Method for preparing R-mandelic acid

A technology of mandelic acid and mandelonitrile, which is applied in the field of R-mandelic acid preparation, can solve the problems of polluting the environment, difficulty in removing free enzymes, low utilization rate of raw materials, etc., and achieves production cost reduction, low energy consumption, and low production cost Effect

Inactive Publication Date: 2013-08-21
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main disadvantages of this method are: ① the nitrilase used is a free enzyme, which is not immobilized and can only be used once, which increases the production cost; ② the utilization rate of raw materials is low, which is not conducive to sustainable development; ③ free enzyme It is difficult to remove, and the preparation process is complicated; ④ The reagents used are not recycled, which pollutes the environment

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] A method for preparing R-mandelic acid, the specific method steps are as follows:

[0027] (1) Activation of immobilized nitrilase

[0028] Using immobilized nitrilase as raw material, according to the mass (g) of immobilized nitrilase: the volume (mL) ratio of buffer solution is the ratio of 1:8, first nitrilase is added in the buffer solution, after stirring , put into an ultrasonic processor, and perform ultrasonic treatment for 10 minutes to activate the immobilized nitrilase. After the ultrasonic is completed, it is pumped into a suction filter for suction filtration, and the suction filtrate and suction filtration residue are collected respectively. For the collected suction filtrate, after adjusting the pH value, it can be used again for the activation of immobilized nitrilase; for the collected suction filtration residue, it is the activated immobilized nitrilase, which is used for the next step. Wherein, the immobilized nitrilase is the immobilized nitrilase p...

Embodiment 2

[0040] A method for preparing R-mandelic acid, with embodiment 1, wherein:

[0041] In step (1), the mass of the immobilized nitrilase: the volume ratio of the buffer solution is 1 g: 9 mL, and ultrasonic treatment is performed for 13 minutes, wherein the buffer solution is a phosphate buffer solution with a pH of 5.5.

[0042] In step (2), the temperature of the immobilized nitrilase was raised to 45°C.

[0043] In the (3) step, the volume of racemic mandelonitrile: the volume ratio of pure water is 1mL: 150mL, under the condition that the pumping speed is 1.5 times / hour of the volume of the immobilized nitrilase column reactor, continuous React for 6 hours.

[0044] In the (4) step, the pure water pumping speed is controlled to be 5 times / hour of the volume of the immobilized nitrilase column reactor.

[0045] In the 5th step, the raw material of macroporous strongly basic anion resin is D290 resin.

[0046] In the (6) step, the volume of the hydrochloric acid solution th...

Embodiment 3

[0048] A method for preparing R-mandelic acid, with embodiment 1, wherein:

[0049] In step (1), the mass of the immobilized nitrilase: the volume ratio of the buffer solution is 1 g: 10 mL, and ultrasonic treatment is performed for 15 minutes, wherein the buffer solution is a phosphate buffer solution with a pH of 6.0.

[0050] In step (2), the temperature of the immobilized nitrilase was raised to 50°C.

[0051] In the (3) step, the volume of racemic mandelonitrile: the volume ratio of pure water is 1mL: 200mL, under the condition that the pumping speed is 2.0 times / hour of the volume of the immobilized nitrilase column reactor, continuous React for 8 hours.

[0052] In step (4), the pumping speed of pure water is controlled to be 6 times / hour of the volume of the immobilized nitrilase column reactor.

[0053] In the 5th step, the raw material of macroporous strongly basic anion resin is D293 resin.

[0054] In the (6) step, the volume of the hydrochloric acid solution th...

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Abstract

The invention discloses a method for preparing R-mandelic acid, and belongs to the technical field of preparation of mandelic acid. Commercial racemic mandelonitrile, immobilized nitrilase and commercial macroporous strongly-basic anion resin are used as raw materials and catalyzed to generate the R-mandelic acid; and the R-mandelic acid is obtained by elution, concentration, drying and crystallization. The optical purity of the R-mandelic acid product prepared by the method reaches 98 percent, the R-mandelic acid can be widely applied to synthesis of multiple medicinal intermediates, the yield of the R-mandelic acid reaches over 70 percent, and the utilization rate of the raw materials is high; and the production equipment is conventional, the reaction conditions are mild, material resources are fully utilized, 'three wastes' are not discharged, the production cost is low, and the method is favorable for environmental protection and is an environment-friendly method. The product prepared by the method can be widely applied in the industries of medicine, hygiene, dyes, health care and the like.

Description

1. Technical field [0001] The invention belongs to the technical field of R-mandelic acid preparation, in particular to a method for preparing R-mandelic acid by selectively hydrolyzing racemic mandelonitrile with immobilized nitrilase. 2. Background technology [0002] Mandelic acid molecule has a chiral carbon atom and has two enantiomers (R) and (S). R-mandelic acid is a chemical intermediate with a wide range of uses. It is widely used in organic synthesis and pharmaceutical production. It is a commonly used raw material or intermediate in the field of pharmaceutical synthesis and dyes, such as semi-synthetic penicillins and cephalosporins. Synthesis of antibiotics, vasodilators, fungicides, antispasmodics, weight loss drugs, antineoplastic drugs, etc.; also used as fungicides or preservatives. In recent years, the demand for R-mandelic acid has been increasing year by year, and the market potential is huge. It is of great significance to accelerate the preparation and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P7/42C07C59/50C07C51/42
Inventor 周小华张杰苏昱王丹徐焕焕
Owner CHONGQING UNIV
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