CN106883136A - The synthetic method of 3 methoxyl group N, N dimethylpropionamides - Google Patents
The synthetic method of 3 methoxyl group N, N dimethylpropionamides Download PDFInfo
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- CN106883136A CN106883136A CN201710160460.4A CN201710160460A CN106883136A CN 106883136 A CN106883136 A CN 106883136A CN 201710160460 A CN201710160460 A CN 201710160460A CN 106883136 A CN106883136 A CN 106883136A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
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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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- C07—ORGANIC CHEMISTRY
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- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
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Abstract
The present invention relates to the synthetic method of 3 methoxyl group N, N dimethylpropionamides, belong to technical field of chemical synthesis.Described synthetic method includes being added to 3 methoxypropionic acids and dimethylamine in closed reactor, is warming up to 80 150 DEG C and reacts to obtain 3 methoxyl group N, N dimethylpropionamides, wherein, the pressure in closed reactor is 0.1 10.0MPa.It is raw material that the present invention uses 3 methoxypropionic acids, it is dehydrated in closed reactor high temperature with dimethylamine, polyalcohol, base catalyst are not needed, easy reaction, and product yield high, purity are high, realize in high yield while pollution less, low cost, meet the requirement of modern chemical industry green syt.Meanwhile, with inexpensive acrylonitrile as initiation material, acrylonitrile alkoxide obtains methoxypropionitrile to 3 methoxypropionic acid of the invention, then hydrolyzes prepared, and simple to operate, energy consumption is low.
Description
Technical field
The present invention relates to a kind of synthetic method of chemical materials intermediate, more particularly to a kind of 3- methoxyl groups-N, N- diformazan
The synthetic method of base propionamide, belongs to technical field of chemical synthesis.
Background technology
3- methoxyl groups-N, N- dimethylpropionamide (structural formula is as shown in formula I), are a kind of water white transparency solvents, there is acid amides
Group and alkyl group, can mix with multi-solvents, being capable of high level dissolving polymer polyamide；With highly dissoluble, height
The features such as permeability, high fluidity, low viscosity, low surface tension, and there is no excitant to skin, safety and environmental protection can be very
Conventional solvent 1-METHYLPYRROLIDONE is substituted well, is widely used in electronics, medicine, agricultural chemicals, pigment, cleaning agent, insulation material
In the industries such as material.Nowadays the security solvent market for constantly being refined in competition, in addition to dissolubility, high volatile and low toxicity also turn into
The important chip of solvent competition, therefore, the wide market of product.
For the synthesis of 3- methoxyl groups-N, N- dimethylpropionamide, existing method is mainly with 3- methoxypropionic acid first
Ester and dimethylamine are raw material, and diethylene glycol (DEG) synthesizes for solvent under the catalysis of sodium alkoxide.But in this method solvent diethylene glycol (DEG) because
245 DEG C of boiling point is too high, and recovery cost is larger, it is impossible to reuse.And catalyst sodium alkoxide large usage quantity, it is necessary to use sulfuric acid neutralize,
Treatment is refiltered, technological operation is cumbersome, produce a large amount of solid slags, do not meet the requirement of environmental protection.Furthermore, reaction yield
It is not high with selectivity, and dimethylamine raw material needs significantly excessive, the waste gas of a large amount of dimethylamine of production process generation, to two
Methylamine gas recovery system equipment requirement is very high, invests very big.
Reaction equation is as follows：
Such as Chinese patent (application number：201380019269.8) a kind of manufacturer of beta-alkoxypropionamide is disclosed
Method, using β-alkoxy acrylic ester class and amine reaction manufacture beta-alkoxypropionamide in the patent, but the method with
β-alkoxy acrylic ester class is raw material, with amine reaction, needs to reclaim accessory substance after reaction, and in the accessory substance for reclaiming
Containing substantial amounts of amine, treatment is more difficult, and raw material is in itself that, through acroleic acid esterification, methoxylation gained, process is relatively complicated, energy
Consumption is high.
The content of the invention
It is an object of the invention to the deficiency being directed to present in prior art, there is provided a kind of low cost, 3- in high yield
The synthetic method of methoxyl group-N, N- dimethylpropionamide.
Above-mentioned purpose of the present invention is achieved through the following technical solutions：The synthesis side of 3- methoxyl groups-N, N- dimethylpropionamide
Method, described synthetic method includes being added to 3- methoxypropionic acids and dimethylamine in closed reactor, is warming up to 80-150 DEG C
React to obtain 3- methoxyl groups-N, N- dimethylpropionamide.
There is reversible reaction in the present invention, need to be anti-in closed space in order to avoid the volatilization of raw material amine under hot conditions
Should.Present invention pollution while realizing in high yield is few, meets the requirement of modern chemical industry green syt.If reacting in the present invention
Temperature is too low, then in acid-base reaction into cannot realize dehydration after salt；If reaction temperature is too high, can increase back reaction, cause
Hypertonia, and then influence yield and purity.
The present invention is that reversible reaction occurs so that high-pressure sealed reaction avoids the volatilization of raw material amine under hot conditions, densification high
Close under reacting and produced, it is necessary to control the pressure in reactor without waste gas.Equipment used is high-pressure sealed equipment in the present invention,
Such as one or more in autoclave, pressurization tower reactor, pressure pipeline reactor, preferably autoclave.Excessive pair of pressure sets
Standby requirement is higher, and so as to cause investment to become big, pressure is too small, causes reaction not exclusively, and yield is low.
In the synthetic method of above-mentioned 3- methoxyl groups-N, N- dimethylpropionamide, the pressure in closed reactor is 0.1-
10.0MPa。
Preferably, the pressure in closed reactor is 0.5-5.0MPa.
Still further preferably, the pressure in closed reactor is 1-2MPa.
In the synthetic method of above-mentioned 3- methoxyl groups-N, N- dimethylpropionamide, reaction temperature is 90-110 DEG C.
In the synthetic method of above-mentioned 3- methoxyl groups-N, N- dimethylpropionamide, the thing of 3- methoxypropionic acids and dimethylamine
Mass ratio is 1:1-8.
Preferably, the amount of substance ratio of 3- methoxypropionic acids and dimethylamine is 1:1-2.
In the synthetic method of above-mentioned 3- methoxyl groups-N, N- dimethylpropionamide, described 3- methoxypropionic acids are by such as
Lower method synthesis：Acrylonitrile, absolute methanol and metal alkoxide are added in reactor carries out alkoxide reaction, then returns
Unreacted absolute methanol is received, 3- methoxypropionitriles are obtained；Again in 3- methoxypropionitriles add acidic catalyst and water, heat into
Row hydrolysis, obtains 3- methoxypropionic acids.
Preferably, described metal alkoxide is sodium methoxide, caustic alcohol, potassium methoxide, potassium ethoxide, magnesium methoxide, ethanol
One or more in magnesium, sodium tert-butoxide, potassium tert-butoxide.The present invention is catalyzed using the strong metal alkoxide of catalytic capability
Agent, and the convenient sources of metal alkoxide, be easy to get, cost it is relatively low.
Further preferably, described metal alkoxide be sodium methoxide, caustic alcohol in one or two.With other metals
Alkoxide is compared, and sodium methoxide is relatively strong with the activity of caustic alcohol, and cost is relatively low, with more preferable competitiveness.
Preferably, the amount of substance ratio of acrylonitrile, absolute methanol, metal alkoxide is 1:(1-50):(0.001-
0.05).The amount of material is excessive, can cause post processing when methyl alcohol yield it is larger, in turn result in loss it is larger, it is too small to cause
The concentration of substrate is larger in reaction system, so as to cause side reaction to increase, and then causes the yield to reduce.
Further preferably, acrylonitrile, absolute methanol, the amount of substance ratio of metal alkoxide are 1:(5-10):(0.005-
0.02)。
Preferably, the temperature of alkoxide reaction is 20-100 DEG C.
Further preferably, the temperature of alkoxide reaction is 50-60 DEG C.
Preferably, the temperature of hydrolysis is 80-120 DEG C.
Further preferably, the temperature of hydrolysis is 90-100 DEG C.
Preferably, 3- methoxypropionitriles are 1 with the amount of substance ratio of acidic catalyst:1-15.
Further preferably, 3- methoxypropionitriles and the amount of substance ratio of acidic catalyst are 1:1-3.
Preferably, described acidic catalyst is one or more in the concentrated sulfuric acid, hydrochloric acid, nitric acid, phosphoric acid.
Further preferably, described acidic catalyst be the concentrated sulfuric acid, hydrochloric acid in one or two.
Reaction of the prior art is essentially ester and is reacted with amine, and the source of ester is to obtain acrylic acid by acroleic acid esterification
Ester, then alkoxylate obtains β-alkoxy acrylic ester, reamination.The present invention reacts for acid with amine, can be less expensive using price
Acrylonitrile alkoxylate hydrolyze obtain methoxypropionic acid again.Polyalcohol is not needed in the present invention because the hair without side reaction
Raw, product in itself can be as solvent, it is not necessary to dilute again, without base catalyst because reaction to belong to acid-base neutralization anti-
Should, then high temperature dehydration again, it is easy to carry out, if introducing base catalyst, will not only work, methoxy can be consumed on the contrary
Base propionic acid, while introducing impurity.Furthermore, there is reversible reaction in order to avoid the volatilization of raw material amine under hot conditions in the present invention,
Need to be reacted in closed space.Present invention pollution while realizing in high yield is few, meets wanting for modern chemical industry green syt
Ask.
Reaction equation of the invention is as follows：
Wherein, 3- methoxypropionic acids are synthesized by following reaction equation：
In sum, it is raw material that the present invention uses 3- methoxypropionic acids, is dehydrated in closed reactor high temperature with dimethylamine
, it is not necessary to polyalcohol, base catalyst, easy reaction, and product yield high, purity are high, are realizing in high yield
Simultaneously pollution less, low cost, meet the requirement of modern chemical industry green syt.Meanwhile, 3- methoxypropionic acids of the present invention are with inexpensive
Acrylonitrile is initiation material, and acrylonitrile alkoxide obtains methoxypropionitrile, then hydrolyzes prepared, and simple to operate, energy consumption is low.
Specific embodiment
The following is specific embodiment of the invention, technical scheme is further described, but the present invention is simultaneously
It is not limited to these embodiments.
By the parameter in the embodiment 1-38 of table 1 and comparative example 3-20 and using the following method synthesis 3- methoxies of the present invention
Base-N, N- dimethylpropionamide：
The synthesis of S1,3- methoxypropionitrile：Acrylonitrile, absolute methanol and metal alkoxide are added in reactor
Alkoxide reaction is first carried out, the unreacted absolute methanol of recycling obtains 3- methoxypropionitriles；
The synthesis of S2,3- methoxypropionic acid：Acidic catalyst and water, heating are added to the 3- methoxypropionitriles in step S1
Be hydrolyzed reaction, obtains 3- methoxypropionic acids；
The synthesis of S3,3- methoxyl group-N, N- dimethylpropionamide：3- methoxypropionic acids and dimethylamine are added to closed anti-
Answer in device, temperature reaction obtains 3- methoxyl groups-N, N- dimethylpropionamide.
Table 1：
Can be obtained from the embodiment 1-8 of table 1 and comparative example 8-11, the synthesis of 3- methoxyl groups-N, N- dimethylpropionamide of the present invention
Temperature yield at 80-150 DEG C is higher in method, preferably 90-110 DEG C, most preferably preferably 100 DEG C, if temperature less than 80 DEG C or
The yield of final products can be all significantly affected higher than 150 DEG C.Can be obtained from the embodiment 9-14 of table 1 and comparative example 3-7,3- first of the present invention
Pressure in the synthetic method of epoxide-N, N- dimethylpropionamide in closed reactor in the range of 0.1-10.0MPa yield compared with
Height, preferably 0.5-2Mpa, further preferably 1-2MPa, optimal preferably 1.5MPa.Can be obtained from the embodiment 35-38 of table 1 and comparative example 20, this
The amount of substance ratio of 3- methoxypropionic acids and dimethylamine in the synthetic method of 3- methoxyl groups-N, N- dimethylpropionamide is invented 1:
Product yield is higher in the range of (1-8).Can be obtained from the embodiment 15-18 of table 1 and comparative example 12-14,3- methoxypropionic acids synthesis side
Heating response temperature in the method yield at 80-120 DEG C is higher, preferably 90-100 DEG C, most preferably preferably 95 DEG C.From the embodiment of table 1
19-24 and comparative example 15-17 can be obtained, the stirring reaction temperature in 3- methoxypropionic acid synthetic methods at 20-100 DEG C yield compared with
Height, most preferably preferably 50-60 DEG C, preferably 55 DEG C.Can be obtained from the embodiment 25-29 of table 1 and comparative example 18,3- methoxypropionic acids synthesis side
The amount of substance ratio of acrylonitrile, absolute methanol, metal alkoxide is 1 in method:(1-50):Product is received in the range of (0.001-0.05)
Rate is higher.Can be obtained from the embodiment 30-34 of table 1 and comparative example 19, the 3- methoxypropionitriles in 3- methoxypropionic acid synthetic methods with
The amount of substance ratio of acidic catalyst is 1:Product yield is higher in the range of (1-15).
Raw material is made using the 3- methoxypropionic acids for obtaining purchased in market in embodiment 39-40, by 3- methoxypropionic acids and dimethylamine
It is added in closed reactor, reacts to obtain 3- methoxyl groups-N, N- dimethylpropionamide after intensification under a certain pressure.Furtherly
The synthesis temperature of bright 3- methoxyl groups-N, N- dimethylpropionamide of the present invention is 90-110 DEG C, most preferably preferably 100 DEG C；Confined reaction
Kettle pressure is 1-2MPa, optimal preferably 1.5MPa；The amount of substance ratio of 3- methoxypropionic acids and dimethylamine is 1:(1-2), it is optimal excellent
Select 1:1.5.
In sum, it is raw material that the present invention uses 3- methoxypropionic acids, is dehydrated in closed reactor high temperature with dimethylamine
, it is not necessary to polyalcohol, base catalyst, easy reaction, and product yield high, purity are high, are realizing in high yield
Simultaneously pollution less, low cost, meet the requirement of modern chemical industry green syt.Meanwhile, 3- methoxypropionic acids of the present invention are with inexpensive
Acrylonitrile is initiation material, and acrylonitrile alkoxide obtains methoxypropionitrile, then hydrolyze it is prepared,
Randomly select 3- methoxyl groups-N, the N- dimethylpropionamide sample obtained using the inventive method synthesis and pass through gas phase
Chromatogram is detected.The gas chromatographic analysis result of sample is as shown in table 2 after detection.
Table 2：3- methoxyl groups-N, N- the dimethylpropionamide sample chromatogram analysis result obtained using the inventive method synthesis
| Peak number | Retention time | Peak area (uV*s) | Peak height (uV) | Purity (%) |
| 1 | 13.363 | 59.276 | 1390.806 | 0.0388 |
| 2 | 16.427 | 359842.781 | 3579131.250 | 99.9612 |
| Amount to | 359902.057 | 3580522.056 | 100.0000 |
As can be seen from Table 2：Using the inventive method 3- methoxyl groups-N, N- dimethylpropionamide purity for obtaining of synthesis compared with
Height, reaches 99.9612%.
Metal alkoxide can be sodium methoxide, caustic alcohol, potassium methoxide, potassium ethoxide, magnesium methoxide, ethanol in the above-described embodiments
One or more in magnesium, sodium tert-butoxide, potassium tert-butoxide.Acidic catalyst can be in the concentrated sulfuric acid, hydrochloric acid, nitric acid, phosphoric acid
Plant or various.Wherein, the amount=quality/molecular weight of material, if metal alkoxide is sodium methoxide, propylene in citing embodiment
Nitrile, absolute methanol, the amount of substance ratio of sodium methoxide are (m acrylonitrile g/53g/mol)：(m methyl alcohol g/32g/mol)：(m sodium methoxides g/
54g/mol), also calculated with this conversion mode in other embodiment.
Specific embodiment described herein is only to the spiritual explanation for example of the present invention.Technology neck belonging to of the invention
The technical staff in domain can be made various modifications or supplement to described specific embodiment or be substituted using similar mode, but simultaneously
Do not deviate by spirit of the invention or surmount scope defined in appended claims.
It is skilled to this area although having made a detailed description and being cited some specific embodiments to the present invention
For technical staff, as long as it is obvious that can be made various changes without departing from the spirit and scope of the present invention or corrected.
Claims (10)
- The synthetic method of 1.3- methoxyl groups-N, N- dimethylpropionamide, it is characterised in that described synthetic method is included 3- first Epoxide propionic acid and dimethylamine are added in closed reactor, are warming up to 80-150 DEG C and are reacted to obtain 3- methoxyl groups-N, N- dimethyl propylene Acid amides.
- 2. the synthetic method of 3- methoxyl groups-N, N- dimethylpropionamide according to claim 1, it is characterised in that closed Pressure in reactor is 0.1-10.0MPa.
- 3. the synthetic method of 3- methoxyl groups-N, N- dimethylpropionamide according to claim 1 and 2, it is characterised in that close The pressure closed in reactor is 0.5-5.0MPa.
- 4. the synthetic method of 3- methoxyl groups-N, N- dimethylpropionamide according to claim 3, it is characterised in that closed Pressure in reactor is 1-2MPa.
- 5. the synthetic method of 3- methoxyl groups-N, N- dimethylpropionamide according to claim 1, it is characterised in that reaction Temperature is 90-110 DEG C.
- 6. the synthetic method of 3- methoxyl groups-N, N- dimethylpropionamide according to claim 1, it is characterised in that 3- first The amount of substance ratio of epoxide propionic acid and dimethylamine is 1:1-8.
- 7. the synthetic method of 3- methoxyl groups-N, N- dimethylpropionamide according to claim 6, it is characterised in that 3- first The amount of substance ratio of epoxide propionic acid and dimethylamine is 1:1-2.
- 8. the synthetic method of 3- methoxyl groups-N, N- dimethylpropionamide according to claim 1, it is characterised in that described 3- methoxypropionic acids synthesize by the following method：Acrylonitrile, absolute methanol and metal alkoxide are added in reactor carries out alkoxide reaction, and recycling is not anti- The absolute methanol answered, obtains 3- methoxypropionitriles；Again to catalyst and water is added in 3- methoxypropionitriles, the reaction that is hydrolyzed is heated 3- methoxypropionic acids are obtained afterwards.
- 9. the synthetic method of 3- methoxyl groups-N, N- dimethylpropionamide according to claim 8, it is characterised in that described Metal alkoxide in sodium methoxide, caustic alcohol, potassium methoxide, potassium ethoxide, magnesium methoxide, magnesium ethylate, sodium tert-butoxide, potassium tert-butoxide One or more, described acidic catalyst is one or more in the concentrated sulfuric acid, hydrochloric acid, nitric acid, phosphoric acid.
- 10. the synthetic method of 3- methoxyl groups-N, N- dimethylpropionamide according to claim 8, it is characterised in that alcoxyl The temperature for changing reaction is 20-100 DEG C, and the temperature of hydrolysis is 80-120 DEG C.
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| CN108767235A (en) * | 2018-06-04 | 2018-11-06 | 广州天赐高新材料股份有限公司 | Cathode plate for lithium secondary battery slurry and its preparation method and application |
| 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 |
| CN111362827A (en) * | 2020-04-26 | 2020-07-03 | 江苏理工学院 | Process for catalytically synthesizing N, N-dimethylacrylamide |
| CN112271400A (en) * | 2020-09-01 | 2021-01-26 | 广州天赐高新材料股份有限公司 | Novel application of amide compound |
| 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 |
| CN113563228A (en) * | 2021-07-26 | 2021-10-29 | 山东汉鸿新材料科技有限公司 | Method for preparing 3-methoxypropionitrile |
| CN117964512A (en) * | 2024-04-01 | 2024-05-03 | 山东惟普控股有限公司 | Synthesis method of N, N-dimethyl-3-methoxy propionamide |
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| CN113004171B (en) * | 2021-03-09 | 2022-09-16 | 万华化学集团股份有限公司 | Preparation method of 3-methoxypropylamine |
| CN113563228A (en) * | 2021-07-26 | 2021-10-29 | 山东汉鸿新材料科技有限公司 | Method for preparing 3-methoxypropionitrile |
| CN117964512A (en) * | 2024-04-01 | 2024-05-03 | 山东惟普控股有限公司 | Synthesis method of N, N-dimethyl-3-methoxy propionamide |
| CN117964512B (en) * | 2024-04-01 | 2024-06-04 | 山东惟普控股有限公司 | Synthesis method of N, N-dimethyl-3-methoxy propionamide |
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