Equilibrium Solubility of Biapenem in Different Neat and Binary Solvents

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Equilibrium Solubility of Biapenem in Different Neat and Binary Solvents: Experimental Determination and Model Correlation Renjie Xu,* Chunjuan Huang, and Jie Xu

J. Chem. Eng. Data Downloaded from pubs.acs.org by UNIV OF TEXAS AT DALLAS on 03/15/19. For personal use only.

Guangling College, Yangzhou University, YangZhou, Jiangsu 225009, People’s Republic of China ABSTRACT: The equilibrium solubility is the basis of purification and further theoretical studies of biapenem. In this work, the solubility of biapenem in 10 pure solvents (methanol, ethanol n-propanol, isopropanol, acetone, N,N-dimethylformamide (DMF), acetonitrile, dimethyl sulfoxide (DMSO), N-methyl pyrrolidone (NMP), and ethyl acetate) and solvent mixtures (ethyl acetate + methanol) was measured by using a static equilibrium method at temperatures from 283.15 to 323.15 K, at p = 101.2 kPa. To sum up, the solubility was highest in NMP and lowest in acetone. The solubility from high to low is NMP (0.9663 × 10−4, 298.15 K) > DMSO (0.8655 × 10−4, 298.15 K) > DMF (0.7796 × 10−4, 298.15 K) > ethyl acetate (0.7161 × 10−4, 298.15 K) > acetonitrile (0.5169 × 10−4, 298.15 K) > methanol (0.3068 × 10−4, 298.15 K) > ethanol (0.2455 × 10−4, 298.15 K) > npropanol (0.1966 × 10−4, 298.15 K) > isopropanol (0.1205 × 10−4, 298.15 K) > acetone (0.04576 × 10−4, 298.15 K). The experiment values in monosolvents were associated with the modified Apelblat equation. The experiment values in mixed solvents were associated with the Jouyban− Acree model, Apelblat−Jouyban−Acree model, and CNIBS/R-K model. From the correlation results, the largest RAD values of the above three models are 0.83%, 0.98%, and 0.60%, respectively. These models can all fit the experiment values very well. Accordingly, in values of solubility in the pure solvent correlation process, the maximum values of root-mean-square deviation (RMSD) and relative average deviation (RAD) are 0.42 × 10−6 and 0.80%, respectively. Furthermore, solute−solvent interactions have been studied in monosolvents. The hydrogen bonds play an important role in the dissolution process of biapenem. Especially, the experimental values have influences on purification, recrystallization, and formulation development of biapenem in production.

1. INTRODUCTION Biapenem (CAS Registry No. 120410-24-4, shown in Figure 1) is a parenteral carbapenem antibiotic with a broad spectrum

the preparation of biapenem have been extensively investigated in China.8−11 However, there is a lack of a stable and high yield method for the purification of the crude biapenem. The application and synthesis of biapenem have been a main focus, but no attention has been paid to establishing a solid−liquid equilibrium phase diagram for purification and preparation of pharmaceutical preparations. In the previous publications, biapenem obtained from the known process was purified by recrystallization in methanol and ethanol and washed with ethyl acetate or solvent mixtures. In addition, DMF, NMP, DMSO, C1−C4 alcohols, acetonitrile, and acetone were selected as solvent priorities during the preparation process of biapenem.8,10 Furthermore, methanol, ethanol, and propanol were safe and widely used solvents in the chemical and pharmaceutical industries. On the basis of the considerations mentioned above, in order to provide fundamental solubility data for purification, the crude products and preparation of pharmaceutical preparations are given. The solubility of biapenem in these 10 organic solvents and (ethyl acetate + methanol) mixture solution were admeasured via a static equilibrium method at a temperature range from 283.15 to 323.15 K, nine solvents (isopropanol, acetonitrile, methanol,

Figure 1. Chemical structure of biapenem.

against Gram-positive, Gram-negative, and anaerobic bacteria including β-lactamase-producing strains and P. aeruginosa.1−4 It has a strong postantibiotic effect, and it is highly active against pseudomonas biofilm-forming strains as well as several efflux system mutants.5 In March 2002, biapenem was released as the fourth carbapenem antibiotic.6 It is often used in critically ill patients with severe infections because of its potent antibacterial activity, almost no renal toxicity, no central neurotoxicity, and minimal side effects.7 A lot of methods for © XXXX American Chemical Society

Received: November 8, 2018 Accepted: March 8, 2019

A

DOI: 10.1021/acs.jced.8b01051 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 1. Source and Purity of the Materials Used in the Work chemicals

molar mass g·mol−1

CAS registry number

source

mass fraction purity

analytical method

biapenem methanol n-propanol isopropanol acetone ethyl acetate acetonitrile ethanol DMF NMP DMSO

350.39 32.04 60.10 60.10 58.08 88.11 41.05 46.07 73.09 99.13 78.13

120410−24−4 67−56−1 71−23−8 67−63−0 67−64−1 141−78−6 75−05−8 64−17−5 68−12−2 872−50−4 67−68−5

Sinopharm Chemical Reagent Co.

0.995 0.997 0.995 0.995 0.995 0.995 0.994 0.995 0.996 0.994 0.996

HPLCa GCb GCb GCb GCb GCb GCb GCb GCb GCb GCb

a

High-performance liquid phase chromatograph. bGas chromatography.

acetone, NMP, ethanol, DMF, ethyl acetate, n-propanol, and DMSO) and binary solvent mixtures (ethyl acetate + methanol) were included. Solute−solvent interactions were also discussed. The solubility data were correlated via thermodynamic models. These models can all fit the experiment values very well and can help to illuminate the relationship among solubility, temperature, and solvent composition.

In this work, experiment solubility values in pure solvents were correlated via modified Apelblat model,12,13 and values in mixed solvents were correlated via the Jouyban−Acree model,14,15 a combination of the Jouyban−Acree model with modified Apelblat model,16,17 and the CNIBS/R-K model.18 The modified Apelblat model is a semiempirical model and can be used to correlate the solubility values in monosolvents.12,13 The model is described in eq 1.

n

ln(x) = wA ln(xA ) + wB ln(x B) + wAwB∑ Ai (wA − wB)i i=0

(4)

When n = 2, the model can be simplified to

(1)

ln(x) = B0 + B1x 2 + B2 x 22 + B3x 23 + B4 x 24

x is the solubility of biapenem as a mole fraction. The A and B parameters promulgate the influence of solution nonideality upon the solute solubility and the variation of solute activity coefficient, respectively. The parameter C promulgates the influence of temperature upon the fusion enthalpy of a solute. The Jouyban−Acree model can associate the solubility values in solvent mixtures.14,15 The model can expressed as the following equation.

20

(5)

where x is the biapenem solubility in mole fraction, and x2 is the initial mole fraction composition of ethyl acetate in a solvent in the absence of biapenem. B0, B1, B2, B3, and B4 are the parameters of this model, which can be regressed from fitting the experimental solubility data.

3. EXPERIMENTAL SECTION 3.1. Materials. Biapenem and the isopropanol, ethyl acetate, n-propanol, NMP, methanol, acetonitrile, ethanol, acetone, DMF, and DMSO were provided by Sinopharm Chemical Reagent Co., Ltd., China; biapenem was 0.995 in mass fraction, which was tested via HPLC. The solvents were analytical grade, and the mass fractions of these were all greater than 0.994, which were determined by gas chromatography (GC). Detailed information on biapenem and used solvents is listed in Table 1. 3.2. Powder X-ray Diffraction. A Bruker AXS D8 Advance (Bruker, Germany) was used to measure the PXRD experiment. Cu Kα radiation (λ = 1.54184 nm) was used to determine the biapenem sample. The test conditions are as follows: scanning rate is 5°·min−1; the diffraction angle (2θ) range is 5°−80°. This conditions were used to confirm the form of biapenem before and after the experiments.

2

ln x12 = w1 ln x1,T + w2 ln x 2,T +

(3)

where A1, B1, C1, A2, B2, and C2 are regressions from solubility data in pure solvent (ethyl acetate and methanol) and Ji is the Apelblat−Jouyban−Acree model constants. The CNIBS/R-K model is deemed one of the most appropriate models for binary solvent systems and was proposed by Acree.18,19 This model is expressed as eq 4

2. CORRELATION MODELS

ln x = A + B /(T /K ) + C ln(T /K )

ÄÅ ÉÑ ÅÅ ÑÑ B1 Å ln x12 = w1ÅÅA1 + + C1 ln(T /K )ÑÑÑ ÅÅÇ ÑÑÖ T /K ÅÄÅ ÑÉÑ B2 Å Ñ + w2ÅÅÅA 2 + + C2 ln(T /K )ÑÑÑ ÅÅÇ ÑÑÖ T /K 2 ww + 1 2 ∑ Ji (w1 − w2)i T /K i = 0

w1w2 ∑ J (w1 − w2)i T /K i = 0 i (2)

where x12 is the solubility (x) of iohexol in a binary system at absolute temperature; w1 and w2 stand for the mass fractions of ethyl acetate and methanol in (ethyl acetate + methanol) mixtures free of the biapenem, respectively; x1,T and x2,T are the mole fraction solubility values of biapenem in a monosolvent; and Ji is the parameters of the Jouyban−Acree model. In the Apelblat−Jouyban−Acree model, eq 1 is substituted into eq 2. The model expressed as eq 3.16,17 B

DOI: 10.1021/acs.jced.8b01051 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Figure 2. PXRD spectrum of biapenem. (a) Raw material and crystallized in monosolvents; (b) raw material and crystallized in different compositions of (ethyl acetate + methanol).

Table 2. Experimental Solubility (x) of Biapenem in Mole Fraction in Monosolvents at the Temperature Ranging from 283.15 to 323.15 K under 101.2 kPaa solvents T/K

4

10 x

exp

4

apelblat

10 x

methanol 283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15 100RAD 283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15 100RAD

0.1863 0.2193 0.2589 0.3068 0.3568 0.4182 0.4903 0.5634 0.6607

0.1862 0.2201 0.2594 0.3050 0.3576 0.4181 0.4878 0.5676 0.6590 0.33 acetone 0.01768 0.01794 0.02509 0.02472 0.03402 0.03372 0.04572 0.04553 0.05971 0.06091 0.08128 0.08074 0.1061 0.1061 0.1386 0.1384 0.1788 0.1790 0.80

4

10 x

exp

4

10 x

apelblat

104 xexp

n-propanol

acetonitrile 0.3625 0.4071 0.4606 0.5169 0.5821 0.6667 0.7462 0.8497 0.9557

0.3616 0.4074 0.4595 0.5187 0.5858 0.6620 0.7484 0.8464 0.9575 0.35 ethyl acetate 0.5208 0.5184 0.5728 0.5775 0.6475 0.6434 0.7161 0.7170 0.7970 0.7991 0.8900 0.8905 0.9931 0.9924 1.109 1.106 1.230 1.232 0.32

104 xapelblat

0.1167 0.1373 0.1624 0.1966 0.2316 0.2699 0.3190 0.3709 0.4321

0.7859 0.8655 0.9473 1.040 1.161 1.287 1.420

0.1154 0.1381 0.1645 0.1952 0.2306 0.2713 0.3180 0.3713 0.4321 0.57 DMSO

0.7859 0.8625 0.9490 1.047 1.157 1.282 1.423 0.30

104 xexp

104 xapelblat

104 xexp

isopropanol 0.06658 0.08242 0.09983 0.1205 0.1413 0.1692 0.2002 0.2371 0.2795

ethanol

0.06780 0.08216 0.09909 0.1190 0.1422 0.1693 0.2008 0.2372 0.2792 0.59

0.1486 0.1765 0.2090 0.2455 0.2904 0.3410 0.3975 0.4543 0.5227

0.5801 0.6416 0.7100 0.7862 0.8709 0.9651 1.070 1.186 1.315 0.22

0.7583 0.8138 0.8786 0.9663 1.059 1.168 1.282 1.410 1.556

DMF 0.5801 0.6440 0.7107 0.7796 0.8722 0.9651 1.072 1.188 1.313

104 xapelblat 0.1471 0.1763 0.2098 0.2479 0.2912 0.3400 0.3946 0.4555 0.5231 0.47 NMP 0.7522 0.8154 0.8870 0.9679 1.059 1.163 1.279 1.410 1.558 0.34

a

x represents the experimental data of biapenem at the research temperature T; RAD denotes the relative average deviation. Standard uncertainties u are u(T) = 0.02 K, u(p) = 400 Pa. Relative standard uncertainty ur is ur(x) = 0.026. xexp, experiment data; xapelblat, calculated by apelblat model.

3.3. Solubility Determination. In this experiment, a static equilibrium method was used to determine the solute solubility at the temperature range from 283.15 to 323.15 K.21,22 The equilibrium liquids are tested by HPLC. The reliability of verification of the experimental apparatus was verified in our previous work.23 The mixed solvents were prepared by analytical balance (CPA225D). The mass fraction of ethyl acetate in the ethyl acetate + methanol system varied from 0 to 1. Excessive solid sample and about 40 mL of solvents were added into the glass vessel. The experimental temperature was kept using a thermostatic water-circulator bath with circulating water. The actual temperature was shown with a mercury glass microthermometer; the standard uncertainty was 0.02 K. A magnetic stirrer was used to blend the solvent and solute adequately. The equilibrium liquid phase was taken out using a 2 mL

preheated syringe every 2 h; for convenience, a pore syringe filter (PTFE 0.2 μm) was connected to the preheated syringe. The sample was analyzed via HPLC. For all the systems, 13 h allowed the solution to reach equilibrium. When the equilibrium reached a balance, the magnetic stirrer was stopped, and the solid was allowed to precipitate. When the equilibrium liquid phase was clear, it was taken out with a 2 mL preheated syringe and then transferred instantaneously to a 25 mL flask covered with a rubber stopper and weighed again. The sample was diluted to the mark, and then 1 μL was taken out for analysis via HPLC. The relative standard uncertainty in mole fraction solubility was 0.026. 3.4. Analysis Method. The sample was analyzed by HPLC. A reverse phase column was installed on the machine. The type of phase column was an LP-C18 (250 mm × 4.6 mm). The temperature of the phase column box was set at 303 C

DOI: 10.1021/acs.jced.8b01051 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Figure 3. Solubility (x) of biapenem in mole fractions in monosolvents at different temperatures: (a) ■, methanol; ○, ethanol; ▲, n-ropanol; ▼, isopropanol; ◀, acetone. (b) ★, NMP; ◆, DMSO; □, DMF, ▶, ethyl acetate; ●, acetonitrile. Calculated curves by modified Apelblat equation.

Table 3. Solvatochromic Parameters α and β for the Selected Solventsa

K. The UV wavelength was 290 nm, which was determined by continuous UV scanning. Pure methanol was used as the mobile phase; the flow rate was 1.0 mL·min−1. Each analysis was carried out three times; the final result of the analysis was the average value of three measurements. The GC analysis was carried out with a Beijing Fuli gas chromatograph with a flame photometric detector. A fused-silica capillary column of crosslinked HP-5 was used. The operation conditions were as follows: column temperature, 100 °C; injection and detector temperature, 250 °C; nitrogen flow rate, 40 mL·mL−1; hydrogen flow rate, 40 mL·mL−1; atmosphere flow rate, 450 mL·mL−1.

4. RESULTS AND DISCUSSION 4.1. Powder X-ray Diffraction Analysis. Figure 2 shows the PXRD patterns of biapenem raw material and that recrystallized in different solvents. Patterns of the recrystallized sample and raw material have the same peaks; therefore, there is no phase transformation during the experimental process. 4.2. Solubility Data. 4.2.1. Solubility Values in Monosolvents. The experimental solubility (x) of biapenem in mole fraction in isopropanol, ethyl acetate, methanol, NMP, ethanol, n-propanol, acetone, DMF, acetonitrile, and DMSO at temperatures from (283.15 to 323.15) K are listed in Table 2, and the data points are shown graphically in Figure 3. From Figure 3, for a certain solvent, the solubility of biapenem increases with increasing temperature. At a certain temperature, the experimental solubility of biapenem in mole fraction is largest in NMP (0.9663 × 10−4, 298.15 K) and lowest in acetone (0.04576 × 10−4, 298.15 K). Figure 3 further show the solubility from high to low is NMP (0.9663 × 10−4, 298.15K) > DMSO (0.8655 × 10−4, 298.15K) > DMF (0.7796 × 10−4, 298.15K) > ethyl acetate (0.7161 × 10−4, 298.15K) > acetonitrile (0.5169 × 10−4, 298.15K) > methanol (0.3068 × 10−4, 298.15K) > ethanol (0.2455 × 10−4, 298.15K) > npropanol (0.1966 × 10−4, 298.15K) > isopropanol (0.1205 × 10−4, 298.15K) > acetone (0.04576 × 10−4, 298.15K). Table 3 presents some properties of the studied solvents, which correspond to polarities and dielectric constants (ε).24 It can be found in Figure 3 and Tables 2 and 3 that, for polar protic solvents (methanol, ethanol, n-propanol, and isopropanol), the order of the experimental solubility values in mole fraction are according to the polarities and dielectric constants (ε). The solubility data in alcohol are ranked methanol > ethanol > n-propanol > isopropanol. And for other aprotic solvents (NMP, DMSO, ethyl acetate, acetonitrile, DMF, and

a

solvent

polarity (water 100)

ε(293 K) F·m−1

α

β

methanol n-propanol isopropanol acetone acetonitrile ethyl acetate ethanol DMF NMP DMSO

76.2 61.7 54.6 35.5 46 23 65.4 40.4 36 44.4

32.6 20.1 18.3 20.6 37.5 6.02 22.4 36.7 32.2 46.6

0.98 0.84 0.76 0.08 0.19 0 0.86 0 0 0

0.66 0.90 0.84 0.43 0.40 0.45 0.75 0.69 0.77 0.76

Taken from refs 24−26.

acetone), the order of them from high to low is in accordance with the polarities and dielectric constants (ε) except for NMP, ethyl acetate, and acetate. It is seen that polarities and dielectric constants are a significant factor affecting the solubility behavior, but the polarities and dielectric constants are not the only factors to affect the solubility of biapenem. From the biapenem structure, it is shown that the molecule has one hydrogen bonding donor (HBD) and six hydrogen bonding acceptors (HBA), which suggests that solute and solvent molecules can form a hydrogen bond. Thus, in this system, it can be expected that hydrogen bonds may have an effect on the solubility of biapenem in solvents. The solvents’ polarities, hydrogen bond acceptor properties (β), and hydrogen bond donor properties (α) are shown in Table 3.25,26 α is the solvents’ hydrogen bond donation (HBD) ability; β is the solvents’ hydrogen bond acceptance (HBA) or electron pair donation ability to form a coordinative bond. The larger values of α or β will increase the hydrogen bond donation or hydrogen bond acceptance ability of the solvent. That is to say, solvents and solutes are more likely to form hydrogen bonds. From Figure 3 and Table 2, from biapenem + alcohol systems, the order of the solubility in mole fraction from high to low is according to the hydrogen bond donor of alcohol solvents. The order of hydrogen bond donor properties of alcohol is methanol > ethanol > n-propanol > isopropanol. For biapenem, the hydrogen bonding donor’s ability is weaker than the hydrogen bonding acceptor’s ability. Accordingly, HBD interaction of the solvent with the solute plays a main role in biapenem−alcohol interactions. In addition, the steric effect and van der Waals force will be considered as important D

DOI: 10.1021/acs.jced.8b01051 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 4. Experimental Solubility Data (xeT,W × 104) of Biapenem in Mixed Solvent of Ethyl Acetate (w) + Methanol (1 − w) with Various Mass Fractions at T/K = (283.15 to 323.15) under p = 101.1 kPaa w T/K

1

0.90

0.80

0.70

0.60

0.50

0.40

0.30

0.20

0.10

0

283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15

0.5208 0.5728 0.6475 0.7161 0.7970 0.8900 0.9931 1.109 1.230

0.4819 0.5338 0.5992 0.6702 0.7447 0.8384 0.9352 1.044 1.171

0.4450 0.4920 0.5557 0.6250 0.6974 0.7907 0.8822 0.9863 1.107

0.4109 0.4547 0.5153 0.5818 0.6549 0.7416 0.8349 0.9359 1.055

0.3722 0.4133 0.4673 0.5313 0.6058 0.6862 0.7771 0.8715 0.9853

0.3399 0.3771 0.4321 0.4885 0.5627 0.6361 0.7235 0.8144 0.9265

0.3037 0.3409 0.3914 0.4478 0.5129 0.5863 0.6692 0.7555 0.8676

0.2661 0.3057 0.3493 0.3987 0.4607 0.5279 0.6383 0.6876 0.8129

0.2393 0.2695 0.3131 0.3670 0.4199 0.4871 0.5675 0.6424 0.7531

0.2121 0.2469 0.2904 0.3353 0.3928 0.4554 0.5268 0.6017 0.7033

0.1863 0.2193 0.2589 0.3068 0.3568 0.4182 0.4903 0.5634 0.6607

a

Standard uncertainties u are u(T) = 0.02 K, u(p) = 400 Pa. Relative standard uncertainty ur is ur(x) = 0.026. The relative standard uncertainty of solvent prepared by mixing different masses of the solvents is ur(w) = 0.03. w stands for the ethyl acetate in mass fraction in ethyl acetate (w) + methanol (1 − w) system.

effects. Biapenem’s molecular size is comparatively large, when the biapenem interacts with alcohols with longer carbon chains. The longer the carbon chain is, the lower the solubility of biapenem. So the lowest solubility of biapenem is in isopropanol among alcohols. For the remaining solvents, the sequence of them, high to low, is also according to HBA expect for acetonitrile. The HBA properties of the remaining solvents are ranked as NMP > DMSO > DMF > ethyl acetate > acetone > acetonitrile. From the data shown in Table 4, the HBD capacities are almost small or even zero in nonalcohol solvents. Accordingly, in interactions of biapenem−nonalcohol, HBA interaction plays a leading role. However, from HBA and HBD properties of acetonitrile and acetone solvents, there is both HBD interaction and HBA interaction of the solute with the solvent, and the value of α of acetonitrile is greater than that of acetone, so the solubility in acetonitrile is slightly larger than in acetone. For the most part, based on a single reason, it is very difficult to illustrate the solubility behavior of biapenem. The solubility behavior may be cause by lots of factors, e.g., the rule of “like dissolves like,” solute−solvent interactions, polarities, molecular shapes and sizes, and solvent−solvent interactions. 4.2.2. Solubility Values in Solvents Mixtures. The biapenem mole fraction solubility (x) in (ethyl acetate + methanol) is shown in Table 4. What’s more, the relationship of solubility, solvent composition, and temperature is plotted in Figure 4. The solubility (x) of biapenem increases with increasing mass fraction of ethyl acetate and the temperature. From Table 4 and Figure 4, the solubility (x) of biapenem is a function of solvent composition and temperature. It is obvious that the maximum solubility of biapenem is observed in neat ethyl acetate and is lowest in neat methanol. 4.3. Solubility Correlation. The experimental values of solubility were correlated by the nonlinear regression method.27 The objective function is defined as F=

∑ (ln xie − ln xic)2 i=1

Figure 4. Solubility (x) of biapenem in mole fraction in solvent mixtures (ethyl acetate (w) + methanol (1 − w)) at different temperatures: experimental and calculated solubility data of biapenem in ethyl acetate (w) + methanol (1 − w) mixed solutions with various mass fractions at different temperatures. Calculated surface via the Jouyban−Acree model in solvent mixtures.

RAD =

N i |x c − x e| y 1 ∑ jjjjj i e i zzzzz N i = 1 k xi {

(7)

N

RMSD =

∑i = 1 (xic − xie)2 N

(8)

Here, N stands for the experimental data points’ numbers, xie and xic, and represent the experimental data and correlated data, separately. Table 5 lists the RMSD values and the values of parameters A, B, and C regressed by the modified Apelblat equation. From parameters in Table 5, parameters A, B, and C obtained in the solvent of NMP have the greatest values, indicating that the solution nonideality and solute activity coefficients have the greatest influence upon the solute solubility, and temperature has the greatest influence upon the fusion enthalpy of a solute in NMP. And, the greatest values obtained in ethanol solvent indicate that they have a minimum impact. Ji values regressed by the Jouyban−Acree model and modified Apelblat− Jouyban−Acree model along with the calculated values of RMSD and RAD are listed in Table 6, and calculated values of RMSD and RAD and Bi regressed by the CNIBS/R-K model are listed in Table 7. In order to compare experimental

(6)

Here, ln xie and ln xic are the logarithms of experimental data and correlated data with models, respectively. Furthermore, The RAD values and RMSD values calculated by the following two equations are used for evaluating these four models in this work. E

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5. CONCLUSIONS In this research, the phase behaviors and solubility values of biapenem in 10 pure solvents and the (ethyl acetate + methanol) system were measured via the static equilibrium method. The experimental atmospheric pressure was about 101.2 kPa, and the temperature ranged from (283.15 to 323.15 K). The solubility (x) of biapenem in studied pure solvents increased with increasing temperature. The order of them is NMP > DMSO > DMF > ethyl acetate > acetonitrile > methanol > ethanol > n-propanol > isopropanol > acetone. The hydrogen bonds play an important role in the dissolution process of biapenem. The solute−solvent intermolecular interactions on the solubility in those monosolvents were discussed. The experimental solubility (x) of biapenem in pure solvents was correlated by modified Apelblat model. The maximum values of RMSD and RAD were 0.42 × 10−6 and 0.80%, separately. Furthermore, the experimental solubility data in the (ethyl acetate + methanol) system was correlated by the Apelblat−Jouyban−Acree model, Jouyban−Acree model, and CNIBS/R-K model. The calculated values of RMSD and RAD are less than 0.74 × 10−6 and 0.98%, separately. In brief, the selected models can correlate the solubility of biapenem in the monosolvents and binary solvent mixtures very well. Finally, the experimental data measured by this work could be used to guide the purification process and preparation of pharmaceutical preparations in industry.

Table 5. Parameters of the Modified Apelblat Model and RMSD Values for Biapenem in Different Monosolvents modified Apelblat model solvent

A

B

C

106 RMSD

methanol n-propanol isopropanol acetone ethyl acetate acetonitrile ethanol DMF NMP DMSO

−65.588 −36.121 −41.950 −5.407 −91.476 −114.758 20.293 −95.298 −144.630 −143.250

30.989 −1425.466 −1369.670 −4777.458 2009.139 2832.763 −3855.866 2276.782 4683.018 4534.003

9.668 5.276 6.179 1.603 13.198 16.742 −3.153 13.727 21.005 20.831

0.19 0.12 0.08 0.05 0.27 0.26 0.15 0.27 0.42 0.39

Table 6. Parameters Values of Jouyban−Acree Model and Apelblat− Jouyban−Acree Model along with RAD and RMSD Values for Biapenem in Ethyl Acetate + Methanol Apelblat−Jouyban− Acree

Jouyban−Acree parameter

value

parameter

value

J0 J1 J2

56.177 27.302 −32.517

A1 B1 C1 A2 B2 C2 J0 J1 J2

−91.476 2009.139 13.198 −65.588 30.989 9.668 52.749 13.466 −41.086 0.98 0.74

ethyl acetate + methanol

RAD·102 RMSD·106

0.83 0.64

■

AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. ORCID

Renjie Xu: 0000-0001-5541-1622 Funding

This work was supported by the Natural Science Foundation of Guangling College, Yangzhou University (Grant No. ZKZD18005)

solubility data with the calculated solubility data, Figures 3 and 4 plot the correlated solubility with the modified Apelblat equation and the Jouyban−Acree equation, respectively. From the results in Table 5, the highest RMSD is in the biapenem + NMP (0.42 × 10−6) system. However, the maximum RAD values are 0.80%. For mixed solvent systems, the RAD and RMSD values are listed in Tables 6 and 7. The RAD values are less than 0.98%, and the RMSDs are no greater than 0.74 × 10−6. In general, all models could fit the solubility data of biapenem in the studied pure and binary solvent mixtures very well.

Notes

The authors declare no competing financial interest.

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REFERENCES

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Table 7. Parameters Values of CNIBS/R-K Model Together with Calculated RAD and RMSD Values for Biapenem in (Ethyl Acetate + Methanol) T/K

B0

B1

B2

B3

B4

100 RAD

106 RMSD

283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15

−10.888 −10.727 −10.559 −10.393 −10.241 −10.082 −9.927 −9.787 −9.627

3.333 2.968 2.684 2.393 2.319 2.091 2.213 1.799 1.827

−5.209 −4.418 −3.646 −2.886 −2.815 −2.276 −3.397 −1.725 −2.519

4.298 3.585 2.599 1.706 1.520 0.980 2.820 0.393 1.896

−1.397 −1.176 −0.722 −0.364 −0.219 −0.040 −0.927 0.213 −0.580

0.36 0.37 0.55 0.33 0.55 0.42 0.60 0.40 0.23

0.14 0.15 0.25 0.22 0.33 0.30 0.57 0.38 0.25

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DOI: 10.1021/acs.jced.8b01051 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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DOI: 10.1021/acs.jced.8b01051 J. Chem. Eng. Data XXXX, XXX, XXX−XXX