Of lactic acid

CH3CH(0H)C(0)0Et. A colourless liquid with a pleasant odour, b.p. 154 C. Manufactured by distilling a mixture of ( )-lactic acid, ethanol and benzene in the presence of a little sulphuric or benzenesulphonic acid. It is a solvent for cellulose nitrate and acetate and also for various resins. Used as a lacquer solvent. 

An example of a chiral compound is lactic acid. Two different forms of lactic acid that are mirror images of each other can be defined (Figure 2-69). These two different molecules are called enantiomers. They can be separated, isolated, and characterized experimentally. They are different chemical entities, and some of their properties arc different (c.g., their optical rotation),... 

Figure 2-69. The two enantiomers of lactic acid assignment of R and S configurations to the enantiomers of lactic acid after ranking the four ligands attached to the chiral center according to the Cl P rules (OH > COjH > Me > H).

Iodoform reaction. To 0 5 ml. of lactic acid add 10% NaOH solution until alkaline to litmus. Then add 5 ml. of 10% KI solution and 10 ml. of freshly prepared sodium hypochlorite solution and mix well. A yellow precipitate of iodoform separates out almost immediately in the cold. 

Caustic alkalis. Dilute by drinking much water, followed by vinegar, lemon or orange juice, or solutions of lactic acid or citric acid. Milk may then be given but no emetics. 

IS the oxidation of lactic acid to pyruvic acid by NAD and the enzyme lactic acid coenzyme NAD ... 

Uffelmann s reagent (gives a yellow coloration in the presence of lactic acid) add a ferric chloride solution to a 2% phenol solution until the solution becomes violet in color. 

In addition to alcohoHc fermentation, a malolactic fermentation by certain desirable strains of lactic acid bacteria needs to be considered. Occasionally, wild strains produce off-flavors. Malolactic fermentation is desirable in many red table wines for increased stabiUty, more complex flavor, and sometimes for decreased acidity. Selected strains are often added toward the end of alcohoHc fermentation. AH the malic acid present is converted into lactic acid, with the resultant decrease of acidity and Hberation of carbon dioxide. Obviously this has more effect on the acidity the more malic acid is present, and this is the case in wine from underripe, too-tart grapes. Once malolactic fermentation has occurred, it does not recur unless another susceptible wine is blended. 

Cells of microorganisms have constituted a portion of human food siace ancient times. Yeast-leavened baked products contain the residual nutrients from the yeast cells destroyed duriag bakiag (see Bakery processes and leavening agents). Cultured dairy products, such as yogurt, buttermilk, and sour cream, contain up to lO cells of lactic acid bacteria per gram (19) (see Milk and milkproducts). Other examples of fermented foods consumed siace early times iaclude fermented meats, fish, and soybean products. 

Oxidation of a glycol can lead to a variety of products. Periodic acid quantitatively cleaves 1,2-glycols to aldehydes and is used as an analysis method for glycols (12,13). The oxidation of propylene glycol over Pd/C modified with Pb, Bi, or Te forms a mixture of lactic acid, hydroxyacetone, and pymvic acid (14). Air oxidation of propylene glycol using an electrolytic crystalline silver catalyst yields pymvic aldehyde. 

Physical Properties. Pure, anhydrous lactic acid is a white, crystalline soHd with a low melting poiat. However, it is difficult to prepare the pure anhydrous form of lactic acid generally, it is available as a dilute or concentrated aqueous solution. The properties of lactic acid and its derivatives have been reviewed (6). A few important physical and thermodynamic properties from this reference are summarized ia Table 1. 

Table 1. Physical and Thermodynamic Properties of Lactic Acid...

Many of the physical properties are not affected by the optical composition, with the important exception of the melting poiat of the crystalline acid, which is estimated to be 52.7—52.8°C for either optically pure isomer, whereas the reported melting poiat of the racemic mixture ranges from 17 to 33°C (6). The boiling poiat of anhydrous lactic acid has been reported by several authors it was primarily obtained duriag fractionation of lactic acid from its self-esterification product, the dimer lactoyUactic acid [26811-96-1]. The difference between the boiling poiats of racemic and optically active isomers of lactic acid is probably very small (6). The uv spectra of lactic acid and dilactide [95-96-5] which is the cycHc anhydride from two lactic acid molecules, as expected show no chromophores at wavelengths above 250 nm, and lactic acid and dilactide have extinction coefficients of 28 and 111 at 215 nm and 225 nm, respectively (9,10). The iafrared spectra of lactic acid and its derivatives have been extensively studied and a summary is available (6). 

DUactide (5) exists as three stereoisomers, depending on the configurations of the lactic acid monomer used. The enantiomeric forms whereia the methyl groups are cis are formed from two identical lactic acid molecules, D- or L-, whereas the dilactide formed from a racemic mixture of lactic acid is the opticaUy iaactive meso form, with methyl groups trans. The physical properties of the enantiomeric dilactide differ from those of the meso form (6), as do the properties of the polymers and copolymers produced from the respective dilactide (23,24). 

Polylactide is the generaUy accepted term for highly polymeric poly(lactic acid)s. Such polymers are usuaUy produced by polymerization of dilactide the polymerization of lactic acid as such does not produce high molecular weight polymers. The polymers produced from the enantiomeric lactides are highly crystalline, whereas those from the meso lactide are generaUy amorphous. UsuaUy dilactide from L-lactic acid is preferred as a polymerization feedstock because of the avaUabUity of L-lactic acid by fermentation and for the desirable properties of the polymers for various appUcations (1,25). 

Substitution at the Alcohol Group. Acylation of the OH group by acylating agents such as acid chlorides or anhydrides is one of the important high yielding substitution reactions at the OH group of lactic acid and its functional derivatives. AUphatic, aromatic, and other substituted derivatives can be produced. 

Some of the economic hurdles and process cost centers of this conventional carbohydrate fermentation process, schematically shown in Eigure 1, are in the complex separation steps which are needed to recover and purify the product from the cmde fermentation broths. Eurthermore, approximately a ton of gypsum, CaSO, by-product is produced and needs to be disposed of for every ton of lactic acid produced by the conventional fermentation and recovery process (30). These factors have made large-scale production by this conventional route economically and ecologically unattractive. 

The fermentation-derived food-grade product is sold in 50, 80, and 88% concentrations the other grades are available in 50 and 88% concentrations. The food-grade product meets the Vood Chemicals Codex III and the pharmaceutical grade meets the FCC and the United States Pharmacopoeia XK specifications (7). Other lactic acid derivatives such as salts and esters are also available in weU-estabhshed product specifications. Standard analytical methods such as titration and Hquid chromatography can be used to determine lactic acid, and other gravimetric and specific tests are used to detect impurities for the product specifications. A standard titration method neutralizes the acid with sodium hydroxide and then back-titrates the acid. An older standard quantitative method for determination of lactic acid was based on oxidation by potassium permanganate to acetaldehyde, which is absorbed in sodium bisulfite and titrated iodometricaHy. 

Uses. Currentiy, the principal use of lactic acid is in food and food-related applications, which in the United States accounts for approximately 85% of the demand. The rest ( 15%) of the uses are for nonfood industrial applications. The expected advent of the production of low cost lactic acid in high volume can open new applications for lactic acid and its derivatives, because it is a versatile molecule that can be converted to a wide range of industrial chemicals or polymer feedstocks (1,6,20). 

Biacetyl is produced by the dehydrogenation of 2,3-butanediol with a copper catalyst (290,291). Prior to the availabiUty of 2,3-butanediol, biacetyl was prepared by the nitrosation of methyl ethyl ketone and the hydrolysis of the resultant oxime. Other commercial routes include passing vinylacetylene into a solution of mercuric sulfate in sulfuric acid and decomposing the insoluble product with dilute hydrochloric acid (292), by the reaction of acetal with formaldehyde (293), by the acid-cataly2ed condensation of 1-hydroxyacetone with formaldehyde (294), and by fermentation of lactic acid bacterium (295—297). Acetoin [513-86-0] (3-hydroxy-2-butanone) is also coproduced in lactic acid fermentation. 

Yogurt is manufactured by procedures similar to buttermilk. Milk with a fat content of 1—5% and soHds-not-fat (SNF) content of 11—14% is heated to ca 82°C and held for 30 minutes. After homogenization the milk is cooled to 43—46°C and inoculated with 2% culture. The product is incubated at 43°C for three hours in a vat or in the final container. The yogurt is cooled and held at <4.4° C. The cooled product should have a titratable acidity of not less than 0.9% and a pH of 4.3—4.4. The titratable acidity is expressed in terms of percentage of lactic acid [598-82-3] which is deterrnined by the amount of 0.1 AiNaOH/100 mL required to neutralize the substance. Thus 10 mL of 0.1 AiNaOH represents 0.10% acidity. Yogurts with less than 2% fat are popular. Fmit-flavored yogurts are also common in which 30—50 g of fmit are placed in the carton before or with the yogurt. 

In the first step, propylene is introduced at 10—40°C into nitric acid, the concentration of which is kept at 50—75 wt % and molar ratio to propylene at 0.01—0.5, and converted into a-nitratolactic acid and lactic acid. a-Nitratolactic acid is oxidized by oxygen in the second step in the presence of a catalyst at 45—100°C to produce oxahc acid dihydrate. The overall yield based on propylene is greater than 90% and the conversion of propylene, 77.5%. The outhne of the process is shown in Figure 2. The RhcJ)ne-Poulenc process can be characterized by the coproduction of lactic acid. 

Eusarium monilijorme etc M. ammoniaphilum Arghydroxamate addition of lactic acid is effective 60... 

Polylactic acid, also known as polylactide, is prepared from the cycHc diester of lactic acid (lactide) by ring-opening addition polymerization, as shown below ... 

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