CN107805187B - Production process of monochamus alternatus gathering pheromone undecyloxy ethanol - Google Patents
Production process of monochamus alternatus gathering pheromone undecyloxy ethanol Download PDFInfo
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- CN107805187B CN107805187B CN201710923686.5A CN201710923686A CN107805187B CN 107805187 B CN107805187 B CN 107805187B CN 201710923686 A CN201710923686 A CN 201710923686A CN 107805187 B CN107805187 B CN 107805187B
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- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
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Abstract
The invention discloses a production process of monochamus alternatus gathering pheromone undecyloxy ethanol, which comprises the following production steps: (1) taking 2-tert-butoxychloroethane as a raw material, and carrying out nucleophilic substitution reaction with undecanol in a first solvent with a proper amount of a first catalyst under an alkaline condition, wherein the reaction temperature is controlled to be 0-120 ℃, so as to prepare 1- (2-tert-butoxyethoxy) -undecane; (2) and (2) carrying out a tert-butyl removing reaction on the 1- (2-tert-butoxyethoxy) -undecane prepared in the step (1) in a second solvent with a proper amount of second catalyst under an acidic condition to obtain a target product, namely, undecyloxyethanol, wherein the reaction temperature is controlled to be 0-100 ℃. By the method, the purity of the target product obtained by the method can be more than 99%, the reaction condition is mild, the yield is high, the operation is simple and convenient, the production cost is low, and the method is suitable for large-scale production.
Description
Technical Field
The invention relates to the field of forest pest control, in particular to a production process of monochamus alternatus gathering pheromone undecyloxy ethanol.
Background
Pine wood nematode disease is a worldwide major forest disease, the prevention and control of the pine wood nematode disease are always a worldwide problem, and a prevention and control technology capable of curing pine diseases after infection is not found at present. The disease occurs in many provinces of China successively, and tens of millions of pine trees are killed. Annual loss caused by the pine wood nematodes is nearly two billion yuan, the loss of ecological service value is more than sixty billion yuan, and the diseases are spread and spread in China at the speed of 7.5 ten thousand mu per year. Pine wood nematode is a quarantine pest with serious harmfulness and serious danger, and the pine wood nematode disease is a destructive disease of pine trees. Once infected, the pine cannot be cured, the death speed is high, the pine can die in the fastest 40 days, the whole pine forest can be destroyed within 3-5 years, the pine tree is called as cancer of the pine tree, the spread is rapid, and the prevention and treatment difficulty is high.
Monochamus alternatus is the main transmission medium for pine wood nematode wilt. In the severely diseased pine forest, 18000 bursaphelenchus xylophilus can be transmitted by the adult cattle on average every day; to eradicate pine wilt disease, monochamus alternatus must be killed. The population density of monochamus alternatus in the monochamus alternatus epidemic area directly influences the propagation speed of the monochamus alternatus disease, and the monochamus alternatus can be prevented and controlled in time to spread the monochamus alternatus disease.
The pine wood nematode disease can be eradicated by reducing the density of the monochamus alternatus and reducing the harm and eliminating the monochamus alternatus. Therefore, comprehensive control measures such as manpower, trapping, biology, chemistry and the like need to be carried out, and the monochamus alternatus control work is carried out comprehensively. The monochamus alternatus hope gathering pheromone is a most efficient prevention and control method developed in recent years, and the monochamus alternatus hope gathering pheromone which is artificially synthesized can be used for trapping and killing monochamus alternatus hope in a trap, so that the population density of monochamus alternatus hope can be effectively reduced, and the method is one of the most effective measures for comprehensively preventing and controlling monochamus alternatus hope.
For monochamus alternatus gathering pheromone undecyloxy ethanol, the currently reported synthesis methods mainly comprise the following two methods:
firstly, a large amount of glycol is used as a reactant and a solvent, metal sodium is added to prepare sodium alkoxide, and then 1-bromoundecane is added to react to prepare undecyloxy ethanol [ Sci.Rep.2016,6,29300; dyes and Pigments 2013,96,16-24 ]; a large amount of glycol is needed in the reaction, so that raw materials are wasted, the product is difficult to extract, and more diethers with high boiling points are generated in the reaction process to replace byproducts, so that the yield is only about 54 percent. The chemical formula of the synthesis method is as follows:
secondly, reacting ethylene glycol with sodium hydrogen in large equivalent in N, N-dimethylformamide to prepare sodium alkoxide, and then adding 1-bromoundecane to react to prepare undecyloxyethanol [ J.chem.Ecol.2010,36, 570-; the reaction also requires a high equivalent of ethylene glycol and N, N-dimethylformamide as a solvent, making the product more difficult to extract from the reaction system, resulting in a yield of only 47%. The chemical formula of the synthesis method is as follows:
in the 2 synthesis methods, 1-bromoundecane is used as a raw material for synthesis, the raw material is expensive (5000/500 g), and no large amount of products can be supplied, so that the large production of the monochamus alternatus gathering pheromone undecyloxy ethanol is difficult.
In view of the good market prospect of monochamus alternatus gathering pheromone undecyloxy ethanol, it is very meaningful to find a novel synthetic method for realizing the industrial production of monochamus alternatus gathering pheromone undecyloxy ethanol, wherein the key points are to solve the key problems of raw material supply, production cost, production operation and the like.
Disclosure of Invention
The invention aims to research and solve the defects of the existing monochamus alternatus gathering pheromone undecyloxy ethanol production technology, and provides the method which is simple and convenient to operate, has low cost and can realize the amplification production of monochamus alternatus gathering pheromone undecyloxy ethanol.
In order to solve the technical problems, the invention adopts a technical scheme that:
provides a production process of monochamus alternatus gathering pheromone undecyloxy ethanol, which comprises the following production steps:
(1) taking 2-tert-butoxychloroethane as a raw material, and carrying out nucleophilic substitution reaction with undecanol in a first solvent with a proper amount of a first catalyst under an alkaline condition, wherein the reaction temperature is controlled to be 0-120 ℃, so as to prepare 1- (2-tert-butoxyethoxy) -undecane;
(2) and (2) carrying out a tert-butyl removing reaction on the 1- (2-tert-butoxyethoxy) -undecane prepared in the step (1) in a second solvent with a proper amount of second catalyst under an acidic condition to obtain a target product, namely, undecyloxyethanol, wherein the reaction temperature is controlled to be 0-100 ℃.
In a preferred embodiment of the invention, the 2-tert-butoxychloroethane is prepared from chloroethanol and isobutene.
In a preferred embodiment of the invention, the reaction temperature in step (1) is 60-100 ℃ and in step (2) is 60 ℃ or lower.
In a preferred embodiment of the invention, in the step (1), the mass fraction ratio of each material is undecanol: alkali: 2-tert-butoxychloroethane: first catalyst ═ 1: 1.1-1.5: 1.1-1.5: 0.01 to 0.05.
In a preferred embodiment of the present invention, in step (1), the base used is at least one of metallic sodium, sodium hydrogen, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, n-butyllithium, sodium amide and tert-butyllithium.
In a preferred embodiment of the present invention, in step (1), the first solvent used is one or more of tetrahydrofuran, ethylene glycol dimethyl ether, DMF, DMSO, dichloromethane, chloroform, benzene, and toluene.
In a preferred embodiment of the present invention, in step (1), the first catalyst is a mixture of one or more of sodium bromide, potassium bromide, sodium iodide, potassium iodide, tetrabutylammonium iodide, octadeca-coronene, pentadeca-coronene.
In a preferred embodiment of the present invention, in step (2), the second catalyst is a mixture of one or more of hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, trifluoroacetic acid, and methanesulfonic acid.
In a preferred embodiment of the present invention, in step (2), the second solvent is one or more of water, methanol, ethanol, isopropanol, butanol, tetrahydrofuran, ethylene glycol dimethyl ether, 1, 4-dioxane, toluene, DMF, DMSO, dichloromethane, and chloroform.
The invention has the beneficial effects that: the production process of the monochamus alternatus gathering pheromone undecyloxy ethanol adopts cheap and easily-obtained chloroethanol and 2-tert-butoxy chloroethane synthesized by isobutene as raw materials, 1- (2-tert-butoxy ethoxy) -undecane is prepared by reacting with cheap and easily-obtained undecyl alcohol, and then undecyloxy ethanol is prepared after a tert-butyl protecting group is removed; the purity of the target product obtained by using the process can be more than 99 percent, the reaction condition is mild, the yield is high, the operation is simple, convenient and convenient, the production cost is low, and the process is suitable for large-scale production.
Drawings
FIG. 1 is a diagram showing a synthesis of undecyloxyethanol in a preferred embodiment of the present invention.
Detailed Description
The following detailed description of the preferred embodiments of the present invention, taken in conjunction with the accompanying drawings, will make the advantages and features of the invention easier to understand by those skilled in the art, and thus will clearly and clearly define the scope of the invention.
A production process of monochamus alternatus gathering pheromone undecyloxy ethanol comprises the following production steps: :
(1) taking 2-tert-butoxychloroethane prepared from chloroethanol and isobutene as a raw material, and carrying out nucleophilic substitution reaction with undecanol in a first solvent with a proper amount of a first catalyst under an alkaline condition, wherein the reaction temperature is controlled at 60-100 ℃ to prepare 1- (2-tert-butoxyethoxy) -undecane; the mass fraction ratio of each material is undecanol: alkali: 2-tert-butoxychloroethane: first catalyst ═ 1: 1.1-1.5: 1.1-1.5: 0.01 to 0.05; the adopted alkali is at least one of metallic sodium, sodium hydrogen, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, n-butyl lithium, sodium amide and tert-butyl lithium, and sodium hydrogen and potassium tert-butoxide are preferentially adopted; the first solvent is one or more of tetrahydrofuran, ethylene glycol dimethyl ether, DMF, DMSO, dichloromethane, chloroform, benzene and toluene, preferably tetrahydrofuran or toluene; the first catalyst is one or more of sodium bromide, potassium bromide, sodium iodide, potassium iodide, tetrabutylammonium iodide, octodeca-coronene and pentadeca-coronene, preferably potassium iodide, tetrabutylammonium iodide and octodeca-coronene;
(2) performing a tert-butyl removal reaction on the 1- (2-tert-butoxyethoxy) -undecane prepared in the step (1) in a second solvent with a proper amount of second catalyst under an acidic condition to obtain a target product, namely, undecyloxyethanol, wherein the reaction temperature is less than or equal to 60 ℃; the second catalyst is one or more of hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, trifluoroacetic acid and methanesulfonic acid, and hydrochloric acid and trifluoroacetic acid are preferably adopted; the second solvent is one or more selected from water, methanol, ethanol, isopropanol, butanol, tetrahydrofuran, ethylene glycol dimethyl ether, 1, 4-dioxane, toluene, DMF, DMSO, dichloromethane, and chloroform, preferably methanol, tetrahydrofuran, water, acetic acid, and dichloromethane.
The reaction chemical formula of the invention is as follows:
example 1:
adding 172 g (1mol,1eq.) of undecanol and 800 ml of toluene into a reaction bottle, adding 25.3 g (1.1mol,1.1eq.) of metallic sodium in batches in a heating reflux state, and refluxing until the metallic sodium completely reacts; then, 8.3 g (0.05mol,0.05eq.) of potassium iodide was added, and 150.7 g (1.1mol,1.1eq.) of 2-t-butoxychloroethane was added dropwise, and after the dropwise addition, the reaction was continued under reflux by heating. After the gas phase detection reaction, cooling, adding 200 ml of water to perform extraction reaction, separating liquid, and concentrating an organic phase.
Adding 800 ml of dichloromethane into the residue, stirring to dissolve, adding 100 ml of trifluoroacetic acid, stirring at 25 ℃ until the reaction is complete, adjusting the pH to 8 by using a saturated sodium carbonate aqueous solution, separating liquid, drying an organic phase by using anhydrous sodium sulfate, performing suction filtration, concentrating a filtrate, and performing reduced pressure distillation to obtain 196 g of undecyloxy ethanol, wherein the yield is 91% and the purity is 99.2%.
Example 2:
172 g (1mol,1eq., 60%) of undecanol and 800 ml of tetrahydrofuran are added into a reaction flask, 48 g (1.2mol,1.2eq., 60%) of sodium hydrogen are added in portions, and heating and refluxing are carried out for 30 minutes; then, 7.4 g (0.02mol,0.02eq.) of tetrabutylammonium iodide was added, 150.7 g (1.1mol,1.1eq.) of 2-tert-butoxychloroethane was added dropwise, and after the dropwise addition, the reaction was continued under reflux with heating. After the gas phase detection reaction, cooling, adding 200 ml of water for extraction and quenching reaction, concentrating to remove the solvent, extracting with dichloromethane, combining organic phases, and concentrating.
Adding 300 ml of concentrated hydrochloric acid into the residue, and stirring at 35 ℃ for reaction; after the gas phase detection reaction, extracting by dichloromethane, combining organic phases, drying by sodium carbonate, filtering, concentrating the filtrate, and distilling under reduced pressure to obtain 184 g of undecyloxy ethanol, wherein the yield is 85 percent, and the purity is 99.1 percent.
Example 3:
688 g (4mol,1eq.) of undecanol, 52.8 g (0.2mol,0.05eq.) of octadecanohexa and 5L of tetrahydrofuran are added into a reaction bottle, 538 g (4.8mol,1.2eq.) of potassium tert-butoxide are added in portions, and the mixture is heated and refluxed for 30 minutes; 657.6 g (4.8mol,1.2eq.) of 2-tert-butoxychloroethane was added dropwise, and after the addition, the reaction was continued under reflux. After the gas phase detection reaction is finished, cooling, adding 500 ml of water for extraction and quenching reaction, concentrating to remove the solvent, extracting by dichloromethane, combining organic phases and concentrating.
Example 4:
172 g (1mol,1eq.) of undecanol and 300 ml of DMF are added into a reaction flask, 48 g (1.2mol,1.2eq., 60%) of sodium hydroxide are added in portions, and after the mixture is dissolved, 7.4 g (0.02mol,0.02eq.) of tetrabutylammonium iodide is added; the temperature is kept at 100 ℃, 150.7 g (1.1mol,1.1eq.) of 2-tert-butoxychloroethane is slowly dropped, and the temperature is kept at 100 ℃ for reaction after the dropping is finished. After the gas phase detection reaction, the solvent is removed by concentration, 800 ml of water is added, the mixture is fully stirred and extracted by dichloromethane, and organic phases are combined and concentrated.
Adding 300 ml of concentrated hydrochloric acid into the residue, and stirring at 35 ℃ for reaction; after the gas phase detection reaction is finished, dichloromethane is used for extraction, organic phases are combined, sodium carbonate is dried and is filtered, filtrate is concentrated, and 175 g of undecyloxy ethanol is obtained by reduced pressure distillation, the yield is 81%, and the purity is 99.2%.
Adding 2L of methanol and 100 ml of concentrated hydrochloric acid into the residue, heating and refluxing for reaction, detecting the reaction by gas phase, concentrating to remove the solvent, extracting by dichloromethane, drying by sodium carbonate, filtering, concentrating the filtrate, and distilling under reduced pressure to obtain 795 g of undecyloxy ethanol, wherein the yield is 92% and the purity is 99.5%.
Example 5:
172 g (1mol,1eq.) of undecanol and 500 ml of tetrahydrofuran are added to a reaction flask, ice water is cooled, and 750 ml (1.2mol,1.2eq.,) of n-butyllithium (1.6M) are added dropwise; after the dropwise addition, 7.5 g (0.05mol,0.05eq.) of sodium iodide was added; heating and refluxing, slowly adding 150.7 g (1.1mol,1.1eq.) of 2-tert-butoxychloroethane dropwise, and continuing heating and refluxing reaction after the dropwise addition is finished. After the gas phase detection reaction, cooling, adding 200 ml of water for extraction and quenching reaction, concentrating to remove the solvent, extracting with dichloromethane, combining organic phases, and concentrating.
Dissolving the residue in 500 ml of methanol, adding 50 ml of concentrated hydrochloric acid, and heating and refluxing for reaction; after the gas phase detection reaction is finished, removing the solvent, extracting by dichloromethane, combining organic phases, drying by sodium carbonate, filtering, concentrating the filtrate, and distilling under reduced pressure to obtain 190 g of undecyloxy ethanol, wherein the yield is 88 percent, and the purity is 99.5 percent.
The above description is only an embodiment of the present invention, and not intended to limit the scope of the present invention, and all modifications of equivalent structures and equivalent processes performed by the present specification and drawings, or directly or indirectly applied to other related technical fields, are included in the scope of the present invention.
Claims (5)
1. A production process of monochamus alternatus gathering pheromone undecyloxy ethanol is characterized by comprising the following production steps:
(1) taking 2-tert-butoxychloroethane as a raw material, and carrying out nucleophilic substitution reaction with undecanol in a first solvent with a first catalyst under an alkaline condition, wherein the reaction temperature is controlled to be 0-120 ℃, so as to prepare 1- (2-tert-butoxyethoxy) -undecane; the adopted first solvent is one or a mixture of more of tetrahydrofuran, ethylene glycol dimethyl ether, DMF, DMSO, dichloromethane, trichloromethane, benzene and toluene; the first catalyst is one or a mixture of more of sodium bromide, potassium bromide, sodium iodide, potassium iodide, tetrabutylammonium iodide, octodeca-crown hexa-crown and pentadeca-crown penta;
(2) performing a tert-butyl removal reaction on the 1- (2-tert-butoxyethoxy) -undecane prepared in the step (1) in a second solvent with a second catalyst under an acidic condition to obtain a target product, namely, undecyloxyethanol, wherein the reaction temperature is controlled to be 0-100 ℃; the second catalyst is one or a mixture of hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, trifluoroacetic acid and methanesulfonic acid; the second solvent is one or more of water, methanol, ethanol, isopropanol, butanol, tetrahydrofuran, ethylene glycol dimethyl ether, 1, 4-dioxane, toluene, DMF, DMSO, dichloromethane and chloroform.
2. The process for producing Monochamus alternatus aggregative pheromone undecyloxy ethanol according to claim 1, wherein the 2-tert-butoxychloroethane is prepared from chloroethanol and isobutene.
3. The process for producing Monochamus alternatus aggregation pheromone undecoxyethanol according to claim 1, wherein in step (1), the reaction temperature is 60-100 ℃, and in step (2), the reaction temperature is 60 ℃ or less.
4. The production process of monochamus alternatus hope aggregation pheromone undecyloxy ethanol as claimed in claim 1, wherein in the step (1), the mass fraction ratio of each material is undecanol: alkali: 2-tert-butoxychloroethane: first catalyst ═ 1: 1.1-1.5: 1.1-1.5: 0.01 to 0.05.
5. The process for producing Monochamus alternatus aggregation pheromone undecoxyethanol according to claim 1, wherein in step (1), the base used is at least one of metallic sodium, sodium hydrogen, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, n-butyllithium, sodium amide and tert-butyllithium.
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| CN108727167B (en) * | 2018-04-27 | 2023-01-06 | 苏州泽农生物科技有限公司 | Preparation method of anoplophora chinensis gathering pheromone |
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