Oxidation of Cyclohexanone to Adipic Acid

Better Essays
April Goodson
CHEM 242L-002
February 20, 2013

Oxidation of Cyclohexanone to Adipic Acid
Abstract
The cyclic ketone cyclohexanone was oxidized to adipic acid using the oxidizing agent nitric acid. The experiment yielded 0.2667 grams of adipic acid, giving a percent yield of 113.97%. Although the product was allowed to dry for one week, residual moisture was still present in the sample and a melting point could not be obtained. This error in the experiment either resulted from adding too much water or not allowing the product to remain in the Hirsch vacuum filtration for long enough to sufficiently dry.
Introduction
Redox reactions are an important class of reactions in organic chemistry that involve the transfer of electrons from one molecule to another. This experiment focused on an oxidation reaction. In organic chemistry, oxidation reactions occur when a carbon atom becomes bonded to a more electronegative atom, causing the electron density on the carbon atom to decrease (McMurray, 2012). Examples of oxidation reactions in organic chemistry are the breaking of a carbon-hydrogen bond, or the formation of a carbon-oxygen bond (McMurray, 2012). This reaction oxidized a secondary alcohol to a ketone (Williamson, 2003). The oxidation of a ketone, in this case, cyclohexanone, can be accomplished by using various oxidizing agents, however, this experiment made use of the powerful oxidizing agent nitric acid. An intermediate is formed during this oxidation, which is further oxidized to adipic acid (Figure 1) (Williamson, 2003). This reaction is of particular importance, as it breaks the cyclic carbon ring when adipic acid is formed (Williamson, 2003).
The ketone reagent used in this experiment was cyclohexanone, a cyclic six-carbon ring with an attached oxygen group (Figure 1). Cyclohexanone is an oily clear liquid at room temperature. Cyclohexanone is known to have the molecular formula, C6H10O, a molecular weight of 98.14 grams/mole, a melting point of -47



References: Gaivoronskii AN, Granzhan, VA (2005). Solubility of Adipic Acid in Organic Solvents and Water. Russian Journal of Applied Chemistry. 78 pp 404-408. McMurray, JM (2012). Organic Chemistry, 8th Edition. CENGAGE Learning. Williamson, KL (2003). Macroscale and Microscale Organic Experiments, 4th Edition. Houghton Mifflin Custom Publishing. PubChem.com (2012). National Center for BioTechnology Information. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=944&loc=ec_rcs Accessed February 20, 2013.

You May Also Find These Documents Helpful

  • Satisfactory Essays

    Adipic Acid

    • 335 Words
    • 2 Pages

    1999 Adipic Acid (98/99-3) Currently operating commercial production processes for adipic acid depend on the production or purchase of KA oil (a mixture of cyclohexanone, the ketone or K component, and cyclohexanol, the alcohol or A component), or of pure cyclohexanol, and its subsequent oxidation in solution to adipic acid using an excess of strong nitric acid. This report deals with KA oil/cyclohexanol production by various routes, followed by the common step of nitric acid oxidation. KA oil…

    • 335 Words
    • 2 Pages
    Satisfactory Essays
  • Powerful Essays

    Adipic acid

    • 3850 Words
    • 16 Pages

    N2O EMISSIONS FROM ADIPIC ACID AND NITRIC ACID PRODUCTION A C K N O WL E D G E M E N T S This paper was written by Heike Mainhardt (ICF Incorporated) and reviewed by Dina Kruger (USEPA). ABSTRACT Nitrous oxide (N2O) is generated as a by-product during the production of adipic acid and nitric acid. The main use for adipic acid is as a component of nylon-6/6; thus production trends are closely correlated with nylon consumption trends. Worldwide, there are very few adipic acid plants. The U.S…

    • 3850 Words
    • 16 Pages
    Powerful Essays
  • Powerful Essays

    Synthesis of Adipic Acid

    • 1681 Words
    • 7 Pages

    Experiment 8: Synthesis of Adipic Acid Performed November 8th & 10th By Jennifer Seitz Organic Chemistry 344 Section 803 Fall 2011 Objective: The purpose of this experiment was to synthesize adipic acid from cyclohexanol via an oxidation reaction that was catalyzed by sulfuric acid. Purity of the product was assessed by measuring the melting point. Physical Properties/Structures: Name | Formula | Molecular Weight (g/mol) | Boiling Point (0C) | Melting Point(0C) | Density(g/mL)…

    • 1681 Words
    • 7 Pages
    Powerful Essays
  • Better Essays

    Synthesis of Adipic Acid

    • 2491 Words
    • 8 Pages

    Affects of Hydrogen Peroxide Equivalents on Green Synthesis of Adipic Acid. Andrew R. Glessman*, Chase W. Turner, Audra Cokain, Jacob Kindred, Darryl Watkins Department of Chemistry and Chemical Biology, IUPU, 402 N. Blackford St, Indianapolis, IN 46202 aglessma@umail.iu.edu April 25, 2014 Figure _______________________________________________________________Abstract- The synthesis of adipic acid has been a growing topic of discussion due to the harmful impact it has on the environment…

    • 2491 Words
    • 8 Pages
    Better Essays
  • Good Essays

    Oxidation

    • 603 Words
    • 3 Pages

    Amber Lamb and Stephonya Williams EXPERIMENT TITLE: Oxidation: Cyclohexanone from Cyclohexanol by Hypochlorite Oxidation and Adipic Acid from Cyclohexanone DATE: 4/18/2014 INTRODUCTION: In experiment 4, alcohol is oxidized to a ketone with household bleach. The product is then isolated by steam distillation and is extracted into the distillate with ether. After the removal of ether, it leaves the product cyclohexanone. In experiment 6, cyclohexanone is oxidized by potassium permanganate. Manganese…

    • 603 Words
    • 3 Pages
    Good Essays
  • Good Essays

    OXIDATION OF CYCLOHEXANOL TO CYCLOHEXANONE The oxidation of cyclohexanol to cyclohexanone involves the removal of hydrogen from the OH group. After separation and purification, an Infrared Spectrum will be run to determine the composition of the recovered material. Infrared Spectroscopy is a very powerful technique used in the determination of molecular structure and the identification of unknown organic materials. The infrared spectrum yields direct…

    • 954 Words
    • 4 Pages
    Good Essays
  • Good Essays

    Acidity’s effects on Fruit Browning Aim: To test whether the acidity of the surface area of an apple has an effect on the rate of enzymatic browning over 70 minutes. Hypothesis: the more acidic the surface area the longer it takes for the fruit to oxidise. Variables: Independent: acidity of surface area of the apple Dependent: the progression of melanin (brown pigment) after 70 minutes Controlled/fixed: time of day, knife used to cut fruit, portion of fruit, environment…

    • 1040 Words
    • 5 Pages
    Good Essays
  • Powerful Essays

    Oxidation of Cyclohexanol

    • 1707 Words
    • 8 Pages

    Oxidation of Cyclohexanol Introduction: The oxidation of cyclohexanol involves using household bleach to oxidize this secondary alcohol and produce a ketone product, cyclohexanone. Oxidation-reduction (redox) reactions occur when the oxidation state of atoms change due to a transfer of electrons. Oxidation occurs when electrons are ‘lost’ to the formation of bonds and reduction occurs when electrons are ‘gained’ in the braking of bonds (Levine). Using this reaction and its product, a redox experiment…

    • 1707 Words
    • 8 Pages
    Powerful Essays
  • Satisfactory Essays

    ethyl ketone, methanol, ethanol, isopropanol [1] • Sparos P. Nemphos and Robert L. Walter - Cyclohexanone, methyl ethyl ketone, methanol, dimethylformamide[2]. • Harry Gilbert, Cuyahoga Falls- With an inert solvent or diluent such as benzene, toluene, trichlorobenzene The copolymers which are prepared according to this invention are characterized by being soluble in dimethyl formamide, hot cyclohexanone, and in a mixture of dimethyl formamide and acetone. They are insoluble in acetone alone, alcohol…

    • 213 Words
    • 1 Page
    Satisfactory Essays
  • Satisfactory Essays

    Oxidation

    • 480 Words
    • 2 Pages

    Experiment 39 Oxidation – Reduction Titrations II : Analysis of Bleach A. Standardization of 0.05 M Na2S2O3 Solution KIO3 concentration 0.01 M Volume of KIO3 Trial #1 Trial #2 Final burette reading 15.01 mL 30.00 mL Initial burette reading 0.00 mL 15.01 mL Milliliters of KIO3 used 15.01 mL 14.99 mL Volume of Na2S2O3 Trial #1 Trial #2 Final burette reading 13.40 mL 25.78 mL Initial burette reading 0.03 mL 13.37 mL Milliliters of Na2S2O3 used…

    • 480 Words
    • 2 Pages
    Satisfactory Essays