Experimental Phase Equilibrium Data for Rotenone in Supercritical

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

Experimental Phase Equilibrium Data for Rotenone in Supercritical Carbon Dioxide Published as part of the Journal of Chemical & Engineering Data Latin America special issue. Jeś sica Carvalho Lima,† Paulo Cardozo Carvalho de Araújo,† Gilson dos Santos Croscato,† Ossalin de Almeida,‡ Vladimir Ferreira Cabral,† Leandro Ferreira-Pinto,§ and Lucio Cardozo-Filho*,†,∥ †

Department of Chemical Engineering, State University of Maringá, Maringá, Paraná 87020-900, Brazil Institute of Exact and Natural Sciences, Federal University of Pará, Belém, Pará 66075-110, Brazil § Department of Energy Engineering, Sao Paulo State University (UNESP), Rosana, São Paulo 17602-496, Brazil ∥ Centro Universitario da Fundaçao de Ensino Octavio Bastos (UNIFEOB) Research Center, São João da Boa Vista, São Paulo 13870-421, Brazil

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‡

ABSTRACT: In this paper, we report data for the phase transition of the binary [rotenone (1) + CO2 (2)] system obtained visually using the static synthetic indirect method and a variable-volume cell at temperatures between 303 and 343 K and pressures near 20 MPa. The molar fraction varied from 1.0 × 10−5 to 2.75 × 10−5. For a molar fraction of rotenone greater than 2.75 × 10−5, the phase transition data could not be measured at pressures of 30 MPa because of the experimental limitations of the equipment. The pressure limitation arose because of the difficulty in solubilizing the system where the solubilization occurs close to or above the limits of the experimental apparatus (30 MPa). The transition of the system was identified as the solid−fluid type, and the phase transition profiles are similar. The Peng−Robinson equation of state (PR-EoS) with the classical mixing rule was used to correlate the experimental data to theory, and excellent agreement was found between the experimental and calculated values.

1. INTRODUCTION Rotenone (C23H22O6, CASRN 83-79-4)1 is an odorless organic molecule that has insecticidal, piscicidal, and pesticidal properties. Rotenone can be extracted from tropical plants such as Derris elliptica, D. amazonica, Amorpha f ruticosa, and Tephrosia vogelii.2−4 In Brazil, species of the genus Derris, vine plants that reach the crowns of trees, are popularly known as timbó.5,4,6 In Amazonia, fishermen use timbó to catch fish from rivers. The timbó stuns the fish, and their breathing is paralyzed, resulting in their capture when they rise to the surface of the water in search of oxygen.5−7,6 Rotenone is also used in powdered form to treat scabies and head lice in humans, as well as parasitic mites on chickens, livestock, and pet animals.2,4,6 It is also used to reduce or eradicate invader fish populations. This is possible because the bioactive agent inhibits cellular respiration in most living organisms.8,7 However, mammals are usually not affected because of its inefficient absorption into the body. Despite this, the use of large quantities of rotenone can cause health problems.6 Rotenone is unstable in the presence of light and undergoes degradation and decomposes rapidly in the soil and water. Therefore, its pesticidal action can be lost after a few days.2 Thus, it is important to develop techniques that increase the © XXXX American Chemical Society

extraction yield and optimize the effect and application of this bioactive compound.9,10 One technique that can be explored and that presents satisfactory results is the supercritical fluid technique, which can be used for the extraction11−15 and study of the controlled release of bioactive agents from particles.9,10 According to Othman et al.,16 a method that enables the extraction of the title compound without requiring further purification is very important for the marketing of this natural pesticide. In particular, tuning the temperature and pressure may change the selectivity for the extraction of the active compounds. Baldino et al.17 carried out extraction on the vegetable matrix D. elliptica with supercritical CO2, obtaining a final product with 93 wt % of rotenone and rotenoids. Sae-Yun et al.18 carried out the extraction of rotenone from D. elliptica using pressurized liquids and obtained yields of 46.1%. The controlled release of rotenone from a coprecipitate with a biodegradable polymer is one possible way to prolong its insecticidal activity, meaning a reduction in the number of applications for a given culture.2 Martin et al.19 studied a coprecipitate of rotenone prepared for use as a biopesticide Received: December 5, 2018 Accepted: May 10, 2019

A

DOI: 10.1021/acs.jced.8b01165 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data

Article

Table 1. Properties of the Substances Used in the Worka compound

MW (g· mol−1)

suppliers

purity (wt %)

CASRN

Tc (K)

Pc (MPa)

Tb (K)

ω

rotenone CO2

394.4228 44.0128

Synth White Martins

>95 99.9 (in the liquid phase)

83-79-4 124-38-9

1270.9129 304.2128

1.6729 7.3828

488.229

0.7730 0.22328

Notation: MW = molecular weight; Tc = critical temperature; Pc = critical pressure; Tb = boiling temperature; ω = acentric factor.

a

curvature of first derivative curve changes exactly at its inflection point, and that point was considered the melting temperature for that sample (see Figure 1). Table 2 presents

using carbon dioxide. Rotenone encapsulation can protect the pesticide from degradation, thus reducing the quantity required for use. Other authors20−22 have reported promising results using particle engineering techniques (such as supercritical antisolvent (SAS) and rapid expansion of supercritical solutions (RESS)), in which micro/nano drug particles encapsulated in polymers/biopolymers have been produced, and the release of these active ingredients has been studied. The results are optimistic and show potential for use with bioactive compounds such as rotenone because controlled release can increase its period of action as an insecticide and reduce the number of required applications of the biomolecule. Knowledge of the phase behavior of the supercritical system [rotenone (1) + CO2 (2)] is crucial before the development or optimization of processes in supercritical fluids, supercritical extraction, reaction in supercritical fluids, or particle engineering in supercritical fluids can be carried out.9,10,23−25 Thus, this work focuses on the study of the thermodynamic interactions between CO2 and rotenone. The methods used for measuring the solubility of solids in supercritical fluids can be classified as dynamic, static, chromatographic, and spectroscopic.26 The static method is divided into analytical, synthetic, and gravimetric types.26,27 Thus, the objective of this study was to obtain phase equilibrium data for the binary [rotenone (1) + CO2 (2)] system experimentally at high pressures and temperatures ranging from 303 to 343 K using the synthetic method. The molar fractions studied ranged from 1.0 × 10−5 to 2.75 × 10−5, and the solid−fluid (SF) phase equilibrium data were obtained. These data are essential for the implementation and optimization of extraction technology and particle engineering of rotenone in supercritical carbon dioxide.

Figure 1. Differential scanning calorimetry (DSC) curves of rotenone (3.13 wt % of water).

Table 2. DSC Results for Rotenonea rotenone

Purity (wt %)

experimental temperature onset (K)

this work Donnelly et al.50

>95 98.38

431.97 437.86

experimental temperature peak maximum (K) 435.89

a

Literature melting point: Worthing and Walker31 [T = 436 K], Ling32 [T = 438 K], Kidd and James33 [T = 436 K].

2. EXPERIMENTAL SECTION 2.1. Materials. Carbon dioxide (99.9 wt %, liquid phase) was purchased from White Martins S.A (Brazil). A rotenone standard (95 wt %) was purchased from Synth (Brazil). For CO2, the critical properties and acentric factor of the pure compound were obtained from the DIPPR28 database. For rotenone, this information was estimated using the Joback group contribution method29 and the Pitzer equation.30 The pure component properties of these substances are presented −1 in Table 1. The melting heat (Δhmelting = Δhfus i i = 72.15 J·g ) fus and melting temperature (Tm = ΔTi = 435.89 K) for rotenone was measured using differential scanning calorimetry (DSC-60 Plus Series, Shimadzu). Approximately 2 mg of sample was placed on an aluminum pan and the system used an operating temperature range from 303 to 673 K and used nitrogen (99.999% purity) as the coolant fluid. The coolant fluid flow rate was 50 mL·min−1. The heating rate was 283 K· min−1. For the DSC curve, the value of the melting temperature was determined by the inflection point of the first derivative of the melting peak. During the DSC analysis, when a melting process occurs, the sample absorbs energy and then, the curve shows a characteristic melting peak (endothermic process). The

comparative data between the literature31−33 and this work. It is found that the melting temperatures obtained experimentally in this study are similar to those reported in the literature. We carried out Karl Fischer titration of the rotenone sample and found its water content to be 3.13%. 2.2. Apparatus and Experimental Procedure. The experiments were conducted using the visual static synthetic method at high pressure in a variable-volume cell in the experimental apparatus (see Figure 2).24,27,34−40 The principle of this method is based on the preparation of a solution with a known overall composition. Crucially, there is no need for sample taking.41 The measurement apparatus comprises a phase equilibrium cell, a temperature proportional−integral−derivative (PID) controller (Novus N1100), a temperature indicator (Novus n480i), a pressure indicator (Novus, n1500), thermostatic bath (Julabo, F25-HE, uncertainty of 0.01 K), an absolute pressure transducer (Smar, LD301, uncertainty, u(p), of 0.01 MPa), and a high-pressure syringe pump (ISCO, 260D). The equilibrium cell (diameter of 0.018 m and volume of 25 cm3) has an internal piston. The piston divides the cell into B



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Figure 2. Schematic of the experimental apparatus using the visual synthetic method: 1, CO2 of cylinder; 2, thermostatic bath; 3, syringe pump; 4, valves; 5, pressure transducer; 6, pressure indicator; 7, controller and indicator of temperature; 8, lamp; 9, cell coupled to an aluminum jacket; 10, magnetic stirrer.

Figure 4. Pressure−composition diagram for the system {rotenone (1) + CO2 (2)} at T = 303 K (▲,SF); 313 K (■,SF); 323 K (●,SF); 333 K (★,SF) and 343 K (∗,SF). Experimental data (points) and calculated values using the thermodynamic model at different fitting parameters (lines), PR-vW2.

The heating control of the equilibrium cell was realized with an aluminum jacket coupled to two electrical resistors, a controller, and a thermocouple (PT-100, uncertainty of 0.5 K). Another thermocouple (PT-100, uncertainty of 0.5 K) was attached to a temperature indicator and fixed for direct contact with the mixture. The experimental procedure was started by the insertion of a known amount of the rotenone. The mass of rotenone was weighed on a precision balance (Marte-AM220, uncertainty, u(x), of 0.0001 g). Then, a previously calculated amount of CO2 was inserted via the syringe pump (Isco, 260D, uncertainty of 0.005 g). The CO2 was added to the equilibrium cell under preset conditions of pressure and temperature (p = 10 MPa and T = 293.15 K). The density of added CO2 was determined following Angus et al.42 The mixture was continuously stirred by a magnetic bar inside the cell. After the addition of the mixture, the cell was closed and the system was heated and pressurized. Initially, the heating control was activated to achieve the desired temperature. Subsequently, the mixture was pressurized until a homogeneous phase appeared. Afterward, the pressure was gradually reduced (rate of 0.05 to 0.2 MPa·

Figure 3. (A) Pressure−composition diagram for the system [rotenone (1) + CO2 (2)] at T = 303 K (▲,SF); 313 K (■,SF); 323 K (●,SF); 333 K (★,SF); and 343 K (∗,SF). (B) Pressure− temperature diagram for the system [rotenone (1) + CO2 (2)] at x1 = 1.01 × 10−5 (▲,SF); 1.49 × 10−5 (■,SF); 2.00 × 10−5 (●,SF); 2.50 × 10−5 (★,SF); and 2.50 × 10−5 (∗,SF).

front and rear compartments. In the front chamber, the mixture is added, and in the rear part, the system is pressurized by the injection of CO2 from the high-pressure syringe pump. The observation of the phase transitions was achieved via two sapphire windows. These windows are located on the front and side of the cell. The side window allows the passage of light (light-emitting diode (LED) lamp) for the successful visualization of the phenomena occurring in the front of the cell. C



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min−1) until a two-phase system appeared. This procedure was performed in triplicate for each temperature and overall composition studied. The estimated uncertainty of the temperature and pressure values were less than 0.5 K and 0.01 MPa, respectively. The estimated average uncertainty in the mole fraction values for rotenone were on the order of 10−4%. These uncertainty levels were estimated by propagation of error analysis using the procedure of Rodriguez-Reartes et al.43 In their work, the authors carried out experiments using an experimental apparatus similar to that used by us.

applied in our previous works.38,46,47 This procedure uses the “Solver” tool available in Microsoft Excel (2016 version) for Windows and the XSEOS48 Excel add-in to fit the parameters. The fugacity coefficient of rotenone at infinite dilution (φ̂ ∞ 2 ) was calculated using the XSEOS Excel add-in. The Solver addin fits the values of a cell or a group of cells that are directly or indirectly related to the objective function.49 For the parameter fitting procedure, the generalized reduced gradient (GRG) method was used, which uses two techniques to search the optimized value: the quasi-Newton technique and the conjugate gradient method. The algorithm automatically chooses between them according to the problem. During the minimization process, the parameters A and B, the binary interaction parameters (kij and lij), and the molar volume of the solid (Vs2) are considered the decision variables. The parameter values fitted in this work for all temperatures were the following: kij = 0.3312, lij = 0.1785, Vs2 = 601.7 cm3·mol−1, A = 2.0 × 10−12 and B = 5249 K.

3. THERMODYNAMIC MODELING The thermodynamic modeling of the SF phase equilibrium data was performed using the following equation:44 ÄÅ s ÉÑ P2sat ÅÅÅ V2P ÑÑÑ ÑÑ y2 = ÅÅ ∞ expÅ Pφ2̂ ÅÇ RT ÑÑÖ (1) where Psat 2 is the solid vapor pressure of the solute (rotenone), P is the pressure, φ̂ ∞ 2 is the fugacity coefficient of rotenone at infinite dilution, Vs2 is the molar volume of pure rotenone, R is the universal gas constant, and T is the temperature. The fugacity coefficient of rotenone at infinite dilution (φ̂ ∞ 2 ) was calculated using the Peng−Robinson equation of state (PR-EoS)45 with the classical van der Waals mixing rule (vdW2), n

a=

n

∑ ∑ xixjaij n

Table 3. Experimental solubility. Phase Equilibrium Data for Temperature (T), Pressure (p) with Combined Standard Uncertainty uc(p), and Molar Fraction x for the System [Rotenone (1) + CO2 (2)]. The Rotenone Used in This Work has 3.13 wt % Water

(2)

i=1 i=1

b=

4. RESULTS AND DISCUSSION The experimental data for the SF phase transition obtained for the binary [rotenone (1) + CO2 (2)] system are shown in Table 3. The experimental pressure, temperature, and mole fraction of rotenone were 8 to 20 MPa, 303 to 343 K, and 1.0 × 10−5 to 2.75 × 10−5, respectively. The results in Table 3 are shown in terms of the molar fraction of rotenone (x1) and the pressure transition values (p). The experimental uncertainty,

n

∑ ∑ xixjbij

(3)

i=1 i=1

where

T/Ka 1/2

aij = (aiaj) bij =

Psat 2

(1 − kij)

303 303 303 303 303 313 313 313 313 313 323 323 323 323 323 333 333 333 333 333 343 343 343 343 343

(4)

1 (bi + bj)(1 − lij) 2

(5)

was calculated using the following equation:

ln P2sat = A −

B T

(6)

where A and B are constants that were fitted using the experimental rotenone solubility. In addition to these parameters, the binary interaction parameters (kij and lij) and the molar volume of the solid (Vs2) were also fitted using the experimental data for rotenone solubility. The parameter fitting procedure used here minimizes the objective function defined as the sum of squared deviations of the predicted and calculated solubilities. The expression of this function is given by ij y exp − y calc yz jj 2ij 2ij z zz F = ∑ ∑ jjj zz exp jj zz y2 z j=1 i=1 j ij k { n

mj

2

(7)

where “n” is the number of experimental sets (isothermal data), mj is the number of points for each experimental set j, calc and yexp 2ij and y2ij are the rotenone solubility data obtained experimentally and calculated using the PR-EoS, respectively. The parameter fitting procedure used here is the same as that

x1b 1.01 1.49 2.00 2.50 2.75 1.01 1.49 2.00 2.50 2.75 1.01 1.49 2.00 2.50 2.75 1.01 1.49 2.00 2.50 2.75 1.01 1.49 2.00 2.50 2.75

× × × × × × × × × × × × × × × × × × × × × × × × ×

10−5 10−5 10−5 10−5 10−5 10−5 10−5 10−5 10−5 10−5 10−5 10−5 10−5 10−5 10−5 10−5 10−5 10−5 10−5 10−5 10−5 10−5 10−5 10−5 10−5

p/MPa

uc(p)/MPac

transition typed

8.53 10.54 12.16 13.93 14.60 10.05 11.75 13.61 14.55 15.53 11.95 13.43 15.18 16.24 16.91 13.85 14.98 16.39 17.27 17.92 15.34 16.39 17.45 18.26 18.91

0.029 0.092 0.153 0.124 0.010 0.016 0.103 0.022 0.100 0.022 0.148 0.171 0.095 0.080 0.047 0.039 0.021 0.027 0.059 0.016 0.026 0.020 0.064 0.140 0.040

SF SF SF SF SF SF SF SF SF SF SF SF SF SF SF SF SF SF SF SF SF SF SF SF SF

u(T) = 0.5 K. bu(x) in order 10−4%. cuc(p) = sqrt(u2(repeatability) + u2(pump)). dSolid−fluid (SF) transition data.

a

D



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Reference Database Number 69; Linstrom, P.J., Mallard, W. J., Eds.; NIST: Gaithersburg, MD. (2) Martin, L.; Liparoti, S.; Della Porta, G.; Adami, R.; Marqués, J. L.; Urieta, J. S.; Mainar, a. M.; Reverchon, E. Rotenone Coprecipitation with Biodegradable Polymers by Supercritical Assisted Atomization. J. Supercrit. Fluids 2013, 81, 48−54. (3) Leslie Crombie, D. A. W. Biosynthesis in the Rotenoid Group of Natural Products: Applications of Isotope Methodology. Phytochemistry 1998, 49 (6), 1479−1507. (4) Luitgards-Moura, J. F.; Castellón Bermudez, E. G.; Rocha, A. F. I.; Tsouris, P.; Rosa-Freitas, M. G. Preliminary Assays Indicate That Antonia Ovata (Loganiaceae) and Derris Amazonica (Papilionaceae), Ichthyotoxic Plants Used for Fishing in Roraima, Brazil, Have an Insecticide Effect on Lutzomyia Longipalpis (Diptera: Psychodidae: Phlebotominae). Mem. Inst. Oswaldo Cruz 2002, 97 (5), 737−742. (5) Andrade, J. N.; Costa Neto, E. M.; Brandão, H. Using Ichthyotoxic Plants as Bioinsecticide: A Literature Review. Rev. Bras. Plantas Med. 2015, 17 (4), 649−656. (6) da Costa, D.; Silva, C.; Pinheiro, A.; Frommenwiler, D.; Arruda, M.; Guilhon, G.; Alves, C.; Arruda, A.; da Silva, M. Using LC and Hierarchical Cluster Analysis as Tools to Distinguish Timbó Collections into Two Deguelia Species: A Contribution to Chemotaxonomy. Molecules 2016, 21 (5), 569. (7) Teixeira, S. P.; Rocha, J. F. Oil Glands in the Neotropical Genus Dahlstedtia Malme (Leguminosae, Papilionoideae, Millettieae). Rev. Bras. Bot. 2009, 32 (1), 57−64. (8) Tozzi, A. M. G. A. A Identidade Do Timbó-Verdadeiro: Deguelia Utilis (A.C.Sm.) A.M.G.Azevedo (Leguminosae – Papilionoideae). Rev. Bras. Biol. 1998, 58 (3), 511−516. (9) Giufrida, W. M.; Cabral, V. F.; Cardoso-Filho, L.; dos Santos Conti, D.; de Campos, V. E. B.; da Rocha, S. R. P. Medroxyprogesterone-Encapsulated Poly(3-Hydroxybutirate-Co-3Hydroxyvalerate) Nanoparticles Using Supercritical Fluid Extraction of Emulsions. J. Supercrit. Fluids 2016, 118, 79−88. (10) Giufrida, W. M.; Voll, F. A.; Feihrmann, A. C.; Kunita, M. H.; Madureira, E. H.; Guilherme, M. R.; Vedoy, D. R. L.; Cabral, V. F.; Cardozo-Filho, L. Production of Microparticles of PHBV Polymer Impregnated with Progesterone by Supercritical Fluid Technology. Can. J. Chem. Eng. 2016, 94 (7), 1336−1341. (11) Lemos, C. O. T.; Garcia, V. A. D. S.; Gonçalves, R. M.; Leal, I. C. R.; Siqueira, V. L. D.; Filho, L. C.; Cabral, V. F. Supercritical Extraction of Neolignans from Piper Regnelli Var. Pallescens. J. Supercrit. Fluids 2012, 71, 64−70. (12) Gonçalves, R. M.; Lemos, C. O. T.; Leal, I. C. R.; Nakamura, C. V.; Cortez, D. A. G.; da Silva, E. A.; Cabral, V. F.; Cardozo-Filho, L. Comparing Conventional and Supercritical Extraction of (−)-Mammea A/BB and the Antioxidant Activity of Calophyllum Brasiliense Extracts. Molecules 2013, 18 (6), 6215−6229. (13) Carrara, V. D. S.; Serra, L. Z.; Cardozo-Filho, L.; Cunha, E. F.; Torres-Santos, E. C.; Cortez, D. A. G. HPLC Analysis of Supercritical Carbon Dioxide and Compressed Propane Extracts from Piper Amalago L. with Antileishmanial Activity. Molecules 2012, 17 (1), 15− 33. (14) Garcia, V. A. D. S.; Cabral, V. F.; Zanoelo, É . F.; da Silva, C.; Filho, L. C. Extraction of Mucuna Seed Oil Using Supercritical Carbon Dioxide to Increase the Concentration of L-Dopa in the Defatted Meal. J. Supercrit. Fluids 2012, 69, 75−81. (15) Botelho, J. R. S.; Medeiros, N. G.; Rodrigues, A. M. C.; Araújo, M. E.; Machado, N. T.; Guimarães Santos, A.; Santos, I. R.; GomesLeal, W.; Carvalho, R. N. Black Sesame (Sesamum Indicum L.) Seeds Extracts by CO2 Supercritical Fluid Extraction: Isotherms of Global Yield, Kinetics Data, Total Fatty Acids, Phytosterols and Neuroprotective Effects. J. Supercrit. Fluids 2014, 93, 49−55. (16) Othman, Z. S.; Hassan, N. H.; Yusop, M. R.; Zubairi, S. I. Development of a New Binary Solvent System Using Ionic Liquids as Additives to Improve Rotenone Extraction Yield from Malaysia Derris Sp. J. Chem. 2015, 2015, 1−7.

u(p), was calculated from the measured pressures for each transition considering the standard deviations of each triplicate. No change in the physical state was observed in the experiments. That is, all experiments remained in the solid state at all studied temperatures. Upon observing the behavior of the system (see Figure 3), we verified that the phase behavior profiles are similar and the transition pressures are close. For molar fractions of rotenone greater than 2.75 × 10−5, it was not possible to measure the phase transition because of the operational limit of the apparatus, 30 MPa. It is necessary to raise the pressure of the system to obtain a single (homogeneous) phase and then decrease it to obtain the phase transition. An increase in the pressure as a function of temperature for each fraction of the explored system occurs because of the higher repulsive forces at higher temperatures. Figure 4 compares the experimental and calculated values of the rotenone solubility. The thermodynamic modeling used in this work represents the experimental results very well. The correlation of all experimental data has a percentage mean error of 6.5%. Therefore, the Peng−Robinson equation of state using the classical van der Waals mixing rule represents the experimental data satisfactorily.

5. CONCLUSION In this work, we determined the phase equilibrium data for the binary [rotenone (1) + CO2 (2)] system and obtained SF transitions between 303−343 K using the visual static synthetic method. The obtained maximum pressure was close to 20 MPa. From the variation in the molar fraction and temperature, it was possible to obtain a phase diagram to determine the solubility of the system. The experimental data were modeled with the PR-EoS using the classical quadratic mixing rule, and this provided a good representation of the experimental information. From the data obtained in this work, it will be possible to perform supercritical extraction studies on the carbon dioxide extraction of rotenone contained in vegetable matrices, as well in the nanoparticle formation process (particle engineering) using techniques such as SAS or RESS. The obtained data also give an idea of the best range of operating conditions (pressure and temperature) for various processes.

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AUTHOR INFORMATION

Corresponding Author

*E-mail: lcfi[email protected]. ORCID

Lucio Cardozo-Filho: 0000-0002-0656-9471 Funding

We thank the following Brazilian agencies for financial support: CAPES (Ministry of Education) and CNPq (National Council for Scientific and Technological Development). L.F.P. thanks the Fundaçaõ de Amparo à Pesquisa do Estado de São Paulo, FAPESP (Brazil), for financial support through Grant 2018/ 23063-1. Notes

The authors declare no competing financial interest.

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REFERENCES

(1) Lemmon, E. W.; McLinden, M. O.; Friend, D. G. Thermophysical Properties of Fluid Systems. NIST Chemistry Web- Book, NIST Standard E



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(17) Baldino, L.; Scognamiglio, M.; Reverchon, E. Extraction of Rotenoids from Derris Elliptica Using Supercritical CO 2. J. Chem. Technol. Biotechnol. 2018, 93 (12), 3656−3660. (18) Sae-Yun, A.; Ovatlarnporn, C.; Itharat, A.; Wiwattanapatapee, R. Extraction of Rotenone from Derris Elliptica and Derris Malaccensis by Pressurized Liquid Extraction Compared with Maceration. J. Chromatogr. A 2006, 1125 (2), 172−176. (19) Martin, L.; Liparoti, S.; Della Porta, G.; Adami, R.; Marqués, J. L.; Urieta, J. S.; Mainar, A. M.; Reverchon, E. Rotenone Coprecipitation with Biodegradable Polymers by Supercritical Assisted Atomization. J. Supercrit. Fluids 2013, 81, 48−54. (20) Alessi, P.; Cortesi, A.; Kikic, I.; Foster, N. R.; Macnaughton, S. J.; Colombo, I. Particle Production of Steroid Drugs Using Supercritical Fluid Processing. Ind. Eng. Chem. Res. 1996, 35 (12), 4718−4726. (21) Nakamura, M.; Ozaki, S.; Abe, M.; Doi, H.; Matsumoto, T.; Ishimura, K. Size-Controlled Synthesis, Surface Functionalization, and Biological Applications of Thiol-Organosilica Particles. Colloids Surf., B 2010, 79 (1), 19−26. (22) Hogan, C. J.; Yun, K. M.; Chen, D.-R.; Lenggoro, I. W.; Biswas, P.; Okuyama, K. Controlled Size Polymer Particle Production via Electrohydrodynamic Atomization. Colloids Surf., A 2007, 311 (1−3), 67−76. (23) Prado, I. M.; Giufrida, W. M.; Alvarez, V. H.; Cabral, V. F.; Quispe-Condori, S.; Saldaña, M. D. a.; Cardozo-Filho, L. Phase Equilibrium Measurements of Sacha Inchi Oil (Plukenetia Volubilis) and CO2 at High Pressures. J. Am. Oil Chem. Soc. 2011, 88 (8), 1263−1269. (24) Pinto, L. F.; Rodriguez-Reartes, S. B.; Corazza, M. L.; Cabral, V. F.; de Araújo, P. H. H.; Madureira, E. H.; Zabaloy, M. S.; CardozoFilho, L. Phase Behavior of Carbon Dioxide+medroxyprogesterone Acetate System at High Pressures. Fluid Phase Equilib. 2013, 349, 1− 11. (25) Giufrida, W. M.; Pinto, L. F.; Zanette, A. F.; Voll, F. A. P.; Kunita, M. H.; Cabral, V. F.; Cardozo-Filho, L. Liquid−Vapor Equilibrium Data of CO2+dichloromethane+medroxyprogesterone System. Fluid Phase Equilib. 2014, 362, 307−312. (26) Dohrn, R.; Brunner, G. High-Pressure Fluid-Phase Equilibria: Experimental Methods and Systems Investigated (1988−1993). Fluid Phase Equilib. 1995, 106 (1−2), 213−282. (27) Favareto, R.; Pereira, J. R. D.; Santana, C. C.; Madureira, E. H.; Cabral, V. F.; Tavares, F. W.; Cardozo-Filho, L. High-Pressure Phase Diagram of the Drug Mitotane in Compressed and/or Supercritical CO2. J. Chem. Thermodyn. 2010, 42 (2), 286−290. (28) Wilding, W. V.; Rowley, R. L.; Oscarson, J. L. DIPPR® Project 801 Evaluated Process Design Data. Fluid Phase Equilib. 1998, 150− 151, 413−420. (29) Joback, K. G.; Reid, R. C. Estimation Of Pure-Component Properties From Group-Contributions. Chem. Eng. Commun. 1987, 57 (1−6), 233−243. (30) Pitzer, K. S. Thermodynamics, 3rd ed.; McGraw-Hill: New York, 1995. (31) Worthing, C. R., Walker, S. B. Eds. Pesticide Manual, 7th ed.; Lavenham Press: Suffolk, England, 1983. (32) Ling, N.. RotenoneA Review of Its Toxicity for Fisheries Management; New Zealand Department of Conservation: Wellington, New Zealand, 2003. (33) Kidd, H.; James, D. R. The Agrochemicals Handbook, 3rd ed.; Royal Society of Chemistry Information Services: Cambridge, United Kingdom, 1991. (34) Giufrida, W. M.; Pinto, L. F.; Zanette, A. F.; Voll, F. A. P.; Kunita, M. H.; Cabral, V. F.; Cardozo-Filho, L. Liquid−Vapor Equilibrium Data of CO2+dichloromethane+medroxyprogesterone System. Fluid Phase Equilib. 2014, 362, 307−312. (35) Giufrida, W. M.; Rodriguez-Reartes, S. B.; Alonso, C. G.; Zabaloy, M. S.; Cabral, V. F.; Tavares, F. W.; Cardozo-Filho, L. HighPressure Experimental Data of CO 2 + Mitotane and CO 2 + Ethanol + Mitotane Mixtures. J. Chem. Eng. Data 2011, 56 (12), 4333−4341.

(36) Souza, A. T.; Benazzi, T. L.; Grings, M. B.; Cabral, V.; Silva, E. A.; Cardozo-Filho, L.; Ceva Antunes, O. A. Supercritical Extraction Process and Phase Equilibrium of Candeia (Eremanthus Erythropappus) Oil Using Supercritical Carbon Dioxide. J. Supercrit. Fluids 2008, 47 (2), 182−187. (37) Zanette, A. F.; Ferreira-Pinto, L.; Giufrida, W. M.; Zuber, A.; Feirhmann, A. C.; Castier, M.; Cardozo-Filho, L.; Cabral, V. F. Vapor−Liquid Equilibrium Data for Carbon Dioxide + (R, S)-1,2Isopropylidene Glycerol (Solketal) + Oleic Acid Systems at High Pressure. J. Chem. Eng. Data 2014, 59 (5), 1494−1498. (38) Ferreira, M. O.; Ferreira-Pinto, L.; Souza, E. M. B. D.; Castier, M.; Voll, F. A. P.; Cabral, V. F.; Cardozo-Filho, L. Experimental Vapor−Liquid Equilibria for the Systems {2-Ethyl-1-Hexanol + Glycerol + CO 2 } and {2-Methyl-2-Propanol + Glycerol + CO 2 }. J. Chem. Eng. Data 2013, 58 (9), 2506−2512. (39) Favareto, R.; Fregadolli, P. H.; Cabral, V. F.; Antunes, O. A. C.; Cardozo-Filho, L. Phase Equilibria of Acrylonitrile and p -Bromobenzaldehyde in Carbon Dioxide. J. Chem. Eng. Data 2008, 53 (5), 1080−1084. (40) Favareto, R.; Cabral, V. F.; Corazza, M. L.; Cardozo-Filho, L. Vapor−Liquid and Solid−Fluid Equilibrium for Progesterone+CO2, Progesterone+propane, and Progesterone+n-Butane Systems at Elevated Pressures. J. Supercrit. Fluids 2008, 45 (2), 161−170. (41) Dohrn, R.; Fonseca, J. M. S.; Peper, S. Experimental Methods for Phase Equilibria at High Pressures. Annu. Rev. Chem. Biomol. Eng. 2012, 3 (1), 343−367. (42) Schneider, G. M. Carbon Dioxide - International Thermodynamic Tables of the Fluid State, Bd. 3. Von S. Angus, B. Armstrong Und K. M. de Rerrck. Pergamon Press Ltd., Oxford-New York 1976. 1. Aufl., XXVII, 385 S., Zahlr. Abb. u. Tab., Geb., DM 172,50. Chem. Ing. Tech. 1977, 49 (7), 594−594. (43) Rodriguez-Reartes, S.; Cismondi, M.; Franceschi, E.; Corazza, M. L.; Oliveira, J. V.; Zabaloy, M. S. High-Pressure Phase Equilibria of Systems Carbon Dioxide+n-Eicosane and Propane+n-Eicosane. J. Supercrit. Fluids 2009, 50 (3), 193−202. (44) Smith, J. M.; Van Ness, H. C.; Abbot, M. M. Introduction to Chemical Engeneering Thermodinamics, 7th ed.; McGraw-Hill, Ed.: New York, 2005. (45) Peng, D.-Y.; Robinson, D. B. A New Two-Constant Equation of State. Ind. Eng. Chem. Fundam. 1976, 15 (1), 59−64. (46) Ferreira-Pinto, L.; Feihrmann, A. C.; Tavares, C. R. G.; dos Reis Coimbra, J. S.; Saldaña, M. D. A.; Vedoy, D. R. L.; Cardozo-Filho, L. Leachate Treatment Using Supercritical Water. Can. J. Chem. Eng. 2017, 95 (8), 1442−1448. (47) Ferreira-Pinto, L.; Zanette, A.; Voll, F. A. P.; Cabral, V. F.; Castier, M.; Cardozo-Filho, L. Vapor−Liquid Equilibrium of Carbon Dioxide + Ethyl Acetate + Oleic Acid Mixtures at High Pressures. J. Chem. Eng. Data 2017, 62 (9), 2855−2860. (48) Castier, M. An Open Software for Chemical Engineering Thermodynamics. Chem. Eng. Educ. 2008, 42 (2), 74−81. (49) Barati, R. Application of Excel Solver for Parameter Estimation of the Nonlinear Muskingum Models. KSCE J. Civ. Eng. 2013, 17 (5), 1139−1148. (50) Donnelly, J. R.; Drewes, L. A.; Johnson, R. L.; Munslow, K. K. K.; Knapp, K. K.; Sovocool, G. W. Purity and Heat of Fusion Data for Environmental Standards as Determined by Differential Scanning Calorimetry. Thermochim. Acta 1990, 167 (2), 155−187.

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Experimental Phase Equilibrium Data for Rotenone in Supercritical

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