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Vol. 23, No. 02, pp. 259 - 266, April - June, 2006

ISSN 0104-6632 Printed in Brazil www.abeq.org.br/bjche

EXTRACTION OF HO-SHO (Cinnamomum camphora NEES AND EBERM VAR. Linaloolifera fujita) ESSENTIAL OIL WITH SUPERCRITICAL CO2: EXPERIMENTS AND MODELING

E. Steffani1*, A. C. Atti-Santos2, L. Atti-Serafini2 and L. T. Pinto3

Departamento de Engenharia Química, Centro de Ciências Exatas e Tecnologia, Phone: +(55) (54) 3218-2100, Ext. 2266, Fax: +(55) (54) 32182100 Ext. 2253, Universidade de Caxias do Sul, CEP 95001-970, Caxias do Sul - RS, Brazil. E-mail: esteffan@ucs.br 2 Instituto de Biotecnologia, Universidade de Caxias do Sul, CEP 95001-970, Caxias do Sul - RS, Brazil. 3 Departamento de Engenharia Química e de Alimentos, Centro Tecnológico, Universidade Federal de Santa Catarina, CEP 88040-900, Florianópolis - SC, Brazil. (Received: October 20, 2004 ; Accepted: March 6, 2006)

1

Abstract - Supercritical CO2 extraction of essential oil from the leaves of a variety of camphor tree known as Ho-Sho was studied. Experiments were carried out within the following ranges: CO2 flow rate (1 - 4 mL/min); pressure (80 - 100 bar); temperature (40 - 60 oC) and particle size (0.37 - 1.0 mm). The equipment used was an HP 8670 T extractor module with an extraction cell volume of 7 mL. Two mathematical models of the process were proposed. Model 1 was a modified version of the traditional shrinking core model with effective diffusivity and the external mass transfer coefficient as the fitting parameters. Model 2 used an additional kinetic parameter based on an Arrhenius-like expression. Both models took into account the cell pressurization step. The best fit between the extraction model curves and the experimental data was obtained using model 2. Keywords: Supercritical extraction; Essential oil; Ho-sho; Mathematical modeling.

INTRODUCTION Linalool is an important intermediary in the manufacture of vitamin E and, like geranial, is raw material for the production of vitamin A (Bauer and Garbe, 1985). Linalool can be synthesized by different chemical routes from α-pinene or from isoprene. The world consumption of linalool in 1988 was estimated at six million metric tons (Clark, 1988) and it is growing year after year, because it is used not only for the production of vitamins, but also in the fragrance industry. An alternative for the production of linalool from a natural source is the

*To whom correspondence should be addressed

essential oil obtained from a plant known as ho-sho (Cinnamomum camphora Nees and Eberm var. linaloolifera Fujita), which is a tree native to China, Formosa and Japan. The main component of ho-sho essential oil is linalool (80-90%). Natural sources of linalool are of interest, mainly to the fragrance industry, because the smell of plant materials is usually the result of complex interactions among the components of the mixture (Reverchon, 1997). In this work we studied the extraction of ho-sho essential oil using supercritical CO2 as solvent, because this process produces oils of excellent quality and also is an example of clean technology.

All the analyses were carried out in a gas chromatograph HP GC 6890 Series. Atti-Santos.37 0. Therefore.00 0. Quantachrome.0 1. the oil obtained at predefined time intervals was collected in separate flasks and the data points were used to plot the extraction curves. After the drying period the leaves were ground using a Tecnal TE-650 mill (Tecnal. the equation for the fluid phase in the pressurization stage can be written as Brazilian Journal of Chemical Engineering .5 kg/m3 and 6.5 2. from 180 to 230°C at 20 °C/min. It was also assumed that the other oil components had the same response factor.00 1. Thus. USA).0 2. the initial conditions for the extraction stage will be the ones obtained by the end of the pressurization stage.0 Pressure (bar) 80 90 100 80 90 100 80 90 100 Temperature (oC) 40 50 60 50 60 40 60 40 50 Particle Size (mm) 0. 97% purity) was chosen as internal standard for having a molar mass close to that of linalool. 0. Gas chromatography using an internal standard was the method used for quantification of the essential oil extracted. Tyler sieves were used to classify particles by desired size fractions (average diameters of 0. Brazil). A. besides the extraction stage itself. H2 was the carrier gas.50 0.0 1. The experimental extraction runs with supercritical CO2 were carried out in a HewlettPackard 7680 T extraction module and followed a 3x3 graeco-latin square design type.71. the split ratio was 1:50. The injector temperature was 250 °C. In accordance with this criterion. Steffani. Atti-Serafini and L. Extractor pressurization was conducted isothermally.00 0. Pinto MATERIALS AND METHODS Ho-sho leaves from exemplars of plants at the Biotechnology Institute of the University of Caxias do Sul were picked and dried under controlled conditions (temperature 20-22 oC and relative air humidity 50-60%) during a period of seven days. USA. The density of the porous solid matrix and the tortuosity of the solid were determined with a mercury intrusion assay using Poresizer 9320 equipment (Micromeritics.50 1.58. Then the particles were introduced into the extraction cell. equipped with a data acquisition software (HP Chemstation).37 0.0 4.50 mm and 1. The fluid properties are assumed to be dependent only on time. the total amount of essential oil extracted was calculated using the results of the chromatographic analysis and the extract yield was determined. and the value obtained was 1314 kg/m3. the fluid phase is modeled as an infinite bath. This method consists in adding a given amount of a substance (which is called the standard) to the extract before the chromatographic analysis.5 2. CO2 density was estimated using the Peng-Robinson equation of state. the variation in pressure with time was measured and then fitted by an algebraic expression.50 1. USA). This substance must have a response factor similar to that of the main components of the extract.37 For each run. 3-octanol (Aldrich. the main component in the extracted essential oil. In the pressurization stage. The column temperature varied from 40 °C (8 minutes) to 180 °C at 3 °C/min.0 μL. L. 230 °C (20 minutes). an FID detector (Flame Ionization Detector) and a fused silica capillary column HP-Innowax (30 m x 320 μm). T. For each experiment. The skeletal density of the solid was determined using a helium pycnometer (Ultrapycnometer 1000. MATHEMATICAL MODELING The proposal presented in this work includes the mathematical modeling of the extractor pressurization stage. respectively.37 mm.0 4. From the density of the porous solid and the skeletal density it was possible to determine the porosity of the solids as being 0. obtaining the values of 544. whose internal volume was about 7 mL. the column head pressure was 34 kPa and the injected sample volume was1.260 E.5 4. according to the experimental matrix presented in Table 1: Table 1: Experimental matrix Run 1 2 3 4 5 6 7 8 9 Flow Rate (mL/min) 1. C. Thus.0 mm).

where it is known as the “nonreacted core model”. t) r =R ε R ( ) (1) where C1 is the solute concentration in CO2 in the bed void volume. Thus. the fluid phase equation is obtained assuming the axial dispersion term and the process occurring under isothermal and isobaric conditions.0) = C1 (t = pressurization time) (∀z) Boundary conditions: z = 0. t) = 0 (∀ t) ∂z (4) r = rc 1 . if Cp 1 (r. t) ⎞ ⎜ ⎟− = + ⎟ r εp ⎜ ∂r ∂r 2 ⎝ ⎠ (1 − ε) 3k f − C(z. t) ∂C(z.Extraction of Ho-Sho (Cinnamomum camphora Nees and Eberm Var. (1996) and improved by Spricigo (1998).0) = 0 (∀r) Boundary conditions: (8) is the solute concentration in the pore volume of solid at the surface of the particle in the extraction stage and z is the axial coordinate. k f1 is the external film mass transfer coefficient. Initial condition: Cp 1 (r. The solute diffuses inside the pores in the region between core surface ( r = rc ) and particle surface (r = R) . The solubility of the essential oil was calculated from the results of Chang and Chen (1999). Initial condition: C1 (0) = 0 (2) For the extraction stage. 259 . the boundary condition for the pore oil concentration becomes a symmetry condition. t) ∂ C(z. Cp r =R where Def1 is the effective diffusivity in the extractor pressurization stage. k f is the external film mass transfer coefficient in the extraction stage. April . 2006 . ε p is the porosity of the solid and r is the radial coordinate. 23. ρ1 is the density of CO2. t) − D L ∂C(z. t) r =R ε R ( ) (3) Cp 1 (r. ∂Cp 1 (r. The resulting equation is ∂C(z. traditionally used in the chemical reactor area. ε is the voidage of the extraction bed. Linaloolifera fujita) Essential Oil 261 dC1 (t) C (t) dρ (t) =− 1 ⋅ 1 − ρ1 (t) dt dt (1 − ε) 3k f1 (t) − C1 (t) − Cp 1 (r. two distinct models based on differential method of rate analysis are proposed. t) dρ1 (t) ρ1 (t) dt (7) where C is the solute concentration in CO2 in the bed void volume in the extraction stage. Cp1 r =R is the solute concentration in the pore volume of solid at the surface of the particle and t is time. t) ∂t − 2 Def1 (t) ⎛ ∂ Cp 1 (r.June. It is assumed that. No. Initial condition: C(z. The equation that governs mass transfer inside the particle pores assumes an effective diffusivity for the oil in the CO2. 02. ∂C(z. R is the particle radius. The model assumes the existence of a solute core inside a spherical particle that will decrease continuously during extraction. t) ∂r = 0 (symmetry) (10) z = L. the model obtained for the solid phase can be written as Pressurization stage: ∂Cp 1 (r. t) = Csat 1 (t) (9) rc 1 ≠ 0 (5) r = rc 1 . Model 1 is based on the shrinking core model. t) − Cp (z. vC(z. t) 2 ∂Cp 1 (r. t) = 0 (∀ t) ∂z (6) if rc 1 = 0 Brazilian Journal of Chemical Engineering Vol.266. pp. the solvent is always saturated. initially adapted by Roy et al. on the core surface. r. t) = DL −ν − 2 ∂t ∂z ∂z 2 For the mass balance in the solid phase. DL is the axial dispersion coefficient. When the core vanishes. assuming the oil to be pure linalool. ν is the interstitial velocity of solvent in the bed.

t) = ⋅ ⋅ ∂t C N ρs ∂r r =r (18) Extraction stage: ∂Cp (z. Steffani. r. Brazilian Journal of Chemical Engineering .r. t) Csat1 (t) − Cp1 (r. t) ⎞ ⎜ ⎟− = + ⎟ r εp ⎜ ∂r ∂r 2 ⎝ ⎠ The present proposal for calculation of the shrinkage of the core differs from that of Spricigo (1998).0) = Cp1 (r. r. t) ∂r r =R = kf C(z. L. In this work it is assumed that the variation in oil mass in the core is equal to the oil mass flow rate at the surface of core multiplied by the surface area of the core. Cp (z. Initial condition: Cp (z.t) ∂r r=R = kf1(t) C1(t) − Cp 1(r. t) ∂r = 0 (symmetry)if rc = 0 (15) Model 2 makes use of a differential equation for diffusion inside the pores that is applied to the whole particle domain (different from model 1 where diffusion takes place outside the core region) and an equation for mass transfer from solid to fluid based on oil solid concentration and the distance from saturation in the fluid phase. t) 2 ∂Cp 1 (r. the equations for the solid phase in model 2 are Pressurization stage: (16) Def ∂Cp (z.0) = C N (∀r) (23) (24) where C N is the initial solid phase concentration and ρs is the density of the porous solid matrix.t) ( r=R ) (∀t) rc 1 (0) = R Extraction stage: ∂rc (z. Therefore. t) ⎞ ⎜ ⎟ (12) + ⎜ ⎟ ∂r r ∂r 2 ⎝ ⎠ (19) c where ρ is the density of CO2 in the extraction stage. r.0) = rc1 (t = pressurization time) (∀z) (20) where Def is the effective diffusivity in the extraction stage and Cp is the solute concentration in the pore volume of solid in the extraction stage. A radial gradient of solid oil concentration. t) 2 ∂Cp (z. r. t) dρ1 (t) ρ1 (t) dt ρs ∂q1 (r. r. t) Def ρ ∂Cp (z.262 E. t) ( ) (22) where q1 is the solute concentration in the solid phase in the extractor pressurization stage and K is a kinetic parameter. t) ∂t D = ef εp ⎛ ∂ 2 Cp (z. A. t) ( r =R ) (∀t) ∂Cp 1 (r. t) ∂t − 2 Def1 (t) ⎛ ∂ Cp 1 (r. t) − εpρ1 (t) ∂t (21) ∂q1 (r. r. Atti-Serafini and L. if rc ≠ 0 (14) ∂Cp (z. t) ⋅ ⋅ CN ρs ∂r r =r (17) c1 Cp 1 (r.0) = 0 (∀r) q1 (r. t) = Csat r = rc .r. t) = − K(T) ρ1 (t) ∂t q1 (r. Initial conditions: Cp 1 (r. After the algebraic calculation the equations obtained for both stages of the process become Pressurization stage: drc 1 (t) dt = Def1 (t) ρ1 (t) ∂Cp 1 (r. t = pressurization time) (∀z) (13) Boundary conditions: r = rc . Atti-Santos. r = R. t) − Cp (z. Initial condition: (11) Def1(t) ∂Cp 1(r. Pinto r = R. C. instead of an average concentration value as is usually seen in the literature was assumed. T. Initial condition: rc (z. r.

the final values obtained for each experiment were from one to two orders of magnitude smaller than the initial estimates. 23.t) ∂t − = Def εp ⎛ ∂2Cp (z.June.i is the accumulated oil mass extracted up to the time corresponding to point i.i ) 2 (33) ∂q(z. r. No. r.Extraction of Ho-Sho (Cinnamomum camphora Nees and Eberm Var. obtained experimentally.t) εpρ ∂t (27) ∑ (M i n calc. r.t) ( r=R ) (∀t) Extraction stage: ∂Cp (z. in case of model 2. t) ∂t ( ) where n is the number of experimental points for each run. the external film mass transfer coefficient (kf). using an Arrhenius-like expression.266. As the value for the frequency factor was somewhat arbitrary.t) ∂r r=R = kf C(z. the kinetic coefficient (K) were used as the fitting parameters. 2006 . the effective diffusivity Brazilian Journal of Chemical Engineering Vol.0 x 1013 m3kg-1s-1 and an activation energy of 1.r. t) ∂r = 0 (symmetry) (25) r = R. The initial estimates for the external film mass transfer coefficient were obtained by Wakao and Kaguei’s (1982) correlation.r. 02. t = pressurization time) (∀z) Boundary conditions: (30) r =0. r. which makes it more difficult to correlate the effective diffusivity with the oil-CO2 binary diffusivity. The initial guess for the kinetic parameter (K).0) = C p1 (r. M calc. by minimizing an objective function (F).0 x 105 J/mol. defined by F= ρs ∂q(z. resulted in values from one to two orders of magnitude smaller than the values obtained at the end of optimization. in both models a low sensitivity to the external film mass transfer coefficient was verified. April . obtained with an Arrhenius-like equation. The initial estimates for the kinetic parameter (K) were obtained as a function of temperature. r. t) ∂r = 0 (symmetry) (31) (32) Def ∂Cp (z. through spatial discretization using finite differences followed by an integration in time using Euler’s method. as reported by Gaspar et al.r.i is the accumulated extracted oil (28) mass up to the time corresponding to point i. (26) Def1(t) ∂Cp1(r.0) = q1 (r. indicating that extraction is controlled by intraparticle mass transfer.r. using a value for the frequency factor of 1.r.r. t = pressurization time) (∀z) (29) q(z. The models were solved by the method of lines.. 259 . During the optimization process. Thus.e.t) ∂r r=R = kf1(t) C1(t) − Cp1(r. Initial conditions: Cp (z. pp. ∂Cp1 (r. a correction of this factor could be incorporated. allowing better initial estimates. r.t) ( r=R ) (∀t). by a process of trial and error. For the effective diffusivity the starting value was obtained with the equation proposed by Pinto (1994). t) Csat − Cp (z. The parameters were optimized without using a specific algorithm. The axial dispersion coefficient was estimated by a correlation proposed by Tan and Liou (1989). (2003). i.t) 2 ∂Cp (z. The difficulty faced in this parameter prediction is associated with the fact that different vegetal structure types have different mass transfer resistances. Linaloolifera fujita) Essential Oil 263 Boundary conditions: r =0. t) = −K(T) ρ q(z.t) − Cp (z. r=R ∂Cp (z. the option was to keep the values of these parameters obtained directly by Wakao and Kaguei’s (1982) correlation. Related to the effective diffusivity parameter. obtained by simulation and M exp. The results obtained in the optimization are reported in Table 2: where q is the solute concentration in the solid phase in the extraction stage.i − M exp.t) ⎞ ⎜ ⎟− + ⎜ ⎟ ∂r r ∂r2 ⎝ ⎠ (Def) and. RESULTS AND DISCUSSION In the simulations performed.

Pinto Table 2: Values of optimized model parameters Run 1 2 3 4 5 6 7 8 9 kf x 104 (m/s) 3. The depletion of oil in the particles begins at the inlet of the extractor. In Figure 2. 4.717 x 10-11 2. Atti-Santos. C.433 x 10-2 3.085 x 10-11 3. A.513 2.00E-2 Experimental Model 1 1. L. a change in the curves due to the gradual reduction of the core can be noted.00E+0 0 2000 4000 6000 8000 0.287 x 10 -12 K (m3kg-1s-1) 2.00E-2 1.146 x 10 -12 Def (m2/s) Model 2 2.489 x 10-4 1.00 0.163 x 10-11 5. The variation in core size (Model 1) with time and axial position in the extractor for run 4 is shown in Figure 4.00E-2 Pore oil concentration (kg oil/kg CO2) 2.634 x 10-11 1.895 2.269 x 10-11 1.580 x 10-10 1.537 x 10-12 7.60 0. Figure 2: Profiles for pore concentration in the extraction stage at the inlet of the extractor generated by Model 1 (run 4). T.308 x 10-11 6.00E-2 t = 40 min t = 50 min t = 120 min Model 2 0.00E-2 Mass of extracted oil / Mass of plant fed 3.127 x 10-11 2.182 5. It includes the pressurization stage besides the extraction stage.00 Time (s) Core radius / Particle radius Figure 1: Superposition of experimental and model extraction curves for run 2.024 x 10-11 7.728 x 10-3 2.771 x 10-11 The extraction curves for run 2 are shown in Figure 1. where the solid is in contact with pure CO2 and extends in the direction of the outlet.141 x 10-3 3.700 x 10-2 9. Brazilian Journal of Chemical Engineering .00E-2 3.525 1.340 x 10-1 6.058 x 10-2 6.316 4.20 0.302 4. Steffani.047 x 10-4 2. Atti-Serafini and L. where the results for both models were obtained with the optimized parameters.631 x 10-11 4.00E+0 0.351 2.700 x 10-11 4.834 x 10-11 4.00E-2 t = 1 min t = 5 min t = 10 min t = 20 min t = 30 min 2.80 1. In general.991 2.309 x 10-11 7. the best agreement between the experimental data and the calculated values was obtained with model 2.406 Def (m2/s) Model 1 4. Figures 2 and 3 show respectively the concentration profiles in the pores of the particles at the inlet of the extractor (z = 0) for run 4 in model 1 and model 2.264 E.105 x 10-12 8.40 0.087 x 10-2 1.

20 0. a temperature of 60 oC. Linaloolifera fujita) Essential Oil 3. two mathematical models were proposed to represent the process of supercritical extraction of essential oil from leaves of a plant known as ho-sho. r.40 0. 23. Additional work has to be done for correlate the effective diffusivity with the oil-CO2 binary diffusivity. the largest essential oil yield obtained (4.00 0. It was found that extraction is controlled by intraparticle mass transfer. Both models contemplated the initial stage of extractor pressurization.80 z = L/2 z=L Pressurization stage 2.00E-2 t = 1 min t = 5 min t = 10 min t = 20 min 0.00E+0 0. using CO2 as solvent.5 mL/min and a particle size of 0. a CO2 flow rate of 2. t) In this work.60 0.20 0. pp.00 0 1000 2000 3000 Dimensionless radial position in the particle (r/R) Time (s) Figure 3: Profiles for pore concentration in the extraction stage at the inlet of the extractor generated by Model 2 (run 4). NOMENCLATURE Latin Letters C1 (t) solute concentration in CO2 in the bed void volume in the extractor (kg oil/kg CO2) pressurization stage solute concentration in (kg oil/kg CO2) CO2 in the bed void volume in the extraction stage initial solid phase (kg oil/kg solid) CN concentration Cp 1 (r.37 mm. t) solute concentration in (kg oil/kg CO2) the pores of the solid in the extractor pressurization stage Cp (z. Figure 4: Dimensionless core radius in different axial positions as a function of time generated by Model 1 (run 4). No.266. which differentiates this work from previous research found in the literature.40 1.Extraction of Ho-Sho (Cinnamomum camphora Nees and Eberm Var. depending on the volume of the extractor and the capacity of the pump.00 z=0 Pore oil concentration (kg oil/kg CO2) Core radius / Particle radius 0.60 0. 259 .June. This can be important in the scale-up of the process.00 0. 02. 2006 . The model that best reproduced the extraction curves was model 2. which used a nonconventional kinetic parameter based on an Arrhenius-like equation.00E-2 t = 30 min t = 40 min t = 50 min t = 120 min 0.00E-2 265 1. April . For the set of experiments performed. CONCLUSIONS C(z.31% w/w dry weight basis) occurred under the following conditions: a pressure of 90 bar.80 1. t) solute concentration in (kg oil/kg CO2) the pores of the solid in the extraction stage saturation concentration (kg oil/kg CO2) Csat 1 (t) of solute in the fluid phase in the extractor pressurization stage saturation concentration (kg oil/kg CO2) Csat of solute in the fluid phase (m2/s) Def1 (t) effective diffusivity in the extractor pressurization stage effective diffusivity in (m2/s) Def the extraction stage axial dispersion (m2/s) DL coefficient external film mass (m/s) k f1 (t) transfer coefficient in the Brazilian Journal of Chemical Engineering Vol.

Lu. T. L. C. S. Federal University of Santa Catarina. Modelling the Extraction of Essential Oils with Compressed Carbon Dioxide. M. Eng. and Kaguei. T. Linalool.. D. Gordon and Breach. Brazil (1998). Properties and Uses. S. N. thesis. p.. Res. C. Chem. Goto. VHC. 607 (1996). E. Weinheim (1985).. diss. Journal of Supercritical Fluids. 28. L. Clark. and Al-Duri. Steffani. C. Brazilian Journal of Chemical Engineering . 35.. Common Fragrance and Flavor Materials: Preparation. Ind. 25. t) r rc 1 (t) rc (z. Perfumer & Flavorist.119 (1999). C. M. New York (1982).. Heat and Mass Transfer in Packed Beds. Axial Dispersion of Supercritical Carbon Dioxide in Packed Beds. K. Chem. R. Chang. Um Estudo do Transiente da Difusão Gasosa em Meios Porosos.. D. Pinto kf K L q1 (r.. Eng.. Florianópolis-SC. Ind. p. S. J. Sc. p. A. 10. and Chen.. 13. Journal of Supercritical Fluids.. G. Spricigo. Reverchon. p.. 247 (2003). Roy. 1 (1997). Tan. 49 (1988). Sc. Fluid Phase Equilibria.. C. M. 163. T. B. r. Santos. Atti-Santos. B. p... Atti-Serafini and L. Brazil (1994). Extração de Óleo Essencial de Noz Moscada com Dióxido de Carbono a Altas Pressões. C. Wakao. t) q(z. Res. 1246 (1989). B. Supercritical Fluid Extraction and Fractionation of Essential Oils and Related Products. T. t) R t T z extractor pressurization stage external film mass (m/s) transfer coefficient in the extraction stage kinetic parameter (m3 kg-1s-1) bed length (m) solute concentration in the (kg oil/kg solid) solid phase in the extractor pressurization stage solute concentration in (kg oil/kg solid) the solid phase in the extraction stage radial coordinate in the (m) particle core radius in the extractor (m) pressurization stage core radius in the (m) extraction stage particle radius (m) time (s) temperature (K) axial coordinate (m) REFERENCES Greek Letters ε εp voidage of the extraction (dimensionless) bed porosity of the solid (dimensionless) interstitial velocity of solvent in the bed density of CO2 in the extractor pressurization stage density of CO2 in the extraction stage density of the porous solid matrix (m/s) (kg/m3) (kg/m3) (kg/m3) v ρ1 (t) ρ ρs Bauer. Extraction of Ginger Oil with Supercritical Carbon Dioxide: Experiments and Modeling. p. Rio de Janeiro-RJ. High-pressure Densities and P-T-x-y Diagrams for Carbon Dioxide + Linalool and Carbon Dioxide + Limonene.. and Liou. and Garbe. Pinto.266 E. C. Gaspar. COPPEFederal University of Rio de Janeiro. D. F. C. and Hirose..

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