Synthetic method of L-dibenzoyl tartaric acid

A technology of benzoyl tartaric acid and benzoyl tartaric anhydride, which is applied in the field of chemical synthesis of chiral separation reagents, can solve the problems of low utilization rate of raw materials, cannot be recycled, and low product purity, and achieves convenient manipulation and low cost. , Improve the yield of finished products and the effect of product quality

Active Publication Date: 2015-04-08
濮阳天健生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The defect of common synthetic method is: 1. raw material has strong irritation, strong corrosiveness, hypertoxicity, is difficult to handle
② The utilization rate of raw materials is low, they cannot be recycled, and the production pollution is relatively large
③ The process yield is low, about 50%, the product purity is low, and the production cost is high

Method used

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  • Synthetic method of L-dibenzoyl tartaric acid
  • Synthetic method of L-dibenzoyl tartaric acid
  • Synthetic method of L-dibenzoyl tartaric acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] A kind of synthetic method of L-dibenzoyl tartaric acid, it comprises the steps: get L-tartaric acid 150g, toluene 200ml is placed in 1000ml there-necked bottle, add 1g copper sulfate under stirring, start to drop 300g of benzoyl chloride, drop in 2 hours Finished, continue to react for 4 hours, put the material into the centrifuge, and get 442.5g of L-dibenzoyl tartaric anhydride by shaking filter, put it into a 2000ml three-necked bottle, add 442.5g of water and toluene, heat up to reflux, keep for 3 hours, cool down Blowing to normal temperature, rejection filter to get 345.3g of L-dibenzoyl tartaric acid,

[0036] The L-dibenzoyl tartaric acid that present embodiment obtains is carried out TEM test, test structure such as figure 1 Shown, as can be seen from the figure, the purity content of finished product L-dibenzoyl tartaric acid is 99.47%, and the total yield is 95.4%.

[0037] Peak number Peak name Retention time Peak height Peak area Content

[0038] 1 2.620...

Embodiment 2

[0048] A kind of synthetic method of L-dibenzoyl tartaric acid, it comprises the steps:

[0049] Put 1.5kg of L-tartaric acid and 2L of toluene into a 10L three-necked bottle, add 10g of copper sulfate under stirring, start to add 3.5kg of benzoyl chloride dropwise, finish dropping in 2.5 hours, continue to react for 4 hours, discharge the material into a centrifuge, and shake off to obtain Put 4.41kg of L-dibenzoyl tartaric anhydride into a 20L three-necked bottle, add 4.41kg each of water and toluene, heat up to reflux, keep for 3 hours, cool down to normal temperature and discharge, shake off to obtain 3.49 kg of L-dibenzoyl tartaric acid kg.

[0050] The L-dibenzoyl tartaric acid that present embodiment obtains is carried out TEM test, test structure such as figure 2Shown, as can be seen from the figure, the purity content of finished product L-dibenzoyl tartaric acid is 99.09%, and the total yield is 96.1%.

[0051] Peak number Peak name Retention time Peak height Peak...

Embodiment 3

[0065] A kind of synthetic method of L-dibenzoyl tartaric acid, it comprises the steps:

[0066] Put 7.5kg of L-tartaric acid and 10L of toluene into a 50L reactor, add 40g of copper sulfate under stirring, start to add 17kg of benzoyl chloride dropwise, finish dripping in 3.5 hours, continue to react for 4 hours, discharge the material to a centrifuge, and shake off to obtain L - 21.4 kg of dibenzoyl tartaric anhydride, put it into a 100L reactor, add 21.4 kg of water and toluene each, heat up to reflux, keep for 3 hours, cool down to normal temperature and discharge, and filter to obtain 17.6 kg of L-dibenzoyl tartaric acid .

[0067] The L-dibenzoyl tartaric acid that present embodiment obtains is carried out TEM test, test structure such as image 3 Shown, as can be seen from the figure, the purity content of finished product L-dibenzoyl tartaric acid is 99.37%, and the total yield is 97.2%.

[0068] Peak number Peak name Retention time Peak height Peak area Content

[...

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Abstract

The invention discloses a synthetic method of L-dibenzoyl tartaric acid. The synthetic method comprises the following steps: with L-tartaric acid and benzoyl chloride as raw materials, copper sulfate as a catalyst and toluene as a solvent, carrying out reaction to prepare L-dibenzoyl tartaric anhydride, carrying out hydrolysis with an equal amount of water and toluene to obtain the L-dibenzoyl tartaric acid, wherein the toluene serving as the solvent, as well as the water and the toluene in the hydrolysis step can be repeatedly utilized. With the adoption of the synthetic method, the process is simple, the operation is safe and easy, the process recovery ratio achieves above 95 percent, meanwhile, the cost of the raw materials is low, a part of the raw materials can be recovered and recycled, and a finished product is high in purity and excellent in chiral separation performance.

Description

technical field [0001] The invention relates to the technical field of a chemical synthesis method of a chiral resolution reagent, in particular to a synthesis method of L-dibenzoyltartaric acid. Background technique [0002] L-dibenzoyl tartaric acid is a white crystalline powder, odorless, slightly bitter taste, slightly soluble in water, pH value is 3-4, acidic, soluble in organic solvents such as ethanol and acetone. Widely used in chiral resolution of racemic amine compounds. And because of its low price, stable properties, and easy recycling, it has good industrial application value. Its molecular formula is as follows: [0003] [0004] The defect of common synthetic method is: 1. raw material has strong irritation, strong corrosiveness, hypertoxicity, is difficult for handling. ② The utilization rate of raw materials is low, they cannot be recycled, and the production pollution is relatively large. ③The process yield is low, about 50%, the product purity is lo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/29C07C69/78
CPCC07B2200/07C07C67/297C07D307/56C07C69/76
Inventor 楚静波刘航崔飞李志军崔清海张道伟李亚敏王建勋李荣范卫彬郑记栓袁国龙文教刚张建民
Owner 濮阳天健生物科技有限公司
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