CN115894166A - Method for synthesizing 2, 3-tetrafluoropropene through gas phase fluorination - Google Patents

Method for synthesizing 2, 3-tetrafluoropropene through gas phase fluorination Download PDF

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CN115894166A
CN115894166A CN202211539700.9A CN202211539700A CN115894166A CN 115894166 A CN115894166 A CN 115894166A CN 202211539700 A CN202211539700 A CN 202211539700A CN 115894166 A CN115894166 A CN 115894166A
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tetrafluoropropene
fluorination
trifluoropropene
halogenated
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毛伟
吕剑
秦越
白彦波
贾兆华
赵锋伟
王博
何飞
石磊
亢建平
李凤仙
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Xian Modern Chemistry Research Institute
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Abstract

The invention discloses a method for synthesizing 2, 3-tetrafluoropropene through gas phase fluorination, which comprises the steps of firstly, in the presence of a chromium-free environment-friendly fluorination catalyst, contacting a gas phase with a fluorinating agent and a halogenating agent to prepare halogenated trifluoropropene, and reacting the halogenated trifluoropropene with the fluorinating agent in the presence of the chromium-free environment-friendly fluorination catalyst to prepare the 2, 3-tetrafluoropropene. The method has the advantages of cheap and easily-obtained raw materials, short synthesis steps, high selectivity of target products, no chromium in the catalyst, low carbon and environmental protection.

Description

Method for synthesizing 2, 3-tetrafluoropropene through gas phase fluorination
Technical Field
The invention relates to a method for synthesizing 2, 3-tetrafluoropropene through gas-phase catalytic fluorination.
Background
2, 3-tetrafluoropropene, HFO-1234yf for short, the Ozone Depletion Potential (ODP) is 0, the potential greenhouse effect (GWP) is less than 1, and the product is less than one thousandth of 1, 2-tetrafluoroethane (HFC-134a, GWP is 1430) which is the hydrofluorocarbon product with the largest use amount at present, but the physical property is similar to HFC-134a, and the product can be directly used for replacing the latter in the existing refrigerating system, is a novel environment-friendly refrigerant with the most development prospect, and is applied to large-scale commercial refrigeration and vehicle-mounted refrigeration.
Among the numerous HFO-1234yf synthesis processes known to date, the synthetic route starting from chloropropane includes the following. U.S. Pat. No. 4,8450537B 2 discloses a process for preparing a polymer of the formula CX 3 CH 2 CH 2 X、CX 3 CH＝CH 2 Or CH 2 XCH＝CX 2 (wherein each X is independently selected from the group consisting of F and Cl) with HF, cl and a chromium-containing catalyst 2 (HF/starting material is in stoichiometric ratio, cl) 2 Raw material is 2) to generate 2, 3-tetrafluoropropene, 1, 2-pentafluoropropane 2-chloro-3, 3-trifluoropropene, and the like. Chinese patent CN101979364B discloses a method for preparing 2,3,3,3-tetrafluoropropene by using 3,3,3-trifluoropropene as raw material and carrying out four-step reactions of photochlorination, liquid-phase HCl removal, liquid-phase fluorination and liquid-phase HCl removal. Chinese patent CN103946192B discloses a method for preparing 2-chloro-3,3,3-trifluoropropene from 1,1,2,3-tetrachloropropene by gas phase or liquid phase fluorinationAnd then under the action of a chromium-containing catalyst, the 2, 3-tetrafluoropropene is synthesized with HF under the gas-phase reaction condition. Chinese patent CN102099319B discloses a method for synthesizing 2,3,3,3-tetrafluoropropene by using 1,1,1,3-tetrachloropropane as a starting material, first fluorinating the starting material to convert the starting material into 3,3,3-trifluoropropene, then chlorinating the starting material to convert the starting material into 1,1,1-trifluoro-2,3-dichloropropane, then dehydrochlorinating the starting material to prepare 2-chloro-3,3,3-trifluoropropene, and finally performing liquid phase fluorination and high temperature dehydrochlorination to synthesize 2,3,3,3-tetrafluoropropene.
Although the above reported synthetic route has a certain effect in the technical field of HFO-1234yf synthesis, the problems of long reaction steps, poor selectivity, low efficiency, high energy consumption and poor economy generally exist, and catalysts for gas phase fluorination all use chromium as a core component, but chromium is a heavy metal element, and serious pollution is caused to the ecological environment due to large-scale emission; in particular, hexavalent chromium is a toxic substance which poses a great threat to the health of animals and human beings. Based on the above, in order to respond to the policy of 'double carbon', promote energy conservation and emission reduction in the chemical production process and respond to increasingly strict environmental laws and regulations, a new low-carbon and environment-friendly HFO-1234yf synthesis route needs to be developed urgently, and a high-performance chromium-free fluorination catalyst is used.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide a method for synthesizing 2, 3-tetrafluoropropene through gas phase fluorination, so as to solve the problems of long route, poor selectivity, complex separation, low efficiency, large environmental hazard of a catalyst containing heavy metal chromium and the like in the traditional technology; the method has the advantages of cheap and easily-obtained raw materials, short synthesis steps, few reaction steps, high selectivity of target products, no chromium in the catalyst, low carbon and environmental protection.
In order to solve the technical problems, the invention adopts the following technical scheme to realize:
a process for synthesizing 2, 3-tetrafluoropropene by gas-phase fluorination uses chloropropane as raw material, and firstly, in the presence of chromium-free environment-friendly fluorination catalyst, the gas phase is contacted with fluorinating agent and halogenating agent to prepare halogenated trifluoropropene, which reacts with fluorinating agent in the presence of chromium-free environment-friendly fluorination catalyst to prepare 2, 3-tetrafluoropropene.
The invention also comprises the following technical characteristics:
specifically, the method comprises the following steps:
step 1, in a first reactor, in the presence of a first fluorination catalyst, contacting chloropropane with a fluorinating agent and a halogenating agent at 150-300 ℃ and 0.1-1.0 MPa, and converting into halogenated trifluoropropene;
and 2, in a second reactor, in the presence of a second fluorination catalyst, contacting the halogenated trifluoropropene obtained in the step 1 with a fluorinating agent at the temperature of 300-450 ℃ and the pressure of 0.1-1.0 MPa, and converting into the 2, 3-tetrafluoropropene.
Specifically, in step 1, the first fluorination catalyst is a chromium-free environment-friendly fluoride catalyst comprising FeOxFy (2x + y = 3) and magnesium fluoride; the chloropropane is 1, 3-tetrachloropropane or 3, 3-trichloropropene; the fluorinating agent is anhydrous hydrogen fluoride; the halogenating agent is chlorine or bromine; the chemical formula of the halogenated trifluoropropene is CF 3 CX＝CH 2 Wherein X = Cl or Br.
Specifically, in the step 1, the molar ratio of the chloropropane to the fluorinating agent and the halogenating agent is 1/10-50/1-2.
Specifically, in the step 1, the first fluorination catalyst further comprises an auxiliary agent, and the auxiliary agent comprises lanthanum, copper, nickel and zirconium; the proportion of the auxiliary agent, feOxFy and magnesium fluoride in the total weight of the first fluorination catalyst is 1-5%, 10-20% and 78-88% respectively.
Specifically, in step 2, the second fluorination catalyst is a chromium-free environment-friendly fluoride catalyst comprising FeOxFy (2x + y = 3), aluminum fluoride or magnesium fluoride; the fluorinating agent is anhydrous hydrogen fluoride.
Specifically, in the step 2, the molar ratio of the halogenated trifluoropropene to the fluorinating agent is 1/10-50.
Specifically, in the step 2, the second fluorination catalyst further comprises an auxiliary agent, and the auxiliary agent comprises titanium, tin, gallium and cobalt; the auxiliary agent, feOxFy, aluminum fluoride or magnesium fluoride account for 1 percent to 5 percent, 10 percent to 20 percent and 77 percent to 89 percent respectively in the total weight of the second fluorination catalyst.
Specifically, the specific surface area of the magnesium fluoride and the aluminum fluoride is more than 100m 2 The pore size distribution is 5-15 nm, and the thermal stability is more than 400 ℃.
Specifically, the chloropropane is converted to halogenated trifluoropropene for at least 80% in the first reactor, and the halogenated trifluoropropene is converted to 2,3, 3-tetrafluoropropene for at least 40% in the second reactor.
Compared with the prior art, the invention has the following technical effects:
(1) compared with the traditional preparation method, the invention provides a novel preparation method of HFO-1234yf, which has the advantages of cheap and easily obtained raw materials, short reaction step, simple separation, high selectivity and environmental friendliness; (2) the invention provides a fluorination catalyst which does not contain chromium and other heavy metals, has environment-friendly high activity and high selectivity and takes FeOxFy (2x + y= 3) as an active center; (3) the composition catalyst of FeOxFy (2x + y = 3) and magnesium fluoride used in the invention can make chloropropane contact with fluorinating agent and halogenating agent to generate halogenated trifluoropropene with high activity and high selectivity; (4) the FeOxFy (2x + y = 3) and aluminum fluoride composite catalyst used in the invention can make halogenated trifluoropropene contact with fluorinating agent, and can generate 2, 3-tetrafluoropropene with high activity and high selectivity.
Drawings
FIG. 1 is a schematic diagram of a process for preparing 2,3,3,3-tetrafluoropropene according to the present invention.
Detailed Description
The invention provides a method for synthesizing 2, 3-tetrafluoropropene by gas-phase fluorination, which takes chloropropane as a raw material, firstly, in the presence of a chromium-free environment-friendly fluorination catalyst, gas phase contacts with a fluorinating agent and a halogenating agent to prepare halogenated trifluoropropene, and secondly, the halogenated trifluoropropene reacts with the fluorinating agent in the presence of the chromium-free environment-friendly fluorination catalyst to prepare 2, 3-tetrafluoropropene; the method comprises the following steps:
step 1, in a first reactor, in the presence of a first fluorination catalyst, contacting chloropropane with a fluorinating agent and a halogenating agent at 150-300 ℃ and 0.1-1.0 MPa, and converting into halogenated trifluoropropene;
specifically, in step 1, the first fluorination catalyst is a chromium-free environment-friendly fluoride catalyst comprising FeOxFy (2x + y = 3) and magnesium fluoride; the chloropropane is 1,1,1,3-tetrachloropropane or 3, 3-trichloropropene; the fluorinating agent is anhydrous hydrogen fluoride; the halogenating agent is chlorine or bromine; the chemical formula of the halogenated trifluoropropene is CF 3 CX＝CH 2 Wherein X = Cl or Br; the mol ratio of the chloropropane to the fluorinating agent and the halogenating agent is 1/10-50/1-2;
more specifically, the first fluorination catalyst also comprises an auxiliary agent, wherein the auxiliary agent comprises lanthanum, copper, nickel and zirconium; the proportion of the auxiliary agent, feOxFy and magnesium fluoride in the total weight of the first fluorination catalyst is 1-5%, 10-20% and 78-88% respectively;
step 2, in a second reactor, in the presence of a second fluorination catalyst, contacting the halogenated trifluoropropene obtained in the step 1 with a fluorinating agent at the temperature of 300-450 ℃ and the pressure of 0.1-1.0 MPa, and converting the halogenated trifluoropropene into 2, 3-tetrafluoropropene;
specifically, in step 2, the second fluorination catalyst is a chromium-free environment-friendly fluoride catalyst, which comprises FeOxFy (2x + y =3), aluminum fluoride or magnesium fluoride; the fluorinating agent is anhydrous hydrogen fluoride; the mol ratio of the halogenated trifluoropropene to the fluorinating agent is 1/10-50;
more specifically, the second fluorination catalyst further comprises an auxiliary agent, wherein the auxiliary agent comprises titanium, tin, gallium and cobalt; the proportion of the auxiliary agent, feOxFy, aluminum fluoride or magnesium fluoride in the total weight of the second fluorination catalyst is 1-5%, 10-20% and 77-89% respectively;
the specific surface area of magnesium fluoride and aluminum fluoride is more than 100m 2 The pore size distribution is 5-15 nm, and the thermal stability is more than 400 ℃.
The chloropropanes are at least 80% converted to halogenated trifluoropropenes in the first reactor, and the halogenated trifluoropropenes are at least 40% converted to 2, 3-tetrafluoropropene in the second reactor.
The following embodiments are given as examples of the present invention, and it should be noted that the present invention is not limited to the following embodiments, and all equivalent changes based on the technical solutions of the present invention are included in the protection scope of the present invention.
Example 1:
this example provides a process for the vapor phase fluorination synthesis of 2, 3-tetrafluoropropene comprising the steps of:
step 1, preparation of 2-bromo-3, 3-trifluoropropene from 1, 3-tetrachloropropane:
transferring the first fluorination catalyst into a fixed bed tubular reactor, heating to a set temperature, drying for 2h, introducing hydrogen fluoride and bromine, introducing 1, 3-tetrachloropropane, allowing the contact time to be 8 seconds, allowing the product to run for 12h to absorb the hydrogen fluoride, the hydrogen chloride and the hydrogen bromide through water and alkali washing, and allowing the product to enter a gas chromatograph for analysis, and calculating the conversion rate of the 1, 3-tetrachloropropane and the selectivity of a target product, namely 2-bromo-3, 3-trifluoropropene, by using an area normalization method; specifically, the first fluorination catalyst in this embodiment includes FeOxFy (2x + y = 3), magnesium fluoride and an auxiliary agent, and the auxiliary agent includes lanthanum, copper, nickel, zirconium; wherein 30mL of a composition of FeOxFy (2x + y = 3) and magnesium fluoride is measured, and the specific surface area of the magnesium fluoride after being calcined at 400 ℃ is 108m 2 G, pore diameter of 15nm.
The components and proportion of the first fluorination catalyst, the reaction temperature, the reaction pressure and the like in the step 1, and the reaction results are shown in the following table:
TABLE 1 reaction results for the preparation of halotrifluoropropenes from chloropropanes
Figure BDA0003976847840000041
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Figure BDA0003976847840000051
Step 2, preparation of 2, 3-tetrafluoropropene from 2-bromo-3, 3-trifluoropropene:
taking a second fluorination catalyst, transferring the second fluorination catalyst into a fixed bed tubular reactor, heating to a set temperature, drying for 2 hours, introducing hydrogen fluoride, then introducing 2-bromo-3, 3-trifluoropropene, allowing the contact time to be 12 seconds, washing the product after running for 12 hours by water and alkali to absorb the hydrogen fluoride and the hydrogen bromide, and then analyzing the product by a gas chromatograph, and calculating the conversion rate of the 2-bromo-3, 3-trifluoropropene and the selectivity of the target product 2, 3-tetrafluoropropene by adopting an area normalization method; specifically, the second fluorination catalyst in this embodiment comprises FeOxFy (2x + y = 3), aluminum fluoride or magnesium fluoride and an auxiliary agent comprising titanium, tin, gallium,Cobalt; wherein, measuring 30mL of a composition of FeOxFy (2x + y = 3) and aluminum fluoride or magnesium fluoride as a catalyst, wherein the specific surface area of the aluminum fluoride after being calcined at 400 ℃ is 168m 2 G, pore diameter of 8nm.
The components and proportion of the second fluorination catalyst, the reaction temperature, the reaction pressure and the like in the step 2, and the reaction results are shown in the following table:
TABLE 2 reaction results of halo-trifluoropropene production of 2,3,3,3-tetrafluoropropene
Figure BDA0003976847840000052
Example 2:
this example provides a process for the vapor phase fluorination synthesis of 2, 3-tetrafluoropropene comprising the steps of:
step 1, preparation of 2-chloro-3, 3-trifluoropropene from 3, 3-trichloropropene:
the same first fluorination catalyst as in example 1 was used, in which magnesium fluoride had a specific surface area of 118m after calcination at 400 ℃ 2 The pore diameter is 10nm, the method is applied to the reaction of 3, 3-trichloropropene, hydrogen fluoride and chlorine under the gas phase reaction condition to synthesize 2-chloro-3, 3-trifluoropropene, and the operation is carried out for 12 hours; the components and proportion of the first fluorination catalyst, the reaction temperature, the reaction pressure and the like in the step 1, and the reaction results are shown in the following table:
TABLE 3 reaction results for the preparation of haloprifluoropropenes from chloropropanes
Figure BDA0003976847840000061
Step 2, preparation of 2, 3-tetrafluoropropene from 2-chloro-3, 3-trifluoropropene
A second fluorination catalyst which was the same as in example 1 and in which aluminum fluoride had a specific surface area of 188m after calcination at 400 ℃ was used 2 The pore diameter is 5nm, the method is applied to the synthesis of 2, 3-tetrafluoropropene by the reaction of 2-chloro-3, 3-trifluoropropene and hydrogen fluoride under the gas phase reaction condition, and the operation lasts for 12 hours; second fluorination catalyst component and proportion in step 2, and reaction temperatureReaction pressure, etc., and the reaction results are as follows:
TABLE 4 reaction results of halo-trifluoropropene production of 2,3,3,3-tetrafluoropropene
Figure BDA0003976847840000062
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Claims (10)

1. A method for synthesizing 2, 3-tetrafluoropropene through gas-phase fluorination is characterized in that chloropropane is used as a raw material, firstly, in the presence of a chromium-free environment-friendly fluorination catalyst, the gas phase is contacted with a fluorinating agent and a halogenating agent to prepare halogenated trifluoropropene, and the halogenated trifluoropropene reacts with the fluorinating agent in the presence of the chromium-free environment-friendly fluorination catalyst to prepare the 2, 3-tetrafluoropropene.
2. The gas-phase fluorination synthesis process of 2, 3-tetrafluoropropene according to claim 1, characterized by comprising the following steps:
step 1, in a first reactor, in the presence of a first fluorination catalyst, contacting chloropropane with a fluorinating agent and a halogenating agent at 150-300 ℃ and 0.1-1.0 MPa, and converting into halogenated trifluoropropene;
and 2, in a second reactor, in the presence of a second fluorination catalyst, contacting the halogenated trifluoropropene obtained in the step 1 with a fluorinating agent at the temperature of 300-450 ℃ and the pressure of 0.1-1.0 MPa, and converting into the 2, 3-tetrafluoropropene.
3. The gas-phase fluorination synthesis method for 2,3,3,3-tetrafluoropropene as claimed in claim 2, wherein in the step 1, the first fluorination catalyst is a chromium-free environment-friendly fluoride catalyst comprising FeOxFy (2x + y = 3) and magnesium fluoride; the chloropropane is 1, 3-tetrachloropropane or 3, 3-trichloropropene; the fluorinating agent is anhydrous hydrogen fluoride; the halogenating agent is chlorine or bromine; the chemical formula of the halogenated trifluoropropene is CF 3 CX＝CH 2 Wherein X = Cl or Br.
4. The process for the gas-phase fluorination synthesis of 2, 3-tetrafluoropropene according to claim 3, wherein in step 1, the molar ratio of chloropropane to fluorinating and halogenating agents is from 1/10 to 50/1 to 2.
5. The gas-phase fluorination synthesis method of 2, 3-tetrafluoropropene according to claim 3, wherein in step 1, the first fluorination catalyst further comprises auxiliaries, and the auxiliaries comprise lanthanum, copper, nickel and zirconium; the auxiliary agent, feOxFy and magnesium fluoride account for 1-5%, 10-20% and 78-88% of the total weight of the first fluorination catalyst respectively.
6. The gas phase fluorination synthesis method of 2,3,3,3-tetrafluoropropene as claimed in claim 3, wherein in the step 2, the second fluorination catalyst is a chromium-free environment-friendly fluoride catalyst comprising FeOxFy (2x + y = 3), aluminum fluoride or magnesium fluoride; the fluorinating agent is anhydrous hydrogen fluoride.
7. The gas-phase fluorination synthesis process of 2, 3-tetrafluoropropene according to claim 6, wherein in step 2, the molar ratio of halogenated trifluoropropene to fluorinating agent is from 1/10 to 50.
8. The vapor phase fluorination synthesis process of 2, 3-tetrafluoropropene as claimed in claim 6, wherein in step 2, the second fluorination catalyst further comprises promoters comprising titanium, tin, gallium, cobalt; the proportion of the auxiliary agent, feOxFy, aluminum fluoride or magnesium fluoride in the total weight of the second fluorination catalyst is 1-5%, 10-20% and 77-89% respectively.
9. The process for the gas-phase fluorination synthesis of 2, 3-tetrafluoropropene according to claim 6, wherein the magnesium fluoride and the aluminium fluoride have a specific surface area greater than 100m 2 G, the pore size distribution is 5-15 nm, and the thermal stability is more than 400 ℃.
10. The gas phase fluorination process of synthesizing 2,3,3,3-tetrafluoropropene according to claim 2 wherein the chloropropane is converted to halogenated trifluoropropene in the first reactor at least 80% and the halogenated trifluoropropene is converted to 2,3,3,3-tetrafluoropropene in the second reactor at least 40%.
CN202211539700.9A 2022-12-02 2022-12-02 Method for synthesizing 2, 3-tetrafluoropropene through gas phase fluorination Pending CN115894166A (en)

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