Beer Encyclopedia
Acetic acid
Nomenclature
The trivial name acetic acid acetum derives from the Latin word for vinegar, and relates to the word acid itself. The synonym ethanoic acid is built according to the replacement of the IUPAC nomenclature.
glacial acetic acid is a trivial name for anhydrous acetic acid. As the German name Eisessig (literally, ice vinegar), the name comes from the crystals as ice is formed slightly below an ambient temperature of 16.7 C (62 F).
The most common abbreviation for acetic acid HOAc where Ac means acetyl group CH3 (= O). In the context of acid-base reactions the abbreviation HAC is often used in place of Ac means the anion acetate (CH3COO, abbreviated OC), although this use is considered by many as misleading. In any case, the CA should not be confused with the abbreviation of the chemical element actinium. Acetic acid has the empirical formula CH2O. Highlight the role of active hydrogen in the formation of the sodium acetate salt, some people write the molecular formula as C2H4O2 or HC2H3O2. To better reflect its structure, Acetic acid is often written as CH3-CO 2-H, CH3COOH, or CH3CO2H. The ion resulting from loss of H + from acetic acid, acetate anion. Acetate name may also refer to a salt containing this anion, or ester of acetic acid.
History
Vinegar was known, in the early civilization as the natural result of exposure to air of beer and wine, such as acetic acid bacteria, is present worldwide. The acetic acid use alchemy extends to the third century C., when the Greek philosopher Theophrastus described how vinegar works on metals to produce pigments useful in the art, including white lead (lead carbonate) and verdigris, a green mixture of copper salts including copper (II) acetate. The ancient Romans cooked soured wine in lead pots to produce a highly sweet syrup called sapa. Sapa was rich in lead acetate, a sweet substance also called sugar of lead or sugar Saturn, which contributed to lead poisoning among the Roman aristocracy.
In the eighth century the Muslim alchemist Jabir Ibn Hayyan (Geber) was the first acid concentrated acetic vinegar through distillation. In the Renaissance, glacial acetic acid was prepared by the dry distillation of certain acetates metal (most notably of copper (II) acetate). The 16th century German alchemist Andreas Libavius describes this procedure, and compared the glacial acetic acid produced by this means to vinegar. The presence of water in vinegar has such a profound effect on the properties of acetic acid that centuries chemists believed that the acid glacial acetic acid in vinegar is different both substances. The French chemist Pierre Adet them proved to be identical.
acetic acid crystallized
In 1847 the German chemist Hermann Kolbe synthesized acetic acid from inorganic materials, for the first time. This reaction sequence consisted in the chlorination of carbon disulfide, carbon tetrachloride, followed by pyrolysis and chlorination Tetrachloroethylene aqueous trichloroacetic acid, concluded with the electrolytic reduction of acetic acid.
In 1910 most glacial acetic acid was obtained from the "Liquor pyroligneous" distillation of wood. Acetic acid was isolated from this by treatment with milk of lime, and the resulting calcium acetate is acidified and then with sulfuric acid to recover acetic acid. At that time Germany produced 10,000 tons of glacial acetic acid, about 30% of which was used in the manufacture of indigo dye.
Chemical properties
Acetic acid crystals
Hydrogen (H) atom in the carboxyl group (OOH), carboxylic acids such as acetic acid may be released as an ion H + (protons), giving them their acidic character. Acetic acid weak indeed monoprotic acid in aqueous solution with a pKa value of 4.75. Its conjugate base acetate (CH3COO). A 1.0 M solution (on the concentration of domestic vinegar) has a pH of 2.4, indicating that only 0.4% acetic acid molecules dissociate.
Cyclic Dimer acetic acid; dotted lines represent hydrogen bonds
The crystal structure of acetic acid shows that the molecules are paired dimers connected by hydrogen bonds. The dimers can also be detected in the steam at 120 C. Also present in the liquid phase in dilute solutions in solvents of hydrogen bonds, and to some extent in pure acetic acid, but are hindered by hydrogen bonding solvents. The dissociation enthalpy 65.066.0 estimated dimer in kJ / mol, and entropy in the dissociation 154 157 J mol1 K1. Dimerization This behavior is shared by other lower acids Carboxylic.
Liquid acetic acid is a hydrophilic (polar) protic solvent, similar to ethanol and water. With a moderate dielectric (Dielectric constant) 6.2, it can dissolve not only polar compounds such as inorganic salts and sugars, but also non-polar compounds, such as oils and elements such as sulfur and iodine. It mixes easily with other polar and nonpolar solvents such as water, chloroform and hexane. With the higher alkanes (from octane) of acetic acid is not completely more miscible. The gap is growing more mixing capacity of n-alkanes. This dissolving property and miscibility of acetic acid makes a chemical widely industrial use.
Chemical reactions
Acetic acid is corrosive to metals such as iron, magnesium and zinc, hydrogen gas and forming salts metal called acetates. Aluminium, when exposed to oxygen, forms a thin layer of aluminum oxide on its surface that is relatively resistant to acid, this allows aluminum tanks for the transport of acetic acid. Metal acetates can also be prepared from acetic acid and a suitable base, as in the popular "vinegar baking soda + "reaction. With the notable exception of chromium (II) acetate, almost all acetates are soluble in water.
Mg (s) + 2 CH3COOH (aq) (CH3COO) 2Mg (aq) + H2 (g)
NaHCO3 (s) + CH3COOH (aq) CH3COONa (aq) + CO2 (g) + H2O (l)
Acetic acid undergoes the typical chemical reactions of a carboxylic acid, such as water production and acetate by reacting with alkali metal, producing a metal acetate when reacted with a metal, and production of a metal acetate, water and carbon dioxide to react with carbonates and hydrogencarbonates. The most notable of all their reactions is the formation of ethanol by reducing and formation of derivatives such as acetyl-through nucleophilic acyl substitution. Other derivatives include replacement of acetic anhydride, this dioxide produced by the loss of water from two molecules of acetic acid. Acetic acid esters can also be formed by esterification Fischer, and amides can also be formed. When heated above 440 C, acetic acid decomposes to produce carbon dioxide and methane, or to produce ethenone and water.
Acetic acid can be detected by the characteristic odor. A color reaction for acetic acid salts of iron (III) solution chloride, resulting in a deep red color that disappears after acidification. Acetate when heated in the form of arsenic trioxide cacodyl oxide, that can be detected by its malodorous vapors.
Biochemistry
The acetyl group, acetic acid derivatives, is fundamental to the biochemistry of virtually all forms of life. When bound to coenzyme A is essential for the metabolism of carbohydrates and fats. However, the concentration of free acetic acid in Cells were maintained at a low level to avoid disrupting the control of the pH of the contents of the cell. Unlike the long chain carboxylic acids (fatty acids), acid acetic acid does not occur in natural triglycerides. However, the artificial triglyceride triacetin (glycerin triacetate) is a common food additive, and is in cosmetics and topical medications.
Acetic acid is produced and excreted by acetic acid bacteria, especially of the genus Acetobacter and Clostridium acetobutylicum. These bacteria are found universally in foodstuffs, water and soil, and acetic acid is produced naturally as fruits and spoil other foods. Acetic acid is also a component of the vaginal lubrication of humans and other primates, which seems to serve as an antibacterial agent smooth.
Production
Purification and concentration plant in 1884 acetic acid
Acetic acid is produced both synthetically and by bacterial fermentation. Today, [when?] Accounts biological route, approximately 10% of world production, but remains important for the production vinegar, as the laws of many nations food purity stipulate that vinegar used in foods must be of biological origin. About 75% acetic acid use in the chemical industry is made by methanol carbonylation, explained below. Alternative methods account for the rest. Total production world virgin acetic acid is estimated at 5 Mt / a (million tonnes per year), about half of which is produced in the United States. production Europe stands at approximately 1 Mt / a and is declining, and 0.7 Mt / a is produced in Japan. Another 1.5 million tons are recycled every year, bringing the market a global total of 6.5 Mt / a. The two biggest producers of virgin acetic acid are Celanese and BP Chemicals. Other major producers are Millennium Chemicals, chemical products Sterling, Samsung, Eastman, and Svensk ETANOLKEMI.
Methanol carbonylation
Most virgin acetic acid is produced by carbonylation of methanol. In this process, methanol and carbon monoxide react to produce acetic acid according to the chemical equation:
CO + CH3COOH CH3OH
The process involves iodomethane as an intermediary, and occurs in three steps. A catalyst, usually a metal complex, is necessary for the carbonylation (step 2).
CH3OH CH3I + H2O + HI
CH3COI CH3I + CO
CH3COI H2O + CH3COOH + HI
By altering the process conditions, acetic anhydride can also occur in the same plant. Because both methanol and carbon monoxide raw materials, methanol carbonylation long appeared to be an attractive method for acetic acid production. Henry Drefyus at the British Celanese developed a methanol carbonylation pilot plant in 1925. However, the lack of practical materials which may contain corrosive reaction mixture at high pressures needed (200 atm or more) discouraged the marketing of these routes. The first commercial process carbonylation of methanol, which used a cobalt catalyst, was developed by German chemical company BASF in 1963. In 1968, a rhodium-based catalyst (cisRh (CO) 2I2]) It was discovered that could operate efficiently at lower pressure with almost no by-products. The first plant using this catalyst was built by U.S. Company Monsanto Chemical Company in 1970 and rhodium carbonylation of methanol produced became the dominant method of acetic acid production (see Monsanto process). In late 1990, the company BP Chemicals sells chemicals Cativa catalyst ([Ir (CO) 2I2]), which is promoted by ruthenium. This process catalyzed by Cativa iridium is greener and more efficient and has largely supplanted the Monsanto process, often in the same plants.
Acetaldehyde oxidation
acid before marketing the Monsanto process, most acetic acid was produced by oxidation of acetaldehyde. This remains the second factory most important method, while not competitive with methanol carbonylation.
Acetaldehyde may be produced by oxidation of butane or light naphtha, or hydration ethylene. When the butane or light naphtha is heated with air in the presence of various metal ions, including manganese, cobalt and chromium, formation of peroxides and then decompose to produce acetic acid according to the chemical equation
2 C4H10 + 5 O2 4 H2O + 2 CH3COOH
In general, the reaction is run at combination of temperature and pressure designed to be as hot as possible while keeping the liquid butane. Typical conditions of reaction are C and 150 55 atm. secondary products can also form, including butanone, ethyl acetate, formic acid, propionic acid. These secondary products are also of great commercial value, and the reaction conditions can be altered to produce more of them if this is economically useful. However, the separation of acid acetic acid from these products adds to the cost of the process.
Under similar conditions and using similar catalysts used for oxidation of butane, acetaldehyde can be oxidized by air oxygen to produce acetic acid
2 CH3CHO + O2 2 CH3COOH
Using modern catalysts, this reaction can have a yield of acetic acid above 95%. The main side products are ethyl acetate, formic acid and formaldehyde, all of which have points lower boiling point than acetic acid and are easily separated by distillation.
Ethylene Oxidation
Acetaldehyde may be prepared from ethylene via the Wacker process, and then oxidized as above. More recently, a cheaper conversion from one stage of ethylene to acetic acid was commercialized by the chemical company Showa Denko, which opened a plant for oxidation of ethylene in Italian, Japan, in 1997. The process is catalyzed by a catalyst palladium metal supported on an acid as tungstosilicic heteropoly acid. It is intended to be competitive with methanol carbonylation for smaller plants (100 250 kt / a), depending on the local price of ethylene.
oxidative fermentation
For most of human history, acetic acid, as vinegar has been made by acetic acid bacteria of the genus Acetobacter. Given enough oxygen, these bacteria can produce vinegar from a variety of alcoholic foodstuffs. Commonly used feeds include apple cider, wine and fermented grain, malt, rice or mashed potatoes. The chemical reaction Global provided by these bacteria is:
O2 + H2O C2H5OH + CH3COOH
A diluted alcohol solution inoculated with Acetobacter and kept in a warm, ventilated place vinegar will become in the course of several months. Industrial vinegar-making methods to accelerate this process by improving the delivery of oxygen to the bacteria.
The first batches of vinegar produced by fermentation probably followed errors in the process of winemaking. If must is fermented at too high a temperature, Acetobacter overwhelm the natural yeast on the grapes. As demand for vinegar for culinary, medical and health increased, vintners quickly learned to use other materials organic produce vinegar in the hot summer months before the grapes are ripe and ready for processing into wine. This method was slow, however, not always successfully, as the vintners did not understand the process.
One of the first modern commercial processes was the method of "fast" or "method German ", first practiced in Germany in 1823. In this process, fermentation takes place in a tower full of wood chips or charcoal. Food containing alcohol is dripped into the top of the tower, and the fresh air supplied from the bottom by natural or forced convection. The improved air supply in the process of reducing time to prepare vinegar from months to weeks.
[Most vinegar today when?] Is done in submerged tank culture, first described in 1949 by Otto Heinrich Ebner and Hromatka. In this method, alcohol is fermented to vinegar in a continuously stirred tank, and oxygen is supplied by bubbling air through solution. Using modern applications of this method, vinegar 15% acetic acid can be prepared in just 24 hours of batch process, even 60 hours 20% in fed-batch process.
Anaerobic Fermentation
Species of anaerobic bacteria, including members of the genus Clostridium, can convert sugars acetic acid directly, without the use of ethanol as an intermediate. The overall chemical reaction conducted by these bacteria can be represented as:
C6H12O6 3 CH3COOH
More interesting from the point of view of an industrial chemical, acetogenic bacteria can produce acetic acid from compound one carbon, including methanol, carbon monoxide, or a mixture of carbon dioxide and hydrogen:
2 CO2 + 4 H2 + 2 H2O CH3COOH
This ability of Clostridium to utilize sugars directly, or to produce acetic acid from less costly inputs, means that these bacteria could potentially produce acetic acid more efficiently than ethanol-oxidants such as Acetobacter. However, Clostridium bacteria are less acid tolerant than Acetobacter. Even more strains of Clostridium acid-tolerant vinegar can produce only a small percentage of acetic acid, compared with Acetobacter strains can produce vinegar of up to 20% acetic acid. At present, it remains more profitable to produce vinegar using Acetobacter to produce Clostridium and then concentrate. As a result this, although acetogenic bacteria have been known since 1940, industrial use remains confined to a few specialized applications.
Applications
2.5 bottle liters of acetic acid in a laboratory.
Acetic acid is a chemical reagent for the production of chemical compounds. The largest single use of acetic acid in the production of vinyl acetate monomer, closely followed by the production of acetic anhydride and ester. The volume of acetic acid used in vinegar is comparatively small.
Vinyl acetate monomer
The major use of acetic acid is to produce vinyl acetate monomer (VAM). This application consumes approximately 40% to 45% of world production of acetic acid. The reaction is of ethylene and acetic acid with oxygen on a palladium catalyst.
2 H3C-COOH + 2 C2H4 + O2 2 H3C-CO-O-CH = CH2 + 2 H2O
Vinyl acetate can be polymerized to polyvinyl acetate or other polymers, applied in paints and adhesives.
Ester production
The main acetic acid esters are commonly used solvents for inks, paints and coatings. The esters are ethyl acetate, n-butyl acetate, isobutyl acetate and propyl acetate. They are typically produced by the reaction catalyzed by acetic acid and the corresponding alcohol:
H3C H3C-COOH + HO-R-CO-O + H2O, (R = an alkyl group general)
Most acetate esters without however, are produced from acetaldehyde using the Tishchenko reaction. In addition, ether acetates are used as solvents for nitrocellulose, acrylic lacquers, varnish removers and wood stains. First monoethers glycol is produced from ethylene oxide or propylene oxide with alcohol, which are then esterified with acetic acid. The three main products are ether acetate ethylene glycol monoethyl (EEA), ethylene glycol monobutyl ether acetate (EBA) and propylene glycol monomethyl ether acetate (PMA). This application consumes about 15% to 20% acetic acid worldwide. Ether acetates, eg EEA, are have proven to be harmful to human reproduction.
Acetic anhydride
The product of condensation of two molecules of acetic acid acetic anhydride. World production of acetic anhydride is one of the main applications and uses of approximately 25% to 30% of global production acetic acid. The acetic anhydride can be produced directly by methanol carbonylation bypassing the acid, and production facilities can be adapted Cativa for the production of anhydride.
Acetic anhydride is a strong acetylation agent. As such, its primary application is for cellulose acetate, a synthetic textile is also used for photographic film. Acetic anhydride is a reagent for the production of aspirin, heroin and other compounds.
Vinegar
In the form of vinegar, acetic acid solutions (typically 4% and 18% acetic acid, with the overall percentage is calculated by weight) are directly used as a condiment, and also in the pickling of vegetables and other foodstuffs. Table vinegar tends to be more diluted (4% to 8% acetic acid) while commercial food pickling generally used more concentrated solutions. The amount of acetic acid used as vinegar on a world scale is not large, but historically this is by far the oldest and largest application known. Tapat hot sauce is an example of a product that combines the acetic acid and water to create vinegar in the production of foodstuffs.
The solvent used as
Glacial acetic acid is an excellent polar protic solvent, as indicated above. Often used as a solvent for recrystallization to purify organic compounds. pure acetic acid is used as a solvent in the production terephthalic acid (TPA), the raw material of polyethylene terephthalate (PET). Although at present [when?] Represents 510% of worldwide use acetic acid, this specific application is expected to grow significantly over the next decade, with increasing the production of PET.
Acid acetic acid is often used as a solvent for reactions involving carbocations, such as Friedel-Crafts alkylation. For example, a stage in the commercial manufacture of camphor Synthetic implies a Wagner-Meerwein rearrangement of camphene to isobornyl acetate, acetic acid acts both here and solvent as a nucleophile to trap rearranged carbocation. Acetic acid is the solvent of choice when the reduction of nitro-aryl group of an aniline with palladium on carbon.
acid glacial acetic acid is used in analytical chemistry for the determination of weakly alkaline substances such as organic amides. glacial acetic acid is a base much weaker than water, so the amide behaves as a strong base in this medium. Then, can be valued using a solution of acetic acid ice of a strong acid such as perchloric acid.
Other applications
dilute acetic acid solutions are also used for content Soft acidity. The examples in the home environment include the use of a stop bath for photographic film development, and descaling agents to eliminate Lime taps and boilers.
Dilute acetic acid solutions can be used in the clinical laboratory for red blood cell lysis to do manual white blood cells. Another clinical use is to lyse red blood cells that can obscure other important components in the urine for microscopic examination.
The acid is also used for the treatment of box jellyfish stings by deactivating the stinging cells of jellyfish, injury prevention or death if applied immediately, and for the external treatment of ear infections in people in the preparations and Vosol. Equivalently, acetic acid is used as a preservative for silage spray cattle, to discourage the growth of bacteria and fungi. Glacial acetic acid is also used as a wart wart remover.
Organic or inorganic salts are produced from acetic acid, including:
Sodium acetate, used in the textile industry and as a food preservative (E262).
Copper (II) acetate is used as a pigment and a fungicide.
Aluminium and iron acetate (II) as mordants acetatesed dyes.
Palladium (II) acetate, used as a catalyst in organic coupling reactions such as Heck reaction.
Silver acetate, used as a pesticide.
Replacing acetic acids produced include:
Monochloroacetic acid (MCA), dichloroacetic acid (considered a secondary product) and trichloroacetic acid. MCA is used in the manufacture of indigo dye.
bromoacetic acid, which is esterified to produce the ethyl bromoacetate reagent.
trifluoroacetic acid, which is a common reagent in organic synthesis.
The amounts of acetic acid used in these applications yes, well (Not TPA) account for another 510% of the world the use of acetic acid. These applications are, however, is expected to grow as much as the production of TPA. dilute acetic acid is also used in physical therapy to dissolve the lumps of scar tissue by iontophoresis.
Security
Concentrated acetic acid is corrosive and should therefore be handled with proper care, it can cause skin burns, permanent eye damage and irritation to mucous membranes. These burns or blisters may not appear until hours after exposure. Latex gloves offer no protection, gloves especially so resistant, such as nitrile rubber should be worn when handling the compound. Concentrated acetic acid can be turned with difficulty in the lab. It becomes in a flammable risk if the ambient temperature exceeds 39 C (102 F), and may form explosive mixtures with air above this temperature (explosion limit: 5.416%).
The dangers of acetic acid solutions depends on the concentration. The following table lists the EU classification of acetic acid solutions:
Security symbol
Concentration
by weight
Molarity
Classification
R Phrases
1025%
1.674.16 mol / L
Irritating (Xi)
R36/38
2590%
4.1614.99 mol / L
Corrosive (C)
R34
> 90%
> 14.99 mol / L
Corrosive (C) flammable (F)
R10, R35
Solutions in more than 25% acetic acid are handled in a fume hood because the vapor acre, corrosive. acetic acid diluted, in the form of vinegar, is harmless. However, the ingestion of stronger solutions is dangerous to human and animal life. It can cause severe damage to the digestive system and a potentially lethal change in the acidity of the blood.
Due to incompatibilities, it is recommended to keep away from acetic acid chromic acid, glycol ethylene, nitric acid, perchloric acid, permanganate, peroxides and hydroxyls.
See also
Acetyl group, CH3-CO group, abbreviated Ac
Acids in wine
Common chemicals, where to buy common chemicals used in experiments
Sodium citrate
References
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Executive ^ ed.: J. Buckingham (1996). Dictionary of organic compounds. 1 (6th ed.). London: Chapman & Hall. ISBN 0-412-54090-8.
^ Yoneda, N., Kusano, S. Yasui, M.; Pujadó, p.; Wilcher, S. (2001). "Recent advances in processes and catalysts for acetic acid production." Applied Catalysis A, General 221 (1-2): 253 265. doi: 10.1016/S0926-860X (01) 00800-6.
^ "The production of denunciation." Chem Eng News: 6776. July 11, 2005.
^ Abcde Suresh, Bala (2003). "Acetic acid. Chemical Economic Handbook. SRI International. pp. 602.5000. http://www.sriconsulting.com/CEH/Public/Reports/602.5000/.
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^ Sano, Ken-ichi Uchida, Hiroshi; Wakabayashi, Syoichirou (1999). A new process for acetic acid production by direct oxidation of ethylene. 3. 6660. doi: 10.1023 / A: 1019003230537.
Ab ^ Otto Heinrich Hromatka and Ebner (1959). "Vinegar oxidative submerged fermentation." Ind. Eng. Chem 51 (10): 1279 1280. doi: 10.1021/ie50598a033.
^ Everett P. Partridge (1931). "Acetic acid and cellulose acetate in the United States a comprehensive survey of Economics and Technology Evolution. "Ind. Eng. Chem 23 (5): 482 498. Doi: 10.1021/ie50257a005.
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References
Wikimedia Commons has multimedia on acetic acid
International Chemical Safety Card 0363
National Pollutant Inventory – acetic acid fact sheet
NIOSH Guide pocket to Chemical Hazards
Method of sampling and analysis
29 CFR 1910.1000, Table Z-1 (U.S. permissible exposure limits)
ChemSub Online: CAS No. 64-19-7, Acetic Acid
The use of acetic acid in organic synthesis
Acetic acid pH and titration – freeware for analysis data, simulation and distribution diagram generation
Calculation of vapor pressure, liquid density, viscosity of the fluid dynamic surface tension of acetic acid
EV
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Acetic acid Boric acid aluminum acetotartrate Chloramphenicol Chlorhexidine Gentamicin Ciprofloxacin Clioquinol hydrogen peroxide nitrofural Miconazole Neomycin polymyxin B rifamycin tetracycline ofloxacin
Corticosteroids
Betamethasone Dexamethasone Prednisolone Hydrocortisone fluocinolone acetonide
Analgesics and anesthetics
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