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Vapor Pressures, Densities, and PC-SAFT Parameters for 11 Bio-compounds

  • Zachariah Steven Baird
  • Petri Uusi-KyynyEmail author
  • Juha-Pekka Pokki
  • Emilie Pedegert
  • Ville Alopaeus
Open Access
Article

Abstract

One major sustainable development goal is to produce chemicals and fuels from renewable resources, such as biomass, rather than from fossil fuels. A key part of this development is data on the properties of chemicals that appear in this bio-based supply chain. Many of the chemicals have yet to be studied thoroughly, and data on their properties is lacking. Here, we present new experimental data on the properties of 11 bio-compounds, along with PC-SAFT parameters for modeling their properties. The measured data includes vapor pressures, compressed densities, and refractive indexes. The 11 bio-compounds are tetrahydrofuran, 2-pentanone, furfural, 2-methoxy-4-methylphenol, 2-methylfuran, dihydrolevoglucosenone, cyclopentyl methyl ether, 2-sec-butylphenol, levoglucosenone, γ-valerolactone, and 2,6-dimethoxyphenol.

Keywords

Bio-compounds Density PC-SAFT Thermodynamic properties Vapor pressure 

1 Introduction

The world is increasingly searching for sustainable substitutes to replace fossil fuels. Biomass from plants is one large resource that could be converted into fuels and chemicals [1]. To accomplish this goal, some have proposed the concept of a biorefinery, which would take raw materials such as biomass and convert them into valuable products needed in modern society [2]. Similar to the current petroleum-based supply chain, a bio-based supply chain would involve hundreds of different chemicals, whether as intermediates or final products [1, 2].

Chemicals relevant to the petroleum industry have been thoroughly studied over the past century, but for many bio-based chemicals there is little, if any, data about their properties. Key thermodynamic and physical properties of bio-compounds will need to be determined in order to produce bio-based chemicals. In this study we measured the vapor pressures, densities and refractive indexes of 11 such bio-compounds.

Several of these bio-compounds show up as intermediates or platform chemicals that could be further converted into a variety of products [2]. Many of the chemicals are, or could be, useful products. Dihydrolevoglucosenone is a potential bio-based alternative for dipolar aprotic solvents, such as N-methyl-2-pyrrolidone and dimethylformamide [3, 4]. 2,6-dimethoxyphenol has a smoky aroma and is an ingredient in artificial smoke-flavoring products [5, 6]. It, and its derivatives, could also be used for producing renewable phenolic resins [7]. 2-methoxy-4-methylphenol is used as a flavoring [8]. 2-sec-Butylphenol has been successfully tested as a solvent for furfural extraction in the so-called biphasic reactor concept, and it may be possible to produce it from lignin [9]. It has also been proposed that alkylphenols, such as 2-sec-butylphenol, be used as a solvent in biofuel production to increase the effectiveness of the process [10]. γ-valerolactone can be used as a fuel and has also been identified as a promising platform chemical that can be used to produce a variety of other chemicals [11, 12, 13, 14]. Tetrahydrofuran is used as a solvent and in producing some polymers [15, 16]. 2-methylfuran has received attention as a potential substitute for gasoline due to its impressive combustion performance [17]. Cyclopentyl methyl ether is used as a solvent, and it has been shown to be a promising solvent for extracting compounds from the aqueous streams present in bio-refineries [18, 19]. Furfural can be used as a selective solvent and is a platform chemical that can be processed into other products [20].

Many of these compounds can also be produced from one another. For instance, dihydrolevoglucosenone is produced via hydrogenation of levoglucosenone, which itself is produced from the sugar levoglucosan that is formed in the pyrolysis of lignocellulosic biomass [21]. In addition, there are reactions for converting between 2-methylfuran, tetrahydrofuran, furfural, and 2-pentanone [2, 22]. 1,3-dimethoxy-2-hydroxybenzene and 2-methoxy-4-methylphenol have been found in plants and in pyrolysis oil [23].

For 6 (2-methoxy-4-methylphenol, 2-sec-butylphenol, 2,6-dimethoxyphenol, cyclopentyl methyl ether, dihydrolevoglucosenone, levoglucosenone) of the 11 compounds there is only a small amount of data, if any at all. For 5 bio-compounds (2-methylfuran, 2-pentanone, furfural, tetrahydrofuran, γ-valerolactone) large amounts of data can be found in the literature. However, even for these 5 compounds the data presented here extends beyond the range covered in the literature. For 7 of the bio-compounds (2-methoxy-4-methylphenol, 2-methylfuran, 2-pentanone, cyclopentyl methyl ether, dihydrolevoglucosenone, furfural, tetrahydrofuran) we measured compressed densities at higher pressures (up to 12 or 16 MPa), and for many of the compounds there was no reliable data available at higher pressures. We have placed a file containing both the literature data we found and our experimental data in a repository at the Open Science Framework, and this file can be obtained at (https://osf.io/u9amn/). An overview of the measurements made in this work is presented in Table 1.
Table 1

Overview of the measurements made in this work

Name

Measured property

Measurement temperature, K

Measurement pressure, MPa

2-Methoxy-4-methylphenol

Density, liquid

293.15–473.15

0.12–11.85

Vapor pressure, liquid

298.22–403.2

9.3E−6–5.3E−3

Refractive index, liquid

293.15–343.15

0.1

2-Methylfuran

Density, liquid

293.14–473.16

0.09–11.85

Refractive index, liquid

293.15

0.1

2-Pentanone

Density, liquid

293.15–473.16

0.09–11.85

Refractive index, liquid

293.15

0.1

2-sec-Butylphenol

Density, liquid

293.15–473.16

0.101

Vapor pressure, liquid

298.21–403.25

4.7E−6–4.6E−3

refractive index, liquid

293.15–343.15

0.1

2,6-Dimethoxyphenol

Density, liquid

333.16–383.16

0.1

Vapor pressure, liquid

333.28–413.16

1.4E−5–1.9E−3

Refractive index, liquid

328.15–343.15

0.1

Cyclopentyl methyl ether

Density, liquid

293.14–473.15

0.09–11.85

Dihydrolevoglucosenone

Density, liquid

293.15–423.16

0.07–15.77

Vapor pressure, liquid

298.26–403.16

1.4E−5–5.2E−3

Refractive index, liquid

293.15–343.15

0.1

Furfural

Density, liquid

293.15–448.15

0.09–11.9

Levoglucosenone

Density, liquid

293.15–363.15

0.1

Vapor pressure, liquid

298.26–403.3

6.2E−6–3.5E−3

Refractive index, liquid

293.15–343.15

0.1

Tetrahydrofuran

Density, liquid

293.14–473.15

0.1–11.85

Refractive index, liquid

293.15

0.1

γ-Valerolactone

Vapor pressure, Liquid

298.23–403.15

4.4E−5–9.9E−3

Refractive index, liquid

293.15–333.15

0.1

2 Methods

2.1 Chemicals

Information about the chemicals used in this study is presented in Tables 2 and 3. The structures of the chemicals are presented in Fig. 1 [24]. The purities were measured using gas chromatography with a flame ionization detector. For most of the chemicals the water content was also measured using a DL38 Karl Fischer Titrator (Mettler Toledo). The purity was calculated by taking the relative peak area from the chromatogram and then accounting for any water by dividing by 1 plus the water content (if measured).
Table 2

Names, identifiers, and suppliers of the chemicals used in this study

Name

Other names

CAS number

InChI key

Supplier

2-Methoxy-4-methylphenol

Creosol, 4-methylguaiacol

93-51-6

PETRWTHZSKVLRE-UHFFFAOYSA-N

Sigma-Aldrich

2-Methylfuran

 

534-22-5

VQKFNUFAXTZWDK-UHFFFAOYSA-N

Sigma-Aldrich

2-Pentanone

Methyl propyl ketone

107-87-9

XNLICIUVMPYHGG-UHFFFAOYSA-N

Sigma-Aldrich

2-sec-Butylphenol

o-sec-Butylphenol

89-72-5

NGFPWHGISWUQOI-UHFFFAOYSA-N

Sigma-Aldrich

2,6-Dimethoxyphenol

Syringol

91-10-1

KLIDCXVFHGNTTM-UHFFFAOYSA-N

Sigma-Aldrich

Cyclopentyl methyl ether

Methoxycyclopentane

5614-37-9

SKTCDJAMAYNROS-UHFFFAOYSA-N

Sigma-Aldrich

Dihydrolevoglucosenone

Cyrene; (5 ~ {R})-6,8-dioxabicyclo[3.2.1]octan-4-one

53716-82-8

WHIRALQRTSITMI-BAFYGKSASA-N

Circa

Furfural

Furan-2-carbaldehyde

98-01-1

DIHRNGWBOKYHHW-UHFFFAOYSA-N

Sigma-Aldrich

Levoglucosenone

(1 ~ {S},5 ~ {R})-6,8-dioxabicyclo[3.2.1]oct-2-en-4-one

37112-31-5

HITOXZPZGPXYHY-UJURSFKZSA-N

Circa

Tetrahydrofuran

Oxolane

109-99-9

WYURNTSHIVDZCO-UHFFFAOYSA-N

Merck

γ-Valerolactone

5-Methyldihydrofuran-2(3H)-one; 5-methyloxolan-2-one

108-29-2

GAEKPEKOJKCEMS-UHFFFAOYSA-N

SAFC

Table 3

Purities of the chemicals used in this study

Name

Purification method

Water content (wt%)

Purity (wt%)

Refractive index nD (at 293 K)a

2-Methoxy-4-methylphenol

 

0.39

99.4

1.5373

2-Methylfuran

Distillation

0.015

99.9

1.4332

2-Pentanone

 

0.05

99.8

1.3903

2-sec-Butylphenol

Vacuum distillation

 

99.9

1.5228

2,6-Dimethoxyphenol

  

99.7

 

Cyclopentyl methyl ether

 

0.0027

100.0

 

Dihydrolevoglucosenone

 

0.045

99.8

1.4732

Furfural

Vacuum distillation

0.013

99.8

 

Levoglucosenone

  

96.2

1.5064

Levoglucosenone

Vacuum distillation

0.25

98.7

1.5065

Tetrahydrofuran

 

0.033

99.9

1.4073

γ-Valerolactone

Vacuum distillation

 

99.5

1.4333

aAtmospheric pressure 0.10 ± 0.01 MPa

Fig. 1

Structures of the chemicals measured in this study. Structures were obtained from PubChem [24]

All samples except one had purities close to 100 %. The one exception was the levoglucosenone used for vapor pressure measurements, which only had a purity of 96.2 wt%. Mass spectroscopy was used to investigate what impurities were present, and most of them were lower weight impurities such as 2-methylpentane, hexane, methylcyclopentane, cyclohexane and acetone. The levoglucosenone also contained one heavier impurity: 2-methoxyphenol. These impurities could be tolerated when measuring the vapor pressure because in the gas saturation method most of the light impurities are removed in the first run. This occurred with levoglucosenone in this study: the vapor pressure was much higher for the first run, and that point was removed. After the vapor pressure measurement, the purity of the levoglucosenone condensed at the outlet of the gas saturation cell was determined to be 98.5 wt%. Later the levoglucosenone was distilled to get a higher purity for the density and refractive index measurements. This distilled sample had a purity of 98.7 wt%.

2.2 Density Measurements

Densities were measured with a DMA HP density meter (Anton Paar). Most of the samples were measured at a range of pressures, and for these measurements a UNIK 5000 pressure sensor (GE) was used (range of 0 to 20 MPa, abs.). The sensor had been calibrated against a MC2-PE calibrator with an EXT600 external pressure module (Beamex). The MC2-PE calibrator had been calibrated by Beamex. The pressure data has a standard uncertainty of 3100 Pa (expanded uncertainty of 6300 Pa at the 95 % level). For three of the samples measurements were only made at atmospheric pressure, and pressure data were taken from the Finnish Meteorological Institute (Tapiola observation station, Espoo, Finland) [25]. For the temperature, the manufacturer of the density meter only states that the accuracy is better than 0.1 K.

The samples were degassed for about 30 min before measuring. This was done by placing the sample in a round-bottomed flask, which was then placed in an ultrasonic bath. Gasses were removed from the system using a vacuum pump.

Water and nitrogen were used to calibrate the density meter. Reference values for these compounds were taken from reference equations of state, [26, 27] and we used the implementations of these equations available in the CoolProp package for Python [28]. Alternatively, these equations of state are also implemented in the NIST thermophysical properties calculator, [29] and we verified the CoolProp implementation by manually comparing the results of the two programs at multiple temperatures and pressures. For optimizing the calibration equation parameters we used the differential evolution solver [30] implemented in the SciPy package [31] for Python. The root mean-squared error between the reference and calculated values was used as the objective function.

Between samples, the performance of the device was checked by measuring air and water. During the study the performance checks indicated that a recalibration was necessary, so for later samples, a second set of calibration parameters were used. For the first calibration the standard uncertainty was estimated to be 0.047 kg·m−3 (expanded uncertainty of 0.092 kg·m−3 at the 95 % level). For the second calibration, the standard uncertainty was estimated to be 0.036 kg·m−3 (expanded uncertainty of 0.072 kg·m−3 at the 95 % level). One major uncertainty component of density is the impurities in the sample. The impurities are sample specific and the effect is included in the uncertainty estimates given in the density results.

One sample, levoglucosenone, was measured at atmospheric pressure using a DMA 5000 M density meter (Anton Paar). The performance of the device was checked with water and air, and based on this the expanded uncertainty at the 95 % level was estimated to be 0.05 kg·m−3.

Bio-compounds are often thermally unstable. The densities of decomposition products often deviate from that of the pure measured component. In some cases, this allows potential decomposition to be detected by just observing density changes during the measurement. When measuring furfural, decomposition was observed at 473 K. Dihydrolevoglucosenone started to react at 423 K. The density value was stable for about the first 20 min at this temperature, but then started to increase. Therefore, the few points from the beginning of the measurement at 423 K are included in the data file, but these points were not included during regression.

2.3 Gas Saturation Measurements

A gas saturation method was used to measure the vapor pressures of 6 of the bio-compounds (2-methoxy-4-methylphenol, 2-sec-Butylphenol, 2,6-dimethoxyphenol, dihydrolevoglucosenone, levoglucosenone, and γ-valerolactone. About 10 ml of each sample was placed in a glass vessel filled with spherical glass beads, and the vessel was put in a gas chromatography oven. The oven maintained a stable temperature (fluctuations were within ± 0.01 K). A flow of nitrogen was introduced, and this gas became saturated with the vaporized compound. To maintain the flow rate of nitrogen, a flow controller (Alicat Scientific, Tucson, AZ, USA) was placed in the nitrogen inlet line. The nitrogen flow rate was measured with a bubble meter, both before and after each run (standard uncertainty of 0.039 ml·min−1, expanded uncertainty of 0.088 ml·min−1 at the 95 % level). The vessel was left in the oven for a period of time (on the order of hours). Afterwards, it was removed and weighed to determine the mass lost. The vapor pressure was then calculated based on Eq. 1
$$ P = \frac{{\frac{m}{W}}}{{\left( {\frac{m}{W} + \frac{{tVP_{atm} }}{{T_{room} R}}} \right)}} \cdot \left( {P_{atm} + \Delta P_{loss} } \right) $$
(1)
where P is the vapor pressure (Pa), m is the mass of the test chemical that leaves the cell (g), W is the molar mass of the test chemical (g·mol−1), t is the duration of the measurement (min), V is the volumetric flow rate of the carrier gas (in this case, nitrogen) in units of L·min−1, Patm is the atmospheric pressure at the place and time the experiment is carried out (Pa), Troom is room temperature (K), R is the ideal gas constant, and ΔPloss is the pressure drop over the gas saturation cell (assumed to be zero for our measurements). More details about the gas saturation method can be found from other references [32, 33].

Atmospheric pressure was taken from values measured by the Finnish Meteorological Institute (Tapiola observation station, Espoo, Finland) [25]. The cell and room temperatures were measured with calibrated Pt-100 temperature probes (Frontec) connected to a Systemteknik S2541 thermometer (Frontec). These probes had an expanded uncertainty of 0.04 K (using a coverage factor of 2).

The uncertainty of the vapor pressures were calculated using a Monte Carlo method (see ISO/IEC Guide 98-3) [34]. 8 different parameters were included that could potentially affect the vapor pressure value, including the purity of each compound. The uncertainty of those 8 parameters was used to specify a distribution for each, and values were then selected from those distributions to calculate a vapor pressure value. This was repeated 1 million times for each experimental data point. The standard uncertainty of each vapor pressure point was taken to be the standard deviation of the distribution from the Monte Carlo calculation. The calculated uncertainties can be found in the vapor pressure data file in the OSF project for this article (https://osf.io/u9amn/). The code we used for performing the uncertainty calculations can also be found in the same OSF project (https://osf.io/u9amn/).

2.4 Refractive Index Measurements

Refractive indexes were measured using a Dr. Kernchen Abbemat digital refractometer (Anton Paar, Graz, Austria), and this refractometer measures at a wavelength of 598.3 nm. Based on measurements with water at 25 °C, the standard uncertainty of the refractometer was calculated to be 0.00 034 (expanded uncertainty of 0.00 078 at the 95 % level). Reference data for water were obtained from Schiebener et al. [35].

2.5 Modeling with PC-SAFT

The PC-SAFT equation of state was used to model the properties of the bio-compounds [36]. Because all of the bio-compounds contain polar and/or associating functional groups, contributions from the dipole and associating terms were also included, as appropriate [37, 38, 39, 40, 41, 42]. When including the dipole term from Gross and Vrabec, the equation is also called the PCP-SAFT equation of state [38].

De Villiers et al. [43] showed that it can be difficult to find the best fit for polar compounds using pure component data alone. Often there is a large range of parameter values that will give good results for pure component properties, but poor results for mixtures. De Villiers et al. suggested that this could be because it is difficult to disentangle the contribution from polar interactions from the part due to dispersion forces. They proposed including VLE data with a nonpolar component when fitting the pure component parameters for polar compounds. Because such data is not available for many of the bio-compounds studied in this article, we simply set the number of dipoles (a parameter in Gross and Vrabec’s dipole term) equal to the actual number of polar functional groups in the molecule. This was the same strategy originally proposed by Gross and Vrabec [38]. The one exception was for furfural. A good fit could not be achieved unless the number of dipoles was also fitted against experimental data.

The dipole term also uses the dipole moment of the compound as a parameter. For most of the bio-compounds, the dipole moments were found in the literature [44, 45, 46, 47, 48, 49]. Levoglucosenone was the only compound for which the dipole moment could not be found. Therefore, for use as a parameter in the PC-SAFT equation, the dipole moment was set to be equal to that of dihydrolevoglucosenone, since they are structurally similar compounds.

For some of the compounds in this article PC-SAFT parameters have already been presented in the literature (2-methylfuran, [50, 51]; 2-pentanone [37, 52]; cyclopentyl methyl ether [53]; furfural [37, 54]; tetrahydrofuran [37, 55] and γ-valerolactone [56]. We have refit parameters for these compounds because we had more data to include in the regression, including the new data measured in this article. Both literature data and data from this study were used when optimizing the PC-SAFT parameters. A file containing all the data used in optimization, including references, can be obtained from the OSF page (https://osf.io/u9amn/). It should be noted that in the data from Apaev et al. [57] for 2-pentanone there seems to have been a typo for the point at 376.63 K and 687 bar (probably should have been 799.5 instead of 899.5 kg·m−3), and we made this change in our literature data file. The total number of points used in the optimization and the number of literature data points is presented in Table 4. A total of 969 new measured data points were used in the regression.
Table 4

PC-SAFT parameters obtained for the 11 bio-compounds

Compound

m

σ

ε/k

μ

nm

κAB

εAB/k

Density, ARD (%)

Vapor press., ARD (%)

Temp. range (K)

Nr. points used

Nr. lit. points

2-Methoxy-4-methylphenol

4.0723

3.5395

291.48

2.83

1

0.091 033

1017.8

0.084

6.0

288–494

192

5

2-Methylfuran

2.8077

3.4608

253.86

0.72

1

0.36

1.4

251–516

442

316

2-Pentanone

3.2373

3.5126

251.25

2.77

1

0.13

0.90

199–539

537

408

2-sec-Butylphenol

4.3601

3.6800

292.29

3.2993 × 10−6

3940.1

0.65

5.8

293–501

28

2

2,6-Dimethoxyphenol

4.5567

3.4499

299.94

2.10

2

0.075,030

1270.7

0.013

2.1

333–535

18

2

Cyclopentyl methyl ether

2.9310

3.7553

272.93

1.27

1

0.31

0.53

278–473

153

27

Dihydrolevoglucosenone

3.7546

3.3705

264.85

3.4

3

0.94

3.3

293–403

76

2

Furfural

3.5218

3.1933

291.71

3.60

0.371

0.090

1.8

251–527

332

211

Levoglucosenone

4.2036

3.1804

254.72

3.4a

3

0.69

7.8

293–403

27

0

Tetrahydrofuran

2.4371

3.5195

275.90

1.75

1

0.13

0.57

213–533

887

763

γ-Valerolactone

3.1504

3.4996

313.05

4.30

1

0.20

2.0

238–480

240

227

m is the segment number, σ is the segment diameter (Å), ε/k is the dispersion energy divided by the Boltzmann constant (K), μ is the dipole moment, nμ is the number of dipole moments, κAB is the association volume, εAB/k is the association energy divided by the Boltzmann constant (K), and ARD is average relative deviation

aNo dipole moment could be found in the literature for levoglucosenone, so for the PC-SAFT equation the dipole moment of dihydrolevoglucosenone was used

Parameters were optimized by minimizing the root mean-squared errors of the vapor pressure and density added together. Optimization was performed using the differential evolution solver implemented in the Scipy package for Python [30, 31]. The resulting PC-SAFT parameters are given in Table 3. Our code for implementing the PC-SAFT equation of state can be found on GitHub: https://github.com/zmeri/PC-SAFT.

3 Results and Discussion

3.1 Compressed Liquid Density, Liquid Vapor Pressure and Refractive Index Measurement Results

The results for the density measurement are presented in Tables 5, 6, 7, 8, 9, 10, 11, 12, 13 and 14. The results for the vapor pressure measurement are presented in Tables 15, 16, 17, 18, 19 and 20. The measurements of the refractive index of the components can be found in Table 21.
Table 5

Compressed liquid density of 2-methoxy-4-methylphenol (creosol)

Pressure (MPa)a

Temperature (K)b

Density (kg m−3)c

Pressure (MPa)a

Temperature (K)b

Density (kg m−3)c

0.940

298.15

1092.38

1.025

433.16

962.89

0.444

298.15

1092.14

0.527

433.15

962.10

1.914

298.15

1092.96

0.144

433.15

961.62

3.900

298.15

1094.10

1.509

433.15

963.22

5.886

298.15

1095.18

2.005

433.14

963.80

7.869

298.15

1096.19

2.501

433.15

964.34

9.852

298.15

1097.24

2.996

433.15

964.90

11.832

298.15

1098.23

3.493

433.15

965.46

0.943

323.16

1069.03

3.989

433.15

966.01

0.446

323.16

1068.70

4.487

433.15

966.52

1.931

323.15

1069.66

4.982

433.15

967.09

3.915

323.15

1070.89

5.478

433.14

967.66

5.900

323.15

1072.11

5.974

433.15

968.16

7.885

323.15

1073.27

1.035

433.15

962.66

9.866

323.15

1074.46

1.019

413.14

982.66

11.846

323.15

1075.60

0.536

413.14

982.20

0.955

323.15

1069.04

0.135

413.15

981.75

1.011

333.15

1059.62

1.510

413.15

983.16

0.515

333.15

1059.29

2.004

413.14

983.64

0.120

333.15

1059.04

2.499

413.14

984.16

1.500

333.15

1059.96

2.997

413.15

984.65

1.997

333.15

1060.29

3.492

413.15

985.12

2.490

333.15

1060.62

3.990

413.15

985.63

2.989

333.15

1060.95

4.485

413.15

986.10

3.483

333.15

1061.28

4.984

413.14

986.63

3.980

333.15

1061.61

5.480

413.14

987.09

4.476

333.15

1061.89

5.976

413.14

987.61

4.975

333.15

1062.22

1.030

413.15

982.64

5.471

333.15

1062.55

1.028

298.15

1092.76

5.967

333.15

1062.88

0.540

298.15

1092.48

1.011

333.15

1059.67

0.145

298.15

1092.27

1.030

293.15

1097.17

1.514

298.15

1093.06

0.538

293.15

1096.88

2.011

298.15

1093.34

0.135

293.15

1096.63

2.506

298.15

1093.63

1.512

293.15

1097.51

3.003

298.15

1093.87

2.009

293.15

1097.75

3.499

298.15

1094.15

2.504

293.15

1098.04

3.996

298.15

1094.44

3.003

293.15

1098.28

4.490

298.15

1094.72

3.497

293.15

1098.56

4.988

298.15

1094.95

3.994

293.15

1098.80

5.485

298.15

1095.23

3.993

293.15

1098.75

5.981

298.15

1095.52

4.490

293.15

1099.03

1.040

298.15

1092.77

4.988

293.15

1099.26

0.536

393.14

1001.91

5.485

293.15

1099.54

0.144

393.14

1001.52

5.982

293.15

1099.83

1.020

393.14

1002.33

1.037

293.15

1097.12

1.510

393.14

1002.80

1.038

313.16

1078.42

2.007

393.15

1003.21

0.543

313.16

1078.14

2.503

393.15

1003.68

0.134

313.15

1077.84

3.002

393.15

1004.10

1.511

313.15

1078.72

3.496

393.15

1004.52

1.511

313.15

1078.72

3.992

393.14

1005.00

2.008

313.15

1079.01

4.488

393.14

1005.42

2.504

313.15

1079.29

5.482

393.14

1006.31

3.001

313.15

1079.63

4.987

393.14

1005.84

3.497

313.15

1079.91

5.978

393.14

1006.73

3.994

313.15

1080.19

1.032

393.15

1002.32

4.488

313.15

1080.48

0.531

453.16

942.46

4.989

313.15

1080.76

0.144

453.16

941.94

5.483

313.15

1081.09

1.017

453.16

943.11

5.980

313.15

1081.37

1.510

453.16

943.71

1.040

313.15

1078.38

2.007

453.15

944.38

1.022

353.16

1040.71

2.502

453.15

944.98

0.540

353.16

1040.33

2.997

453.16

945.62

0.135

353.15

1040.04

3.494

453.16

946.27

1.510

353.15

1041.04

3.991

453.16

946.87

2.006

353.15

1041.42

4.486

453.16

947.48

2.503

353.15

1041.80

4.985

453.16

948.08

3.001

353.15

1042.13

5.481

453.16

948.69

3.497

353.15

1042.51

5.975

453.15

949.30

3.991

353.15

1042.84

1.036

453.15

943.13

4.489

353.15

1043.21

1.019

473.16

922.11

4.987

353.15

1043.59

0.537

473.15

921.38

5.483

353.15

1043.92

1.032

473.15

922.41

5.980

353.15

1044.24

1.512

473.16

922.95

1.034

353.15

1040.67

2.007

473.15

923.65

1.017

373.16

1021.60

2.501

473.15

924.39

0.533

373.16

1021.17

2.999

473.15

925.09

0.133

373.15

1020.84

3.495

473.15

925.78

1.510

373.15

1021.98

3.993

473.15

926.53

2.007

373.15

1022.41

4.487

473.15

927.17

2.503

373.15

1022.78

4.986

473.15

927.87

2.999

373.15

1023.20

5.481

473.15

928.57

3.496

373.16

1023.57

5.977

473.15

929.27

3.992

373.15

1023.96

0.538

473.15

921.53

4.489

373.15

1024.34

1.030

473.15

922.46

4.986

373.15

1024.76

   

5.481

373.15

1025.13

   

5.977

373.15

1025.55

   

1.031

373.15

1021.56

   

aThe standard uncertainty of the pressure is u(pressure) = 0.0031 MPa (expanded uncertainty u(pressure) = 0.0063 MPa at the 95 % level)

bStandard uncertainty of temperature u(temperature) = 0.1 K (expanded uncertainty u(temperature) = 0.2 K at the 95 % level)

cStandard uncertainty of the density is 0.66 kg·m−3 (expanded uncertainty of 1.3 kg·m−3 at the 95 % level)

Table 6

Compressed liquid density of 2-Methylfuran

Pressure (MPa)a

Temperature (K)b

Density (kg m−3)c

Pressure (MPa)a

Temperature (K)b

Density (kg m−3)c

0.495

298.14

909.96

5.922

373.15

823.16

0.095

298.14

909.46

6.912

373.15

824.89

0.989

298.14

910.40

7.899

373.15

826.62

1.974

298.14

911.38

8.885

373.15

828.29

2.963

298.14

912.40

9.872

373.15

829.92

3.952

298.14

913.42

10.856

373.15

831.50

4.940

298.14

914.39

11.842

373.15

833.12

5.929

298.14

915.36

1.004

398.15

777.14

6.916

298.14

916.32

0.612

398.15

776.12

7.904

298.14

917.28

1.973

398.16

779.62

8.891

298.14

918.25

2.961

398.16

782.07

9.877

298.14

919.16

3.946

398.16

784.46

10.860

298.14

920.11

4.936

398.15

786.82

11.847

298.14

921.02

5.924

398.15

789.07

0.500

293.15

915.84

6.912

398.15

791.32

0.088

293.14

915.46

7.898

398.15

793.47

0.995

293.15

916.39

8.887

398.15

795.57

1.972

293.15

917.36

9.874

398.16

797.61

2.960

293.15

918.33

10.859

398.16

799.62

3.949

293.15

919.30

11.843

398.16

801.52

4.938

293.15

920.22

1.001

298.16

910.52

5.926

293.15

921.19

0.989

423.15

736.05

6.913

293.15

922.11

11.848

423.14

768.03

7.899

293.15

923.02

11.845

423.14

768.38

8.886

293.15

923.93

10.881

423.15

766.03

9.874

293.15

924.85

11.843

423.15

768.37

10.858

293.15

925.75

9.898

423.15

763.51

11.843

293.15

926.61

8.918

423.15

760.94

0.508

323.16

879.22

7.934

423.16

758.25

0.092

323.15

878.68

6.948

423.16

755.49

0.986

323.15

879.81

5.963

423.16

752.58

11.847

323.15

892.53

4.967

423.15

749.60

10.882

323.15

891.48

3.982

423.15

746.50

9.902

323.15

890.43

2.990

423.15

743.21

8.921

323.15

889.33

2.001

423.16

739.81

7.935

323.15

888.22

1.005

423.16

736.18

6.951

323.15

887.07

1.009

423.15

736.15

5.959

323.15

885.91

11.843

423.15

768.40

4.977

323.15

884.75

1.583

448.15

691.16

3.984

323.15

883.55

11.844

448.14

733.04

2.994

323.15

882.34

10.867

448.15

729.98

1.998

323.15

881.12

9.895

448.15

726.76

0.512

348.15

847.10

8.916

448.15

723.39

11.845

348.15

863.31

7.931

448.15

719.79

10.879

348.15

862.07

6.947

448.15

716.05

9.896

348.15

860.78

5.956

448.14

712.07

8.916

348.15

859.44

4.974

448.15

707.93

7.933

348.15

858.09

3.982

448.15

703.52

6.948

348.15

856.75

2.992

448.15

698.73

5.961

348.15

855.31

2.000

448.14

693.56

4.971

348.15

853.91

1.597

448.15

691.36

3.976

348.15

852.42

2.277

473.15

637.03

2.993

348.15

850.97

10.878

473.15

690.57

1.995

348.15

849.42

11.843

473.15

694.63

1.006

348.15

847.88

9.898

473.15

686.19

0.212

348.15

846.65

8.910

473.14

681.52

0.505

373.15

812.92

7.933

473.16

676.50

0.406

373.15

812.69

6.947

473.15

671.08

0.985

373.15

813.84

5.961

473.15

665.28

1.971

373.15

815.77

4.969

473.15

658.86

2.958

373.15

817.69

3.982

473.15

651.78

3.946

373.15

819.52

2.990

473.15

643.66

4.935

373.15

821.34

2.287

473.15

637.22

aThe standard uncertainty of the pressure is u(pressure) = 0.0031 MPa (expanded uncertainty u(pressure) = 0.0063 MPa at the 95 % level)

bStandard uncertainty of temperature u(temperature) = 0.1 K (expanded uncertainty u(temperature) = 0.2 K at the 95 % level)

cStandard uncertainty of the density is 0.11 kg·m−3 (expanded uncertainty of 0.21 kg·m−3 at the 95 % level)

Table 7

Compressed liquid density of 2-pentanone

Pressure (MPa)a

Temperature (K)b

Density (kg·m−3)c

Pressure (MPa)a

Temperature (K)b

Density (kg·m−3)c

0.495

298.14

801.70

7.900

373.15

736.41

0.095

298.14

801.35

8.889

373.15

737.74

0.987

298.15

802.14

9.874

373.15

739.02

1.973

298.15

803.01

10.859

373.15

740.25

2.962

298.15

803.87

11.845

373.15

741.48

3.951

298.15

804.74

0.496

298.15

801.74

4.939

298.15

805.56

0.492

398.16

697.96

5.926

298.15

806.42

0.305

398.16

697.60

6.917

298.15

807.23

11.847

398.16

717.17

7.903

298.15

808.05

10.869

398.15

715.75

8.890

298.15

808.86

9.905

398.15

714.30

9.877

298.15

809.62

8.923

398.15

712.78

10.862

298.15

810.43

7.941

398.15

711.22

11.845

298.15

811.18

6.953

398.15

709.56

0.497

293.15

806.56

5.965

398.15

707.89

0.091

293.15

806.21

4.979

398.15

706.18

0.986

293.15

806.95

3.987

398.15

704.43

1.973

293.15

807.82

2.995

398.15

702.68

2.962

293.15

808.64

2.004

398.15

700.88

3.949

293.15

809.46

1.011

398.15

698.97

4.940

293.15

810.28

0.999

423.15

669.40

5.927

293.15

811.09

0.515

423.16

668.10

6.915

293.15

811.86

11.848

423.15

692.13

7.902

293.15

812.67

10.883

423.15

690.43

8.889

293.15

813.44

9.903

423.14

688.59

9.874

293.15

814.20

8.920

423.15

686.69

10.860

293.15

814.96

7.938

423.15

684.75

11.844

293.15

815.71

6.951

423.14

682.79

0.509

323.16

777.26

5.966

423.14

680.75

0.086

323.15

776.82

4.979

423.15

678.61

0.987

323.15

777.75

3.986

423.15

676.39

1.973

323.15

778.81

2.997

423.15

674.17

2.961

323.15

779.82

2.003

423.14

671.87

3.949

323.15

780.83

1.005

423.14

669.41

4.940

323.15

781.79

0.987

448.16

636.76

5.927

323.15

782.80

0.754

448.16

635.93

6.914

323.15

783.75

11.847

448.15

665.96

7.901

323.15

784.71

10.879

448.16

663.78

8.889

323.15

785.66

9.903

448.16

661.56

9.875

323.15

786.56

8.919

448.16

659.21

10.859

323.15

787.47

7.937

448.16

656.81

11.845

323.15

788.37

6.952

448.15

654.33

0.512

348.15

752.02

5.957

448.15

651.75

0.086

348.15

751.49

4.976

448.16

649.05

0.985

348.15

752.60

3.977

448.16

646.18

1.972

348.15

753.85

2.993

448.16

643.21

2.959

348.15

755.05

2.003

448.15

640.12

3.948

348.15

756.24

1.010

448.15

636.87

4.939

348.15

757.44

1.099

473.16

600.03

5.925

348.15

758.59

11.849

473.15

638.34

6.913

348.15

759.73

9.899

473.15

632.90

7.902

348.15

760.87

7.939

473.15

626.90

8.888

348.15

761.97

5.965

473.15

620.25

9.876

348.15

763.06

3.986

473.14

612.91

10.858

348.15

764.15

1.997

473.15

604.46

11.845

348.15

765.20

1.104

473.15

600.13

0.502

373.15

725.68

1.101

473.15

600.09

0.114

373.15

725.04

2.961

473.15

608.54

0.987

373.15

726.44

4.936

473.15

616.46

1.972

373.15

727.92

6.913

473.14

623.50

2.959

373.15

729.40

8.889

473.16

629.85

3.948

373.15

730.84

10.859

473.15

635.67

4.938

373.15

732.27

1.107

473.15

600.13

5.925

373.15

733.70

0.496

298.15

801.73

6.914

373.15

735.08

   

aThe standard uncertainty of the pressure is u(pressure) = 0.0031 MPa (expanded uncertainty u(pressure) = 0.0063 MPa at the 95 % level)

bStandard uncertainty of temperature u(temperature) = 0.1 K (expanded uncertainty u(temperature) = 0.2 K at the 95 % level)

cStandard uncertainty of the density is 0.21 kg·m−3 (expanded uncertainty of 0.41 kg·m−3 at the 95 % level)

Table 8

Liquid density of 2-sec-butylphenol at atmospheric pressure

Pressure (MPa)a

Temperature (K)b

Density (kg·m−3)c

0.102

293.15

981.32

0.103

298.14

977.22

0.103

298.16

977.25

0.103

313.16

965.03

0.103

333.16

948.54

0.103

353.16

931.70

0.103

373.16

914.64

0.103

393.15

897.29

0.103

413.16

879.65

0.103

433.16

861.73

0.103

453.15

843.35

0.103

473.16

824.44

aThe standard uncertainty of the pressure is u(pressure) = 0.0031 MPa (expanded uncertainty u(pressure) = 0.0063 MPa at the 95 % level)

bStandard uncertainty of temperature u(temperature) = 0.1 K (expanded uncertainty u(temperature) = 0.2 K at the 95 % level)

cStandard uncertainty of the density is 0.11 kg·m−3 (expanded uncertainty of 0.22 kg·m−3 at the 95 % level)

Table 9

Liquid density of 2,6-dimethoxyphenol (syringol) at atmospheric pressure

Pressure (MPa)a

Temperature (K)b

Density (kg m−3)c

0.101

333.16

1158.57

0.101

343.16

1148.88

0.101

353.16

1139.15

0.101

363.15

1129.40

0.101

373.16

1119.48

0.101

383.16

1109.63

aThe standard uncertainty of the pressure is u(pressure) = 0.0031 MPa (expanded uncertainty u(pressure) = 0.0063 MPa at the 95 % level)

bStandard uncertainty of temperature u(temperature) = 0.1 K (expanded uncertainty u(temperature) = 0.2 K at the 95 % level)

cStandard uncertainty of the density is 0.30 kg·m−3 (expanded uncertainty of 0.60 kg·m−3 at the 95 % level)

Table 10

Compressed liquid density of cyclopentyl methyl ether

Pressure (MPa)a

Temperature (K)b

Density (kg·m−3)c

Pressure (MPa)a

Temperature (K)b

Density (kg·m−3)c

0.505

298.14

858.52

5.926

373.15

790.28

0.099

298.15

858.12

6.915

373.15

791.61

0.990

298.15

858.91

7.900

373.15

792.89

1.979

298.14

859.73

8.889

373.15

794.18

2.965

298.14

860.56

9.876

373.15

795.41

3.956

298.14

861.38

10.859

373.15

796.64

4.943

298.14

862.20

11.845

373.15

797.83

5.931

298.14

863.01

0.512

398.15

755.18

6.920

298.14

863.78

0.310

398.15

754.82

7.907

298.14

864.54

0.988

398.15

756.04

8.894

298.14

865.35

1.973

398.15

757.80

9.882

298.14

866.11

2.959

398.15

759.56

10.867

298.14

866.87

3.950

398.15

761.22

11.851

298.14

867.58

4.940

398.15

762.84

0.514

293.14

863.31

5.927

398.15

764.46

0.098

293.15

862.95

6.916

398.15

766.08

0.988

293.15

863.69

7.902

398.15

767.59

11.853

293.15

872.11

8.890

398.15

769.16

10.886

293.15

871.40

9.876

398.15

770.62

9.908

293.15

870.69

10.860

398.15

772.04

8.927

293.15

869.98

11.845

398.15

773.46

7.940

293.15

869.22

0.496

298.15

858.51

6.955

293.15

868.45

1.002

423.15

726.95

5.969

293.15

867.69

0.506

423.16

725.80

4.977

293.15

866.92

11.851

423.16

748.37

3.982

293.15

866.15

10.889

423.15

746.73

3.000

293.15

865.33

9.909

423.15

744.99

2.003

293.15

864.56

8.921

423.15

743.19

0.513

323.16

834.09

7.943

423.16

741.38

0.097

323.15

833.70

6.959

423.16

739.49

0.988

323.15

834.58

5.964

423.16

737.54

1.974

323.15

835.55

4.983

423.15

735.57

2.962

323.15

836.56

3.987

423.15

733.54

3.951

323.15

837.52

2.997

423.15

731.41

4.942

323.15

838.43

2.002

423.16

729.21

5.926

323.15

839.39

0.700

448.15

694.30

6.916

323.15

840.30

11.852

448.15

722.29

7.902

323.15

841.20

10.890

448.14

720.28

8.889

323.15

842.11

9.906

448.14

718.20

9.876

323.15

843.01

8.927

448.15

716.02

10.861

323.15

843.92

7.944

448.15

713.76

11.844

323.15

844.77

6.957

448.15

711.40

0.509

348.15

808.94

5.968

448.15

708.95

0.092

348.15

808.41

4.982

448.15

706.45

0.987

348.15

809.47

3.983

448.14

703.81

11.852

348.15

821.55

2.997

448.15

701.12

10.886

348.15

820.55

1.996

448.15

698.29

9.905

348.15

819.56

1.010

448.15

695.32

8.920

348.15

818.51

0.710

448.15

694.40

7.942

348.15

817.42

11.851

473.14

694.93

6.955

348.15

816.37

1.506

473.15

661.90

5.963

348.15

815.27

1.011

473.15

659.73

4.980

348.15

814.17

1.980

473.15

663.68

3.986

348.15

813.02

2.965

473.15

667.54

2.994

348.15

811.87

3.951

473.15

671.20

2.004

348.15

810.73

4.940

473.15

674.68

0.513

373.16

782.72

5.928

473.15

677.96

0.107

373.16

782.14

6.916

473.15

681.07

0.988

373.16

783.44

7.904

473.15

684.07

1.971

373.16

784.83

8.889

473.15

686.99

2.964

373.16

786.27

9.877

473.15

689.76

3.948

373.15

787.60

10.861

473.15

692.39

4.940

373.15

788.99

11.846

473.15

694.97

aThe standard uncertainty of the pressure is u(pressure) = 0.0031 MPa (expanded uncertainty u(pressure = 0.0063 MPa at the 95 % level)

bStandard uncertainty of temperature u(temperature) = 0.1 K (expanded uncertainty u(temperature) = 0.2 K at the 95 % level)

cStandard uncertainty of the density is 0.10 kg m−3 (expanded uncertainty of 0.20 kg m−3 at the 95 % level)

Table 11

Compressed liquid density of dihydrolevoglucosenone

Pressure (MPa)a

Temperature (K)b

Density (kg·m−3)c

Pressure (MPa)a

Temperature (K)b

Density (kg·m−3)c

0.090

293.15

1250.75

15.756

348.15

1207.18

3.943

293.15

1252.88

0.088

348.15

1196.86

9.868

293.15

1256.00

1.953

348.15

1198.15

13.804

293.15

1257.92

3.930

348.15

1199.47

15.764

293.15

1258.89

5.907

348.15

1200.83

5.919

293.15

1253.91

7.882

348.15

1202.14

7.894

293.15

1254.94

5.906

373.15

1176.75

11.837

293.15

1256.99

1.978

373.15

1173.80

1.967

293.15

1251.77

3.928

373.15

1175.25

0.093

298.15

1245.77

7.881

373.15

1178.24

0.984

298.15

1246.32

0.086

373.15

1172.28

9.872

298.15

1251.16

9.856

373.15

1179.67

13.808

298.15

1253.14

11.824

373.15

1181.11

15.768

298.15

1254.11

13.791

373.15

1182.49

1.947

298.15

1246.95

15.754

373.15

1183.87

1.948

298.15

1247.00

1.952

373.16

1173.74

1.969

298.15

1246.85

5.902

398.15

1152.51

3.946

298.15

1247.95

7.879

398.15

1154.19

5.923

298.15

1249.03

9.852

398.15

1155.82

7.897

298.15

1250.10

11.823

398.15

1157.44

11.843

298.15

1252.16

13.789

398.15

1159.02

0.084

323.15

1221.30

15.749

398.15

1160.55

1.957

323.15

1222.51

1.976

398.15

1149.35

3.933

323.15

1223.70

3.926

398.15

1150.87

5.912

323.15

1224.92

1.949

398.16

1149.14

7.886

323.15

1226.08

0.082

398.16

1147.60

9.860

323.15

1227.24

1.958

423.15

1124.40

11.830

323.15

1228.38

0.073

423.14

1122.74

13.795

323.15

1229.51

0.091

423.15

1122.77

15.760

323.15

1230.58

1.950

423.16

1124.38

9.856

348.15

1203.43

15.756

423.16

1137.14

11.827

348.15

1204.67

9.888

423.14

1131.94

13.792

348.15

1205.96

1.971

423.14

1124.61

aThe standard uncertainty of the pressure is u(pressure) = 0.0031 MPa (expanded uncertainty u(pressure) = 0.0063 MPa at the 95 % level)

bStandard uncertainty of temperature u(temperature) = 0.1 K (expanded uncertainty u(temperature) = 0.2 K at the 95 % level)

cStandard uncertainty of the density is 0.25 kg·m−3 (expanded uncertainty of 0.51 kg·m−3 at the 95 % level)

Table 12

Compressed liquid density of furfural

Pressure (MPa)a

Temperature (K)b

Density (kg·m−3)c

Pressure (MPa)a

Temperature (K)b

Density (kg·m−3)c

0.497

293.15

1160.04

1.974

373.15

1074.66

0.092

293.15

1159.79

2.959

373.15

1075.61

0.987

293.15

1160.38

3.949

373.15

1076.51

1.973

293.15

1161.01

4.940

373.15

1077.41

2.961

293.15

1161.64

5.929

373.15

1078.35

3.950

293.15

1162.22

6.916

373.15

1079.25

4.940

293.15

1162.84

7.903

373.15

1080.14

5.930

293.15

1163.46

8.890

373.15

1080.99

6.920

293.15

1164.07

9.878

373.15

1081.88

7.905

293.15

1164.64

10.863

373.15

1082.73

8.894

293.15

1165.24

11.849

373.15

1083.57

9.881

293.15

1165.85

0.510

373.15

1073.27

10.865

293.15

1166.40

0.495

398.16

1044.93

11.851

293.15

1167.00

0.092

398.16

1044.54

0.495

298.14

1154.82

0.987

398.15

1045.45

0.093

298.14

1154.52

11.856

398.15

1056.72

0.988

298.15

1155.06

10.874

398.15

1055.78

1.973

298.15

1155.69

9.894

398.15

1054.84

2.962

298.15

1156.32

8.912

398.15

1053.80

3.952

298.15

1156.99

7.928

398.15

1052.78

4.941

298.15

1157.61

6.942

398.15

1051.79

5.929

298.15

1158.23

5.954

398.15

1050.80

6.917

298.15

1158.84

4.966

398.15

1049.76

7.904

298.15

1159.45

3.974

398.15

1048.73

8.893

298.15

1160.06

2.983

398.15

1047.64

9.878

298.15

1160.67

1.990

398.15

1046.59

10.864

298.15

1161.27

0.518

398.15

1044.99

11.849

298.15

1161.82

0.494

423.16

1015.70

0.514

298.15

1154.81

0.108

423.14

1015.20

0.499

298.15

1154.81

0.986

423.14

1016.34

0.496

323.15

1128.08

11.854

423.14

1029.37

0.089

323.15

1127.78

9.892

423.15

1027.14

0.986

323.15

1128.47

7.925

423.15

1024.83

1.974

323.15

1129.14

5.953

423.14

1022.50

2.962

323.15

1129.86

3.975

423.14

1020.10

3.951

323.15

1130.53

0.515

423.15

1015.76

4.940

323.15

1131.24

1.976

423.15

1017.54

5.929

323.15

1131.96

2.964

423.15

1018.77

6.917

323.15

1132.62

4.941

423.14

1021.23

7.903

323.15

1133.32

6.917

423.14

1023.63

8.890

323.15

1133.98

8.891

423.15

1025.96

9.878

323.15

1134.68

10.863

423.15

1028.22

10.862

323.15

1135.33

0.514

423.16

1015.74

11.850

323.15

1135.98

0.491

448.15

985.23

0.495

348.16

1100.92

0.298

448.14

984.99

0.087

348.15

1100.58

11.852

448.15

1001.25

0.988

348.15

1101.31

9.891

448.15

998.65

1.971

348.15

1102.12

7.924

448.15

996.02

2.961

348.15

1102.93

5.951

448.15

993.24

3.950

348.15

1103.74

3.970

448.15

990.43

4.940

348.15

1104.55

1.987

448.14

987.54

5.928

348.15

1105.31

0.514

448.15

985.33

6.917

348.15

1106.11

0.513

448.15

985.28

7.904

348.15

1106.91

0.988

448.14

986.04

8.891

348.15

1107.66

2.962

448.15

988.93

9.879

348.15

1108.41

4.940

448.15

991.79

10.863

348.15

1109.16

6.917

448.15

994.56

11.849

348.15

1109.91

8.892

448.15

997.29

0.500

373.16

1073.32

10.863

448.14

999.94

0.091

373.15

1072.93

0.509

448.15

985.37

0.988

373.16

1073.70

   

aThe standard uncertainty of the pressure is u(pressure) = 0.0031 MPa (expanded uncertainty u(pressure) = 0.0063 MPa at the 95 % level)

bStandard uncertainty of temperature u(temperature) = 0.1 K (expanded uncertainty u(temperature) = 0.2 K at the 95 % level)

cStandard uncertainty of the density is 0.24 kg·m−3 (expanded uncertainty of 0.47 kg·m−3 at the 95 % level)

Table 13

Liquid density of levoglucosenone

Pressure (MPa)a

Temperature (K)b

Density (kg m−3)c

0.100

293.15

1303.6

0.100

298.15

1298.6

0.100

313.15

1283.5

0.100

328.15

1268.4

0.100

343.15

1253.3

0.100

353.15

1243.3

0.100

363.15

1233.2

0.100

293.15

1303.6

0.100

298.15

1298.6

0.100

313.15

1283.5

0.100

328.15

1268.4

0.100

343.15

1253.3

0.100

353.15

1243.3

0.100

363.15

1233.2

0.100

298.15

1298.6

aThe standard uncertainty of the pressure is u(pressure) = 0.0031 MPa (expanded uncertainty u(pressure) = 0.0063 MPa at the 95 % level)

bStandard uncertainty of temperature u(temperature) = 0.1 K (expanded uncertainty u(temperature = 0.2 K at the 95 % level)

cStandard uncertainty of the density is 1.7 kg·m−3 (expanded uncertainty of 3.4 kg·m−3 at the 95 % level)

Table 14

Compressed liquid density of tetrahydrofuran

Pressure (MPa)a

Temperature (K)b

Density (kg·m−3)c

Pressure (MPa)a

Temperature (K)b

Density (kg·m−3)c

0.402

298.15

882.38

9.901

348.15

837.19

0.099

298.15

882.02

8.920

348.15

836.10

0.992

298.15

882.81

7.933

348.15

834.96

11.854

298.15

891.84

6.953

348.15

833.81

10.874

298.15

891.09

5.962

348.15

832.61

9.893

298.15

890.29

4.979

348.15

831.47

8.909

298.15

889.53

3.987

348.15

830.22

7.925

298.15

888.73

2.997

348.15

829.02

6.941

298.15

887.92

2.006

348.15

827.77

5.954

298.15

887.11

0.215

348.15

825.49

4.965

298.15

886.24

0.988

373.15

796.10

3.977

298.15

885.42

1.974

373.16

797.63

2.986

298.15

884.55

2.960

373.15

799.18

1.994

298.15

883.68

3.948

373.15

800.67

0.513

298.15

882.42

4.937

373.15

802.14

0.502

293.15

887.82

5.925

373.15

803.62

0.111

293.15

887.47

6.910

373.15

805.06

11.854

293.15

896.95

7.898

373.15

806.44

0.494

293.15

887.77

8.886

373.15

807.82

11.854

293.15

896.96

9.874

373.15

809.20

10.892

293.15

896.25

10.857

373.15

810.53

9.910

293.15

895.50

11.842

373.15

811.81

1.013

293.14

888.32

0.512

373.15

795.44

1.986

293.15

889.09

0.313

373.15

795.02

2.968

293.15

889.92

0.500

398.16

762.57

3.953

293.15

890.74

1.974

398.15

765.55

4.940

293.15

891.56

11.848

398.15

783.16

5.928

293.15

892.37

10.867

398.15

781.60

6.917

293.15

893.14

9.898

398.15

780.08

7.904

293.15

893.95

8.916

398.16

778.41

8.890

293.15

894.70

7.933

398.16

776.74

0.512

323.15

854.73

6.943

398.16

774.98

0.103

323.15

854.29

5.965

398.15

773.22

0.986

323.15

855.22

4.975

398.15

771.41

11.852

323.15

865.93

3.985

398.15

769.55

10.885

323.15

865.03

2.995

398.15

767.65

9.905

323.15

864.13

1.007

398.16

763.67

8.924

323.15

863.18

0.899

423.15

727.70

7.940

323.15

862.23

0.990

423.16

727.96

6.949

323.15

861.28

11.847

423.16

753.18

5.970

323.15

860.32

2.002

423.15

730.83

4.978

323.15

859.32

2.969

423.16

733.24

3.987

323.15

858.31

3.954

423.16

735.70

3.001

323.15

857.30

4.940

423.16

738.08

2.002

323.15

856.28

5.929

423.15

740.47

1.998

443.14

699.53

6.914

423.15

742.75

2.972

443.14

702.90

7.901

423.15

744.94

11.849

443.15

727.80

8.886

423.16

747.10

3.986

443.15

706.29

9.879

423.16

749.19

4.957

443.15

709.28

10.857

423.15

751.20

5.940

443.15

712.17

2.094

473.16

644.15

6.925

443.15

715.01

11.846

473.15

686.73

7.909

443.14

717.78

10.872

473.15

683.48

8.895

443.15

720.41

9.898

473.15

680.08

9.880

443.15

722.97

8.910

473.15

676.45

10.865

443.15

725.44

7.932

473.15

672.68

1.393

443.15

697.40

6.948

473.15

668.67

1.017

298.15

882.85

5.961

473.15

664.38

0.509

348.15

825.84

4.975

473.15

659.81

0.992

348.15

826.47

3.982

473.15

654.91

11.846

348.15

839.27

2.985

473.15

649.50

10.882

348.15

838.28

2.494

473.15

646.62

aThe standard uncertainty of the pressure is u(pressure) = 0.0031 MPa (expanded uncertainty u(pressure) = 0.0063 MPa at the 95 % level)

bStandard uncertainty of temperature u(temperature) = 0.1 K (expanded uncertainty u(temperature) = 0.2 K at the 95 % level)

cStandard uncertainty of the density is 0.1 kg·m−3 (expanded uncertainty of 0.2 kg·m−3 at the 95 % level)

Table 15

Vapor pressure of liquid 2-methoxy-4-methylphenol

Temperature Ka

Vapor pressure Liquid Pa

Expanded uncertainty of vapor pressure at 95 % level Pa

298.22

9.3

1.0

303.24

16.1

1.4

313.25

31.7

3.0

323.24

81.8

6.4

323.25

82.1

6.2

333.27

143.0

6.3

343.22

274.5

9.2

353.27

476

20

363.22

807

42

373.21

1533

58

383.22

2280

119

393.16

3520

122

403.20

5320

141

aStandard uncertainty of the temperature u(T) = 0.04 K

Table 16

Vapor pressure of liquid 2-sec-butylphenol

Temperature Ka

Vapor pressure liquid (Pa)

Expanded uncertainty of vapor pressure at 95 % level (Pa)

298.21

4.74

0.74

303.24

8.5

1.3

313.25

18.4

2.5

323.25

49.4

5.5

333.29

94.2

11

343.23

231

24

343.24

226.6

6.9

353.28

449

23

363.23

663

21

363.26

659

35

373.25

1097

60

383.31

1868

96

393.25

2940

126

403.25

4570

139

aStandard uncertainty of the temperature u(T) = 0.04 K

Table 17

Vapor pressure of liquid 2,6-dimethoxyphenol (syringol)

Temperature Ka

Vapor pressure liquid (Pa)

Expanded uncertainty of vapor pressure at 95 % level (Pa)

333.28

15.8

1.5

333.30

14.3

2.0

343.22

31.7

1.8

353.27

64.0

6.0

363.25

122.3

2.8

373.24

233

10

383.28

401

24

393.25

722

32

403.26

1123

42

413.16

1884

64

aStandard uncertainty of the temperature u(T) = 0.04 K

Table 18

Vapor pressure of liquid Dihydrolevoglucosenone (cyrene)

Temperature Ka

Vapor pressure liquid (Pa)

Expanded uncertainty of vapor pressure at 95 % level (Pa)

298.26

14.4

2.4

308.31

28.2

2.5

318.24

51.5

8.0

328.27

116.9

6.1

333.32

157.3

7.0

338.27

219.4

7.4

343.26

294

15

343.26

288

12

353.25

506.1

7.1

363.26

842

29

373.24

1324

69

378.23

1780

111

383.26

2133

93

393.18

3490

202

403.16

5170

229

*Standard uncertainty of the temperature u(T) = 0.04 K

Table 19

Vapor pressure of liquid Levoglucosenone

Temperature (K)a

Vapor pressure liquid (Pa)

Expanded uncertainty of vapor pressure at 95 % level (Pa)

298.26

6.2

1.7

303.25

10.0

2.3

313.26

26.0

4.6

323.25

42.2

7.8

333.29

90.3

8.6

343.24

205

11

353.26

374

28

363.27

621

36

373.27

909

57

383.29

1502

85

393.26

2450

122

403.30

3480

137

aStandard uncertainty of the temperature u(T) = 0.04 K

Table 20

Vapor pressure of liquid γ-valerolactone

Temperature (K)a

Vapor pressure liquid (Pa)

Expanded uncertainty of vapor pressure at 95 % level (Pa)

298.23

43.6

3.1

303.20

64.8

3.2

313.25

136.7

7.0

323.25

244

12

333.29

453

21

343.18

763

22

343.28

791

38

353.26

1293

29

363.25

2060

61

373.17

3120

173

383.12

2280

144

393.08

3520

223

403.15

5320

346

aStandard uncertainty of the temperature u(T) = 0.04 K

Table 21

Refractive index of liquid Dihydrolevoglucosenone (cyrene), γ-valerolactone, 2-methoxy-4-methylphenol (creosol), 2-sec-butylphenol, Levoglucosenone, 2,6-dimethoxyphenol (syringol), Tetrahydrofuran, 2-pentanone, 2-methylfuran at 0.10 MPa

Temperature Ka

Refractive indexb

Dihydrolevoglucosenone (cyrene)

γ-Valerolactone

2-Methoxy-4-methylphenol (creosol)

2-sec-Butylphenol

Levoglucosenone

2,6-Dimethoxyphenol (syringol)

Tetrahydrofuran

2-Pentanone

2-Methylfuran

293.15

1.4732

1.4333

1.5373

1.5228

1.5065

 

1.4073

1.3903

1.4332

298.15

1.4712

1.4313

1.5348

1.5205

     

303.15

1.4691

1.4292

1.5323

1.5171

1.5022

    

308.15

1.4671

1.4272

1.5299

1.5146

     

313.15

1.4651

1.4252

1.5274

1.5113

1.4980

    

318.15

1.4631

1.4231

1.525

1.5086

     

323.15

1.4611

1.4211

1.5225

1.5062

1.4938

    

328.15

1.4592

1.4191

1.5200

1.5039

 

1.5365

   

333.15

1.4571

1.4170

1.5176

1.5018

1.4896

1.5344

   

338.15

  

1.5151

1.5000

 

1.5320

   

343.15

  

1.5126

1.4980

1.4854

1.5296

   

Standard uncertainty of the pressure is 0.01 MPa

aStandard uncertainty of the temperature is 0.03 K

bStandard uncertainty of liquid refractive index: u(refractive index) = 0.00 034, (expanded uncertainty of 0.00 078 at the 95 % level)

3.2 Comparison with Literature Values

A lot of literature data is available for tetrahydrofuran, and our experimental density values matched well with most of the literature values. For instance, at 293.15 K the value we measured was close to the mean of the literature data (see Table 22) and was well within the standard deviation of the literature values (0.33 kg·m−3, with outliers removed).
Table 22

Comparison of experimental density values from this study with literature values

Compound

Density at 293.15 K (kg·m−3)

References

This work

Literaturea

2-Methoxy-4-methylphenol

1096.6 ± 1.3

1090.05

[76]

2-Methylfuran

915.46 ± 0.1

915.31 ± 0.48

[77, 78, 79, 80, 81]

2-Pentanone

806.21 ± 0.41

807.80 ± 0.56

[82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100]

2-sec-Butylphenol

977.24 ± 0.22b

980.4b

[101]

2,6-Dimethoxyphenol

1158.57 ± 0.6c

 

Cyclopentyl methyl ether

862.95 ± 0.2

862.80

860.43

[102]

[103]

Dihydrolevoglucosenone

1250.75 ± 0.51

1250

1251.7

[3]

[44]

Furfural

1159.79 ± 0.47

1160.10 ± 0.45

[79, 93, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113]

Levoglucosenone

1303.6 ± 3.4

 

Tetrahydrofuran

887.47 ± 0.2

887.57 ± 0.14

[58, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129]

γ-Valerolactone

1054.61 ± 1.4

[56, 67, 68, 130, 131, 132]

aMean of literature values, if more than two literature values were available and outliers were removed

bAt 298.15 K

cAt 333.16 K

We found seven literature sources that give compressed densities of tetrahydrofuran, and when comparing we found that the data from many of these literature sources seems to have relatively large errors [58, 59, 60, 61, 62, 63, 64]. Figure 2 compares the literature sources and values from this article, using the PC-SAFT fit for tetrahydrofuran as a reference. The points from Holzapfel et al. [58] and Sato et al. [59] aligned well with our data, as did much of the data from Govender et al. [60]. Data from Vasileva et al. [61] was in the same range as our data, but in general the deviations between the two data sets were larger than the measurement uncertainty of our data. The largest difference is 12 kg·m−3, and this occurs at 473.15 K and about 21 bar. At 293.15 K the value from Vasileva et al. is more than 7 standard deviations higher than the literature mean, and so it seems that there is a higher uncertainty in the data from Vasileva et al. The vapor pressures from Vasileva et al. also had some of the largest deviations from the PC-SAFT equation.
Fig. 2

Comparison of the literature sources that give the density of tetrahydrofuran at elevated pressures. Open image in new window This work, Open image in new window [58], Open image in new window [59], Open image in new window [60], Open image in new window [61], Open image in new window [62], Open image in new window [63], Open image in new window [64]

The data from the other three sources [62, 63, 64] was significantly lower than our values and those from other literature sources. Although these researchers mostly measured at much higher pressures than the other sources, values at atmospheric pressure show that these three data sets have significant errors. For instance, at 323.15 K and atmospheric pressure the value from Schornack and Eckert [62] is more than 35 standard deviations below the mean of the other literature values (ours was within a standard deviation). There may have been some problem with their experimental setup because their value for chlorobenzene at 323 K and atmospheric pressure is 10 kg·m−3 lower than the value from the DIPPR correlation [45], so there seems to be a consistent negative deviation. Zhang and Kiran [63] did not measure at atmospheric pressure, but extrapolating from their data down to atmospheric pressure using a linear pressure dependency shows a similar large negative deviation from most other literature sources. The uncertainty caused by the extrapolation is in this case a magnitude lower than the deviation. For instance, at 302.4 K we got a value of 848.2 kg·m−3 when extrapolating their data, which is about 28 kg·m−3 lower than the literature mean.

For the vapor pressure measurements gamma-valerolactone could be used as a reference compound for validating our gas saturation method. We found the literature data from 11 other sources, and we compared these different data sets in Fig. 3 [56, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74]. Most of the data fall within a few percentage points of each other, but there is one point from Havasi et al. [69] that is about 40 % lower than the other data. It is so far out of line that it is below the y-axis limits in Fig. 3. In general, the data from Havasi et al. show an increasing negative deviation at lower temperatures, which could indicate a problem with the measurement procedure at those temperatures. The 3 points at the lowest temperatures from Havasi et al. were left out when fitting the PC-SAFT parameters.

Our data falls in line with the literature data, although it has a somewhat larger scatter than some of the literature data sets. In more recent experiments with the gas saturation equipment, we were able to improve the repeatability by making repeat measurements of the cell mass and taking the average of them, [75] so it seems that uncertainty in the sample weight was the largest contribution to the uncertainty for the gas saturation measurements presented here. We did not observe any systematic bias in our data when compared to the model or other data.

3.3 Results and PC-SAFT Modeling

The data accompanying this article has been uploaded to a scientific repository (Open Science Framework), and it can be accessed at https://osf.io/u9amn/. The repository contains the density, vapor pressure, and refractive index data. Here, we give an overview of the results.

Table 22 gives the density at 293 K for each of the 10 compounds measured in this study. Literature values are also given for comparison, where available. In general, our measured results match well with literature values. However, with 2-methoxy-4-methylphenol and 2-sec-butylphenol there are relatively large discrepancies between the experimental and literature values [75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101]. For both of these compounds only one literature value could be found, and they were from articles in 1952 and 1896 that used methods with higher uncertainties. The value for 2-pentanone may also seem to be out of line at first glance; however, when looking at the individual literature values one can see large variations between the different sources [82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100]. There are 5 sources that give a density close to ours (about 806.3 kg·m−3), but 6 of the 19 sources give a higher density of about 809 kg·m−3. So many of the values actually lie more than 1 kg·m−3 away from the mean. It is unclear why there is such a large scatter in the data for 2-pentanone, although all of the highest values were measured more than 50 years ago, and the more recent articles report a lower density.

Using the PC-SAFT equation, we could calculate the normal boiling point (at 101,325 Pa) and enthalpy of vaporization of each compound. These values are given in Table 23. For dihydrolevoglucosenone and levoglucosenone the PC-SAFT equation had to be extrapolated about 100 K above the available vapor pressure data to reach the boiling point, so the boiling points for these compounds contain larger uncertainty. For dihydrolevoglucosenone Sherwood et al. [3] measured an approximate value of 476 K for the boiling point using a TGA, which is about 20 K lower than the value we calculated. We observed that dihydrolevoglucosenone decomposed even at 423 K (see Sect. 2.2), and so it is possible that decomposition occurred in the TGA measurement, leading to an estimated value lower than the actual boiling point.
Table 23

Normal boiling points and enthalpies of vaporization of the bio-compounds

Compound

Normal boiling point1 (K)

Enthalpy of vaporization2 at 298.15 K(kJ·mol−1)

This work

Literaturea

This work

Literature

2-Methoxy-4-methylphenol

493.9

494.2

64.58

70.9a

2-Methylfuran

337.4

337 ± 1

32.11

32.4b

2-Pentanone

375.3

375. ± 1

38.26

38.4a

2-sec-Butylphenol

503.5

500. ± 4

78.38

NA

2,6-Dimethoxyphenol

535.0

536 ± 5

76.69

NA

Cyclopentyl methyl ether

378.6

377.9c

37.41

NA

Dihydrolevoglucosenone

499

476d

57.65

NA

Furfural

434.1

434.7 ± 0.4

50.57

50.7 ± 0.2

Levoglucosenone

504

NA

61.56

NA

Tetrahydrofuran

339.2

339. ± 1

31.87

32.16a

γ-Valerolactone

478.3

480.7

53.83

53.9 ± 0.2e

All values were calculated using the PC-SAFT equation of state

NA value is not available at 298.15 K

aRef. [29]

bData from Ref. [29] correlated to obtain value at 298.15 K

cRef. [19] at pressure 99,800 Pa

dRef. [3]

eRef. [70]

1At a pressure of 101,325 Pa, standard uncertainty u(normal boiling point this work) = 1.5 K

2u(enthalpy of vaporization) = 0.7 kJ·mol−1

We can also briefly examine the relationships between molecular structure and properties. For instance we can see that hydrogenating levoglucosenone to dihydrolevoglucosenone gives a compound with a somewhat lower vapor pressure and density. This may be useful information in designing processes that produce dihydrolevoglucosenone from levoglucosenone. γ-valerolactone also stands out because it has a much higher boiling point than other compounds with similar molar masses.

4 Conclusions

Vapor pressures, densities, and refractive indexes were measured for a group of bio-compounds. For several of the compounds this is the first publicly available data on these properties. The experimental data measured here showed good agreement with most literature data for tetrahydrofuran and γ-valerolactone. Comparison also showed that density data at higher pressures from several of the literature sources was erroneous, both for tetrahydrofuran and for 2-pentanone. The new density data in this article helps to fill the gaps left when removing those unreliable datasets.

Notes

Acknowledgements

Open access funding provided by Aalto University. We would like to thank the company Circa for providing the dihydrolevoglucosenone and levoglucosenone samples.

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Authors and Affiliations

  1. 1.Department of Chemical and Metallurgical EngineeringAalto UniversityEspooFinland

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