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Chemical synthesis method of (R)-2-phenoxypropionic acid

A phenoxy propionic acid, chemical synthesis technology, applied in chemical instruments and methods, organic chemistry, carboxylate preparation, etc., can solve the problems of large environmental pollution, many by-products, high energy consumption, etc., and achieve high product purity, The effect of easy to obtain raw materials and simple process

Inactive Publication Date: 2019-01-01
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

Since p-diphenol is easily oxidized and the activity of the two hydroxyl groups is the same, it is easy to undergo double etherification, the reaction process is difficult to control, and there are disadvantages such as high energy consumption, many by-products and large environmental pollution.

Method used

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  • Chemical synthesis method of (R)-2-phenoxypropionic acid
  • Chemical synthesis method of (R)-2-phenoxypropionic acid
  • Chemical synthesis method of (R)-2-phenoxypropionic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] 1. Reagents and instruments

[0038] Instruments: Waters 2695 high-performance liquid chromatography; Autopol IV-T polarimeter; Bruker AVANCEIII 500MHz nuclear magnetic resonance spectrometer; Nicolet 6700 Fourier transform infrared spectrometer.

[0039] Reagents: L-alanine (AR), TCI (Shanghai) Chemical Industry Development Co., Ltd.; phenol (AR), Sinopharm Chemical Reagent Co., Ltd.; sodium carbonate (AR), Taicang Meida Reagent Co., Ltd.; chloride Potassium (AR), Sinopharm Chemical Reagent Co., Ltd.; potassium iodide (AR), Sinopharm Chemical Reagent Co., Ltd.; hydrochloric acid (36-38%, AR), Xilong Science Co., Ltd.; sodium nitrite (AR), Guangdong Guanghua Technology Co., Ltd.; Sodium Hydroxide (AR), Xilong Science Co., Ltd.

[0040] 2. Drawing of (S)-2-chloropropionic acid gas chromatography detection standard curve

[0041] Gas chromatography column: capillary column (30m×0.25mm); detector: FID; N 2 Flow rate: 30mL / min; H 2 Flow rate: 40mL / min; O 2 Flow rate: 4...

Embodiment 2

[0061] Embodiment 2 (S)-2-chloropropionic acid synthesis condition optimization

[0062] 1. Optimization of the molar ratio of L-alanine to hydrochloric acid

[0063] The experimental operation is the same as in Example 1, and the molar ratio of the step (1) L-alanine to hydrochloric acid in Example 1 is changed to 1:2, 1:2.5 and 1:3. After the sodium nitrite is added dropwise, react 2.5 h, sampling at intervals of 0.5h, the conversion rate of L-alanine is detected by gas phase, and the influence of the molar ratio of L-alanine and hydrochloric acid on the synthesis of (S)-2-chloropropionic acid is investigated, the results are as follows image 3 , so as to select the optimal hydrochloric acid dosage.

[0064] Depend on image 3 As can be seen, increasing the amount of hydrochloric acid is beneficial to the synthesis of (S)-2-chloropropionic acid, and when L-alanine: hydrochloric acid is 1:2.5 (mol / mol), the (S)-2-chloropropionic acid The molar conversion rate is the highe...

Embodiment 3

[0071] Embodiment 3 (R)-PPA synthesis condition optimization

[0072] 1. Optimization of etherification reaction temperature

[0073] The experimental operation is the same as that in Example 1, and the etherification reaction temperature in Step (2) of Example 1 is changed to 25, 45, 65, 85 and 125° C., respectively reacting for 3 hours, sampling at intervals of 0.5 hours, and detecting the conversion rate of the substrate by HPLC. Investigate the influence of etherification reaction temperature on (R)-2-phenoxypropionic acid synthesis, the results are as follows Figure 6 , so as to select the optimal reaction temperature.

[0074] Depend on Figure 6 It can be seen that the temperature rise is beneficial to the synthesis of (R)-2-phenoxypropionic acid, and when it reaches reflux at 125 ° C, the molar conversion rate of (R)-2-phenoxypropionic acid at different reaction times is higher than that of other temperature. This may be because on the one hand, reflux can increas...

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Abstract

The invention discloses a chemical synthesis method of (R)-2-phenoxypropionic acid. The chemical synthesis method comprises the following steps: performing diazotization and chlorination on L-alanineserving as a starting material to obtain (S)-2-chloropropionic acid; then carrying out an etherification reaction to obtain (R)-2-phenoxypropionic acid ((R)-PPA). According to the method, diazotization and chlorination are performed on L-alanine serving as the starting material to obtain (S)-2-chloropropionic acid, and then the etherification reaction is carried out to obtain the (R)-PPA, whereinthe molar conversion rate of (R)-2-phenoxypropionic acid is up to 92.45 percent. The chemical synthesis method of the (R)-PPA is proposed for the first time, and has the advantages of cheapness and easy availability of raw materials, simple process and higher product purity and the like.

Description

technical field [0001] The present invention relates to a kind of using L-alanine as the starting material, obtains (S)-2-chloropropionic acid through diazotization and chlorination, and then undergoes etherification reaction to obtain (R)-2-phenoxy The method for propionic acid ((R)-PPA) belongs to the technical field of chemical synthesis. Background technique [0002] (R)-PPA is an important substrate for the biosynthesis of (R)-2-(4-hydroxyphenoxy)propionic acid ((R)-HPPA), the key intermediate of aryloxyphenoxypropionic acid herbicides. Aryloxyphenoxypropionic acid herbicides are a new class of optically active herbicides, which were gradually developed in the 1960s on the basis of the compound dipropion, which was researched and developed by Hoechst Company, mainly by inhibiting the The activity of Acetyl-CoA Carboxylase (ACCase, EC6.4.1.2) in plants can inhibit the synthesis of fatty acids and make oleic acid, linoleic acid, linolenic acid, waxy layer and cuticle Th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/367C07C59/68
CPCC07C51/367C07C51/41C07C59/68C07C53/19
Inventor 薛亚平周海岩李一作姜瑞郑裕国王远山
Owner ZHEJIANG UNIV OF TECH
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