Process Chemistry – Outcome 2
Acetone
Blair Holman
13/12/2017
Contents
Industrial Synthesis
Main Uses
Demand
Origins
Availability
Cost
Environmental Impact
Industrial Synthesis
Acetone is an organic compound with the formula (CH3)2CO. Acetone is the simplest Ketone which is Propan-2-one. Acetone can be produced using different methods which are the Cumene Process, From Alkane nitriles, the hydrolysis of Gem-Dihalides, the Oxidation of Isopropyl Alcohol, the Ozonolysis of Alkenes and the Fermentation Process.
Cumene Process – The process was invented by Heinrich Hock in 1944 and also independently by R. Udris and P.Sergeyev in 1942. This process uses to relatively cheap base starting materials
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Some of which are that it a very good solvent in the process of making many plastics and certain synthetic fibres. Also used to thin polyester resin, cleans tools used with it, dissolves two-part epoxies and superglue before they harden. Used as one the volatile components of some paints and varnishes. It is useful for preparing metal before it gets painted. It is also useful for high reliability soldering applications to remove rosin flux after soldering is complete it also helps to prevent the rusty bolt effect. Acetone is used as a solvent by a pharmaceutical industry and as a denaturant in denatured alcohol. It is also present as an excipient in some pharmaceutical drugs.
As chemical intermediate acetone is used to synthesize methyl methacrylate(CH3)2C(OH)CN + CH3OH → CH2=(CH3)CCO2CH3 + NH3
The third major use of acetone (about 20%) is synthesizing bisphenol A. Bisphenol A is a component of many polymers such as polycarbonates, polyurethanes, and epoxy resins. The synthesis involves the condensation of acetone with phenol:(CH3)2CO + 2 C6H5OH → (CH3)2C(C6H4OH)2 + H2O
Many millions of kilograms of acetone are consumed in the production of the solvents methyl isobutyl alcohol and methyl isobutyl ketone. These products arise via an initial aldol condensation to give diacetone alcohol. 2 (CH3)2CO →
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Membrane damage, a decrease in size and decrease in germination of various agricultural and ornamental plants is damage acetone has caused. The effects acetone has on birds and land animals has not been completely determined but it is not expected to bioaccumulate in plants, animals or humans. It occurs naturally in the environment but industrial processes contribute more acetone to the environment than the natural processes. It is mainly emitted to air and it can move from being in the atmosphere into water through rain and snow and then quickly back into the air. It quickly degrades in soil within days. It quickly evaporates into a gas if released as a liquid. It degrades in sunlight to other chemicals with the half of life of it being approximately 22 days. It does not bind to the soil or bioaccumulate in animals. Microorganisms in the soil and the water are capable of degrading acetone. There are currently no environmental guidelines for
At this point I found that if the hot plate was at 147˚C the solution boiled more vigorously, meaning that my ketone hade a boiling point of 147˚C, which was close to the known boiling point value for 3-heptanone , 146˚C. The hot plate was turned down after this was noticed. After the solution was heat, approximately for five minutes, the mass was found for the bottom layer, which was 2.27g, and the percent yield was calculated. The percent yield was determined by taking the mass of the final ketone and dividing it by the original mass of the alcohol.
Tyler White CHEM151LL 32658 04/01/2018 Different Types Chemical Reaction Types and Equations Purpose: The purpose of this lab experiment is to examine different types of chemical reactions such as Decomposition reaction, Synthesis reactions, Combustion reactions, and different Chemical equations. The experiments were conducted online using Late Nite Labs. Materials: Because the experiments were conducted online there wasn’t any physical use of materials, only digital ones, for these labs to be performed. Only the registration for the website was needed to perform these online labs, as well as a desktop computer.
Dalia El-Desoky Organic Chemistry II Lab 05 8 February 2017 Dehydration of 2-methylcyclohexanol Introduction: Dehydration is a common reaction in Organic Chemistry used to produce carbon-carbon double bonds. The dehydration mechanism involves the removal of water from an alcohol to form an alkene. In this experiment, 2-methylcyclohexanol will undergo acid catalyzed dehydration in heat to form three products: 1-methylcyclohexene, 3-methylcyclohexene, and methylenecyclohexane [1]. The reaction is carried out in a Hickman still filled with Drierite, a drying agent composed of CaSO4 which absorbs water.
This also means that the impurity, 1, 4-dibromobenzene, was not probably extracted completely; it should have been removed during vacuum filtration. However, all the steps for carrying out the extraction of the neutral compound was successful; there were no complications. The error must have occurred during the crystallization procedure. 95% Ethyl alcohol was used as the solvent to dissolve the
It often is used as a sweetener for diabetic food and this is because it is poorly absorbed in the intestines so as to not spike insulin levels. This is because it has a higher heat of solution than most sugar alcohols and it has low solubility that is found in candies and such. It can also be used in medicine. It can be used to for glaucoma and can be used to lower intracranial pressure. If it used as a medication it is often given in injection form.
The reaction to synthesize benzocaine was known as a Fisher esterification reaction. The Fisher esterification was reaction between alcohol and carboxylic acid in the presence of acid. The reaction was used to form an ester. In the experiment, sulfuric acid acted as a catalyst and necessary for this reaction to occur. There was a change between the –OH group of carboxylic acid to an –OCH2CH3 group in the reaction.
The product obtained was (2S, 3R)-2, 3-dibromo-3-phenylpropanoic acid and (2R, 3S)-2, 3-dibromo-3-phenylpropanoic acid, which are enantiomers. This was determined through melting point analysis. The melting point range for the product was 198 to 202 degrees Celsius, which is a lot close to the given melting point of the anti-addition product, 202-204 degrees Celsius. The given melting point range was 93.5-95 degrees Celsius. Furthermore, the syn-addition product is unlikely and difficult to produce due to stereochemistry selectivity.
Abstract: The purpose of this experiment was to identify given Unknown White Compound by conducting various test and learning how to use lab techniques. Tests that are used during this experiment were a flame test, ion test, pH test, and conductivity test. The results drawn from these tests confirmed the identity of the Unknown White Compound to be sodium acetate (NaC2H3O2) because there were no presence of ions and sodium has a strong persistent orange color. The compound then will be synthesized with the compounds Na2CO3 and HC2H3O2 to find percent yield.
The purpose of this experiment was to learn about metal hydride reduction reactions. Therefore, the sodium borohydride reduction of the ketone, 9-fluorenone was performed to yield the secondary alcohol, 9-fluorenol. Reduction of an organic molecule usually corresponds to decreasing its oxygen content or increasing its hydrogen content. In order to achieve such a chemical change, sodium borohydride (NaBH4) is used as a reducing agent. There are other metal hydrides used in the reduction of carbonyl groups such as lithium aluminum hydride (LiAlH4).
The decomposition of NaHCO3 is an example of Prevention within Green Chemistry principles because all solid waste in this experiment is collected and used again. The only gaseous wastes generated by the reaction in the experiment are carbon dioxide and water, which are benign (Lab 3). The decomposition reaction of NaHCO3, generates virtually no waste, therefore less hazardous chemical syntheses. The byproducts of the reaction are gaseous CO2 and H2O which possess little or no toxicity to human health and the environment, because of the amounts released in this experiment. (Lab 3).
The objective of this two-part experiment was to in Part I, create 4-tert-butylcyclohexanone via oxidation of 4-tert-butylcyclohexanol to provide a source of ketone for reduction procedures. Part II of the experiment was conducted preforming a series of reduction reactions in effort to asses the diastereoselectivity of aluminum isopropoxide (MPV reduction), sodium borohydride (NaBH4), and L-selectride when reacted with 4-tert-butylcyclohexanone. The methods used for analysis were TLC, IR, and 1HNMR spectroscopy. An oxidation of 4-tert-butylcyclohexanol was conducted to produce the ketone, 4-tert-butylcyclohexanone using oxidizing reagent, sodium hypochlorite in glacial acetic acid solvent.
Results 8. The obtained product was 4-tert-butylbenzyl phenol ether. This leads the unknown compound # 51 to be tert-butyl phenol. 9. Theoretical yield =
This supports the isolated product is majority made of the desired product and is largely pure. Mass spectrometry of the crude product shows the molecular ion peak is 162.1, which is the largest fragment in the mass spectrum (Figure 4) and corresponds to the molecular weight of methyl trans-cinnamate (Table 1). The base peak is 131, inferring the fragment lost is 31 m/z in size. This 31 m/z matches the OCH3 fragment of the ester, and would not result from a trans-cinnamic acid. This is evidence the product was successfully
Then percent yield was calculated to be 67.57%. The isolation of less product resulted from using less amount of acetanilide than 0.07g at the beginning of the experiment. In addition, the melting point of the product was measured to be 164.8-168.50c, which is in the range of the normal melting point of 4-bromoacentailide, 165-1690c. This confirmed the formation of 4-bromoacetanilide from the bromination of acetanilide. From the bromination of 0.05g aniline, 0.156g of the product was collected.
Purpose/Introduction The process of recrystallization is an important method of purifying a solid organic substance using a hot solution as a solvent. This method will allow the separation of impurities. We will analyze Benzoic Acid as it is dissolved and recrystallized in water and in a solvent of Methanol and water. Reaction/Summary