CN110590556A - Preparation method of fluorine-containing asymmetric chain carbonate - Google Patents
Preparation method of fluorine-containing asymmetric chain carbonate Download PDFInfo
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- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
Abstract
The invention provides a preparation method of fluorine-containing asymmetric chain carbonate, which comprises the following steps: a) weighing and batching fluorine-containing monohydric alcohol, halogenated carbonate and an acid-binding agent according to a certain molar ratio, or dissolving the three raw materials in a solvent according to a certain molar ratio in advance to prepare a solution; b) introducing the three raw materials or a solution prepared from the three raw materials into a mixing module of a continuous flow reactor according to a specific feeding mode for premixing to obtain a reaction raw material mixture; c) reacting the reaction raw material mixture obtained in the step b) in a reaction module of a continuous microchannel reactor to obtain a fluorine-containing asymmetric chain carbonate crude product, and performing post-treatment to obtain a finished product. Compared with the prior art, the preparation method provided by the invention has the advantages of simple process, low cost, safety, environmental protection, continuous production, higher raw material conversion rate and product selectivity, capability of greatly relieving the pressure of the existing preparation method on the aspects of environmental protection and capacity, and very good industrial application prospect.
Description
Technical Field
The invention relates to the technical field of chemical synthesis, in particular to a preparation method of fluorine-containing asymmetric chain carbonate.
Background
The preparation method of the common fluorine-containing asymmetric chain carbonate mainly comprises the following steps: (1) reacting fluorine-containing monohydric alcohol with halogenated carbonate; (2) mixing fluorine-containing monohydric alcohol and saturated straight-chain monohydric alcohol with triphosgene, and reacting in the presence of organic amine; (3) carrying out transesterification reaction on fluorine-containing monohydric alcohol and straight-chain carbonate under the condition of a catalyst; the above reactions are all carried out in a kettle type production equipment.
However, the above production method has the following problems: on one hand, the halogenated carbonate used in the method (1) and the triphosgene used in the method (2) belong to highly toxic products, and kettle type reaction equipment used in batch production inevitably causes certain harm to operators and the environment; on the other hand, the traditional kettle type reaction process needs a large amount of organic solvent, so that environmental pollution and potential safety production hazards are caused, and the capacity of the existing kettle type production equipment is limited; therefore, the preparation method of the fluorine-containing asymmetric carbonate has double pressure in the aspects of environmental protection and capacity.
Disclosure of Invention
In view of the above, the invention aims to provide a preparation method of fluorine-containing asymmetric chain carbonate, and the preparation method provided by the invention has the advantages of simple process, low cost, environmental protection, continuous production, higher raw material conversion rate and product selectivity, capability of greatly relieving the pressure of the existing preparation method in the aspects of safety, environmental protection and productivity, and good industrial application prospect.
The invention provides a preparation method of fluorine-containing asymmetric chain carbonate, which comprises the following steps:
a) weighing fluorine-containing monohydric alcohol, halogenated carbonate and an acid-binding agent according to a certain molar ratio, preparing materials or dissolving the three raw materials in a solvent according to a certain molar ratio to prepare a solution;
b) introducing the three raw materials or a solution prepared from the three raw materials into a mixing module of a continuous flow reactor according to a specific feeding mode for premixing to obtain a reaction raw material mixture;
c) introducing the reaction raw material mixture obtained in the step b) into a reaction module of a continuous microchannel reactor for reaction to obtain a crude product of the fluorine-containing asymmetric chain carbonate, and performing post-treatment to obtain a finished product.
Preferably, the fluorine-containing monohydric alcohol in step a) has a general formula shown in formula (I):
R1OH is formula (I);
in the formula (I), R1Is selected from-CF3、-CF2H、-CFH2、-CH2CF3、-CH2CF2H、-CH2CFH2、-CF2CF3、-CF2CF2H、-CF2CFH2、-CFHCF3、-CFHCF2H、-CFHCFH2、-CH(CF3)2、-CH2C2F5、-CH2CF2CF3、-CH2CF2CF2H、-CF2CF2CF3or-CF2CFHCF2CH2。
Preferably, the halogenated carbonate in step a) has the general formula shown in formula (II):
XCOOR2formula (II);
in the formula (II), X is selected from-F, -Cl, -Br or-I, R2Is selected from-CF2CH3、-CH2C2F5or-CH3、-C2H5。
Preferably, the acid-binding agent in step a) is at least one selected from triethylamine, pyridine, imidazole, potassium carbonate, potassium bicarbonate, sodium carbonate, sodium bicarbonate, potassium hydroxide and sodium hydroxide; the solvent is at least one selected from water, tetrahydrofuran, dichloromethane, 1, 4-dioxane, acetone and ethyl acetate.
Preferably, the molar ratio of the fluorine-containing monohydric alcohol to the halogenated carbonate to the acid-binding agent in the step a) is (0.5-1.8): 1: (0 to 1.8).
Preferably, the feeding mode in the step b) is pumping; the pumping can be that three raw materials are divided into three parts to be fed simultaneously, or any two raw materials are premixed and then divided into two parts with the rest raw material to be fed simultaneously; the pumping flow rate is 2g/min to 5000 g/min.
Preferably, the continuous flow reactor in steps b) and c) is such that a continuous reverse reaction can be achievedThe corresponding microchannel reactor comprises a premixing module, a reaction module and a post-treatment module. Such as CorningLab Reactor or Corning CoA G1-hybrid reaction device and a series of reaction devices with larger flux.
Preferably, the pressure of the continuous microchannel in the step c) is 0 bar-10 bar, the temperature is 0-130 ℃, and the time is 5 s-180 s.
Preferably, the post-treatment in the step c) comprises cooling, layering after cooling or washing, purification and the like after cooling.
Compared with the prior art, the method for preparing the fluorine-containing asymmetric chain carbonate through the continuous flow reaction has the advantages of simple process, low cost, safety, environmental protection, continuous production, higher raw material conversion rate and product selectivity, capability of greatly relieving the pressure of the conventional preparation method in the aspects of safety, environmental protection and capacity, and good industrial application prospect. Experimental results show that the raw material conversion rate of the preparation method provided by the invention is not lower than 99.8%, and the product selectivity is not lower than 99.5%.
In addition, compared with the traditional kettle type reaction device, the preparation method provided by the invention has the advantages of short reaction time, small equipment volume and investment, environmental protection, safety and the like during the production, so that the preparation method has great advantages compared with the prior art.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments of the present invention, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides a preparation method of fluorine-containing asymmetric chain carbonate, which comprises the following steps:
a) weighing fluorine-containing monohydric alcohol, halogenated carbonate and an acid-binding agent according to a certain molar ratio, preparing materials or dissolving the three raw materials in a solvent according to a certain molar ratio to prepare a solution;
b) introducing the three raw materials or a solution prepared from the three raw materials into a mixing module of a continuous flow reactor according to a specific feeding mode for premixing to obtain a reaction raw material mixture;
c) introducing the reaction raw material mixture obtained in the step b) into a reaction module of a continuous microchannel reactor for reaction to obtain a crude product of the fluorine-containing asymmetric chain carbonate, and performing post-treatment to obtain a finished product.
In the present invention, the fluorine-containing monohydric alcohol preferably has a general formula represented by formula (I):
R1OH is formula (I);
in the formula (I), R1Preferably selected from-CF3、-CF2H、-CFH2、-CH2CF3、-CH2CF2H、-CH2CFH2、-CF2CF3、-CF2CF2H、-CF2CFH2、-CFHCF3、-CFHCF2H、-CFHCFH2、-CH(CF3)2、-CH2C2F5、-CH2CF2CF3、-CH2CF2CF2H、-CF2CF2CF3or-CF2CFHCF2CH2More preferably-CH2CF3or-CF2CF3. In a preferred embodiment of the invention, the fluorine-containing monohydric alcohol is 3,3, 3-trifluoro-1-propanol.
In the present invention, the halogenated carbonate preferably has a general formula represented by formula (II):
XCOOR2formula (II);
in formula (II), X is preferably selected from-F, -Cl, -Br or-I, more preferably-F or-Cl, and most preferably-Cl; r2Preferably selected from-CF2CH3、-CH2C2F5or-CH3、-C2H5. In a preferred embodiment of the invention, the halogenated carbonate is tert-butyl chloroformate.
In the present invention, the molar ratio of the fluorine-containing monohydric alcohol to the halogenated carbonate is preferably (0.5 to 1.8): 1, more preferably (0.8 to 1.5): 1, most preferably (0.9 to 1.2): 1.
in the present invention, the acid-binding agent is preferably selected from at least one of triethylamine, pyridine, imidazole, potassium carbonate, potassium bicarbonate, sodium carbonate, sodium bicarbonate, potassium hydroxide, and sodium hydroxide, more preferably at least one of triethylamine, potassium carbonate, and potassium hydroxide, and most preferably potassium hydroxide; the source of the acid-binding agent is not particularly limited in the present invention, and commercially available products of the organic bases such as triethylamine, pyridine and imidazole, potassium carbonate, potassium bicarbonate, sodium carbonate, sodium bicarbonate, potassium hydroxide and sodium hydroxide, which are well known to those skilled in the art, may be used.
In the invention, the mole ratio of the acid-binding agent, the fluorine-containing monohydric alcohol and the halogenated carbonate is preferably (0-1.8): (0.5-1.8): 1, more preferably (0.9 to 1.2): (0.9-1.2): 1; wherein when the mole ratio of the acid-binding agent to the fluorine-containing monohydric alcohol to the halogenated carbonate is 0: (0.5-1.8): 1, no acid-binding agent is needed; therefore, compared with the traditional kettle type production process, the fluorine-containing asymmetric carbonate production process provided by the invention can directly mix the fluorine-containing monohydric alcohol and the halogenated carbonate without an acid-binding agent or a solvent, and then strengthen the reaction conditions by increasing the reaction temperature, the reaction pressure and the like, so that the reaction has certain raw material conversion rate and reaction selectivity.
In the present invention, the solvent is preferably at least one selected from the group consisting of water, tetrahydrofuran, dichloromethane, 1, 4-dioxane, acetone and ethyl acetate, more preferably at least one selected from the group consisting of water, dichloromethane and acetone, and most preferably water. In addition, the solution of the present invention only needs to be flowable in the continuous flow reactor, and the concentration of the solution is not limited.
In the present invention, the specific feeding manner is pumping; the pumping can be that three raw materials are divided into three parts to be fed simultaneously, or any two raw materials are premixed and then divided into two parts with the rest raw material to be fed simultaneously; the pumping flow rate can be 2g/min to 5000 g/min; the flow rate is determined by the reaction process conditions and the flux of different models of continuous flow reaction devices, and the flow rate can be controlled by a metering pump.
In the present invention, the continuous flow reactor is a microchannel reactor capable of realizing continuous reaction, and comprises a premixing module, a reaction module and a post-treatment module, preferably selected from CorningLab Reactor or Corning CoA G1-hybrid reaction device and a series of reaction devices with larger flux. . In the invention, the micro-channel continuous flow reactor has the characteristics of large specific surface area, high transfer rate, short contact time, few byproducts, very strong heat transfer and mass transfer capacities, high speed, direct amplification, high safety, good operability and the like; the continuous flow reactor is a parallel system with a module structure and comprises a mixer, a micro-channel reactor, a liquid-liquid separation module, a continuous rectification module and the like which are connected through connecting pipes; the microchannel reactor can be made of glass, metal, silicon carbide, functional plastics and the like; the mixer is connected with the liquid feeding hole, and a liquid preheating plate is arranged between the liquid feeding hole and the mixer; the continuous flow reactor has good portability, can realize dispersed construction in the product use place and on-site production and supply, really realizes the portability of a chemical plant, can increase and decrease the number of channels according to the market condition and replace modules to pull and adjust the production, and has high operation flexibility.
The specific mixing process is not particularly limited, and the fluorine-containing monohydric alcohol, the halogenated carbonate and the acid-binding agent solution can be simultaneously pumped into a mixer of the continuous flow reactor according to certain flow rates; or the fluorine-containing monohydric alcohol and the halogenated carbonate are mixed in advance, and then the mixed solution and the acid-binding agent solution are pumped into a mixer of the continuous flow reactor simultaneously according to certain flow rates; or after the fluorine-containing monohydric alcohol and the acid binding agent solution are mixed in advance, the mixed solution and the halogenated carbonate are pumped into a mixer of the continuous flow reactor simultaneously according to certain flow rates.
The reaction raw materials are premixed and then enter a reaction module of a continuous microchannel reactor for reaction to obtain the fluorine-containing asymmetric chain carbonate. In the present invention, the reaction formula of the reaction is as follows:
in the invention, the pressure of the continuous microchannel reaction is preferably 0bar to 10bar, and more preferably 1bar to 9 bar; the temperature of the continuous microchannel reaction is preferably 0-130 ℃, more preferably 40-100 ℃, and most preferably 60 ℃; the time for the continuous microchannel reaction is preferably 5s to 180s, more preferably 30s to 80s, and most preferably 60 s.
The post-treatment of the invention preferably comprises cooling, layering after cooling or washing, purification and the like after cooling.
The method for preparing the fluorine-containing asymmetric chain carbonate through the continuous flow reaction has the advantages of simple process, low cost, safety, environmental protection, continuous production, higher raw material conversion rate and product selectivity, capability of greatly relieving the pressure of the conventional preparation method on safety, environmental protection and capacity and very good industrial application prospect. In addition, the preparation method provided by the invention adopts the continuous flow reactor, and has the advantages of short reaction time, small equipment volume and investment, environmental protection, safety and the like when being compared with the traditional kettle type reaction device in production, so that the preparation method has great advantages compared with the prior art.
The invention provides a preparation method of fluorine-containing asymmetric chain carbonate, which comprises the following steps: a) weighing fluorine-containing monohydric alcohol, halogenated carbonate and an acid-binding agent according to a certain molar ratio, preparing materials or dissolving the three raw materials in a solvent according to a certain molar ratio to prepare a solution; b) introducing the three raw materials or a solution prepared from the three raw materials into a mixing module of a continuous flow reactor according to a specific feeding mode for premixing to obtain a reaction raw material mixture; c) introducing the reaction raw material mixture obtained in the step b) into a reaction module of a continuous microchannel reactor for reaction to obtain a crude product of the fluorine-containing asymmetric chain carbonate, and performing post-treatment to obtain a finished product. Compared with the prior art, the method for preparing the fluorine-containing asymmetric chain carbonate by the continuous flow reaction has the advantages of simple process, low cost, safety, environmental protection, continuous production and the like, has higher raw material conversion rate and product selectivity, can greatly relieve the pressure of the conventional preparation method in the aspects of safety, environmental protection and productivity, and has very good industrial application prospect. The experimental result shows that the raw material conversion rate of the preparation method provided by the invention is not less than 99.8%, and the product selectivity is not less than 99.5%
In addition, compared with the traditional kettle type reaction device, the preparation method provided by the invention has the advantages of short reaction time, small equipment volume and investment, environmental protection, safety and the like during the production, so that the preparation method has great advantages compared with the prior art.
To further illustrate the present invention, the following examples are provided for illustration. The starting materials used in the following examples of the present invention are all commercially available products.
Example 1
(1) Using Corning CorpA Lab Reactor reaction device, wherein a metering pump is used for simultaneously pumping the tert-butyl chloride and the 3,3, 3-trifluoro-1-propanol into a mixer of a microchannel Reactor, and the flow rate of the tert-butyl chloride is controlled to be 2.7g/min and the flow rate of the 3,3, 3-trifluoro-1-propanol is controlled to be 2.2g/min, so as to obtain a reaction raw material mixture;
(2) putting the reaction raw material mixture obtained in the step (1) into a microchannel reactor with the reaction gauge pressure of 9bar, and reacting at 100 ℃ for 80s to obtain reaction liquid; and cooling the reaction liquid to obtain product liquid containing the fluorine-containing asymmetric chain carbonate.
The product liquid obtained by the preparation method provided by the embodiment 1 of the invention is subjected to gas chromatography GC detection, and the result is as follows: the conversion of tert-butyl chloroformate was 87.3%, and the selectivity for fluorine-containing asymmetric chain carbonate was 86.9%.
Example 2
(1) Using Corning CorpG1-hybrid reaction equipment, using a metering pump to simultaneously pump tert-butyl chloroformate, 3,3, 3-trifluoro-1-propanol and 10 wt% potassium carbonate acetone suspension into a mixer of a microchannel reactor, controlling the flow rate of the tert-butyl chloroformate to be 13.6G/min, the flow rate of the 3,3, 3-trifluoro-1-propanol to be 11.4G/min and the flow rate of the 10 wt% potassium carbonate acetone suspension to be 69.1G/min, and obtaining a reaction raw material mixture;
(2) putting the reaction raw material mixture obtained in the step (1) into a microchannel reactor with the reaction gauge pressure of 5bar, and reacting at 60 ℃ for 60s to obtain reaction liquid; and cooling and layering the reaction liquid to obtain the product liquid containing the fluorine-containing asymmetric chain carbonate.
The product liquid obtained by the preparation method provided by the embodiment 2 of the invention is subjected to gas chromatography GC detection, and the result is as follows: the conversion of tert-butyl chloroformate was 98.3%, and the selectivity for fluorine-containing asymmetric chain carbonate was 97.5%.
Example 3
(1) Using Corning CorpA Lab Reactor reaction device, which is used for pumping dichloromethane solution of tert-butyl chloride, 3,3, 3-trifluoro-1-propanol and triethylamine into a mixer of a microchannel Reactor by using a metering pump, controlling the flow rate of the tert-butyl chloride to be 4.08g/min, the flow rate of the 3,3, 3-trifluoro-1-propanol to be 3.42g/min and the flow rate of the dichloromethane solution of the triethylamine to be 3.03g/min, and obtaining a reaction raw material mixture;
(2) putting the reaction raw material mixture obtained in the step (1) into a microchannel reactor with the reaction gauge pressure of 2bar, and reacting at 40 ℃ for 30s to obtain reaction liquid; and cooling the reaction solution, and washing with water to obtain a product solution containing the fluorine-containing asymmetric chain carbonate.
The product liquid obtained by the preparation method provided by the embodiment 3 of the invention is subjected to gas chromatography GC detection, and the result is as follows: the conversion of tert-butyl chloroformate was 98.81%, and the selectivity of fluorine-containing asymmetric chain carbonate was 98.55%.
Example 4
(1) Using Corning CorpG1-hybrid reaction equipment, using a metering pump to simultaneously pump tert-butyl chloroformate, 3,3, 3-trifluoro-1-propanol and 10 wt% potassium hydroxide aqueous solution into a mixer of a microchannel reactor, controlling the flow rate of the tert-butyl chloroformate to be 20.4G/min, the flow rate of the 3,3, 3-trifluoro-1-propanol to be 17.1G/min and the flow rate of the 10 wt% potassium hydroxide aqueous solution to be 84.1G/min, and obtaining a reaction raw material mixture;
(2) putting the reaction raw material mixture obtained in the step (1) into a microchannel reactor with the reaction gauge pressure of 1bar, and reacting at 60 ℃ for 60s to obtain reaction liquid; and cooling the reaction solution, and washing with water to obtain a product solution containing the fluorine-containing asymmetric chain carbonate.
The product liquid obtained by the preparation method provided by the embodiment 4 of the invention is subjected to gas chromatography GC detection, and the result is as follows: the conversion of tert-butyl chloroformate was 99.8%, and the selectivity of fluorine-containing asymmetric chain carbonate was 99.5%.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (10)
1. A method for preparing fluorine-containing asymmetric chain carbonate comprises the following steps:
a) weighing fluorine-containing monohydric alcohol, halogenated carbonate and an acid-binding agent according to a certain molar ratio, and preparing the raw materials, or dissolving the three raw materials in a solvent according to a certain molar ratio to prepare a solution;
b) introducing the three raw materials or a solution prepared from the three raw materials into a mixing module of a continuous flow reactor according to a specific feeding mode for premixing to obtain a reaction raw material mixture;
c) introducing the reaction raw material mixture obtained in the step b) into a reaction module of a continuous microchannel reactor for reaction to obtain a crude product of the fluorine-containing asymmetric chain carbonate, and performing post-treatment to obtain a finished product.
2. The method according to claim 1, wherein the fluorine-containing monohydric alcohol in step a) has a general formula of formula (I):
R1OH is formula (I);
in the formula (I), R1Is selected from-CF3、-CF2H、-CFH2、-CH2CF3、-CH2CF2H、-CH2CFH2、-CF2CF3、-CF2CF2H、-CF2CFH2、-CFHCF3、-CFHCF2H、-CFHCFH2、-CH(CF3)2、-CH2C2F5、-CH2CF2CF3、-CH2CF2CF2H、-CF2CF2CF3or-CF2CFHCF2CH2。
3. The method of claim 1, wherein the halogenated carbonate in step a) has the general formula of formula (II):
XCOOR2formula (II);
in the formula (II), X is selected from-F, -Cl, -Br or-I, R2Is selected from-CF2CH3、-CH2C2F5or-CH3、-C2H5。
4. The preparation method of claim 1, wherein the acid-binding agent in step a) is at least one selected from triethylamine, pyridine, imidazole, potassium carbonate, potassium bicarbonate, sodium carbonate, sodium bicarbonate, potassium hydroxide and sodium hydroxide.
5. The solvent according to claim 1, which is at least one selected from the group consisting of water, tetrahydrofuran, dichloromethane, 1, 4-dioxane, acetone and ethyl acetate.
6. The preparation method according to claim 1, wherein the molar ratio of the fluorine-containing monohydric alcohol, the halogenated carbonate and the acid-binding agent in step a) is (0.5-1.8): 1: (0 to 1.8).
7. The method according to claim 1, wherein the specific feeding manner in step b) is pumping; the pumping can be that three raw materials are divided into three parts to be fed simultaneously, or any two raw materials are premixed and then divided into two parts with the rest raw material to be fed simultaneously; the pumping flow rate is 2g/min to 5000 g/min.
8. The preparation method according to claim 1, wherein the continuous flow reactor in step b) is a microchannel reactor capable of realizing continuous reaction, and comprises a premixing module, a reaction module and a post-treatment module.
9. The preparation method of claim 1, wherein the continuous microchannel in step c) is reacted at a pressure of 0bar to 10bar, a temperature of 0 ℃ to 130 ℃ and a time of 5s to 180 s.
10. The preparation method according to claim 1, wherein the post-treatment in the step c) comprises cooling, layering after cooling or washing, purification and the like after cooling.
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