Research Article
Edgar Teixeira de Souza Junior
Edgar Teixeira de Souza Junior
Laboratory of Unit Operations, Polytechnic School, Pontifical
Catholic University of Rio Grande do Sul, Avenida Ipiranga 6681, CEP 90619-900,
Porto Alegre, Brazil. E-mail:
edgar.souza@acad.pucrs.br
Rafael Nolibos Almeida
Rafael Nolibos Almeida
Laboratory of Unit Operations, Polytechnic School, Pontifical
Catholic University of Rio Grande do Sul, Avenida Ipiranga 6681, CEP 90619-900,
Porto Alegre, Brazil. E-mail: rnolibos@gmail.com
Eduardo Cassel
Eduardo Cassel
Laboratory of Unit Operations, Polytechnic School, Pontifical
Catholic University of Rio Grande do Sul, Avenida Ipiranga 6681, CEP 90619-900,
Porto Alegre, Brazil. E-mail: cassel@pucrs.br
Rubem Mário Figueiró Vargas
Rubem Mário Figueiró Vargas
Laboratory of Unit Operations, Polytechnic School, Pontifical
Catholic University of Rio Grande do Sul, Avenida Ipiranga 6681, CEP 90619-900,
Porto Alegre, Brazil. E-mail: rvargas@pucrs.br
Aline Machado Lucas
Aline Machado Lucas
Corresponding
Author
Laboratory of Unit Operations, Polytechnic School, Pontifical
Catholic University of Rio Grande do Sul, Avenida Ipiranga 6681, CEP 90619-900,
Porto Alegre, Brazil. E-mail: aline.lucas@pucrs.br; Tel.: +55-51-3353-4585
Abstract
This study aims to compare the supercritical extraction (SFE) and steam
distillation (SD) to obtain the Curcuma longa essential oil, evaluating the
yield and composition for different conditions, as well as the mathematical
modeling of the extraction curve. Analysis of the chemical composition of the
essential oil was performed by gas chromatography coupled to mass spectrometry
(GC-MS). The experimental extraction curve was plotted, and a mathematical
model was used to fit the data for the SD and SFE methods. The data indicate
that the best condition for SFE is 90 bar, 40 ° C (0.0219 goil/gplant)
with 10.80% ar-turmerone and 24.12% a-turmerone, for SD the one performed at 3 bar (133
° C) (0.0486 goil/gplant) with 35.42% α-zingiberene and
24.52% a-turmerone. Different major compounds were obtained varying the
extraction technique. The mathematical modeling adequately represented the
extraction processes.
Abstract Keywords
Steam distillation, supercritical
extraction, chromatography, modeling, composition, Curcuma longa.
1.
Introduction
Curcuma longa L is a plant of the Zingiberaceae family, whose rhizome can be used to
obtain its essential oil, which is composed of mainly ar-turmerone, a and b-zingiberene [1-2]. Its essential oil has antifungal
properties, as well as the ability to inhibit mycotoxins from certain fungi,
making it possible to use it as a food preservative [3-5]. Another relevant property is its
antioxidant capacity, which can be applied to reduce the rancidity of foods
[6]. The literature also indicates the promising anticancer capacity of
ar-turmerone compound [7].
To obtain the volatile extract, techniques such as steam distillation are traditionally used, due to their low cost. The advantage of this technique is the immiscibility between the organic compounds and water, facilitating the removal of the product, however, the high temperatures used can generate changes in the oil obtained [8-10]. Another technique for obtaining the volatile extract is the supercritical extraction using CO2, which preserves the properties of thermosensitive compounds, performing their extraction with minimal damage, in addition to the easy removal of the solvent at the end of the extraction. However, it is still a technique with a high implementation cost due to the high pressures used [11-12].
The different extraction techniques available generate products with differences in their chemical composition, making it necessary to determine the different compounds obtained from each type of extraction [13]. For this, it is necessary to use multivariate statistical analysis, such as, for example, the principal components analysis, which allows an analysis that would not be easily achieved with the simple study of the data, due to its ability to reduce variables. Thus, it is possible to verify the variation in the composition, according to the extraction method and the condition used.
Due to the lack of technology associated with the essential oils industry, it is necessary to include scientific data to meet this demand. Therefore, the adjustment of mathematical models that adequately represent the yield versus time extraction curve, as well as obtaining mass transfer parameters, is an important step for the proper scale-up of extraction processes. Among the different types of models used to describe extraction processes, a first-order model can be highlighted, extensively used in adsorption processes [14], diffusion models [15], and models that describe differential balances for each phase [16].
2.
Materials and methods
2.1
Plant preparation
The plant material used in this study is composed of turmeric rhizomes grown in Morrinhos do Sul and purchased in Porto Alegre – Rio Grande do Sul, Brazil (-29.30, -49.92).
The turmeric rhizomes in natura were cut into irregular pieces, without removing the peel. The wet plant was ground using a knife mill and a sample was collected to quantify the moisture, using a thermogravimetric balance at 60 °C. The fresh grounded material was then used to carry out the experiments.
2.2 Extraction with supercritical fluid
For the highest yield
condition, the extract yield versus time curve was constructed in triplicate,
for subsequent mathematical modeling. The extracts were collected with a time
interval of 10 minutes, measuring mass at each time interval, until the plant
was exhausted, that is until there was no mass increase (constant mass was
considered after three consecutive measurements). The yield was obtained by
dividing the extracted mass by the plant mass used in the extraction.
Figure 1. Diagram of the supercritical extraction pilot unit: C–CO2 cylinder, HE–heat exchanger, CV–check valve, P1–CO2 high pressure pump, EV–extraction vessel, T–temperature transmitter, P–pressure transmitter, VS–separation vessel, MFT–mass flow transmitter, SV–stop valve.
2.3 Steam distillation
The extractions via steam distillation (SD) were carried out in a pilot scale equipment, located in the Laboratory of Unit Operations (LOPE) of the Polytechnic School – PUCRS. The system is represented in a schematic diagram, as shown in Fig. 2. The equipment has a boiler (B1) with a capacity of 20 L of solvent (water), the energy source is an electrical resistance of 2 kW, it has level sensors (upper and lower) and pressure and temperature measurement. The extraction vessel (EV1) has a capacity of 10 L of useful volume, as well as temperature and pressure sensors, is 31.3 cm high and 19.3 cm in diameter. The system also has a multitubular shell-tube condenser cooled with water close to 1°C, using a thermostatic bath [24].
The steam
distillation process was carried out with 1000 g of the prepared plant. The
extractions were carried out at three different absolute pressures (1, 2, and 3
bar), with the aim of analyzing the effect on the yield and composition of the
essential oil. The procedure was performed in triplicate, and for the highest
yield condition, the experimental yield curve versus the extraction time was
constructed, measuring the oil volume for each 5 minutes’ interval.
Figure 2. Steam distillation pilot plant schematic: B – boiler, EV – extraction vessel, C – condenser, S – separator, T – temperature transmitter, P – pressure transmitter, MF – flow meter, N – flow measurement level.
The specific mass of the essential oil was determined by measuring the mass of 1 mL of the oil, using an analytical balance (Mars AW220 e = ± 0.0001g). This procedure was performed in triplicate. Plant density and porosity were determined using a pycnometer (Quantachrome MVP-6DL).
2.4 Chromatographic Analysis via GC-MS
Turmeric extracts were dehydrated with anhydrous sodium sulfate (Na2SO4 - Synth) and diluted in cyclohexane (1: 2) (Merck). Chemical composition was determined using a gas chromatograph equipped with a mass spectrometer (Hewlett Packard and Agilent model 7890A CG-EM and mass detector 5975C). The carrier gas was helium (0.8 mL.min-1), the injector temperature was 250 °C, and the injected volume was 0.2 mL, using split mode with a division rate of 1:55. The capillary column was HP-5MS (Hewlett Packard and Agilent, 5% phenyl methyl siloxane, 30 m 250 mm 0.25 mm). The temperature setting was 60 °C (8 min), 60 °C-180 °C, 3 °C.min-1, 180 °C (1 min), 180 °C-250 °C, 20 °C.min-1, 250 °C (10 min).
Components were identified
by comparing their Retention Index (RI) on the column, determined in relation
to a homologous series of n-alkanes (C8-C20), with those of pure standards or
reported in the literature. A comparison of the mass spectra of the compounds
with the spectra stored in the GC-MS database [25] was
also performed.
2.5 Principal Component Analysis (PCA)
The comparative statistical analysis of the composition of the products obtained was carried out through the analysis of principal components which was realized using the compounds percentages obtained through gas chromatography, for each of the techniques and conditions. The PCA was executed in the Minitab® software, where the data were implemented in the form of a table, where the lines were the percentage of the components and the columns were the pressure conditions under which the extractions were performed, the calculation was performed from the covariance of data.
2.6 Mathematical Modeling
The model used in this work
was based on the model developed by Reverchon [16].
The model consists of a one-dimensional mass balance for the extract,
assuming a linear behavior for the solid-fluid phase equilibrium. Two
independent variables, time (t) and fixed bed height (z) were considered only,
and the radial dispersion along the column is considered insignificant, for
these assumptions the model was developed. The mass balance is given below in
Equations 1 and 2.
Fluid phase mass balance:
|
|
Mass balance in the solid phase:
|
|
3.
Results and discussion
The average yield obtained from the
experimental data acquired through the extractions is shown in Table 1 in
essential oil grams per 100 grams of plant. The average specific mass of the
essential oil obtained was ρoil = 890 kg.m-3, the plant
specific mass determined using the pycnometer was ρplant = 1087 kg.m-3,
a moisture of 80.4% were determined and the plant particle diameter was equal
to 1.45 mm.
Table 1. Yield obtained through SFE and SD.
Pressure (bar) |
Global
yield (gOE/100g
plant) |
|
SDa |
1 2 3 |
0.78
0.83
|
SFEb |
80 90 100 110 |
0.07 0.21 0.04 |
a = saturated water vapor, b = fluid temperature 40 °C |
3.1 Analysis of the turmeric essential oil.
The primary constituents of turmeric
essential obtained via SFE were a-zingiberene (22.78-10.16 %), a-turmerone (24.12-11.38 %) and
ar-turmerone (22.48-10.8 %). These
results are in accordance with what was found by Carvalho et al. [27] but with lower content of β-turmerone and α-turmerone.
These authors did not report the higher levels of α-zingiberene found in this
work. The SD method showed that the
major compounds were a-zingiberene (35.42-23.11 %), a-turmerone (24.52-20.24 %) and b-sesquiphelandrene (17.95-13.21 %).
This is consistent with the results of Hwang et al. [28], although with lower levels of ar-turmerone. These
variations could be attributed to geographic location, genetic and
environmental factors, as reviewed in Ibáñez [29]. Table 2 shows the compounds found in the essential oil obtained using
different techniques and conditions, with their respective retention index and
area percentage. The major compounds for each extraction method are
highlighted.
Table 2. Chemical composition of Curcuma longa essential oil obtained by supercritical extraction and steam distillation under different extraction conditions.
Compoundsa |
RIb |
Steam Distillation Area
(%)c |
|
Supercritical Fluid Extraction Area (%)c |
|||||
1
bar |
2
bar |
3
bar |
80
bar |
|
90
bar |
100
bar |
110
bar |
||
1,8-Cineole |
1028 |
- |
0.56 |
- |
0.13 |
- |
- |
- |
|
Terpinolene |
1085 |
1.28 |
1.13 |
- |
0.07 |
- |
- |
- |
|
3Z-hexenilmetil
carbonate |
1100 |
- |
- |
- |
0.03 |
- |
- |
- |
|
2-Nonanol |
1101 |
- |
- |
- |
0.09 |
- |
- |
- |
|
Terpinen-4-ol |
1174 |
- |
- |
- |
0.05 |
- |
- |
- |
|
1,4-Cymene-8-ol |
1184 |
- |
- |
- |
0.16 |
- |
- |
- |
|
α-Terpineol |
1188 |
- |
- |
- |
0.27 |
- |
- |
- |
|
2-Decanol |
1202 |
- |
- |
- |
0.02 |
- |
- |
- |
|
2-Undecanol |
1301 |
- |
- |
- |
0.03 |
- |
- |
- |
|
δ-Elemene |
1335 |
- |
- |
- |
0.03 |
- |
- |
- |
|
Piperitenone |
1338 |
- |
- |
- |
0.13 |
- |
- |
- |
|
β-Elemene |
1389 |
- |
0.48 |
- |
0.12 |
- |
- |
0.07 |
|
Sesquitujene |
1404 |
- |
- |
- |
0.09 |
- |
- |
- |
|
E-Caryophyllene |
1415 |
- |
0.34 |
0.14 |
- |
- |
0.08 |
||
g-Elemene |
1431 |
- |
- |
- |
0.03 |
- |
- |
- |
|
E-α-Bergamotene |
1433 |
- |
- |
- |
0.04 |
- |
- |
- |
|
E-β-Farnesene |
1456 |
- |
0.54 |
- |
- |
- |
0.41 |
- |
|
Sesquisabinene |
1456 |
- |
- |
- |
- |
- |
- |
0.23 |
|
Z-β-Farnesene |
1456 |
- |
- |
- |
0.32 |
- |
- |
- |
|
g-Amorphene |
1477 |
- |
- |
- |
- |
- |
- |
0.08 |
|
Germacrene
D |
1477 |
- |
0.42 |
- |
0.09 |
- |
- |
- |
|
ar-Curcumene |
1481 |
4.02 |
3.6 |
5.17 |
1.49 |
1.45 |
3.31 |
1.79 |
|
α-Zingiberene |
1494 |
25.26 |
23.11 |
35.42 |
11.37 |
17.44 |
22.78 |
10.16 |
|
β-Curcumene |
1502 |
- |
- |
- |
0.09 |
- |
- |
- |
|
β-Bisabolene |
1507 |
2.6 |
2.53 |
- |
1.41 |
1.63 |
2.52 |
1.31 |
|
β-Sesquiphelandrene |
1522 |
14.41 |
13.21 |
17.95 |
6.65 |
8.85 |
12.58 |
6.41 |
|
E-g-Bisabolene |
1530 |
- |
0.27 |
- |
0.19 |
- |
- |
0.12 |
|
E-iso-g-Bisabolene |
1534 |
- |
- |
- |
0.09 |
- |
- |
- |
|
g-Cuprenene |
1543 |
- |
- |
- |
0.05 |
- |
- |
- |
|
Germacrene
B |
1553 |
- |
0.49 |
- |
- |
- |
0.55 |
- |
|
E-Nerolidol |
1563 |
- |
- |
- |
0.06 |
- |
- |
0.04 |
|
ar-Tumerol |
1579 |
- |
0.66 |
- |
0.26 |
- |
- |
0.38 |
|
E-β-Elemenone |
1602 |
- |
- |
- |
0.36 |
- |
- |
0.49 |
|
β-Atlantol |
1698 |
1.08 |
2.22 |
- |
- |
- |
- |
||
ar-Turmerone |
1664 |
11.33 |
9.76 |
10.48 |
22.07 |
10.8 |
12.43 |
22.48 |
|
a-Turmeroned |
1673 |
24.00 |
20.24 |
24.52 |
5.32 |
|
24.12 |
18.57 |
11.38 |
Helifolenol
A |
1687 |
- |
- |
- |
0.12 |
- |
- |
- |
|
Germacrone |
1692 |
4.36 |
4.52 |
2.77 |
3.36 |
2.86 |
3.76 |
||
b-Turmeroned |
1703 |
8.25 |
7.11 |
6.45 |
7.67 |
|
8.29 |
7.66 |
8.98 |
Curcuphenol |
1719 |
- |
- |
- |
0.25 |
- |
- |
0.44 |
|
Curcumenol |
1727 |
- |
- |
- |
0.85 |
- |
- |
0.75 |
|
6S,7R-Bisabolone |
1745 |
1.53 |
1.73 |
- |
1.84 |
1.6 |
- |
2.27 |
|
6R,7R-Bisabolone |
1754 |
- |
- |
- |
- |
- |
1.31 |
- |
|
β-Bisabolenal |
1770 |
- |
- |
- |
0.56 |
- |
- |
- |
|
E-α-Atlantone |
1775 |
0.83 |
1.38 |
0.21 |
- |
- |
0.25 |
||
Hexadecanoic
acid |
1973 |
- |
- |
- |
0.05 |
- |
- |
- |
|
dehydro-Juvibione |
1997 |
- |
- |
- |
0.08 |
- |
- |
- |
|
Total
identified |
- |
98.95 |
94.3 |
100 |
65.65 |
|
77.54 |
84.98 |
71.47 |
aCompounds
identified by comparing their mass spectrum and retention index with the
Adams library (2007). bRI retention
index calculated for a series of alkanes (C8-C20). cPercentage
area of each peak, according to the response of the mass detector, in
relation to the total area of the chromatogram, considering a response factor
equal to 1 for all components. dCompounds identified by comparing their mass
spectrum and retention index based on NIST library (2005). |
3.2 Principal Component Analysis
From the PCA, it was possible to observe that five components stood out from the others, a-turmerone, ar-turmerone, b-turmerone, b-sesquiphelandrene, and a-zingiberene as shown in Fig. 3.
In Fig. 3,
it is possible to observe the behavior of the composition of Curcuma longa
essential oil related to the pressure variation and the extraction method, it
can be noted the formation of two distinct groups. The first one demonstrates
higher scores on the first component, with zero or negative scores on the
second component. The second group, on the other hand, exhibits higher scores
on the second component, but lower scores on the first component. This division
of groups is attributed to the similarity of the area percentage of the
components identified by GC-MS. It was possible to visualize that there was
difference in the composition due to the different pressures used in the steam
extraction. The 3 bar condition had a higher score in the first component, with
an increase of α-zingiberene, a-turmerone and b-sesquiphelandrene
content, while at 1 and 2 bar the composition was similar. For the
supercritical extraction technique, it was possible to observe a variation in the composition obtained between the different
pressures. The similarity between the
pressures of 80 and 110 bar was observed, while 100 and 90 bar pressure
composition come closer to the SD method but with a lower first component
score, mainly due to the lower α-zingiberene and b-sesquiphelandrene
content. The first and second components explain 98.3% of the data variance.
Figure 3.
Variation in the behavior of turmeric essential oil, in relation to different
pressures and extraction methods.
SD extract presented higher concentrations of α-zingiberene, which can indicate that
its extract could be more effective in medicine in the treatment of some types
of human cancer (liver [30], colon [31], cervical, and breast cancers and leukemia [32]) as well as an antibacterial agent for food
industry [33]. The α-zingiberene compound is also potential
insecticide and can induce resistance to
diseases and pests in tomatoes [34-35]. The
SFE extract presented a higher concentration of ar-turmerone which has a
promising anticancer capacity, as cited before [7].
3.3 Mathematical Modeling
According
to the proposed methodology, mathematical modeling was carried out and the
results can be seen in Fig. 4. The modeling was realized for the highest yield
conditions (3 bar for SD and 90 bar for SFE). The estimated values for the
parameters, together with the coefficient of determination (R2) for
each method are presented in Table 3. The standard deviation for the yield of
SD curve was ± 0.1194% and for the SFE it was ± 0.1438%.
Table 3.
Parameters obtained through modeling of the experimental data for SD and SFE
methods.
Method |
K.104
m³.kg-1 |
kTM.104.
s-1 |
R2 |
SFE |
12.403 |
1.7915 |
0.9931 |
SD – Stage 1 |
0.9975 |
1.0671 |
0.9739 |
SD – Stage 2 |
1.1213 |
1.3905 |
0.9888 |
Figure 4.
Curves for SFE (90 bar and 313.15 K) and SD (3 bar and 406.15 K) and
mathematical modeling.
The best yield for supercritical extraction was at the condition of 90 bar and 40 °C. This is a condition close to the critical point where it is known that carbon dioxide has a higher density, which increases the solvent solubility. With the increase in pressure, maintaining a fixed temperature of 40 °C, it is known that the CO2 density and diffusivity compete with each other. As the diffusivity decreases, the density increases, as both affect the solvation capacity of supercritical carbon dioxide, it passes through a maximum condition depending on which variable is prevailing in the considered condition [36-37].
From the SD extraction curve, it was possible to identify the presence of two different regimes. The first regime was identified as a curve of low slope followed by the second regime that ends with the depletion of the plant. This difference in mass transfer between these different periods for extraction can be explained by a change in the type of solute being removed, there are volatile compounds that are preferentially removed in an initial step. Afterwards, the matrix continues to provide extract mass, but this last is composed of different chemical species. With this, the mass balance for two pseudo components was considered, one leaving in the first stage and the other in the second stage. Thus, it was necessary to estimate the mass transfer parameters for each of these regimes. The regime change time was estimated based on the graphical analysis, occurring within 140 minutes.
The coefficient of determination corresponds to the adherence of the model to the experimental data. For both extractions, the coefficient indicates that the model is adequate to fit the experimental data.
The K parameter is the equilibrium constant between the phases, which proved to be greater for the SFE, indicating that the equilibrium is predominant in the extraction compared to the SD, which obtained a lower order equilibrium constant. The kTM parameter, which indicates mass transfer, had the same magnitude for both techniques. It is also worth mentioning that the SFE method could achieve 0.8% yield way faster than SD method, being more time efficient than SD. The parameters obtained are in the expected order of magnitude, for SFE and SD [38].
4.
Conclusions
It was possible to evaluate the
performance of the SD technique and SFE, with higher yields being obtained at
pressures of 3 bar and 90 bar, respectively. The chromatographic analysis of
the extracts showed α-zingiberene as the major compound
for the SD technique and ar-turmerone and a-turmerone for the SFE. From the PCA it was observed
that the pressure did not significantly influence the composition of the
essential oil for the SD. For the SFE, a similarity was identified between the
composition of 90 bar and 110 bar, with the influence of the pressure on the
extract composition. The mathematical modeling of the processes was carried out
and the relevant parameters were obtained, with the SD technique composed of
two periods. It was observed that the SFE was greater influenced by the process
equilibrium in relation to the SD technique. It is possible to indicate that SD
extract is more indicated for applications that need α-zingiberene and SFE
extract for uses that request higher concentrations of ar-turmerone. The data
obtained from the mathematical modeling support for the studies of change from a pilot scale to an
industrial scale. In future work, the chemical composition of the extract will
be monitored throughout the extraction, in order to validate the hypothesis of
extraction of two types of solute and to help determine the parameters of the
mass transfer model used for the steam distillation.
Authors’ contributions
Conceptualization, ET.S.J.; RN.A.; E.C. and R.M.F.V; Methodology, E.T.S.J. and A.M. L.; Formal Analysis, E.T.S.J.;
R.N.A. and A.M.L.; Data Curation, E.T.S.J.; Writing – Original Draft Preparation, E.T.S.J.; Writing–Review &
Editing, A.M.L.; Supervision, R.N.A.; A.M.L.; E.C. and R.M.F.V.; Funding Acquisition, E.C. and R.M.F.V.
Acknowledgements
The authors thank the Laboratory of Unit Operations (LOPE) and the Pontifical University of Rio Grande do Sul.
Funding
This work was supported by the Polytechnic School of Pontifical Catholic University of Rio Grande do Sul.
Conflicts of interest
The authors declare that they have no
known competing financial interests of or personal relationships that could have appeared to
influence the work reported in this paper.
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This work is licensed under the
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License (CC BY-NC 4.0).
Abstract
This study aims to compare the supercritical extraction (SFE) and steam
distillation (SD) to obtain the Curcuma longa essential oil, evaluating the
yield and composition for different conditions, as well as the mathematical
modeling of the extraction curve. Analysis of the chemical composition of the
essential oil was performed by gas chromatography coupled to mass spectrometry
(GC-MS). The experimental extraction curve was plotted, and a mathematical
model was used to fit the data for the SD and SFE methods. The data indicate
that the best condition for SFE is 90 bar, 40 ° C (0.0219 goil/gplant)
with 10.80% ar-turmerone and 24.12% a-turmerone, for SD the one performed at 3 bar (133
° C) (0.0486 goil/gplant) with 35.42% α-zingiberene and
24.52% a-turmerone. Different major compounds were obtained varying the
extraction technique. The mathematical modeling adequately represented the
extraction processes.
Abstract Keywords
Steam distillation, supercritical
extraction, chromatography, modeling, composition, Curcuma longa.
This work is licensed under the
Creative Commons Attribution
4.0
License (CC BY-NC 4.0).
Editor-in-Chief
Prof. Dr. Radosław Kowalski
This work is licensed under the
Creative Commons Attribution 4.0
License.(CC BY-NC 4.0).