Measurement and Correlation of Derivatized Anthraquinone Solubility

Article pubs.acs.org/jced

Measurement and Correlation of Derivatized Anthraquinone Solubility in Supercritical Carbon Dioxide Ratna Surya Alwi and Kazuhiro Tamura* Division of Natural System, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192 Japan ABSTRACT: Solubilites of 1,4-diamino-2,3-dichloroanthraquinone (C.I. Disperse Violet 28) and 1,8-dihydroxy-4,5dinitroanthraquinone in supercritical carbon dioxide (sc-CO2) were measured at the temperature of (323.15, 353.15 and 383.15) K and over pressure ranges (12.5 to 25.0) MPa by a flow-type apparatus. Mole fraction solubility of 1,4-diamino2,3-dichloroanthraquinone (C.I. Disperse Violet 28) is found significantly higher than that of 1,8-dihydroxy-4,5-dinitroanthraquinone. It was found that 2,3-dichloro group addition onto 1,4-diaminoanthraquione leads to higher solubility of 1,4diaminoanthraquinone and the addition of 8-hydroxy-5-nitro group on 1-hydroxy-4-nitroanthraquione causes lower solubility than that of 1-hydroxy-4-nitroanthraquinone. Three semiempirical density-based models, Mendez−Santiago−Teja, Sung− Shim, and Bartle et al., were used to correlate the experimental results. Moreover, the solubilities of anthraquinone derivatives were analyzed thermodynamically by the regular solution model with the Flory−Huggins theory and by the Peng−Robinson equation of state with a modification of Stryjek and Vera (PRSV-EOS). The calculated solubilities of anthraquinone derivatives were in good agreement with the experimental results.

1. INTRODUCTION Carbon dioxide has low critical properties of temperature and pressure, Tc (304.15 K) and Pc (7.383 MPa). In addition, carbon dioxide is inexpensive, nonflammable, and nontoxic. Currently, supercritical carbon dioxide (sc-CO2) is considered as one of the green acceptable solvents, and brings a new innovation to textile dyeing technology. In the sc-CO2 dyeing process, sc-CO2 molecules permeate the synthetic fibers, acting as a swelling agent, and the glass transition temperature of the fibers is lowered by the penetration of CO2 molecules into the polymer. Simultaneously sc-CO2 can make dyestuffs soluble in the sc-CO2 phase and the dyes can diffuse into the fibers. The sorption of dyes in the polymer depends upon the solubility of the dyes as well as the dye transportation and stainability into a polymer. In the past few decades, the supercritical dyeing process has been developed on an industrial scale at operation up to 30 MPa.1 In the development and design of the supercritical dyeing process, the solubility of dyestuffs and the phase behavior should be well-known primarily. Among the dyestuffs used in dyeing processes, there exist anthraquinone derivatives formed by several functional groups. As evidenced from the current measurements,2−8 the solubility of anthraquinone derivatives changes variously with the substitutional groups on the anthraquinone. To understand the solubility of anthraquinone dyestuffs in sc-CO2, one needs to find out the effect of substituted groups in anthraquinone systems on the solubilities in sc-CO2. So far we have reported the solubility of anthraquinone compounds including −NH2, −NO2, and −OH groups in sc-CO2.9,10 In the present work, we measured the © XXXX American Chemical Society

solubility of two anthraquinone derivatives, namely, 1,4diamino-2,3-dichloroanthraquinone (C.I. Disperse Violet 28) and 1,8-dihydroxy-4,5-dinitroanthraquinone in sc-CO2 to clarify how the solubility of anthraquinone compounds in sc-CO2 changes with the substitutional groups on the anthraquinone. The solubilities of anthraquinone derivatives were correlated with three different types of semiempirical equations proposed by Mendez-Santiago−Teja,11 Sung−Shim,12 and Bartle et al.13 Moreover the experimental solubilities were calculated by the regular solution model with the Flory−Huggins theory9,10,14 as well as the Peng−Robinson equation of state modified by Stryjek and Vera (PRSV-EOS)15,16 with the van der Waals onefluid mixing rule.

2. EXPERIMENTAL SECTION The chemicals used are presented in Table 1. These materials were used directly without any further purification. The solubility measurements of anthraquinone derivatives were made using a flow system equipment. A detailed description of the apparatus is given elsewhere.9,10,17−19 The standard uncertainties (0.95 level of confidence) of the temperature and pressure measurements were within up to 0.1 K and 0.1 MPa, respectively. The flow diagram of the experimental setup is shown in Figure 1. The equilibrium cell (150 mm in length Received: June 12, 2015 Accepted: September 4, 2015

A

DOI: 10.1021/acs.jced.5b00480 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data

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flowing out of the cell. The solubility of anthraquinone was obtained by the anthraquinone concentration and volume of CO2. Equilibrium solubility was attained when the flow rate of CO2 in a high-pressure liquid pump was 2 cm3/min and the length of contact time of CO2 in the dissolution column was longer than 30 min. Three replicates were carried out at each experimental condition. The experimental solubility obtained was as an average of the measured results. The experimental average relative standard deviation of the solubility measurements for 1,4-diamino-2,3-dichloroanthraquinone (C.I. Disperse Violet 28) was 3.66 %, and for 1,8-dihydroxy-4,5dinitroanthraquinone was 5.64 %.

Table 1. Chemical Formula, Source, and Purity of the Chemicals chemical name 1,4-diamino-2,3-dichloroanthraquinone C.I. disperse Violet 28 (C14H8Cl2N2O2) CAS number 81-42-5 1,8-dihydroxy-4,5-dinitroanthraquinone (C14H6N2O8) CAS number 81-55-0 carbon dioxide ethanol acetone

source Tokyo Chemical Industry CO., LTD Tokyo Chemical Industry CO., LTD Uno Sanso Japan Alcohol Trading Company Wako Pure Chemicals

mass fraction purity/% > 93 > 98 > 99.9 > 99.5

3. RESULTS AND DISCUSSION 3.1. Experimental Solubility Data. Table 2 presents the experimental solubilities of two kinds of anthraquinone dyestuffs in sc-CO2 over the pressure range from 12.5 to 25.0 MPa and at the isotherm of (323.15, 353.15, and 383.15) K, together with the CO2 density calculated by the Span−Wagner equation of state.20 The solubility increases with increasing system temperature and pressure. As shown in Figures 2 and 3, the solubility isotherm for 1,8-dihydroxy-4,5-dinitroanthraquinone at 323.15 K has a crossover point at pressure range of about 17 MPa to 19 MPa for the isotherms at 353.15 K and 383.15 K. The crossover point was slightly different from 1,4diamino-2,3-dichloroanthraquinone that has a crossover point at pressures about at 17 MPa to 20 MPa. It is important to note that the solubility change exhibits a different trend at the crossover boundary region, as the same observed in previous experimental studies.21 Figure 4 compares the solubility of 1,4diamino-2,3-dichloroanthraquinone in sc-CO2 with that of 1,4diaminoanthraquinone reported previously.9 The chloro group addition onto the aminoanthraquinone causes higher solubility of the anthraquinone. Figure 5 shows that the addition of the hydroxy and nitro groups on 1-hydroxy-4-nitroanthraquinone10 causes lower than the solubility of 1-hydroxy-4-nitroanthraquinone. It was found that the solubility changes with the order of 1-hydroxy-4-nitroanthraquinone > 1,4-diamino-2,3-dichloroanthraquinone > 1,4-diaminoanthraquinone > 1,8-dihydroxy-4,5dinitroanthraquinone, and 2,3-dichloro group in addition onto 1,4-diaminoanthraquinone leads to higher solubility, but 8hydroxy-5-nitro group leads to much lower solubility of 1hydroxy-4-nitroanthraquinone. The solubility changes of anthraquinone derivatives in sc-CO2 by the substituent groups on the anthraquinone were in accordance with the trend results from the molecular interactions among the CO2 molecule with functionalized benzenes consisting of −OH, −NH2, and −NO2 substituents examined by using the density functional theory.22 3.2. Empirical Correlation. The solute solubility representation in sc-CO2 by the empirical models previously proposed was reviewed with the assessment of the model performance for solute solubility.23 The solubility of two anthraquinone dyestuffs were correlated using the representative semiempirical equations proposed by Mendez−Santiago− Teja,11 Sung−Shim,12 and Bartle et al.13 Mendez−Santiago− Teja proposed a simple linear expression on the basis of the dilute solution theory for solubility of a solid component in scCO2:

> 98

Figure 1. Flow diagram of experimental apparatus.

and 4.4 mm i.d.) was charged with about 0.1 g of anthraquinone and plugged with glass wool at both open ends of the cell. Glass beads were packed with the dye enough to make a good contact and a uniform CO2 flow distribution in the cell. A six-way valve (Rheodyne, model 7060) was used to flow sc-CO2 into the equilibrium cell after the system reached the equilibrium pressure and temperature. A flexible heater was used to keep the temperature in the flow lines from the exit of the thermostatic bath to the back pressure regulator and cold trap constant and prevent it from clogging with dry ice or deposited anthraquinone. After every experimental run, the dye remaining in the line was completely rinsed with ethanol and then removed by flowing fresh CO2. The solute dissolved into sc-CO2 was trapped in a two-step ice-cold bottle filled with ethanol. A UV−visible spectrophotometer (Shimadzu, BioSpec1600) was used to determine the anthraquinone concentration in the trap. The wavelengths of the light source were set to 559 nm for 1,4-diamino-2,3-dichloroanthraquinone (C.I. Disperse Violet 28) solution and 426 nm for 1,8-dihydroxy-4,5dinitroanthraquinone, respectively. A wet gas meter (Shinagawa, W-NK-1B) was used to measure the gas volume of CO2

T ln(y2 P) = A1 + A 2 ρ + A3T

(1)

Here y2 is the mole fraction of solute solubility, ρ is the sc-CO2 density calculated by the Span−Wagner equation of state,20 and B



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Table 2. Solubilities of 1,4-diamino-2,3-dichloroanthraquinone (C.I. Disperse Violet 28) and 1,8-dihydroxy-4,5dinitroanthraquinone in sc-CO2 and CO2 densitya T = 323.15 K

T = 353.15 K ρ

P

MPa

y2·107

mol·m−3

MPa

12.5 15.0 17.5 20.0 22.5 25.0

5.13b ± 0.2c 7.33 ± 0.02 9.59 ± 0.4 12.35 ± 0.4 12.65 ± 0.2 15.95 ± 0.2

13929.4 15899.9 17025.1 17820.9 18442.0 18954.7

15.0 17.5 20.0 22.5 25.0

2.19 3.55 4.33 5.40 5.80

P

± ± ± ± ±

0.27 0.58 0.15 0.06 0.46

y2·107

T = 383.15 K ρ

P

mol·m−3

MPa

1,4-Diamino-2,3-dichloroanthraquinone (C.I. Disperse Violet 28) 12.5 0.53 ± 0.01 7217.7 12.5 15.0 3.23 ± 0.2 9705.9 15.0 17.5 8.83 ± 0.1 11883.8 17.5 20.0 15.3 ± 0.4 13494.5 20.0 22.5 23.85 ± 3.6 14679.5 22.5 25.0 31.40 ± 1.7 15592.5 25.0 1,8-Dihydroxy-4,5-dinitroanthraquinone 15899.9 15.0 1.68 ± 0.04 9705.9 15.0 17025.1 17.5 2.91 ± 0.06 11883.8 17.5 17820.9 20.0 4.46 ± 0.21 13494.5 20.0 18442.0 22.5 7.38 ± 0.14 14679.4 22.5 18954.7 25.0 8.79 ± 0.24 15592.5 25.0

ρ y2·107

mol·m−3

1.77 ± 0.1 4.32 ± 0.3 8.46 ± 0.06 16.76 ± 0.8 31.15 ± 1.2 52.35 ± 1.8

5385.9 6887.1 8441.5 9926.1 11247.3 12376.3

2.28 ± 0.04 4.12 ± 0.74 7.29 ± 0.13 9.05 ± 0.34 11.15 ± 0.49

6887.1 8441.5 9926.1 11247.3 12376.3

a ρ (mol·m−3), CO2 density was obtained by Span−Wagner equation of state.20 Standard uncertainties u are u(T) = 0.05 K in temperature and u(p) = 0.1 MPa in pressure. bAverage values of mole fraction taken from triplicate runs. cStandard deviation of the mean estimated from triplicate runs.

Figure 2. Plot of mole fraction 107y2 against pressure P/MPa to correlate results for 1,4-diamino-2,3-dichloroanthraquinone (C.I. Disperse Violet 28) from the PRSV equation of state.

Figure 3. Plot of mole fraction 107y2 against pressure P/MPa to correlate results for 1,8-dihydroxy-4,5-dinitroanthraquinone from PRSV equation of state.

A1, A2, and A3 are the parameters of eq 1 and independent of T and P, which were obtained from the regression of experimental solubility values. Figures 6 and 7 illustrate a linear regression approximation by eq 1 to the experimental results. Sung− Shim12 expressed the solubility of the solid component in scCO2 in terms of CO2 density and temperature as follows: ln y2 = a0 +

a ⎞ a1 ⎛ + ⎜a 2 + 3 ⎟ ln ρ ⎝ T T⎠

where ρref is a reference density (700 kg/m3), Pref is a standard pressure (0.1 MPa), and b0, b1, and b2 are the parameters of eq 3. All the parameters in eqs 1 to 3 were obtained by fitting the models to the experimental solubility by an unweighted leastsquares. The following objective function was used for the minimization procedure.

(2)

1 Q= ND

where y2 is the solubility of the solute in mole fraction, ρ is the sc-CO2 density, and a0, a1, a2, and a3 are parameters of eq 2. Bartle et al. proposed a density model for the solubility of the solute as ⎛ y P⎞ b ln⎜ 2 ⎟ = b0 + b1(ρ − ρref ) + 2 T ⎝ Pref ⎠

⎛ y exp − y cal ⎞2 ∑ ⎜⎜ 2,n exp 2,n ⎟⎟ y2, n n=1 ⎝ ⎠ ND

(4)

The parameters along with the average absolute relative deviation (AARD) between the calculated and measured results are summarized in Table 3. The average absolute relative deviation (AARD) for the systems of ND data points can be calculated by

(3) C



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Figure 6. Plot of (T ln(y2P) − A3T) against density ρ/(mol·m−3) to correlate results for 1,4-diamino-2,3-dichloroanthraquinone (C.I. Disperse Violet 28) from the Mendez−Santiago−Teja model.

Figure 4. Solubilities of 1,4-diaminoanthraquinone9 and 1,4-diamino2,3-dichloroanthraquinone in sc-CO2 calculated by the regular solution model: ---, by eq 19 and , by eq 20.

Figure 7. Plot of (T ln(y2P) − A3T) against density ρ/(mol·m−3) to correlate results for 1,8-dihydroxy-4,5-dinitroanthraquinone from the Mendez−Santiago−Teja model. Figure 5. Solubilities of 1-hydroxy-4-nitroanthraquinone10 and 1,8dihydroxy-4,5-dinitroanthraquinone in sc-CO2 calculated by the regular solution model: ---, by eq 19 and , by eq 20.

AARD(%) =

100 ND

ND

∑ n=1

assumption that no sc-CO2 dissolves into solid dye, the molar volume of solid dye does not change with pressure, and the vapor pressure of solid dye is very low, the solubility of dyestuffs in sc-CO2 can be derived as

− y2,caln y2,exp n y2,exp n

y2 =

(5)

P2subl exp[v2s(P − P2subl)/RT ] ⌀SCF 2 P

(6)

sc-CO2, vs2

where y2 is the solubility of solid component in is the molar volume of solid component, Psuble is the sublimation 2 pressure of solid component, and ⌀scf 2 is the fugacity coefficient of the solid component in supercritical phase. The ⌀scf 2 can be calculated using the PRSV-EOS15 given by Stryjek and Vera with a modification of the attractive term in PR-EOS.16 The expression of PRSV-EOS is shown as

Table 3 indicates the Sung−Shim model including four parameters gave a superior result to other three-parameter models in the solubility correlation of 1,4-diamino-2,3dichloroanthraquinone and 1,8-dihydroxy-4,5-dinitroanthraquinone. 3.3. Thermodynamic Analysis. The solubility of two anthraquinone dyestuffs were analyzed by thermodynamic framework of (liquid - solid) equilibria and (gas - solid) equilibria. A detailed derivation of the thermodynamic framework has been reported elsewhere.10,24 Hence in this study, we briefly explain the calculation procedure. On the

P=

RT a − v−b v(v + b) + b(v − b)

(7)

The mixing rules of a and b in eq 7 are expressed by D



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dichloroanthraquinone were estimated by the Miller method,25 and those of 1,8-dihydroxy-4,5-dinitroanthraquinone were done by the Marrero and Gani method25 in accordance with the intended use. The molar volume of the anthraquinone was estimated by the Fedors method.26 The acentric factor of 1,4diamino-2,3-dichloroanthraquinone was done by the Edmister method,26 and that of 1,8-dihydroxy-4,5-dinitroanthraquinone was by the Poling method.24 The sublimation pressures were calculated by the method of Lee−Kesler.27 The cross parameters aij and bij were given by the van der Waals combining rules

Table 3. Calculated Results and Coefficients of eqs 1 to 3 1,4-diamino-2,3dichloroanthraquinone

parameter

eq 1, Mendez−Santiago−Teja −11511 0.18864 28.66 23.76 eq 2, Sung−Shim 39.63 −34801 −3.6187 2968.5 11.21 eq 3, Bartle et al. 18.416 0.012023 −8929.6 17.01

A1 A2 A3 AARD/% a0 a1 a2 a3 AARD/% b0 b1 b2 AARD/%

a=

−9140.9 0.13975 22.77 7.62 59.33 −38173 −6.2005 3460.9 6.55

aij = (aiiajj)1/2 (1 − kij)

11.973 0.0089291 −7142.1 8.22

bjj =

kij = αij + βij /TR

(16)

(9)

j

system

where the parameters aii and bii in eqs 8 and 9 were indicated by the critical constants and the adjustable pure parameter: aii =

(15)

Table 5. Calculated Results and Coefficients of eqs 12 and 16

∑ ∑ xixjbij i

bij =

The parameters αij and βij were obtained by minimizing the objective function of eq 4. Table 5 shows the correlated results (8)

j

0.45724R2Tc,2i ⎡ ⎢ Pc, i

⎛ 1 + κ ⎜⎜1 − ⎢⎣ ⎝

⎞⎤ T ⎟⎥ Tc, i ⎟⎠⎥⎦

1,4-diamino-2,3dichloroanthraquinone 1,8-dihydroxy-4,5dinitroanthraquinone

2

0.07780RTc, i (11)

and κ = κ0 + κ1(1 + TR0.5)(0.7 − TR )

(12)

κ0 = 0.378893 + 1.4897153ω − 0.1713184ω 2 + 0.0196554ω3

αij·10

βij·102

κ1

AARD/%

3.48

−4.54

0.100093

16.1

3.61

−3.97

0.100165

8.7

for the solubilities of 1,4-diamino-2,3-dichloroanthraquinone and 1,8-dihydroxy-4,5-dinitroanthraquinone in sc-CO2 together with the average absolute relative deviation (AARD) between the experimental and calculated values and an optimum set of the binary interaction parameter of eq 14 and adjustable parameter κ1 of PRSV-EOS. The correlation results by the PRSV-EOS with the parameters in Table 5 are illustrated in Figure 2 for 1,4-diamino-2,3-dichloroanthraquinone and in Figure 3 for 1,8-dihydroxy-4,5-dinitroanthraquinone. Figures 2 and 3 show good agreement between the experimental and calculated values. Moreover, the solubility of two anthraquinone dyestuffs correlated by the thermodynamic criteria of solid−liquid equilibria, assuming there was no considerable solubility of the sc-CO2 in the solid phase.9,10,14 We used the regular solution model combined with the Flory−Huggins equation:

(10)

Pc, i

(14)

1 (bii + bjj) 2 where the binary interaction parameter kij was given by

∑ ∑ xixjaij i

b=

1,8-dihydroxy-4,5dinitroanthrquinone

(13)

The reduced temperature, TR in eq 12 is expressed by T/Tc. Table 4 summarized the critical properties Tc and Pc, acentric factor ω, molar volume, and sublimation pressure of the solid components. The critical properties of 1,4-diamino-2,3-

Table 4. Physical Properties for 1,4-Diamino-2,3-dichloroanthraquinone (C.I. Disperse Violet 28) and 1,8-Dihydroxy-4,5dinitroanthraquinone Tm/K −1 b Δhm 2 /(kJ·mol ) vs2/(m3·mol−1)c Tc/K Pc/MPa ω Psubl (at T = 323.15 K)/Pah 2 subl P2 (at T = 353.15 K)/Pah Psubl (at T = 383.15 K)/Pah 2

1,4-diamino-2,3-dichloroanthraquinone

1,8-dihydroxy-4,5-dinitroanthrquinone

576a 29.82 1.758·10−4 919.7d 2.402d 1.091f 5.675·10−6 3.760·10−4 1.162·10−2

573.1b 30.77 1.254·10−4 1045.5e 3.15e 0.733g 7.791·10−6 3.648·10−4 8.687·10−3

a Observed by Goi et al.29 bEstimated by Jain et al., method.30 cEstimated by Fedors method.27 dEstimated by Miller method.25 eEstimated by Gani group contribution method.26 fEstimated by Edmister method.27 gEstimated by Poling et al. method.24 hEstimated by Lee−Kesler method.27

E



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Table 6. Calculated Results and Coefficients of eqs 19 and 20 system

a/Pa

b/(Pa·m3·mol−1)

1,4-diamino-2,3-dichloroanthraquinone

15993 17947 19272 18565

0.55732 0.004193 0.5200 1.4701

1,8-dihydroxy-4,5-dinitroanthraquinone

ln y2 =

⎞ v Δh2m ⎛ T − 1⎟ − 2 (δ1 − δ2)2 ⎜ RT ⎝ Tm ⎠ RT ⎛v ⎞ v − ln⎜ 2 ⎟ − 1 + 2 v1 ⎝ v1 ⎠

(17)

where Tm and are the melting temperature and melting enthalpy of anthraquinone, respectively. The v1 and v2 are the molar volume of sc-CO2 and the solid component. The solubility parameter of sc-CO2 was calculated by the method of Giddings et al.28

■

(19)

c δ2 = a + bρCO

(20)

AUTHOR INFORMATION

Funding

This work was partially supported by the Japan Society for the Promotion Science, Grant-in-Aid for Scientific Research (C) No. 23560905. Notes

The authors declare no competing financial interest.

■

or 2

0.90117

26.2 11.2 14.5 14.8

*E-mail: [email protected]. Tel.: +81 76 234 4804. Fax: +81 76 234 4829.

The ρR (=ρ/ρc) is the reduced CO2 density, ρc is the critical density, and ρ is the sc-CO2 density calculated by the Span− Wagner equation of state.20 Pc is the critical pressure of CO2. The solute solubility parameter was assumed to be dependent on CO2 density and can be expressed in the present work as 2

1.478

Corresponding Author

(18)

δ2 = a + bρCO

AARD/%

correlated successfully with the Mendez−Santiago−Teja, Sung−Shim, and Bartle et al. equations, expressed in terms of CO2 density. Moreover, the solubilities of the anthraquinone derivatives in sc-CO2 were calculated satisfactorily using the Peng−Robinson equation of state modified by Stryjek−Vera with the van der Waals one fluid mixing rule and the regular solution model with the Flory−Huggins theory. Finally satisfactory agreement was obtained between the experimental and calculated solubility of the anthraquinone dyestuffs in scCO2.

Δhm 2

⎛ ρ ⎞ δ1/MPa 0.5 = 8.0325(Pc/MPa)0.5 ⎜ R ⎟ ⎝ 2.66 ⎠

c

ACKNOWLEDGMENTS The authors would like to thank Mr. Tatsuro Tanaka and Mr. Keisuke Shimizu for the experimental work.

Table 6 summarized the parameters of eqs 19 and 20 and average absolute relative deviation (AARD) between the experimental and calculated results. Figures 4 and 5 illustrated the solubility correlation against density ρ for anthraquinone derivatives calculated from the regular solution model with the Flory−Huggins, and accurate solubility representation was obtained by the regular solution model with eq 20 coupled with the Flory−Huggins theory. As a whole the correlation results obtained from both the empirical equations and the thermodynamically based models showed that the deviation of the 1,4-diamino-2,3-dichloroanthraquinone system was larger than that of the 1,8-dihydroxy-4,5-dinitroanthraquinone system. It might be explained by the fact that the purity of 1,4diamino-2,3-dichloroanthraquinone was lower than that of 1,8dihydroxy-4,5-dinitroanthraquinone.

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REFERENCES

(1) Bach, E.; Cleve, E.; Schollmeyer, E. Past, present and future of supercritical fluid dyeing technology:an overview. Rev. Prog. Color. Relat. Top. 2002, 32, 88−102. (2) Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Solubility relationships for disperse dyes in supercritical carbon dioxide. Dyes Pigm. 2000, 45, 177−183. (3) Lin, H.-M.; Liu, C.-Y.; Cheng, C.-H.; Chen, Y.-T.; Lee, M.-J. Solubilities of disperse dyes of blue 79, red 153, and yellow 119 in supercritical carbon dioxide. J. Supercrit. Fluids 2001, 21, 1−9. (4) Mishima, K.; Matsuyama, K.; Ishikawa, H.; Hayashi, K.; Maeda, S. Measurement and correlation of solubilities of azo dyes and anthraquinone in supercritical carbon dioxide. Fluid Phase Equilib. 2002, 194−197, 895−904. (5) Tsai, C.-C.; Lin, H.-M.; Lee, M.-J. Solubility of C.I. Disperse Violet 1 in Supercritical Car- bon Dioxide with or without Cosolvent. J. Chem. Eng. Data 2008, 53, 2163−2169. (6) Coelho, J. P.; Stateva, R. P. Solubility of Red 153 and Blue1 in Supercritical Carbon Dioxide. J. Chem. Eng. Data 2011, 56, 4686− 4690. (7) Shamsipur, M.; Karami, A. R.; Yamini, Y.; Sharghi, H. Solubilities of some 1-hydroxy-9,10-anthraquinone derivatives in supercritical carbon dioxide. J. Supercrit. Fluids 2004, 32, 47−53. (8) Coelho, J. P.; Mendonca, A. F.; Palavra, A. F.; Stateva, R. P. On the Solubility of Three Disperse Anthraquinone Dyes in Supercritical Carbon Dioxide: New Experimental Data and Correlation. Ind. Eng. Chem. Res. 2011, 50, 4618−4624. (9) Alwi, R. S.; Tanaka, T.; Tamura, K. Measurement and correlation of solubility of anthraquinone dyestuffs in supercritical carbon dioxide. J. Chem. Thermodyn. 2014, 74, 119−125.

4. CONCLUSION Over the pressure ranges of 12.5 MPa to 25.0 MPa and at the temperatures of (323.15, 353.15, and 383.15) K the solubilities of 1,4-diamino-2,3-dichloroanthraquinone and 1,8-dihydroxy4,5-dinitroanthraquinone in supercritical carbon dioxide were measured by a flow setup system. The solubility of 1,4-diamino2,3-dichloroanthraquinone in sc-CO2 was higher than that of 1,8-dihydroxy-4,5-dinitroanthraquinone under the system temperature and pressure conditions examined. It was found that the 2,3-dichloro group addition onto 1,4-diaminoanthraquinone leads to higher solubility of 1,4-diaminoanthraquinone and the addition of the 8-hydroxy-5-nitro group on 1-hydroxy4-nitroanthraquinone causes lower solubility than that of 1hydroxy-4-nitroanthraquinone. The experimental results were F



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(10) Tamura, K.; Alwi, R. S. Solubility of anthraquinone derivatives in supercritical carbon dioxide. Dyes Pigm. 2015, 113, 351−356. (11) Mendez-Santiago, J.; Teja, A. S. Solubility of solids in supercritical fluids. Fluid Phase Equilib. 1999, 158−160, 501−510. (12) Sung, H.-D.; Shim, J.-J. Solubility of C.I. disperse red 60 and C.I. disperse blue 60 in supercritical carbon dioxide. J. Chem. Eng. Data 1999, 44, 985−989. (13) Bartle, K. D.; Clifford, A. A.; Jafar, S. A.; Shilstone, G. F. Solubilities of solids and liquids of low volatility in supercritical carbon dioxide. J. Phys. Chem. Ref. Data 1991, 20, 713−756. (14) Iwai, Y.; Koga, Y.; Fukuda, T.; Arai, Y. Correlation of solubilities of high boiling components in supercritical carbon dioxide using a solution model. J. Chem. Eng. Jpn. 1992, 25, 757−760. (15) Stryjek, R.; Vera, J. H. PRSV: An improved PengRobinson equation of state for pure compounds and mixtures. Can. J. Chem. Eng. 1986, 64, 323−333. (16) Peng, D.-Y.; Robinson, D. B. A New Two-Constant Equation of State. Ind. Eng. Chem. Fundam. 1976, 15, 59−64. (17) Shinoda, T.; Tamura, K. Solubilities of C.I. Disperse Red 1 and C.I. Disperse Red 13 in supercritical carbon dioxide. Fluid Phase Equilib. 2003, 213, 115−123. (18) Shinoda, T.; Tamura, K. Solubilities of C.I. disperse orange 25 and C.I. disperse blue 354 in supercritical carbon dioxide. J. Chem. Eng. Data 2003, 48, 869−873. (19) Tamura, K.; Shinoda, T. Binary and ternary solubilities of disperse dyes and their blend in supercritical carbon dioxide. Fluid Phase Equilib. 2004, 219, 25−32. (20) Span, R.; Wagner, W. A New Equation of State for Carbon Dioxide Covering the Fluid Region from the Triple Point Temperature to 1100 K at Pressures up to 800 MPa. J. Phys. Chem. Ref. Data 1996, 25, 1509−1596. (21) Foster, N. R.; Gurdial, G. S.; Yun, J. S. L.; Liong, K. K.; Tilly, K. D.; Ting, S. S. T.; Singh, H.; Lee, J. H. Significance of the crossover pressure in solid-supercritical fluid phase equilibria. Ind. Eng. Chem. Res. 1991, 30, 1955−1964. (22) Torrisi, A.; Mellot-Draznieks, C.; Bell, R. G. Impact of ligands on CO2 adsorption in metal-organic frameworks: First principles study of the interaction of CO2 with functionalized benzenes. II. Effect of polar and acidic substituents. J. Chem. Phys. 2010, 132, 044705−1−13. (23) Khansary, M. A.; Amiri, F.; Hosseini, A.; Sani, A.; Shahbeig, H. Representing solute solubility in supercritical carbon dioxide: A novel empirical model. Chem. Eng. Res. Des. 2015, 93, 355−365. (24) Poling, B. E.; Prausnitz, J. M.; O’Connell, J. P. The Properties of Gases and Liquids, 5th ed.; McGraw-Hill: New York, 2001. (25) Lyman, W. J.; Reehl, W. F.; Rosenblatt, D. H.; Rosenblatt, D. H. Handbook of Chemical Property Estimation Methods: Environmental Behavior of Organic Compounds; McGrawHill: New York, 1982. (26) Marrero, J.; Gani, R. Group-contribution based estimation of pure component properties. Fluid Phase Equilib. 2001, 183−184, 183− 208. (27) Fedors, R. F. Method for estimating both the solubility parameters and molar volumes of liquids. Polym. Eng. Sci. 1974, 14, 147−154. (28) Giddings, J. C.; Myers, M. N.; McLaren, L.; Keller, R. A. High Pressure Gas Chromatography of Nonvolatile Species. Science 1968, 162, 67−73. (29) Goi, K.; Konishi, M. Preparation of some acid anthraquinone dyes from tetrachlorophthalic anhydride, 1960. Osaka-furitsu Kogyo Shoreikan Hokoku 1960, 24, 51−56. (30) Jain, A.; Yang, G.; Yalkowsky, S. H. Estimation of Melting Points of Organic Compounds. Ind. Eng. Chem. Res. 2004, 43, 7618−7621.

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Measurement and Correlation of Derivatized Anthraquinone Solubility

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