CN113563228A - Method for preparing 3-methoxypropionitrile - Google Patents
Method for preparing 3-methoxypropionitrile Download PDFInfo
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- CN113563228A CN113563228A CN202110842994.1A CN202110842994A CN113563228A CN 113563228 A CN113563228 A CN 113563228A CN 202110842994 A CN202110842994 A CN 202110842994A CN 113563228 A CN113563228 A CN 113563228A
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- methanol
- methoxypropionitrile
- acrylonitrile
- alkali metal
- temperature
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing 3-methoxypropionitrile, which is characterized by comprising the following steps: (1) adding a methanol alkali metal compound into methanol, heating to 30-80 ℃, and preserving heat for a period of time at the temperature; (2) dropping acrylonitrile, controlling the temperature to be 30-80 ℃, reacting for 2-8 h after dropping the acrylonitrile, adding a modification auxiliary agent, modifying the reaction liquid, and obtaining methoxypropionitrile after 30min, wherein the residual acrylonitrile is less than 0.5%; (3) and adding a modification auxiliary agent after the reaction is finished to generate a precipitate, and distilling to obtain the methoxypropionitrile. Compared with the prior art, the invention does not need the operation of removing alkali metal hydroxide; the activation time is shortened, the consumption of methanol is reduced, and the temperature can meet the requirement in industrial cooling water; the process is simple and easy to operate; the conversion rate is high; in addition, in the process of adding the auxiliary agent, the catalyst in the reaction liquid can be removed, and the generated precipitate is easy to separate, thereby providing convenience for subsequent reaction.
Description
Technical Field
The invention relates to the technical field of preparation of 3-methoxypropionitrile, and particularly relates to a method for preparing 3-methoxypropionitrile.
Background
The reaction of acrylonitrile with compounds containing active hydrogen atoms to form cyanoethyl derivatives is known as cyanoethylation. The reaction takes place at 40 ℃ in the presence of a base, wherein methanol reacts with acrylonitrile to form 3-methoxypropionitrile, which can be used for organic synthesis and also as a good solvent for plastic polymers. The 3-methoxypropionitrile is hydrogenated to produce methoxypropylamine, which can be used as a catalyst in the production of polyurethane foams and epoxy resins, and can also be used as detergents, emulsifiers, wetting agents, corrosion inhibitors, and the like.
In the prior art:
in Japanese patent No. 103505/1975, methoxypropionitrile is obtained using an alkali metal oxide as a catalyst.
② in the literature, in the synthesis research of 3-methoxypropylamine, commonly used sodium hydroxide is used as a catalyst, the molar ratio of methanol to acrylonitrile is 1.1: and reacting at the temperature of 1, 40-45 ℃ to obtain the methoxypropionitrile.
The above technique has the following disadvantages:
the alkali metal hydroxide needs to be removed in the subsequent process, and the operation is complex;
the active site of the reaction is methoxyl, sodium hydroxide is used as a catalyst, a certain time is needed for providing methoxyl ions, and the activation time is relatively long.
Disclosure of Invention
In view of the above, the invention provides a method for preparing 3-methoxypropionitrile, which has the characteristics of simple company, easy operation, high conversion rate and the like.
In order to achieve the purpose, the invention provides the following technical scheme:
a process for preparing 3-methoxypropionitrile, comprising the steps of:
(1) adding a methanol alkali metal compound into methanol, heating to 30-80 ℃, and preserving heat for a period of time at the temperature;
(2) dropwise adding acrylonitrile, controlling the temperature to be 30-80 ℃, reacting for 2-8 h after the acrylonitrile is dropwise added, adding a modification auxiliary agent, and obtaining methoxypropionitrile after 30min, wherein the residual acrylonitrile is less than 0.5%;
(3) and adding a modification auxiliary agent after the reaction is finished, generating a precipitate, and distilling to obtain the methoxypropionitrile.
In the above method for preparing 3-methoxypropionitrile, the content of the methanol alkali metal compound is 1 to 10 parts per thousand of the mass of methanol. The content of the alkali metal compound of methanol is preferably 2 to 5% by mass of methanol. The content of the alkali metal compound of methanol is preferably 2 to 3% by mass of methanol.
In the method for preparing 3-methoxypropionitrile, the acrylonitrile is weighed according to 5-30% excess molar mass of methanol. More preferably, the acrylonitrile is weighed according to the molar excess of 5-20% of the methanol. The preferable acrylonitrile is weighed according to the molar excess of methanol of 10-15%.
In the method for preparing 3-methoxypropionitrile, the first addition amount of the modification auxiliary agent is 20-80% of the amount of the methanol alkali metal compound, and the second addition amount is 20-80% of the amount of the methanol alkali metal compound. The first addition amount of the preferable modification auxiliary agent is 30-60% of the amount of the methanol alkali metal compound, and the second addition amount is 40-70% of the amount of the methanol alkali metal compound. The first adding amount of the preferable modification auxiliary agent is 40-50% of the amount of the methanol alkali metal compound, and the second adding amount is 50-60% of the amount of the methanol alkali metal compound.
According to the technical scheme, compared with the prior art, the invention has the following characteristics:
no operation for removing the alkali metal hydroxide is required; the activation time is shortened, the consumption of methanol is reduced, and the temperature can meet the requirement in industrial cooling water; the process is simple and easy to operate; the conversion rate is high; in addition, in the process of adding acid, the catalyst in the product can be removed, and the generated precipitate is easy to separate, thereby providing convenience for subsequent reaction.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The embodiment of the invention discloses a method for preparing 3-methoxypropionitrile, which has the characteristics of simple company, easy operation, high conversion rate and the like.
Example 1:
weighing 106.6g of methanol in a four-neck flask, adding sodium methoxide with the weight of about 2 per thousand, heating in a water bath to 60 ℃, keeping the temperature for 30min, weighing 159.0g of acrylonitrile in a dropping funnel, dropwise adding the acrylonitrile, controlling the temperature to be 60-65 ℃, completing dropwise addition in 2h, adding 0.1066g of sodium dihydrogen phosphate after reacting for 2h, measuring that about 0.3% of acrylonitrile remains, the conversion rate is 99.68%, and adding 0.0954g of sodium dihydrogen phosphate.
Example 2: weighing 105.6g of methanol in a four-neck flask, adding sodium methoxide with the weight of about 3 per thousand, heating in a water bath to 60 ℃, keeping the temperature for 30min, weighing 159.0g of acrylonitrile in a dropping funnel, dropwise adding the acrylonitrile, controlling the temperature to be 60-65 ℃, completing dropwise addition after 2h, adding 0.8650g of a mixture of phosphoric acid and sodium phosphate after reacting for 3h, measuring that about 0.5% of acrylonitrile remains, the conversion rate is 99.48%, and adding 0.1200g of the mixture of phosphoric acid and sodium phosphate.
Example 3: weighing 101.8g of methanol in a four-neck flask, adding sodium methoxide with the weight of about 2 per thousand, heating in a water bath to 50 ℃, keeping the temperature for 30min, weighing 159.0g of acrylonitrile in a dropping funnel, dropwise adding the acrylonitrile, controlling the temperature to be 50-60 ℃, completing dropwise addition in 2h, adding 0.0687g of sodium hydrogen sulfate after reacting for 2h, measuring that about 0.75% of acrylonitrile remains, the conversion rate is 99.22%, and adding 0.1458g of sodium hydrogen sulfate.
The embodiments in the present description are described in a progressive manner, each embodiment focuses on differences from other embodiments, and the same and similar parts among the embodiments are referred to each other. The device disclosed by the embodiment corresponds to the method disclosed by the embodiment, so that the description is simple, and the relevant points can be referred to the method part for description.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (5)
1. A process for preparing 3-methoxypropionitrile, comprising the steps of:
(1) adding a methanol alkali metal compound into methanol, heating to 30-80 ℃, and preserving heat for a period of time at the temperature;
(2) dropwise adding acrylonitrile, controlling the temperature to be 30-80 ℃, reacting for 2-8 h after the acrylonitrile is dripped, adding a modification auxiliary agent, and obtaining methoxypropionitrile after 30min, wherein the residual amount of the acrylonitrile is less than 0.5%;
(3) and adding an auxiliary agent after the reaction is finished, generating a precipitate, and distilling to obtain the methoxypropionitrile.
2. The method according to claim 1, wherein the content of the methanol alkali metal compound is 2 to 15% by mass of methanol.
3. The method of claim 1, wherein the acrylonitrile is weighed in a molar excess of 1-25% of methanol.
4. The method for preparing 3-methoxypropionitrile of claim 1, wherein the modifying additive is selected from the group consisting of sodium dihydrogen phosphate, sodium hydrogen sulfate, ferric sulfate, a mixture of phosphoric acid and phosphate, phosphoric acid, and a mixture of acetic acid and acetate.
5. The method of claim 1, wherein the alkali metal methoxide is lithium methoxide, sodium methoxide, potassium methoxide, rubidium methoxide, or a mixture thereof.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202110842994.1A CN113563228A (en) | 2021-07-26 | 2021-07-26 | Method for preparing 3-methoxypropionitrile |
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| CN202110842994.1A CN113563228A (en) | 2021-07-26 | 2021-07-26 | Method for preparing 3-methoxypropionitrile |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114276254A (en) * | 2021-12-31 | 2022-04-05 | 万华化学集团股份有限公司 | Synthetic method of 3-methoxypropylamine |
Citations (5)
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| CN106883136A (en) * | 2017-03-17 | 2017-06-23 | 浙江联盛化学股份有限公司 | The synthetic method of 3 methoxyl group N, N dimethylpropionamides |
| CN106966923A (en) * | 2017-03-17 | 2017-07-21 | 浙江联盛化学股份有限公司 | A kind of synthetic method of 3 methoxyl group N, N dimethylpropionamides |
| CN109456204A (en) * | 2018-10-30 | 2019-03-12 | 昆山市祥和精细化工厂 | γ-methoxy propanamine preparation method |
| CN109761910A (en) * | 2018-12-04 | 2019-05-17 | 华中农业大学 | A kind of synthetic method for the general woods that ends |
| CN113004171A (en) * | 2021-03-09 | 2021-06-22 | 万华化学集团股份有限公司 | Preparation method of 3-methoxypropylamine |
-
2021
- 2021-07-26 CN CN202110842994.1A patent/CN113563228A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106883136A (en) * | 2017-03-17 | 2017-06-23 | 浙江联盛化学股份有限公司 | The synthetic method of 3 methoxyl group N, N dimethylpropionamides |
| CN106966923A (en) * | 2017-03-17 | 2017-07-21 | 浙江联盛化学股份有限公司 | A kind of synthetic method of 3 methoxyl group N, N dimethylpropionamides |
| CN109456204A (en) * | 2018-10-30 | 2019-03-12 | 昆山市祥和精细化工厂 | γ-methoxy propanamine preparation method |
| CN109761910A (en) * | 2018-12-04 | 2019-05-17 | 华中农业大学 | A kind of synthetic method for the general woods that ends |
| CN113004171A (en) * | 2021-03-09 | 2021-06-22 | 万华化学集团股份有限公司 | Preparation method of 3-methoxypropylamine |
Non-Patent Citations (1)
| Title |
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| 王红卫等: "1-氯-3-甲氧基丙烷的合成", 精细与专用化学品, vol. 13, no. 15, pages 21 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114276254A (en) * | 2021-12-31 | 2022-04-05 | 万华化学集团股份有限公司 | Synthetic method of 3-methoxypropylamine |
| CN114276254B (en) * | 2021-12-31 | 2023-09-19 | 万华化学集团股份有限公司 | Synthesis method of 3-methoxypropylamine |
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