CN110511157A - A method of trifluoroacetamide is prepared using microchannel reaction technology - Google Patents
A method of trifluoroacetamide is prepared using microchannel reaction technology Download PDFInfo
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- CN110511157A CN110511157A CN201810495031.7A CN201810495031A CN110511157A CN 110511157 A CN110511157 A CN 110511157A CN 201810495031 A CN201810495031 A CN 201810495031A CN 110511157 A CN110511157 A CN 110511157A
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- ammonia
- trifluoroacetamide
- trifluoroacetic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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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Abstract
The invention discloses a kind of Trifluoroacetic Acid Ethyl Esters to react the method that serialization prepares trifluoroacetamide with ammonia, and in micro passage reaction, raw material Trifluoroacetic Acid Ethyl Ester is mixed and reacted in reaction module with ammonia, and trifluoroacetamide is obtained after quenching module.The method that invention provides have that high conversion rate, reaction time are short, reaction is safely controllable and can continuous chemical industry amplify.
Description
Technical field
The present invention relates to a kind of preparation methods of trifluoroacetamide, more particularly, to one kind in microchannel continuous reaction
The method for preparing trifluoroacetamide.
Background technique
Trifluoroacetamide is a kind of important Organic Chemicals, is mainly used to synthesize trifluoro acetonitrile and 2- trifluoromethyl-
The organofluorine compounds such as 4- carbethoxyl group -1,3-thiazoles, it can also be used to prepare pesticide, medicine and industrial chemical etc..Both at home and abroad
Have the synthesis of lot of documents, patent report amides compound, mainly by organic acid and its derivative for example acid anhydrides, acyl chlorides,
Ester etc. is reacted with raw material amine to be made, and having many products at present realizes large-scale industrial production.For trifluoroacetamide
Production method has following report in the prior art:
(1) PCT Patent Application WO03080563 discloses a kind of preparation method of trifluoroacetamide, with Trifluoroacetic Acid Ethyl Ester
For raw material, is reacted with ammonia and produce trifluoroacetamide.By the way that Trifluoroacetic Acid Ethyl Ester is put into reactor, it is passed through ammonia at room temperature
Gas, being heated to reaction temperature is 86 DEG C, collects the pure and mild ester generated using large container during reaction and recycles the former reaction of investment
In device, until vapor detection Trifluoroacetic Acid Ethyl Ester reacts completely, trifluoroacetamide crude product is prepared；
(2) PCT Patent Application WO 2010055474 discloses a kind of preparation method of trifluoroacetamide, with trifluoroacetic acid
For starting material, trifluoro-acetate is first prepared, then is reacted with the alcoholic solution of ammonia and prepares trifluoroacetamide.By the way that sulfuric acid is slow
Simultaneously ice bath stirring is added trifluoroacetic acid and stirs, then heat to 40 DEG C~45 DEG C after the solution is cooling simultaneously in instillation methanol
React 6h.After reaction solution cools down, add water washing, extraction removes organic phase, obtains trifluoroacetic acid first after being dried with anhydrous sodium sulfate
Ester.Ammonia-methanol solution is added into trifluoro-acetate, is during which cooled with an ice bath, is then stirred at room temperature overnight.It will reaction
Mixture rotary evaporation in vacuo afterwards, obtains white solid i.e. trifluoroacetamide.
The existing disclosed method for preparing trifluoroacetamide, reacts preparation with ammonia with trifluoro-acetate, although technique is simple
It is single, but reaction process is exothermic reaction, and ammonia can only be slowly passed through in entire reaction process, reaction process is complicated, is not easy
Operation, and reactivity hazard is high, can't carry out continuous production.
Therefore, it is necessary to which the preparation process to trifluoroacetamide is improved further.
Summary of the invention
The purpose of the present invention is to provide a kind of using microchannel reaction technology, Trifluoroacetic Acid Ethyl Ester is made to react company with ammonia
The method that continuousization prepares trifluoroacetamide, have the characteristics that process safety, it is easily operated, can be realized continuous production.
Synthesis route of the invention are as follows:
The invention provides the following technical scheme:
A kind of Trifluoroacetic Acid Ethyl Ester reacts the method that serialization prepares trifluoroacetamide with ammonia, and the method is in microchannel
It is carried out in reactor, comprising the following steps:
(1) raw material 1 is made to enter warm-up block 3, preheating temperature is 0~180 DEG C, and the raw material 1 includes Trifluoroacetic Acid Ethyl Ester；
(2) raw material 1 and raw material 2 after step (1) preheats is made to enter microchannel reaction module 4, the raw material 2 includes ammonia
Gas, raw material 2 are mixed and are reacted in the microchannel reaction module with raw material 1, and the mol ratio of the raw material 2 and raw material 1 is
2.0:1~1.0:1,1 flow of raw material are 5~40g/min, and reaction temperature is 0~180 DEG C, and reaction pressure is 0~1.0MPa；
(3) compound that reaction module 9 exit in step (2) microchannel obtains arrives trifluoro after quenching module 10
Ethamine crude product.
Trifluoroacetic Acid Ethyl Ester provided by the invention reacts serialization with ammonia and prepares trifluoroacetamide, will be micro- logical before preparation
Reactor each module in road is assembled to obtain micro passage reaction.As an example, one piece can be preheated according to shown in attached drawing 3
3, six pieces of microchannel reaction modules 4~9 of module and one piece of quenching module 10 carry out tandem installation, in which: with 3 phase of warm-up block
1 even is liquid phase pump, the feed inlet as raw material 1；1 to be connected with microchannel reaction module 4 is gas mass flow meter, as
2 feed inlet of raw material.
After micro passage reaction connects, conduction oil can be used and conduct heat.Company is reacted with ammonia in trifluoroacetamide
During continuousization prepares trifluoroacetamide, it can according to need and increase or decrease microchannel reaction module, can according to need choosing
It selects 2 pieces or 2 pieces or more microchannel reaction modules and participates in reaction.
Trifluoroacetic Acid Ethyl Ester provided by the invention reacts serialization with ammonia and prepares in trifluoroacetamide method, as preferred
Mode, the mass tranfer coefficient of the micro passage reaction is 1~30Ka, exchange capability of heat 1700KW/m2K or more.
Trifluoroacetic Acid Ethyl Ester provided by the invention reacts serialization with ammonia and prepares in trifluoroacetamide method, as preferred
Mode, the micro passage reaction is that healthy and free from worry G2 microreactor, microwell array decline channel reactor, finned microchannel plate
Answer device, capillary microchannels reactor or multiply parallel type microreactor.
Trifluoroacetic Acid Ethyl Ester provided by the invention reacts serialization with ammonia and prepares in trifluoroacetamide method, described micro- logical
Microchannel structure in the reaction module of road reactor includes once-through type channel design and enhancing mixed type channel design.Preferably
It is that the once-through type channel design is tubular structure, the enhancing mixed type channel design is T-type structure, spherical structure, spherical shape
Band baffle arrangement, drops structure or heart-shaped structure, and channel diameter is 0.5mm~10mm.
Trifluoroacetic Acid Ethyl Ester provided by the invention reacts serialization with ammonia and prepares trifluoroacetamide method, the microchannel
The material of reaction module is selected from glass, silicon carbide, breathes out C alloy or manganese Nai Er alloy.
Trifluoroacetic Acid Ethyl Ester provided by the invention reacts serialization with ammonia and prepares in trifluoroacetamide method, raw material 1 into
It before entering warm-up block 3, is preheated, preheating temperature is 0~180 DEG C.Preferably, the preheating temperature is 50~140
℃。
Trifluoroacetic Acid Ethyl Ester provided by the invention reacts serialization with ammonia and prepares in trifluoroacetamide method, raw material 1 with
The mol ratio satisfaction of raw material 2 goes on smoothly reaction.As a preferred mode, the raw material 2 and raw material 1 rub
Your proportion is 2.0:1~1.0:1.As further preferred mode, the mol ratio of the raw material 2 and raw material 1 be 1.2:1~
1.05:1。
Trifluoroacetic Acid Ethyl Ester provided by the invention reacts serialization with ammonia and prepares in trifluoroacetamide method, raw material 2
Flow satisfaction goes on smoothly reaction.As a preferred mode, 1 flow of raw material is 5~40g/min.
Trifluoroacetic Acid Ethyl Ester provided by the invention reacts serialization with ammonia and prepares in trifluoroacetamide method, step (2)
Middle reaction temperature is 0~180 DEG C.As a preferred mode, the reaction temperature is 50~120 DEG C.
Trifluoroacetic Acid Ethyl Ester provided by the invention reacts serialization with ammonia and prepares in trifluoroacetamide method, step (2)
Middle 0~1.0MPa of reaction pressure.As a preferred mode, the reaction pressure is 0~0.5MPa.
Trifluoroacetic Acid Ethyl Ester provided by the invention reacts serialization with ammonia and prepares in trifluoroacetamide method, with existing skill
Art is compared, and has many advantages, such as that the reaction time is short, reaction is safely controllable and can continuous chemical industry amplification.
Detailed description of the invention
Fig. 1 is the typical structure unit figure of micro passage reaction module used in the present invention；
Fig. 2 is institute of the invention to module map for Corning micro passage reaction；
Fig. 3 is institute of the invention to micro channel reactor system device figure for Corning microchannel module, and in Fig. 3:
1 it is liquid phase pump (1 feed inlet of raw material), 2 be gas mass flow meter (2 feed inlet of raw material), 3 be warm-up block, 4~9 is micro- logical
Road reaction module, 10 are quenching module.
Specific embodiment
Next combined with specific embodiments below invention is further explained, but does not limit the invention to these tools
Body embodiment.One skilled in the art would recognize that present invention encompasses may include in Claims scope
All alternatives, improvement project and equivalent scheme.
Embodiment 1
Select 1 piece of corning straight channel module in attached drawing 2 (as premix warm-up block 3), corning " heart " micro- logical
6 pieces of road reaction module, 1 piece of corning straight channel module (as quenching module 10).It is formed according to reaction process shown in attached drawing 3
Continuous flow microchannel reaction system.Reacting replacing heat medium uses conduction oil.Heat transfer theory is forced according to micro passage reaction, is only existed
Two temperature measuring points are arranged in the reactor feed mouth and discharge port.Microchannel reaction system and connecting line are carried out respectively before reaction
Water removal is dried, and carries out 1.0MPa airtight test.By 1 liquid phase pump (such as diaphragm metering pump) in attached drawing 3, to microchannel
Raw material Trifluoroacetic Acid Ethyl Ester is added in reaction system continuous-stable.By 2 gas mass flow meters in attached drawing 3, to microchannel plate
Answer system continuous and quantitative that ammonia is added.
75 DEG C of heat exchange temperature of setting, i.e. reaction temperature set reaction pressure 0MPa.Raw material Trifluoroacetic Acid Ethyl Ester, charging
Speed is 9.46g/min, and ammonia feed speed is 1.13g/min, and the residence time of reaction is 6s, ammonia and Trifluoroacetic Acid Ethyl Ester
Mol ratio be 1.0:1.Reaction raw materials enter " heart " microchannel reaction module 4, ammonia after microchannel premixes warm-up block 3
Gas is directly entered " heart " microchannel reaction module 4 by gas mass flow meter, in " heart " microchannel reaction module 4-9
In, ammonia is reacted with Trifluoroacetic Acid Ethyl Ester.Crude reaction collects after quenching module 10 and obtains the crude product of trifluoroacetamide.
GC analysis is carried out to the crude product mixed liquor of reaction, the results showed that, the conversion ratio of Trifluoroacetic Acid Ethyl Ester is 92.60%,
The selectivity of trifluoroacetamide is 99.36%.
Embodiment 2
Using healthy and free from worry micro passage reaction similarly to Example 1, and according to same connection type and control method.This
Embodiment changes reaction condition.
80 DEG C of heat exchange temperature of setting, i.e. reaction temperature set reaction pressure 0MPa.Raw material Trifluoroacetic Acid Ethyl Ester, charging
Speed is 10.93g/min, and ammonia feed speed is 1.70g/min, and the residence time of reaction is 4s, ammonia and trifluoroacetic acid second
The mol ratio of ester is 1.3:1.Reaction raw materials enter " heart " microchannel reaction module 4 after microchannel premixes warm-up block 3,
Ammonia is directly entered " heart " microchannel reaction module 4 by gas mass flow meter, in " heart " microchannel reaction module 4-9
In, ammonia is reacted with Trifluoroacetic Acid Ethyl Ester.Crude reaction collects after quenching module 10 and obtains the crude product of trifluoroacetamide.
GC analysis is carried out to the crude product mixed liquor of reaction, the results showed that, the conversion ratio of Trifluoroacetic Acid Ethyl Ester is 99.91%,
The selectivity of trifluoroacetamide is 99.24%.
Embodiment 3
Using healthy and free from worry micro passage reaction similarly to Example 1, and according to same connection type and control method.This
Embodiment changes reaction condition.
100 DEG C of heat exchange temperature of setting, i.e. reaction temperature set reaction pressure 0.1MPa.Raw material Trifluoroacetic Acid Ethyl Ester, into
Material speed is 12.91g/min, and ammonia feed speed is 1.70g/min, and the residence time of reaction is 8s, ammonia and trifluoroacetic acid
The mol ratio of ethyl ester is 1.1:1.Reaction raw materials enter " heart " microchannel reaction module after microchannel premixes warm-up block 3
4, ammonia is directly entered " heart " microchannel reaction module 4 by gas mass flow meter, in " heart " microchannel reaction module
In 4-9, ammonia is reacted with Trifluoroacetic Acid Ethyl Ester.Crude reaction collects after quenching module 10 and obtains the crude product of trifluoroacetamide.
GC analysis is carried out to the crude product mixed liquor of reaction, the results showed that, the conversion ratio of Trifluoroacetic Acid Ethyl Ester is 99.34%,
The selectivity of trifluoroacetamide is 99.29%.
Embodiment 4
Using healthy and free from worry micro passage reaction similarly to Example 1, and according to same connection type and control method.This
Embodiment changes reaction condition.
100 DEG C of heat exchange temperature of setting, i.e. reaction temperature set reaction pressure 0.2MPa.Raw material Trifluoroacetic Acid Ethyl Ester, into
Material speed is 15.49g/min, and ammonia feed speed is 2.04g/min, and the residence time of reaction is 10s, ammonia and trifluoroacetic acid
The mol ratio of ethyl ester is 1.1:1.Reaction raw materials enter " heart " microchannel reaction module after microchannel premixes warm-up block 3
4, ammonia is directly entered " heart " microchannel reaction module 4 by gas mass flow meter, in " heart " microchannel reaction module
In 4-9, ammonia is reacted with Trifluoroacetic Acid Ethyl Ester.Crude reaction collects after quenching module 10 and obtains the crude product of trifluoroacetamide.
GC analysis is carried out to the crude product mixed liquor of reaction, the results showed that, the conversion ratio of Trifluoroacetic Acid Ethyl Ester is 99.18%,
The selectivity of trifluoroacetamide is 99.12%.
Embodiment 5
Using healthy and free from worry micro passage reaction similarly to Example 1, and according to same connection type and control method.This
Embodiment changes reaction condition.
100 DEG C of heat exchange temperature of setting, i.e. reaction temperature set reaction pressure 0MPa.Raw material Trifluoroacetic Acid Ethyl Ester, charging
Speed is 6.46g/min, and ammonia feed speed is 0.85g/min, and the residence time of reaction is 8s, ammonia and Trifluoroacetic Acid Ethyl Ester
Mol ratio be 1.1:1.Reaction raw materials enter " heart " microchannel reaction module 4, ammonia after microchannel premixes warm-up block 3
Gas is directly entered " heart " microchannel reaction module 4 by gas mass flow meter, in " heart " microchannel reaction module 4-9
In, ammonia is reacted with Trifluoroacetic Acid Ethyl Ester.Crude reaction collects after quenching module 10 and obtains the crude product of trifluoroacetamide.
GC analysis is carried out to the crude product mixed liquor of reaction, the results showed that, the conversion ratio of Trifluoroacetic Acid Ethyl Ester is 98.75%,
The selectivity of trifluoroacetamide is 99.44%.
Embodiment 6
Using healthy and free from worry micro passage reaction similarly to Example 1, and according to same connection type and control method.This
Embodiment changes reaction condition.
100 DEG C of heat exchange temperature of setting, i.e. reaction temperature set reaction pressure 0MPa.Raw material Trifluoroacetic Acid Ethyl Ester, charging
Speed is 7.89g/min, and ammonia feed speed is 1.13g/min, and the residence time of reaction is 6s, ammonia and Trifluoroacetic Acid Ethyl Ester
Mol ratio be 1.2:1.Reaction raw materials enter " heart " microchannel reaction module 4, ammonia after microchannel premixes warm-up block 3
Gas is directly entered " heart " microchannel reaction module 4 by gas mass flow meter, in " heart " microchannel reaction module 4-9
In, ammonia is reacted with Trifluoroacetic Acid Ethyl Ester.Crude reaction collects after quenching module 10 and obtains the crude product of trifluoroacetamide.
GC analysis is carried out to the crude product mixed liquor of reaction, the results showed that, the conversion ratio of Trifluoroacetic Acid Ethyl Ester is 99.62%,
The selectivity of trifluoroacetamide is 99.20%.
Claims (8)
1. a kind of Trifluoroacetic Acid Ethyl Ester reacts the method that serialization prepares trifluoroacetamide with ammonia, it is characterised in that the method
It is carried out in micro passage reaction, comprising the following steps:
(1) raw material 1 is made to enter warm-up block 3, preheating temperature is 0~180 DEG C, and the raw material 1 includes Trifluoroacetic Acid Ethyl Ester；
(2) raw material 1 and raw material 2 after step (1) preheats is made to enter microchannel reaction module 4, the raw material 2 includes ammonia,
Raw material 2 is mixed and is reacted in the microchannel reaction module with raw material 1, and the mol ratio of the raw material 2 and raw material 1 is 2.0:
1~1.0:1,1 flow of raw material are 5~40g/min, and reaction temperature is 0~180 DEG C, and reaction pressure is 0~1.0MPa；
(3) compound that reaction module 9 exit in step (2) microchannel obtains arrives trifluoroethylamine after quenching module 10
Crude product.
2. Trifluoroacetic Acid Ethyl Ester described in accordance with the claim 1 reacts the method that serialization prepares trifluoroacetamide with ammonia,
The mol ratio for being characterized in that the raw material 2 and raw material 1 is 1.2:1~1.05:1, and preheating temperature is 50~140 in step (1)
℃。
3. Trifluoroacetic Acid Ethyl Ester reacts the method that serialization prepares trifluoroacetamide with ammonia according to claim 2,
It is characterized in that in the step (2) that reaction temperature is 50~120 DEG C.
4. Trifluoroacetic Acid Ethyl Ester described in accordance with the claim 1 reacts the method that serialization prepares trifluoroacetamide with ammonia,
It is characterized in that in the step (2) that reaction pressure is 0~0.5MPa.
5. Trifluoroacetic Acid Ethyl Ester described in accordance with the claim 1 reacts the method that serialization prepares trifluoroacetamide with ammonia,
In step described in feature (2), raw material 2 is mixed and is reacted in two or more microchannel reaction modules with raw material 1.
6. Trifluoroacetic Acid Ethyl Ester described in accordance with the claim 1 reacts the method that serialization prepares trifluoroacetamide with ammonia,
Be characterized in that: microchannel reaction module described in step (2), material are selected from silicon carbide, breathe out C alloy or manganese Nai Er alloy, institute
The mass tranfer coefficient for stating micro passage reaction is 1~30Ka, exchange capability of heat 1700KW/m2K or more.
7. Trifluoroacetic Acid Ethyl Ester described in accordance with the claim 1 reacts the method that serialization prepares trifluoroacetamide with ammonia,
Be characterized in that: the reaction module of the micro passage reaction, internal microchannel structure includes once-through type channel design and increasing
Strong mixed type channel design, the once-through type channel design are tubular structure, and the enhancing mixed type channel design is T junction
Structure, spherical structure, spherical band baffle arrangement, drops structure or heart-shaped structure, and channel diameter is 0.5mm~10mm.
8. Trifluoroacetic Acid Ethyl Ester described in accordance with the claim 1 reacts the method that serialization prepares trifluoroacetamide with ammonia,
Be characterized in that: the micro passage reaction is that healthy and free from worry G2 microreactor, microwell array decline channel reactor, finned microchannel
Reactor, capillary microchannels reactor or multiply parallel type microreactor.
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| CN112978689A (en) * | 2019-12-18 | 2021-06-18 | 浙江蓝天环保高科技股份有限公司 | Continuous preparation method of bis (fluorosulfonyl) imide |
| CN113429310A (en) * | 2021-08-02 | 2021-09-24 | 大连理工大学 | Continuous preparation method of 2-amino malonamide |
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| CN112978689A (en) * | 2019-12-18 | 2021-06-18 | 浙江蓝天环保高科技股份有限公司 | Continuous preparation method of bis (fluorosulfonyl) imide |
| CN112978689B (en) * | 2019-12-18 | 2022-05-24 | 浙江蓝天环保高科技股份有限公司 | Continuous preparation method of bis (fluorosulfonyl) imide |
| CN111848434A (en) * | 2020-08-05 | 2020-10-30 | 山东亿盛实业股份有限公司 | Synthetic method of 2-nitro-N, 3-dimethylbenzamide |
| CN111848434B (en) * | 2020-08-05 | 2023-04-11 | 山东亿盛实业股份有限公司 | Synthetic method of 2-nitro-N, 3-dimethylbenzamide |
| CN112176009A (en) * | 2020-09-30 | 2021-01-05 | 江苏暨明医药科技有限公司 | Method for continuously preparing 3-phthalimido propionaldehyde in batches by utilizing microreactor |
| CN113429310A (en) * | 2021-08-02 | 2021-09-24 | 大连理工大学 | Continuous preparation method of 2-amino malonamide |
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