U-M CHEM 216 - Honors Cup Synthetic Proposal

Unformatted text preview:

Honors Cup Synthetic Proposal Expected Yield: 85 % 36 g Expected Yield: 88 % 31 g Expected yield: 90 % 28 gHonors Cup Synthetic Proposal Section: 251 Group Members: Emily Huth, Keyvan Mirsaeedi, Mike Mooney, Chris Worsham Title: Synthesis of Linalool Introduction: Linalool is a fragrance used in many soaps, detergents, massage oils, creams, lotions, and shampoos. It is also a chemical intermediate in the formation of Vitamin E, and acts as an insecticide that is safe to humans.. Annually, approximately 12,000 tons of linalool are produced worldwide, both through natural sources (it is found in many flowers and spice plants) and chemical synthesis. The synthesis here is based on that of the following paper. Semikolenov, V.A.; Ilyna, I.I.; Simakova, I.L. Applied Catalysis 2001, 211, 91-107. Linalool is commonly found in basil, marigold, and citrus plants. Overall synthetic reaction scheme: LinaloolStep 1 Synthetic transformation 1: Experimental 1: Pinane Oxidation Reaction conditions: pinane 50 cc, T = 100°C, Po2 = 4 atm. Under 4 atm of pressure and at 100°C, 50 cc isomeric pinane and excess O2 (g) were mixed to yield cis- and trans-pinane hydroperoxide. Expected Yield: 85 % 36 g Safety, Disposal and Green Issues: Safety: Pinane-hydroperoxide is a stable hydroperoxide. It is recommended that it be stored in a tightly closed container at a temperature below 35°C. None of these chemicals should be ingested. Byproducts: No byproducts other than untransformed pinane. Disposal and Green Issues: All chemicals are safe for basic organic or acid/base waste.Step 2 Synthetic Transformation 2: Experimental 2: Pinane Hydroperoxide (PHP) HydrogenationReaction conditions: T = 20—80°C, PH2 = 1—11 atm, 5%* Pd/C catalyst concentration 0.5—60.0 g/l *originally 4%, but changed to 5% due to commercial availability Hydrogenation of PHP solution under the reaction conditions (see above) yielded cis- and trans- isomers of pinane-2-ol and the byproducts shown below. Expected Yield: 88 % 31 g Safety, Disposal and Green Issues 2: Safety: Palladium can irritate the eyes, but shows no known irritation to the skin. After use, wash hands face thoroughly; protective gloves and glasses should be worn at all times. All of the byproducts can produce mild irritation to the skin, eyes, or lungs, and are flammable. Reaction should be preformed in a hood with safety goggles and gloves. None of these chemicals should be ingested. Byproducts: 1-acetyl-2,2-dimethyl-3-ethylcyclobutane Isopinocamphone Isopinocampheol + verbanol Isoverbanol + verbanone Waste and Green Issues: The palladium should be recovered for later lab reuse. All other chemicals are safe for basic organic or acid/base waste.Step 3 Synthetic Transformation 3: Experimental 3: Pinane-2-ol PyrolysisReaction conditions: T = 480—600°C*, mixture composition: n-butanol/pinane-2-ol = 9/1 mol/mol. *originally only 560°, but linalool formation occurs on this interval Pinane-2-ol transformed in high temperature into the desired product due to the thermal isomerization. Expected yield: 90 % 28 g Safety, Disposal and Green Issues 3: Safety: General fire- and burn-prevention precautions should be taken when reaching such heat. Alcohols are flammable and should be kept away from open flames. Linalool is a mild irritant to human skin. None of these chemicals should be ingested; the alcohols are particularly toxic if swallowed. Byproducts: Untransformed starting pinane-2-ol (cis and trans) C10H16 hydrocarbons Unsaturated five-member cyclic alcohols (2—5%) Disposal and Green Issues: Linalool is toxic to insects, but is otherwise naturally occurring in nature. All chemicals are safe for basic organic or acid/base waste.Overall budget: Chemical Supplier Cost Amt. Needed Total Pinane Aldrich (Fluka) $80.30 / L 50. mL $0.068 / g 42.85 g $2.91 Pd/C $3.53 / g 1.0 g $3.53 Total costs per synthesis: $6.44 References: Experimental 1: Semikolenov, V.A.; Ilyna, I.I.; Simakova, I.L. Applied Catalysis 2001, 211, 91-107. Ancel, J.E.; Maksimchuk, N.V.; Simakova, I.L.; Semikolenov, V.A. Applied Catalysis A: General 2004, 272, 109-114. Experimental 2: Semikolenov, V.A.; Ilyna, I.I.; Simakova, I.L. Applied Catalysis 2001, 211, 91-107. Ancel, J.E.; Maksimchuk, N.V.; Simakova, I.L.; Semikolenov, V.A. Applied Catalysis A: General 2004, 272, 109-114. Experimental 3: Semikolenov, V.A.; Ilyna, I.I.; Simakova, I.L. Applied Catalysis 2001, 211, 91-107. Semikolenov, V.A.; Ilyna, I.I.; Simakova, I.L. Applied Catalysis 2002, 182-183,


View Full Document

U-M CHEM 216 - Honors Cup Synthetic Proposal

Documents in this Course
Exam 2

Exam 2

12 pages

Load more
Download Honors Cup Synthetic Proposal
Our administrator received your request to download this document. We will send you the file to your email shortly.
Loading Unlocking...
Login

Join to view Honors Cup Synthetic Proposal and access 3M+ class-specific study document.

or
We will never post anything without your permission.
Don't have an account?
Sign Up

Join to view Honors Cup Synthetic Proposal 2 2 and access 3M+ class-specific study document.

or

By creating an account you agree to our Privacy Policy and Terms Of Use

Already a member?