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Lactic acid structure

Lactic acid
  • CAS：50-21-5
  • MW:90.078
  • MF：C3H6O3
Lactic acid (2-hydroxypropionic acid, CH3-CHOH-COOH) is the most widelyoccurring organic acid in nature. Due to its chiral a-carbon atom, lactic acid (LA)has two enantiomeric forms. Of these, L-(+)-lactic acid is more important in food and pharmaceutical industries because humans have only L-lactatedehydrogenase. The chemical behavior of lactic acid is mostly determinedby the two functional groups. Besides the acidic character in aqueousmedium, the bifunctionality (a terminal carboxylic acid and a hydroxyl group)allows lactic acid molecules to form ‘‘interesters’’ such as the cyclic dimers, thetrimers, or longer lactic acid oligomers.After its first isolation by the Swedish chemist Scheel in 1780 from sour milk,lactic acid has been produced commercially since the 1880s in the United Statesand later in Europe. Worldwide, lactic acid production was approximately250,000 metric tons per year in 2012 and is expected to reach 330,000metric tons by the year 2015, with an average price of 1.25 US$ perkilogram in 2013 (food grade, 80–85 % purity). Approximately 85 % of the demand for LA is from the food industry. Theprimary use of lactic acid is as a pH-adjusting agent in the beverage sector and as apreservative in the food industry. It is included in the Generally Recognized asSafe (GRAS) by the U.S. Food and Drug Administration [158] as a food ingredientand was deemed safe by the European Food Safety Authority as well [159]. Theacceptable daily intake for LA was defined by the Joint FAO/WHO ExpertCommittee on Food Additives as ‘‘not limited,’’ and it is also supported by theScientific Committee of Food. In recent decades, the consumption of lactic acid due to its novel applicationshas grown quite rapidly, by 19 % per year. Nonfood use of lactic acid for polymer production contributes to this growth. Biodegradable polylactic acid isconsidered to be an environmentally friendly alternative to other plastics frompetroleum. It is used in various fields, including drug delivery systems,medical devices, fibers, and packaging materials. Lactic acid can be produced via chemical synthesis or carbohydrate fermentation.The chemical route has various issues, including toxic raw materials, lowconversion rates, and especially the inability to produce the optically pure isomer.Therefore, approximately 90 % of lactic acid worldwide is produced by biotechnologicalprocesses, namely fermentations using renewable resources, whichis relatively fast, economical, and able to supply selectively one or two stereoisomersof lactic acid. View more+
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1. Names and Identifiers
1.1 Name
Lactic acid
1.2 Synonyms
1H-Pyrrolo[2,3-b]pyridine-3-acetic acid, 5-bromo-a-oxo-; 2-Hydroxy-2-methylacetic acid; 2-Hydroxypropionic acid; DL-ALPHA-HYDROXYPROPIONIC ACID; DL-Lactic acid; dl-lactic acid, acs; EINECS 200-018-0; FEMA 2611; Lactic; LACTICACID,RACEMIC,USP; MFCD00004520;
1.3 CAS No.
50-21-5
1.4 CID
612
1.5 EINECS
200-018-0; 295-890-2; 209-954-4
1.6 Molecular Formula
C3H6O3
1.7 Inchi
InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)
1.8 InChkey
JVTAAEKCZFNVCJ-UHFFFAOYSA-N
1.9 Canonical Smiles
CC(C(=O)O)O
1.10 Isomers Smiles
CC(C(=O)O)O
2. Properties
2.1 Vapour pressure
0.62 (vs air)
2.2 Viscosity
Viscosities of aqueous lactic acid at 25 °C: 1.042 mPa s (6.29 wt%), 1.752 mPa s (25.02 wt%), 4.68 mPa s (54.94 wt%), 36.9 mPa s (88.60 wt%)
2.3 VaporDensity
0.62 (vs air)
2.4 Appearance
Colorless to yellow liquid
2.5 Storage
Lactic acid is hygroscopic and will form condensation productssuch as polylactic acids on contact with water. The equilibriumbetween the polylactic acids and lactic acid is dependent onconcentration and temperature. At elevated temperatures lactic acidwill form lactide, which is readily hydrolyzed back to lactic acid.Lactic acid should be stored in a well-closed container in a cool,dry place.
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2.6 Chemical Properties
Lactic acid consists of a mixture of 2-hydroxypropionic acid, itscondensation products, such as lactoyllactic acid and otherpolylactic acids, and water. It is usually in the form of the racemate,(RS)-lactic acid, but in some cases the (S)-(+)-isomer is predominant.Lactic acid is a practically odorless, colorless or slightly yellowcolored,viscous, hygroscopic, nonvolatile liquid.
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2.7 Color/Form
Crystals
Yellow to colorless crystals or syrupy 50% liquid
2.8 Corrosivity
Caustic in concentrated solutions
2.9 Decomposition
When heated to decompositionit emits acrid smoke and irritating fumes.
2.10 Heat of Combustion
3615 cal/kg
2.11 Odor
Odorless
2.12 PH
The pH of a 10 wt% aqueous solution of lactic acid is 1.75
2.13 pKa
3.08(at 100℃)
2.14 Water Solubility
Solubility in water: miscible
2.15 Spectral Properties
Index of refraction = 1.4392 at 20 deg C
SADTLER REF NUMBER: 5338 (IR, PRISM)
IR: 467 (Sadtler Research Laboratories IR Grating Collection)
1H NMR: 9265 (Sadtler Research Laboratories Spectral Collection)
MASS: 176 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
2.16 Stability
Stable. Combustible. Incompatible with strong oxidizing agents.
2.17 StorageTemp
2-8°C
3. Use and Manufacturing
3.1 Definition
ChEBI: A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.
3.2 Description

Lactic acid consists of a mixture of 2-hydroxypropionic acid, its condensation products, such as lactoyllactic acid and other polylactic acids, and water. It is usually in the form of the racemate, (RS)-lactic acid, but in some cases the (S)-(+)-isomer is predominant.
Lactic acid is a practically odorless, colorless or slightly yellowcolored, viscous, hygroscopic, nonvolatile liquid. Lactic acid, CH3CHOHCOOH, also known as 2-hydroxypropanoic acid, is a hygroscopic liquid that exists in thr

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3.3 General Description
A colorless to yellow odorless syrupy liquid. Corrosive to metals and tissue. Used to make cultured dairy products, as a food preservative, and to make chemicals.
3.4 Methods of Manufacturing
1. Starch raw materials, molasses, starch sugar as raw materials, after saccharification with the appropriate acid lactic acid bacteria or Bacillus in the appropriate conditions of fermentation, the calcium carbonate and precipitation, and then dilute sulfuric acid to lactic acid , And then refined after lactic acid products can be obtained. Starch saccharification ↓ saccharification enzyme ↓ lactic acid bacteria and pressure filtration concentrated cooling acidification bleaching ↓ activated carbon ↓ sulfuric acid pumping vacuum concentration cation exchange anion exchange vacuum concentration decolorization filter finished product purification method: lactic acid has a strong hygroscopicity, concentrated partial lactic acid Acid anhydride, heating itself prone to esterification reaction. Therefore, even if distilled under reduced pressure, it is difficult to obtain pure product. The fraction was fractionated at 13.3 Pa, and the distillate was dissolved with a mixture of equal amounts of ether and isopropyl ether to cool the crystals at an ice salt temperature. Filtered and then repeated twice. It can also be crystallized at the dry ice temperature. The solvent may also be used in a mixed solvent of equal amounts of benzene and diethyl ether containing 5% petroleum ether (b.p. 60 to 80C).
2. There are three methods of producing lactic acid in industry, fermentation, acetaldehyde and acrylonitrile. The most widely used is the fermentation method, is the raw material containing starch sucrose, beet sugar, molasses or grain starch as raw material, saccharification access lactic acid bacteria, ph = 5, 49 ℃ fermentation 3 to 4 days, with calcium carbonate And, while hot filter, refined with calcium lactate. And then acidified with sulfuric acid, filtered, the filtrate concentrated, decolorization, impurity that product. 3 synthesis of chemical synthesis of acetaldehyde and acrylonitrile method, the resulting lactic acid DL. Lactic acid.
(1) acetaldehyde method to acetaldehyde and hydrocyanic acid as raw materials to produce milk, the hydrolysis of crude lactic acid, crude lactic acid by ethanol esterification and then hydrolysis of lactic acid: acetaldehyde and cold hydrocyanic acid into the reaction And then add the water and sulfuric acid catalyzed hydrolysis of lactic acid; ethanol after esterification distillation of ethyl lactate; finally sent to the concentration of concentrated decomposition of refined milk lactic acid.
(2) Acrylonitrile acrylonitrile hydrolysis of crude lactic acid, and then esterified by methanol after hydrolysis of lactic acid: acrylonitrile sent to the reactor, in the catalytic hydrolysis of sulfuric acid to produce a mixture of lactic acid and ammonium sulfate. The mixture into the esterification reactor and methanol esterification, separation of ammonium sulfate, the crude ester to send distillation tower, the bottom of the fine ester. Refined ester distillation tower, heating decomposition, was dilute lactic acid. Finally, the product is concentrated by vacuum.
4. Tobacco: BU, 26. In the food industry by the glucose, starch, milk fermentation preparation; acetaldehyde and hydrocyanic acid reaction to produce cyanoethanol, and then hydrolyzed to produce crude lactic acid, vinegar lactic acid into ethyl lactate, and then hydrolyzed to pure lactic acid.
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3.5 Usage
Prostaglandin E1 analogue
4. Safety and Handling
4.1 Exposure Standards and Regulations
Substance added directly to human food affirmed as generally recognized as safe (GRAS).
Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: lactic acid is included in digestive drug products.
Lactic acid used as a general purpose food additive inanimal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.
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4.2 Octanol/Water Partition Coefficient
log Kow = -0.72
4.3 Fire Hazard
Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
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4.4 Cleanup Methods
Collect leaking liquid in sealable containers. Cautiously neutralize spilled liquid with weak alkaline solution, e.g. disodium carbonate. Then wash away with plenty of water.
4.5 DisposalMethods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
The following wastewater treatment technology has been investigated for lactic acid: Concentration process: Biological treatment.
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4.6 Formulations/Preparations
Lactic acid is available in edible grades (22-44% concn) and in 50-80% concn for plastic and usp grades.
Grade: Technical, 22% and 44%; food 50 to 80%; plastic 50 to 80%; USP (85-90%); CP; FCC
Has one asymmetric carbon and two enantiomorphic isomers. The commercial form is a racemic mixture.
COMMERCIAL LACTIC ACID GRADES INCLUDE 88% U.S.P. GRADE, 88 AND 50% TECHNICAL, AND 50% FOOD GRADE
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4.7 Incompatibilities
Incompatible with oxidizing agents, iodides, and albumin. Reactsviolently with hydrofluoric acid and nitric acid.
4.8 Protective Equipment and Clothing
In general, on the basis of animal studies and human use, the most significant effects caused by exposure to lactate esters are respiratory, dermal, and ocular irritation. Irritation may be associated with the formation of lactic acid, a product of hydrolysis of lactate esters. /Hydroxyal esters: lactates/
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4.9 Reactivities and Incompatibilities
A mixture of 5 parts lactic acid, 5 parts nitric acid, 2 parts water, and 1 part hydrofluoric acid being stored in a plastic bottle ruptured with explosive force. /Nitric acid/
Mixtures of /lactic acid, hydrofluoric acid and nitric acid/, used as metal polishing solutions, are unstable and should not be stored. Lactic acid and nitric acid react autocatalytically after a quiescent period, attaining a temperature of about 90 deg C with vigorous gas evolution after about 12 hr. Prepare freshly, discard after use and handle carefully. /Nitric acid/
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4.10 Skin, Eye, and Respiratory Irritations
In general, on the basis of animal studies and human use, the most significant effects caused by exposure to lactate esters are respiratory, dermal, and ocular irritation. Irritation may be associated with the formation of lactic acid, a product of hydrolysis of lactate esters. /Hydroxyal esters: lactates/
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4.11 Safety

Safety information of 3-Iodo-4-methylaniline (CAS NO.35944-64-0):
Hazard Codes  ToxicT
Risk Statements 
25  Toxic if swallowed
41  Risk of serious damage to eyes
43  May cause sensitization by skin contact
Safety Statements 
26  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37/39  Wear suitable protective clothing, gloves and eye/face protection
45  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS  XU7700000
HazardClass  6.1
PackingGroup  III

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4.12 Sensitive
Light Sensitive
4.13 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 2400ug/kg (2.4mg/kg)   Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Serious eye damage, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H315 Causes skin irritation

H318 Causes serious eye damage
Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

P302+P352 IF ON SKIN: Wash with plenty of water/...

P321 Specific treatment (see ... on this label).

P332+P313 If skin irritation occurs: Get medical advice/attention.

P362+P364 Take off contaminated clothing and wash it before reuse.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P310 Immediately call a POISON CENTER/doctor/\u2026

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum
13C NMR : in DMSO-d6  
13C NMR : Predict  
1H NMR : in DMSO-d6  
1H NMR : Predict  
IR : liquid film  
Raman : 4880 A,200 M,liquid  
7. Synthesis Route
50-21-5Total: 4 Synthesis Route
 
113-24-6
113-24-6 285 Suppliers
 
50-21-5
50-21-5 493 Suppliers
 
50-21-5
50-21-5 493 Suppliers
 
41656-56-8
41656-56-8
 
50-21-5
50-21-5 493 Suppliers
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8. Precursor and Product
precursor:
81388-05-8
81388-05-8
113-24-6
113-24-6
41656-56-8
41656-56-8
81388-02-5
81388-02-5
product:
7474-05-7
7474-05-7
9. Computed Properties
10.Other Information
Merck
14,5336
BRN
1209341
Usage
It is used most commonly by athletes to describe the intense pain felt during exhaustive exercise. Used to make cultured dairy products, as a food preservative, and to make chemicals. Useful for the creation of highly aligned electrospun poly-L-lactic acid fibers for nerve regeneration applications. Poly(lactic acid) nanocomposites with various organoclays shows useful application for gas permeability.
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Usage
DL-Lactic acid is used to produce serial products or widely used in food, vintage, beverage, drugs, polymerization, textile, leather, tobacco, feed, plastic chemicals, pesticide, polymer solution and other industry. Lactic acid is also used as an acidifying agent.
Description
Lactic acid (2-hydroxypropionic acid, CH3-CHOH-COOH) is the most widely occurring organic acid in nature. Due to its chiral a-carbon atom, lactic acid (LA) has two enantiomeric forms. Of these, L-(+)-lactic acid is more important in food and pharmaceutical industries because humans have only L-lactate dehydrogenase. The chemical behavior of lactic acid is mostly determined by the two functional groups. Besides the acidic character in aqueous medium, the bifunctionality (a terminal carboxylic acid and a hydroxyl group) allows lactic acid molecules to form ‘‘interesters’’ such as the cyclic dimers, the trimers, or longer lactic acid oligomers.
After its first isolation by the Swedish chemist Scheel in 1780 from sour milk, lactic acid has been produced commercially since the 1880s in the United States and later in Europe. Worldwide, lactic acid production was approximately 250,000 metric tons per year in 2012 and is expected to reach 330,000 metric tons by the year 2015, with an average price of 1.25 US$ per kilogram in 2013 (food grade, 80–85 % purity).
Approximately 85 % of the demand for LA is from the food industry. The primary use of lactic acid is as a pH-adjusting agent in the beverage sector and as a preservative in the food industry. It is included in the Generally Recognized as Safe (GRAS) by the U.S. Food and Drug Administration [158] as a food ingredient and was deemed safe by the European Food Safety Authority as well [159]. The acceptable daily intake for LA was defined by the Joint FAO/WHO Expert Committee on Food Additives as ‘‘not limited,’’ and it is also supported by the Scientific Committee of Food.
In recent decades, the consumption of lactic acid due to its novel applications has grown quite rapidly, by 19 % per year. Nonfood use of lactic acid for polymer production contributes to this growth. Biodegradable polylactic acid is considered to be an environmentally friendly alternative to other plastics from petroleum. It is used in various fields, including drug delivery systems, medical devices, fibers, and packaging materials.
Lactic acid can be produced via chemical synthesis or carbohydrate fermentation. The chemical route has various issues, including toxic raw materials, low conversion rates, and especially the inability to produce the optically pure isomer. Therefore, approximately 90 % of lactic acid worldwide is produced by biotechnological processes, namely fermentations using renewable resources, which is relatively fast, economical, and able to supply selectively one or two stereoisomers of lactic acid.
View all
Chemical Properties
Lactic acid consists of a mixture of 2-hydroxypropionic acid, its condensation products, such as lactoyllactic acid and other polylactic acids, and water. It is usually in the form of the racemate, (RS)-lactic acid, but in some cases the (S)-(+)-isomer is predominant.
Lactic acid is a practically odorless, colorless or slightly yellowcolored, viscous, hygroscopic, nonvolatile liquid.
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Chemical Properties
Lactic acid, CH3CHOHCOOH, also known as 2-hydroxypropanoic acid, is a hygroscopic liquid that exists in three isometric forms. I-lactic acid is found in blood and animal tissue as a product of glucose and glycogen metabolism. d-Iactic acid is obtained by fermentation of sucrose (corn refining), The racemic mixture is present in foods prepared by bacterial fermentation or prepared synthetically. Lactic acid is soluble in water,alcohol,and ether. It is used as a solvent, in manufacturing confectionery, and in medicine.
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Chemical Properties
A colorless or yellowish, nearly odorless, syrupy liquid consisting of a mixture of lactic acid (C3H6O3) and lactic acid lactate (C6H10O5). It is obtained by the lactic fermentation of sugars or is prepared synthetically. The commercial product is the racemic form. It is usually available in solutions containing the equivalent of from 50% to 90% lactic acid. It is hygroscopic, and when concentrated by boiling, the acid condenses to form lactic acid lactate, 2-(lactoyloxy)propanoic acid, which on dilution and heat ing hydrolyzes to lactic acid. It is miscible with water and with alcohol.
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Chemical Properties
Lactic acid is odorless. It consists of a mixture of lactic acid (C3H6O3) and lactic acid lactate (C6H10O5). The commercial product is the racemic form. It is usually available in solutions containing 50 to 90% lactic acid.
Occurrence
Reported found in Papaver somniferum L.; it is a constituent of wine and sour milk; the two optically active isomers are found in muscular tissues and are formed by the action of lactic acid–producing bacteria in several fermentation processes. Also reported found in guava, grapes, melon, wheat bread, cheeses, yogurt, milk, cream, buttermilk, egg, cooked beef, cognac, cider, sherry, grape wine, beer, grape brandy, whiskey, cocoa, coffee, tea, mango, sake, wort, dried, bonito, cassava, Bourbon vanilla, chicory root, Cape gooseberry and cherimoya.
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Uses
Prostaglandin E1 analogue
Uses
lactic acid (sodium lactate) is a multi-purpose ingredient used as a preservative, exfoliant, moisturizer, and to provide acidity to a formulation. In the body, lactic acid is found in the blood and muscle tissue as a product of the metabolism of glucose and glycogen. It is also a component of the skin’s natural moisturizing factor. Lactic acid has better water intake than glycerin. Studies indicate an ability to increase the water-retention capacity of the stratum corneum. They also show that the pliability of the stratum corneum layer is closely related to the absorption of lactic acid; that is, the greater the amount of absorbed lactic acid, the more pliable the stratum corneum layer. Researchers report that continuous use of preparations formulated with lactic acid in concentrations ranging between 5 and 12 percent provided a mild to moderate improvement in fine wrinkling and promote softer, smoother skin. Its exfoliating properties can help in the process of removing excess pigment from the surface of the skin, as well as improving skin texture and feel. Lactic acid is an alpha hydroxy acid occurring in sour milk and other lesser-known sources, such as beer, pickles, and foods made through a process of bacterial fermentation. It is caustic when applied to the skin in highly concentrated solutions.
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Uses
Lactic Acid is an acidulant that is a natural organic acid present in milk, meat, and beer, but is normally associated with milk. it is a syrupy liquid available as 50 and 88% aqueous solutions, and is mis- cible in water and alcohol. it is heat stable, nonvolatile, and has a smooth, milk acid taste. it functions as a flavor agent, preservative, and acidity adjuster in foods. it is used in spanish olives to prevent spoilage and provide flavor, in dry egg powder to improve disper- sion and whipping properties, in cheese spreads, and in salad dress- ing mixes.
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Definition
ChEBI: A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.
Production Methods
Lactic acid is prepared by the fermentation of carbohydrates, such as glucose, sucrose, and lactose, with Bacillus acidi lacti or related microorganisms. On a commercial scale, whey, corn starch, potatoes, or molasses are used as a source of carbohydrate. Lactic acid may also be prepared synthetically by the reaction between acetaldehyde and carbon monoxide at 130–200°C under high pressure, or by the hydrolysis of hexoses with sodium hydroxide.
Lactic acid prepared by the fermentation of sugars is levorotatory; lactic acid prepared synthetically is racemic. However, lactic acid prepared by fermentation becomes dextrorotatory on dilution with water owing to the hydrolysis of (R)-lactic acid lactate to (S)- lactic acid.
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Biotechnological Production
Lactic acid is produced biotechnologically in general by fermentation of lactic acid bacteria. More information about this process and new trends are described later in this chapter.
Taste threshold values
Taste characteristics at 20 ppm: acidic sour creamy, dairylike with a fruity mango nuance
General Description
A colorless to yellow odorless syrupy liquid. Corrosive to metals and tissue. Used to make cultured dairy products, as a food preservative, and to make chemicals.
Air & Water Reactions
Soluble in water.
Reactivity Profile
Lactic acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Lactic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions. Slowly corrodes most metals [USCG, 1999].
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Health Hazard
Inhalation of mist causes coughing and irritation of mucous membranes. Ingestion, even of diluted preparations, has a corrosive effect on the esophagus and stomach. Contact with more concentrated solutions can cause severe burns of skin or eye.
Fire Hazard
Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
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Pharmaceutical Applications
Lactic acid is used in beverages, foods, cosmetics, and pharmaceuticals as an acidifying agent and acidulant.
In topical formulations, particularly cosmetics, it is used for its softening and conditioning effect on the skin. Lactic acid may also be used in the production of biodegradable polymers and microspheres, such as poly(D-lactic acid), used in drug delivery systems.
Lactic acid is also used as a food preservative. Therapeutically, lactic acid is used in injections, in the form of lactate, as a source of bicarbonate for the treatment of metabolic acidosis; as a spermicidal agent; in pessaries for the treatment of leukorrhea; in infant feeds; and in topical formulations for the treatment of warts.
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Industrial uses
lactic acid showed good depressing effect on hornblende, pyroxene and biotite during flotation of hematite and ilmenite minerals.
Biochem/physiol Actions
In animals, lactic acid is a metabolic compound produced by proliferating cells and during anaerobic conditions such as strenuous exercise. Lactic acid can be oxidized back to pyruvate or converted to glucose via gluconeogenesis. Lactic acid is preferentially metabolized by neurons in several mammal species and during early brain development.
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Safety
Lactic acid occurs in appreciable quantities in the body as an end product of the anaerobic metabolism of carbohydrates and, while harmful in the concentrated form , can be considered nontoxic at the levels at which it is used as an excipient. A 1% v/v solution, for example, is harmless when applied to the skin.
There is evidence that neonates have difficulty in metabolizing (R)-lactic acid, and this isomer and the racemate should therefore not be used in foods intended for infants aged less than 3 months old.
There is no evidence that lactic acid is carcinogenic, teratogenic, or mutagenic.
LD50 (guinea pig, oral): 1.81 g/kg
LD50 (mouse, oral): 4.88 g/kg
LD50 (mouse, SC): 4.5 g/kg
LD50 (rat, oral): 3.73 g/kg
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storage
Lactic acid is hygroscopic and will form condensation products such as polylactic acids on contact with water. The equilibrium between the polylactic acids and lactic acid is dependent on concentration and temperature. At elevated temperatures lactic acid will form lactide, which is readily hydrolyzed back to lactic acid.
Lactic acid should be stored in a well-closed container in a cool, dry place.
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Incompatibilities
Incompatible with oxidizing agents, iodides, and albumin. Reacts violently with hydrofluoric acid and nitric acid.
Regulatory Status
GRAS listed. Accepted for use as a food additive in Europe. Included in the FDA Inactive Ingredients Database (IM, IV, and SC injections; oral syrups and tablets; topical and vaginal preparations). Included in medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.
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Storage Conditions
1. Starch raw materials, molasses, starch sugar as raw materials, after saccharification with the appropriate acid lactic acid bacteria or Bacillus in the appropriate conditions of fermentation, the calcium carbonate and precipitation, and then dilute sulfuric acid to lactic acid , And then refined after lactic acid products can be obtained. Starch saccharification ↓ saccharification enzyme ↓ lactic acid bacteria and pressure filtration concentrated cooling acidification bleaching ↓ activated carbon ↓ sulfuric acid pumping vacuum concentration cation exchange anion exchange vacuum concentration decolorization filter finished product purification method: lactic acid has a strong hygroscopicity, concentrated partial lactic acid Acid anhydride, heating itself prone to esterification reaction. Therefore, even if distilled under reduced pressure, it is difficult to obtain pure product. The fraction was fractionated at 13.3 Pa, and the distillate was dissolved with a mixture of equal amounts of ether and isopropyl ether to cool the crystals at an ice salt temperature. Filtered and then repeated twice. It can also be crystallized at the dry ice temperature. The solvent may also be used in a mixed solvent of equal amounts of benzene and diethyl ether containing 5% petroleum ether (b.p. 60 to 80C).
2. There are three methods of producing lactic acid in industry, fermentation, acetaldehyde and acrylonitrile. The most widely used is the fermentation method, is the raw material containing starch sucrose, beet sugar, molasses or grain starch as raw material, saccharification access lactic acid bacteria, ph = 5, 49 ℃ fermentation 3 to 4 days, with calcium carbonate And, while hot filter, refined with calcium lactate. And then acidified with sulfuric acid, filtered, the filtrate concentrated, decolorization, impurity that product. 3 synthesis of chemical synthesis of acetaldehyde and acrylonitrile method, the resulting lactic acid DL. Lactic acid.
(1) acetaldehyde method to acetaldehyde and hydrocyanic acid as raw materials to produce milk, the hydrolysis of crude lactic acid, crude lactic acid by ethanol esterification and then hydrolysis of lactic acid: acetaldehyde and cold hydrocyanic acid into the reaction And then add the water and sulfuric acid catalyzed hydrolysis of lactic acid; ethanol after esterification distillation of ethyl lactate; finally sent to the concentration of concentrated decomposition of refined milk lactic acid.
(2) Acrylonitrile acrylonitrile hydrolysis of crude lactic acid, and then esterified by methanol after hydrolysis of lactic acid: acrylonitrile sent to the reactor, in the catalytic hydrolysis of sulfuric acid to produce a mixture of lactic acid and ammonium sulfate. The mixture into the esterification reactor and methanol esterification, separation of ammonium sulfate, the crude ester to send distillation tower, the bottom of the fine ester. Refined ester distillation tower, heating decomposition, was dilute lactic acid. Finally, the product is concentrated by vacuum.
4. Tobacco: BU, 26. In the food industry by the glucose, starch, milk fermentation preparation; acetaldehyde and hydrocyanic acid reaction to produce cyanoethanol, and then hydrolyzed to produce crude lactic acid, vinegar lactic acid into ethyl lactate, and then hydrolyzed to pure lactic acid.
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Storage features
Separated from strong bases.
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12. Related Questions
What are the Uses and Production Methods of Lactic Acid?Introduction Lactic acid, also known as 2-hydroxypropionic acid (CH3CHOHCOOH), was first commercially manufactured in the United States in 1883 through lactic acid bacterial fermentation of sugar subs..
Lactic Acid vs. Glycolic Acid: How to Choose the Right One for Your Skin?Lactic acid and glycolic acid are two popular skincare chemicals that offer numerous benefits for your skin. In this article, we will explore the differences between lactic acid and glycolic acid and ..
Is Lactic Acid in Food Safe and Beneficial for Your Health?In our daily lives, lactic acid in food is quite common. It's a chemical that bacteria naturally make when they ferment food. Despite doubts about its safety, this ubiquitous substance provides a vari..
Why is Lactic Acid Produced in Muscle Cells and Red Blood Cells? Lactic acid is a byproduct of glycolysis, an energy system that creates ATP energy in the absence of oxygen in muscle cells. This occurs during high-intensity exercise when the body cannot take in en..
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4. Safety and Handling
5. Msds
6. NMR Spectrum
7. Synthesis Route
8. Precursor and Product
9. Computational chemical data
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