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Coking is the process of heating coal in the absence of oxygen to a temperature above 600 °C (1,112 °F) to drive off the volatile components of the raw coal, leaving behind a hard, strong, porous material with a high carbon content called coke. Coke is predominantly carbon.
Despite the development of catalytic cracking processes, coking processes have survived as a popular refining process all over the world to refine the heavy end of crudes or heavy oils through carbon rejection as coke. Coking is the most severe thermal process used in the refinery to treat the very bottom-of-the-barrel of crude oil, i.e., vacuum residue.
Because of the high severity of thermal cracking during coking, the residue feed is completely converted to gas, light and medium distillates, and coke with no production of residual oil. Three different coking processes are used in the refineries: delayed coking, fluid coking, and flexi-coking (a variation of fluid coking). The common objective of the three coking processes is to maximize the yield of distillate products in a refinery by rejecting large quantities of carbon in the residue as solid coke, known as petroleum coke. Complete rejection of metals with the coke product provides an attractive alternative for upgrading the extra-heavy crude and bitumen, and that is particularly useful for initial processing of tar (or oil) sands for liberating the hydrocarbons from the sand that is left behind with the coke. Finding markets for the coke product as fuel or as filler for manufacturing anodes for the electrolysis of alumina (possible only with petroleum coke from delayed coking) makes the economics of coking more attractive by creating value for the rejected carbon. Sulfur and metal contents of the petroleum coke, as determined by the sulfur and metal contents of the residue feed, are two important factors that affect the commercial value of petroleum coke. Of the two coking processes, delayed coking is the preferred approach in many refineries that process heavy crudes.
Ethyl acetate (systematically ethyl ethanoate, commonly abbreviated EtOAc, ETAC or EA) is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This flammable, colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues, nail polish removers, and the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent
Ethyl acetate is synthesized in industry mainly via the classic Fischer esterification reaction of ethanol and acetic acid. This mixture converts to the ester in about 65% yield at room temperature:
CH3CO2H + CH3CH2OH → CH3CO2CH2CH3 + H2O
The reaction can be accelerated by acid catalysis and the equilibrium can be shifted to the right by removal of water.
It is also prepared in industry using the Tishchenko reaction, by combining two equivalents of acetaldehyde in the presence of an alkoxide catalyst:
2 CH3CHO → CH3CO2CH2CH3
Silicotungstic acid is used to manufacture ethyl acetate by the alkylation of acetic acid by ethylene:[9]
C2H4 + CH3CO2H → CH3CO2C2H5
Uses
Ethyl acetate is used primarily as a solvent and diluent, being favored because of its low cost, low toxicity, and agreeable odor.[5] For example, it is commonly used to clean circuit boards and in some nail varnish removers (acetone is also used). Coffee beans and tea leaves are decaffeinated with this solvent.[10] It is also used in paints as an activator or hardener. Ethyl acetate is present in confectionery, perfumes, and fruits. In perfumes it evaporates quickly, leaving the scent of the perfume on the skin.
Ethyl acetate is an asphyxiant for use in insect collecting and study. In a killing jar charged with ethyl acetate, the vapors will kill the collected insect quickly without destroying it. Because it is not hygroscopic, ethyl acetate also keeps the insect soft enough to allow proper mounting suitable for a collection. However, ethyl acetate is regarded as potentially doing damage to insect DNA, making specimens processed this way less than ideal for subsequent DNA sequencing.
Acetic acid, systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH (also written as CH3CO2H, C2H4O2, or HC2H3O2). Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC. Acetic acid is also known as acetyl hydroxide (AcOH).
Acetic acid Use :
Acetic acid is a chemical reagent for the production of chemical compounds. The largest single use of acetic acid is in the production of vinyl acetate monomer, closely followed by acetic anhydride and ester production. The volume of acetic acid used in vinegar is comparatively small.
1medical: Acetic acid is used as part of cervical cancer screening in many areas in the developing world. The acid is applied to the cervix and if an area of white appears after about a minute the test is positive.
2 food : Vinegar is used directly as a condiment, and in the pickling of vegetables and other foods. Table vinegar tends to be more diluted (4% to 8% acetic acid), while commercial food pickling employs solutions that are more concentrated.
3 Use as solvent As a polar protic solvent, acetic acid is frequently used for recrystallization to purify organic compounds. Acetic acid is used as a solvent in the production of terephthalic acid (TPA), the raw material for polyethylene terephthalate (PET). In 2006, about 20% of acetic acid was used for TPA production.
Production
Acetic acid is produced industrially both synthetically and by bacterial fermentation. About 75% of acetic acid made for use in the chemical industry is made by the carbonylation of methanol, explained below.[27] The biological route accounts for only about 10% of world production, but it remains important for the production of vinegar because many food purity laws require vinegar used in foods to be of biological origin. Other processes are methyl formate isomerization, conversion of syngas to acetic acid, and gas phase oxidation of ethylene and ethanol.
Acetic acid can be purified via fractional freezing using an ice bath. The water and other impurities will remain liquid while the acetic acid will precipitate out. As of 2003-2005, total worldwide production of virgin acetic acid was estimated at 5 Mt/a (million tonnes per year), approximately half of which was produced in the United States. European production was approximately 1 Mt/a and declining, while Japanese production was 0.7 Mt/a. Another 1.5 Mt were recycled each year, bringing the total world market to 6.5 Mt/a. Since then, the global production has increased from 10.7 Mt/a in 2010 to 17.88 Mt/a in 2023. 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 acetic acid is produced by methanol carbonylation. In this process, methanol and carbon monoxide react to produce acetic acid according to the equation:
The process involves iodomethane as an intermediate, and occurs in three steps. A metal carbonyl catalyst is needed for the carbonylation (step 2).
CH3OH + HI → CH3I + H2O
- CH3I + CO → CH3COI
- CH3COI + H2O → CH3COOH + HI
Two related processes exist for the carbonylation of methanol: the rhodium-catalyzed Monsanto process, and the iridium-catalyzed Cativa process. The latter process is greener and more efficient and has largely supplanted the former process.[19] Catalytic amounts of water are used in both processes, but the Cativa process requires less, so the water-gas shift reaction is suppressed, and fewer by-products are formed.
By altering the process conditions, acetic anhydride may also be produced in plants using rhodium catalysis.
Acetaldehyde oxidation
Prior to the commercialization of the Monsanto process, most acetic acid was produced by oxidation of acetaldehyde. This remains the second-most-important manufacturing method, although it is usually not competitive with the carbonylation of methanol. The acetaldehyde can be produced by hydration of acetylene. This was the dominant technology in the early 1900s.
Light naphtha components are readily oxidized by oxygen or even air to give peroxides, which decompose to produce acetic acid according to the chemical equation, illustrated with butane:
2 C4H10 + 5 O2 → 4 CH3CO2H + 2 H2O
Such oxidations require metal catalyst, such as the naphthenate salts of manganese, cobalt, and chromium.
Ethylene oxidation
Acetaldehyde may be prepared from ethylene via the Wacker process, and then oxidised as above.
In more recent times, chemical company Showa Denko, which opened an ethylene oxidation plant in Ōita, Japan, in 1997, commercialised a cheaper single-stage conversion of ethylene to acetic acid. The process is catalyzed by a palladium metal catalyst supported on a heteropoly acid such as silicotungstic acid. A similar process uses the same metal catalyst on silicotungstic acid and silica:
C2H4 + O2 → CH3CO2H
It is thought to be competitive with methanol carbonylation for smaller plants (100-250 kt/a), depending on the local price of ethylene.
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