liquid–liquid extraction of lactic acid with Alamine 336

The extraction of lactic acid (HL) from aqueous solutions by Alamine 336 (B) dissolved in toluene was studied. Experiments were performed in the temperature range of 25–60°C and for two amine concentrations of 20 and 40% (v/v) in toluene. The extent to which the organic phase (amine + toluene) may be loaded with lactic acid is expressed as a loading ratio, Z = C_HL /C_B. Z values are independent of the amine concentration and, hence, the extracted complex contains only one molecule of amine. Z decreases with increasing temperature. Experimental results indicate that the system presents overloading, i.e. Z > 1. The extraction equilibrium may be interpreted as a result of consecutive formation of three acid–amine species with stoichiometries of 1:1, 2:1 and 3:1.     

Equilibria and kinetics for reactive extraction of lactic acid using Alamine 336 in decanol

Lactic acid is an important commercial product and extracting this from aqueous solution is a growing requirement in fermentation‐based industries. The design of an amine extraction process requires (i) equilibrium and (ii) kinetic data for the acid–amine (solvent) system used. The equilibrium complexation constants for ratios of (1:1) and (2:1) have been estimated. The kinetics of extraction of lactic acid by Alamine 336 in decanol has also been determined. The reaction between lactic acid and Alamine 336 in decanol in a stirred cell falls in Regime 3, ie extraction accompanied by a fast chemical reaction occurring in the diffusion film. The reaction has been found to be zero order in Alamine 336 and first order in lactic acid with a rate constant of 0.21 s^?1. These data will be useful in the design of extraction processes. © 2002 Society of Chemical Industry     

Extraction of citric acid from aqueous solutions with Alamine 336: equilibrium and kinetics

Citric acid is one of the organic acids for which the world market is growing every year. This article describes equilibria and kinetic studies for the extraction of citric acid by Alamine 336 with methyl‐iso‐butylketone (MIBK) as diluent. The theory of extraction accompanied by a chemical reaction has been used to obtain the intrinsic kinetics of extraction of citric acid by Alamine 336 in MIBK. The reaction has been found to be first order in both Alamine 336 and citric acid with a rate constant of 0.013 m³ kmol^?1 s^?1. Copyright © 2004 Society of Chemical Industry     

Separation of phenylacetic acid, 6-aminopenicillanic acid and penicillin G with electrodialysis under constant current

The separation behavior of phenylacetic acid (PAA), 6-aminopenicillanic acid (6-APA) and penicillin-G (Pen-G) with electrodialysis under constant current was studied. The effects of ionic concentrations and current density on their separation behavior were investigated. The sorption of PAA, 6-APA and Pen-G and in the anion exchange membrane, and the variations of the applied voltage and current efficiencies with time during electrodialysis were also examined. It was found that the molecular size and the affinity toward the anion exchange membrane played a key role for the electrodialysis of PAA, 6-APA and Pen-G. Phenylacetic acid had the lowest affinity toward the membrane but the fastest transport rate. Penicillin-G had the highest affinity toward the membrane but the slowest transport rate. With the increase of Pen-G concentration, the concentration polarization of Pen-G in the vicinity of anion exchange membrane became very serious, which severely retarded the transport of PAA and 6-APA. Although the increase of current density accelerated the transport of PAA, 6-APA and Pen-G, more serious concentration polarization of Pen-G occurred and the separation ratio of PAA to 6-APA decreased.     

Reactive extraction of itaconic acid using tri‐n‐butyl phosphate and aliquat 336 in sunflower oil as a non‐toxic diluent

Itaconic acid finds a place in various industrial applications. It can be produced by biocultivation in a clean and environment friendly route but recovery of the acid from the dilute stream of the bioreactor is an economic problem. Reactive extraction is a promising method to recover carboxylic acid but suffers from toxicity problems of the diluent and extractant employed. So there is need for a non‐toxic extractant and diluent or a combination of less toxic extractants in a non‐toxic diluent that can recover acid efficiently. Effect of different extractants: tri‐n‐butylphosphate (TBP) (an organophosporous compound) and Aliquat 336 (a quaternary amine) in sunflower oil was studied to find the best extractant–sunflower oil combination. Equilibrium complexation constant, K_E, values of 1.789 and 2.385 m³ kmol^?1, respectively, were obtained for itaconic acid extraction using TBP and Aliquat 336 in sunflower oil. The problem of toxicity in reactive extraction can be reduced by using a natural non‐toxic diluent (sunflower oil) with the extractant. Copyright © 2010 Society of Chemical Industry     

Interfacial mass transfer in extraction of amino acid by aliquat 336 in organic phase

Reactive extraction of L -phenylalanine from alkaline aqueous solution into xylene in the presence of tri-octyl-methyl-ammonium chloride (ALIQUAT 336) as complexing agent was studied using a stirred transfer cell. The study investigated the effects of carrier concentration and temperature on mass transfer rates. Transfer rate across the interface in the presence of surfactant molecules was also studied. A two-film model was proposed by considering film mass transfer resistances at the aqueous and organic phases. The model predicted adequately the experimental time-concentration data at different carrier concentrations and temperatures. The model was modified to take into account the presence of surfactant in the organic phase.     

Separation of phenylacetic acid using tri-n-butyl phosphate in hexanol: Equilibrium and kinetics

Equilibrium and kinetics studies are required to design the continuous extraction process for the acid-extraction system. In the present study, an attempt has been made to investigate the equilibrium and kinetics parameters for the reactive extraction of phenylacetic acid (PAA) with tri-n-butyl phosphate (TBP) in hexanol. The equilibrium results show that the formation of the (1:1) PAA–TBP complex in the organic phase with an overall equilibrium complexation constant (K_e) was 78.74 and 29.15 m³.kmol^?1 for TBP concentrations of 0.734 and 1.464 kmol.m^?3, respectively. The mass transfer coefficients (k_L) for PAA were found to be in the range of 3.7 × 10^–5–6.2 × 10^–5 m.s^?1. Based on the Hatta number (H_a = 8.48), the reaction was found to be fast chemical reaction (regime 3) with the order of reaction as 0.77 and 0.36 with respect to PAA and TBP, respectively. The rate constant of the reaction was obtained as 0.017 kmol.m^?3.s^?1.     

FBRM and PVM investigations of the double feed semi-batch crystallization of 6-aminopenicillanic acid

6-Aminopenicillanic acid (6-APA) is a crucial pharmaceutical intermediate in the chemistry of semi-synthetic antibiotics. The focused beam reflectance measurement (FBRM) technology and particle vision measurement (PVM) technology were employed to the processes of online-monitoring of 6-APA crystallization behavior in a double-feeding semi-batch crystallizer. Experiments were carried out with four kinds of double-feeding policies and the results were compared with the traditional single-feeding. Records and analysis of FBRM indicated that the nucleation of double feeding policy was much higher than single policy, and chord length of 6-APA was almost determined and had little change after the nucleation peak. Ostwald ripening process had no significant effect on further growth of 6-APA crystal. PVM images showed that the crystal habit of 6-APA was continuously changed during the crystallization process. The development of (002) face in the final crystal for the five feeding policies were different.     

Reactive Extraction of Levulinic Acid Using TPA in Toluene Solution: LSER Modeling,Kinetic and Equilibrium Studies

Abstract

Levulinic acid, a carboxylic acid containing ketone structure, is a clear to brownish semi‐solid melting at 37°C; soluble in alcohol, ether, and chloroform, levulinic acid can be used as an acidulant in foods and beverages. Organic solutions of amines are being used increasingly to separate organic acids from aqueous mixture solutions by reactive extraction. The design of an amine extraction process requires kinetic data for the acid–amine+solvent system used. Kinetic studies for the extraction of levulinic acid from aqueous solution with tripropylamine (TPA) diluted in toluene were carried out using a stirred cell for kinetic studies. Equilibria for levulinic acid extraction by TPA in toluene as a diluent have been determined. All measurements were carried out at 298.15 K. The equilibrium data were also interpreted by a proposed mechanism of complexation by which (1∶1) and (2∶1) acid‐amine complexes are formed. Kinetics of extraction of levulinic acid by TPA in toluene has also been determined. The results of the liquid‐liquid equilibrium measurements were correlated by a linear solvation energy relationship (LSER).     

Reactive extraction of succinic acid using supercritical carbon dioxide

Reactive extraction using supercritical carbon dioxide (scCO₂) and tri-n-octylamine (TOA) was evaluated as a separation method of succinic acid from an aqueous solution. The reactive extraction of succinic acid was performed at varying initial acid concentrations in aqueous solution (0.07–0.45 mol?dm^?3), temperature (35–65°C) and pressure (8–16 MPa). The succinic acid separation was conducted in both batch mode and semi-continuous mode. The highest reactive extraction efficiency of approx. 62% was obtained for the process conducted in semi-continuous mode at 35°C and 16 MPa for the initial acid concentrations in aqueous phase of 0.39 mol?dm^?3.     

Equilibrium of liquid-liquid extraction of 2-phenylbutyric acid enantiomers: Experiment and model

The utilization of liquid–liquid extraction for the separation of 2-phenylbutyric acid(2-PBA) enantiomers was proposed. Factors affecting the extract process were investigated, including organic solvents, β-cyclodextrin derivatives, cyclodextrin concentration, p H and temperature. A model was proposed to describe the separation process based on the homogeneous phase reaction mechanism. Important parameters of this model were determined experimentally. The physical distribution coefficients for molecular and ionic 2-PBA were0.129 and 7.455, respectively. The equilibrium constants of the complexation reactions were 89.36 and36.78 L·mol~(-1) for(+)-and(-)-2-PBA, respectively. The model was verified by experiments and proved to be an excellent means to optimize the separation system. Through modeling prediction and experiment, the best conditions(e.g., pH value of 3.00, extractant concentration of 0.1 mol·L~(-1), temperature of 5.0 °C) were acquired. Under this condition, the maximum enantioselectivity(2.096) was obtained.     

Reactive extraction of propionic acid using tri‐n‐octylamine,tri‐n‐butyl phosphate and aliquat 336 in sunflower oil as diluent

BACKGROUND : Propionic acid is widely used in chemical and allied industries and can be produced by biocultivation in a clean and environmentally friendly route. Recovery of the acid from the dilute stream from the bioreactor is an economic problem. Reactive extraction is a promising method of recovering the acid but suffers from toxicity problems of the solvent employed. There is thus a need for a non‐toxic solvent or a combination of less toxic extractants in a non‐toxic diluent that can recover acid efficiently. RESULTS: The effect of different extractants (tri‐n‐butylphosphate (TBP), tri‐n‐octylamine (TOA) and Aliquat 336) and their mixed binary solutions in sunflower oil diluent was studied to find the best extractant‐sunflower oil combination. Equilibrium complexation constant, K_E, values of 4.02, 3.13 and 1.87 m³ kmol^?1 were obtained for propionic acid extraction using Aliquat 336, TOA and TBP, respectively, in sunflower oil. The effect of different modifiers (1‐decanol, methylisobutyl ketone, butyl acetate and dodecanol) on the extraction was also studied and it was found that modifiers enhance extraction, with 1‐decanol found to be the best. CONCLUSION: The problem of toxicity in reactive extraction can be reduced by using a non‐toxic diluent (sunflower oil) or a modifier in a non‐toxic solvent, with the extractant. The addition of modifiers was found to improve the extraction. Copyright © 2008 Society of Chemical Industry     

In situ reactive extraction of lactic acid from fermentation media

Extractive lactic acid fermentation was investigated in the presence of sunflower oil and Alamine‐336 (with oleyl alcohol as the diluent solvent). Lactic acid was produced in various media at 37 °C using Lactobacillus delbrueckii (NRRL‐B 445). First, the effects of oleyl alcohol (33.3%, v/v), immobilisation, and immobilisation in the presence of sunflower oil (5, 10, 15%, v/v) on lactic acid production were investigated. It was found that oleyl alcohol did not affect production while addition of sunflower oil increased lactic acid production from 10.22 to 16.46 gdm^?3. On the other hand, a toxic effect was observed for oleyl alcohol solutions containing 15–50% (v/v) Alamine‐336. A maximum total lactic acid concentration of 25.59 gdm^?3 was obtained when an oleyl alcohol solution containing 15% (v/v) Alamine together with immobilised cells with 15% (v/v) sunflower oil was used. This value was about 2.5 times that obtained from fermentation without organic solutions. © 2001 Society of Chemical Industry     

三烷基胺萃取氨基磺酸及其废水的特性研究

p-Amino benzene sulfonic acid (PABSA) is selected as the solute with amphoteric functional group, Lewis acid and Lewis base, to be separated from its dilute solutions. An aliphatic, straight chain amine, Alamine 336, is used as the extractant, and kerosene, 1-octanol, chloroform, butyl acetate and benzene as the diluent. The effects of pH value of solution, extractant concentration, salt and types of diluent on the distribution coefficient, D, are studied. There is a peak of D value with pH value of solution, the polar diluents are favorable for extracting PABSA, and the salt in aqueous phase reduces values of D apparently. The extraction equilibrium is described using the mass action law, and the calculated data according to the proposed model agree with the experimental data well. Further, the extraction behavior for other amino benzene sulfonic acids, 1-amino-8-naphtol-3,6-disulfonic acid (H acid) and 4,4′-diaminostilbene-2,2′-disulfonic acid (DSD acid), is investigated in a wide pH value region. Finally. H acid and DSD acid are successfully removed from wastewater by the extraction with Alamine 336.