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Preparation of Lactic Acid from Glucose in Ionic Liquid Solvent System

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Preparation of Lactic Acid from Glucose in Ionic Liquid Solvent System J. Cent. South Univ. Technol. (2010) 17: 45−49 DOI: 10.1007/s11771−010−0009−3 Preparation of lactic acid from glucose in ionic liquid solvent system HUANG Jia-ruo(黄嘉若), LI Wen-sheng(李文生), ZHOU Xiao-ping(周小平) College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China © Central South University Press and Springer-Verlag Berlin Heidelberg 2010 Abstract: A new reaction system was designed to economically convert glucose to lactic acid environment-friendly. Hydrophobic ionic liquids were chosen as solvent that can promote the decomposition reaction of glucose, and the catalytic performance of the solid bases was evaluated. Both the reaction temperature and time can affect the yield of lactic acid. A high yield (97%) of lactic acid was achieved under the optimal reaction condition. The 1H NMR spectra and HPLC-MS were used to identify the formation of the lactic acid and variations of ionic liquid. It is found that ionic-liquids have a unique solvent effect for glucose and bases. Water can be used as solvent to extract calcium lactate. This shows a great potential of hydrophobic ionic liquids in the solid bases catalyzed reaction that is limited by the weak solubility of solid bases in organic and water solution. Key words: glucose; lactic acid; ionic liquid; solid base; catalysis 100 ℃. However, in order to obtain lactic acid with a 1 Introduction high yield of 57%, the excess amount of sodium hydroxide must be used. Excessive sodium hydroxide A sustainable future for the chemical industry leads to a number of problems. It is particularly difficult requires feedbacks based on the renewable rather than to separate sodium lactate from sodium hydroxide. JIN steadily depleting resources. Inability to effectively et al [13] reported an improvement for this process transform five or six-carbon carbohydrates into building through adding the hydrogen peroxide to oxidize all blocks derived from the nature is the major barrier organic molecules to formic acid at a yield of 75%. towards this challenging goal. Both fructose and glucose, ZHAO et al [14] suggested that ionic liquid can containing six carbon atoms, are potential feedbacks for dissolve glucose and enhance the acid-catalyzed this purpose, and recently efforts have focused on decomposition of glucose. According to their experiment, converting them to lactic acid, a chemical commodity. the ionic liquid [AMIM]Cl showed higher excellent Some researchers reported similar processes such as solubility to salts and glucose. In this work, the ionic converting glucose into 5-hydroxymethylfurfural (HMF) liquid [OMIM]Cl was used as solvent to enhance the in a two-phase reaction system [1]. It is well known in yield of lactic acid for the glucose decomposition sugar chemistry that the lactic acid is a typical base reaction. catalyzed product from carbohydrates [2−7]. Lactic acid and its derivatives could potentially replace 2 Experimental voluminously consumed petroleum that is currently used to make plastic and fine chemicals [8−9]. A process to Ionic liquids were prepared according to the produce pure lactic acid with a high yield from the procedures described in Refs.[15−16]. Glucose (＞99%, abundant and renewable carbohydrates at low energy mass fraction) was used as a test material because it was cost must be developed before a biorefinery platform can a primary intermediate compound during the conversion be built on the basis of this substrate. Currently lactic of carbohydrates. 1.0 mol/L standardized solution lactic acid is produced by glucose fermentation, and the acid (Alfa Aesar Company, China) was also used for the drawbacks for enzyme catalysis reaction are long quantitative analysis of lactic acid. NaOH (99%) and reaction time and very strict reaction condition [10]. Ca(OH)2 (99%) were selected as alkaline catalysts ONDA et al [11−12] reported a reaction to prepare lactic obtained from China National Medicine Corporation Ltd. acid by catalytic decomposition of glucose with sodium All experiments were carried out in a bath micro- hydroxide. The reaction could be carried out below reactor made up of stainless steel with an internal volume Foundation item: Project(2006BAE02B05) supported by the Key Projects in the National Science and Technology Pillar Program During the 11th Five-year Plan Period; Project(2005CB221406) supported by the National Basic Research Program of China Received date: 2009−03−18; Accepted date: 2009−06−17 Corresponding author: ZHOU Xiao-ping, Professor; Tel: +86−731−88821017; E-mail: [email protected] 46 J. Cent. South Univ. Technol. (2010) 17: 45−49 of 5 mL. The typical experimental procedures were as adding water as extracting agent. So in next experiments, follows: the desired amount of glucose, and the desired C22H43ClN2 was chosen as standard solvent to evaluate solid base catalysts with quantitative ionic liquid the reaction system. prepared in advance were put into a batch heated with a temperature programming oven. After a desired reaction 3.2 Effect of reaction time on preparation of lactic time, the reaction time was defined as the time that acid reactor was kept in the oven. 0.400 g test material was In order to find the best condition for preparation of used in all the experiments. lactic acid, three samples were chosen to evaluate the After the reaction was finished, the samples were influence of reaction time. The reactions were carried out diluted to about 10 mL with de-ionized water. The in a stainless steel bath. The amount of glucose was fixed solution was extracted and filtered, adding hydrochloride at 0.400 g, that of calcium hydroxide was 0.150 g and ＜ acid to adjust pH 7. The samples were injected in that of the ionic liquid C22H43ClN2 was 1.000 g. Because HPLC. HPLC analysis was performed with a Agilent the melting point for the ionic liquid is about 353 K the LC−1200 system equipped with a UV detector (214 nm). samples covered the range from 353 to 373 K. Fig.1 A C−18 column was used to separate the samples for the shows that the sample reacted at 353 K has obviously analysis of lactic acid, with volume ratio of water to different results compared with results of other samples. as mobile phase. The yield of lactic acid is near 5% at first, and as reaction 5׃acetonitrile of 95 1 The product was characterized by H NMR spectra time increases, it does not show a distinct improvement. and WATERS LC−MS. The lactic acid yield was defined After 60 min, the yield still preserves at near 5% and as the percentage of lactic acid mass to initial glucose keeps at this value for further increment of time. For the mass on the carbon-atom basis. experiments at 363 K and 373 K, the lactic acid yields initially increase until 60 min and then decrease for 3 Results and discussion subsequent rise in time. Both of these data show reaction time of 60 min is an advantageous time for obtaining a 3.1 Characteristic of ionic liquid in base-catalyzed high yield of lactic acid. The highest yield at 363 K for glucose decomposition reaction 60 min is about 55%, which is larger than 45% at 373 K. Five kinds of ionic liquids were chosen to evaluate the influences of the ionic liquids. The reactions were carried out at 363 K for 60 min, adding the same amount of glucose (0.400 g), calcium hydroxide (0.150 g), and ionic liquid fixed at 1.000 g. Table 1 demonstrates that all samples have similar yields of lactic acid. The results indicate that ionic liquids act as solvent and have similar solubility for glucose and calcium hydroxide. For entry 4 and entry 5, ionic liquids have a long alkyl chain which makes them hydrophobic. But they still show good solubility for glucose and calcium hydroxide. Entry 4 and entry 5, have the same alkyl ion, but different anions chloride for entry 4 and bromide for entry 5. According to the yields of lactic acid, the effect of anion ion can be excluded. In ionic liquid system, glucose reacts with calcium Fig.1 Influence of reaction time on yield of lactic acid hydroxide to form calcium lactate which is easy to (Reaction condition: 0.400 g glucose, 1.00 g ionic liquid, dissolve in water. Hydrophobic ionic liquid and calcium 0.150 g calcium hydroxide for every samples) hydroxide are facile to separate with calcium lactate by In order to further confirm the influence of temperature on yield of lactic acid and to find the Table 1 Influence of ionic liquids characteristic on yield of advantageous condition for lactic acid production, a lactic acid series of experiments were conducted. In these Test No. Ionic liquid Base Yield/% experiments, the reactions were carried out in the same 1 C H ClN Ca(OH) 49 6 9 2 2 conditions with different reaction temperatures. To 2 C8H15ClN2 Ca(OH)2 51 evaluate the influence of temperatures more clearly 3 C20H39ClN2 Ca(OH)2 55 333 K was chosen as the lowest point, and 464 K was the 4 C22H43ClN2 Ca(OH)2 53 highest for this investigation. At the stage of low 5 C22H43BrN2 Ca(OH)2 51 temperature such as 343 K, calcium hydroxide does not J. Cent. South Univ. Technol. (2010) 17: 45−49 47 show activity. This may imply that ionic liquids are generate HMF, levulinic acid and formic acid. Lactic unable to dissolve both glucose and calcium hydroxide acid is an organic acid which is capable of initiating an under the solid condition. If the temperature is higher acid-catalyzed glucose reaction. So, excessive supply of than their melting point, the yield of lactic acid increases calcium hydroxide may be used to neutralize lactic acid.
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