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 April 20, 2024. http://www.essayworld.com/essays/Synthesis-of-the-Jacobsens-Catalyst/98040.
"Synthesis of the Jacobsen’s Catalyst." Essayworld.com. April 15, 2011. Accessed April 20, 2024. http://www.essayworld.com/essays/Synthesis-of-the-Jacobsens-Catalyst/98040.
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