Síntesis de Ácido Acetilsalicílico y Acetanilida, Ejercicios de Química Orgánica

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UNIVERSIDAD CATÓLICA DE SANTA MARÍA FACULTAD DE CIENCIAS FARMACÉUTICAS, BIOQUÍMICAS Y BIOTECNOLÓGICAS ESCUELA PROFESIONAL DE FARMACIA Y BIOQUÍMICA 6504232 | QUÍMICA ORGÁNICA II – 08 PRÁCTICA N°11 IV SEMESTRE – III FASE TEMA Preparación de Acetato de Etilo INTEGRANTES Coaquira Mamani, Marilia Mileydi Huaylla Chuctaya, María Elena Lazarte Najarro, Kadiha Belen Sulca Berrios, Alder Andres DOCENTE Medina Cabrera, Edilberto Vicente Arequipa – Perú 2022 PRÁCTICA N°11 PREPARACIÓN DE ACETATO DE ETILO RESUMEN [María Huaylla] En esta práctica se realizó la síntesis del acetato de etilo se utilizó un método muy común para la obtención de ésteres donde se trató un ácido carboxílico (ácido acético glacial) con etanol en un medio ácido como catalizador (ácido sulfúrico concentrado) es importante este catalizador ya que favorece la reacción aunque también no podría utilizarse pero la reacción sería demasiado lenta, seguidamente se dejó por 30 min en el reflujo según el tiempo desmontarlo y realizar un montaje para destilación fraccionada procediendo a la destilación tomando el tiempo y la temperatura (70 y 90°C) de los vapores de destilación y con ayuda del de carbonato de sodio al 5% se eliminó restos de etanol, ácido acético y ácido sulfúrico provenientes de la reacción, en seguida se obtuvo las dos fases y se dreno la capa inferior (acuosa) y finalmente como producto final el resultado fue la obtención de acetato de etilo, un derivado del ácido carboxílico. Palabras claves: Acetato de etilo, ácido carboxílico, ácido sulfúrico, destilación fraccionada. ABSTRACT [María Huaylla] In this practice, the synthesis of ethyl acetate was carried out, a very common method was used to obtain esters where a carboxylic acid (glacial acetic acid) was treated with ethanol in an acid medium as a catalyst (concentrated sulfuric acid). This catalyst is important since it favors the reaction although it could not be used but the reaction would be too slow, then it was left for 30 min at reflux depending on the time, disassemble it and carry out an assembly for fractional distillation proceeding to the distillation taking the time and temperature (70 and 90 °C) from the distillation vapors and with the help of 5% sodium carbonate, traces of ethanol, acetic acid and sulfuric acid from the reaction were eliminated, immediately the two phases were obtained and the lower layer was drained ( aqueous) and finally as a final product the result was the obtaining of ethyl acetate, a derivative of carboxylic acid. Keywords: Ethyl acetate, carboxylic acid, sulfuric acid, fractional distillation. – 2 – Step N°3: Fractional distillation. [Figure 3] ーGo through fractional distillation (it helps us to make it more closed / limited). ーRecord time and temperature of distillation vapors. ○ Temperature 30°C: While heating. ○ Temperature 50°C: It begins to condense. ○ Temperature 60°C: It begins to distill. ○ Temperature 70°C: It should stop. ○ Temperature 63°C: The dripping begins, that is what you want to obtain. Approximate temperatures, the temperature of 63°C was obtained during practice when the drip started. ー Stop the reaction when it reaches between 70°C and 90°C. ーDisassemble a part and wait for it to cool down. Consider the following: ↪ Ethyl acetate (boiling): 77.1°C. ↪ Ethanol (boiling): 78.37°C. ↪ Acetic acid (boiling): 118°C. Figure 3. Fractional distillation equipment. It was used to obtain ethyl acetate, however there were remains of other substances previously added. – 5 – Step N°4: Separation funnel. [Figure 4] ー Place what was obtained in a 100 mL separatory funnel. ーWash with 50 mL (5 mL) of 5% sodium carbonate solution. ○ Removes traces of ethanol, acetic acid and sulfuric acid from the reaction. ○ The mixing and the opening of the nozzle are carried out so that there is not much pressure (three times). ー Let the two phases decant and drain the lower layer (aqueous). ーWater is more dense (bottom), the organic phase is the one that is recovered. ○ Density of water: 997 kg/m3. ○ Density of ethyl acetate: 902 kg/m3. ーDry for 30 minutes with an anhydrous salt (10 g of anhydrous sodium sulfate), it remo- ves the water. ー Separate the liquid from the solid carefully. Figure 4. Decantation of the ethyl acetate. It is obtained in the organic phase and with this it is separated from other substances. – 6 – RESULTS [Alder Sulca] Consistent with the given experimentation and the appropriate laboratory process, the result was the obtaining of ethyl acetate, a carboxylic acid derivative, respecting the temperatures and time. As a first preliminary result we can consider the separation of the organic phase and subsequent elimination of the aqueous phase. Second, last and main result is the final obtaining of the COOH derivative after the separation of the liquid. CONCLUSIONS [Alder Sulca] According to the experimental practice experienced in the laboratory, we were able to achieve a result according to our objective. The experimentation did not bring problems or difficulties since the appropriate steps were followed, obtaining a carboxylic acid derivative, that is, we obtained ethyl acetate. Carboxylic acid derivatives must pass through adequate means so as not to spoil the sample, which implies good experimentation by the participants involved in said practice. QUESTIONNAIRE a) Develop reaction mechanisms used in practice. [María Huaylla] It was treated with a carboxylic acid, in this case glacial acetic acid with an alcohol in an acidic medium (dehydrating) sulfuric acid as a catalyst and this also sequesters water molecules. – 7 – Perchlorate, chromium trioxide, fluorine nitrate, dioxygen difluoride, uranium hexafluoride, heptafluoride Iodine, Tetrachlorosilane, Permanganic Acid, Nitric Acid, Hydrogen Peroxide, Acid peroxodisulfur, potassium dioxide, sodium peroxide, potassium permanganate, oxide of ruthenium (VIII), platinum, potassium, potassium t-butoxide, silver oxide and sodium. In general, it is incompatible with acids, acid chlorides, oxidizing agents and reductants and alkali metals. ➤ Products ● Ethyl acetate ○ Physical properties ー Boiling point: 77°C. ー Melting point: –83°C. ー Refractive index: 1,3719 (20°C). ー Density: 0,902 (20°C with respect to water at 4°C), 0,898 (25°C with respect to water at 25°C). ー Explosive limits (% by volume in air): 2,5 – 11,5. ー Vapor density (air = 1): 3. ー Vapor pressure (mmHg): 100 (at 27°C). ー Flash point: –4°C. ー Autoignition temperature: 426°C. ー Solubility: 1 mL is miscible with 10 mL of water (at 25°C), its solubility increases as the temperature decreases. ○ Chemical properties Decomposition products: Carbon monoxide and carbon dioxide. It is generally incompatible with oxidizing agents, bases, acids and moisture. Reacts vigorously – 10 – with acid chlorosulfonic acid, lithium dihydroaluminate, and chloromethyl furan and oleum. Very violent reactions have been reported with lithium tetraaluminate, lithium hydride and aluminum and potassium tertbutoxide. ➤Catalyst ● Sulfuric acid ○ Physical properties ー Physical state, color and odor: Oily liquid, odorless and colorless at normal. Takes a slight spicy smell when hot. ー Odor threshold: 1 mg/m3. ー pH (1 N aqueous solution): 0,3. ー Melting temperature (at 1 atm, 93%): –32°C. ー Molar mass: 98,08 g/mol. ー Boiling point (at 1 atm, 95%): 290°C. ー Vapor pressure (at 146°C): 1 mmHg. ー Vapor density (air = 1): 3,4. ー Liquid density (water = 1): 1,84 (98%). ー Decomposition temperature: 30°C. ー Viscosity (55°C at 98%): 25 cps. ー Other relevant data: Reacts violently with water. ー Solubility in water: 100%. ○ Chemical properties It is a strong oxidizer. It reacts with ordinary metals, such as aluminum, to form sulfates and bisulfates, in addition to releasing hydrogen. When it is concentrated and at high temperature it reacts with carbon, phosphorus and sulfur. – 11 – Furthermore, in this variant it can also react with precious metals. Decomposes salts formed by other acids. c) What are the applications of ethyl acetate? [Marilia Coaquira] The application or uses of ethyl acetate in industrial products. ● Ink products. ● Paint solvents. ● Creation of industrial adhesives derived from cellulose. ● Artificial fruit essences. ● Solvent for explosive compounds. ● Preparation of dyeing in textile products. ● Resin removal. ● Flavoring in cigarettes. ● Solvent in chromatography. ● Solvent in synthesis of vitamin E. ● Reagent in pigment manufacturing. ● Perfume manufacturing. ● Solvent for nitrocellulose, varnishes and lacquers. ● Textile cleaning. Solvent ● Ethyl acetate in the textile industry acts as a cleaning agent. ● It is used to calibrate thermometers. ● It uses it to separate from sugars. ● In the paint industry it is used as an agent to dilute materials. Artificial flavors It is used to give fruit flavors; for example: banana, pear, peach and pineapple, as well as grape aroma, mostly in the cosmetics and food industry. Analytical Ethyl acetate is used for the determination of bismuth, boron, gold, molybdenum and platinum, as well as thallium solvent. – 12 –