CN106905189B - Microreactor system and method for bis- (propionitrile) the ether synthesis of ethylene glycol - Google Patents
Microreactor system and method for bis- (propionitrile) the ether synthesis of ethylene glycol Download PDFInfo
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- CN106905189B CN106905189B CN201710118057.5A CN201710118057A CN106905189B CN 106905189 B CN106905189 B CN 106905189B CN 201710118057 A CN201710118057 A CN 201710118057A CN 106905189 B CN106905189 B CN 106905189B
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- ethylene glycol
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- propionitrile
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- reaction channel
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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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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
Abstract
This application discloses a kind of microreactor system and method for bis- (propionitrile) the ether synthesis of ethylene glycol, this method comprises: first device is passed through acrylonitrile；Second device is passed through the mixture of basic catalyst and ethylene glycol, and the molar ratio control of acrylonitrile and ethylene glycol is in (2.4~2.5): 1；Acrylonitrile, basic catalyst and the ethylene glycol hybrid reaction in reaction channel control reaction temperature at 120 DEG C~150 DEG C by temperature control device, and the reaction time is 3~4min；Product pH is modulated 4~5, extracts away moisture, excessive propene nitrile is removed and obtains bis- (propionitrile) ethers of ethylene glycol.The present invention carries out in microreactor, effectively avoids security risk, and due to the excellent mass transfer effect of microreactor, reaction quickly can be carried out adequately.The present invention can effectively solve the defect of the prior art, and simple process, the reaction time is short, and selectivity is high, and high conversion rate, low energy consumption, can be continuously produced, and bis- (propionitrile) the ether purity of the ethylene glycol of preparation are up to 96.8% (GC).
Description
Technical field
The application belongs to chemical synthesis and microchannel reaction technology, is used for bis- (propionitrile) ethers of ethylene glycol more particularly to one kind
The microreactor system and method for synthesis.
Background technique
It is a kind of important method for preparing ether nitrile that Michael addition reaction, which occurs, for alcohol and acrylonitrile, and ether nitrile is as a kind of function
Energy property chemical products, play an important role in multiple fields such as chemical industry, medicine, pesticides.Currently, ether nitrile needed for domestic market
Import, higher cost are also relied on mostly, therefore the synthesis for studying ether nitrile has the development of domestic chemical industry to have biggish meaning.
The prior art: by ethylene glycol be added to equipped with thermometer, magnetic stir bar four-hole boiling flask in, be added at room temperature
Sodium hydroxide solution stirring, is then slowly added dropwise acrylonitrile from constant pressure funnel, and the process that is added dropwise keeps temperature-resistant,
It heats up after being added dropwise, waits reaction to terminate, then filter, vacuum distillation obtains product.
The synthetic technology of existing bis- (propionitrile) ethers of ethylene glycol uses traditional batch technology, not high, the side reaction of selectivity
Product be difficult to handle, cause product purity lower, so that the synthesis cost of bis- (propionitrile) ethers of ethylene glycol is higher, and anti-
Longer between seasonable, there are security risks.
Summary of the invention
Long it is an object of the invention to solve the reaction time of the existing technology, feed stock conversion is low, and reaction cost is high
The disadvantages of with serialization preparation is unable to, provides a kind of microreactor system and method for bis- (propionitrile) the ether synthesis of ethylene glycol.
To achieve the above object, the invention provides the following technical scheme:
The embodiment of the present application discloses a kind of microreactor system for bis- (propionitrile) the ether synthesis of ethylene glycol, comprising:
Continuous flow reactor has reaction channel, which includes two entrances and one outlet；
Temperature control device is connected to the continuous flow reactor；
Raw material and driving device, are connected to the entrance of the reaction channel, including first device and second device, and described
One device and second device are respectively communicated in the two entrances of the reaction channel；
Collection of products device is connected to the outlet of the reaction channel.
Preferably, in the above-mentioned microreactor system for bis- (propionitrile) the ether synthesis of ethylene glycol, the temperature control device
For a heat exchanger, which is connected to the continuous flow reactor and forms loop temperature-control between continuous flow reactor and return
Road；
Preferably, in the above-mentioned microreactor system for bis- (propionitrile) the ether synthesis of ethylene glycol, the reaction channel
Curve extends.
Preferably, in the above-mentioned microreactor system for bis- (propionitrile) the ether synthesis of ethylene glycol, the first device
Metering pump and check valve are disposed between the entrance of reaction channel.
Preferably, in the above-mentioned microreactor system for bis- (propionitrile) the ether synthesis of ethylene glycol, the second device
Metering pump and check valve are disposed between the entrance of reaction channel.
Correspondingly, disclosed herein as well is a kind of methods of bis- (propionitrile) ethers of synthesizing glycol, comprising:
First device is passed through acrylonitrile；
Second device is passed through the mixture of basic catalyst and ethylene glycol, and the molar ratio control of acrylonitrile and ethylene glycol exists
(2.4~2.5): 1；
Acrylonitrile, basic catalyst and the ethylene glycol hybrid reaction in reaction channel control reaction temperature by temperature control device
For degree at 120 DEG C~150 DEG C, the reaction time is 3~4min；
Product pH is modulated 4~5, extracts away moisture, excessive propene nitrile is removed and obtains bis- (propionitrile) ethers of ethylene glycol.
Preferably, in the method for above-mentioned bis- (propionitrile) ethers of synthesizing glycol, the basic catalyst be potassium tert-butoxide,
KOH, NaOH or triethylamine.
Preferably, in the method for above-mentioned bis- (propionitrile) ethers of synthesizing glycol, the reaction time is 3min, reaction temperature
Degree is 120 DEG C, and the molar ratio of acrylonitrile and ethylene glycol is 2.4.
Preferably, in the method for above-mentioned bis- (propionitrile) ethers of synthesizing glycol, mole of basic catalyst and ethylene glycol
Than for 1:210.
Compared with the prior art, the advantages of the present invention are as follows: the present invention carries out in microreactor, effectively avoids safety hidden
Suffer from, due to the excellent mass transfer effect of microreactor, reaction quickly can be carried out adequately.The present invention can effectively solve existing skill
The defect of art, simple process, the reaction time is short, and selectivity is high, and high conversion rate, low energy consumption, can be continuously produced.
Detailed description of the invention
In order to illustrate the technical solutions in the embodiments of the present application or in the prior art more clearly, to embodiment or will show below
There is attached drawing needed in technical description to be briefly described, it should be apparent that, the accompanying drawings in the following description is only this
The some embodiments recorded in application, for those of ordinary skill in the art, without creative efforts,
It is also possible to obtain other drawings based on these drawings.
Fig. 1 show the schematic illustration of microreactor system in the specific embodiment of the invention；
Fig. 2 show the gas chromatogram (areas of peak normalization method measurement content) of product in the specific embodiment of the invention；
Fig. 3 show the analysis result table of product in the specific embodiment of the invention.
Specific embodiment
Technical solution of the present invention is clearly and completely described below in conjunction with attached drawing, it is clear that described implementation
Example is a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, ordinary skill
Personnel's every other embodiment obtained without making creative work, shall fall within the protection scope of the present invention.
In the description of the present invention, it should be noted that term " center ", "upper", "lower", "left", "right", "vertical",
The orientation or positional relationship of the instructions such as "horizontal", "inner", "outside" be based on the orientation or positional relationship shown in the drawings, merely to
Convenient for description the present invention and simplify description, rather than the device or element of indication or suggestion meaning must have a particular orientation,
It is constructed and operated in a specific orientation, therefore is not considered as limiting the invention.In addition, term " first ", " second ",
" third " is used for descriptive purposes only and cannot be understood as indicating or suggesting relative importance.
In the description of the present invention, it should be noted that unless otherwise clearly defined and limited, term " installation ", " phase
Even ", " connection " shall be understood in a broad sense, for example, it may be being fixedly connected, may be a detachable connection, or be integrally connected；It can
To be mechanical connection, it is also possible to be electrically connected；It can be directly connected, can also can be indirectly connected through an intermediary
Connection inside two elements.For the ordinary skill in the art, above-mentioned term can be understood at this with concrete condition
Concrete meaning in invention.
In conjunction with described in Fig. 1, microreactor system include continuous flow reactor 1, temperature control device 2, raw material and driving device and
Collection of products device 3.
Continuous flow reactor 1 has reaction channel 101, which includes two entrances 102 and one outlet
103。
Continuous flow reactor 1 is a micro-fluidic chip, generally includes be superimposed up and down two substrates, wherein upper substrate
Material is preferably PDMS, and the material of lower substrate is preferably glass, and reaction channel is formed between two substrates.
Continuous flow reactor model is preferably WH-LAB-SS504-M.
Further, 101 curve of reaction channel extends, first is that can increase reaction distance, the reaction time is controlled, second is that can
To play the role of liquid mixing.
Temperature control device 2 is connected to the continuous flow reactor, controls to the temperature to reaction channel.
Preferably, temperature control device is a heat exchanger, which is connected to the continuous flow reactor and anti-with continuous flow
Answer formation loop temperature-control circuit between device.
Heat exchanger model is preferably WH-LAB-heatexchange.
Raw material and driving device are connected to the entrance of reaction channel, including first device 4 and second device 5, first device
4 and second device 5 be respectively communicated with the two entrances in reaction channel.
Further, metering pump 6 and check valve 7 are disposed between first device 4 and the entrance of reaction channel.Second
Metering pump 8 and check valve 9 are disposed between device 5 and the entrance of reaction channel.
Collection of products device 3 is connected to the outlet 103 of reaction channel.
Include: using the method that microreactor prepares bis- (propionitrile) ethers of diethanol
By acrylonitrile, basic catalyst and ethylene glycol are pumped into the reaction unit of microchannel simultaneously, and wherein acrylonitrile is from first
Device is passed through, and the mixture of basic catalyst and ethylene glycol is passed through from second device, and the molar ratio of acrylonitrile and ethylene glycol is 2.4
~2.5:1 stops 3~4min at 120 DEG C~150 DEG C；
Product pH is modulated 4~5, extracts away moisture, it is bis- (propionitrile) that revolving removing excessive propene nitrile can obtain ethylene glycol
Ether.
Reaction equation is as follows:
Basic catalyst is selected from potassium tert-butoxide, KOH, NaOH or triethylamine, and in a most preferred embodiment, basic catalyst is
The molar ratio of potassium tert-butoxide, potassium tert-butoxide and ethylene glycol is 1:210.
In a most preferred embodiment, the optimum temperature of reaction is at 120 DEG C；Acrylonitrile and the optimal molar ratio 2.4 of ethylene glycol:
1；Optimal residence time 3min.
Fig. 2 show the gas chromatogram (areas of peak normalization method measurement content) of product.
Fig. 3 show the analysis result table of product.Wherein, 1 is excessive propene nitrile；2 be target product ethylene glycol bis- (third
Nitrile) ether；Acrylonitrile easily removes.Reaction condition is acrylonitrile and ethylene glycol molar ratio 2.4:1；120 DEG C of temperature, the residence time
3min。
In conclusion effect of the invention includes at least:
(1), acrylonitrile and glycol reaction prepare the continuous flow production technology of the double propionitrile ethers of ethylene glycol, and single step reaction is just
Product can be obtained.
(2), process safety is stablized, last handling process very simple.
(3), sufficiently, completely, product purity is up to 96.8% for raw material conversion for reaction.
Finally, it should be noted that the above embodiments are only used to illustrate the technical solution of the present invention., rather than its limitations；To the greatest extent
Pipe present invention has been described in detail with reference to the aforementioned embodiments, those skilled in the art should understand that: its according to
So be possible to modify the technical solutions described in the foregoing embodiments, or to some or all of the technical features into
Row equivalent replacement；And these are modified or replaceed, various embodiments of the present invention technology that it does not separate the essence of the corresponding technical solution
The range of scheme.
Claims (7)
1. the method that one kind is based on bis- (propionitrile) ethers of microreactor system synthesis ethylene glycol, which is characterized in that
Microreactor system includes:
Continuous flow reactor has reaction channel, which includes two entrances and one outlet；
Temperature control device is connected to the continuous flow reactor；
Raw material and driving device are connected to the entrance of the reaction channel, including first device and second device, first dress
It sets and is respectively communicated with second device in the two entrances of the reaction channel；
Collection of products device is connected to the outlet of the reaction channel,
The method of bis- (propionitrile) ethers of synthesizing glycol includes:
First device is passed through acrylonitrile；
Second device is passed through the mixture of basic catalyst and ethylene glycol, the molar ratio control of acrylonitrile and ethylene glycol (2.4~
2.5): 1；
Acrylonitrile, basic catalyst and the ethylene glycol hybrid reaction in reaction channel control reaction temperature by temperature control device and exist
120 DEG C~150 DEG C, the reaction time is 3~4min；
Product pH is modulated 4~5, extracts away moisture, excessive propene nitrile is removed and obtains bis- (propionitrile) ethers of ethylene glycol,
Basic catalyst is potassium tert-butoxide.
2. the method for bis- (propionitrile) ethers of synthesizing glycol according to claim 1, it is characterised in that: the reaction time is
3min, reaction temperature are 120 DEG C, and the molar ratio of acrylonitrile and ethylene glycol is 2.4.
3. the method for bis- (propionitrile) ethers of synthesizing glycol according to claim 1, it is characterised in that: basic catalyst and second
The molar ratio of glycol is 1:210.
4. the method that one kind is based on bis- (propionitrile) ethers of microreactor system synthesis ethylene glycol, which is characterized in that
Microreactor system includes:
Continuous flow reactor has reaction channel, which includes two entrances and one outlet；
Temperature control device is connected to the continuous flow reactor, and the temperature control device is a heat exchanger, which is connected to described
Continuous flow reactor simultaneously forms loop temperature-control circuit between continuous flow reactor；
Raw material and driving device are connected to the entrance of the reaction channel, including first device and second device, first dress
It sets and is respectively communicated with second device in the two entrances of the reaction channel；
Collection of products device is connected to the outlet of the reaction channel,
The method of bis- (propionitrile) ethers of synthesizing glycol includes:
First device is passed through acrylonitrile；
Second device is passed through the mixture of basic catalyst and ethylene glycol, the molar ratio control of acrylonitrile and ethylene glycol (2.4~
2.5): 1；
Acrylonitrile, basic catalyst and the ethylene glycol hybrid reaction in reaction channel control reaction temperature by temperature control device and exist
120 DEG C~150 DEG C, the reaction time is 3~4min；
Product pH is modulated 4~5, extracts away moisture, excessive propene nitrile is removed and obtains bis- (propionitrile) ethers of ethylene glycol,
Basic catalyst is potassium tert-butoxide.
5. the method that one kind is based on bis- (propionitrile) ethers of microreactor system synthesis ethylene glycol, which is characterized in that
Microreactor system includes:
Continuous flow reactor has reaction channel, which includes two entrances and one outlet, and the reaction channel is bent
Line extends；
Temperature control device is connected to the continuous flow reactor；
Raw material and driving device are connected to the entrance of the reaction channel, including first device and second device, first dress
It sets and is respectively communicated with second device in the two entrances of the reaction channel；
Collection of products device is connected to the outlet of the reaction channel,
The method of bis- (propionitrile) ethers of synthesizing glycol includes:
First device is passed through acrylonitrile；
Second device is passed through the mixture of basic catalyst and ethylene glycol, the molar ratio control of acrylonitrile and ethylene glycol (2.4~
2.5): 1；
Acrylonitrile, basic catalyst and the ethylene glycol hybrid reaction in reaction channel control reaction temperature by temperature control device and exist
120 DEG C~150 DEG C, the reaction time is 3~4min；
Product pH is modulated 4~5, extracts away moisture, excessive propene nitrile is removed and obtains bis- (propionitrile) ethers of ethylene glycol,
Basic catalyst is potassium tert-butoxide.
6. the method that one kind is based on bis- (propionitrile) ethers of microreactor system synthesis ethylene glycol, which is characterized in that
Microreactor system includes:
Continuous flow reactor has reaction channel, which includes two entrances and one outlet；
Temperature control device is connected to the continuous flow reactor；
Raw material and driving device are connected to the entrance of the reaction channel, including first device and second device, first dress
It sets and is respectively communicated between the two entrances of the reaction channel, the first device and the entrance of reaction channel with second device
It is disposed with metering pump and check valve；
Collection of products device is connected to the outlet of the reaction channel,
The method of bis- (propionitrile) ethers of synthesizing glycol includes:
First device is passed through acrylonitrile；
Second device is passed through the mixture of basic catalyst and ethylene glycol, the molar ratio control of acrylonitrile and ethylene glycol (2.4~
2.5): 1；
Acrylonitrile, basic catalyst and the ethylene glycol hybrid reaction in reaction channel control reaction temperature by temperature control device and exist
120 DEG C~150 DEG C, the reaction time is 3~4min；
Product pH is modulated 4~5, extracts away moisture, excessive propene nitrile is removed and obtains bis- (propionitrile) ethers of ethylene glycol,
Basic catalyst is potassium tert-butoxide.
7. the method that one kind is based on bis- (propionitrile) ethers of microreactor system synthesis ethylene glycol, which is characterized in that
Microreactor system includes:
Continuous flow reactor has reaction channel, which includes two entrances and one outlet；
Temperature control device is connected to the continuous flow reactor；
Raw material and driving device are connected to the entrance of the reaction channel, including first device and second device, first dress
It sets and is respectively communicated between the two entrances of the reaction channel, the second device and the entrance of reaction channel with second device
It is disposed with metering pump and check valve；
Collection of products device is connected to the outlet of the reaction channel,
The method of bis- (propionitrile) ethers of synthesizing glycol includes:
First device is passed through acrylonitrile；
Second device is passed through the mixture of basic catalyst and ethylene glycol, the molar ratio control of acrylonitrile and ethylene glycol (2.4~
2.5): 1；
Acrylonitrile, basic catalyst and the ethylene glycol hybrid reaction in reaction channel control reaction temperature by temperature control device and exist
120 DEG C~150 DEG C, the reaction time is 3~4min；
Product pH is modulated 4~5, extracts away moisture, excessive propene nitrile is removed and obtains bis- (propionitrile) ethers of ethylene glycol,
Basic catalyst is potassium tert-butoxide.
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| CN201710118057.5A CN106905189B (en) | 2017-03-01 | 2017-03-01 | Microreactor system and method for bis- (propionitrile) the ether synthesis of ethylene glycol |
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| CN107522638A (en) * | 2017-10-17 | 2017-12-29 | 苏州汶颢微流控技术股份有限公司 | Prepare the microreactor and method of o-methyl formate benzene sulfonamide |
| CN108164411B (en) * | 2017-12-29 | 2021-03-02 | 苏州汶颢微流控技术股份有限公司 | Method for preparing p-heptyloxybenzoic acid based on microreactor |
Citations (5)
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|---|---|---|---|---|
| US4168602A (en) * | 1975-03-11 | 1979-09-25 | Sun Ventures, Inc. | Block copolymer of poly (dioxaarylamide) and polyamide and fibers and fibrous material produced therefrom |
| US4271089A (en) * | 1978-06-16 | 1981-06-02 | Suntech, Inc. | Cyanoalkylation process |
| WO2009085072A1 (en) * | 2007-12-31 | 2009-07-09 | Ekc Technology, Inc | Composition comprising chelating agents containing amidoxime compounds |
| CN103055980A (en) * | 2012-12-31 | 2013-04-24 | 苏州汶颢芯片科技有限公司 | Micro-fluidic reaction chip based on micro/nano structure and preparation method thereof |
| CN106146344A (en) * | 2016-07-26 | 2016-11-23 | 张家港瀚康化工有限公司 | The preparation method of ethylene glycol bis (propionitrile) ether |
-
2017
- 2017-03-01 CN CN201710118057.5A patent/CN106905189B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4168602A (en) * | 1975-03-11 | 1979-09-25 | Sun Ventures, Inc. | Block copolymer of poly (dioxaarylamide) and polyamide and fibers and fibrous material produced therefrom |
| US4271089A (en) * | 1978-06-16 | 1981-06-02 | Suntech, Inc. | Cyanoalkylation process |
| WO2009085072A1 (en) * | 2007-12-31 | 2009-07-09 | Ekc Technology, Inc | Composition comprising chelating agents containing amidoxime compounds |
| CN103055980A (en) * | 2012-12-31 | 2013-04-24 | 苏州汶颢芯片科技有限公司 | Micro-fluidic reaction chip based on micro/nano structure and preparation method thereof |
| CN106146344A (en) * | 2016-07-26 | 2016-11-23 | 张家港瀚康化工有限公司 | The preparation method of ethylene glycol bis (propionitrile) ether |
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