Removal of the By-Product Tributyltin Chloride from Reaction Mixtures

Location

CSU

Student's Major

Chemistry and Geology

Student's College

Science, Engineering and Technology

Mentor's Name

Brian Groh

Mentor's Department

Chemistry and Geology

Mentor's College

Science, Engineering and Technology

Description

Tributyltin chloride (C4H9)3SnCI is a troublesome by-product formed in many reactions and is difficult to remove. Current laboratory techniques for the removal of tributyltin chloride from organic by-products are either ineffective or costly. This project's objective is to develop an efficient and cost-effective method to remove tributyltin chloride from organic reaction mixtures. We studied the affects of a variety of fluoride ion sources (KF, KHF2, NH4F) and reaction solvents (hexane, ether and tetrahydrofuran) in the presence or absence of sodium bicarbonate Results indicate that treatment of the reaction mixture with potassium fluoride in the presence of sodium bicarbonate and a nonpolar solvent is the best method. This process converts (C4H9)3SnCI, a liquid, into (C4H9)3SnF, a solid, which may be removed by simple filtration.

PhCOCH2CH, + (C4H9)3SnCl + F (C4H9)3SnF + PhCOCH2CH3

The recovered precipitate, Bu3SnF, may easily be transformed into (C4H9)3SnCl, a useful starting material, rather than be discarded as a hazardous waste. This recycling process for the removal of tributyltin chloride by products may have research and industrial scale applications.

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Removal of the By-Product Tributyltin Chloride from Reaction Mixtures

CSU

Tributyltin chloride (C4H9)3SnCI is a troublesome by-product formed in many reactions and is difficult to remove. Current laboratory techniques for the removal of tributyltin chloride from organic by-products are either ineffective or costly. This project's objective is to develop an efficient and cost-effective method to remove tributyltin chloride from organic reaction mixtures. We studied the affects of a variety of fluoride ion sources (KF, KHF2, NH4F) and reaction solvents (hexane, ether and tetrahydrofuran) in the presence or absence of sodium bicarbonate Results indicate that treatment of the reaction mixture with potassium fluoride in the presence of sodium bicarbonate and a nonpolar solvent is the best method. This process converts (C4H9)3SnCI, a liquid, into (C4H9)3SnF, a solid, which may be removed by simple filtration.

PhCOCH2CH, + (C4H9)3SnCl + F (C4H9)3SnF + PhCOCH2CH3

The recovered precipitate, Bu3SnF, may easily be transformed into (C4H9)3SnCl, a useful starting material, rather than be discarded as a hazardous waste. This recycling process for the removal of tributyltin chloride by products may have research and industrial scale applications.