Extraction Equilibria of Glycolic Acid Using Tertiary Amines - American

Article pubs.acs.org/jced

Extraction Equilibria of Glycolic Acid Using Tertiary Amines: Experimental Data and Theoretical Predictions Dipaloy Datta,*,† Yavuz Selim Aşcı̧ ,‡ and Amaç Fatih Tuyun§ †

Malaviya National Institute of Technology (MNIT), Chemical Engineering Department, Jaipur, Rajasthan 302017, India Istanbul University, Engineering Faculty, Chemical Engineering Department, 34320 Istanbul, Turkey § Istanbul University, Engineering Faculty, Engineering Science Department, 34320 Istanbul, Turkey ‡

ABSTRACT: Extraction equilibrium of glycolic acid (1.5 mol·kg−1) from aqueous solutions has been carried out using a solvent/extractant consisting of 50 vol % trioctylamine (TOA) and 50 vol % tridodecylamine (TDA) in the concentration range of 0.194 mol·kg−1 to 1.163 mol·kg−1. The extract phase is diluted with dimethyl phthalate (DMP), methyl isobutyl ketone (MIBK), 2-octanone, 1-decanol, and cyclohexylacetate (CHA). The data are represented by calculating distribution coefficients (D), loading factors (Z), and extraction efficiencies (% E) using experimental values. The highest value of D for the glycolic acid extraction is found to be 4.44 for DMP, 4.09 for MIBK, 3.78 for 2-octanone, 3.51 for 1-decanol, and 2.71 for CHA. A substantial amount (73.05 % to 81.61 %) of glycolic acid is recovered by all the amine-diluent systems and at 1.163 mol·kg−1 initial concentration of (TOA + TDA) mixture.

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INTRODUCTION The demand for the sustainable and ecofriendly technology for both energy and platform chemicals has gained increasing interest in recent years and opened new ways for researchers and technologists to think in different directions to reduce reliance on fossil resources. Sustainable growth of the chemical process industry requires an integrated strategy in which the benefits of safety, health, and environmental aspects have to be accounted for with technological and economical objectives. This setback can be overcome by using biobased technologies. Therefore, researchers are continuously working to develop biobased production systems that have potential and sustainability.1−3 Carboxylic acids are weak organic acids and extremely useful as starting materials for the production of esters, amides, and acid chlorides in the chemical industries. Most of them are produced by microorganisms as intermediates in major metabolic pathways. Also, these acids are found in the aqueous streams generated from fermentation broth, industrial wastewater, and bio-oil.1,3−6 Glycolic acid finds applications in household and institutional cleaning and personal skin care. Due to its high solubility in water and small molecular size, it can penetrate deep inside concrete residues and react from within. This distinct combination of properties makes it an ideal cleaner for maintaining tools, equipment, and vehicles. The biodegradability of this acid makes it easier to dispose of than other cleaning agents (e.g., hydrochloric or phosphoric acid). It is classified as an “A3” acid cleaner by the U.S. Department of Agriculture. With a low pKa (= 3.83) and molecular weight, it makes short work of soap scum and mineral scales, removing soil thoroughly. Glypure is a product of DuPont used in many © XXXX American Chemical Society

personal care and cosmetics products and is the most popular active ingredient in antiaging formulations with strong consumer recognition. It also can readjust the water percentage in the epidermis, allowing for smoother, softer, and more radiant skin.7 The production of carboxylic acids from renewable carbon sources by microbial fermentation processes is a promising approach and has been known for more than a century (Table 1). Synthesis by fermentation is a green, renewable, and environment-friendly path to produce industrially important carboxylic acids. However, the present synthesis route faces two major setbacks: first, product inhibition in the fermentation broth at low concentrations of acid and, second, recovery of acid from a dilute fermentation broth. In general, the latter accounts for almost 50% of the total production cost and hence is a major cost driver for biobased processes. Several recovery processes are used for the recovery of carboxylic acids from their aqueous solutions such as ion exchange chromatography,15,16 adsorption,17−19 electrodialysis,20,21 anion exchange,22,23 liquid−liquid extraction,21,24 membrane separation,25,26 ultrafiltration,20 nanofiltration,27 reverse osmosis,27 distillation,28,29 precipitation,30,31 and reactive extraction.32−38 Among the studied techniques, reactive liquid−liquid extraction has gained attention as a promising method for the recovery of carboxylic acids from a dilute fermentation broth. Compared with other recovery methods, reactive liquid−liquid extraction is expected to require less Received: June 15, 2015 Accepted: October 20, 2015

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DOI: 10.1021/acs.jced.5b00497 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data

Article

Table 1. Microbial Production of Organic Acids concentration microorganisms

carbon source

acetic propionic itaconic citric butyric lactic glycolic nicotinic succinic isonicotinic

Propionibacterium acidipropionici Propionibacterium acidipropionici Aspergillus terreus Aspergillus niger Clostridium butyricum Lactobacillus delbrueckii Acidovorax facilis 72 W Saccharomyces cerevisiaee Corynebacterium glutamicum Fusarium solani, Aspergillus niger

glucose glucose glucose cane molasse glucose hydrolyzed cane sugar glycolonitrile nicotinamide glucose 4-cyanopyridine

THEORETICAL SECTION The following reactions can be written to explain the extraction of glycolic acid (HA) with amine (R3N): In the reaction equation, the undissociated part of the acid in the organic (E) or aqueous phase (R) is indicated by HA, organic phase species are marked with E, and square brackets denote activities. The thermodynamic extraction constants are used to characterize Reaction 1;39

EXPERIMENTAL SECTION The chemicals with their physical properties used in the present equilibrium study are listed in Table 2. The mixture of amine was prepared with 50% TOA + 50% TDA (w/w). In the reactive extraction experiment, an aqueous solution of glycolic acid (1.5 mol·kg −1 ) was contacted with six different concentrations (0.194 mol·kg−1, 0.388 mol·kg−1, 0.583 mol· kg−1, 0.777 mol·kg−1, 0.969 mol·kg−1, and 1.163 mol·kg−1) of

i(HA)R + j(R3N)E ↔ ((HA)i ·(R3N)j )E i = 1, p ;

water TOA TDA glycolic acid DMP MIBK 2-octanone 1-octanol CHA

deionized and distilled Merck Merck Merck Merck Merck Carlo-Erba Merck Merck

purity

> 93% > 95% 70% solution in water > 99% > 99% > 99% > 99% > 99%

n Da

997

1.3325

808 823 1257

1.4485 1.4578 1.4120

1190 800 817 830 970

1.5137 1.3962 1.4161 1.4290 1.4432

(p = number of acid molecules;

Equation 1 shows in terms of undissociated species hydrogen ions and glycolate anions, which is also used in the literature on amine extraction of glycolic acid. Keeping in mind the dissociation equilibrium, it can be concluded that both concepts are equivalent, the only difference being in the values of equilibrium constants. Equation 2 represents that the activities are replaced by the products of molalities and molar activity coefficients.40

ρ source

j = 1, q

(1)

q = number of amine molecules)

Table 2. Purity of Substances Studied and Their Physical Properties at 298.15 K

compound

0.041 to 0.132 1.236 0.049

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(kg· m−3)a

ref Woskow and Glatz, 19918 Woskow and Glatz, 19918 Yahiro et al., 19959 Ikram-ul et al., 200410 Guo-qing, 200511 Kadam et al., 200612 Li et al., 20064 Cantarella et al., 20085 Okino et al., 200813 Malandra et al., 200914

0.152 0.432 0.633 0.593 0.190 1.489

the amine mixture (TOA + TDA) diluted with individual solvent. Equilibrium experiments were performed at 298.15 K. To carry out the equilibrium experiments, 5 mL of glycolic acid solution was mixed with 5 mL of organic solution in an Erlenmeyer flask and kept for shaking in a Nuve Shaker ST402 bath for 4 h. After equilibrium, the net solution mixture was centrifuged by Nuve CN180 machine at 2000 rpm for another 30 min to get clear separation of phases. Samples of the aqueous solution at equilibrium were titrated with aqueous sodium hydroxide (relative uncertainty 1%) in a Schott TitroLine Easy Module 2 machine to know the concentration of acid. The amount of acid in the extract phase was determined by mass balance.

energy input, provide higher yields and selectivity, and facilitate the establishment of closed-loop processes.33−38 Although tertiary amines such as trioctylamine (TOA)33−35,38 or tridodecylamine (TDA)35−37 dissolved in some diluents were used actively in the recovery of different organic acids with higher distribution coefficients, there is a lack of knowledge concerning the effect of mixed-amine extractant on the recovery of carboxylic acids, especially glycolic acid. However, a mixture of two different amines was chosen since they have a high affinity and extraction capability for carboxylic acids as obvious from a recent study.35 Five different diluents were used to investigate the extractability of glycolic acid by a mixture of tertiary amines (TOA + TDA). The solvents were considered from various categories of chemicals: cyclohexyl acetate (CHA), dimethyl phthalate (DMP), 2-octanone, 1-decanol, and methyl isobutyl ketone (MIBK). Therefore, equilibrium extraction experiments are carried out to investigate the effect of mixed extractant (TOA + TDA) on the distribution coefficient, extraction efficiency, and loading factor of glycolic acid reactive extraction.

a

(mol·kg−1)

organic acids

(K ij)E = [(HA)i ·(R3N)j ]E /([HA]i )R ([R3N]j )E

(2)

(K ij)E = (bij)E ·aij /(baaa)i E (beae) jE

(3)

In eq 3, a refers to acid and e refers to amine. The activity coefficients of undissociated glycolic acid in water can be omitted in the first approximation as presented by Levien.41 It is also assumed that the activity coefficients are constant because only undissociated glycolic acid molecules have been extracted in the organic phase. The conditional extraction constants are given by the following expression:

Standard uncertainties u are u(ρ) = 1 kg·m−3, u(nD) = 0.0001. B



Article

K ij = (bij)E /(ba i)R (be j)E i = 1, p ;

(4)

■

j = 1, q

∑ ∑ iK ij(ba i)R (be j)E

i = 1, p ;

j = 1, q

(Ca)Ra

∑ ∑ jK ij(ba i)R (be j − be0)E = 0

i = 1, p ;

(6)

j = 1, q

A unique solution has been exhibited between zero and the aqueous phase molalities of undissociated acid, according to the dissociation equilibrium in eq 6. Possible (i, j) combinations for i = 1, p and j = 1, q need not to be taken into account as per the results reported by Vanura and Kuca.42 The extraction of acid by pure diluent may be studied in order to obtain the distribution coefficient, but there is no evidence of the true value of this coefficient in the presence of amine and its complexes with the acid. The changes of Kij with amine concentration can be caused by both the conditional character of this constant and the stoichiometry of complex formation. The loading of the extractant, Z, is defined as the total concentration of acid in the organic phase divided by the total concentration of amine in organic phase. The expression for the loading, Z, can be derived from eqs 5 and 6 in the form: Z = (ba)E /(be 0)E ↔ [∑ iK i1(ba i)R ]/[1 +

(mol·kg )

pH

1.481 1.457 1.487 1.488 1.482

0.019 0.043 0.013 0.012 0.018

1.73 1.72 1.82 1.45 1.83

a

D

(%)

0.013 0.029 0.008 0.007 0.012

1.297 2.854 0.835 0.770 1.224

Standard uncertainties u are u(C) = 0.001 C, u(pH) = 0.01, and the combined expanded uncertainty Uc is Uc(D) = 0.0001 D, Uc(E) = 0.0001 E.

Table 4. Experimental Results of the Extraction of Glycolic Acid with (TOA + TDA)/Individual Diluting Solvents

diluent DMP

MIBK

2octanone

(8)

The efficiency of extraction, E, is expressed as (9)

This fact can be explained by the formation of two or three acid−amine complexes, which are affected by the diluent in different ways. Using the mass action law, the reactive extraction equilibrium of glycolic acid with tertiary amine is modeled by postulating the formation of various stoichiometric acid−amine complexes. Here in this study, two possible acid− amine complexes such as (HA)·(R3N) and (HA)·(R3N)2 were assumed to exist in the organic phase as per Yerger−Barrow43 and Bizek et al. approaches.44 In case of proton-donating diluent like 1-decanol, the extraction process can be described by the reactions 10 and 11. The resulting acid−amine complexes are supposed to be stabilized due to hydrogen bonding with diluent. Figure 2 shows the effect of amine concentration on loading. In this study, an increase in the loading ratio was observed with all the solvents with an increase in the extractant concentration. The trend is consistent with the results reported in the literature.43,44 K11

a

(mol·kg )

The distribution coefficient for glycolic acid extraction from water into the organic phase was determined as

(HA)R + (R3N)E ↔ ((HA) ·(R3N))E

Ea

−1

diluent

j = 1, q

E = (1 − ((ba)E /(ba i)R )) × 100

(Ca)Ea

a

∑ K i1(ba i)R

D = (ba)E /(ba)R

−1

DMP MIBK 2-octanone 1-decanol CHA

(7)

i = 1, p ;

(11)

Table 3. Distribution of Glycolic Acid between Solvents and Water

(5)

The molality of free amine is given by the following equation: (be)E +

K12

RESULTS AND DISCUSSION At first, the extraction of glycolic acid was performed using pure solvent containing five different diluents such as DMP, MIBK,

The mathematical model of equilibrium is obtained in the form to combine the balance equations of acid and amine in the organic phase with eq 4: (ba)E =

(HA)R + 2(R3N)E ↔ ((HA) ·(R3N)2 )E

1-decanol

CHA

(Ce)Ea

(Ca)Ra

(Ca)Ea

Ea

(mol· kg−1)

(mol· kg−1)

(mol· kg−1)

pHa

Da

Za

(%)

0.194 0.388 0.583 0.777 0.969 1.163 0.194 0.388 0.583 0.777 0.969 1.163 0.194

1.190 0.912 0.665 0.455 0.350 0.276 1.198 0.912 0.678 0.494 0.366 0.295 1.218

0.310 0.588 0.835 1.045 1.150 1.224 0.302 0.588 0.822 1.006 1.134 1.205 0.282

1.82 1.97 2.04 2.10 2.29 2.47 1.81 1.97 2.11 2.20 2.42 2.57 1.90

0.26 0.64 1.26 2.29 3.29 4.44 0.25 0.64 1.21 2.04 3.10 4.09 0.23

1.600 1.515 1.433 1.344 1.187 1.053 1.559 1.515 1.409 1.295 1.171 1.036 1.454

20.69 39.19 55.68 69.64 76.69 81.61 20.17 39.19 54.77 67.09 75.62 80.36 18.80

0.388 0.583 0.777 0.969 1.163 0.194 0.388 0.583 0.777 0.969 1.163 0.194 0.388 0.583 0.777 0.969 1.163

0.971 0.716 0.555 0.427 0.314 1.266 1.003 0.798 0.602 0.444 0.333 1.275 1.011 0.840 0.691 0.546 0.404

0.529 0.784 0.945 1.073 1.186 0.234 0.497 0.702 0.898 1.056 1.167 0.225 0.489 0.660 0.809 0.954 1.096

1.95 2.01 2.09 2.23 2.39 1.57 1.78 2.05 2.14 2.26 2.75 1.97 2.05 2.11 2.19 2.35 2.44

0.55 1.10 1.70 2.52 3.78 0.19 0.51 0.88 1.49 2.38 3.51 0.18 0.48 0.79 1.17 1.75 2.71

1.364 1.345 1.217 1.108 1.020 1.208 1.280 1.204 1.155 1.089 1.004 1.157 1.261 1.330 1.041 0.985 0.942

35.28 52.31 63.02 71.55 79.10 15.62 33.12 46.78 59.85 70.38 77.81 14.97 32.61 44.03 53.93 63.61 73.05

a

Standard uncertainties u are u(C) = 0.001 C, u(pH) = 0.01, and the combined expanded uncertainty Uc is Uc(D) = 0.01 D, Uc(Z) = 0.001 Z, Uc(E) = 0.01 E.

2-octanone, 1-decanol, and CHA. The results are presented in Table 3. The values of physical distribution coefficient were

(10) C



Article

Figure 3. Variation of extraction efficiency of glycolic acid with concentration of amine in different individual diluting solvents. Symbols: ■, DMP; ▲, MIBK; ●, 2-octanone; □, 1-decanol; Δ, CHA.

Figure 1. Variation of distribution coefficients of glycolic acid with concentration of amine in different individual diluting solvents. Symbols: ■, DMP; ▲, MIBK; ●, 2-octanone; □, 1-decanol; Δ, CHA.

Table 5. Values of the Equilibrium Extraction Constants (Ce)E diluent DMP

MIBK

2-octanone

Figure 2. Variation of loading factors of glycolic acid with concentration of amine in different individual diluting solvents. Symbols: ■, DMP; ▲, MIBK; ●, 2-octanone; □, 1-decanol; Δ, CHA.

found to be very low with all the solvents tested. The acid molecules showed a relatively higher attraction toward water molecules than solvent molecules. Therefore, the extraction of glycolic acid by these solvents alone may not be an attractive and economical method for the recovery. To overcome the limitations of physical extraction, reactive extraction with a suitable mixed amine extractant (TOA + TDA) was carried out by varying concentration in the range of 0.194 mol·kg−1 to 1.163 mol·kg−1. The results of glycolic acid extraction with mixed extractant (TOA + TDA) are shown in Table 4. The effect of (TOA + TDA) on the distribution coefficient (D), loading ratio (Z), and extraction efficiency (% E) is shown in Figures 1, 2, and 3, respectively. It was seen that there is a significant increase in the distribution of acid when (TOA + TDA) is added to different solvents. The values of D increased by a large factor (DMP, 0.031 to 4.44; MIBK, 0.029 to 4.09; 2-octanone, 0.008 to 3.78; 1-decanol, 0.007 to 3.51; CHA, 0.012 to 2.71) when compared with the physical extraction values of acid. The mixture of amine + diluent system showed an enhancement in the

1-decanol

CHA

−1

K11

K12 −1

(mol·kg )

(kg·mol )

0.194 0.388 0.583 0.777 0.969 1.163 0.194 0.388 0.583 0.777 0.969 1.163 0.194 0.388 0.583 0.777 0.969 1.163 0.194 0.388 0.583 0.777 0.969 1.163 0.194 0.388 0.583 0.777 0.969 1.163

1.35 1.66 2.16 2.95 3.40 3.82 1.30 1.66 2.08 2.63 3.20 3.52 1.20 1.41 1.88 2.19 2.60 3.25 0.96 1.28 1.51 1.92 2.45 3.02 0.91 1.25 1.35 1.51 1.80 2.33

(kg ·mol−2) 2

4.93 3.30 2.59 2.47 2.53 2.59

recovery of acid with an increase in the concentration (from 0.194 mol·kg−1 to 1.163 mol·kg−1) in the extract phase. The D values were found in the range of 0.26 to 4.44 with DMP, 0.25 to 4.09 with MIBK, 0.23 to 3.78 with 2-octanone, 0.19 to 3.51 with 1-decanol, and 0.18 to 2.71 with CHA. According to Table 4 and Figure 1, TOA + TDA (1.163 mol· kg−1) with individual solvent recovered glycolic acid in the D



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CONCLUSIONS The equilibrium study on reactive extraction of glycolic acid using an extractant mixture, TOA + TDA, dissolved in five different solvents is performed. The extraction capacity of mixed extractant is found to be higher with DMP. The order in which the solvents can recover glycolic acid is found to be DMP > MIBK > 2-octanone >1-decanol > CHA. The highest values of KD and % E for the reactive extraction of glycolic acid are found to be 4.44 and 81.61 %, respectively, at 1.163 mol· kg−1 initial extractant concentration. Glycolic acid mainly forms 1:1 and 1:2 solvates with the extractant system. The effect of mixed extractant (TOA + TDA) is found to be prominent for the efficient recovery of glycolic acid from the aqueous solution generated from fermentation broth.

following order: DMP (D = 4.44) > MIBK (D = 4.09) > 2octanone (D = 3.78) > 1-decanol (D = 3.51) > CHA (D = 2.71). The solvents giving higher distribution can be explained due to the formation of acid−amine solvates in the organic phase. The molecular size and polarity of the solvent are the two different properties of the solvent that may affect the formation of acid−amine solvates in two different ways. The cavity, which is the space in the volume of liquid left by occupying solvent molecule, is identified by the molecular size, which also means distance between two adjacent molecules. For example, the solvation ability of the solvent molecule decreases with an increase in the molecular size.18 The polarity of the solvent is an another important factor. Because polar diluents ensure higher distributions, they are found to be more effective and convenient diluents than inert ones (nonpolar).19 Polarity is explained based on the transition energy expressed as ET. Kosower18,20 expressed the polarity parameter as a function of the molar transition energy, ET (in kcal/mol). Higher values of polarity parameter are equivalent to high polarity of the solvent. The solvation of an acid−amine complex by the diluent has a pivotal role in the extraction of organic acids. The interactions between the acid−amine complex and the diluent in the organic phase can take place by a general solvation interaction or a specific interaction of the diluent molecule with the complex molecule. Inert diluents, for example, hexane and isooctane, do not contribute significantly to the distribution of acid molecule into the organic phase and provide a low value of distribution coefficient of acid. These inactive diluents give very low solvation of the polar complexes. Polar diluents such as DMP, MIBK, and 2-octanone can increase the extraction process by supplying a good solvating media for the acid− amine complexes formed. The chain length of the esters affect their polarity. So esters with short chain have higher polarity than esters with long chain, and with an increase in the chain length, the polarity of esters decrease. Therefore, the solubility power of the solvent for the acid−amine complex decreases. Both of these two properties determine the solvation ability of a solvent and are responsible for higher extraction efficiency. Not only does polarity assign the solvating ability of the diluents, but also the solvent’s capability to form H-bond is a crucial factor in the extraction. The recovery of acid using alcohol as diluent is prone to H-bond formation, and 1-decanol as used in the study gave a high distribution coefficient of acid.20 The loading curve (Figure 2) showed the effect of mixed amine concentration on the loading of acid. The loading curve is a plot between Z and initial amine concentration in the organic phase. Overloading, that is, loading greater than unity, indicated that more than one acid molecule per amine molecule was attached in the complex. The values of Z were observed between 1.053 and 1.600 for DMP, 1.036 and 1.559 for MIBK, 1.020 and 1.454 for 2-octanone, 1.004 and 1.208 for 1-decanol, and 0.942 and 1.157 for CHA. The loading factors of all solvents used in the current study were found to be decreased as seen from Figure 2. Figure 3 explained the effect of amine concentration on the extraction efficiency of (TOA + TDA)-diluent mixture. There was an increase in the extraction efficiency by increasing initial concentration of binary amine system in the organic phase. The highest extraction efficiency of glycolic acid was found as 81.61 % with DMP at 1.163 mol·kg−1 initial concentration of binary amine system. The values of the extraction constants (K11 and K12) were estimated using eq 5 for all amine concentrations and are listed in Table 5.

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Notes

The authors declare no competing financial interest.

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REFERENCES

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Extraction Equilibria of Glycolic Acid Using Tertiary Amines - American

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