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Efficient green synthesis method of hydroxycitronellal

A hydroxycitronellal, green synthesis technology, applied in the field of flavor and fragrance synthesis, can solve the problems of affecting the living environment, difficult to prepare, pollute the environment, etc., and achieve high yield and production efficiency, high yield and high selectivity. Effect

Active Publication Date: 2021-06-25
GUANGXI FORESTRY RES INST +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the raw material dihydromyrcene used is not easy to prepare, and the price is higher than that of citronellal
[0005] Visible, the existing method for synthesizing hydroxycitronellal all can produce poisonous gas and acid-containing waste water, pollute environment, influence people's living environment, therefore, it is particularly important to develop a kind of synthetic method of green environmental protection, cheap hydroxycitronellal

Method used

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  • Efficient green synthesis method of hydroxycitronellal

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preparation example Construction

[0025] POL-PPh used in the present invention 3 The preparation method is as follows: 1.0g 3V-PPh 3 Dissolve in 10ml of THF, then add 25mg of azobisisobutyronitrile, mix well and transfer to a reaction kettle, react at 100°C for 24h, evaporate the solvent in vacuo, and obtain white powder POL-PPh 3 .

[0026] The 3V-PPh 3 The preparation process is as follows: 22mmol of PPh 3 Dissolve it in 30ml THF, and slowly drop it into the pre-prepared 4-vinylmagnesium bromide Grignard reagent at 0°C. After the addition is completed, continue the reaction at room temperature for 2 hours. 4 The reaction was quenched with Cl solution, extracted with excess ethyl acetate, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, and finally the product was purified with a silica gel column to obtain a white 3V-PPh3 solid.

Embodiment 1

[0028] A kind of efficient green synthetic method of hydroxycitronellal, comprises the steps:

[0029] (1) Catalyst preparation: 500mg POL-PPh 3 and 25mgPdCl 2 Add 25 mL into a sealed tube filled with nitrogen, then add 5 mL of anhydrous THF, react overnight at 32 ° C, filter, remove the filtrate, wash the filter residue twice with ethyl acetate and ethanol, and collect the solid to obtain 519 mg of POL-PPh 3 @PdCl 2 solid catalyst;

[0030] (2) Catalyzed synthesis reaction: weigh 200mgPOL-PPh in a 500mL round bottom flask 3 @PdCl 2 , add citronellal 4.629g (30mmol), water 2.7g (100mmol) and toluene 150mL, stir evenly, react at 200°C for 12h to obtain a reaction solution;

[0031] (3) After the reaction liquid is cooled, filter and separate the solid catalyst, then fractionate the reaction liquid through a fractionating tower, and collect the distillate at about 257° C. to obtain 3.725 g of hydroxycitronellal.

[0032] The productive rate of this example hydroxycitronell...

Embodiment 2

[0036]A kind of efficient green synthetic method of hydroxycitronellal, comprises the steps:

[0037] (1) Catalyst preparation: 500mg POL-PPh 3 and 35mgPdCl 2 Add it into a 25mL sealed tube filled with nitrogen, then add 5mL of anhydrous THF, react overnight at 35°C, filter, remove the filtrate, wash the filter residue twice with ethyl acetate and ethanol, and collect the solid to obtain 524mg of POL-PPh 3 @PdCl 2 solid catalyst;

[0038] (2) Catalytic synthesis reaction: Weigh 200mgPOL-PPh3@PdCl in a 500mL round bottom flask 2 , add 6.172g (40mmol) of citronellal, 4.05g (150mmol) of water and 160mL of toluene, stir well, and react at 180°C for 18h to obtain a reaction solution;

[0039] (3) After the reaction liquid is cooled, filter and separate the solid catalyst, then fractionate the reaction liquid through a fractionating tower, and collect the distillate at about 257° C. to obtain 4.826 g of hydroxycitronellal.

[0040] The productive rate of this example hydroxycit...

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Abstract

The invention discloses an efficient green synthesis method of hydroxycitronellal. The method comprises the following steps: adding POL-PPh3, PdCl2 and anhydrous THF into a sealed container according to a mass ratio of (100: 5)-(10: 1), reacting at 25-35 DEG C overnight, filtering, removing filtrate, washing filter residues twice with ethyl acetate and ethanol respectively, and collecting solids to obtain a POL-PPh3-coated PdCl2 solid catalyst; taking 1 part by mass of a POL-PPh3-coated PdCl2 catalyst, 10-35 parts by mass of citronellal, 7-20 parts by mass of water and 500-800 parts by mass of toluene, uniformly stirring, and reacting at 180-200 DEG C for 10-24 hours to obtain a reaction solution; after the reaction liquid is cooled, filtering and separating the solid catalyst, fractionating the reaction liquid, and collecting a distillate at 257 DEG C, thereby obtaining the hydroxycitronellal. According to the method, citronellal and water are directly synthesized into hydroxycitronellal in one step under the catalysis of POL-PPh3-coated PdCl2, the method has the advantages of being environmentally friendly, low in price, high in catalytic efficiency, high in yield, mild in reaction condition, high in production efficiency, simple in process, non-toxic, harmless, free of emission of three wastes and the like, and a good foundation is laid for large-scale production of hydroxycitronellal.

Description

technical field [0001] The invention relates to the technical field of essence and fragrance synthesis, in particular to a high-efficiency green synthesis method of hydroxycitronellal. Background technique [0002] Hydroxycitronellal is a colorless, viscous liquid with the aroma of lilies and lilies of the valley. It is widely used in industries such as food, pharmaceuticals, daily chemicals, and spices. It is one of the most valuable spices in the world today. The annual demand has reached thousands of tons. Most of the domestic processes for preparing hydroxycitronellal use citronellal as a raw material, and citronellal can be extracted from lemon eucalyptus oil, citronella and other plants. The national standard GB / T 22179-2008 lemon eucalyptus (essential) oil specifies the main The component citronellal content is more than 75%, and the citronellal content in the active ingredient of the citronella also exceeds 80%. [0003] The domestic production process of hydroxyci...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/64C07C47/19B01J31/24
CPCC07C45/64B01J31/2404B01J2231/32B01J2531/824C07C47/19Y02P20/584
Inventor 杨漓潘英明唐海涛李桂珍蒙秀金谷瑶
Owner GUANGXI FORESTRY RES INST
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