Date of Award

1994

Document Type

Thesis

Degree Name

Master of Science in Applied Chemistry - (M.S.)

Department

Chemical Engineering, Chemistry and Environmental Science

First Advisor

Howard David Perlmutter

Second Advisor

Henry Shaw

Third Advisor

Tamara M. Gund

Abstract

Glycols are often used as starting materials for pharmaceuticals. They are currently manufactured by reacting alkenes with organic peroxy acids in organic solutions that contain chlorinated solvents. The aim of this research is to find ways to avoid the use of hazardous organic solvents in the manufacture of pharmaceuticals in order to prevent pollution. Our approach is to find alternative synthetic methods using water as solvent.

Based on literature information, it was decided to determine if the aqueous potassium peroxymonosulfate oxidation of water-immiscible cyclohexene at room temperature can be scaled up to become a new method to manufacture glycols. Acidic (pH⩽1.7) solutions of 2KHSO5.KHSO4.K2SO4 in water produced trans-1,2-cyclohexanediol from cyclohexene. In a vigorously stirred two-phase mixture, 0.44 mmole KHSO5 oxides cyclohexene to nearly 80% diol with no significant byproducts in 2h at room temperature.

The reaction was then scaled-up to one dm3. The mixture of deionized water, cyclohexene, and freshly prepared Oxone solution was stirred at 907 rpm for 2h at room temperature. In order to remove the diol from the water phase, the mixture was treated with Na2SO4 which quantitatively salted Out the diol before extraction with ethyl ether. The extract was dried over MgSO4 and analyzed by GC using an internal standard. Excellent carbon balances were obtained.

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