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Method for preparing geranic acid by oxidizing citral

A technology of citral and geranic acid, applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylate, etc., can solve the problems of high oxidant toxicity, low reaction yield, many by-products, etc., and achieve high selectivity , high yield, and the effect of reducing acidity

Active Publication Date: 2021-01-12
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the above methods, NaClO2 is used as the oxidizing agent, the dosage is large, the toxicity is high, and the catalyst NaH2 The presence of PO4 and the reaction product geranic acid makes the pH of the reaction solution strongly acidic, resulting in many by-products in the reaction process and a low reaction yield
[0007] In summary, the existing artificial synthesis of geranic acid has the disadvantages of high oxidant toxicity, long process and low yield, so it is necessary to develop a green and efficient synthesis process

Method used

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  • Method for preparing geranic acid by oxidizing citral
  • Method for preparing geranic acid by oxidizing citral
  • Method for preparing geranic acid by oxidizing citral

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The oxidation reaction is carried out in a tank reactor, the effective volume of the reactor is 500ml, and the air feed tube adopts an insertion tube. When carrying out the oxidation test, first open the reactor power supply, add citral (200g / 1.314mol), manganese dioxide (0.09g), manganese acetate (0.45g) and cobalt acetate (0.27g) in the reactor, add 2- Hydroxypyridine (0.09g); set the speed of the reactor at 300r / min, open the inlet and outlet valves of the reaction tube carrier gas, and turn on the nitrogen carrier gas at a flow rate of 1L / min, and control the reaction pressure at 1.5MPa(G) after purging with nitrogen for 30min. The heating mantle of the reactor will be opened, and the temperature of the reactor will be raised to 220°C; after the temperature of the reactor is stable, start timing, open the air feed valve, adjust the air feed flow rate to 3.2L / min, and the cumulative feed of air is 280L (in terms of oxygen and The air feed was stopped after the molar ...

Embodiment 2

[0039]The oxidation reaction is carried out in a tank reactor, the effective volume of the reactor is 500ml, and the air feed tube adopts an insertion tube. When carrying out the oxidation experiment, first turn on the reactor power supply, add citral (200g / 1.314mol), manganese acetate (0.10g) and copper chloride (0.11g) in the reactor; add 4-methyl-2-hydroxypyridine (0.02g), the reactor is set at a speed of 300r / min, the inlet and outlet valves of the reaction tube carrier gas are opened, the nitrogen carrier gas is turned on, the flow rate is 1L / min, and the reaction pressure is controlled to 1.5MPa(G) after purging with nitrogen for 30min. The heating mantle of the reactor will be turned on, and the temperature of the reactor will be raised to 250°C; after the temperature of the reactor is stabilized, the timer will be started, the air feed valve will be opened, the air feed flow rate will be adjusted to 3.2L / min, and the cumulative feed of air will be 280L (in terms of oxyg...

Embodiment 3

[0042] The oxidation reaction is carried out in a tank reactor, the effective volume of the reactor is 500ml, and the air feed tube adopts an insertion tube. When carrying out oxidation experiment, at first open reactor power supply, add citral (200g / 1.314mol), manganese acetate (0.88g) and cobalt acetate (0.94g) in reactor; Add 2-hydroxypyridine (0.51g) reactor Set the rotation speed to 300r / min, open the inlet and outlet valves of the carrier gas in the reaction tube, and turn on the nitrogen carrier gas at a flow rate of 1L / min. After purging with nitrogen for 30min, control the reaction pressure to 1.5MPa(G). The heating mantle of the reactor will be opened, and the temperature of the reactor will be raised to 220°C; after the temperature of the reactor is stabilized, start timing, open the air feed valve, adjust the air feed flow rate to 6.4L / min, and the cumulative feed of air is 534L (in terms of oxygen and The air feed was stopped after the citral molar ratio was 4.0:1...

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Abstract

The invention provides a method for preparing geranic acid by oxidizing citral. The method comprises the following step: with a metal active component and a hydroxyl-containing azacyclo-ligand as catalysts and oxygen-containing gas as an oxidant, catalyzing citral to undergo an oxidation reaction so as to prepare the geranic acid. According to the method, the hydroxyl-containing azacyclo-ligand isadopted as a ligand, metal manganese, cobalt or copper and the like are adopted as active metals, oxidation depth is controlled, and the generation of oxidation byproducts is reduced, so the selectivity of the main product geranic acid is guaranteed, and unreacted citral is recycled. According to the method, a large amount of citral which is easy to obtain serves as a starting material, oxygen-containing gas such as air serves as a clean oxidizing agent, and the geranic acid is obtained through one-step catalytic oxidation, so a synthesis route is short, yield is high, and cost advantage is good.

Description

technical field [0001] The invention belongs to the field of fine chemical industry, and in particular relates to a method for preparing geranic acid by using citral as a raw material and oxidizing with oxygen-containing gas. Background technique [0002] Geranic acid, also known as geranic acid, is a plant extract with a fresh oily green aroma and an apple-like vegetable and fruit aroma. Very important daily fragrance. [0003] The addition of geranic acid is beneficial to relieve skin problems such as skin itching and small red bumps, while improving the fragrance of the shower gel. At present, the main source of geranic acid is artificial synthesis: [0004] Hu Yanhua et al. introduced the results of experiments under different solvent conditions using citral as a raw material and sodium chlorite as an oxidizing agent in "Study on the Synthesis of α-Cyclic Geranic Acid": (1) using 2-methyl- Using 2-butene and tert-butanol as solvents, sodium chlorite oxidizes citral to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C57/03C07C51/235B01J31/22
CPCC07C51/235B01J31/2217B01J2531/72B01J2531/842B01J2531/847B01J2531/845B01J2531/16B01J2531/0238B01J2231/70C07C57/03
Inventor 朱小瑞宿林卢玉勤刘英俊王文薛莹孙钦鹤张鹏举张晨张永振黎源
Owner WANHUA CHEM GRP CO LTD