon (2).

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3. Discussion

3.1. Density of mixtures 1-propanol, or 1-butanol, + hydrocarbon

Table 2 presents density data for the selected mixtures alcohol (1) + hydrocarbon (2). Fifty-nine references correspond to mixtures 1-propanol (1) + hydrocarbon (2) and 51 to the one 1-butanol (1) + hydrocarbon (2), while only 16 references have been found for TBA (1) + hydrocarbon (2).

For 1-propanol (1) + hydrocarbon (2), only atmospheric pressure density data have been found for the binary mixtures, except Refs. [16, 56] that are above 5 MPa. The highest pressure, 30 MPa, is reported by Zeberg-Mikkelsen and Andersen [56]. Temperatures above 350 K are only measured by Zawisza and Vejrosta [16]. Concerning 1-butanol (1) + hydrocarbon (2), Refs. [67, 76] report pressure above the atmospheric pressure. Hundred Megapascal is the maximum pressure measured in Ref. [76]. Reference [67] also reports temperature above 350 K. Finally, mixtures TBA (1) + hydrocarbon are reported only at atmospheric pressure and moderate temperatures, being 323.15 K the highest measured temperature [87]. No data were found for the mixture TBA (1) + 1-hexene (2).

3.2. Vapour-liquid equilibrium of mixtures 1-propanol, or 1-butanol, + hydrocarbon

With respect to the binary mixtures, Table 3 shows 43 references for VLE data on 1-propanol (1) + hydrocarbon (2), 47 for 1-butanol (1) + hydrocarbon (2) and 24 for TBA (1) + hydrocarbon (2). No references for the mixtures 1-propanol (1) + 1-hexene (2) and TBA (1) + 1-hexene (2) were found, while [131] was the only one for 1-butanol (1) + 1-hexene (2). Most references were found for pressures lower or equal to atmospheric pressure. Studies done in Refs. [97, 122, 132] were measured at moderate pressures, below 1.0 MPa, and only Ref. [114] reports pressure close to 5 MPa for both mixtures 1-propanol (1), or 1-butanol (1), + benzene (2).

Concerning temperature, most measurements were performed at low and moderate temperatures. Within the interval 350–400 K, we found a limited number of 27 set of data [51, 63, 84, 98, 105, 109, 111113, 119, 121, 123, 125, 127, 128, 132, 134136, 142, 143, 146150, 155]. Only Refs. [16, 97, 114, 122, 139] report temperatures between 400 and 573 K.

Only three references were found reporting VLE data of ternary mixtures, as shown in Table 4, at atmospheric or lower pressures. Temperatures were moderate, with maximum at 344 K measured in Ref. [98]. No ternary mixture with 1-propanol was found.

3.3. Heat capacity of mixtures 1-propanol, or 1-butanol, + hydrocarbon

Only eight references reporting heat capacity of binary mixtures alcohol (1) + hydrocarbon (2) are cited. Three of them correspond to the binary mixture 1-propanol (1) + heptane (2) at atmospheric pressure and at moderate temperatures (up to 300 K). No other mixture of 1-propanol with the any of selected hydrocarbons was found.

While the heat capacity of 1-butanol with heptane, 2,2,4 trimethylpentane, cyclohexane, toluene and 1-hexane was measured by several authors. It must be pointed out that some measurements [86, 160, 161] have been performed at pressures up to 25 MPa and temperature of 313 K.

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4. Conclusion

The literature review on thermodynamic properties of liquid mixtures of 1-propanol, 1-butanol and TBA with representative hydrocarbons has been reported. Seven hydrocarbons (linear, branched and cyclic alkanes, aromatics, and olefins) have been selected as representative of present and future unleaded gasoline. The review covers density, vapour-liquid equilibrium and heat capacity of mixtures.

The review of density data shows a big amount of data at low pressure and moderate temperatures. Only two references report data above 30 MPa at a maximum temperature of 333 K. And at temperatures above 450 K, the maximum pressure is 5.5 MPa. With respect to the vapour-liquid equilibrium, only one reference shows measurements over 555 K at 5 MPa. Heat capacity data of mixtures are very scarce, tough some high pressure and high temperature data can be found for some alcohol + hydrocarbon mixtures.

The performance of fuels and biofuels in engines and other devices shows a trend of increasing pressure and temperature, which leads to the need of more reliable predictive models for complex mixtures at such conditions. Availability of high pressure and high temperature thermodynamic properties is then a requisite for the implementation of these equation and models. The review shows a lack of reliable data at high pressure and high temperature thermodynamic data, which serve as a basis for the development of predictive equations and models.

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Written By

Eduardo A. Montero, Fernando Aguilar, Natalia Muñoz-Rujas and Fatima E. M. Alaoui

Submitted: 19 May 2016 Reviewed: 12 October 2016 Published: 25 January 2017