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Acetic acid

Nomenclature
The trivial name acetic acid is derived from acetum, the Latin word for vinegar, and is linked to the acid word itself. The synonym ethanoic acid is manufactured according to the nomenclature of the IUPAC replacement.
Glacial acetic acid is a trivial name of the acid Acetic without water. Similar to the German Eisessig name (literally, ice-vinegar), the name comes from the ice crystals that form as slightly below the ambient temperature of 16.7 C (62 F).
The most common abbreviation for acetic acid HOAc where Ac represents the acetyl group CH3 (= O). As part of the acid-base reactions CDT abbreviation is often used, instead of designating Ac acetate anion (CH3COO, COA for short), although this use is considered by many to be misleading. In both cases, the CA should not be confused with the abbreviation of the chemical element actinium. Acetic acid has the empirical formula CH2O. To highlight the role of active hydrogen in the formation of sodium acetate salt, people write the molecular formula C2H4O2 or HC2H3O2. To better reflect its structure, acetic acid is often written as CH3-CO2-H, CH3COOH or CH3CO2H. The ion resulting from loss of H + from acetic acid is the acetate anion. Acetate name may also refer to a salt containing this anion or an ester of acetic acid.
History
Vinegar was known at the beginning of civilization, as the natural result of exposure to air beer and wine, as acetic acid bacteria are present everywhere in the world. The use of acetic acid in chemistry extends into the third century BC, when the philosopher Greek Theophrastus describes how vinegar acted on metals to produce pigments useful in art, including white lead (lead carbonate) and verdigris, a mixture of green copper salts including copper (II) acetate. Ancient Romans boiled sour 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 of Saturn, which contributed to the poisoning Lead in the Roman aristocracy.
In the 8th century alchemist Jabir Ibn Hayyan Muslims (Geber) was the first to concentrate the acid acetic vinegar by distillation. During the Renaissance, glacial acetic acid was prepared by the dry distillation of metallic acetates some (the most significant copper (II) acetate). The 16th century German alchemist Andreas Libavius describes such a procedure, and he compared the glaciers acetic acid produced by this means to vinegar. The presence of water in vinegar has a profound effect on acetic acid properties that chemists for centuries found that glacial acetic acid and the acid in vinegar are two different substances. The French chemist Pierre Adet them is proved to be identical.
Crystallized acetic
In 1847, the German chemist Hermann Kolbe synthesized acetic acid from inorganic materials for the first time. This reaction sequence consisting of chlorination of carbon disulfide to carbon tetrachloride, followed pyrolysis of tetrachloroethene and chlorination of aqueous trichloroacetic acid, and concluded with the electrolytic reduction of acid acetic.
By 1910, more glacial acetic acid has been obtained from the "Liquor pyroligneous" distillation of wood. Acetic acid was isolated from this by treatment with milk of lime and calcium acetate which results is then acidified with sulfuric acid recover acetic acid. At that time, Germany was producing 10,000 tons of glacial acetic acid, about 30% what has been used for the manufacture of indigo dye.
Chemical
Acetic acid crystals
Hydrogen (H) atom in the carboxyl group (OOH) in carboxylic acids such as acetic acid may be issued as an ion H + (protons), which give an acidic character. Acetic acid is a small, efficient monoacid in aqueous solution with a pKa value of 4.75. Its conjugate base is the Acetate (CH3COO). A solution of 1.0 M (the concentration of domestic vinegar) has a pH of 2.4, indicating that only 0.4% of acetic acid molecules are separated.
cyclic dimer of acetic acid, hydrogen bonds are dashed
The crystal structure of acid acetic shows that the molecules to combine into dimers connected by hydrogen bonds. The dimers can also be detected in the steam 120 C. They also occur in the liquid phase in dilute solutions in non-solvent hydrogen bonds, and to some extent in the acetic acid True, but are confused by hydrogen bonding solvents. The enthalpy of dissociation of the dimer is estimated to be 65.066.0 kcal / mol, and entropy dissociation at 154 157 J mol1 K1. This behavior is shared by the dimerization of other lower carboxylic acids.
Liquid acetic acid is a hydrophilic (Polar) protic solvent, similar to ethanol and water. With a moderate static relative permittivity (dielectric constant) of 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 blends easily with other non-polar solvents like water, chloroform, hexane. With higher alkanes (Starting octane) acetic acid is not completely miscible over. The miscibility gap is becoming larger with more n-alkanes. This property is dissolved and miscibility of acetic acid, it is a chemical widely used in industry.
Reactions chemical
Acetic acid is corrosive to metals including iron, magnesium and zinc, hydrogen and metal salts forming called acetates. Aluminium, when exposed to oxygen, forms a thin layer of aluminum oxide on its surface which is relatively resistant the acid, allowing 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 ". Except significant chromium (II) acetate, almost all acetates are soluble in water.
Mg (s) + 2 CH3COOH (aq) (CH3COO) 2 mg (aq) + H2 (g)
NaHCO3 (s) + CH3COOH (aq) CH3COONa (aq) + CO2 (g) + H2O (l)
Acetic acid undergoes chemical reactions typical of a carboxylic acid, such as the production of water and a metal ethanoate in the reaction with alkali, producing a metal ethanoate when reacted with a metal, and producing a metal ethanoate, water and carbon dioxide when it reacts with carbonates and bicarbonates. The most remarkable All his reactions is the formation of ethanol by reduction, and the formation of derivatives such as acetyl chloride by the substitution bias nucleophile. Other derivatives of acetic anhydride alternatives; dioxide that is produced by the loss of water from two molecules of acid acetic. Esters of acetic acid can also be formed by esterification of Fischer, and amides can also be formed. When is heated above 440 C, acetic acid decomposes to produce carbon dioxide and methane, or produce ethenone and water.
Acid acetic acid can be detected by its characteristic odor. A color reaction for salts of acetic acid is iron (III) chloride solution, This gives a very red color that disappears after acidification. Acetates when heated to form arsenic trioxide cacodyl oxide, which can be detected by its malodorous vapors.
Biochemistry
The acetyl group, acetic acid derivative, is fundamental to biochemistry virtually all forms of life. When bound to coenzyme A, it is essential for the metabolism of carbohydrates and lipids. However, the concentration of acid free acetic cells is maintained at a low level to avoid disturbing the pH control of cell contents. Unlike longer-chain acids carboxylic (fatty acids), acetic acid does not occur in natural triglycerides. However, the artificial triglyceride triacetin (glycerin triacetate) is a common food additive, and is found in cosmetics and topical medications.
Acetic acid is produced and excreted by acetic acid bacteria, including Acetobacter genus and Clostridium acetobutylicum. These bacteria are ubiquitous in food, water and soil, and acetic acid is produced naturally in fruits and other foods spoil. Acetic acid is also an element of vaginal lubrication of man and other primates, where it seems to serve as a mild antibacterial agent.
Production
Purification and concentration plant for acetic acid in 1884
Acetic acid is produced by both synthetic and bacterial fermentation. Today, [when?] The biological route accounts represents only about 10% of world production, but it remains important for vinegar production, as the laws of many countries' purity Food stipulates that the vinegar used in foods should be organic. Approximately 75% acetic acid for use in the chemical industry is made by methanol carbonylation, explained below. Other methods to account for the rest. The total worldwide production of acetic acid Virgin is estimated at 5 Mt / a (million tonnes per year), of which about half is produced in the United States. European production totaled about 1 Mt / a and is declining, and 0.7 Mt / a is produced in Japan. Another Mt 1.5 are recycled each year, bringing the total world market of 6.5 Mt / a. The two biggest producers of virgin acetic acid are Celanese and BP Chemicals. Other major producers include Millennium Chemicals, Sterling Chemicals, Samsung, Eastman, and Svensk Etanolkemi.
methanol carbonylation
Most virgin acetic acid is produced by carbonylation of methanol. In this process, the methanol and carbon monoxide react to produce acetic acid according to the chemical equation:
CH3OH + CO CH3COOH
Process involves iodomethane as intermediary, and occurs in three stages. A catalyst, usually a metal complex, is necessary for the carbonylation (Step 2).
CH3OH + HI CH3I + H2O
CH3I + CO CH3COI
CH3COOH + H2O + HI CH3COI
By changing the process conditions, the anhydride acetic acid can also be produced on the same plant. Because methanol and carbon monoxide, carbon materials are raw, methanol carbonylation long appeared to be an attractive method for the production of acetic acid. Henry Drefyus at British Celanese developed a methanol carbonylation plant pilot in 1925. However, a lack of material that could contain the corrosive reaction mixture at high pressures needed (200 atm or more) discouraged the marketing of these roads. The first commercial methanol carbonylation process, which used a cobalt catalyst, was developed by the German company BASF Chemical in 1963. In 1968, a catalyst based on rhodium (cisRh (CO) 2I2]) has been discovered that could operate effectively low pressure with almost no byproducts. The first plant using this catalyst was built by the U.S. Chemical Company Monsanto Company in 1970, and rhodium-catalyzed Methanol carbonylation became the dominant mode of production of acetic acid (see Monsanto process). In the late 1990s, the company BP Chemicals Chemicals marketed Cativa the catalyst ([Ir (CO) 2I2]), which is promoted by ruthenium. The iridium-catalyzed process is Cativa greener and more efficient and has largely supplanted the Monsanto process, often in the same plants.
oxidation of acetaldehyde
acid before marketing process Monsanto acetic most was produced by the oxidation of acetaldehyde. This is the second largest manufacturing method, even if it is not competitive with methanol carbonylation.
Acetaldehyde can be produced by oxidation of butane or light naphtha, or by hydration of ethylene. When butane or light naphtha is heated with air at various metal ions, including manganese, cobalt and chromium form peroxides and then decompose to produce acetic acid according to the chemical equation
2 C4H10 + O2 4 5 CH3COOH + 2 H2O
Generally, the reaction proceeds at a combination of temperature and pressure designed to be as hot as possible while keeping the liquid butane. Typical reaction conditions are 150 C and 55 atm. The secondary products may also form, including butanone, ethyl acetate, formic acid, propionic acid. These secondary products are also worth commercial, and reaction conditions can be modified to produce more of them, if it is economically useful. However, the separation of acid acetic acid from these products which increases the cost of the process.
Under similar conditions and using similar catalysts as those used for butane oxidation, acetaldehyde can be oxidized by oxygen from air to produce acetic acid
2 CH3CHO CH3COOH + 2 O2
Using modern catalysts, this reaction may have a yield of acetic acid over 95%. The major side products are acetate ethyl, formic acid and formaldehyde, all of which have boiling points lower than the acetic acid and are easily separated by distillation.
oxidation of ethylene
Acetaldehyde may be prepared from ethylene via the process Wacker, and then oxidized as above. More recently, a better one-step conversion of ethylene to acetic acid has commercialized by the chemical company Showa Denko, which opened a plant for the oxidation of ethylene in the ITA, Japan, in 1997. Process is catalyzed by a palladium metal catalyst supported on an acid such as heteropoly acid tungstosilicic. It is thought to be competitive with methanol carbonylation for smaller plants (100 250 kt / a), as the local price of ethylene.
oxidative fermentation
For most of history human, acetic acid, as vinegar, was 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 including apple cider, wine and fermented grain, malt, rice or mashed potatoes. The overall chemical reaction facilitated by these bacteria is as follows:
C2H5OH + O2 + H2O CH3COOH
A diluted alcohol solution inoculated with Acetobacter and kept in a warm, ventilated place will become vinegar During a few months. Industrial vinegar-making methods to accelerate this process by improving the supply of oxygen to the bacteria.
The first batches of vinegar produced by fermentation probably followed errors in the winemaking process. If the must is fermented at a temperature too high Acetobacter overwhelm the yeast naturally on the grapes. As demand for vinegar for culinary, medical and health increased, vintners quickly learned to use other organic materials to produce vinegar in the hot months of summer, before the grapes were ripe and ready for into wine. This method has been slow, however, and not always successful, as the tenants do not understand the process.
One of the first process modern commercial method was "fast" or "German method", first practiced in Germany in 1823. In this process, fermentation takes place in a tower filled with wood chips or charcoal. Feed containing alcohol is flowing across the top of the tower, and fresh air supplied from bottom either by natural or forced convection. The air supply improved in this process reduces the time to prepare vinegar from months to several weeks.
[Today, most of the vinegar when?] Is made in the cultivation of deep-water tank, first described in 1949 by Otto Heinrich and Hromatka Ebner. In this method, alcohol is fermented to vinegar in a continuously stirred tank, and oxygen is supplied by bubbling air through the solution. Using modern applications of this method, vinegar 15% acetic acid can be prepared in just 24 hours in the ordering process or even 20% within 60 hours fed-batch process.
Anaerobic fermentation
Species of anaerobic bacteria, including including members of the genus Clostridium, can convert sugars to acetic acid directly, without using ethanol as an intermediary. The chemical overall efforts by these bacteria can be represented as follows:
C6H12O6 3 CH3COOH
More interesting from the point of view of an industrial chemist, acetogenic bacteria can produce acetic acid from a carbon compounds, including methanol, carbon monoxide, or a mixture carbon dioxide and hydrogen
2 CO2 + 4 H2 + 2 H2O CH3COOH
This ability of Clostridium to directly use sugars, or produce acetic acid from less costly inputs, means that these bacteria can produce acetic acid more efficiently than ethanol-oxidizing as Acetobacter. However, Clostridium bacteria are less acid-tolerant than Acetobacter. Even the most acid-tolerant strains Clostridium vinegar can produce only a few percent of acetic acid, compared with Acetobacter strains that can produce vinegar of up to 20% acetic acid. At present, it remains more profitable to produce vinegar using Acetobacter that produce Clostridium use and then concentrate. Consequently, although acetogenic bacteria are known since 1940, their industrial use remains confined to a small number of applications niche.
Applications
bottle of 2.5 liters of acetic acid in a laboratory.
Acetic acid is a chemical reagent for production chemical compounds. The largest single use of acetic acid in the production of vinyl acetate monomer, closely followed by the anhydride acetic ester production. The volume of acetic acid in the vinegar used is relatively low.
Vinyl acetate monomer of
The major use of acetic acid to produce vinyl acetate monomer (VAM). This application consumes about 40% to 45% of worldwide production of acetic acid. The reaction of ethylene and acetic acid with oxygen over a catalyst palladium.
2 H3C-COOH + 2 C2H4 + O2 2 H3C-CO-O-CH = CH2 + 2 H2O
Vinyl acetate can be polymerized with vinyl acetate or other polymers, which are used in paints and adhesives.
ester production
The esters of acetic acid are commonly main solvents used in inks, paints and coatings. The esters are acetate, ethyl acetate, n-butyl acetate isobutyl acetate, and propyl. They are usually produced by the reaction catalyzed by acetic acid and the corresponding alcohol:
H3C-COOH + HO-R H3C-CO-OR + H2O (R = alkyl general)
Most acetate esters, however, are produced from acetaldehyde using the Tishchenko reaction. In addition, ether acetates are used as solvents for nitrocellulose, acrylic lacquers, varnishes and stains. monoethers First glycol is produced from propylene oxide or ethylene oxide with alcohol, which are then esterified with acetic acid. The three main products are ethylene glycol monoethyl ether acetate (EEA), ethylene glycol monobutyl ether acetate (EBA), and propylene glycol monomethyl ether acetate (PMA). This application consumes about 15% to 20% acid acetic worldwide. Ether acetates, eg EEA, have been shown to affect human reproduction.
Acetic anhydride
The product of condensation of two molecules of acetic acid is acetic anhydride. World production of acetic acid anhydride is a major application, and uses about 25% to 30% of world production of acetic acid. The acetic anhydride can be produced directly by methanol carbonylation bypassing the acid, and production plants Cativa can be adapted for the production of anhydride.
Anhydride acetic acid is a strong acetylation agent. As such, its primary application is for cellulose acetate, a synthetic textile 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% to 18% acetic acid, with the percentage generally calculated mass) are used directly as a condiment, and also in the canning of vegetables and other foodstuffs. Table vinegar tends to be more diluted (4% to 8% acetic acid), while commercial food pickling usually used more concentrated solutions. Quantity acetic acid used as vinegar on a global scale is not large, but historically they are far more application oldest and best known. Tapato hot sauce is an example of a product that combines the acetic acid and water to create vinegar in the production of food.
Use as solvent
Glacial acetic acid is an excellent polar protic solvent, as mentioned above. It is frequently used as a solvent for recrystallization to purify organic compounds. Pure acetic acid is used as solvent in the production of terephthalic acid (TPA) the raw material for polyethylene terephthalate (PET). Although currently [when?] Accounting for 510% of the acid in the world using acetic this specific application is expected to grow significantly in the next decade, production increases PET.
Acetic acid is often used as a solvent for reactions involving carbocations, such as Friedel-Crafts alkylation. For example, a step in the commercial manufacture of synthetic camphor involves a rearrangement of the Wagner-Meerwein camphene to isobornyl acetate, acetic acid acts both here as a solvent and a nucleophile to trap the carbocation rearranged. Acetic acid is the solvent of choice for reducing an aryl nitro group assistance of aniline Palladium on carbon.
Glacial acetic acid is used in analytical chemistry for determination of alkaline substances such as low organic amides. Glacial acetic acid is a much lower base than water, the amide behaves as a solid basis in this environment. It can then be adjusted using solution in glacial acetic acid a strong acid such as perchloric acid.
Other applications
Dilute solutions Acetic acid is also used for their slight acidity. Examples in the family include use in a stop bath during the development of photographic film, and descaling to remove scale from taps and kettles.
Dilute solutions of acetic acid icy can be used in clinical laboratories to lyse red blood cells to do manual white blood cells. Another clinical use is lysis of red blood cells can overshadow other important constituents in the urine during a microscopic examination.
The acidity is also used the treatment of box jellyfish sting of disabling the stinging cells of jellyfish, the prevention of serious injury or death if it is applied immediately, and for the external treatment of ear infections in people in preparations such as Vosol. Equivalently, acetic acid is used as an anti-conservative for silage on the farm, to discourage the growth of bacteria and fungi. Acetic acid is also used as a mole and wart remover.
Organic or inorganic salts are produced from acetic acid, including:
Sodium acetate, used in the textile industry and as food preservative (E262).
Copper (II) acetate, used as a pigment and fungicide.
Aluminium and iron acetate (II) acetatesed mordant for dyes.
Palladium (II) acetate, used as a catalyst for organic coupling reactions such as Heck reaction.
silver acetate, used as a pesticide.
Replaced acetic product include
Monochloroacetic acid (MCA), dichloroacetic acid (considered as a by-product), and trichloroacetic acid. MCA is used in the manufacture of indigo dye.
Bromoacetic acid, which is esterified to produce ethyl bromoacetate reagent.
trifluoroacetic acid, which is a common reagent in organic synthesis.
Quantities of acetic acid used in these and other applications (Outside TPA) account for another world 510% acetic acid use. These applications are, however, should not increase as much the production of TPA. In dilute acetic acid is also used in physical therapy to break up scar tissue nodules iontophoretically.
Security
Concentrated acetic acid is corrosive and must be handled with proper care, since it can cause skin burns, injuries eye damage and irritation of mucous membranes. These burns or blisters may not appear until several hours after exposure. Gloves Latex offer no protection, then specially resistant gloves, such as nitrile rubber should be worn when handling compound. Concentrated acetic acid can be ignited with difficulty in the laboratory. It becomes a flammable risk if the ambient temperature exceeds 39 C (102 F) and can form explosive mixtures with air above this temperature (Explosive Limits: 5.416%).
Hazards acetic acid solutions depend on concentration. The following table presents the ranking of the European Union acetic acid solutions:
Symbol Security
Concentration
wt
Molarity
Classification
R Phrases
1025%
1.674.16 mol / L
Irritant (Xi)
R36/38
2590%
4.1614.99 mol / L
Corrosive (C)
R34
> 90%
> 14.99 mol / L
Corrosive (C) Flammable (F)
R10, R35
Solutions to more than 25% of acetic acid are handled under a hood because of the pungent, corrosive steam. Dilute acetic acid, as vinegar, is harmless. However, ingestion of stronger solutions is dangerous to human life and animal. It can cause serious damage to the digestive system, and a change in potentially fatal blood acidity.
Due to incompatibilities, it It is advised to keep away from acetic acid, chromic acid, ethylene glycol, nitric acid, perchloric acid, permanganates, peroxide and hydroxyl.
See also
Acetyl group, CH 3 CO group, abbreviated Ac
Acids in wine
The chemicals, which purchase of chemicals commonly used in experiments
Sodium citrate
References
^ Akeroyd, F. Michael (1993). "Problem Laudan model resolution. "The British Journal for the Philosophy of Science 44 (4): 78 588. DOI: 10.1093/bjps/44.4.785.
ABC ^ Martin, Geoffrey (1917). Industrial Chemical Manufacturing (Part 1, ed organic.). London: Crosby Lockwood. pp. 33031.
Goldwhite ^, Harold (September 2003). "Brief summary of career of German chemist organic Hermann Kolbe (PDF). Bull New Haven Section. Am Chem. Soc. 20 (3). http://membership.acs.org/N/NewHaven/bulletins/Bulletin_2003-09.pdf .
^ Schweppe, Helmut (1979). "Identification of dyes for textiles old. J. Am Inst. Conservation 19 (1 / 3): 1423. DOI: 10.2307/3179569. http://aic.stanford.edu/jaic/articles/jaic19-01-003_1.html.
^ Jones, RE, Templeton, DH (1958). "The crystal structure of acetic acid. Acta Crystallogr. 11: (7) 48 487. DOI: 10.1107/S0365110X58001341.
^ Briggs, Mr. James B. Toan Nguyen, William L. Jorgensen (1991). "Monte Carlo simulations of liquid acetic acid and methyl acetate with OPLS potential functions ". J. Phys. Chem. 95: 331 522. DOI: 10.1021/j100161a065.
^ Togeas, James B. (2005). "Vapors of acetic acid: 2. Critical statistical mechanics experiments on the density of steam. "J. Phys. Chem. A 109 (24): 5438. DOI: 10.1021/jp058004j. PMID 16839071.
^ Zieborak, K. K. Olszewski (1958). Bull.Acad.Pol.Sci.Ser.Sci.Chim.Geol.Geogr. 6 (2): 331522.
^ 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.; Pujado, P. Wilcher, S. (2001). "Progress Recent processes and catalysts for the production of acetic acid. Applied catalysis A, General 221 (1-2): 253265. DOI: 10.1016/S0926-860X (01) 00800-6.
^ Production Report. "Chem. Eng. News: 6776. July 11, 2005.
^ Abcde Suresh, Bala (2003). "Acetic Acid". Manual Economic chemicals. SRI International. pp. 602.5000. http://www.sriconsulting.com/CEH/Public/Reports/602.5000/.
^ Wagner, Frank S. (1978). "Acid acetic. in Grayson, Martin. Kirk-Othmer Encyclopedia of Chemical Technology (3rd ed.). New York: John Wiley & Sons.
^ Lancaster, Mike (2002). Chemistry Green, an introductory text. Cambridge: Royal Society of Chemistry. pp. 26266. ISBN 0-85404-620-8.
^ "On the acetic acid. National Institute of Standards and Technology. http://webbook.nist.gov/cgi/cbook.cgi?ID=C64197&Units=SI&Mask=4 # Thermo-Phase. Retrieved 2/3/2008.
^ Sano, Ken-ichi Uchida, Hiroshi; Wakabayashi, Syoichirou (1999). A new method for producing acetic acid by direct oxidation of ethylene. 3. 6660. DOI: 10.1023 / A: 1019003230537.
^ Ab Hromatka Otto Ebner, Heinrich (1959). "Vinegar by oxidative fermentation submerged." 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 Survey Economic and technical developments. Ind. Chem. 23 (5): 482 498. Doi: 10.1021/ie50257a005.
Hromatka ^ O, Ebner H (1949). "Investigations on the fermentation of vinegar generator for the fermentation of vinegar and aeration procedures. Enzymologia 13: 369.
^ Jia Huey Sim, Harun Kamaruddin Azlina, Wei Sing Long and Ghasem Najafpour (2007). "Clostridium body aceticum potential as a catalyst for carbon monoxide to acetic acid: Application of response surface methodology. "Enzyme and Microbial Technology 40 (5): 12,341,243. Doi: 10.1016/j.enzmictec.2006.09.017.
Connections External
Wikimedia Commons has media related to: acetic acid
International Chemical Safety Card 0363
National Inventory pollutants – is acetic acid sheet
NIOSH Pocket Guide to Chemical Hazards
Sampling and Analysis
29 CFR 1910.1000, Table Z-1 (permissible exposure limits of the United States)
ChemSub Online: CAS 64-19-7, Acetic acid
Use of acetic acid in Organic Syntheses
acetic acid pH and titration – freeware for data analysis, simulation and distribution diagram generation
Calculation of vapor pressure, the liquid density, liquid dynamic viscosity, surface tension of the acid acetic
v, d, e
Otologicals (S02)
Antiinfectives
Acetic acid, boric acid Aluminium acetotartrate chloramphenicol chlorhexidine Ciprofloxacin Gentamicin Clioquinol hydrogen peroxide Miconazole neomycin polymyxin B nitrofurazone ofloxacin rifamycin tetracycline
Corticosteroids
Fluocinolone acetonide Betamethasone Dexamethasone Hydrocortisone Prednisolone
Analgesics and anesthetics
Phenazone cocaine lidocaine

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