Synthesis of the Jacobsen�s Catalyst
Synthesis of the Jacobsen�s Catalyst
Abstract
The synthesis of Jacobsen�s catalyst involves five experiments, each experiment synthesis part of materials that is needed in following experiment. In experiment #1, 0.8259g of (S,S)-tartaric salt was synthesized from 3.7530g of unnatural D-(-)-tartaric acid, the % yield is 38%, using those (S,S)-tartaric salt, in experiment #3 we successfully synthesized 0.7088g of Jacobsen�s Ligand using 0.5524g of (S,S)-tartaric salt, and % yield is 62.01%. The optical purity for Jacobsen�s Ligand is 89.24%, which is very good. At last in experiment 5 total 0.3008 of Jacobsen�s catalyst was synthesized from 0.5036 of Ligand, and % is 51.4%. The quality ...
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is also widely used in industry because only small amount of the catalyst is needed.
The purpose of this experiment is to learn how to synthesis of Jacobsen�s catalyst. The experiment was divided into five parts. It start with purification of unnatural D-(-)-tartaric acid, once purified product (S, S)-1, 2-diaminocyclohexane mono-(-)-tartrate salt was obtained; the experiment moved to next step, which is synthesis of 3, 5-Di-tert-buthl-2-hydroxybenzaldehyde. In this step, 3,5-Di-tert-buthl-2-hydroxybenzaldehyde was synthesis by letting 2,4-di-t-buthylphenol react with hexamethylenetetramine in high temperature and then crystallizes in icy water.
Once we obtained both products from part 1 and part 2 of this experiments, we can moved on to key steps of this experiment, which is synthesis of Jacobsen�s ligand, the quality of final product was depend on the purity of Jacobsen�s ligand. Jacobsen�s ligand is form by letting (S,S)-tartrate salt from part 1 react with potassium ...
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start with 3.7530 g of unnatural D-(-)-tartaric acid and 0.8259g of (S,S)-tartaric salt was synthesized. The theoretical yield of this experiment is 2.1717g, and % yield is 0.8259g/2.1717g = 38%. The % yield was lower than my expectation due to I did hot filtration, which purify sample better but also loss large portion of product (1a).
Table1-1: Theoretical yield calculation for (S,S)-tartaric Salt
3.753g D-(-)-tartaric acid 1g 1 mol (S,S)-tartaric salt 264.38g/mol
(S,S)-tartaric salt 2.1717g(S,S)-tartaric salt
4 114.22 g/mol D-(-)-tartaric acid 1 mol D-(-)-tartaric acid 1g
Synthesis of 3, 5-Di-tert-buthl-2-hydroxybenzaldehyde. The experiment synthesis 3, ...
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"Synthesis of the Jacobsen�s Catalyst." Essayworld.com. April 15, 2011. Accessed December 2, 2024. http://www.essayworld.com/essays/Synthesis-of-the-Jacobsens-Catalyst/98040.
"Synthesis of the Jacobsen�s Catalyst." Essayworld.com. April 15, 2011. Accessed December 2, 2024. http://www.essayworld.com/essays/Synthesis-of-the-Jacobsens-Catalyst/98040.
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