b) Toluene Process
To avoid the over-production of acetone associated with the cumene oxidation process, a different reaction pathway is developed to produce phenol. About 5% of phenol produced globally is by using the oxidation of methylbenzene (toluene), a process sometimes called the Dow and California Research Process.
Reaction Pathway:
It is a two-step process.
1) First step is to oxidize the toluene to form benzoic acid.
Toluene + Oxygen → Benzoic acid + Water
C6H5CH3+ O2→C7H6O2 + H2O
Condition: Cobalt Naphthenate is used as a catalyst in the reaction with operating conditions at the temperature of 150°C and atmospheric pressure of 3 atm. It is an exothermic reaction.
2) Next is to oxidize benzoic acid to finally form phenol.
Benzoic acid + Oxygen → Phenol + Carbon Dioxide
C7H6O2+ O2 →C6H5OH + CO2
Condition: The reaction is carried out with the temperature of 220°C and atmospheric pressure ranged between 1.3 – 1.7 atm. This
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Benzoic acid and water are thus produced. The reaction is exothermic and temperature is maintained by external cooling. The crude molten benzoic acid at about 150-200°C is transferred from the reactor to distillation column, where separation of benzoic acid from unreacted toluene and produced water takes place. The toluene is then separated and recycled to the first oxidizing reactor.
The pure benzoic acid is fed to a second reactor, where it is oxidized to phenol by air and steam under 1.3 – 1.7 atm at 220°C in the presence of cupric benzoate catalyst promoted with Manganese. The reaction mass is periodically withdrawn from the second reactor into an extractor, where it is washed with water to remove unwanted tars and benzoic acid and steam are returned to second
Then the reaction tube was capped but not tightly. The tube then was placed in a sand bath reflux to heat it until a brown color was formed. Then the tube was taken out of the sand bath and allowed to cool to room temperature. Then the tube was shaken until a formation of a white solid at the bottom of the tube. After formation of the white solid, diphenyl ether (2 mL) was added to the solution and heated until the white solid was completely dissolved in the solution. After heating, the tube was cooled to room temperature. Then toluene (2 mL) was added to the solution. The tube was then placed in an ice bath. Then the solution was filtered via vacuum filtration, and there was a formation of a white solid. Then the product was dried and weighed. The Final product was hexaphenylbenzene (0.094 g, 0.176 mmol,
Felder, M. Richard, Elementary Principles of Chemical Processes, 3rd ed.; Wiley: New Jersey, 2000; p 631.
In this experiment, a mixture of three substances (benzoic acid, 2-naphthol, and 1-4 dimethoxybenzene) will be separated based off acidity strength using the liquid-liquid extraction technique through a separatory funnel. Benzoic acid and 2-napthol will be converted into ionic salts when reacting with their appropriate bases (sodium bicarbonate and sodium hydroxide). Both ionic salts will then form solids through the addition of acidic HCl. Neutral 1,4 – dimethoxybenzene forms a solid through the evaporation of ether. Each compound will then be purified through recrystallization, using the processes of dissolving the solid in either water or methanol, and isolating the solid through vacuum filtration. After a week of evaporation, the compounds will then be examined for both
The actual melting point of benzoic acid is known to be 122.4°C. Also, looking at Table1, the percent yield is shown to be 44.9%. The percent yield is how much product was recovered after the reaction was carried out. The percent yield can be used to explain why the melting point observed in the experiment didn’t match the known melting point. Obtained melting points are generally lower than the literature value melting points of a substance due to the number of impurities present in the obtained product. The percent yield of 44.9%, validates that the product could have had some impurities present, and thus the lower melting
It was clear that synthesis was of benzhydrol was taking place as the formation of the addition complex, which formed a white gunk, was present. Also, it was possible to tell the synthesis was occurring when the white gunk from the addition complex was consumed during the acid workup. During the extraction of the products there was two layers forming which also indicated that synthesis had occurred, and trace amount of white bits of product were found in the waste beaker which also indicated that synthesis occurred.
In summary, acid base extraction is a useful technique when attempting to transfer an organic compound from an organic solvent (ether) to an aqueous solvent after deprotonation with an appropriate base (NaOH). After transferring the unknown acid to the aqueous layer, precipitating it out of solution with a strong acid (HCl--protonation), followed by recrystallization, the unknown acid was able to be identified as 2-chlorobenzoic acid based off of melting point experimentation. A question that remains unanswered may be how many extractions are needed in order to have a plateau for maximum recovery? This is essential in order to have desirable results when testing for identity purposes.
For this experiment, three separate pathways were designed to utilize the exact same reagents in different orders to create a synthesis from acetophenone to methyl m-nitrobenzoate. This experiment was constructed in this format to evaluate the efficiency and overall percent yield of each pathway to determine which is most effective in synthesizing methyl m-nitrobenzoate. The pathway implemented in this experiment used acetophenone as its starting material and converted it to benzoic acid. The benzoic acid was then nitrated to m-nitrobenzoic acid, and the m-nitrobenzoic acid transformed into methyl m-nitrobenzoate.
Perchloroethylene (PCE), along with Trichloroethylene (TCE), are the products of the chlorination of Ethylene Dichloride (EDC). This process involves the reaction of EDC with chlorine, where its products undergo further distillation and purification to produce TCE and PCE fit for consumerism trade. The stoichiometry of the given process reaction indicates which is the greater desired product, i.e. either PCE or TCE. The reaction takes place at a temperature of 400 – 450 degrees Celsius and a pressure of 1 atmosphere.
The esterification procedure was performed first. To begin the lab, the heating mantle was set at the 6 setting, and the hot plate heat was turned on to low. In a round bottom flask, 6.1 g of benzoic acid and 21 mL of MeOH were added into the flask. Once this was added to the flask, 2 mL of sulfuric acid was added and poured carefully down the side of the flask. It was noted that after the addition of the sulfuric acid there was heat production in the flask. The contents were swirled and a boiling chip was added into the flask. The flask was connected to the hood by a clamp. Water was then ran through the condenser and connected to the round bottom flask to begin refluxing the contents in the flask. The mixture was gently heated at reflux for one hour.
Ensure gloves are worn at all times when handling strong acids and bases within the experiment of the preparation of benzocaine. 4-aminobenzoic acid (3.0g, 0.022 moles) was suspended into a dry round-bottomed flask (100cm3) followed by methylated sprits (20 cm3). Taking extra care the concentrated sulphuric acid of (3.0 cm3, 0.031 moles) was added. Immediately after the condenser was fitted on, and the components in the flask were swirled gently to mix components. It should be ensured that the reactants of the concentrated sulphuric acid and the 4-aminobenzoic acid were not clustered in the ground glass joint between the condenser itself and the flask. In order to heat the mixture to a boiling point, a heating mantle was used and then further left for gently refluxing for a constituent time of forty minutes. After the duration of the consistent forty minutes the rou...
Alkylated phenols and their derivatives are important materials in both organic synthesis and chemical manufacturing. Mono-alkylphenols and di-alkylphenols are used as raw materials for the manufacture of a wide variety of products such as resins, wire enamels, varnishes, printing inks, antioxidants, flame retardants, ultraviolet absorbers, fungicide, petroleum additives and rubber chemicals [1-17]. Friedel–Crafts alkylation of phenol with tert-butyl alcohol (TBA) produces 2-tert-butylphenol (2-TBP), 4-tert-butylphenol (4-TBP), 2,4-di-tert-butylphenol (2,4-DTBP), 2,6-di-tert-butylphenol (2,6-DTBP) and tert-butylphenol ether (TBPE), depending on both the catalyst and the reaction conditions. Based on previous researches, it is well known that moderate acid catalysts or high reaction temperature led to carbon alkylated products and TBPE is produced in the presence of weak acidic catalysts as a major product. 2-TBP is the jarless product of alkylation of phenol with TBA owing to the presence of phenolic (–OH) group on the aromatic ring that kinetically favours o-alkylation. However, due to steric hindrance, thermodynamically unfavoured o-isomer (2-TBP) is readily isomerized into less hindered p-isomer (4-TBP), especially in moderate acidic media. If strong acid catalysts are used in the alkylation reaction, 2,4-DTBP is a dominant product [17,18]. 2,4-DTBP is used in the manufacture of its triphosphite and benzotriazole, which are employed as a co-stabilizer for PVC or UV absorbers in polyolefins [12,13]. 2-TBP is an intermediate for pesticides, fragrances and antioxidants [14]. High selectivity toward 4-TBP is favored since this product imparts enhanced properties to the class of metallic detergents (phenates) used in lubricating oil...
The Olefins II Unit makes hydrocarbons from naphtha or natural gas using furnaces. After distillation, the p...
The isoborneol produced through this redox reaction was the kinetic product. This kinetic product was less stable, yet it was produced because of the low amount of energy supplied for the reaction. In the formation of isoborneol the hydride ion attacks the carbonyl carbon of camphor on the least hindered site. With more energy the molecules have more effective collisions on the opposite side. With the energy supplied in this reaction, there would be too much steric effect inhibiting the hydride ion from attacking the carbonyl carbon to make the more stable thermodynamic product borneol.
Methyl ethyl ketone is one of the top 100 chemicals produced worldwide due to its high demand and versatile end use. This paper will analyze and compare the production processes of methyl ethyl ketone using patent protected methods of two of the industry’s chemical production leaders, Maruzen Petrochemical Co. and ExxonMobil Corp. The analysis of the two methyl ethyl ketone production methods will enable us to bring to light the evolution of the production process over time and the impact which these processes have on energy consumption and waste production. By comparing the patent protected method for producing methyl ethyl ketone of world’s leading producer of methyl ethyl ketone, Maruzen Petrochemical Co., with ExxonMobil Corp.’s patented method, and the conventional method we will be able to determine the more favorable process based on their impact on the environment, turnover time, and energy consumption.
The catalytic process occurs at lower temperature anf offers higher selectivity but requires frequent regeneration of the catalyst. Then, the products are cooled and introduced into a pair of separators which separate the unreacted hydrogen. The unreacted hydrogen is compressed and recycle back to the feed and reactor. The products that leaving the separators are heated before introduced into a distillation column which the toluene is separated from the stream and recycle back to the...