CN109896996A - Organic carboxyl acid is continuously synthesizing to method - Google Patents
Organic carboxyl acid is continuously synthesizing to method Download PDFInfo
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Abstract
Method is continuously synthesizing to the present invention provides a kind of organic carboxyl acid.It includes: that catalyst, halide, CO and organic solvent are continuously passed through at least one continuous coil pipe reaction unit to carry out continuously slotting carbonyl reaction that this, which is continuously synthesizing to method, obtain organic carboxyl acid, and organic carboxyl acid is continuously discharged, wherein halide is selected from aryl halide or alkenyl halide, and controls the pressure in continuous coil pipe reaction unit by counterbalance valve.Continuous coil pipe reaction unit can be realized to the purpose for being continuously synthesizing to organic carboxyl acid as the reacting environment for inserting carbonyl reaction.Controlling the pressure in continuous coil pipe reaction unit by counterbalance valve can be improved CO solubility in continuous coil pipe reaction unit, to be conducive to improve the contact area of gas-liquid two-phase reaction raw materials, ensure enough gas-liquid mass transfer rates, reduce influence of the gas-liquid mass transfer rate to reaction rate, to be conducive to improve the rate and product yield of reaction, and shorten residence time of the reaction raw materials in reaction coil pipe.
Description
Technical field
The present invention relates to slotting carbonyls to react field, is continuously synthesizing to method in particular to a kind of organic carboxyl acid.
Background technique
In organic synthesis, the slotting carbonyl reaction of palladium chtalyst is a kind of particularly useful reaction, it provides a kind of formation carbon-
The unique method of carbon key.It is synthesizing carbonyl compound that the palladium chtalyst of aryl and alkenyl halide in a mild condition, which inserts carbonyl reaction,
Highly useful synthetic method.Reaction mechanism be aryl and alkenyl halide first and Pd occur oxidative addition generate aryl and
Alkenyl palladium complex, then CO is inserted between palladium carbon key, finally under the nucleophilic attack of the reagents such as alcohol or water, is formed phase
The ester or carboxylic acid answered.Fragrance or the unsaturated carboxylic acid of α, β-and ester be exactly aryl or alkenyl halide in water or alcohol by inserting
Made from carbonyl reaction.
This kind of slotting carbonyl reaction is usually gas-liquid two-phase reaction.High temperature and pressure is usually required when reaction.Such as 3,3,3- tri- is fluoro-
2- bromopropene synthesizes in the reaction of trifluoromethyl uracil, and reaction condition is in PdCl2(Ph3P)2Under catalysis, made of triethylamine
Alkali, at 100 DEG C, CO is forced into 40atm reaction.For another example 5- bromo thiazole carbon monoxide inserts carbonyl and prepares thiazole -5- Ethyl formate
Reaction, in PdCl2(PhP)2Under catalysis, triethylamine does alkali, and CO is forced into 7atm and completes reaction.
The technical solution for completing such gas-liquid two-phase heterogeneous reaction is more, mainly includes following several:
1. conventional batch production technology, the usually used reactor of this kind of production technology is autoclave reactor.
The shortcomings that autoclave reactor are as follows: land occupation is larger.Reaction under high pressure is higher to the security requirement of equipment material, because
Also more common normal pressure reactor is costly for the cost of investment of this autoclave reactor.For pharmaceutical manufacturer, particular device
Investment, is very challenging, because 1) the decision needs of investment are made before production goes through；2) equipment investment scheme
It can not determine, this just makes enterprise investment autoclave this kind of expensive, and risk when applicable reaction type limited equipment
It is multiplied.
2. a kind of alternative alternative solution is using continuous reaction process strategy.Common continuous gas-liquid two-phase reaction
Device includes: tower reactor (bubble tower, plate column, packed tower etc.).The shortcomings that tower reactor is, land occupation big with volume
Greatly, equipment investment is high, the disadvantage of safety difference.Such reactor is more applicable for big chemical company.For pharmaceutical manufacturer, relate to
And reaction type it is more, it is more flexible changeable.This particular reactor, dangerous are invested on a large scale.
In addition there are also some continuous gas-liquid reactors with specific structure.Existing literature provides a kind of multicell series connection company
Continuous gas-liquid reactor, this reactor increase the flow path length of fluid, to increase gas-liquid in fixed space size
Time of contact.But this reactor resistance to pressure is poor, is not suitable for reaction under high pressure.And its disclosed application example is mostly reaction speed
The cracking inorganic reaction of rate, the organic reaction slower for reaction rate are then unsuitable.Another existing literature reports one
The semi-transparent membrane reactor of kind, in this reactor, gas walks a survey of film, and liquid walks another survey of film, by pressurization, makes gas
It is contacted through film with liquid and participates in the reaction in liquid phase.This usual structure of reactor is more complex, and difficulty of processing is larger, price
Valuableness, and the use of film needs certain temperature range, is accordingly difficult to amplify.Above-mentioned continuous semi-transparent membrane reactor above-mentioned has
The shortcomings that gas-liquid reactor of specific internal is that structure is complicated, is not easy to amplify.
Summary of the invention
It is continuously synthesizing to method the main purpose of the present invention is to provide a kind of organic carboxyl acid, to solve existing slotting carbonyl
React the existing reaction unit problem that structure is complicated, at high cost and low product yield.
To achieve the goals above, it is according to the present invention provide a kind of organic carboxyl acid be continuously synthesizing to method, the company
The continuous method that is combined to includes: that catalyst, halide, CO and organic solvent are continuously passed through at least one continuous coil pipe reaction dress
Middle progress continuously slotting carbonyl reaction is set, obtains organic carboxyl acid, and organic carboxyl acid is continuously discharged, wherein halide is selected from aryl halogenation
Object or alkenyl halide, and the pressure in continuous coil pipe reaction unit is controlled by counterbalance valve.
Further, continuously the reaction temperature of slotting carbonyl reaction is 15~150 DEG C, and reaction pressure is 0.1~2MPa.
Further, continuously the reaction temperature of slotting carbonyl reaction is 80~120 DEG C, and reaction pressure is 0.8~1.5MPa.
Further, continuously residence time of the reaction mass in slotting carbonyl reaction in continuous coil pipe reaction unit is 5min
~5h.
Further, continuously residence time of the reaction mass in slotting carbonyl reaction in continuous coil pipe reaction unit is
30min~2h.
Further, before carrying out continuously slotting carbonyl reaction, it is continuously synthesizing to method further include: make catalyst, halide
And organic solvent mixing, form mixed liquor；Mixed liquor is continuously delivered in continuous coil pipe reaction unit using plunger pump.
Further, it is continuously synthesizing to method further include: organic base is added in the continuous reaction system for inserting carbonyl reaction, has
Machine alkali is selected from triethylamine, N, one of group that N- diisopropylethylamine and N- methylmorphine woods form or a variety of.
Further, the internal diameter of continuous coil pipe reaction unit is 2~15mm.
Further, it is continuously synthesizing to method further include: using the dosage of gas flowmeter control CO.
Further, the mole ratio of halide and CO are 1:(1~50).
It applies the technical scheme of the present invention, can be realized continuous coil pipe reaction unit as the reacting environment for inserting carbonyl reaction
It is continuously synthesizing to the purpose of organic carboxyl acid.Controlling the pressure in continuous coil pipe reaction unit by counterbalance valve can be improved continuous disk
CO solubility in tube reaction device, to be conducive to improve the contact area of gas-liquid two-phase reaction raw materials, it is ensured that enough gas-liquids
Mass transfer rate reduces influence of the gas-liquid mass transfer rate to reaction rate, thus be conducive to improve the rate and product yield of reaction,
And shorten residence time of the reaction raw materials in reaction coil pipe.The reaction unit that above-mentioned successive reaction synthetic method uses also has
The advantages that structure is simple, easily designed processing, easy to clean, convenient for safeguarding and at low cost.
Detailed description of the invention
The accompanying drawings constituting a part of this application is used to provide further understanding of the present invention, and of the invention shows
Examples and descriptions thereof are used to explain the present invention for meaning property, does not constitute improper limitations of the present invention.In the accompanying drawings:
What Fig. 1 showed the organic carboxyl acid provided according to a preferred embodiment of the present invention is continuously synthesizing to method
Used in organic carboxyl acid continuous coil pipe reaction unit structural schematic diagram.
Wherein, the above drawings include the following reference numerals:
10, automatic control system；20, carbon monoxide feeding mechanism；21, gas flowmeter；30, material solution storage tank；31,
Dnockout pumps；40, it is continuously synthesizing to unit；41, temperature control collet；42, continuous coil pipe reaction unit；43, first pressure gauge；44,
Two pressure gauges；45, thermometer；46, third pressure gauge；47, counterbalance valve；48, relief valve；50, reception device.
Specific embodiment
It should be noted that in the absence of conflict, the features in the embodiments and the embodiments of the present application can phase
Mutually combination.Below in conjunction with embodiment, the present invention will be described in detail.
As described in background technique, existing slotting carbonyl reacts existing reaction unit, and structure is complicated, it is at high cost with
And the problem that product yield is low.In order to solve the above-mentioned technical problem, it is continuously synthesizing to this application provides a kind of organic carboxyl acid
Method, it includes: that catalyst, halide, CO and organic solvent are continuously passed through at least one continuously that this, which is continuously synthesizing to method,
Continuously slotting carbonyl reaction is carried out in coil pipe reaction unit, obtains organic carboxyl acid, and organic carboxyl acid is continuously discharged, wherein halide selects
The pressure in continuous coil pipe reaction unit is controlled from aryl halide or alkenyl halide, and by counterbalance valve.
Continuous coil pipe reaction unit can be realized as the reacting environment for inserting carbonyl reaction and be continuously synthesizing to organic carboxyl acid
Purpose.Controlling the pressure in continuous coil pipe reaction unit by counterbalance valve can be improved CO dissolution in continuous coil pipe reaction unit
Degree, to be conducive to improve the contact area of gas-liquid two-phase reaction raw materials, it is ensured that enough gas-liquid mass transfer rates reduce gas-liquid and pass
Influence of the matter rate to reaction rate to be conducive to improve the rate and product yield of reaction, and shortens reaction raw materials anti-
Answer the residence time in coil pipe.The reaction unit that above-mentioned successive reaction synthetic method uses also has structure simple, easily designed
Processing, it is easy to clean, convenient for safeguarding and at low cost the advantages that.
It should be noted that continuous coil pipe reaction unit carries out when the quantity of continuous coil pipe reaction unit is more than or equal to 2
It is arranged in series, this is conducive to the rank for improving joint capacity.
Above-mentioned continuous coil pipe reaction unit can be the reaction unit using continuous coil pipe as reacting environment.
It carries out inserting carbonyl reaction synthesis organic carboxyl acid using the above method, is conducive to the reaction rate and production that improve organic carboxyl acid
Rate.In a kind of preferred embodiment, the reaction temperature of continuous slotting carbonyl reaction is 15~150 DEG C, reaction pressure is 0.1~
2MPa.The reaction temperature that carbonyl reaction is inserted in serialization includes but is not limited to above range, and is limited advantageous within the above range
It is carried out in making to react to the direction for being conducive to synthesize organic carboxyl acid, and then is conducive to the yield of raising organic carboxyl acid.In order into one
Step improves the yield of organic carboxyl acid, it is highly preferred that the reaction temperature of above-mentioned continuous slotting carbonyl reaction is 80~120 DEG C, reaction pressure
For 0.8~1.5MPa.
In order to improve counterbalance valve to pressure controlled accuracy in serialization coil pipe reaction unit, the above-mentioned side of being continuously synthesizing to
Method further includes monitoring the pressure of the arrival end of continuous coil pipe reaction unit using first pressure gauge, being monitored using second pressure gauge
Pressure in continuous coil pipe reaction unit, the pressure of the outlet end of continuous coil pipe reaction unit is monitored using third pressure gauge.It is logical
The pressure of the arrival end and outlet end and inside of crossing the continuous coil pipe reaction unit of real-time monitoring is conducive in time carry out pressure
Adjustment, to be conducive to improve the reaction rate of synthesis technology.
In a kind of preferred embodiment, the reaction mass in continuous slotting carbonyl reaction stops in continuous coil pipe reaction unit
Staying the time is 5min~5h.The range of residence time includes but is not limited to above range, and limited has within the above range
Conducive to further increasing the extent of reaction of reaction raw materials, and then be conducive to improve the yield of organic carboxyl acid.It is highly preferred that continuous insert
Residence time of the reaction mass in continuous coil pipe reaction unit in carbonyl reaction is 30min~2h.
Preferably, the above-mentioned method that is continuously synthesizing to includes: using temperature control collet to the temperature in continuous coil pipe reaction unit
It is controlled.
Above-mentioned reaction raw materials (catalyst, halide and organic solvent) can be delivered to continuous coil pipe reaction unit respectively
In, mixed liquor is delivered in continuous coil pipe reaction unit after can also mixing.In a kind of preferred embodiment, connected
It is above-mentioned to be continuously synthesizing to method before continuous slotting carbonyl reaction further include: to make catalyst, halide and organic solvent mixing, formed mixed
Close liquid；Mixed liquor is continuously delivered in continuous coil pipe reaction unit using plunger pump.
Before carrying out serialization and inserting carbonyl reaction, it is anti-that above-mentioned raw materials mixed liquor is first delivered to continuous coil pipe using plunger pump
It answers in device, this can make to form plug flow in reaction system.This is conducive to inhibit the back-mixing in reaction process, makes the production generated
Object is discharged in time, while can also effectively avoid the generation of side reaction.Simultaneously compared to existing slotting carbonyl reaction method, use is above-mentioned
Flow technique can make heat exchanging process more efficient, reduce the temperature gradient of reaction system, to further decrease side reaction
Probability of happening.
In a kind of preferred embodiment, it is continuously synthesizing to method further include: in the continuous reaction system for inserting carbonyl reaction
Be added organic base, organic base include but is not limited to triethylamine, n,N-diisopropylethylamine and N- methylmorphine woods at group in
It is one or more.
The catalytic activity that organic base is conducive to improve catalyst is added in the continuous reaction system for inserting carbonyl reaction, to mention
The reaction rate of the slotting carbonyl reaction of height.
According to the rank of reaction, the reaction coil pipe of different capabilities can choose.Preferably, continuous coil pipe reaction unit is interior
Diameter is 2~15mm.The internal diameter for reacting coil pipe restriction is conducive to further increase within the above range continuously slotting carbonyl reaction process
In heat exchange efficiency and gas liquid interfacial area improve the yield of organic carboxyl acid to advantageously reduce the generation of side reaction.Equally
In the case where volume, it is preferable that the internal diameter of continuous coil pipe reaction unit is 2~8mm.The internal diameter of continuous coil pipe reaction unit is smaller
In the case where, the material-heat-exchanging in reactor is more efficient, and gas liquid interfacial area is bigger, to be conducive to improve organic carboxyl acid
Yield and reaction rate.
On the other hand the application additionally provides a kind of continuous coil pipe reaction unit of organic carboxyl acid, as shown in Figure 1.Using upper
The step of stating the continuous coil pipe reaction unit synthesis organic carboxyl acid of organic carboxyl acid is as follows: under the control of automatic control system 10,
CO is passed through the continuous coil pipe for being continuously synthesizing to unit 40 by exporting in carbon monoxide feeding mechanism 20 after gas flowmeter 21
In reaction unit 42 (continuous reaction coil pipe), while being arranged around continuous coil pipe reaction unit 42 (continuous reaction coil pipe)
Have in temperature control collet 41.Simultaneously under the control of automatic control system 10, the mixed liquor of catalyst, halide and organic solvent by
Material solution storage tank 30 exports, and then under the action of dnockout pumps 31, is delivered to continuous 42 (continuous reaction of coil pipe reaction unit
Coil pipe) in.After reaction, reaction mass is delivered in reception device 50.Wherein, in CO and catalyst, halide and organic
The mixed liquor of solvent enters before continuous coil pipe reaction unit 42 (continuous reaction coil pipe), is tested and is connected using first pressure gauge 43
Entrance pressure (the P of continuous coil pipe reaction unit 42 (continuous reaction coil pipe)1)；Continuous coil pipe reaction is tested using second pressure gauge 44
Internal pressure (the P of device 42 (continuous reaction coil pipe)2), while continuous coil pipe reaction unit 42 is tested using thermometer 45
(continuous reaction coil pipe) internal temperature；Continuous 42 (continuous reaction of coil pipe reaction unit is tested using third pressure gauge 46
Coil pipe) outlet end pressure (P3).Showing according to first pressure gauge 43, second pressure gauge 44 and third pressure gauge 46 simultaneously
Number, adjusts the pressure in continuous coil pipe reaction unit 42 (continuous reaction coil pipe) by counterbalance valve 47.When continuous coil pipe reacts
When device 42 (continuous reaction coil pipe) blocks, system pressure is released by relief valve 48, it is ensured that process safety.
The application is described in further detail below in conjunction with specific embodiment, these embodiments should not be understood as limitation originally
Apply for range claimed.
Embodiment 1 to 4
It is reacted as follows using device shown in FIG. 1:
Technological parameter is shown in Table 1.
Comparative example 1 to 2
With the difference of embodiment 1 are as follows: insert carbonyl reaction and carry out in a high pressure reaction kettle, synthesize organic carboxyl acid with batch processes.
Technological parameter is shown in Table 1.
Table 1
Note: " eq. " refers to the multiple of the amount of the substance relative to halide in table.
Embodiment 5
With the difference of embodiment 1 are as follows: residence time of the raw material in continuous coil pipe reaction unit is 20min.
After reaction, the yield of organic carboxyl acid is 50%.
Embodiment 6
With the difference of embodiment 1 are as follows: the internal diameter of continuous coil pipe reaction unit is 15mm.
After reaction, the yield of organic carboxyl acid is 70%.
Comparative example 3
With the difference of embodiment 1 are as follows: be not provided with counterbalance valve.
After reaction, the yield of organic carboxyl acid is 29%.
It can be seen from the above description that the above embodiments of the present invention realized the following chievements:
Comparing embodiment 1 to 6 and comparative example 1 to 3 using the method provided by the present application that is continuously synthesizing to it is found that be conducive to mention
The yield of high organic carboxyl acid.
Comparing embodiment 1 to 4 it is found that the reaction temperature and reaction pressure that reaction will be continuously synthesizing to be limited to the application excellent
Be conducive to improve the yield of organic carboxyl acid in the range of choosing.
Comparing embodiment 1 and comparative example 3 are it is found that the counterbalance valve that setting can control pressure in continuous coil pipe reaction unit has
Conducive to the yield for improving organic carboxyl acid.
Comparing embodiment 1 and embodiment 5 and 6 are it is found that by residence time of the raw material in continuous coil pipe reaction unit and interior
Diameter is limited to the yield for being conducive to improve organic carboxyl acid in the preferred range of the application.
The foregoing is only a preferred embodiment of the present invention, is not intended to restrict the invention, for the skill of this field
For art personnel, the invention may be variously modified and varied.All within the spirits and principles of the present invention, made any to repair
Change, equivalent replacement, improvement etc., should all be included in the protection scope of the present invention.
Claims (10)
1. a kind of organic carboxyl acid is continuously synthesizing to method, which is characterized in that the method that is continuously synthesizing to includes:
Catalyst, halide, CO and organic solvent are continuously passed through at least one continuous coil pipe reaction unit and carried out continuously
Insert carbonyl reaction, obtain organic carboxyl acid, and the organic carboxyl acid is continuously discharged, wherein the halide be selected from aryl halide or
Alkenyl halide, and the pressure in the continuous coil pipe reaction unit is controlled by counterbalance valve.
2. according to claim 1 be continuously synthesizing to method, which is characterized in that the reaction temperature of the continuous slotting carbonyl reaction
It is 15~150 DEG C, reaction pressure is 0.1~2MPa.
3. according to claim 2 be continuously synthesizing to method, which is characterized in that the reaction temperature of the continuous slotting carbonyl reaction
It is 80~120 DEG C, reaction pressure is 0.8~1.5MPa.
4. according to any one of claim 1 to 3 be continuously synthesizing to method, which is characterized in that the continuously slotting carbonyl is anti-
Residence time of the reaction mass answered in the continuous coil pipe reaction unit is 5min~5h.
5. according to claim 4 be continuously synthesizing to method, which is characterized in that the reactant in the continuous slotting carbonyl reaction
Expect that the residence time in the continuous coil pipe reaction unit is 30min~2h.
6. according to any one of claim 1 to 5 be continuously synthesizing to method, which is characterized in that described continuous in progress
It is described to be continuously synthesizing to method before inserting carbonyl reaction further include:
Make the catalyst, the halide and organic solvent mixing, forms mixed liquor；
The mixed liquor is continuously delivered in the continuous coil pipe reaction unit using plunger pump.
7. according to any one of claim 1 to 5 be continuously synthesizing to method, which is characterized in that described to be continuously synthesizing to
Method further include: organic base is added in the reaction system of the continuous slotting carbonyl reaction, the organic base is selected from triethylamine, N, N-
One of group of diisopropylethylamine and N- methylmorphine woods composition is a variety of.
8. according to claim 1 be continuously synthesizing to method, which is characterized in that the internal diameter of the continuous coil pipe reaction unit
For 2~15mm.
9. according to any one of claim 1 to 8 be continuously synthesizing to method, which is characterized in that described to be continuously synthesizing to
Method further include: the dosage of the CO is controlled using gas flowmeter.
10. according to claim 1 be continuously synthesizing to method, which is characterized in that mole of the halide and the CO
Amount is than being 1:(1~50).
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112225754A (en) * | 2020-12-16 | 2021-01-15 | 杭州景业智能科技股份有限公司 | Pipelining continuous preparation method and preparation device of triisopentyl phosphate for spent fuel aftertreatment |
| CN113548956A (en) * | 2021-07-30 | 2021-10-26 | 四川信乙化工有限公司 | Continuous production system of phenylacetic acid |
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| CN112225754A (en) * | 2020-12-16 | 2021-01-15 | 杭州景业智能科技股份有限公司 | Pipelining continuous preparation method and preparation device of triisopentyl phosphate for spent fuel aftertreatment |
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| CN113548956A (en) * | 2021-07-30 | 2021-10-26 | 四川信乙化工有限公司 | Continuous production system of phenylacetic acid |
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Application publication date: 20190618 |