Method for recycling and reusing L-(+)-tartaric acid in production of D-p-methyl sulfone phenyl ethyl serinate

A technology of tartaric acid and calcium tartrate, which is applied in the chemical field, can solve the problems that the product quality of L-(+)-tartaric acid cannot meet the split requirements, fail to meet the quality standard, and the product quality is poor, so as to achieve easy control and avoid side effects. Response, the effect of reducing production costs

Active Publication Date: 2015-02-18
兰州鑫隆泰生物科技有限公司
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  • Abstract
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Problems solved by technology

[0015] It has been reported in the literature that methanol and ethanol are used as organic solvents to prepare L-(+)-tartaric acid, but the added calcium chloride reacts with the solvent to form CaCl2 ·4CH3OH, CaCL2·4C2H5OH and other complex impurities , even under strong acid catalysis and a certain temperature, impurities such as L-(+)-dimethyl tartrate and L-(+)-diethyl tartrate are formed. Then most of the impurities are always present in the L-(+)-tartaric acid, causing the quality of the recovered L-(+)-tartaric acid product to fail to meet the resoluti

Method used

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  • Method for recycling and reusing L-(+)-tartaric acid in production of D-p-methyl sulfone phenyl ethyl serinate
  • Method for recycling and reusing L-(+)-tartaric acid in production of D-p-methyl sulfone phenyl ethyl serinate

Examples

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Example Embodiment

[0045] Example 1

[0046] Production of L-(+)-tartaric acid from L-(+)-diammonium tartrate from mother liquor of D-ethyl ester

[0047] In a 5000L glass-lined reactor, add pure water, turn on the stirring, add the separated D-ethyl ester·L-(+)-tartrate, add dropwise ammonia to adjust PH=7~8 to obtain D-ethyl ester product And the mother liquor containing L-(+)-diammonium tartrate.

[0048] In a 5000L glass-lined reactor, add L-(+)-diammonium tartrate aqueous solution, stir, add hydrochloric acid dropwise to adjust pH=3.4 (control pH=3.3-3.6), cool, and control the temperature not to exceed 10-30℃. Freeze cooling to 10°C for crystallization, centrifugation, cold water washing, and drying to obtain high-purity L-(+)-ammonium hydrogen tartrate white crystals.

[0049] In a 5000L glass-lined reactor, add 3000~4000kg organic solvent acetone, stir, cool down to ≤10℃, add 500~1000kg of L-(+)-ammonium hydrogen tartrate solid, cool down, and control the temperature in the kettle to ≤10 ℃, ...

Example Embodiment

[0053] Example 2

[0054] Production of L-(+)-tartaric acid from L-(+)-calcium tartrate from mother liquor of L-ethyl ester

[0055] L-(-)-p-methylsulfonyl phenylserine ethyl ester·L-(+)-tartrate methanol solution was concentrated under reduced pressure to recover methanol, and water was added to obtain L-(-)-p-methylsulfonyl phenylserine ethyl ester·L The -(+)-tartaric acid aqueous solution is neutralized and freed by alkaline substances, and calcium chloride solid is added to react to form L-(+)-calcium tartrate crystals, which are cooled, separated and washed to obtain L-(+)-calcium tartrate crystals.

[0056] In a 5000L calcium tartrate recovery kettle, add D-ethyl ester free mother liquor or L-ethyl ester free mother liquor into the recovery kettle, inject 70-80% of the liquid level, turn on the stirring; add high-purity calcium chloride solids in batches to react Generate L-(+)-calcium tartrate crystals, cool to 10~25°C to crystallize and centrifuge to obtain L-(+)-calcium t...

Example Embodiment

[0061] Example 3

[0062] Application and separation of recovered L-(+)-tartaric acid

[0063] Add 2200~3000kg of anhydrous methanol to the 5000L separation kettle, add 220Kg of L-(+)-tartaric acid recovered by the above process, heat it up, keep it at 25~35℃ for 30min~60min, wait until the L-(+)-tartaric acid is complete Dissolve and prepare for later use; add the prepared 400Kg DL-(±)-p-methylsulfonylphenylserine ethyl ester methanol solution into the separation kettle, stir for 40-60min, heat up to 45~66℃, reflux, keep for 30~60min ; After the reaction is completed, cool down to 28~33℃, ready to press filter;

[0064] At the same time, the diaphragm filter press is preheated in advance to about 28~33℃ and kept warm. When the separation kettle is cooled to about 28~33℃, the material is discharged to the filter press for pressure filtration. After discharging, it is pressed, D-(+)-p-methylsulfonylphenylserine ethyl ester·L-(+)-tartaric acid crude salt was obtained by compressed...

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Abstract

The invention discloses a method for recycling and reusing L-(+)-tartaric acid in production of D-p-methyl sulfone phenyl ethyl serinate. The method comprises the following steps: (1), a L-(+)-calcium tartrate dihydrate crystal is recovered from L-ethyl ester mother liquor; (2), an L-(+)-tartaric acid double brine solution is recovered from D-p-methyl sulfone phenyl ethyl serinate mother liquor; (3), L-(+)-tartaric acid double hydrochlorination is performed; (4), L-(+)-tartaric acid is recovered through L-(+)-tartaric acid single hydrochlorination; and (5), processes of vacuum concentration, crystallization, separation, drying and the like are performed. An insert organic solvent is used for replacing a conventional water phase method to recover L-(+)-tartaric acid, the possibility of side reaction is avoided, the purity and specific rotation of a product can both reach the raw material quality standard, and L-(+)-tartaric acid can be directly and circularly applied to chiral resolution of D-p-methyl sulfone phenyl ethyl serinate. Different recovery processing technologies are adopted for different mother liquor of two components in the production process of D-p-methyl sulfone phenyl ethyl serinate, the product quality is improved remarkably, the whole recovery condition is mild, and the operation is simpler and easy to control.

Description

technical field [0001] The invention belongs to the technical field of chemistry and relates to a method for recovering and applying L-(+)-tartaric acid in the production of D-ethyl ester. Background technique [0002] D-(+)-p-thymphenylphenylserine ethyl ester (referred to as D-ethyl ester) is obtained from DL-(±)-p-thymphenylphenylserine ethyl ester through L-(+)-tartaric acid optical resolution Obtained, the intermediate is an important intermediate for the synthesis of thiamphenicol and florfenicol, especially florfenicol is an excellent broad-spectrum antibiotic for veterinary use, with low toxicity, no residue, and no drug resistance. Because the rapid growth of the amount of florfenicol has driven the growth of the demand for intermediates, therefore, a large amount of L-(+)-tartaric acid needs to be consumed in the D-(+)-ethyl ester generation process. [0003] The chiral substance L-(+)-tartaric acid was used to resolve DL-(±)-p-thiamphenicyl phenylserine ethyl est...

Claims

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Application Information

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IPC IPC(8): C07C59/255C07C51/02C07C317/48C07C315/06
CPCC07B57/00C07B2200/07C07C51/02C07C51/412C07C51/42C07C315/06C07C59/255C07C317/48
Inventor 欧阳建峰黄朝纲张晖孙衍辉孙静丽李明
Owner 兰州鑫隆泰生物科技有限公司
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